Indian Patents. 262794:"A DIACETAL COMPOUND"

Title of Invention	"A DIACETAL COMPOUND"
Abstract	A diacetal compound conforming to the structure: wherein; n is 0,1 or 2 Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and R is selected from the group consisting of alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides, wherein the hydroyl alkyls are selected from the group consisting of-CHOHCHOHCH2OH, where X''' is a halide group.

Full Text	Title of the Invention ACETAL-BASED COMPOUNDS AND METHODS Background of the Invention Derivatives of acetals of polyhydric alcohols are useful in several applications, including for example as nucleating agents for polymer resins, and as gelling and thickening agents for organic liquids. Dibenzylidene sorbitol type (DBS) compounds are known for use in such applications. The use of nucleating agents to reduce the haze in articles manufactured from crystalline polyolefin resins is known in the art. Representative acetals of sorbitol and xylitol, which have been employed as clarifying agents, are described in several patents, including for example: Hamada, et al., United States Patent No. 4,016,118, dibenzylidene sorbitols; Kawai, et al., United States Patent No. 4,314,039, di(alkylbenzylidene) sorbitols; Mahaffey, Jr., United States Patent No. 4,371,645, di-acetals of sorbitol having at least one chlorine or bromine substituent; Kobayashi, et al., United States Patent No. 4,954,291, distribution of diacetals of sorbitol and xylitol made from a mixture of dimethyl ortrimethyl substituted benzaldehyde and unsubstituted benzaldehyde. Another reference, United States Patent - No. 5,049,605 to Rekers et al. discloses bis(3,4-dialkylbenzylidene) sorbitols, including substituents forming a carbocyclic ring. Substitution of various groups upon the benzyl ring portion(s) of DBS-based compounds may have a significant impact upon the suitability of such compounds as nucleating or clarifying agents. A significant amount of work in the past has been directed to modifying the substitution of the benzylidene ring substituent(s). However, efforts still are underway to develop other compounds that are likely to afford reduced haze (and corresponding greater clarity) when used as plastic additives in polymer compositions. The chemical arts often are unpredictable. Changing any portion or substituted group in these particular types of compounds may have a significant impact upon the performance and utility of the compound. This invention recognizes important new compositions that have not been known before, and may be quite useful as plastic additives, or as gelling agents, thickeners, or for other purposes. Detailed Description of the Invention Reference now will be made to the embodiments of the invention, one or more examples of which are set forth below. Each example is provided by way of explanation of the invention, not as a limitation of the invention. It will be apparent to those skilled in the art that various modifications and variations can be made in this invention without departing from the scope or spirit of the invention. A polyolefin additive composition is disclosed herein. In some applications, the polyolefin additive composition provides improved transparency to plastic polymer compositions when added to such compositions. In some applications, the additive composition will be advantageous when used in connection with polypropylene, although various applications in connection with other polymers are within the scope of the invention. Olefin polymers which can be nucleated by such compositions (and whose transparency may be improved according to the practice of the invention) include polymers and copolymers of aliphatic mono-olefins containing from 2 to about 6 carbon atoms, which have an average molecular weight of from about 10,000 to about 2,000,000, preferably from about 30,000 to about 300,000, such as polyethylene, including linear low density polyethylene, low density polyethylene and high density polyethylene, polypropylene, crystalline ethylene/propylene copolymer (random or block), poly(l-butene) and polymethylpentene. Examples of other thermoplastic polymer resins which may be nucleated with the disclosed acetal compounds include polyester, poly(ethylene terephthalate) (PET) and poly(butylene terephthalate) and polyamide, including nylon 6 and nylon 6,6, poly(phenylene sulfide), syndiotactic polystyrene and polyketones having carbonyl groups in their backbone. The composition may comprise a polymer selected from aliphatic polyolefins and copolymers containing at least one aliphatic olefiri and one or more ethylenically unsaturated comonomers and at least one mono-, di-, ortri-acetal of substituted alditol (such as allyl-sorbitol, propyl-sorbitol, allyl-xylitol, propyl-xylitol and the like). The mono-, di-, ortri-acetal of substituted alditol may include a composition as described below. For example, and not by way of limitation, a substituted alditol as in Formula (I), which is combined with at least one mole of benzaldehyde selected from the compounds with Formula (II), as shown below. For Formula (I): n is 0, 1, or 2; and R is independently selected from non-hydrogen groups including alkenyl groups (such as allyl), alkyl groups, alkoxy groups, hydroxyl alkyl groups, alkyl-halide groups. For Formula (II), R-i, Ra, Rs, R An acetal compound may be formed in one particular embodiment of the invention by the process of: (a) reacting a polyhydric alcohol with an alkenyl molecule to form a first compound; and (b) reacting in a condensation reaction said first compound with an aromatic aldehyde to form an acetal compound. However, the invention may be practiced in other ways as well. The acetal compound thus formed may be a mono- , di-, or tri- acetal, but in many cases it has been found that a di-acetal is particularly useful. The acetal compound may comprise an allyl in one particular embodiment of the invention, as herein further described. In some applications, such a reaction product or resulting composition is a di-acetal (and thus the result of a 1:2 molar ratio reaction between the alditol and benzaldehyde). A composition may be provided having the structure of Formula (III), below. A single acetal, or a triacetal, could also be provided in the practice of the invention, but one particular di-acetal composition is shown below: In the composition, n may be 0,1, or 2; and An and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups. Furthermore, R may be selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides. R may comprise an alkenyl, and in some particular embodiments of the invention, an allyl has been found to work quite well for the R group. It should be appreciated that the R group stereochemistry is not defined, and the invention is not limited to any particular R group stereochemistry, such that all chemical structures provided herein shall cover any isomers that occur due to stereoisomers of the carbon atom to which R is attached. It should be appreciated with regard to the composition set forth above that while only the 1,3; 2:4 isomer is represented (i.e. the numbered carbons on the sorbitol chain which form the two acetals), this structure is provided for convenience and illustration only and the invention is not limited to only isomers of the 1,3: 2,4 type, but may include any and all other isomers as well, including also isomers of the 1:3; 4:6 and 2,4:3,5 type, as examples. The diacetals, triacetals, and monoacetals of the invention may be condensation products of substituted alditols, such as (but not limited to) allyl-sorbitol, propyl-sorbitol, 1-methyl-2-propenyl sorbitol, allyl-xylitol, propyl-xylitol, and a (substituted) benzaldehyde. Examples of suitable (substituted) benzaldehydes include benzaldehyde, 4- ethylbenzaldehyde, 4-isobutylbenzaldehyde, 4-fluoro-3- methylbenzaldehyde, 5,6,7,8-tetrahydro-2-naphthaldehydebenzylidene, 3-methylbenzaldehyde, 4-propylbenzaldehyde, 4-butylbenzaldehyde, 4-methoxybenzaldehyde, 3-chlorobenzaldehyde, 3,4-dimethylbenzaldehyde, 3,5-difluorobenzaldehyde, 3-fluorobenzaldehyde, 4-fluorobenzaldehyde, 3-bromo-4-fluorobenzaldehyde, 3-methyl-4- methoxybenzaldehyde, 2,4,5-trimethylbenzaldehyde, 4-chloro-3-fluorobenzaldehyde, 4-methylbenzaldehyde, 3-bromobenzaldehyde, 4- methoxybenzaldehyde, 3,4-dichlorobenzaldehyde, 4-fluoro-3,5- dimethylbenzaldehyde, 2,4-dimethylbenzaldehyde, 4- bromobenzaldehyde, 3-ethoxybenzaldehyde, 4-allyloxybenzaldehyde, 3,5-dimethylbenzaldehyde, 4-chlorobenzaldehyde, 3- methoxybenzaldehyde, 4-(trifluoromethyl)benzaldehyde, 2- naphthaldehyde, 4-isopropylbenzaldehyde, 3,4-diethoxybenzaldehyde, 3-bromo-4-ethoxybenzaldehyde, piperonal, 3,4-dimethoxybenzaldehyde, 4-carboxybenzaldehyde, 3-hex-1-ynylbenzaldehyde, and 2- include 1,3:2,4-bis(4-ethylbenzylidene)-1-allyl-sorbitol, 1,3,2,4-bis(3'- methyl-4'-fluoro-benzylidene)-1 -propyl-sorbitol, 1,3,2,4-bis(5',6',7',8'-tetrahydro-2-naphthaldehydebenzylidene)-1 -allyl-xylitol, bis-1,3,2-4-(3',4'-dimethylbenzylidene)-1 "-methyl-2"-propyl-sorbitol, 1,3,2,4-bis(3',4'-dimethylbenzylidene)-1 -propyl-xylitol. The di-acetals and mono-acetals of the present invention may be prepared by a variety of techniques, some of which are known in the art. Generally, such procedures employ the reaction of one mole of substituted alditol (such as allyl-sorbitol, propyl-sorbitol, allyl-xylitol, mole of aldehyde (for monoacetals), or with 3 moles of aldehyde (for triacetals) in the presence of an acid catalyst (inorganic acid such as hydrochloric acid or organic acid such as p-toluenesulfonic acid (pTSA)). Further, an organic solvent is employed that is miscible with water (such temperature. In the practice of the invention, it is possible to have any number of DBS moities on the structure. It is common to have one, two, or three DBS (i.e. aryl-containing) moities on the hydrocarbon backbone. Below are several examples that can be employed in the method of nucleating a polyolefin composition. That is, one may employ one or more of the following: wherein: Ar, An and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and R is selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, alkyl-halides and derivatives thereof. Also, co-additives may be combined with said polyolefin composition. Examples of co-additives that can be used are set forth below in (1) - (3). Example 21 below shows yet another example of a co-additives lauryl sulfuric acid Na, that may be employed. Many other examples could be employed, and the co-additives below could be used with essentially any of the nucleating agent structures or compositions disclosed herein. Also, more than one co-additive set forth below could be employed, and the amount or concentrion employed would vary for a given application. (1) Co-additives for inhibiting migration of odor and taste. Alkali metal salts of amino acids (at least one amino acid chosen from the following: glycine, L-alanine, L-phenyl-aianine, L-isoleucine, L- valine, L-leucine, L-proline, L-arginine, L-asparatic acid, L-cystine, L- glutamic acid, L-serine, L- histidine, L-tryptophan, L-lysine, L-threonine, L-methionine, DL-ethionine, L-cysteine, L-tyrosine, L-asparagine, L- glutamine, L-norvaline, and L-a-amino butyric acid.) and 0.1 to 100 parts by weight of at least one fatty acid with 8-32 carbon atoms (octane acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, 12- hydroxy stearic acid, behenic acid, montan acid, oleic acid, linoleic acid, ereo-stearic acid, ricinoleic acid, and erucic acid ). (2) Co-additives for inhibiting migration of odor and taste and depression the melting point of DBS: A: At least a saturated or unsaturated aliphatic alcohol with 6-32 carbon atoms (for example: lauric alcohol). B: and at least a saturated or unsaturated aliphaltic carboxylic acid with 8-32 carbon atoms having at least one hydroxy group within the molecule (for example: 12-hydroxy stearic acid), C: at least one type chosen from the following groups: lithium salt, sodium salt, or potassium salt of a saturated or unsaturated fatty acid with 8-32 carbon atoms that may have at least one hydroxyl group within the molecule, or D: at least one type sulfuric acid ester salt chosen from the following group: lauryl sulfuric acid salt, stearyl sulfuric acid salt, oleyl sulfuric acid salt, and polyoxyethylene stearyl ether sulfuric acid salts. (3) Co-Additives having a granular or powdery diacetal composition: wherein the binder is selected from the group consisting of monocarboxylic acids, polycarboxylic acids, partial salts of polycarboxylic acids, esters of phosphoric acid and at least one member selected from the group consisting of C1-C30 monohydric aliphatic alcohols and C2-C30 polyhydric aliphatic alcohols, esters of phosphorous acid and at least-one member selected from the group consisting of C1-C30 monohydric aliphatic alcohols and C2-C30 polyhydric aliphatic alcohols, esters of phosphoric acid and at least one member selected from the group consisting of C6-C30 monohydric aromatic alcohols and C6-C30 polyhydric aromatic alcohols, esters of phosphorous acid and at least one member selected from the group consisting of C6-C30 monohydric aromatic alcohols and C6-C30 polyhydric aromatic alcohols, taurine, salts of sulfuric acid ester, sulfonic acid salts, salts of phosphoric acid ester and mono-, di- and tri(C6-C30 fatty acid) aluminum salts, each of which may have, in the molecule, at least one bond or functional group selected from the group consisting of an ether bond, an ester bond, a thioether bond, an amide bond, a halogen atom, amino group, hydroxyl groups, a heterocyclic group and carbonyl group. Synthesis Methods for Di-Acetals One method that can be employed to prepare di-acetals of the invention is described in United States Patent No. 5,106,999 to Gardlik et al., which is hereby incorporated by reference. Methods to prepare and synthesize the carbohydrates of varying chain length are disclosed in Kim, Gordon, Schmid, and Whitesides, Tin and Indium Mediated Allylation in Aqueous Media: Application to Unprotected Carbohydrates, J. Org. Chem, 5500-5507, 58 (1993) and in Whiteside, Journal of the American Chemical Society, 113, 6674-6675 (1991). Whiteside has suggested the reaction of glucose with allyl bromide/tin. One reaction method that may be employed in the preparing starting materials for the synthesis of compositions needed in the practice of the invention are shown below, in which an allyl group may be added to a carbohydrate. The reaction scheme illustrated is merely one example, and similar reactions can be carried out for carbohydrates having more or less carbon groups in the chain. HO OH BrCH2CH=CH2, Sn OH-C — 1 ^ — C— OH —OH —OH HO —OH —OH —OH —OH CH2OH , ikUOH 1,2,3-trideoxy-D-glycero-D-ido-nonenitol 1,2,3-trideoxy-D-glycero-D-gulo-nonenitol OH—C— -OH —C—OH -OH HO HO -OH -OH CH2OH 1,2,3-trideoxy-D-ido-octenitol CH2OH 1,2,3-trideoxy-D-gulo-octenitol In the practice of the invention, an acetal compound formed by the process of: (a) reacting a carbohydrate and an alkenyl group to form a first compound; and (b) reacting in a condensation reaction said first compound with an aromatic aldehyde to form an acetal compound. In some applications, the alkenyl group comprises an allyl. It has been discovered in the course of work leading to one embodiment of the invention herein that allyl bromide/tin chemistry as illustrated above is one manner of synthesis for a carbohydrate hydrocarbon chain that can be used as one step in a sequence of reactions to unexpectedly provide significant advantages and valuable compositions. This general reaction pathway may be used in various forms to synthesize carbohydrates in the manufacture of the compositions of the invention. One embodiment of the invention relates to the use of carbohydrate synthesis reactions in combination with other acetal formation reactions to prepare compositions of the invention. Substituted sorbitol diacetals, triacetals, and monoacetals may be prepared. These structures contain mixtures of any correlated types of acetals (such as the related di-, tri-, and/or mono-acetals of the target acetal). Although it may not always be necessary to remove these impurities (particularly if they are present in very low proportions) prior to incorporation of the di-acetal, triacetal or monoacetal into the target polyolefin, it may be desirable to do so and such purification may serve to enhance the transparency of the resin produced thereby. Purification of a di-acetal may be accomplished, in one embodiment of the invention, by removal of any present tri-acetals by the extraction thereof with a relatively non-polar solvent. As one non- limited example, by removal of the impurities, the product may be purified so that the amount of di-acetal in the additive composition contains at least about 95 percent and even up to 98 percent di-acetal or more, depending upon the application. A more complete synthesis pathway is shown below, which is merely illustrative, and not limited to only those species or reactions shown: CH2OH OH HO— C Q RrrH-,rH=rFU Sn r > OH OH 3H Ul 1 VVWOH EtOH-H")O Mn \-ir\ OH C OH )H Ul 1 UM CH2OH ArCHO Generic Structure of a Synthesized Acetal-based Composition Many different substituted benzyl groups may be employed for Ar-i and Ar2 in the practice of the invention, as shown by several representative examples in Table 1, which were synthesized and tested as shown in the Examples listed herein. Substituted groups for An and/or Ar2 are not limited to only those found in Table 1. For example, Table 1 reports various compositions for which n= 0 and where n=1 for various substituted An, and Ar2 groups. When n = 0, the xylitol moity is employed. When n = 1 , the sorbitol moity is employed. Although n = 2 compounds are not reported in Table 1 , such compounds are within the scope of the invention, and are within the teachings provided herein. There is no practical limit to what may be substituted in such compositions, so long as they are chemically possible. However, it has been found that certain substituted groups on this compound provide enhanced properties. In the practice of the invention, R may be selected from a wide variety of compounds, including without limitation and by way of example: -CH2CH2CH3; -CH2CH2CH2CH3; -CH2CH=CH2; -CH(CH3)CH=CH2; -CH2CH-X-CH2-X' ; -CH2CH2.X"-CH2-CH3 ; -CH2CH-X'"-CH2OH; -CH-OH-CH-OH-CH2.OH. With regard to the compounds above, X, X1, X" , and X1" comprise independently selected halide groups in those selected compounds, if they are employed. The allyl species (-CH2CH=CH2) is sometimes particularly advantageous, and several such species were synthesized and reported along with others in A 3L, three-necked round bottom flask, equipped with heating mantle, stirrer, nitrogen inlet, and condensor, was charged with 900 mL of ethanol, 150 ml of water, 180 g (1.00 mole) of D-glucose, 119 g (1.00 mole) of tin powder (-100 mesh), and 121 g (1.00 mole) of allyl bromide. The mixture was stirred and slowly heated to reflux - a significant exotherm and gas evolution was observed at 60°C. The gray suspension was stirred at reflux for two days, in which time the reaction mixture turned an orange/brown color. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was neutralized to pH = 7 by adding approximately 200 ml of 5M NaOH aqueous solution. The suspension was filtered to remove solids, and the yellow solution was decolorized with multiple treatments of activated carbon. The activated carbon was removed by filtration, and the solvent was removed by rotary evaporation to isolate a white syrup. Typical yield was 200g with threo-erythro ratio of 1:6, based on GC-MS. The syrup was used without further purification. Pure erythro isomer could be obtained by hydrolysis of any of the example 2-8. 1H NMR (500 MHz, D2O, ppm): 2.34-2.37 (m, 2H), 3.63-3.95 (m, 7H), 5.13-5.20 (m, 2H), 5.88-5.89 (m, 1H). 13C NMR (125 MHz, D2O, ppm): 38.32, 63.69, 70.74, 71.14, 71.80, 71.92, 74.58, 118.60, 135.72. A 2L reaction kettle, equipped with a stirrer and nitrogen inlet, was charged with 111 g (0.50 mol) of 1-allyl sorbitol syrup (product of Example 1) in 100 ml of 6N HCI solution. 134 g (1.0 mol) of 4-ethylbenzaldehyde in 800 ml_ of methanol was added to the reaction vessel. The clear solution was stirred for 48 hours, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 250 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 500 ml_ of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven to give 107 g of product, m.p. 244-246°C. The purity was above 99%, based on GC-MS. 1H NMR(300 MHz, DMSO-of6, ppm): 1.14-1.19 (t, 6H), 2.39-2.44 (t, 2H), 2.56-2.63 (q, 4H), 3.41-4.10 (m, 7H), 4.38-4.42 (t, 1H), 4.81-4.83 (d, 1H), 5.07-5.19 (q, 2H), 5.60-5.64 (d, 2H), 5.84-5.89 (m, 1H), 7.19-7.23 (t, 4H), 7.34-7.38 (t, 4H). Examples 3-8 A variety of allyl-substituted dibenzylidene-based (DBS) molecules were synthesized using the procedures similar to the one described in Example 2 above. Structures are shown in Table I, with measured values for melting point. All derivatives had NMR consistent with the indicated structures, and purities of at least 95%, based on GC-MS. A 5L three-necked round bottom flask, equipped with heating mantle, stirrer, nitrogen inlet, and condenser, was charged with 1.8 liters of ethanol, 0.3 liters of water, 300 g (2.00 mole) of D-xylose, 242 g (2.04 mole) of tin powder (-325 mesh), and 242 g (2.00 mole) of allyl bromide. The mixture was stirred and slowly heated to reflux - a significant exotherm and gas evolution was observed at 60°C. The gray suspension was stirred at reflux for three days, in which time the reaction mixture turned an orange/brown color. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was neutralized to pH = 7 by adding approximately 400 ml of 5M NaOH aqueous solution. The suspension was filtered to remove solids, and the yellow solution was decolorized with multiple treatments of activated carbon. The activated carbon was removed by filtration, and the solvent was removed by rotary evaporation to isolate a white syrup. Typical yield (m, 6H), 5.14-5.23 (m, 2H), 5.89 (m, 1 H). The syrup was used without further purification. A two liter reaction kettle, equipped with a stirrer and nitrogen inlet, was charged with 144 g (0.75 mol) of 1-allyl xylitol syrup (product of example 9), 300 mL of water, and 100 ml_ of concentrated (12N) HCI. The mixture was stirred until the 1-allyl xylitol had completely dissolved. 240 g (1.50 mol) of 5',6',7',8'-tetrahydro-2-naphthaldehyde in 400 ml of methanol was added to the reaction vessel. The solution was stirred for two days, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 250 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 8 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 0.5 liters of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven, to give 47.8 g of product, m.p. 210-212°C. The purity was 99%, based on GC-MS. 1H NMR (300 MHz, DMSO-af6, ppm): 1.72 (m, 8H), 2.36-2.51 (t, 2H), 2.71 (m, 8H), 3.54-4.03 (m, 6H), 4.76-4.80 (t, 1H), 5.07-5.17 (q, 2H), 5.56-5.77 (d, 2H), 5.80-5.90 (m, 1H), 7.02-7.06 (m, 2H), 7.11-7.17 (m, 4H). Example 11.12 A variety of allyl DBXs were synthesized using the procedure similar to the one described in Example 2. The structures of example 10 tives had NMR consistent with the indicated structures, and purities of at least 95%, based on GC-MS. Example 13 Bis-1.3:2.4-(3'.4'-Dimethvlbenzvlidenel 1-Propvl Xvlitol 58 g (0.3 mol) of 1-allyl xylitol syrup (Example 8) was dissolved in 60 ml water. About 0.6 g of platinum (5% weight on activated carbon) hydrogen pressure at 60 psi. The reaction was stopped until no hydrogen pressure drop was observed. The solid was filtered. The allyl group of the solution was completely turned into propyl group based on NMR. 100g (0.6 mol) of 3,4-dimethyl benzaldehyde, 500 ml ethanol, and 50 ml_ concentrated HCI (12N) were added into the sugar solution. The clear solution was stirred at room temperature overnight, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 100 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 500 ml of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white of product, m.p. 255-257°C. The purity was above 98%, based on GC- MS. 1H NMR(300 MHz, DMSO-of6, ppm): 0.89-0.93 (t, 3H), 1.30-1.50 (m, 2H), 1.50-1.70 (m, 2H), 2.22 (12H), 3.50-4.05 (m, 6H), 4.78 (1H), 5.56-5.59 (d, 2H), 7.14-7.21 (m, 6H). About 85 g (0.38 mol) of 1-allyl sorbitol syrup ( product of example 1) was dissolved in 85 ml water. 0.8 g of platinum (5% weight on activated carbon) was added and the mixture was hydrogenated at room temperature with hydrogen pressure at 60 psi. The reaction was stopped until no hydrogen pressure drop was observed. The solid was filtered. The allyl group of the solution was completely turned into propyl group based on NMR. 75g (0.54 mol) of 3-methyl-4-fluoro benzaldehyde, 500 ml ethanol, and 56 ml concentrated HCI (12N) were added into the sugar solution. The clear solution was stirred at room temperature overnight, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 100 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 500 ml of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was washed with methanol, dried in a vacuum oven to give 21 g of product, m.p. 253°C. The purity was above 98%, based on GC-MS. 1H NMR(300 MHz, DMSO-c/6, ppm): 0.91-0.95 (t, 3H), 1.40-1.48 (m, 2H), 1.54-1.67 (m, 2H), 2.13-2.25 (6H), 3.42-4.05 (m, 7H), 4.40 (t,1H), 4.82-4.84 (d, 1H), 5.60-5.62 (d, 2H), 7.11-7.16 (m, 2H), 7.30-7.37 (m, 4H). A two liter three-necked round bottom flask, equipped with heating mantle, stirrer, nitrogen inlet, and a condensor, was charged with 600 ml of ethanol, 100 ml of water, 126 g (0.70 mole) of D-glucose, 84 g (0.7 mole) of tin powder (-100 mesh), and 131 g (0.97 mole) of crotyl bromide. The mixture was stirred and slowly heated to reflux - a significant exotherm and gas evolution was observed at 60°C. The gray suspension was stirred at reflux overnight, in which time the reaction mixture turned light yellow. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was filtrated and the solution was stirred with 188 g (1.4 mol) 3,4-dimethyl benzaldehyde overnight, during which time a significant amount of precipitate formed. The yellow solid was isolated by filtration, washed with methanol to give a white powder, m.p. 233-235°C. GC-MS and NMR indicated the desired compound as a mixture of two diastereomers (2:1), of 1-methyl-2-propenyl. Example 16 Bis-1.3.2.4-Dibenzvlidene 2'.3'-Dibromopropvl Sorbitol/ Bis-1.3.2.4-Dibenzvlidene 2'-Bromo-3'-Hvdroxvpropvl Sorbitol An aqueous solution of 90 g allyl sorbitol syrup (Example 1) in 110 g of methanol was titrated with bromine until a light yellow solution. Small amount of NaHS03 was added to give a colorless solution. 1.9 g of p-toulenesulfonic acid monohydrate was added. The clear solution was stirred overnight, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 50 ml of cyclohexane, heated until boiling, filtered, and washed with 2 x 25 ml of boiling cyclohexane. The product was dried in a vacuum oven to give 7.3 g of white powder, m.p. 188-190°C. GC-MS and NMR indicated a mixture of bis-1,3:2,4-dibenzylidene 2',3'-dibromopropyl sorbitol (90%) and bis-1,3:2,4-dibenzylidene 2'-bromo-3'-hydroxypropyl sorbitol (10%). Example 17 Asymmetric benzvlidene/2.4-dimethvlbenzvlidene 1-Ailvl Sorbitol A 2L reaction kettle, equipped with a stirrer and nitrogen inlet, was charged with 111 g (0.50 mol) of 1-allyl sorbitol syrup (product of Example 1) in 280 ml methanol solution. 9.5 g of pTSA, 53 g (0.5 mol) of benzaldehyde and 67 g (0.50 mol) of 2,4-dimethylbenzaldehyde were added to the reaction vessel. The clear solution was stirred for 48 hours, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 250 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 500 ml of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven to give 38.4 g of product, m.p. 234-236°C. Standard analyses of the material indicated that it consisted of a mixture of 1,3-O- (benzylidene):2,4-O-(2,4-dimethylbenzylidene) 1-allyl sorbitol and 1,3-0- (2,4-dimethylbenzylidene):2,4-O-benzylidene 1-allyl sorbitol (85%), 1,3:2,4-bis(benzylidene) 1-allyl sorbitol (5%) and 1,3:2,4-bis(2,4-dimethylbenzylidene) 1-allyl sorbitol (10%). Example 18 Tri-1.3:2.4:5.6-benzvlidene-1 -Allvl Sorbitol 111 g (0.50 mol) of 1-allyl sorbitol syrup (product of Example 1) was dissolved in 111 g of water. The solution was mixed with 50 g of ice. With an ice cooling bath, 90 ml of 93% of sulfuric acid was added slowly so the temperature was below 20°C. 106 g (1.0 mol) of benzaldehyde was added. A dark pink suspension was formed. The reaction was allowed to stand at room temperature overnight. The resultant yellow solid was collected by filtration, neutralized with 10% NaOH solution. The solid was washed with boiling water, then cool methanol to give a white solid with mp of 216-218°C. Two diastereomers (differ only at the methane carbon attached to the oxygen atoms on carbon 5 and 6 of the allyl sorbitol moiety. The methane carbon can either be in the R or S conformation) with ratio 24:76 were detected by GC-MS. 1H NMR(500 MHz, DMSO-c/6, ppm): 2.43-2.45 (t, 2H), 3.95-4.52 (m, 7H), 5.10-5.20 (dd, 2H), 5.72 (s, 1H), 5.79 (s, 1H), 5.89 (s, 1H), 5.86-5.92 (m, 1H), 7.36-7.50 (m, 15H). 13C NMR(125 MHz, DMSO-de, ppm): 34.2, 67.0, 69.6, 70.3, 73.3, 76.9, 77.6, 99.0, 99.1, 102.8, 109.3, 117.6, 126.0, 126.6, 128.0, 128.1, 128.2, 128.6, 128.7, 129.2, 134.0, 137.8, 138.2, 138.4. Example 19 Bis-1.3: 2.4-(3'-bromo-4'-ethvlbenzvlidene)-1-Allyl Sorbitol/ Mono 2. 4-(3'-bromo-4'-ethvlbenzvlidene)-1-Allvl Sorbitol A one liter 3-Neck flask, equipped with a mechanical stirring motor, glass stopper, and gas inlet; was purged with argon for 10 minutes. To this vessel, was added 335.2 mL of a 0.4M methanolic solution of 1-allyl sorbitol (30.07g, 134.1 mmol) (product of example 1) and GO.OOg (281.6 mmol) of 3-bromo-4-ethylbenzaldehyde. After stirring reactants for 10 minutes, 42 ml of HCI (12M) was added to catalyze the reaction. Within two minutes following HCI addition, formation of a precipitate occurred and the solution began to take on a pinkish hue. After 3h of reaction, the pinkish tint has dissipated greatly and the amount of pinkish-white solids had increased. The contents were stirred rapidly and reaction progress was monitored by GC/MS every 8-12 hours. After 48h, during which a significant amount of off-white precipitate had formed, the reaction was quenched with 54.00g (962.5 mmol) postassium hydroxide [pre-dissolved in D.I. H2O], thereby, giving the mixture a final pH of 12-13. The crude solids were isolated by Buchner funnel vacuum filtration and washed with 800 ml of boiling D.I. H20. To remove unreacted sugar, the material was dried overnight, ground to a fine powder, and suspended in 1000 mL of D.I. H2O. The slurried mixture was brought to a boil and stirred for 30 minutes. The solids were captured via Buchner funnel filtration and further washed with boiling D.I. H20 (3 x 1000 mL). To remove residual aldehyde, the aforementioned procedure was repeated utilizing boiling methanol as wash solvent. After drying overnight, GC/MS of the solid material showed a mixture of mono:di benzylidene sorbitols [36.85g; 44.5% crude yield]. To separate this mixture, the crude, white solid was ground to a fine powder, stirred in a boiling 50:50 solvent mixture (CH3OH : D.I. H2O) for 1 h, hot filtered via Buchner funnel filtration and vacuum dried to give 27.99g of a soft, white powder [33.8% isolated yield of the DBS]. Analytical examination revealed this material to be (19a) Bis-1,3, 2,4-(3'-bromo-4'-ethylbenzylidene)-1- allylsorbitol [see below]. Upon standing overnight, a gelled, white precipitate was observed in the wash solvent utilized during final purification of the DBS [50:50; CH3OH : D.I. H2O]. This precipitate was isolated via Buchner funnel vacuum filtration and vacuum dried to yield 7.48g of a white solid [MBS]. Analytical analysis elucidated this material as (19b) Mono 2, 4-(3'-bromo-4'-ethylbenzylidene)-1-allylsorbitol [see below]. '(19a) Analytical results found for Bis-1,3, 2,4-(3'-bromo-4'-ethylbenzylidene)-1-allylsorbitol [C27H3206Br2]: The isolated white powder was dried in a vacuum oven ( give 27.99 g of a soft, white powder, m.p. 268.2-268.6°C [under argon]. Purity was >98.3% based on GC-MS. 1H NMR (500 MHz, DMSO-d6) 6 ppm): 1.15 (dt, 6H, -ChbCHs); 2.42 (tdd, 2H, -allylic methylene); 2.70 (dq, 4H, -CHaCHg); 3.44 (b, m, 1H); 3.61 (b, dq, 1H); 3.74 (b, m, 1H); 3.84 (b, d, 2H); 4.10 (b, m, 2H); 4.43 (t, 1H, 2° -OH); 4.90 (d, 1H, 1°- OH); 5.14 (b, qm, 2H, -CH=CH2); 5.63 (s, 1 H, acetal); 5.67 (s, 1 H, acetal) 5.88 (m, 1H, -CH=CH2); 7.38 (b, m, 4H, aromatic); 7.58 (b, s, 1 H, aromatic) 7.62 (b, d, 1 H, aromatic). 13C NMR (500 MHz, DMSO-d6, 6 ppm): 14.25 (-CH2CH3); 28.50 (-CH2CH3); 34.29 (-allylic); 62.60; 67.73; 68.86; 70.84; 77.03; 77.53; 97.83 (acetal); 97.94 (acetal); 117.49 (_CH=CH2); 122.81; 122.88; 125.64; 125.78; 129.49; 129.62; 129.72; 129.89; 134.13 (-CH=CH2); 138.33; 138.45; 142.91; 142.97. (19b) Analytical results found for Mono-2, 4-(3'-bromo-4'- ethylbenzylidene)-1-allylsorbitol [C18H25O6Br]: The isolated white powder was dried in a vacuum oven ( give 7.58 g of a soft, white powder, m.p. 199.8-200.5°C [under argon]. Purity was >96% [contained (500 MHz, DMSO-de, 6 ppm): 1.16 (t, 3H, -Ch^CHa); 2.10 (m, 1H, -allylic methylene); 2.40 (b, m, 1H, -allylic methylene); 2.70 (q, 2H, -CHaCHg); 3.41 (m, 1H); 3.47 (b, d, 1H); 3.57 (b, m, 1H); 3.62 (b, d, 1H); 3.74 (b, dm, 2H); 3.88 (b, d, 1H); 4.34 (d, 1H, 1 ° -OH); 4.40 (t, 1H, 2° - OH); 4.70 (d, 1H, 1° -OH); 4.78 (d, 1H, 1° -OH); 5.03 (b, m, 2H, - CH=CH2); 5.50 (s, 1H, acetal); 5.91 (b, m, 1H, -CH=CH2); 7.36 (b, m, 2H, aromatic); 7.67 (b, d, 1H, aromatic). 13C NMR (500 MHz, DMSO-d6, 6 ppm): 14.26 (-CH2CH3); 28.49 (-CH2CH3); 37.89 (-allylic); 60.51; 62.70; 67.15; 69.15; 79.54; 82.33; 98.84 (acetal); 116.33 (-CH=CH2); 122.88; 125.99; 129.42; 130.10; 135.92 (-CH=CH2); 138.56; 142.87. Example 20 12-Hvdroxv Stearic Acid, and Lauryl Sulfuric Acid Na In a clean 250 ml one-neck flask with a stir bar, was charged with 9.50 g of Bis-1,3;2,4-(4'-ethylbenzylidene) 1-Allyl Sorbitol (Example 2), 0.250 g of 12-hydroxy stearic acid, 0.250 g of lauryl sulfuric acid Na, and 60 g of methanol. The mixture was heated to reflux for one hour with stirring. The reaction was allowed to cool to room temperature. The methaol was rotor evaporated, then dried in a vacuum oven at 80°C for 2 hours, to give 9.62 g of product as a white solid. M.P. 203-204°C. Example 21 Bis-1.3:2.4-(3'.4' dimthvlbenzvlidene) 1-Methyl Sorbitol 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone (21 a) 27 g of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (50 mmol) was dissolved in 153 ml of DMSO to form a clear solution. 102 ml of acetic anhydride was added dropwise. The resultant clear solution was allowed to stir at room temperature overnight. After 17 hours, GC-MS showed the lactone was gone and a new compound was observed. The yellow solution was poured into 600 ml_ of water and sat in a separation funnel overnight. The precipitated oil was passed through a silica gel column, eluted first with cyclohexane then gradually increasing polarity by adding acetone until the final eluent was cyclohexane: acetone = 2:1. The appropriate portions were collected and evaporated to give a pale syrup. 25.2 g, yield: 94%. IR (v cm'1) 2867, 1752. 3,4,5,7-Tetra-O-benzyl-1-deoxy-D-g/uco-heptulopyranose (21 b) 18 g (33 mmol) of 21 a was dissolved in 200 ml of anhydrous THF under nitrogen. Cooled to -78°C. 45 ml_ of MeLi (1.6 M, 72 mmol) was added by a syringe. After 1 hour at -78°C, the reaction was quenched by a solution of 7 g of NH4CI in 200 ml_ of H20. TLC showed no starting material left, while a new spot corresponding to the product appeared. The mixture was extracted by 3 X 150 mL of ethyl acetate, washed by brine, dried over Na2SO4. After evaporation, a thick pale yellow oil was obtained which was turned into a white solid (17.6 g, 95% yield) with a melting point of 92-93°C. 300 MHz 1H NMR(CDCI3) 6: 1.41 (s, 3H, CH3); 2.58 (s, 1H, OH); 3.35-3.38 (d, 1H); 3.65-3.72 (m, 3H); 3.93-3.99 (m, 2H); 4.50-4.95 (m, 8H, 4-CH2), 7.14-7.36 (m, 20H). 13C NMR (CDCI3) 6: 26.59, 68.81, 71.55, 73.42, 74.85, 75.58, 75.68, 78.42, 83.18, 83.63, 97.36, 127.58, 127.65, 127.74, 127.82, 127.84, 127.91, 128.28, 128.32, 128.36, 128.41, 137.87, 138.21, 138.25, 138.64. 1,3,4,5-Tetrakis-benzyloxy-heptane-2,6-diol (21 c+21 c') To a clear solution 5.54 g (10 mmol) of 21 b in 60 mL of THF, 0.5 g (12.5 mmol) of 95% LiAIH4 was added. The mixture was allowed to stir under an ice-bath for 4 hours. TLC showed all starting material was gone with two very close new spots appearing. The reaction was carefully quenched with 2N HCI, then extracted with ethyl acetate. The combined organic phase was washed with aqueous NaHCO3, then brine, and dried over sodium sulfate. A colorless syrup (5.5 g, 99% yield) was obtained after solvent was evaporated. The ratio of 1.048-1.069 ppm (doublet, 21c): 1.170-1.191 ppm (doublet, 21c') was45%:55%, based on NMR. Heptane-1,2,3,4,5,6-hexaol (21 d+21 d') To a solution of 2.4 g (4.3 mmol) of 21 c in 100 mL of ethanol, 0.6g of 5% Pd-C was added. The mixture was hydrogenated at initial hydrogen pressure at 63 psi. After 6 hours, the catalyst was filtered off and washed with methanol-water. The combined solution was evaporated to give a white solid. 0.80 g, yield: 95%. 300 MHz 1H NMR(D2O) 6: 1.186-1.237 (two doublet, 3H), 3.537-3.988 (m, 7H). Bis-1,3:2,4-(3',4' dimthylbenzylidene) 1 -Methyl Sorbitol (21) To a solution of 4.65 g (24 mmol) of 21 d+21 d' in 100 mL of acetic acid was added 4.77 g (36 mmol) of 3,4-dimethyl benzaldehyde. The mixture was allowed to stir at room temperature overnight. The resultant gel was neutralized by KOH-H2O. The white solid (4.2 g) was collected by filtration and suspended in boiling water. The suspension was filtered hot and the solid was washing with 7X100ml boiling water. The solid was then suspended in 50 mL of boiling methanol and filtered again. 2.30 g of dry, white solid was obtained with yield of 25%. GC-MS showed the purity was 98.3%. Melting point: 259-261 °C. 300 MHz 1H NMR(DMSO-d6) 6: 1.23-1.25 (doublet, 3H), 2.21-2.23 (m, 12 H), 3.40-4.80 (m, 9H), 5.55-5.59 (doublet, 2H), 7.10-7.22 (m, 6H). 5 Example 22 Compositions containing various levels of the acetal of examples 2-21, coadditives (0.05 wt. % Irganox 1010, 0.1 wt. % Irgafos 168, and 0.08 wt. % calcium stearate) and the balance polypropylene homopolymer or polypropene random copolymer (3% ethylene content) were dry blended in a mechanical mixer, extruded through a single screw extruder at 240°C and pelletized. Plaques were prepared (1.27 mm thick) by injection molding the pellets at 220°C. The Tc and haze were measured, and the results are reported in Table 2. Millad 3988® is a registered trademark of Milliken and Company of Spartanburg, South Carolina. Millad 3988® is a commercially distributed clarifying agent product that employs bis(3,4-dimethylbenzylidene sorbitol)("DMDBS"), as shown and described in United States Patent No. 5,049,605. TABLE 2: Percent Haze Measurements for Various Compounds Polymer Example Concentration (ppm) Tc (°C) Haze(%) RCPPP (Control) 101.2 44.3 RCPPP Millad 3988® 2500 113.6 7.2 RCPPP 2 6000 115.1 4.9 RCPPP 3 3500 109.4 8.8 RCP PP 4 5000 113.1 10.5 RCPPP 5 5000 107.8 17.2 RCPPP 6 2000 105.2 23.3 RCPPP 8 5000 109.0 8.9 RCPPP 10 5000 109.6 11.3 10 RCPPP 11 5000 111.9 21.8 RCPPP 12 5000 110.8 19.9 RCPPP 13 5000 109.5 8.4 RCPPP 14 5000 111.5 5.6 RCPPP 15 5000 105.8 8.8 RCPPP 16 3000 107.0 18.9 RCPPP 19a 5000 113.1 6.5 RCPPP 19b 5000 110.6 17.3 RCPPP 20 5000 114.6 5.7 RCPPP 21 2500 109.2 23.6 PP (Control) 116.6 58.1 PP Millad 3988® 2500 124.0 11.7 PP 2 5000 125.2 7.5 In some applications of the invention, the nucleating agent composition may be added to the polymer resin at a concentration of from about 0.005 to about 3 weight percent. In other applications, a concentration of between about 0.01 and about 1 weight percent may be employed. In other applications, a concentration of between about 0.025 and about 0.5 weight percent of the composition is useful. Concentrates of up to 50 weight percent of the nucleating agent in resin may also be prepared for blending with additional resin prior to molding. Typically, concentrates containing 33 weight percent or less of the nucleating agent in resin are used commercially. The resin may be extruded a second time immediately before being processed into a finished article by, for example, injection molding, extrusion blow molding, injection blow molding, stretch blow molding, compression molding, rotational molding, profile extrusion, sheet extrusion, thermal forming, film extrusion, and film extrusion with orientation. Gel Formation and Testing Solid gels also were produced comprising the inventive substituted-alditol derivatives through recognized, simple methods. In particular, specific organic solvents were combined with the additives in certain concentrations and mixed thoroughly. The resultant mixture was then heated to a temperature between about 170°F (77°C) and 300°F (149°C), as indicated below, under agitation for between 5 and 120 minutes. The resultant solution was then poured into a mold to produce a gel stick. The solvents listed are not intended to be exhaustive as to the potential types which may be utilized to form gels with the inventive substituted-alditol derivatives, and thus are merely listed as preferred solvents for such purposes. The examples below were analyzed empirically and by touch to determine if a gel actually formed and the hardness properties as well as any formed gels. Results are reported in Table 3. Table 3: Gel Sample Data -.1 Sample - " Number •&„" ^s^ „ -" ; SOLVENT ' ->! V" i ,r. . s : - ADDITIVE .; . 'l'_ (Example #:above) s^f^ B DBS Corfc {Weight^ I>;a3eTs\|4V vFbrMatforB ..^ftTflf'r- a. '-J* .-* ~ ^1^ ' ~£&- ••• •ff^sf-- > ^,~v*>-s G'efpfiajfSeir:"'" : ffiard/§bft}:":::- 1 1,2-Propanediol 2 1 Y Hard 2 1,3-Propanediol 2 1 Y Hard 3 2-Chlorotoluene 2 1 Y Soft 4 Toluene 2 1 Y Soft 5 Benzonitrile 2 1 Y Soft 6 1,2-Propanediol 13 1 Y Hard 7 2-Chlorotoluene 13 1 Y Hard 8 Benzonitrile 2 3 Y Hard 9 1,2-Propanediol 2 3 Y Hard 10 1,3-Propanediol 2 3 Y Hard 11 2-Chlorotoluene 2 3 Y Soft 12 1,2-Propanediol 13 3 Y Hard 13 2-Chlorotoluene 13 3 Y Hard 14 1,2-Propanediol 18 1 Y Hard 15 1,3-Propanediol 18 1 Y Hard Thus, the inventive substituted-alditol derivatives provide excellent gelling capabilities for solvents, depending upon their concentration without the target solvents. It is understood by one of ordinary skill in the art that the present discussion is a description of exemplary embodiments only, and is not intended as limiting the broader aspects of the present invention, which broader aspects are embodied in the exemplary constructions. The invention is shown by example in the appended claims. WE CLAIM: 1. A diacetal compound conforming to the structure: (Formula Removed) wherein; n is 0,1 or 2 Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and R is selected from the group consisting of alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides, wherein the hydroyl alkyls are selected from the group consisting of-CHOHCHOHCH2OH, where X'' is a halide group. 2 The compound as claimed in claim 1 wherein n=0. 3. The compound as claimed in claim 1 wherein n=l. 3. The compound as claimed in claim 1 wherein n = 2. 4. The compound as claimed in claim 1 wherein R is allyl. 5. The compound as claimed in claim 1 wherein R is propyl. 7. A polyolefin-containing composition having therein the compound as claimed in claim 1. 8. The compound as claimed in claim 1 wherein said R is selected from one of the following: (Formula Removed) wherein X, X1, X", and X'", if present, are independently selected halide groups, 9. The compound as claimed in claim 8 wherein Ar1 and Ar2 are independently selected from the group of substituted benzaldehydes including: (Formula Removed) 10. The compound as claimed in claim 9 wherein said Ar1 and AR2 are both 4- propylbenzaldehyde. 11. A formed or molded polyolefin article comprising the compound as claimed in claim 1. 12. The compound as claimed in claim 1 with structure: (Formula Removed) wherein n is 1 ; R is an alkenyl or alkyl group; R1, R2, R3, R4, and R5 each are independently selected from the group consisting of hydrogen, alkyls, alkynyls, alkoxy, carboxy, halogens, and phenyls. 13. The compound as claimed in claim 12 wherein said R is selected from one of the following: (Formula Removed) 14. The compound as claimed in claim 13 wherein R comprises (Formula Removed) 15. The compound as claimed in claim 13 wherein R comprises -CH2CH2CH3. 16. The compound as claimed in claim 13 wherein one of said R1, R2, R3, R4 and R5 comprises an alkyl, 17. An acetal of a substituted alditol conforming to the structure (III) (Formula Removed) made by reacting (a) and (b): (a) a substituted alditol compound (Formula Removed) wherein n is 0, 1 or 2; and R is selected from the group consisting of alkenyl, alkyl, alkoxy, and alkylhalides and (b) at least one mole of substituted or unsubstituted benzaldehyde per mole of substituted aldlitol compound, said benzldehyde being as shown: (Formula Removed) wherein R1, R2, R3, R4 and R5 each are independently selected from the group consisting of: hydrogen, alkyls, fluorocarbons, alkenyls, alkenyls, alkoxy, carboxy, halogens, cyclic groups, and phenyls. 18. A method of providing a nucleated or clarified polyolefin composition, the method comprising in part combining with said polyolefin composition the compound claimed in claim 1 having compound having the structure: (Formula Removed) wherein: n is 0, 1 or 2; AR1 and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and R is selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides. 19. The method as claimed in claim 18 wherein said R is selected from one of the following: (Formula Removed)

Full Text

Title of the Invention
ACETAL-BASED COMPOUNDS AND METHODS Background of the Invention
Derivatives of acetals of polyhydric alcohols are useful in several
applications, including for example as nucleating agents for polymer
resins, and as gelling and thickening agents for organic liquids. Dibenzylidene sorbitol type (DBS) compounds are known for use in such applications.
The use of nucleating agents to reduce the haze in articles
manufactured from crystalline polyolefin resins is known in the art.
Representative acetals of sorbitol and xylitol, which have been employed as clarifying agents, are described in several patents, including for example: Hamada, et al., United States Patent No. 4,016,118, dibenzylidene sorbitols; Kawai, et al., United States Patent No.
4,314,039, di(alkylbenzylidene) sorbitols; Mahaffey, Jr., United States
Patent No. 4,371,645, di-acetals of sorbitol having at least one chlorine or bromine substituent; Kobayashi, et al., United States Patent No. 4,954,291, distribution of diacetals of sorbitol and xylitol made from a mixture of dimethyl ortrimethyl substituted benzaldehyde and
unsubstituted benzaldehyde. Another reference, United States Patent -
No. 5,049,605 to Rekers et al. discloses bis(3,4-dialkylbenzylidene) sorbitols, including substituents forming a carbocyclic ring.
Substitution of various groups upon the benzyl ring portion(s) of DBS-based compounds may have a significant impact upon the
suitability of such compounds as nucleating or clarifying agents. A
significant amount of work in the past has been directed to modifying the substitution of the benzylidene ring substituent(s). However, efforts still

are underway to develop other compounds that are likely to afford reduced haze (and corresponding greater clarity) when used as plastic additives in polymer compositions.
The chemical arts often are unpredictable. Changing any portion
or substituted group in these particular types of compounds may have a
significant impact upon the performance and utility of the compound. This invention recognizes important new compositions that have not been known before, and may be quite useful as plastic additives, or as gelling agents, thickeners, or for other purposes.
Detailed Description of the Invention
Reference now will be made to the embodiments of the invention, one or more examples of which are set forth below. Each example is provided by way of explanation of the invention, not as a limitation of the invention. It will be apparent to those skilled in the art that various
modifications and variations can be made in this invention without
departing from the scope or spirit of the invention.
A polyolefin additive composition is disclosed herein. In some applications, the polyolefin additive composition provides improved transparency to plastic polymer compositions when added to such
compositions. In some applications, the additive composition will be
advantageous when used in connection with polypropylene, although various applications in connection with other polymers are within the scope of the invention.
Olefin polymers which can be nucleated by such compositions
(and whose transparency may be improved according to the practice of
the invention) include polymers and copolymers of aliphatic mono-olefins containing from 2 to about 6 carbon atoms, which have an average

molecular weight of from about 10,000 to about 2,000,000, preferably from about 30,000 to about 300,000, such as polyethylene, including linear low density polyethylene, low density polyethylene and high density polyethylene, polypropylene, crystalline ethylene/propylene copolymer (random or block), poly(l-butene) and polymethylpentene.
Examples of other thermoplastic polymer resins which may be nucleated with the disclosed acetal compounds include polyester, poly(ethylene terephthalate) (PET) and poly(butylene terephthalate) and polyamide, including nylon 6 and nylon 6,6, poly(phenylene sulfide), syndiotactic polystyrene and polyketones having carbonyl groups in their backbone.
The composition may comprise a polymer selected from aliphatic polyolefins and copolymers containing at least one aliphatic olefiri and one or more ethylenically unsaturated comonomers and at least one mono-, di-, ortri-acetal of substituted alditol (such as allyl-sorbitol, propyl-sorbitol, allyl-xylitol, propyl-xylitol and the like).
The mono-, di-, ortri-acetal of substituted alditol may include a composition as described below. For example, and not by way of limitation, a substituted alditol as in Formula (I), which is combined with at least one mole of benzaldehyde selected from the compounds with Formula (II), as shown below.

For Formula (I): n is 0, 1, or 2; and
R is independently selected from non-hydrogen groups including alkenyl groups (such as allyl), alkyl groups, alkoxy groups, hydroxyl alkyl groups, alkyl-halide groups.

For Formula (II), R-i, Ra, Rs, R An acetal compound may be formed in one particular embodiment of the invention by the process of: (a) reacting a polyhydric alcohol with an alkenyl molecule to form a first compound; and (b) reacting in a condensation reaction said first compound with an aromatic aldehyde to form an acetal compound. However, the invention may be practiced in other ways as well. The acetal compound thus formed may be a mono-

, di-, or tri- acetal, but in many cases it has been found that a di-acetal is particularly useful. The acetal compound may comprise an allyl in one particular embodiment of the invention, as herein further described.
In some applications, such a reaction product or resulting composition is a di-acetal (and thus the result of a 1:2 molar ratio reaction between the alditol and benzaldehyde). A composition may be provided having the structure of Formula (III), below. A single acetal, or a triacetal, could also be provided in the practice of the invention, but one particular di-acetal composition is shown below:

In the composition, n may be 0,1, or 2; and An and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups. Furthermore, R may be selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides. R may

comprise an alkenyl, and in some particular embodiments of the
invention, an allyl has been found to work quite well for the R group.
It should be appreciated that the R group stereochemistry is not
defined, and the invention is not limited to any particular R group
stereochemistry, such that all chemical structures provided herein shall
cover any isomers that occur due to stereoisomers of the carbon atom to which R is attached.
It should be appreciated with regard to the composition set forth above that while only the 1,3; 2:4 isomer is represented (i.e. the
numbered carbons on the sorbitol chain which form the two acetals), this
structure is provided for convenience and illustration only and the invention is not limited to only isomers of the 1,3: 2,4 type, but may include any and all other isomers as well, including also isomers of the 1:3; 4:6 and 2,4:3,5 type, as examples.
The diacetals, triacetals, and monoacetals of the invention may
be condensation products of substituted alditols, such as (but not limited to) allyl-sorbitol, propyl-sorbitol, 1-methyl-2-propenyl sorbitol, allyl-xylitol, propyl-xylitol, and a (substituted) benzaldehyde. Examples of suitable (substituted) benzaldehydes include benzaldehyde, 4-
ethylbenzaldehyde, 4-isobutylbenzaldehyde, 4-fluoro-3-
methylbenzaldehyde, 5,6,7,8-tetrahydro-2-naphthaldehydebenzylidene, 3-methylbenzaldehyde, 4-propylbenzaldehyde, 4-butylbenzaldehyde, 4-methoxybenzaldehyde, 3-chlorobenzaldehyde, 3,4-dimethylbenzaldehyde, 3,5-difluorobenzaldehyde, 3-fluorobenzaldehyde,
4-fluorobenzaldehyde, 3-bromo-4-fluorobenzaldehyde, 3-methyl-4-
methoxybenzaldehyde, 2,4,5-trimethylbenzaldehyde, 4-chloro-3-fluorobenzaldehyde, 4-methylbenzaldehyde, 3-bromobenzaldehyde, 4-

methoxybenzaldehyde, 3,4-dichlorobenzaldehyde, 4-fluoro-3,5-
dimethylbenzaldehyde, 2,4-dimethylbenzaldehyde, 4-
bromobenzaldehyde, 3-ethoxybenzaldehyde, 4-allyloxybenzaldehyde,
3,5-dimethylbenzaldehyde, 4-chlorobenzaldehyde, 3-
methoxybenzaldehyde, 4-(trifluoromethyl)benzaldehyde, 2-
naphthaldehyde, 4-isopropylbenzaldehyde, 3,4-diethoxybenzaldehyde, 3-bromo-4-ethoxybenzaldehyde, piperonal, 3,4-dimethoxybenzaldehyde, 4-carboxybenzaldehyde, 3-hex-1-ynylbenzaldehyde, and 2- include 1,3:2,4-bis(4-ethylbenzylidene)-1-allyl-sorbitol, 1,3,2,4-bis(3'-
methyl-4'-fluoro-benzylidene)-1 -propyl-sorbitol, 1,3,2,4-bis(5',6',7',8'-tetrahydro-2-naphthaldehydebenzylidene)-1 -allyl-xylitol, bis-1,3,2-4-(3',4'-dimethylbenzylidene)-1 "-methyl-2"-propyl-sorbitol, 1,3,2,4-bis(3',4'-dimethylbenzylidene)-1 -propyl-xylitol.
The di-acetals and mono-acetals of the present invention may be
prepared by a variety of techniques, some of which are known in the art. Generally, such procedures employ the reaction of one mole of substituted alditol (such as allyl-sorbitol, propyl-sorbitol, allyl-xylitol, mole of aldehyde (for monoacetals), or with 3 moles of aldehyde (for
triacetals) in the presence of an acid catalyst (inorganic acid such as hydrochloric acid or organic acid such as p-toluenesulfonic acid (pTSA)). Further, an organic solvent is employed that is miscible with water (such temperature.
In the practice of the invention, it is possible to have any number of DBS moities on the structure. It is common to have one, two, or

three DBS (i.e. aryl-containing) moities on the hydrocarbon backbone. Below are several examples that can be employed in the method of nucleating a polyolefin composition. That is, one may employ one or more of the following:

wherein:
Ar, An and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and
R is selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, alkyl-halides and derivatives thereof.
Also, co-additives may be combined with said polyolefin composition. Examples of co-additives that can be used are set forth below in (1) - (3). Example 21 below shows yet another example of a co-additives lauryl sulfuric acid Na, that may be employed. Many other examples could be employed, and the co-additives below could be used with essentially any of the nucleating agent structures or compositions disclosed herein. Also, more than one co-additive set forth below could be employed, and the amount or concentrion employed would vary for a given application.

(1) Co-additives for inhibiting migration of odor and taste.
Alkali metal salts of amino acids (at least one amino acid chosen
from the following: glycine, L-alanine, L-phenyl-aianine, L-isoleucine, L-
valine, L-leucine, L-proline, L-arginine, L-asparatic acid, L-cystine, L-
glutamic acid, L-serine, L- histidine, L-tryptophan, L-lysine, L-threonine,
L-methionine, DL-ethionine, L-cysteine, L-tyrosine, L-asparagine, L-
glutamine, L-norvaline, and L-a-amino butyric acid.) and 0.1 to 100 parts
by weight of at least one fatty acid with 8-32 carbon atoms (octane acid,
capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, 12-
hydroxy stearic acid, behenic acid, montan acid, oleic acid, linoleic acid,
ereo-stearic acid, ricinoleic acid, and erucic acid ).
(2) Co-additives for inhibiting migration of odor and taste and
depression the melting point of DBS: A: At least a saturated or
unsaturated aliphatic alcohol with 6-32 carbon atoms (for example: lauric
alcohol). B: and at least a saturated or unsaturated aliphaltic carboxylic
acid with 8-32 carbon atoms having at least one hydroxy group within the molecule (for example: 12-hydroxy stearic acid), C: at least one type chosen from the following groups: lithium salt, sodium salt, or potassium salt of a saturated or unsaturated fatty acid with 8-32 carbon atoms that
may have at least one hydroxyl group within the molecule, or D: at least
one type sulfuric acid ester salt chosen from the following group: lauryl sulfuric acid salt, stearyl sulfuric acid salt, oleyl sulfuric acid salt, and polyoxyethylene stearyl ether sulfuric acid salts.

(3) Co-Additives having a granular or powdery diacetal
composition: wherein the binder is selected from the group consisting of
monocarboxylic acids, polycarboxylic acids, partial salts of
polycarboxylic acids, esters of phosphoric acid and at least one member
selected from the group consisting of C1-C30 monohydric aliphatic
alcohols and C2-C30 polyhydric aliphatic alcohols, esters of phosphorous acid and at least-one member selected from the group consisting of C1-C30 monohydric aliphatic alcohols and C2-C30 polyhydric aliphatic alcohols, esters of phosphoric acid and at least one
member selected from the group consisting of C6-C30 monohydric
aromatic alcohols and C6-C30 polyhydric aromatic alcohols, esters of phosphorous acid and at least one member selected from the group consisting of C6-C30 monohydric aromatic alcohols and C6-C30 polyhydric aromatic alcohols, taurine, salts of sulfuric acid ester, sulfonic
acid salts, salts of phosphoric acid ester and mono-, di- and tri(C6-C30
fatty acid) aluminum salts, each of which may have, in the molecule, at least one bond or functional group selected from the group consisting of an ether bond, an ester bond, a thioether bond, an amide bond, a halogen atom, amino group, hydroxyl groups, a heterocyclic group and
carbonyl group.

Synthesis Methods for Di-Acetals
One method that can be employed to prepare di-acetals of the invention is described in United States Patent No. 5,106,999 to Gardlik et al., which is hereby incorporated by reference.
Methods to prepare and synthesize the carbohydrates of varying
chain length are disclosed in Kim, Gordon, Schmid, and Whitesides, Tin and Indium Mediated Allylation in Aqueous Media: Application to Unprotected Carbohydrates, J. Org. Chem, 5500-5507, 58 (1993) and in Whiteside, Journal of the American Chemical Society, 113, 6674-6675
(1991). Whiteside has suggested the reaction of glucose with allyl
bromide/tin.
One reaction method that may be employed in the preparing starting materials for the synthesis of compositions needed in the practice of the invention are shown below, in which an allyl group may
be added to a carbohydrate. The reaction scheme illustrated is merely
one example, and similar reactions can be carried out for carbohydrates having more or less carbon groups in the chain.

HO
OH BrCH2CH=CH2, Sn OH-C —
1 ^ — C— OH
—OH —OH
HO

—OH —OH
—OH —OH
CH2OH , ikUOH
1,2,3-trideoxy-D-glycero-D-ido-nonenitol

1,2,3-trideoxy-D-glycero-D-gulo-nonenitol

OH—C—
-OH

—C—OH -OH

HO

HO

-OH

-OH

CH2OH 1,2,3-trideoxy-D-ido-octenitol

CH2OH

1,2,3-trideoxy-D-gulo-octenitol

In the practice of the invention, an acetal compound formed by the process of: (a) reacting a carbohydrate and an alkenyl group to form a first compound; and (b) reacting in a condensation reaction said first compound with an aromatic aldehyde to form an acetal compound. In some applications, the alkenyl group comprises an allyl.
It has been discovered in the course of work leading to one embodiment of the invention herein that allyl bromide/tin chemistry as

illustrated above is one manner of synthesis for a carbohydrate
hydrocarbon chain that can be used as one step in a sequence of
reactions to unexpectedly provide significant advantages and valuable
compositions. This general reaction pathway may be used in various
forms to synthesize carbohydrates in the manufacture of the
compositions of the invention. One embodiment of the invention relates to the use of carbohydrate synthesis reactions in combination with other acetal formation reactions to prepare compositions of the invention.
Substituted sorbitol diacetals, triacetals, and monoacetals may be
prepared. These structures contain mixtures of any correlated types of
acetals (such as the related di-, tri-, and/or mono-acetals of the target
acetal). Although it may not always be necessary to remove these
impurities (particularly if they are present in very low proportions) prior to
incorporation of the di-acetal, triacetal or monoacetal into the target
polyolefin, it may be desirable to do so and such purification may serve
to enhance the transparency of the resin produced thereby.
Purification of a di-acetal may be accomplished, in one
embodiment of the invention, by removal of any present tri-acetals by
the extraction thereof with a relatively non-polar solvent. As one non-
limited example, by removal of the impurities, the product may be
purified so that the amount of di-acetal in the additive composition
contains at least about 95 percent and even up to 98 percent di-acetal or
more, depending upon the application.
A more complete synthesis pathway is shown below, which is
merely illustrative, and not limited to only those species or reactions
shown:

CH2OH
OH

HO— C
Q RrrH-,rH=rFU Sn
r > OH
OH
3H Ul 1

VVWOH EtOH-H")O Mn

\-ir\

OH
C OH

)H Ul 1

UM
CH2OH

ArCHO

Generic Structure of a Synthesized Acetal-based Composition

Many different substituted benzyl groups may be employed for Ar-i and Ar2
in the practice of the invention, as shown by several representative examples
in Table 1, which were synthesized and tested as shown in the Examples listed herein. Substituted groups for An and/or Ar2 are not limited to only

those found in Table 1. For example, Table 1 reports various compositions
for which n= 0 and where n=1 for various substituted An, and Ar2 groups.
When n = 0, the xylitol moity is employed. When n = 1 , the sorbitol moity is
employed. Although n = 2 compounds are not reported in Table 1 , such
compounds are within the scope of the invention, and are within the
teachings provided herein. There is no practical limit to what may be substituted in such compositions, so long as they are chemically possible. However, it has been found that certain substituted groups on this compound provide enhanced properties.
In the practice of the invention, R may be selected from a wide variety of
compounds, including without limitation and by way of example:
-CH2CH2CH3; -CH2CH2CH2CH3;
-CH2CH=CH2; -CH(CH3)CH=CH2;
-CH2CH-X-CH2-X' ; -CH2CH2.X"-CH2-CH3 ;
-CH2CH-X'"-CH2OH; -CH-OH-CH-OH-CH2.OH. With regard to the compounds above, X, X1, X" , and X1" comprise independently selected halide groups in those selected compounds, if they are employed.
The allyl species (-CH2CH=CH2) is sometimes particularly advantageous,
and several such species were synthesized and reported along with others in
A 3L, three-necked round bottom flask, equipped with heating
mantle, stirrer, nitrogen inlet, and condensor, was charged with 900 mL
of ethanol, 150 ml of water, 180 g (1.00 mole) of D-glucose, 119 g (1.00 mole) of tin powder (-100 mesh), and 121 g (1.00 mole) of allyl bromide. The mixture was stirred and slowly heated to reflux - a significant exotherm and gas evolution was observed at 60°C. The gray
suspension was stirred at reflux for two days, in which time the reaction
mixture turned an orange/brown color. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was neutralized to pH = 7 by adding approximately 200 ml of 5M NaOH aqueous solution. The suspension was filtered to remove solids, and
the yellow solution was decolorized with multiple treatments of activated
carbon. The activated carbon was removed by filtration, and the solvent was removed by rotary evaporation to isolate a white syrup. Typical yield was 200g with threo-erythro ratio of 1:6, based on GC-MS. The syrup was used without further purification.
Pure erythro isomer could be obtained by hydrolysis of any of the
example 2-8. 1H NMR (500 MHz, D2O, ppm): 2.34-2.37 (m, 2H), 3.63-3.95 (m, 7H), 5.13-5.20 (m, 2H), 5.88-5.89 (m, 1H). 13C NMR (125 MHz, D2O, ppm): 38.32, 63.69, 70.74, 71.14, 71.80, 71.92, 74.58, 118.60, 135.72.

A 2L reaction kettle, equipped with a stirrer and nitrogen inlet, was
charged with 111 g (0.50 mol) of 1-allyl sorbitol syrup (product of
Example 1) in 100 ml of 6N HCI solution. 134 g (1.0 mol) of 4-ethylbenzaldehyde in 800 ml_ of methanol was added to the reaction vessel. The clear solution was stirred for 48 hours, during which time a significant amount of white precipitate formed. The powder was isolated
by filtration and washed with 250 ml of 1M NaOH aqueous solution. The
powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in
500 ml_ of cyclohexane, heated until boiling, filtered, and washed with 2
x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven to give 107 g of product, m.p. 244-246°C. The purity was above 99%, based on GC-MS. 1H NMR(300 MHz, DMSO-of6, ppm): 1.14-1.19 (t, 6H), 2.39-2.44 (t, 2H), 2.56-2.63 (q, 4H), 3.41-4.10 (m, 7H),
4.38-4.42 (t, 1H), 4.81-4.83 (d, 1H), 5.07-5.19 (q, 2H), 5.60-5.64 (d, 2H),
5.84-5.89 (m, 1H), 7.19-7.23 (t, 4H), 7.34-7.38 (t, 4H).
Examples 3-8
A variety of allyl-substituted dibenzylidene-based (DBS) molecules
were synthesized using the procedures similar to the one described in
Example 2 above. Structures are shown in Table I, with measured values for melting point. All derivatives had NMR consistent with the indicated structures, and purities of at least 95%, based on GC-MS.

A 5L three-necked round bottom flask, equipped with heating
mantle, stirrer, nitrogen inlet, and condenser, was charged with 1.8 liters of ethanol, 0.3 liters of water, 300 g (2.00 mole) of D-xylose, 242 g (2.04 mole) of tin powder (-325 mesh), and 242 g (2.00 mole) of allyl bromide. The mixture was stirred and slowly heated to reflux - a significant
exotherm and gas evolution was observed at 60°C. The gray
suspension was stirred at reflux for three days, in which time the reaction mixture turned an orange/brown color. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was neutralized to pH = 7 by adding approximately 400 ml of 5M NaOH
aqueous solution. The suspension was filtered to remove solids, and
the yellow solution was decolorized with multiple treatments of activated carbon. The activated carbon was removed by filtration, and the solvent was removed by rotary evaporation to isolate a white syrup. Typical yield (m, 6H), 5.14-5.23 (m, 2H), 5.89 (m, 1 H). The syrup was used without
further purification.

A two liter reaction kettle, equipped with a stirrer and nitrogen inlet,
was charged with 144 g (0.75 mol) of 1-allyl xylitol syrup (product of example 9), 300 mL of water, and 100 ml_ of concentrated (12N) HCI. The mixture was stirred until the 1-allyl xylitol had completely dissolved. 240 g (1.50 mol) of 5',6',7',8'-tetrahydro-2-naphthaldehyde in 400 ml of
methanol was added to the reaction vessel. The solution was stirred for
two days, during which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 250 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 8 with a small amount of NaOH. The
suspension was heated to boiling, then filtered. The white powder was
washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was then stirred in 0.5 liters of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven, to
give 47.8 g of product, m.p. 210-212°C. The purity was 99%, based on
GC-MS. 1H NMR (300 MHz, DMSO-af6, ppm): 1.72 (m, 8H), 2.36-2.51 (t, 2H), 2.71 (m, 8H), 3.54-4.03 (m, 6H), 4.76-4.80 (t, 1H), 5.07-5.17 (q, 2H), 5.56-5.77 (d, 2H), 5.80-5.90 (m, 1H), 7.02-7.06 (m, 2H), 7.11-7.17 (m, 4H).
Example 11.12
A variety of allyl DBXs were synthesized using the procedure similar to the one described in Example 2. The structures of example 10

tives had NMR consistent with the indicated structures, and purities of at least 95%, based on GC-MS.
Example 13 Bis-1.3:2.4-(3'.4'-Dimethvlbenzvlidenel 1-Propvl Xvlitol
58 g (0.3 mol) of 1-allyl xylitol syrup (Example 8) was dissolved in 60 ml water. About 0.6 g of platinum (5% weight on activated carbon) hydrogen pressure at 60 psi. The reaction was stopped until no
hydrogen pressure drop was observed. The solid was filtered. The allyl group of the solution was completely turned into propyl group based on NMR. 100g (0.6 mol) of 3,4-dimethyl benzaldehyde, 500 ml ethanol, and 50 ml_ concentrated HCI (12N) were added into the sugar solution.
The clear solution was stirred at room temperature overnight, during
which time a significant amount of white precipitate formed. The powder was isolated by filtration and washed with 100 ml of 1M NaOH aqueous solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to
boiling, then filtered. The white powder was washed with 7 x 500 ml of
boiling water. The washed powder dried overnight. The powder was then stirred in 500 ml of cyclohexane, heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white of product, m.p. 255-257°C. The purity was above 98%, based on GC-
MS. 1H NMR(300 MHz, DMSO-of6, ppm): 0.89-0.93 (t, 3H), 1.30-1.50 (m, 2H), 1.50-1.70 (m, 2H), 2.22 (12H), 3.50-4.05 (m, 6H), 4.78 (1H), 5.56-5.59 (d, 2H), 7.14-7.21 (m, 6H).

About 85 g (0.38 mol) of 1-allyl sorbitol syrup ( product of example
1) was dissolved in 85 ml water. 0.8 g of platinum (5% weight on
activated carbon) was added and the mixture was hydrogenated at room temperature with hydrogen pressure at 60 psi. The reaction was stopped until no hydrogen pressure drop was observed. The solid was filtered. The allyl group of the solution was completely turned into propyl group
based on NMR.
75g (0.54 mol) of 3-methyl-4-fluoro benzaldehyde, 500 ml ethanol, and 56 ml concentrated HCI (12N) were added into the sugar solution. The clear solution was stirred at room temperature overnight, during which time a significant amount of white precipitate formed. The powder
was isolated by filtration and washed with 100 ml of 1M NaOH aqueous
solution. The powder was suspended in water and further neutralized to pH = 7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7 x 500 ml of boiling water. The washed powder dried overnight. The powder was
then stirred in 500 ml of cyclohexane, heated until boiling, filtered, and
washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was washed with methanol, dried in a vacuum oven to give 21 g of product, m.p. 253°C. The purity was above 98%, based on GC-MS. 1H NMR(300 MHz, DMSO-c/6, ppm): 0.91-0.95 (t, 3H), 1.40-1.48 (m,
2H), 1.54-1.67 (m, 2H), 2.13-2.25 (6H), 3.42-4.05 (m, 7H), 4.40 (t,1H),
4.82-4.84 (d, 1H), 5.60-5.62 (d, 2H), 7.11-7.16 (m, 2H), 7.30-7.37 (m, 4H).

A two liter three-necked round bottom flask, equipped with heating
mantle, stirrer, nitrogen inlet, and a condensor, was charged with 600 ml of ethanol, 100 ml of water, 126 g (0.70 mole) of D-glucose, 84 g (0.7 mole) of tin powder (-100 mesh), and 131 g (0.97 mole) of crotyl bromide. The mixture was stirred and slowly heated to reflux - a
significant exotherm and gas evolution was observed at 60°C. The gray
suspension was stirred at reflux overnight, in which time the reaction mixture turned light yellow. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was filtrated and the solution was stirred with 188 g (1.4 mol) 3,4-dimethyl benzaldehyde
overnight, during which time a significant amount of precipitate formed.
The yellow solid was isolated by filtration, washed with methanol to give a white powder, m.p. 233-235°C. GC-MS and NMR indicated the desired compound as a mixture of two diastereomers (2:1), of 1-methyl-2-propenyl.
Example 16
Bis-1.3.2.4-Dibenzvlidene 2'.3'-Dibromopropvl Sorbitol/ Bis-1.3.2.4-Dibenzvlidene 2'-Bromo-3'-Hvdroxvpropvl Sorbitol
An aqueous solution of 90 g allyl sorbitol syrup (Example 1) in 110
g of methanol was titrated with bromine until a light yellow solution. Small amount of NaHS03 was added to give a colorless solution. 1.9 g of p-toulenesulfonic acid monohydrate was added. The clear solution was stirred overnight, during which time a significant amount of white
precipitate formed. The powder was isolated by filtration and washed
with 1M NaOH aqueous solution. The powder was suspended in water

and further neutralized to pH = 7 with a small amount of NaOH. The
suspension was heated to boiling, then filtered. The white powder was
washed with 7 x 500 ml of boiling water. The washed powder dried
overnight. The powder was then stirred in 50 ml of cyclohexane,
heated until boiling, filtered, and washed with 2 x 25 ml of boiling
cyclohexane. The product was dried in a vacuum oven to give 7.3 g of white powder, m.p. 188-190°C. GC-MS and NMR indicated a mixture of bis-1,3:2,4-dibenzylidene 2',3'-dibromopropyl sorbitol (90%) and bis-1,3:2,4-dibenzylidene 2'-bromo-3'-hydroxypropyl sorbitol (10%).
Example 17 Asymmetric benzvlidene/2.4-dimethvlbenzvlidene 1-Ailvl Sorbitol
A 2L reaction kettle, equipped with a stirrer and nitrogen inlet, was
charged with 111 g (0.50 mol) of 1-allyl sorbitol syrup (product of
Example 1) in 280 ml methanol solution. 9.5 g of pTSA, 53 g (0.5 mol)
of benzaldehyde and 67 g (0.50 mol) of 2,4-dimethylbenzaldehyde were
added to the reaction vessel. The clear solution was stirred for 48
hours, during which time a significant amount of white precipitate
formed. The powder was isolated by filtration and washed with 250 ml
of 1M NaOH aqueous solution. The powder was suspended in water
and further neutralized to pH = 7 with a small amount of NaOH. The
suspension was heated to boiling, then filtered. The white powder was
washed with 7 x 500 ml of boiling water. The washed powder dried
overnight. The powder was then stirred in 500 ml of cyclohexane,
heated until boiling, filtered, and washed with 2 x 250 ml of boiling cyclohexane. The isolated white powder was dried in a vacuum oven to give 38.4 g of product, m.p. 234-236°C. Standard analyses of the material indicated that it consisted of a mixture of 1,3-O-

(benzylidene):2,4-O-(2,4-dimethylbenzylidene) 1-allyl sorbitol and 1,3-0-
(2,4-dimethylbenzylidene):2,4-O-benzylidene 1-allyl sorbitol (85%), 1,3:2,4-bis(benzylidene) 1-allyl sorbitol (5%) and 1,3:2,4-bis(2,4-dimethylbenzylidene) 1-allyl sorbitol (10%).
Example 18 Tri-1.3:2.4:5.6-benzvlidene-1 -Allvl Sorbitol
111 g (0.50 mol) of 1-allyl sorbitol syrup (product of Example 1)
was dissolved in 111 g of water. The solution was mixed with 50 g of ice.
With an ice cooling bath, 90 ml of 93% of sulfuric acid was added slowly so the temperature was below 20°C. 106 g (1.0 mol) of benzaldehyde was added. A dark pink suspension was formed. The reaction was allowed to stand at room temperature overnight. The resultant yellow solid was
collected by filtration, neutralized with 10% NaOH solution. The solid was
washed with boiling water, then cool methanol to give a white solid with mp of 216-218°C. Two diastereomers (differ only at the methane carbon attached to the oxygen atoms on carbon 5 and 6 of the allyl sorbitol moiety. The methane carbon can either be in the R or S conformation)
with ratio 24:76 were detected by GC-MS. 1H NMR(500 MHz, DMSO-c/6,
ppm): 2.43-2.45 (t, 2H), 3.95-4.52 (m, 7H), 5.10-5.20 (dd, 2H), 5.72 (s, 1H), 5.79 (s, 1H), 5.89 (s, 1H), 5.86-5.92 (m, 1H), 7.36-7.50 (m, 15H). 13C NMR(125 MHz, DMSO-de, ppm): 34.2, 67.0, 69.6, 70.3, 73.3, 76.9, 77.6, 99.0, 99.1, 102.8, 109.3, 117.6, 126.0, 126.6, 128.0, 128.1, 128.2, 128.6,
128.7, 129.2, 134.0, 137.8, 138.2, 138.4.

Example 19
Bis-1.3: 2.4-(3'-bromo-4'-ethvlbenzvlidene)-1-Allyl Sorbitol/ Mono 2. 4-(3'-bromo-4'-ethvlbenzvlidene)-1-Allvl Sorbitol
A one liter 3-Neck flask, equipped with a mechanical stirring motor, glass stopper, and gas inlet; was purged with argon for 10 minutes. To this vessel, was added 335.2 mL of a 0.4M methanolic solution of 1-allyl sorbitol (30.07g, 134.1 mmol) (product of example 1) and GO.OOg (281.6
mmol) of 3-bromo-4-ethylbenzaldehyde. After stirring reactants for 10
minutes, 42 ml of HCI (12M) was added to catalyze the reaction. Within two minutes following HCI addition, formation of a precipitate occurred and the solution began to take on a pinkish hue. After 3h of reaction, the pinkish tint has dissipated greatly and the amount of pinkish-white solids
had increased. The contents were stirred rapidly and reaction progress
was monitored by GC/MS every 8-12 hours. After 48h, during which a significant amount of off-white precipitate had formed, the reaction was quenched with 54.00g (962.5 mmol) postassium hydroxide [pre-dissolved in D.I. H2O], thereby, giving the mixture a final pH of 12-13.
The crude solids were isolated by Buchner funnel vacuum filtration and
washed with 800 ml of boiling D.I. H20. To remove unreacted sugar, the material was dried overnight, ground to a fine powder, and suspended in 1000 mL of D.I. H2O. The slurried mixture was brought to a boil and stirred for 30 minutes. The solids were captured via Buchner funnel
filtration and further washed with boiling D.I. H20 (3 x 1000 mL). To
remove residual aldehyde, the aforementioned procedure was repeated utilizing boiling methanol as wash solvent. After drying overnight, GC/MS of the solid material showed a mixture of mono:di benzylidene sorbitols [36.85g; 44.5% crude yield]. To separate this mixture, the

crude, white solid was ground to a fine powder, stirred in a boiling 50:50
solvent mixture (CH3OH : D.I. H2O) for 1 h, hot filtered via Buchner
funnel filtration and vacuum dried to give 27.99g of a soft, white powder
[33.8% isolated yield of the DBS]. Analytical examination revealed this
material to be (19a) Bis-1,3, 2,4-(3'-bromo-4'-ethylbenzylidene)-1-
allylsorbitol [see below]. Upon standing overnight, a gelled, white precipitate was observed in the wash solvent utilized during final purification of the DBS [50:50; CH3OH : D.I. H2O]. This precipitate was isolated via Buchner funnel vacuum filtration and vacuum dried to yield
7.48g of a white solid [MBS]. Analytical analysis elucidated this material
as (19b) Mono 2, 4-(3'-bromo-4'-ethylbenzylidene)-1-allylsorbitol [see below].
'(19a) Analytical results found for Bis-1,3, 2,4-(3'-bromo-4'-ethylbenzylidene)-1-allylsorbitol [C27H3206Br2]: The isolated white
powder was dried in a vacuum oven ( give 27.99 g of a soft, white powder, m.p. 268.2-268.6°C [under argon]. Purity was >98.3% based on GC-MS. 1H NMR (500 MHz, DMSO-d6) 6 ppm): 1.15 (dt, 6H, -ChbCHs); 2.42 (tdd, 2H, -allylic methylene); 2.70 (dq, 4H, -CHaCHg); 3.44 (b, m, 1H); 3.61 (b, dq, 1H); 3.74 (b, m, 1H);
3.84 (b, d, 2H); 4.10 (b, m, 2H); 4.43 (t, 1H, 2° -OH); 4.90 (d, 1H, 1°-
OH); 5.14 (b, qm, 2H, -CH=CH2); 5.63 (s, 1 H, acetal); 5.67 (s, 1 H, acetal) 5.88 (m, 1H, -CH=CH2); 7.38 (b, m, 4H, aromatic); 7.58 (b, s, 1 H, aromatic) 7.62 (b, d, 1 H, aromatic). 13C NMR (500 MHz, DMSO-d6, 6 ppm): 14.25 (-CH2CH3); 28.50 (-CH2CH3); 34.29 (-allylic); 62.60;
67.73; 68.86; 70.84; 77.03; 77.53; 97.83 (acetal); 97.94 (acetal); 117.49
(_CH=CH2); 122.81; 122.88; 125.64; 125.78; 129.49; 129.62; 129.72; 129.89; 134.13 (-CH=CH2); 138.33; 138.45; 142.91; 142.97.

(19b) Analytical results found for Mono-2, 4-(3'-bromo-4'-
ethylbenzylidene)-1-allylsorbitol [C18H25O6Br]: The isolated white
powder was dried in a vacuum oven ( give 7.58 g of a soft, white powder, m.p. 199.8-200.5°C [under argon].
Purity was >96% [contained (500 MHz, DMSO-de, 6 ppm): 1.16 (t, 3H, -Ch^CHa); 2.10 (m, 1H, -allylic methylene); 2.40 (b, m, 1H, -allylic methylene); 2.70 (q, 2H, -CHaCHg); 3.41 (m, 1H); 3.47 (b, d, 1H); 3.57 (b, m, 1H); 3.62 (b, d, 1H); 3.74 (b, dm, 2H); 3.88 (b, d, 1H); 4.34 (d, 1H, 1 ° -OH); 4.40 (t, 1H, 2° -
OH); 4.70 (d, 1H, 1° -OH); 4.78 (d, 1H, 1° -OH); 5.03 (b, m, 2H, -
CH=CH2); 5.50 (s, 1H, acetal); 5.91 (b, m, 1H, -CH=CH2); 7.36 (b, m, 2H, aromatic); 7.67 (b, d, 1H, aromatic). 13C NMR (500 MHz, DMSO-d6, 6 ppm): 14.26 (-CH2CH3); 28.49 (-CH2CH3); 37.89 (-allylic); 60.51; 62.70; 67.15; 69.15; 79.54; 82.33; 98.84 (acetal); 116.33 (-CH=CH2);
122.88; 125.99; 129.42; 130.10; 135.92 (-CH=CH2); 138.56; 142.87.
Example 20
12-Hvdroxv Stearic Acid, and Lauryl Sulfuric Acid Na
In a clean 250 ml one-neck flask with a stir bar, was charged with
9.50 g of Bis-1,3;2,4-(4'-ethylbenzylidene) 1-Allyl Sorbitol (Example 2),
0.250 g of 12-hydroxy stearic acid, 0.250 g of lauryl sulfuric acid Na, and
60 g of methanol. The mixture was heated to reflux for one hour with
stirring. The reaction was allowed to cool to room temperature. The
methaol was rotor evaporated, then dried in a vacuum oven at 80°C for 2 hours, to give 9.62 g of product as a white solid. M.P. 203-204°C.

Example 21 Bis-1.3:2.4-(3'.4' dimthvlbenzvlidene) 1-Methyl Sorbitol
2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone (21 a)
27 g of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (50 mmol) was dissolved in 153 ml of DMSO to form a clear solution. 102 ml of acetic anhydride was added dropwise. The resultant clear solution was allowed to stir at room temperature overnight. After 17 hours, GC-MS showed the
lactone was gone and a new compound was observed. The yellow
solution was poured into 600 ml_ of water and sat in a separation funnel overnight. The precipitated oil was passed through a silica gel column, eluted first with cyclohexane then gradually increasing polarity by adding acetone until the final eluent was cyclohexane: acetone = 2:1. The
appropriate portions were collected and evaporated to give a pale syrup.
25.2 g, yield: 94%. IR (v cm'1) 2867, 1752. 3,4,5,7-Tetra-O-benzyl-1-deoxy-D-g/uco-heptulopyranose (21 b)
18 g (33 mmol) of 21 a was dissolved in 200 ml of anhydrous THF under nitrogen. Cooled to -78°C. 45 ml_ of MeLi (1.6 M, 72 mmol) was
added by a syringe. After 1 hour at -78°C, the reaction was quenched by a
solution of 7 g of NH4CI in 200 ml_ of H20. TLC showed no starting material left, while a new spot corresponding to the product appeared. The mixture was extracted by 3 X 150 mL of ethyl acetate, washed by brine, dried over Na2SO4. After evaporation, a thick pale yellow oil was
obtained which was turned into a white solid (17.6 g, 95% yield) with a
melting point of 92-93°C. 300 MHz 1H NMR(CDCI3) 6: 1.41 (s, 3H, CH3); 2.58 (s, 1H, OH); 3.35-3.38 (d, 1H); 3.65-3.72 (m, 3H); 3.93-3.99 (m, 2H); 4.50-4.95 (m, 8H, 4-CH2), 7.14-7.36 (m, 20H). 13C NMR (CDCI3) 6: 26.59, 68.81, 71.55, 73.42, 74.85, 75.58, 75.68, 78.42, 83.18, 83.63, 97.36,

127.58, 127.65, 127.74, 127.82, 127.84, 127.91, 128.28, 128.32, 128.36,
128.41, 137.87, 138.21, 138.25, 138.64.
1,3,4,5-Tetrakis-benzyloxy-heptane-2,6-diol (21 c+21 c')
To a clear solution 5.54 g (10 mmol) of 21 b in 60 mL of THF, 0.5 g
(12.5 mmol) of 95% LiAIH4 was added. The mixture was allowed to stir
under an ice-bath for 4 hours. TLC showed all starting material was gone with two very close new spots appearing. The reaction was carefully quenched with 2N HCI, then extracted with ethyl acetate. The combined organic phase was washed with aqueous NaHCO3, then brine, and dried
over sodium sulfate. A colorless syrup (5.5 g, 99% yield) was obtained
after solvent was evaporated. The ratio of 1.048-1.069 ppm (doublet, 21c): 1.170-1.191 ppm (doublet, 21c') was45%:55%, based on NMR. Heptane-1,2,3,4,5,6-hexaol (21 d+21 d')
To a solution of 2.4 g (4.3 mmol) of 21 c in 100 mL of ethanol, 0.6g
of 5% Pd-C was added. The mixture was hydrogenated at initial hydrogen
pressure at 63 psi. After 6 hours, the catalyst was filtered off and washed with methanol-water. The combined solution was evaporated to give a white solid. 0.80 g, yield: 95%. 300 MHz 1H NMR(D2O) 6: 1.186-1.237 (two doublet, 3H), 3.537-3.988 (m, 7H).
Bis-1,3:2,4-(3',4' dimthylbenzylidene) 1 -Methyl Sorbitol (21)
To a solution of 4.65 g (24 mmol) of 21 d+21 d' in 100 mL of acetic acid was added 4.77 g (36 mmol) of 3,4-dimethyl benzaldehyde. The mixture was allowed to stir at room temperature overnight. The resultant gel was neutralized by KOH-H2O. The white solid (4.2 g) was collected by
filtration and suspended in boiling water. The suspension was filtered hot
and the solid was washing with 7X100ml boiling water. The solid was then suspended in 50 mL of boiling methanol and filtered again. 2.30 g of dry,

white solid was obtained with yield of 25%. GC-MS showed the purity was 98.3%. Melting point: 259-261 °C. 300 MHz 1H NMR(DMSO-d6) 6: 1.23-1.25 (doublet, 3H), 2.21-2.23 (m, 12 H), 3.40-4.80 (m, 9H), 5.55-5.59
(doublet, 2H), 7.10-7.22 (m, 6H). 5
Example 22
Compositions containing various levels of the acetal of examples 2-21, coadditives (0.05 wt. % Irganox 1010, 0.1 wt. % Irgafos 168, and 0.08 wt. % calcium stearate) and the balance polypropylene
homopolymer or polypropene random copolymer (3% ethylene content)
were dry blended in a mechanical mixer, extruded through a single screw extruder at 240°C and pelletized. Plaques were prepared (1.27 mm thick) by injection molding the pellets at 220°C.
The Tc and haze were measured, and the results are reported in
Table 2. Millad 3988® is a registered trademark of Milliken and
Company of Spartanburg, South Carolina. Millad 3988® is a commercially distributed clarifying agent product that employs bis(3,4-dimethylbenzylidene sorbitol)("DMDBS"), as shown and described in United States Patent No. 5,049,605.
TABLE 2: Percent Haze Measurements for Various Compounds

Polymer Example Concentration (ppm) Tc (°C)
Haze(%)
RCPPP (Control) 101.2 44.3
RCPPP Millad 3988® 2500 113.6 7.2
RCPPP 2 6000 115.1 4.9
RCPPP 3 3500 109.4 8.8
RCP PP 4 5000 113.1 10.5
RCPPP 5 5000 107.8 17.2
RCPPP 6 2000 105.2 23.3
RCPPP 8 5000 109.0 8.9
RCPPP 10 5000 109.6 11.3

10

RCPPP 11 5000 111.9 21.8
RCPPP 12 5000 110.8 19.9
RCPPP 13 5000 109.5 8.4
RCPPP 14 5000 111.5 5.6
RCPPP 15 5000 105.8 8.8
RCPPP 16 3000 107.0 18.9
RCPPP 19a 5000 113.1 6.5
RCPPP 19b 5000 110.6 17.3
RCPPP 20 5000 114.6 5.7
RCPPP 21 2500 109.2 23.6
PP (Control) 116.6 58.1
PP Millad 3988® 2500 124.0 11.7
PP 2 5000 125.2 7.5
In some applications of the invention, the nucleating agent
composition may be added to the polymer resin at a concentration of
from about 0.005 to about 3 weight percent. In other applications, a
concentration of between about 0.01 and about 1 weight percent may be
employed. In other applications, a concentration of between about
0.025 and about 0.5 weight percent of the composition is useful.
Concentrates of up to 50 weight percent of the nucleating agent
in resin may also be prepared for blending with additional resin prior to
molding. Typically, concentrates containing 33 weight percent or less of
the nucleating agent in resin are used commercially.
The resin may be extruded a second time immediately before
being processed into a finished article by, for example, injection molding,
extrusion blow molding, injection blow molding, stretch blow molding,
compression molding, rotational molding, profile extrusion, sheet
extrusion, thermal forming, film extrusion, and film extrusion with
orientation.

Gel Formation and Testing
Solid gels also were produced comprising the inventive substituted-alditol derivatives through recognized, simple methods. In particular, specific organic solvents were combined with the additives in certain concentrations and mixed thoroughly. The resultant mixture was then heated to a temperature between about 170°F (77°C) and 300°F (149°C), as indicated below, under agitation for between 5 and 120 minutes. The resultant solution was then poured into a mold to produce a gel stick. The solvents listed are not intended to be exhaustive as to the potential types which may be utilized to form gels with the inventive substituted-alditol derivatives, and thus are merely listed as preferred solvents for such purposes. The examples below were analyzed empirically and by touch to determine if a gel actually formed and the hardness properties as well as any formed gels. Results are reported in Table 3.
Table 3: Gel Sample Data
-.1
Sample - " Number •&„" ^s^ „ -" ;
SOLVENT ' ->! V" i ,r. . s : -
ADDITIVE .; . 'l'_ (Example #:above) s^f^ B
DBS Corfc {Weight^ I>;a3eTs|4V vFbrMatforB
..^ftTflf'r- a. '-J* .-* ~ ^1^ ' ~£&- ••*• •ff^sf*-- > ^,~v*>-s G'efpfiajfSeir:"'" : ffiard/§bft}:":::-
1 1,2-Propanediol 2 1 Y Hard
2 1,3-Propanediol 2 1 Y Hard
3 2-Chlorotoluene 2 1 Y Soft
4 Toluene 2 1 Y Soft
5 Benzonitrile 2 1 Y Soft
6 1,2-Propanediol 13 1 Y Hard
7 2-Chlorotoluene 13 1 Y Hard
8 Benzonitrile 2 3 Y Hard
9 1,2-Propanediol 2 3 Y Hard
10 1,3-Propanediol 2 3 Y Hard
11 2-Chlorotoluene 2 3 Y Soft
12 1,2-Propanediol 13 3 Y Hard
13 2-Chlorotoluene 13 3 Y Hard
14 1,2-Propanediol 18 1 Y Hard
15 1,3-Propanediol 18 1 Y Hard

Thus, the inventive substituted-alditol derivatives provide excellent
gelling capabilities for solvents, depending upon their concentration
without the target solvents.
It is understood by one of ordinary skill in the art that the present
discussion is a description of exemplary embodiments only, and is not
intended as limiting the broader aspects of the present invention, which
broader aspects are embodied in the exemplary constructions. The
invention is shown by example in the appended claims.

WE CLAIM:
1. A diacetal compound conforming to the structure:
(Formula Removed)
wherein;
n is 0,1 or 2
Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl-containing
groups; and R is selected from the group consisting of alkenyls, alkyls, alkoxy, hydroxyl
alkyls, and alkyl-halides, wherein the hydroyl alkyls are selected from the group
consisting of-CHOHCHOHCH2OH, where X'' is a halide group.
2 The compound as claimed in claim 1 wherein n=0.
3. The compound as claimed in claim 1 wherein n=l.
3. The compound as claimed in claim 1 wherein n = 2.
4. The compound as claimed in claim 1 wherein R is allyl.
5. The compound as claimed in claim 1 wherein R is propyl.
7. A polyolefin-containing composition having therein the compound as claimed in claim 1.
8. The compound as claimed in claim 1 wherein said R is selected from one of the
following:
(Formula Removed)
wherein X, X1, X", and X'", if present, are independently selected halide groups,
9. The compound as claimed in claim 8 wherein Ar1 and Ar2 are independently selected
from the group of substituted benzaldehydes including:
(Formula Removed)
10. The compound as claimed in claim 9 wherein said Ar1 and AR2 are both 4-
propylbenzaldehyde.
11. A formed or molded polyolefin article comprising the compound as claimed in claim 1.
12. The compound as claimed in claim 1 with structure:

(Formula Removed)
wherein n is 1 ;
R is an alkenyl or alkyl group;
R1, R2, R3, R4, and R5 each are independently selected from the
group consisting of hydrogen, alkyls, alkynyls, alkoxy, carboxy,
halogens, and phenyls.
13. The compound as claimed in claim 12 wherein said R is selected from one of the
following:
(Formula Removed)
14. The compound as claimed in claim 13 wherein R comprises
(Formula Removed)
15. The compound as claimed in claim 13 wherein R comprises -CH2CH2CH3.
16. The compound as claimed in claim 13 wherein one of said R1, R2, R3, R4 and R5 comprises an alkyl,
17. An acetal of a substituted alditol conforming to the structure (III)
(Formula Removed)
made by reacting (a) and (b):
(a) a substituted alditol compound
(Formula Removed)
wherein
n is 0, 1 or 2; and R is selected from the group consisting of alkenyl, alkyl, alkoxy,
and alkylhalides and
(b) at least one mole of substituted or unsubstituted benzaldehyde per mole of substituted
aldlitol compound, said benzldehyde being as shown:
(Formula Removed)
wherein R1, R2, R3, R4 and R5 each are independently selected from the group consisting of: hydrogen, alkyls, fluorocarbons, alkenyls, alkenyls, alkoxy, carboxy, halogens, cyclic groups, and phenyls.
18. A method of providing a nucleated or clarified polyolefin composition, the method comprising in part combining with said polyolefin composition the compound claimed in claim 1 having compound having the structure:
(Formula Removed)
wherein:
n is 0, 1 or 2;
AR1 and Ar2 are independently selected from substituted or unsubstituted aryl-containing groups; and
R is selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides.
19. The method as claimed in claim 18 wherein said R is selected from one of the following:
(Formula Removed)

Documents:

5394-delnp-2006-Abstract-(21-07-2011).pdf

5394-delnp-2006-abstract.pdf

5394-delnp-2006-assignment.pdf

5394-delnp-2006-Claims-(21-07-2011).pdf

5394-delnp-2006-claims.pdf

5394-delnp-2006-Correspondence Others-(21-07-2011).pdf

5394-delnp-2006-correspondence-others-1.pdf

5394-delnp-2006-correspondence-others.pdf

5394-delnp-2006-description (complete).pdf

5394-delnp-2006-Form-1-(21-07-2011).pdf

5394-delnp-2006-form-1.pdf

5394-delnp-2006-form-18.pdf

5394-delnp-2006-Form-2-(21-07-2011).pdf

5394-delnp-2006-form-2.pdf

5394-delnp-2006-Form-3-(21-07-2011).pdf

5394-delnp-2006-form-3.pdf

5394-delnp-2006-form-5.pdf

5394-delnp-2006-GPA-(21-07-2011).pdf

5394-delnp-2006-gpa.pdf

5394-delnp-2006-pct-101.pdf

5394-delnp-2006-pct-301.pdf

5394-delnp-2006-pct-304.pdf

5394-delnp-2006-pct-308.pdf

5394-delnp-2006-pct-311.pdf

5394-delnp-2006-Petition-137-(21-07-2011).pdf

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Patent Number

262794

Indian Patent Application Number

5394/DELNP/2006

PG Journal Number

39/2014

Publication Date

26-Sep-2014

Grant Date

13-Sep-2014

Date of Filing

18-Sep-2006

Name of Patentee

MILLIKEN & COMPANY

Applicant Address

920 MILLIKEN ROAD, (M-495)SPARTANBURG, SC 29303, UNITED STATES OF AMERICA.

Inventors:

#	Inventor's Name	Inventor's Address
1	CHUNPING XIE	494 CHIPPENDALE LANE, BOILING SPRINGS, SC 29316, USA.
2	JOHN D.O. ANDERSON	334 WEST AUTUMN RIDGE ROAD, MOORE , SC 29369, USA
3	WALTER A. SCRIVENS	147 MORNINGLAKE DRIVE MOORE, SOUTH CAROLINA 29369, USA
4	JIANG LI	221 HUNTERS POINT DRIVE, SPARTANBURG, SC 29303, USA.
5	LEE R. RIETH	425 OLD IRON WORKS ROAD, SPARTANBURG, SC 29302, USA.
6	JASON A SMITH	124 RIDGE GLEN, SIMPSONVILLE, SC 29680, USA.
7	SHANE M. WAYBRIGHT	224 SILVERBELL DRIVE, BOILING SPRING, SC 29316, USA
8	BRIAN M. BURKHART	4 BRAELOCK COURT, GREENVILLE, SC 29316, USA

PCT International Classification Number

C08K 5/1575

PCT International Application Number

PCT/US2005/011686

PCT International Filing date

2005-04-05

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	10/831,920	2004-04-26	U.S.A.
2	10/893,633	2004-07-16	U.S.A.