Indian Patents. 270541:POLY(BEHENYL UNDECYLENATE-CO-MALIC ANHYDRIDE)DIBEHENATE HAVING POUR POINT DEPRESSANT ACTIVITY IN NON-EDIBLE OIL AND PROCESS FOR PREPARATION THEREOF

Title of Invention	POLY(BEHENYL UNDECYLENATE-CO-MALIC ANHYDRIDE)DIBEHENATE HAVING POUR POINT DEPRESSANT ACTIVITY IN NON-EDIBLE OIL AND PROCESS FOR PREPARATION THEREOF
Abstract	Poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil and process for preparation thereof The invention relates to a poly(behenyl undecylenate-co-mateic anhydride)dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1:

Full Text	FORM 2 THE PATENTS ACT, 1970 (39 of 1970) As amended by the Patents (Amendment) Act, 2005 & The Patents Rules, 2003 As amended by the Patents (Amendment) Rules, 2006 COMPLETE SPECIFICATION (See section 10 and rule 13) TITLE OF THE INVENTION Poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil and process for preparation thereof APPLICANTS Crompton Greaves Limited, CG House, Dr Annie Besant Road, Prabhadevi, Mumbai 400 030, Maharashtra, India, an Indian Company INVENTOR Chaudhari Sushil Ekanath, Crompton Greaves Limited, Condition Monitoring and Diagnostic Centre (CMDRC), Global R&D Centre, Kanjur Marg (East), Mumbai 400042, Maharashtra, India, an Indian national PREAMBLE TO THE DESCRIPTION The following specification particularly describes this invention and the manner in which it is to be performed: FIELD OF THE INVENTION This invention relates to a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil and a process for the preparation thereof. BACKGROUND OF THE INVENTION Silicone fluid, synthetic hydrocarbon oils or petroleum based mineral oils, are conventionally used for insulating electrical components. However, over a period of time and with continuous exposure to high voltage electricity, the heat dissipating, insulating and dielectric characteristics of the above insulating fluids deteriorate. Moreover, they are not biodegradable and hence pose grave environmental problems. Mineral oil is also highly inflammable and is an unsuitable insulating medium for indoor and vault equipment installations. The environmental effects due to disposal of petroleum based products, oil spills and the fact that petroleum based products are non-renewable, have prompted interest in the use of vegetable oils as viable substitutes. However, in their natural state, vegetable oils have high viscosity which causes operational problems in transformers. Hence, all vegetable oils are transesterified prior to use as insulating fluids. The high cost of edible oils and the higher cost of preparing trans-esters of edible oils has discouraged the use of edible vegetable oils as substitutes for mineral oil. Karanjia oil is a non-edible vegetable oil which is relatively cheap and is generally used for making biodiesel. The term "non-edible oil" used hereinafter refers to mineral oil and/or vegetable oil. The pour point is the lowest temperature at which liquids can flow under standard conditions prescribed by ASTM D97. A pour point depressant (PPD) lowers that temperature. Pour point depressants are designed to control wax crystal formation in oils resulting in improved flow performance of the oil at lower temperatures, i.e, the PPDs lower the pour point of the oil. In cold climates, vegetable oils tend to solidify more readily than mineral oil i.e. vegetable oils have a relatively higher pour point than mineral oil. Addition of a pour point depressant to vegetable oils lowers the pour point of vegetable oils. Pour point depressants currently being used include, ethylene vinyl acetate (EVA) copolymers, polymethacrylates, poly aery lates, alkyl esters of styrene-maleic anhydride copolymers, copolymers of olefins, acrylamides, polyacrylamides, copolymers of maleimide, maieic anhydrides, compounds of alkyl amines, alkyl ammonium salts, copolymers. of mono, dicarboxylic acids with monohydric, dihydric or polyhydric alcohols, branched polyalkyl methacrylates with functional group containing nitrogen, sulfone copolymers or copolymers of alpha olefins and maieic anhydride. However, many of these pour point depressants like polymethacrylates, polyacrylates and polyalkyl methacrylates are known to be nonbiodegradable, expensive and even carcinogenic. OBJECTS OF THE INVENTION An object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for non-edible oil. Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for non-edible oil which is economical. Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for karanja oil. Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for karanja oil which is economical. Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for non-edible oil. Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for non-edible oil which is simple, easy and convenient to carry out and is economical. Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for karanja oil. Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for karanja oil which is simple, easy and convenient to carry out and is economical. DETAILED DESCRIPTION OF THE INVENTION According to the invention there is provided a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. According to the invention there is also provided a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. According to the invention there is also provided a process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units, the process comprising: a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester; b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75 °C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst. Accoring to the invention there is further provided a process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units, the process comprising: a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester; b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75 °C to obtain a poIy(behenyl undecylenate-co-maleic anhydride) copolymer; and c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst. Preferably, the organic solvent is selected from toluene, dry benzene or xylene. Preferably, the inert atmosphere is provided by dry nitrogen gas. Preferably, the free radical initiator is benzoyl peroxide or azobisisobutyronitrile (AIBN). Preferably, the acid catalyst is para-toluene sulfonic acid or sulphuric acid or a combination thereof. 7 The poly(behenyl undecylenate-co-maleic anhydride)dibehenate obtained by the process of the invention has a molecular weight of 20,000 to 50,000. The molecular weight of poly(behenyl undecylenate-co-maleic anhydride)dibehenate can be varied in the range of 20,000 to 50,000 by varying the process parameters such as the free radical initiator concentration, the stirring rate and the reaction time. The invention also provides a karanja oil comprising poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity, and the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. Preferably, the karanja oil comprises 100 to 500ppm of poly(behenyl undecylenate-co-maleic anhydride)dibehenate. The poly{behenyI undecylenate-co-maleic anhydride)dibehenate of the invention is very effective and efficient in depressing the pour point of non-edible oil and is prepared using raw materials like behenyl alcohol and undecylenic acid which are easily obtainable from the naturally occurring fats and oils. Therefore, the pour point depressant of the invention is non-carcinogenic, economical and bio-degradable. The process of the invention is also simple, easy and convenient to carry out and economical. Karanja oil is a low cost oil obtained from renewable natural resources. The addition of the pour point depressant of the above invention to karanja oil yields a low cost insulating medium which can replace mineral oil or even be used in combination with mineral oil to serve as an eco-friendly and efficient insulating medium. The following experimental examples are illustrative of the invention but not limitative of the scope thereof: Example 1 Undecylenic acid (0.051 M, 9.58 g) was esterified with behenyl alcohol (0.025 M, 8.491 g) at lire for 12 hours in the presence of toluene (75 ml) and sulphuric acid (0.2 ml) to obtain behenyl undecylenate. Water was eliminated from the reaction mixture by azeotropic distillation. The resulting crude ester was neutralized with sodium bicarbonate. The organic layer was separated and washed with water to remove traces of sodium bicarbonate and finally dried over anhydrous sodium sulphate. Solvent recovery was achieved by vacuum distillation. The behenyl undecylenate (0.025 M, 12.332 g) was copolymerized with double re-crystallized maleic anhydride (0.025 M, 2.451 g) in the presence of dry benzene under dry nitrogen atmosphere with azobisisobutyronitrile (1% by weight of total reactant weight) at 55 to 60°C with constant stirring for 5 hours to give poly(behenyl undecylenate-co-maleic anhydride) which was purified by repeated solvent non-solvent precipitation (benzene-methanol) method. Traces of the solvent were removed by drying under reduced pressure at 50°C / 25mm Hg for 5 hours. The poly(behenyl undecylenate-co-maleic anhydride) (0.019 M, 8.02 gm) was diesterified with 2 moles of behenyl alcohol (0.032 M, 6.04 gm) in the presence of xylene (60 ml) and para-toluene sulfonic acid (0.1 gm) and sulphuric acid (0.1 ml) at 140°C to produce poly(behenyl undecylenate-co-maleic anhydride)dibehenate which was neutralized with sodium bicarbonate and separated and dried over anhydrous sodium sulfate. Solvent was recovered by vacuum distillation. The crude diester was purified by repeated precipitation in excess acetone and dried under vacuum at 40°C/25mm Hg for 5 hours. The poly(behenyl undecylenate-co-maleic anhydride)dibehenate obtained in this example had a molecular weight of 35,841. Example 2 100 ppm and 500 ppm of poly (behenyl undecylenate-co-maleic anhydride)dibehenate obtained in Example 1 was added to karanja oil. The standard method as prescribed by the ASTM D97 was used for determining the pour point of karanja oil on addition of varying amounts of poly(behenyl undecylenate-co-maleic anhydride)dibehenate and the results were as shown in the following Table 1 : Table 1 Pour point depressant (PPD) comprising: Pour point of virgin karanja oil Pour point of karanja oil after addition of PPD Extent of depression in pour point 100 ppm of PPD 500 ppm of PPD 100 ppm of PPD 500 ppm of PPD Poly(behenyl undecylenate-co-mal ei c anhydride) dibehenate 12 °C 6°C -12°C 6°C 24°C Table 1 clearly shows that the pour point depressant of the invention namely poly(behenyl undecylenate-co-maleic anhydride)behenate has excellent pour point depressant activity in karanja oil in a range of concentrations from lOOppm to 500ppm of poly(behenyl undecylenate-co-maleic anhydride)behenate in the oil. The above examples are non-limiting. The invention is defined by the claims that follow. We claim: 1. A poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. 2. A poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. 3. The poly(behenyl undecylenate-co-maleic anhydride)dibehenate as claimed in claim 1 or 2 having a molecular weight of 20,000 to 50,000. 4. A process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units, the process comprising: a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester; b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75°C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst. 5. A process for the preparation of a poly(behenyI undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units, the process comprising: a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester; b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75°C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst. 6. "The process as claimed in claim 4 or 5, wherein the organic solvent is selected from toluene, dry benzene or xylene. 7. The process as claimed in any one of claims 4 to 6, wherein the inert atmosphere is provided by dry nitrogen gas. 8. The process as claimed in any one of claims 4 to 7, wherein the free radical initiator is benzoyl peroxide or azobisisobutyronitrile (AIBN). 9. The process as claimed in any one of claims 4 to 8, wherein the acid catalyst is para-toluene sulfonic acid or sulphuric acid or a combination thereof. 10. The process as claimed in any one of claims 4 to 9, wherein the poly(behenyl undecylenate-co-maleic anhydride)dibehenate has a molecular weight of 20,000 to 50,000. 11. A karanja oil comprising poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity, and the general formula 1: Formula 1 wherein R represents behenyl group and n represents the number of repeating units. 15 12. The karanja oil as claimed in claim 11 comprising 100 to 500ppm of poly(behenyl undecylenate-co—maleic anhydride)dibehenate. 13. The karanja oil as claimed in claim 11 or 12, wherein the poly(behenyl undecylenate—co-maleic anhydride)dibehenate has a molecular weight of 20,000 to 50,000.

Full Text

FORM 2
THE PATENTS ACT, 1970
(39 of 1970)
As amended by the Patents (Amendment) Act, 2005
&
The Patents Rules, 2003
As amended by the Patents (Amendment) Rules, 2006
COMPLETE SPECIFICATION
(See section 10 and rule 13)
TITLE OF THE INVENTION
Poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil and process for preparation thereof
APPLICANTS
Crompton Greaves Limited, CG House, Dr Annie Besant Road, Prabhadevi, Mumbai 400 030, Maharashtra, India, an Indian Company
INVENTOR
Chaudhari Sushil Ekanath, Crompton Greaves Limited, Condition Monitoring and Diagnostic Centre (CMDRC), Global R&D Centre, Kanjur Marg (East), Mumbai 400042, Maharashtra, India, an Indian national
PREAMBLE TO THE DESCRIPTION
The following specification particularly describes this invention and the manner in which it is to be performed:

FIELD OF THE INVENTION
This invention relates to a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil and a process for the preparation thereof.
BACKGROUND OF THE INVENTION
Silicone fluid, synthetic hydrocarbon oils or petroleum based mineral oils, are conventionally used for insulating electrical components. However, over a period of time and with continuous exposure to high voltage electricity, the heat dissipating, insulating and dielectric characteristics of the above insulating fluids deteriorate. Moreover, they are not biodegradable and hence pose grave environmental problems. Mineral oil is also highly inflammable and is an unsuitable insulating medium for indoor and vault equipment installations. The environmental effects due to disposal of petroleum based products, oil spills and the fact that petroleum based products are non-renewable, have prompted interest in the use of vegetable oils as viable substitutes. However, in their natural state, vegetable oils have high viscosity which causes operational problems in transformers. Hence, all vegetable oils are transesterified prior to use as insulating fluids. The high cost of edible oils and the higher cost of preparing trans-esters of edible oils has discouraged the use of edible vegetable oils as substitutes for mineral oil. Karanjia oil is a non-edible vegetable oil which is relatively cheap and is generally used for making biodiesel. The term "non-edible oil" used hereinafter refers to mineral oil and/or vegetable oil.

The pour point is the lowest temperature at which liquids can flow under standard conditions prescribed by ASTM D97. A pour point depressant (PPD) lowers that temperature. Pour point depressants are designed to control wax crystal formation in oils resulting in improved flow performance of the oil at lower temperatures, i.e, the PPDs lower the pour point of the oil. In cold climates, vegetable oils tend to solidify more readily than mineral oil i.e. vegetable oils have a relatively higher pour point than mineral oil. Addition of a pour point depressant to vegetable oils lowers the pour point of vegetable oils. Pour point depressants currently being used include, ethylene vinyl acetate (EVA) copolymers, polymethacrylates, poly aery lates, alkyl esters of styrene-maleic anhydride copolymers, copolymers of olefins, acrylamides, polyacrylamides, copolymers of maleimide, maieic anhydrides, compounds of alkyl amines, alkyl ammonium salts, copolymers. of mono, dicarboxylic acids with monohydric, dihydric or polyhydric alcohols, branched polyalkyl methacrylates with functional group containing nitrogen, sulfone copolymers or copolymers of alpha olefins and maieic anhydride. However, many of these pour point depressants like polymethacrylates, polyacrylates and polyalkyl methacrylates are known to be nonbiodegradable, expensive and even carcinogenic.
OBJECTS OF THE INVENTION
An object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for non-edible oil.
Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for non-edible oil which is economical.

Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for karanja oil.
Another object of the invention is to provide a bio-degradable, non-carcinogenic pour point depressant for karanja oil which is economical.
Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for non-edible oil.
Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for non-edible oil which is simple, easy and convenient to carry out and is economical.
Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for karanja oil.
Another object of the invention is to provide a process for the preparation of a biodegradable, non-carcinogenic pour point depressant for karanja oil which is simple, easy and convenient to carry out and is economical.
DETAILED DESCRIPTION OF THE INVENTION
According to the invention there is provided a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil, and

having the general formula 1:
Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
According to the invention there is also provided a poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
According to the invention there is also provided a process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units,
the process comprising:
a) esterifying a straight chain aliphatic unsaturated undecylenic acid with
behenyl alcohol in the molar ratio of 2:1 in the presence of an organic
solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic
conditions to obtain an alkyl ester;
b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75 °C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and
c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst.
Accoring to the invention there is further provided a process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units,
the process comprising:
a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester;
b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75 °C to obtain a poIy(behenyl undecylenate-co-maleic anhydride) copolymer; and
c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst.
Preferably, the organic solvent is selected from toluene, dry benzene or xylene. Preferably, the inert atmosphere is provided by dry nitrogen gas. Preferably, the free radical initiator is benzoyl peroxide or azobisisobutyronitrile (AIBN). Preferably, the acid catalyst is para-toluene sulfonic acid or sulphuric acid or a combination thereof.
7

The poly(behenyl undecylenate-co-maleic anhydride)dibehenate obtained by the process of the invention has a molecular weight of 20,000 to 50,000. The molecular weight of poly(behenyl undecylenate-co-maleic anhydride)dibehenate can be varied in the range of 20,000 to 50,000 by varying the process parameters such as the free radical initiator concentration, the stirring rate and the reaction time.
The invention also provides a karanja oil comprising poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity, and the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
Preferably, the karanja oil comprises 100 to 500ppm of poly(behenyl undecylenate-co-maleic anhydride)dibehenate.
The poly{behenyI undecylenate-co-maleic anhydride)dibehenate of the invention is very effective and efficient in depressing the pour point of non-edible oil and is prepared using raw materials like behenyl alcohol and undecylenic acid which are easily obtainable from the naturally occurring fats and oils. Therefore, the pour point depressant of the invention is non-carcinogenic, economical and bio-degradable. The

process of the invention is also simple, easy and convenient to carry out and economical. Karanja oil is a low cost oil obtained from renewable natural resources. The addition of the pour point depressant of the above invention to karanja oil yields a low cost insulating medium which can replace mineral oil or even be used in combination with mineral oil to serve as an eco-friendly and efficient insulating medium.
The following experimental examples are illustrative of the invention but not limitative of the scope thereof:
Example 1 Undecylenic acid (0.051 M, 9.58 g) was esterified with behenyl alcohol (0.025 M, 8.491 g) at lire for 12 hours in the presence of toluene (75 ml) and sulphuric acid (0.2 ml) to obtain behenyl undecylenate. Water was eliminated from the reaction mixture by azeotropic distillation. The resulting crude ester was neutralized with sodium bicarbonate. The organic layer was separated and washed with water to remove traces of sodium bicarbonate and finally dried over anhydrous sodium sulphate. Solvent recovery was achieved by vacuum distillation.
The behenyl undecylenate (0.025 M, 12.332 g) was copolymerized with double re-crystallized maleic anhydride (0.025 M, 2.451 g) in the presence of dry benzene under dry nitrogen atmosphere with azobisisobutyronitrile (1% by weight of total reactant weight) at 55 to 60°C with constant stirring for 5 hours to give poly(behenyl undecylenate-co-maleic anhydride) which was purified by repeated solvent non-solvent precipitation (benzene-methanol) method. Traces of the solvent were removed by drying under reduced pressure at 50°C / 25mm Hg for 5 hours.

The poly(behenyl undecylenate-co-maleic anhydride) (0.019 M, 8.02 gm) was diesterified with 2 moles of behenyl alcohol (0.032 M, 6.04 gm) in the presence of xylene (60 ml) and para-toluene sulfonic acid (0.1 gm) and sulphuric acid (0.1 ml) at 140°C to produce poly(behenyl undecylenate-co-maleic anhydride)dibehenate which was neutralized with sodium bicarbonate and separated and dried over anhydrous sodium sulfate. Solvent was recovered by vacuum distillation. The crude diester was purified by repeated precipitation in excess acetone and dried under vacuum at 40°C/25mm Hg for 5 hours. The poly(behenyl undecylenate-co-maleic anhydride)dibehenate obtained in this example had a molecular weight of 35,841.
Example 2
100 ppm and 500 ppm of poly (behenyl undecylenate-co-maleic anhydride)dibehenate
obtained in Example 1 was added to karanja oil. The standard method as prescribed by the ASTM D97 was used for determining the pour point of karanja oil on addition of varying amounts of poly(behenyl undecylenate-co-maleic anhydride)dibehenate and the results were as shown in the following Table 1 :
Table 1

Pour point depressant (PPD) comprising: Pour point of virgin karanja oil Pour point of karanja oil after
addition of PPD Extent of depression in pour point

100 ppm of PPD 500 ppm of PPD 100 ppm of PPD 500 ppm of PPD
Poly(behenyl undecylenate-co-mal ei c anhydride) dibehenate 12 °C 6°C -12°C 6°C 24°C

Table 1 clearly shows that the pour point depressant of the invention namely poly(behenyl undecylenate-co-maleic anhydride)behenate has excellent pour point depressant activity in karanja oil in a range of concentrations from lOOppm to 500ppm of poly(behenyl undecylenate-co-maleic anhydride)behenate in the oil.
The above examples are non-limiting. The invention is defined by the claims that follow.

We claim:
1. A poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
2. A poly(behenyl undecylenate-co-maleic anhydride)dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
3. The poly(behenyl undecylenate-co-maleic anhydride)dibehenate as claimed in claim 1 or 2 having a molecular weight of 20,000 to 50,000.

4. A process for the preparation of a poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in non-edible oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units,
the process comprising:
a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester;
b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75°C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and
c) diesterifying the copolymer with behenyl alcohol in the molar ratio of 1:2 at 110°C to 140°C in the presence of an organic solvent and an acid catalyst.

5. A process for the preparation of a poly(behenyI undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity in vegetable oil, preferably karanja oil, and having the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units,
the process comprising:
a) esterifying a straight chain aliphatic unsaturated undecylenic acid with behenyl alcohol in the molar ratio of 2:1 in the presence of an organic solvent and sulphuric acid catalyst at 110°C to 140°C under azeotropic conditions to obtain an alkyl ester;
b) copolymerizing the alkyl ester with a double re-crystallized maleic anhydride in the 1:1 molar ratio under inert atmosphere and in the presence an organic solvent and a free radical initiator at 50°C to 75°C to obtain a poly(behenyl undecylenate-co-maleic anhydride) copolymer; and
c) diesterifying the copolymer with behenyl alcohol in the molar ratio of
1:2 at 110°C to 140°C in the presence of an organic solvent and an acid
catalyst.

6. "The process as claimed in claim 4 or 5, wherein the organic solvent is selected from toluene, dry benzene or xylene.
7. The process as claimed in any one of claims 4 to 6, wherein the inert atmosphere is provided by dry nitrogen gas.
8. The process as claimed in any one of claims 4 to 7, wherein the free radical initiator is benzoyl peroxide or azobisisobutyronitrile (AIBN).
9. The process as claimed in any one of claims 4 to 8, wherein the acid catalyst is para-toluene sulfonic acid or sulphuric acid or a combination thereof.
10. The process as claimed in any one of claims 4 to 9, wherein the poly(behenyl undecylenate-co-maleic anhydride)dibehenate has a molecular weight of 20,000 to 50,000.
11. A karanja oil comprising poly(behenyl undecylenate-co-maleic anhydride) dibehenate having pour point depressant activity, and the general formula 1:

Formula 1 wherein R represents behenyl group and n represents the number of repeating units.
15

12. The karanja oil as claimed in claim 11 comprising 100 to 500ppm of
poly(behenyl undecylenate-co—maleic anhydride)dibehenate.
13. The karanja oil as claimed in claim 11 or 12, wherein the poly(behenyl
undecylenate—co-maleic anhydride)dibehenate has a molecular weight of 20,000 to
50,000.

Documents:

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Patent Number

270541

Indian Patent Application Number

650/MUM/2009

PG Journal Number

01/2016

Publication Date

01-Jan-2016

Grant Date

30-Dec-2015

Date of Filing

20-Mar-2009

Name of Patentee

CROMPTON GREAVES LTD

Applicant Address

CG HOUSE, DR ANNIE BESANT ROAD, WORLI, MUMBAI

Inventors:

#	Inventor's Name	Inventor's Address
1	SUSHIL EKNATH CHAUDHARI	CONDITION MONITORING AND DIAGNOSTIC CENTRE (CMDRC), CG GLOBAL R&D CENTRE, KANJUR MARG (EAST), MUMBAI-400042,

PCT International Classification Number

C10L1/02; C10L1/14; C10L1/16

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA