COMPOSITION AND METHOD

Abstract

A surfactant comprising the reaction product of: (a) an epoxidised carboxylic acid ester; and (b) a compound including at least one reactive alcohol and/or amino functional group.

Claims

1. (canceled)

2. A method of preparing a surfactant, the method comprising reacting: (a) an epoxidised carboxylic acid ester; and (b) a compound including at least one reactive alcohol and/or amino functional group.

3. The method according to claim 2 wherein component (a) comprises an ester of formula RCOOR.sup.1 in which R is a hydrocarbyl group including an epoxy functional group and R.sup.1 is a hydrocarbyl group.

4. The method according to claim 3 wherein R is an unbranched aliphatic group having 6 to 26 carbon atoms and R.sup.1 is methyl or 2-ethylhexyl.

5. The method according to claim 2 wherein component (a) is derived from soybean oil fatty acid.

6. The method according to claim 2 wherein component (b) comprises a compound of formula (I): ##STR00008## wherein n is 0 or a positive integer; each X is independently O or NH; each group R.sup.4 is independently an optionally substituted alkylene, alkenylene or arylene group; and R.sup.5 is hydrogen or an optionally substituted alkyl, alkenyl, aryl, alkaryl or aralkyl group provided that n is not 0 when R.sup.5 is hydrogen.

7. The method according to claim 6 wherein component (b) comprises an alkoxylated compound.

8. The method according to claim 6 wherein each X is O, n is 20 to 100, R.sup.5 is hydrogen and each R.sup.4 is a C2 to C4 alkylene group.

9. The method according to claim 2, wherein the surfactant comprises a derivatised surfactant, and wherein the method further comprises reacting: (c) a derivatising agent.

10. (canceled)

11. The method according to claim 9 wherein reaction with component (c) introduces a polar functional group into the derivatised surfactant.

12. The method according to claim 11 wherein the polar functional group is selected from the group consisting of anionic and cationic functional groups.

13. The method according to claim 9 wherein component (c) comprises a compound of formula (III): ##STR00009## wherein p is 0 or a positive integer, each X.sup.3 is independently O or NR.sup.11, X.sup.4 is O or NR.sup.12, each R.sup.9 is independently an optionally substituted alkylene, alkenylene or arylene group, and each of R.sup.10, R.sup.11 and R.sup.12 is hydrogen or an optionally substituted alkyl, alkenyl, aryl, alkaryl or aralkyl group.

14. The method according to claim 9 which involves the steps of: (i) reacting (a) an epoxidised carboxylic acid ester with (b) a compound including at least one reactive alcohol and/or amino functional group; (ii) reacting the reaction product of step (i) with (c) a derivatising agent comprising a compound including at least one reactive alcohol or amino functional group and one tertiary amino group; and (iii) reacting the reaction product of step (ii) with (d) a quaternising agent.

15. The method according to claim 9 wherein component (c) comprises a sulfonating agent.

16. The method according to claim 9 wherein component (c) comprises a hydrolysis agent.

17. A composition comprising a surfactant or derivatised surfactant made by a method according to claim 2.

18. (canceled)

19. The method according to claim 23 in the fields of inks, paints, pigment preparations, dispersions, detergents, personal care, toiletries, agrochemicals, oilfields, lubricants, fuels, coatings, cosmetics or emulsion polymers.

20. The method according to claim 11 wherein the polar functional group is selected from the group consisting of a sulfonate moiety, a sulfate moiety, a carboxylate moiety, a quaternary ammonium moiety, a phosphonate moiety, a phosphate moiety, a hydroxy group, an amino group, an alkoxylated chain, and a combination thereof.

21. The composition according to claim 17 further comprising one or more further components.

22. The composition according to claim 17, wherein the surfactant comprises a derivatised surfactant, and wherein the method further comprises reacting a derivatizing agent.

23. A method of reducing a surface tension at an interface, the method comprising applying a composition according to claim 17.

Description

EXAMPLES

Example 1

[0210] Reaction of Epoxidised Methyl Soyate (Soybean Oil Methyl Ester) with Polyethylene Glycol 200 Molecular Weight

[0211] 284.8 grams of epoxidised soyate with an epoxide value of 227 mg KOH/g was placed into a flask. 115.2 grams of 200 molecular weight polyethylene glycol (1:1 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 20° C. 0.32 grams of boron trifluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 60° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 2

[0212] Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 200 Molecular Weight

[0213] 221.1 grams of epoxidised soyate with an epoxide value of 227 mg KOH/g was placed into a flask. 178.9 grams of 200 molecular weight polyethylene glycol (1:2 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 20° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 60° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 3

[0214] Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 600 Molecular Weight

[0215] 180.7 grams of epoxidised soyate with an epoxide value of 227 mg KOH/g was placed into a flask. 219.3 grams of 600 molecular weight polyethylene glycol (1:1 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 30° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 60° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 4

[0216] Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 1500 Molecular Weight

[0217] 99.1 grams of epoxidised soyate with an epoxide value of 210 mg KOH/g was placed into a flask. 300.9 grams of 1500 molecular weight polyethylene glycol (1:1 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 80° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 5

[0218] Reaction of Epoxidised Methyl Soyate with Polytetrahydrofuran 650 Molecular Weight

[0219] 172.8 grams of epoxidised soyate with an epoxide value of 210 mg KOH/g was placed into a flask. 227.2 grams of 650 molecular weight polytetrahydrofuran (1:1 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 80° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 6

[0220] Reaction of Epoxidised Methyl Soyate with a 400 Molecular Weight Polyether Diamine Based on Polypropylene Glycol

[0221] 213.8 grams of epoxidised soyate with an epoxide value of 210 mg KOH g was placed into a flask. 186.2 grams of 400 molecular weight polyether diamine (1:1 equivalents epoxy to amine) was then added. With a water content of <0.1% the reaction mixture was heated to 120 to 140° C., and the reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 7

[0222] Reaction of Epoxidised Methyl Soyate with 500 Molecular Weight Allyl Alcohol Ethoxylate

[0223] 132.3 grams of epoxidised soyate with an epoxide value of 210 mg KOH/g was placed into a flask. 267.9 grams of 500 molecular weight allyl alcohol ethoxylate (1:1 equivalents epoxy to hydroxy) was added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 80° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g.

Example 8

[0224] Derivatisation of Example 3 by Transesterification of the Ester Group with a Methyl Initiated Poly Ethylene Glycol of 500 Molecular Weight (MPEG500)

[0225] 231.5 grams of example 3 was placed in a flask. 168.5 grams of MPEG500 was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 1% of 20% sodium methoxide catalyst was then added, and vacuum was applied to distil the methanol from the catalyst and by-product from the reaction. The reaction mixture was slowly heated to a maximum of 90° C. until distillation stopped.

Example 9

[0226] Derivatisation of Example 3 by Transesterification of the Ester Group with a Methyl Initiated Poly Ethylene Glycol of 1000 Molecular Weight (MPEG1000)

[0227] 162.9 grams of example 3 was placed in a flask. 237.1 grams of MPEG1000 was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 1% of 20% sodium methoxide catalyst was then added, and vacuum was applied to distil the methanol from the catalyst and by-product from the reaction. The reaction mixture was slowly heated until distillation stopped.

Example 10

[0228] Derivatisation of Example 3 by Amidation of the Ester Group with a Butyl Initiated Polyethylene/Polypropylene Glycol of 2000 Molecular Weight Polyether Amine

[0229] 102.2 grams of example 3 was placed in a flask. 297.8 grams of polyether amine was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 1% of 20% sodium methoxide catalyst was then added, and vacuum was applied to distil the methanol from the catalyst and by-product from the reaction. The reaction mixture was slowly heated to a maximum of 90° C. until distillation stopped.

Example 11

[0230] Derivatisation of Example 5 by Transesterification of the Ester Group with a Butyl Initiated Polypropylene Glycol of 1200 Molecular Weight (BPPG1200)

[0231] 150.3 grams of example 3 was placed in a flask. 249.7 grams of BPPG1200 was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 1% of 20% sodium methoxide catalyst was then added, and vacuum was applied to distil the methanol from the catalyst and by-product from the reaction. The reaction mixture was slowly heated to a maximum of 90° C. until distillation stopped.

Example 12

[0232] Derivatisation of Example 3 by Amidation of the Ester Group with Diethanolamine

[0233] 102.2 grams of example 3 was placed in a flask. 297.8 grams of diethanolamine was then added. The mixture was dried to a water content of <0.1%, then cooled to 60° C. 1% of 20% sodium methoxide catalyst was then added, and vacuum was applied to distil the methanol from the catalyst and by-product from the reaction. The reaction mixture was slowly heated to a maximum of 90° C. until distillation stopped. The reaction mixture was then allowed to equilibrate at 60° C. for 3 hours.

Example 13

[0234] Derivatisation of Example 7 by Sulfonation Using Sodium Bisulfite

[0235] 89.9 grams of example 7 was placed in a flask with 279.5 grams of water. 29.5 grams of sodium metabisulfite was then added with 1.1 grams of a 50% sodium hydroxide solution, and the reaction mixture was slowly heated to 90-95° C. The reaction was monitored by anionic surfactant content and was continued until the value became constant.

Example 14

[0236] Derivatisation of Example 1 by Amidation of the Ester Group with Dimethylaminopropylamine (DMAPA)

[0237] 312.4 grams of example 1 was placed in a flask and dried to <0.1% water content. 87.6 grams of DMAPA was then added (10% molar excess). The temperature was adjusted to 60° C., then 1% of 20% sodium methoxide catalyst was added, and the reaction mixture was slowly heated to 140° C. to distil the methanol from the catalyst and by-product from the reaction until distillation stopped. Once methanol distillation stopped, vacuum was applied and the reaction mixture was heated to 150° C. until the distillation of the excess DMAPA was complete.

Example 15

[0238] Derivatisation of Example 14 to Form a Betaine by Reaction with Monochloroacetic Acid

[0239] 110 grams of example 14 was charged to a flask along with 264.9 grams of water. 25.1 grams of monochloroacetic acid was then added. The pH was adjusted to 9.5-10.5 with 50% sodium hydroxide solution, and the reaction mixture was heated to 85° C. With the pH being maintained in the range 9.5-10.5, the reaction was continued until the base value was constant and <5.0 mg KOH/g.

Example 16

[0240] Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 200 Molecular Weight

[0241] 221.1 grams of epoxidised soyate with an epoxide value of 227 mg KOH/g was placed into a flask. 178.9 grams of 200 molecular weight polyethylene glycol (1:2 equivalents epoxy to hydroxy) was then added. The mixture was dried to a water content of <0.1%, then cooled to 20° C. 0.32 grams of boron tetrafluoride etherate catalyst was added, and the reaction was cooled to maintain the temperature below 60° C. The reaction was continued until the epoxide value of the mixture was <1 mg KOH/g. The final product had a saponification value of 129.2 mg KOH/g. 110 grams of this material was dispersed in 277.8 grams of water, and 12.2 grams of sodium hydroxide (a 20% molar excess of the quantity required for full hydrolysis) was then added. This mixture was heated to 95° C. for 12 hours, after which the reaction mixture was neutralized to pH 10.5 with acetic acid.