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. A method of preparing a surfactant, the method comprising: step (i) reacting: (a) an epoxidised carboxylic acid ester; and (b) a compound of formula (I): ##STR00008## wherein n is 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; and step (ii) reacting the reaction product of step (i) with (c) a derivatising agent comprising an alkoxy polyalkylene glycol, an alkoxy polyalkylene glycol amine, an alkyl amine, a dialkyl amine, an alkanolamine, a dialkanolamine or a sulfonating agent.

2. The method according to claim 1 wherein the epoxidised carboxylic acid ester is 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.

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

4. The method of claim 2 wherein R.sup.1 is methyl.

5. The method according to claim 1 wherein the epoxidised carboxylic acid ester is derived from soybean oil fatty acid.

6. The method according to claim 1 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.

7. The method according to claim 1 (iii) further comprising reacting the reaction product of step (ii) with (d) a quaternising agent.

8. The method of claim 1 wherein the weight/weight ratio of components (a) and (b) is of from 5:1 to 1:20.

9. The method of claim 1 wherein the step (i) reaction occurs under anhydrous conditions.

10. The method of claim 1 wherein the step (i) reaction occurs in the presence of a Lewis acid catalyst.

11. The method of claim 10 wherein the catalyst is boron trifluoride or boron trichloride.

12. The method of claim 1 wherein the step (i) reaction occurs at a temperature between 80° C. and 20° C.

13. A surfactant made by the method according to claim 1.

14. A method of reducing a surface tension at an interface, the method comprising applying a composition to the interface, the composition comprising the surfactant according to claim 13.

15. A composition comprising the surfactant of claim 13 and a diluent or carrier.

16. The composition according to claim 15 further comprising an ingredient selected from the group consisting of an ink, a paint, a pigment, a dispersant, a detergent, a lubricant, a fuel, an agrochemical, a coating, a cosmetic and an emulsion polymer.

Description

EXAMPLES

Example 1

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

(2) 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

(3) Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 200 Molecular Weight

(4) 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

(5) Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 600 Molecular Weight

(6) 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

(7) Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 1500 Molecular Weight

(8) 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

(9) Reaction of Epoxidised Methyl Soyate with Polytetrahydrofuran 650 Molecular Weight

(10) 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

(11) Reaction of Epoxidised Methyl Soyate with a 400 Molecular Weight Polyether Diamine Based on Polypropylene Glycol

(12) 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

(13) Reaction of Epoxidised Methyl Soyate with 500 Molecular Weight Allyl Alcohol Ethoxylate

(14) 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

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

(16) 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

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

(18) 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

(19) Derivatisation of Example 3 by Amidation of the Ester Group with a Butyl Initiated Polyethylene/Polypropylene Glycol of 2000 Molecular Weight Polyether Amine

(20) 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

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

(22) 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

(23) Derivatisation of Example 3 by Amidation of the Ester Group with Diethanolamine

(24) 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

(25) Derivatisation of Example 7 by Sulfonation Using Sodium Bisulfite

(26) 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

(27) Derivatisation of Example 1 by Amidation of the Ester Group with Dimethylaminopropylamine (DMAPA)

(28) 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

(29) Derivatisation of Example 14 to Form a Betaine by Reaction with Monochloroacetic Acid

(30) 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

(31) Reaction of Epoxidised Methyl Soyate with Polyethylene Glycol 200 Molecular Weight

(32) 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.