Claims
- 1. In a process for producing an antistatic composition wherein diethanolamine and monocarboxylic acid ester represented by the formula:
- RC(O)OR'
- are reacted in the presence of an excess of diethanolamine to produce a first reaction mixture comprising diethanol amide of monocarboxylic acid represented by the formula:
- RC(O)N(CH.sub.2 CH.sub.2 OH).sub.2
- the improvement wherein residual diethanolamine in said first reaction mixture and triglyceride represented by the formula:
- G[OC(O)R].sub.3
- are reacted to produce a second reaction mixture comprising said diethanol amide of monocarboxylic acid and hydroxy-functional glyceride selected from the group consisting of:
- (a) monoglyceride represented by the formula:
- G[OH].sub.2 [OC(O)R]
- (b) diglyceride represented by the formula:
- G[OH][OC(O)R].sub.2
- and
- (c) a mixture of said monoglyceride and said diglyceride,
- wherein G is 1,2,3-propanetriyl, each R is independently a hydrophobic hydrocarbon group, and R' is an alkyl group containing from 1 to about 18 carbon atoms.
- 2. The process of claim 1 wherein each said hydrophobic hydrocarbon group independently contains from about 7 to about 29 carbon atoms.
- 3. The process of claim 1 wherein each said hydrophobic hydrocarbon group is independently straight or branched alkyl containing from about 7 to about 29 carbon atoms, straight or branched alkenyl containing from about 9 to about 21 carbon atoms, straight or branched alkadienyl containing from about 13 to about 21 carbon atoms, or ##STR4## wherein each R" is independently straight or branched alkyl and the average value of n is in the range of from 0 to about 2.
- 4. The process of claim 1 wherein each said hydrophobic hydrocarbon group is independently a hydrophobic hydrocarbon group corresponding to that attached to the carboxyl group of a long chain monocarboxylic acid derived from the triglyceride of a natural fat or oil.
- 5. The process of claim 1 wherein each hydrophobic hydrocarbon group is undecyl.
- 6. The process of claim 1 wherein said alkyl group is methyl or ethyl.
- 7. The process of claim 1 wherein said alkyl group is methyl.
- 8. The process of claim 1 wherein the molar ratio of said hydroxy-functional glyceride to said diethanol amide in said second reaction mixture is in the range of from about 0.005:1 to about 0.5:1.
- 9. The process of claim 1 wherein both reactions are neat reactions.
- 10. The process of claim 1 wherein both reactions are conducted at temperatures in the range of from about 80.degree. C. to about 150.degree. C.
- 11. The process of claim 1 wherein both reactions are conducted in the presence of a catalytic amount of a basic catalyst.
- 12. The process of claim 1 wherein said basic catalyst is alkali metal alkoxide.
- 13. The process of claim 12 wherein said alkali metal alkoxide contains from 1 to about 18 carbon atoms.
- 14. The process of claim 12 wherein said alkali metal alkoxide is sodium methoxide.
- 15. The process of claim 1 wherein:
- (a) each R is undecyl;
- (b) R' is methyl;
- (c) both reactions are conducted in the presence of a catalytic amount of sodium methoxide;
- (d) both reactions are conducted at temperatures in the range of from about 80.degree. C. to about 85.degree. C.;
- (e) the first reaction is conducted under a vacuum with a nitrogen purge;
- (f) said second reaction mixture is substantially free of diethanolamine; and
- (g) The molar ratio of said hydroxy-functional glyceride to said diethanol amide in said second reaction mixture is in the range of from about 0.005:1 to about 0.5:1.
- 16. The process of claim 15 wherein the molar ratio of said hydroxy-functional glyceride to said diethanol amide in said second reaction mixture is in the range of from about 0.025:1 to about 0.1:1.
Parent Case Info
This is a divisional of application Ser. No. 07/498,194, filed Mar. 23, 1990 now U.S. Pat. No. 5,098,989.
US Referenced Citations (5)
Foreign Referenced Citations (2)
Number |
Date |
Country |
42-17561 |
Sep 1967 |
JPX |
384665 |
Dec 1932 |
GBX |
Non-Patent Literature Citations (1)
Entry |
L. W. Burnette, Nonionic Surfactants, (Edited by Martin J. Schick), 1967, pp. 396-403, 418-420. |
Divisions (1)
|
Number |
Date |
Country |
Parent |
498194 |
Mar 1990 |
|