Claims
- 1. A method for preparing silicone-modified amidoamine compositions having the formula I: wherein:R10 is the silicone backbone chain to which at least one pyrrolidone containing amidoamine derivative of a pyrrolidone containing carboxyl functional group as shown is attached; R6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon atoms each, or cycloalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 10 carbon atoms within the oxyalkylene unit; R7 and R8, which may be the same or different, are selected from alkyl of up to 6 carbon atoms, hydroxyalkyl of up to 6 carbon atoms, cycloalkyl of up to 6 carbon atoms, carboxyalkyl of up to 6 carbon atoms or polyoxalkylene of up to 10 carbon atoms; or in addition R7 and R8 taken together with the nitrogen to which they are attached can represent an N-heterocycle; F1 is linear or branched alkylene of 1-12 carbon atoms; F is linear or branched alkylene of 2-10 carbon atoms; n3 is at least 1; n2 is 0 or 1, B is —NR9, wherein R9 is hydrogen or lower alkyl of 1-6 carbon atoms; and d is at least one; comprising the step of: a) reacting an organosilicone composition having at least one primary amine functional group with itaconic acid or an ester derivative thereof at an elevated temperature for a time sufficient to react substantially all the itaconic acid or ester derivative thereof with the functional primary amine group(s) on the silicone composition to form an organosilicone composition having at least one pyrrolidone containing carboxyl functional group of formula II: wherein R5 is hydrogen, lower alkyl (C1-6) or alkali metal, and R10, F1, F, B and n2 are defined as above; and b) reacting the carboxyl-containing silicone reactant of the formula II with an amine reactant of formula III: to form the silicone-modified amidoamine compositions of formula I; wherein R6, R7, R8, and n3 are defined as above; and further wherein mole ratio of the amine reactant to the carboxyl-containing silicone reactant is from 1:0.8 to 1:1.2 on a mole basis.
- 2. The method of claim 1 wherein said organosilicone composition of formula II and said itaconic acid or ester derivative thereof are uniformly dispersed with one and the other to form a homogeneous reaction mixture therewith.
- 3. The method of claim 1 wherein reaction of said organosilicone composition of formula II and itaconic acid or ester is carried out at a temperature from about 90° C. to about 130° C.
- 4. The method of claim 1 wherein said organosilicone composition of formula II has one or more terminal or lateral primary amine functional groups.
- 5. The method of claim 1 wherein the itaconic acid has the formula ofCH2═C(COOR9)CH2COOR9 wherein R9, which can be the same different, is hydrogen or lower alkyl of 1-6 carbon atoms.
- 6. The method of claim 1, wherein the silicone backbone chain, R10, is represented by the formula of: wherein:R1, which can be the same or different, is selected from R2, H, OR11, a primary amine containing group or a pyrrolidone containing carboxyl functional group or ester derivative thereof provided that at least one R1 is the pyrrolidone containing carboxyl functional group or ester derivative thereof as shown; R11 is H or lower alkyl (C1-6); R2 can be the same or different and is selected from alkyl, aryl or olefinic; R3 and R4, which may be the same or different are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene or alkenyl; a is an integer from 0 to 50,000; and b is an integer from 0 to 100.
- 7. The method of claim 6 wherein at least one of said R1 is OR11.
- 8. The method of claim 1 wherein F1 is a C1 alkylene, n2 is 0, and F is a C2 alkylene.
- 9. The method of claim 1 wherein F1 is a C1 alkylene, n2 is 0, and F is a branched C3 alkylene.
- 10. The method of claim 1 wherein F1 is a linear C3 alkylene or a branched C4 alkylene, n2 is 1, R9 is hydrogen, and F is a C2 alkylene.
- 11. A method of using a personal care or cosmetic composition comprising applying said composition to skin or hair of a person; wherein said composition comprises at least 0.1% of a polysiloxane composition having the formula wherein:R1, which can be the same or different, is selected from R2, an amine or a diamine containing group of the formula —F1—Bn2—F—NH2, —OR11 or a pyrrolidone-containing functional carboxyl group of the general formula: wherein at least one R1 is a pyrrolidone containing functional carboxyl group or derivative thereof as shown; R2 is as defined below; R5 is hydrogen, lower alkyl (C1-6) or alkali metal; F1 is linear or branched alkylene of 1-12 carbon atoms; F is linear or branched alkylene of 1-10 carbon atoms; n2 is 0 or 1, B is —NR9, wherein R9 is hydrogen or lower alkyl (C1-6); R2 can be the same or different and is selected from alkyl, aryl or olefinic; R3 and R4, which may be the same or different are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene or alkenyl; R11 is H or lower alkyl (C1-6); a is an integer from 0 to 50,000; and b is an integer from 0 to 100.
- 12. A polysiloxane composition having the formula wherein:R1, which can be the same or different, is selected from R2; an amine or a diamine containing group of the formula —F1—Bn2—F—NH2, —OR11 or a pyrrolidone-containing functional carboxyl group of the general formula: wherein at least one R1 is a pyrrolidone containing functional carboxyl group or derivative thereof as shown; at least one other R1 is —OR11; R2 is as defined below; R5 is hydrogen, lower alkyl (C1-6) or alkali metal; F1 is linear or branched alkylene of 1-12 carbon atoms; F is linear or branched alkylene of 1-10 carbon atoms; n2 is 0 or 1, B is —NR9, wherein R9 is hydrogen or lower alkyl (C1-6); R2 can be the same or different and is selected from alkyl, aryl or olefinic; R3 and R4, which may be the same or different are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene or alkenyl; R11 is H or lower alkyl (C1-6); a is an integer from 0 to 50,000; and b is an integer from 0 to 100.
- 13. The composition of claim 12 wherein F1 is a C1 alkylene, n2 is 0, and F is a C2 alkylene.
- 14. The composition of claim 12 wherein F1 is a C1 alkylene, n2 is 0, and F is a branched C3 alkylene.
- 15. The composition of claim 12 wherein F1 is a linear C3 alkylene or a branched C4 alkylene, n2 is 1, R9 is hydrogen, and F is a C2 alkylene.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation in part of application Ser. No. 09/167,167, filed Oct. 6, 1998, now U.S. Pat. No. 6,228,967, which is a continuation-in-part of application Ser. No. 08/651,730, filed May 22, 1996, now U.S. Pat. No. 5,817,730, both of which are incorporated by reference herein.
US Referenced Citations (36)
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
09/167167 |
Oct 1998 |
US |
Child |
09/850302 |
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US |
Parent |
08/651730 |
May 1996 |
US |
Child |
09/167167 |
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US |