Ester modified cross-linked silicone compositions

Patent metadata

Field	Value
Publication number	US-12018150-B2
Application number	US-202117321257-A
Country	US
Kind code	B2
Filing date	May 14, 2021
Priority date	May 18, 2020
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The present disclosures are directed to compositions comprising a polymer having linear or branched silicone substituted by at least one alkylcarboxy group and cross-linked with an alkyl functional cross-linker, which has the benefits of compatibility and structuring of personal care components and the resultant personal care applications.

First claim

What is claimed is:

1. A composition comprising a polymer having branched silicone substituted by at least one alkylcarbonylalkyl group and by at least one alkylcarboxy group, and cross-linked with an alkenyl functional cross-linker, wherein an average number of alkylcarboxyalkyl substitutions per silicone is between 1 and 60 and an average number of crosslinks between branched silicones is between 1 and 30.

2. The composition of claim 1 , wherein the average number of alkylcarboxyalkyl substitutions per silicone is between 1 and 15.

3. The composition of claim 1 , wherein the average number of crosslinks between branched silicones is between 1 and 15.

4. The composition of claim 1 , wherein the polymer is prepared by a method comprising reacting:
(a) a Si—H functional compound of formula (I):
M H a M b D H c D d T H e T f Q g   (I)

wherein:
M H =R 1 R 2 HSiO 1/2 ;
M=R 3 R 4 R 5 SiO 1/2 ;
D H =R 6 HSiO 2/2 ;
D=R 7 R 8 SiO 2/2 ;
T H HSiO 3/2 ;
T=R 9 SiO 3/2 ; and
Q=SiO 4/2 ;

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently an aliphatic, aromatic, or fluoro monovalent hydrocarbon having from 1 to 60 carbon atoms; and
a, b, c, d, e, f, and g are independently zero or a positive integer, such that 2≤a+b+c+d+e+f+g≤6000 and when a′+c′+e′=2, a+c+e>2 and wherein e+f+g≥1;

(b) a carboxy functional olefin of formula (II):

wherein
R′ is a combination of R 1 and —Si(R a ) 3 , wherein R 1 is a C 1 -C 60 monovalent hydrocarbon and R a is an aliphatic, aromatic, or fluoro monovalent hydrocarbon; and
n is 0≤n≤30; and

(c) a silicone based alkenyl functional cross-linker of formula (III) and/or a non-silicone based alkenyl functional cross-linker of formula (IV):
M 1 a′ M 2 b′ D 1 c′ D 2 d′ T 1 e′ T 2 f′ Q g′   (III)

wherein:
M 1 =R 10 R 11 R 12 SiO 1/2 ;
M 2 =R 13 R 14 R 15 SiO 1/2 O;
D 1 =R 16 R 17 SiO 2/2 ;
D 2 =R 18 R 19 SiO 2/2 ;
T 1 =R 20 SiO 3/2 ;
T 2 =R 21 SiO 3/2 ; and
Q=SiO 4/2 ;

wherein
R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 , are independently an aliphatic, aromatic, or fluoro monovalent hydrocarbon having from 1 to 60 carbon atoms;
R 10 , R 16 , and R 20 are each a monovalent radical containing at least one terminal olefin bond; a′, b′, c′, d′, e′, f′, and g′ are independently zero or a positive integer, such that 2≤a′+b′+c′+d′+e′+f+g′≤6000 and when a+c+e=2, a′+c′+e′>2; and

Z is —(CHR 22 ) m — or —(CH 2 CHR 23 O) k —, wherein m and k are positive integers, such that 1≤m≤60 and 1≤k≤500, and R 22 and R 23 are independently hydrogen or monovalent hydrocarbon having from 1 to 60 carbon atoms.

5. The composition of claim 4 , wherein the one or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is a C 1 -C 20 monovalent hydrocarbon.

6. The composition of claim 4 , wherein a, b, c, d, e, f, and g are 2≤a+b+c+d+e+f+g: ≤4000.

7. The composition of claim 4 , wherein one or more of R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 is a C 1 -C 30 monovalent hydrocarbon.

8. The composition of claim 4 , wherein one or more of R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 is an aromatic monovalent hydrocarbon.

9. The composition of claim 4 , wherein one or more of R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 is a fluoro monovalent hydrocarbon.

10. A method for preparing a polymer having branched silicone comprising reacting:
(a) a Si—H functional compound of formula (I):
M H a M b D H c D d T H e T f Q g   (I)

wherein:
M H =R 1 R 2 HSiO 1/2 ;
M=R 3 R 4 R 5 SiO 1/2 ;
D H =R 6 HSiO 2/2 ;
D=R 7 R 8 SiO 2/2 ;
T H =HSiO 3/2 ;
T=R 9 SiO 3/2 ; and
Q=SiO 4/2 ;

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently an aliphatic, aromatic, or fluoro monovalent hydrocarbon having from 1 to 60 carbon atoms; and
a, b, c, d, e, f, and g are independently zero or a positive integer, such that 2≤a+b+c+d+e+f+g≤6000 and when a′+c′+e′=2, a+c+e>2 and wherein e+f+g≥1;

(b) a carboxy functional olefin of formula (II):

wherein
R′ is a combination of R 1 and —Si(R a ) 3 , wherein R 1 is an aliphatic, aromatic, or fluoro monovalent hydrocarbon having from 1 to 60 carbon atoms and R a is an aliphatic, aromatic, or fluoro monovalent hydrocarbon, and;
n is 0≤n≤30; and

(c) a silicone based alkenyl functional cross-linker of formula (III) and/or a non-silicone based alkenyl functional cross-linker of formula (IV):
M 1 a′ ,M 2 b′ D 1 c′ D 2 d′ T 1 e′ T 2 f′ Q g′

wherein:
M 1 =R 10 R 11 R 12 SiO 1/2 ;
M 2 =R 13 R 14 R 15 SiO 1/2 ;
D 1 =R 16 R 17 SiO 2/2 ;
D 2 =R 18 R 19 SiO 2/2 ;
T 1 =R 20 SiO 3/2 ;
T 2 =R 21 SiO 3/2 ; and
Q=SiO 4/2 ;

wherein
R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 , are independently an aliphatic, aromatic, or fluoro monovalent hydrocarbon having from 1 to 60 carbon atoms;
R 10 , R 16 , R 20 and are each a monovalent radical containing at least one terminal olefin bond;
a′, b′, c′, d′, e′, f′, and g′ are independently zero or a positive integer, such that 2≤a′+b′+c′+d′+e′+f+g′≤6000 and when a+c+e=2, a′+c′+e′>2;
Z is —(CHR 22 ) m — or —(CH 2 CHR 23 O) k —, wherein m and k are positive integers, such that 1≤m≤60 and 1≤k≤500, and R 22 and R 23 are independently hydrogen or monovalent hydrocarbon having from 1 to 60 carbon atoms; and
wherein an average number of crosslinks between branched silicones is between 1 and 30.

11. The method of claim 10 , wherein one or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is a C 1 -C 20 monovalent hydrocarbon.

12. The method of claim 10 , wherein one or more R 11 , R 12 , R 13 , R 14 , R 15 , R 17 , R 18 , R 19 , and R 21 is a C 1 -C 60 monovalent hydrocarbon.

13. The method of claim 10 , wherein the reaction between the Si—H compound of formula (I), the carboxy functional olefin of formula (II) and the alkenyl functional cross-linker of formula (III) and/or (IV) occurs in the presence of at least one precious metal catalyst selected from the group consisting of a rhodium, ruthenium, palladium, osmium, iridium, iron and platinum catalyst.

14. A personal care composition comprising:
(a) the composition of claim 1 ; and
(b) one or more personal care components.

15. The composition of claim 4 , wherein the method further comprises deprotecting the silyl protected carboxylic acid.

16. The method of claim 10 , wherein the method further comprises deprotecting the silyl protected carboxylic acid.

17. The composition of claim 4 , wherein a=12; b, c, d, e, and f=0; and g=10.

18. The composition of claim 4 , wherein a=3; b, c, d, e, and g=0; and f=1.

Assignees

• Momentive Performance Mat Inc

Inventors

• Sarkar Alok
• Falk Benjamin
• KANDIKKAL Ashitha

Classifications

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C08L2312/00

  Crosslinking · CPC title

• C08G77/80

  Siloxanes having aromatic substituents, e.g. phenyl side groups · CPC title

• C08G77/24

  halogen-containing groups · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title