Cross-linked composition and method of forming the same

Patent metadata

Field	Value
Publication number	US-2016200876-A1
Application number	US-201414912177-A
Country	US
Kind code	A1
Filing date	Oct 29, 2014
Priority date	Oct 31, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A cross-linked composition comprises the reaction product of siloxanes having pendant anhydride groups and a reactant having hydroxyl and/or amine functional groups. The cross-linked composition can be of the following general formula (I): (I). Refer to formula ( 1 ) Each X can be of the following general formula (i): (i). Refer to formula (i) Each of W and W* is independently an oxygen atom or N—R, with R independently being a hydrogen atom or R 1 . Each of Y, R 3 , and R 13 is an independently selected divalent group. Each of R 1 , R 11 , R 4 , R 14 , R 5 , and R 15 is an independently selected substituted or unsubstituted hydrocarbyl group. Each of w and ww, and each of y and yy, is an independently selected integer from 0 to 1,000. Each of x and xx is an independently selected integer from 1 to 100. Typically, w and y are not simultaneously 0, and ww and yy are not simultaneously 0.

First claim

1 . A cross-linked composition comprising the reaction product of:
a first siloxane having at least one pendant anhydride group; a second siloxane having at least one pendant anhydride group; and a reactant comprising an organic polyol having at least two hydroxyl groups reactive with the pendant anhydride groups of said first and second siloxanes.

2 . A cross-linked composition comprising the reaction product of:
a first siloxane having at least one pendant anhydride group; a second siloxane having at least one pendant anhydride group; and a reactant selected from the group of; i) an organic polyol having at least two hydroxyl groups reactive with the pendant anhydride groups of said first and second siloxanes, ii) an organic polyamine having at least two amine groups reactive with the pendant anhydride groups of said first and second siloxanes, iii) a third siloxane having at least two hydroxyl groups reactive with the pendant anhydride groups of said first and second siloxanes, iv) a third siloxane having at least two amine groups reactive with the pendant anhydride groups of said first and second siloxanes, or v) combinations thereof.

3 . The cross-linked composition as set forth in claim 1 , wherein:
i) said organic polyol has two terminal hydroxyl groups; ii) said organic polyol is free of silicon; or iii) both i) and ii).

4 . The cross-linked composition as set forth in claim 2 , wherein:
i) said organic polyamine has two terminal amine groups; and/or ii) said third siloxane has two terminal hydroxyl groups; and/or iii) said third siloxane has two terminal amine groups.

5 . The cross-linked composition as set forth in claim 1 , wherein each of said first and second siloxanes comprise at least one [SiR 1 R 2 —O—] unit, R 1 is an independently selected substituted or unsubstituted hydrocarbyl group, R 2 is a pendant anhydride group of the following general formula (A):

and R 3 is a divalent group.

6 . The cross-linked composition as set forth in claim 5 , wherein each of said first and second siloxanes is individually of the following general formula (B):
R 5 3 Si—O—[SiR 1 R 4 —O—] w [SiR 1 R 2 —O—] x [SiR 1 R 4 —O—] y SiR 5 3   (B);
each of R 1 and R 2 are as defined above, alternatively each R 1 is an independently selected alkyl group; R 3 is a hydrocarbylene, heterohydrocarbylene, or organoheterylene group, alternatively R 3 is (CH 2 ) n where n is an integer selected from 1 to 30; R 4 is a substituted or unsubstituted hydrocarbyl group, alternatively R 4 is an independently selected alkyl group, aryl group, or (R 6 O) m group where R 6 is an alkyl group or aryl group and m is an integer selected from 1 to 50; each R 5 is an independently selected substituted or unsubstituted hydrocarbyl group, alternatively each R 5 is R 1 ; w is an integer selected from 0 to 1,000, alternatively 1 to 300; x is an integer selected from 1 to 100, alternatively 1 to 75; and y is an integer selected from 0 to 1,000, alternatively 1 to 300; with the proviso that w and y are not simultaneously 0.

7 . The cross-linked composition as set forth in claim 6 , wherein each of said first and second siloxanes is individually of the following general formula (B1):
(CH 3 ) 3 Si—O—[Si(CH 3 ) 2 —O—] w [Si(CH 3 )R 2 —O—] x [Si(CH 3 )R 4 —O—] y Si(CH 3 ) 3   (B1);
R 3 of R 2 is (CH 2 ) n where n is an integer selected from 1 to 15, alternatively 3; R 4 is an independently selected alkyl group having from 2 to 20 carbon atoms; w is an integer selected from 50 to 200, alternatively 75 to 125; x is an integer selected from 1 to 50, alternatively 1 to 5; and y is an integer selected from 1 to 200, alternatively 1 to 5.

8 . The cross-linked composition as set forth in claim 1 , wherein said reactant comprises said organic polyol and said organic polyol:
i) has the following general formula: HO—R 7 —OH; where R 7 comprises at least one of a hydrocarbylene, a heterohydrocarbylene, or an organoheterylene group, alternatively is a hydrocarbylene group having from 1 to 40 carbon atoms, alternatively 1 to 10 carbon atoms; or ii) is a polyether diol.

9 . The cross-linked composition as set forth in claim 2 , wherein said reactant comprises said organic polyamine and said organic polyamine:
i) has the following general formula: R 2 N—R 7 —NR 2 ; where each R is independently a hydrogen atom (H) or R 1 , alternatively an H; and R 7 comprises at least one of a hydrocarbylene, a heterohydrocarbylene, or an organoheterylene group; or ii) is a polyether diamine.

10 . The cross-linked composition as set forth in claim 2 , wherein said reactant comprises said third siloxane and said third siloxane is a polysiloxane of the following general formula:
i) HO—[Z] d —[SiR 8 R 10 —O—] a [SiR 8 R 9 —O—] b [SiR 8 R 10 —O—] c Si—[Z] d —OH   (C1); or
ii) R 2 N—[Z] d —[SiR 8 R 10 —O—] a [SiR 8 R 9 —O—] b [SiR 8 R 10 —O—] c Si—[Z] d —NR 2   (C2);
wherein each R is independently a hydrogen atom (H) or R 1 , alternatively each R is an H; each of R 8 , R 9 , and R 10 is an independently selected substituted or unsubstituted hydrocarbyl group; each Z independently comprises at least one of a hydrocarbylene, heterohydrocarbylene, or organoheterylene group, alternatively each Z is a hydrocarbylene group having from 1 to 20 carbon atoms; a is an integer selected from 0 to 1,000; b is an integer selected from 1 to 200; c is an integer selected from 0 to 1,000, alternatively 0 to 400; and each d is independently 0 or 1, alternatively 1.

11 . The cross-linked composition as set forth in claim 2 , wherein said reactant comprises said third siloxane and said third siloxane is a resin of general formula: R* s SiO (4-s)/2 ; where R* is an independently selected substituted hydrocarbyl group, unsubstituted hydrocarbyl group, hydroxyl group, or amine group, and s is from 0 to 3.

12 . A cross-linked composition of the following general formula (I):

wherein X is of the following general formula (i);

each of W and W* is independently an oxygen atom (O) or N—R, with R independently being a hydrogen atom (H) or R 1 ; each Y is a divalent group; each of R 1 , R 11 , R 4 , R 14 , R 5 , and R 15 is an independently selected substituted or unsubstituted hydrocarbyl group; each of R 3 and R 13 is an independently selected divalent group; each of w and ww is an independently selected integer from 0 to 1,000; each of x and xx is an independently selected integer from 1 to 100; and each of y and yy is an independently selected integer from 0 to 1,000; with the provisions that w and y are not simultaneously 0, and ww and yy are not simultaneously 0.

13 . (canceled)

14 . The cross-linked composition as set forth in claim 12 , wherein each of R 1 and R 11 is an independently selected alkyl group; R 3 is (CH 2 ) n where n is an integer selected from 1 to 30, alternatively 1 to 15; R 13 is (CH 2 ) nn where nn is an integer selected from 1 to 30, alternatively 1 to 15; each R 4 is an independently selected alkyl group, aryl group, or (R 6 O) m group where R 6 is an alkyl group or aryl group and m is an integer selected from 1 to 50, alternatively each R 4 is an independently selected alkyl group having from 2 to 20 carbon atoms; each R 14 is an independently selected alkyl group, aryl group, or (R 16

Assignees

• Dow Corning

Inventors

• Kadlec Donald A
• Nguyen Kimmai T
• Zimmerman Kenneth E

Classifications

• A61K2800/10

  General cosmetic use · CPC title

• C08G77/38 Primary

  Polysiloxanes modified by chemical after-treatment · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• C08L83/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers · CPC title

• C08L83/06

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