Cross-linked composition and method of forming the same

Patent metadata

Field	Value
Publication number	US-9822221-B2
Application number	US-201414912174-A
Country	US
Kind code	B2
Filing date	Oct 29, 2014
Priority date	Oct 31, 2013
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

A cross-linked composition comprises the reaction product of a first reactant having at least one hydroxyl or amine (functional) group, a second reactant having at least one hydroxyl or amine (functional) group, and a siloxane having at least two terminal anhydride groups reactive with the functional groups of the first and second reactants. The first reactant is selected from the group of first siloxanes having at least one hydroxyl or amine group, a first organic alcohol having at least one hydroxyl group, a first organic amine having at least one amine group, or combinations thereof. The second reactant is selected from the group of second siloxanes having at least one hydroxyl or amine group, a second organic alcohol having at least one hydroxyl group, a second organic amine having at least one amine group, or combinations thereof. If utilized, the first siloxanes and/or second siloxanes are different from the siloxane.

First claim

What is claimed is:

1. A cross-linked composition comprising the reaction product of:
a first reactant having at least two hydroxyl groups;
a second reactant having at least two hydroxyl groups; and
a siloxane having at least two terminal anhydride groups reactive with the hydroxyl groups of said first and second reactants;
wherein said first reactant is selected from the group of;
i) a first siloxane different from said siloxane and having at least two hydroxyl groups,
ii) a first organic alcohol having at least two hydroxyl groups, or
iii) a combination thereof; and
wherein said second reactant is selected from the group of;
i) a second siloxane different from said siloxane and having at least two hydroxyl groups,
ii) a second organic alcohol having at least two hydroxyl groups, or
iii) a combination thereof.

2. The cross-linked composition as set forth in claim 1 , wherein:
i) said first reactant comprises said first siloxane having at least two hydroxyl groups, alternatively at least two pendant hydroxyl groups;
ii) said second reactant comprises said second siloxane having at least two hydroxyl groups, alternatively at least two pendant hydroxyl groups; or
iii) both i) and ii).

3. The cross-linked composition as set forth in claim 2 , wherein:
i) said first siloxane has at least three hydroxyl groups, alternatively at least three pendant hydroxyl groups;
ii) said second siloxane has at least three hydroxyl groups, alternatively at least three pendant hydroxyl groups; or
iii) both i) and ii).

4. The cross-linked composition as set forth in claim 1 , wherein:
i) said first reactant comprises said first organic alcohol having at least two hydroxyl groups, alternatively at least three hydroxyl groups;
ii) said second reactant comprises said second organic alcohol having at least two hydroxyl groups, alternatively at least three hydroxyl groups; or
iii) both i) and ii).

5. The cross-linked composition as set forth in claim 4 , wherein:
i) said first organic alcohol has at least one pendant hydroxyl group;
ii) said second organic alcohol has at least one pendant hydroxyl group; or
iii) both i) and ii).

6. The cross-linked composition as set forth in claim 1 , wherein said siloxane has two terminal anhydride groups.

7. The cross-linked composition as set forth in claim 1 , wherein said siloxane is of the following general formula (A):
R 7 R 5 2 Si—O—[SiR 1 R 4 —O-] w [SiR 1 R 2 —O-] x [SiR 1 R 4 —O-] y SiR 5 2 R 7   (A);

each R 7 is a terminal anhydride group of the following general formula (B):

each of R 1 , R 2 , R 4 , and R 5 is an independently selected substituted or unsubstituted hydrocarbyl group, alternatively R 1 is an independently selected alkyl group, alternatively R 4 is an independently selected alkyl group, aryl group, or polyether group having from 2 to 49 ether linkages and terminated with —OR 6 , wherein R 6 is an alkyl group or aryl group, and/or alternatively R 5 is R 1 ; R 3 is a divalent group, alternatively R 3 is (CH 2 ) n where n is an integer selected from 1 to 30; w is an integer selected from 0 to 1,000, alternatively 0 to 300; x is an integer selected from 0 to 100, alternatively 0 to 75; and y is an integer selected from 0 to 1,000, alternatively 0 to 300.

8. The cross-linked composition as set forth in claim 7 , wherein said siloxane is of the following general formula (A1):
R 7 (CH 3 ) 2 Si—O—[Si(CH 3 ) 2 —O—] w [Si(CH 3 ) 2 —O—] x [Si(CH 3 )R 4 —O—] y Si(CH 3 ) 2 R 7   (A1);

R 3 of R 7 is (CH 2 ) n where n is an integer selected from 1 to 15, alternatively 3; R 4 is an independently selected alkyl having from 2 to 20 carbon atoms; w is an integer selected from 0 to 200, alternatively 0 to 125; x is an integer selected from 0 to 50, alternatively 0 to 5; and y is an integer selected from 0 to 200, alternatively 0 to 5.

9. The cross-linked composition as set forth in claim 1 , wherein each of said first and second siloxanes is individually of the following general formula (C):
R 11 3 Si—O—[SiR 8 R 10 —O-] a [SiR 8 R 9 —O-] b [SiR 8 R 10 —O-] c SiR 11 3   (C);

each R 9 is of the following formula (D):
—[Z] d —V  (D);

V is OH; Z is a divalent group, alternatively Z comprises at least one of a hydrocarbylene, heterohydrocarbylene, or organoheterylene group; each of R 8 and R 11 is an independently selected substituted or unsubstituted hydrocarbyl group, alternatively each of R 8 and R 11 is an independently selected alkyl group; each R 10 is an independently selected alkyl group, aryl group, or polyether group having from 2 to 49 ether linkages and terminated with —OR 6 , wherein R 6 is an alkyl group or aryl group; 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; and each d is independently 0 or 1, alternatively 1.

10. The cross-linked composition as set forth in claim 9 , wherein d is 1 and Z comprises at least one structural unit selected from the group consisting of:
i) [(CH 2 ) i ] k ;
ii) [(CH 2 ) i O] k ;
iii) [(CH 2 ) i (CH)(CH 3 )O] k ;
iv) [(CH 2 ) i (CH)(CH 2 ) j (CH 3 )O] k ;
v) [(CH)OH] k ;
vi) [(CH)(CH 2 ) i OH] k ;
vii) [(CH 3 ) 2 COH(CH 2 ) i ] k ;
viii) [(CH 3 )(CH 2 ) i COH(CH 2 ) j (CH 3 )] k ;
ix) [(CH 2 ) i NH(CH 2 ) i ] k ;
x) [(CH 2 ) i N(CH 2 ) j (CH 3 )] k ; and
xi) combinations thereof;

where i is an integer selected from 1 to 100; j is an integer selected from 1 to 100; and k is an integer selected from 1 to 100.

11. The cross-linked composition as set forth in claim 1 , wherein each of said first and second siloxanes is individually a resin of the general formula R* S SiO (4-s)/2 where R* is an independently selected substituted hydrocarbyl group, unsubstituted hydrocarbyl group, or hydroxyl group, and s is from greater than 0 to 3.

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

13. The cross-linked composition as set forth in claim 12 , wherein each of said organic alcohols independently has the following general formula: HO—R 8 —OH; where R 8 is a hydrocarbylene group having from 1 to 40 carbon atoms, alternatively 1 to 10 carbon atoms.

14. The cross-linked composition as set forth in claim 1 , wherein each of said organic alcohols is free of silicon.

15. The cross-linked composition as set forth in claim 1 , having free carboxyl groups provided by said siloxane and optionally, a carboxyl equivalent of from 100 to 50,000 g/mol.

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

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

each Y is of the following formula (ii);
—SiR 5 2 —O—[SiR 1 R 4 —O—] w [SiR 1 R 2 —O—] x [SiR 1 R 4 —O—] y SiR 5 2 —  (ii);

each of W and W* is an oxygen atom (O); each of Z, R 3 , and R 13 is an independently selected divalent group, alternatively Z comprises at least one of a hydrocarbylene, heterohydrocarbylene, or organoheterylene group; each of R 1

Assignees

• Dow Corning

Inventors

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

Classifications

• C08G77/48 Primary

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08G77/42 takes precedence) · CPC title

• C08G77/26

  nitrogen-containing groups · CPC title

• C08L83/14 Primary

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence) · CPC title

• C08G77/54

  Nitrogen-containing linkages · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title