Curable siloxane compositions

Patent metadata

Field	Value
Publication number	US-9771459-B2
Application number	US-201615052156-A
Country	US
Kind code	B2
Filing date	Feb 24, 2016
Priority date	Feb 25, 2015
Publication date	Sep 26, 2017
Grant date	Sep 26, 2017

Abstract

There is provided herein a curable polysiloxane composition comprising a reactive polysiloxane having the general structural formula (I):

as described herein. There is provided a method of making the polysiloxane. In addition there is provided a curable composition including the polysiloxane.

First claim

The invention claimed is:

1. A polysiloxane having the general structural formula (I):

wherein
each occurrence of R 1 , R 2 and R 3 is independently a linear or branched aliphatic group containing up to about 20 carbon atoms, an unsubstituted or substituted aryl group containing from about 6 to about 18 carbon atoms, optionally containing at least one heteroatom, and an alicyclic group containing up to about 20 carbon atoms;
each occurrence of R 4 is independently a divalent alkyl group of from about 1 to about 6 carbon atoms, a divalent unsubstituted or substituted aryl group containing up to about 18 carbon atoms, a divalent unsubstituted or substituted alicyclic group containing up to about 18 carbon atoms, a divalent unsubstituted or substituted acyl group containing up to about 18 carbon atoms, a divalent ester group containing up to about 8 carbon atoms, or a divalent ether group containing up to about 8 carbon atoms;
each occurrence of Z is independently selected from a divalent linear, branched or cyclic alkyl group containing from about 2 to about 25 carbon atoms, a divalent linear, branched or cyclic alkenyl group containing from about 2 to about 25 carbon atoms, and a divalent unsubstituted or substituted aryl group of up to about 20 carbon atoms;
each occurrence of M is independently a hydroxy group, an alkynyl group of from about 2 to about 12 carbon atoms, an amino group, an alkoxy group containing from about 1 to about 8 carbon atoms, an alkoxyalkyl group containing from about 2 to about 10 carbon atoms, an oximoalkyl group containing up to about 8 carbon atoms, an enoxyalkyl group containing up to about 8 carbon atoms, an aminoalkyl group containing up to about 8 carbon atoms, a carboxyalkyl group containing up to about 8 carbon atoms, an amidoaliphatic group containing up to about 8 carbon atoms, an amidoaryl group containing up to about 12 carbon atoms, a carbamato alkyl group containing up to about 8 carbon atoms, an anhydride group, a carboxyl group containing up to about 8 carbon atoms, a carbonyl group, an acyl group containing up to about 8 carbon atoms, an amide group, an ionic group, an imine group containing up to about 8 carbon atoms, an isocyanate group, a nitrile group, an (meth)acryl group, an (meth)acrylol group, an alkoxysilyl group, an alkoxyalkylsilyl group, an acyloxysilyl group, a hydroxyalkylsilyl group or a thiol group; and
the subscript x is an integer of from 1 to 250, the subscript y is an integer from 0 to 100, the subscript n′ is an integer from 2 to 10,000, and the subscript m is an integer of from to 1 to 5.

2. A method of preparing the polysiloxane compound (I) of claim 1 , comprising:
hydrosilylating a hydride terminated polysiloxane represented by the general structural formula (III)

each R 1 , R 2 , R 3 , x and y are as defined in claim 1 ,
with a diene which contains a linear, branched or cyclic alkyl group containing from about 2 to about 25 carbon atoms or a linear, branched or cyclic alkylene group of from about 2 to about 25 carbon atoms to obtain a hydride-terminated polysiloxane represented by the structural formula (IV):

wherein each of R 1 , R 2 , R 3 , y and n′ are as defined in claim 1 ,
followed by hydrosilylation of the hydride-terminated polysiloxane of formula (IV) with an unsaturated compound of the general formula (V):

wherein R 4* is chosen from an alkenyl group containing from about 2 to about 6 carbon atoms, an allyl acyl group containing up to about 8 carbon atoms, a vinyl acyl group containing, up to about 8 carbon atoms, an allyl carbonyloxy group of up to about 8 carbon atoms, an allyl phenyl group of up to about 18 carbon atoms, a vinyl phenyl group of up to about 18 carbon atoms, an allyl ether group of up to about 8 carbon atoms, or a vinyl ether group of up to about 8 carbon atoms, wherein one or more of such R4* groups can optionally contain one or more of a hydroxyl group, an alkoxy group of from about 1 to about 4 carbon atoms, or a heteroatom; M is as defined in claim 1 , and the subscript in is an integer of from 1 to 5, and wherein when the subscript m=1, the R 4* groups are terminal groups, and when the subscript m is >1 then the R 4* groups comprise at least one divalent group and one terminal group.

3. A curable composition comprising at least one polysiloxane according to claim 1 .

4. An article comprising the polysiloxane of claim 1 .

5. An elastomer, a sealant, an adhesive, a coating or a combination thereof comprising the curable composition of claim 3 , wherein the curable composition is cured.

6. The polyslioxane of claim 1 , wherein M is a hydroxy group, an aminoalkyl group containing up to about 8 carbon atoms, an anhydride group, an isocyanate group, an alkoxysilyl group, an alkoxyalkylsilyl group, an acyloxysilyl group or a thiol group.

7. The polysiloxane of claim 1 , wherein n′ is from 2 to 35.

8. The polysiloxane of claim 1 , wherein n′ is, from 2 to 4.

9. The polysiloxane of claim 1 , wherein x is from 1 to 50.

10. The polysiloxane of claim 1 , wherein x is from 1 to 15.

11. The polysiloxane of claim 1 , wherein x is from 15 to 30.

12. The polysiloxane of claim 1 , wherein y is from 1 to 8.

13. The polysiloxane of claim 1 , wherein y is 0.

14. The polysiloxane of claim 1 , wherein m is 1.

15. The polysiloxane of claim 1 , wherein each R 1 d R 2 is an alkyl of from 1 to 4 carbon atoms.

16. The polysiloxane of claim 1 , wherein each R 1 and R 2 is a methyl group.

17. The polysiloxane of claim 1 , wherein R 3 is a phenyl group.

18. The polysiloxane of claim 1 , wherein Z is a divalent alkylene group from 6 to 10 carbon atoms.

19. The polysiloxane of claim 1 , wherein Z is a divalent octylene.

20. The article of claim 4 , wherein M is a hydroxy group, an aminoalkyl group containing up to about 8 carbon atoms, an anhydride group, an isocyanate group, an alkoxysilyl group, an alkoxyalkylsilyl group, an acyloxysilyl group or a thiol group.

21. The article of claim 4 , wherein n′ is from 2 to 35, x is 1 to 50 and y is 0 to 40.

22. The article of claim 4 , wherein n′ is from 2 to 4, x is 1 to 15 and y is 1 to 8.

23. The article of claim 4 , wherein each R 1 and R 2 is a methyl group, R 3 is a phenyl group and Z is a divalent alkylene group of from 6 to 10 carbon atoms.

24. The article of claim 4 , wherein m is 1.

Assignees

• Momentive Performance Mat Inc

Inventors

• Mittal Anuj
• Mathad Raveendra
• Dinkar Sumi
• Ramakrishnan Indumathi
• Gupta Manav

Classifications

• 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

• C09D183/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence) · CPC title

• C08L83/14

  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

• C08G77/12 Primary

  containing silicon bound to hydrogen · CPC title

• C09J183/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09J183/10 takes precedence) · CPC title