Curable siloxane compositions
View Patent ↗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.
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.