IP Library Patent Application 11582933
Patent Application
App. No. 11/582,933

Process for producing polysiloxanes and use of the same

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Quick Facts
Patent No.
US None
App. No.
11/582,933
Abstract

A process for the preparation of an organosilicon condensate which comprises reacting together a silicon containing compound having at least one silanol group and a silicon containing compound having at least one —OR group or at least one silanol group (or a compound having both groups) in the presence of strontium oxide, barium oxide, strontium hydroxide or barium hydroxide and optionally a solvent such as water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and 2-butanol, acetone or toluene.

Claims (84)

1 . A process for the preparation of an organosilicon condensate that comprises reacting together:

at least one silicon containing compound (A) having at least one silanol group; and

at least one silicon containing compound (B) having at least one silicon bonded —OX group wherein X represents at least one chosen from a group comprising hydrogen, an alkyl group having from 1 to 8 carbon atoms, an alkoxyalkyl group having from 2 to 8 carbon atoms, wherein the reaction is in the presence of a catalyst (C) selected from a group comprising strontium oxide, barium oxide, strontium hydroxide, barium hydroxide and mixtures thereof, and at least one solvent (D) selected to allow the reaction to proceed.

2 . A process according to claim 1 wherein the organosilicon condensate is a siloxane or polysiloxane.

3 . A process according to claim 1 wherein (A) and (B) are independently monomeric, dimeric, oligomeric or polymeric compounds.

4 . A process according to claim 1 wherein (A) is a silanol having between one and three unsubstituted or substituted hydrocarbon groups having from 1 to 18 carbon atoms.

5 . A process according to claim 4 wherein the silanol is selected from a group comprising diphenyl silanediol, 4-vinyl-diphenyl silanediol and dipentafluorophenyl silanediol.

6 . A process according to claim 1 wherein (A) comprises a crosslinkable group.

7 . A process according to claim 6 wherein the crosslinkable group is selected from a group comprising an epoxide group, a double bond of the acrylate type, a double bond of the methacrylate type and a double bond of the styrene type.

8 . A process according to claim 1 wherein (B) is a monomeric compound with the general formula

G y Si(OR) 4-y

wherein y has a value of 0, 1, 2 or 3,

G represents an unsubstituted or substituted hydrocarbon group having from 1 to 18 carbon atoms; and

R represents an alkyl group having from 1 to 8 carbon atoms or an alkoxyalkyl group having from 2 to 8 carbon atoms.

9 . A process according to claim 8 wherein (B) is an alkoxysilane, which has from one to four alkoxy groups inclusive.

10 . A process according to claim 8 wherein OR is selected from a group comprising methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy and t-butoxy.

11 . A process according to claim 8 wherein R and G independently comprise a crosslinkable group.

12 . A process according to claim 11 wherein the crosslinkable group is selected from a group comprising an epoxide group, a double bond of the acrylate type, a double bond of the methacrylate type and a double bond of the styrene type.

13 . A process according to claim 8 wherein (B) is selected from a group comprising an propyltrimethoxysilane, hexyltrimethoxysilane, octyltrimethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, hexadecyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, phenylethyltrimethoxysilane, phenylpropyltrimethoxysilane, 3,3,3-trifluoro-propyltrimethoxysilane, nonafluoro-1,1,2,2-tetrahydrohexyl-trimethoxysilane, tridecafluoro-1,1,2,2-tetrahydrooctyl-trimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-styrylpropyltrimethoxysilane and 3-glycidoxypropyltrimethoxysilane.

14 . A process according to claim 1 wherein (B) is an oligomeric or polymeric compound of general formula

R 1 3 SiO(SiR 1 2 O) n SiR 1 2 OR

wherein R is chosen from a group comprising an alkyl group having from 1 to 8 carbon atoms and an alkoxyalkyl group having from 2 to 8 carbon atoms, n is an integer ≧0, and each R 1 is chosen from a group comprising an unsubstituted or substituted hydrocarbon group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 8 carbon atoms, and an alkoxyalkyl group having from 2 to 8 carbon atoms.

15 . A process according to claim 1 wherein (A) and (B) are each hydroxy-terminated siloxanes of general formula HO—(SiR 1 R 2 O) n —H

wherein R 1 and R 2 are chosen from a group comprising unsubstituted or substituted hydrocarbon groups having from 1 to 18 carbon atoms and n is an integer >0.

16 . A process according to claim 1 wherein the at least one solvent is present in an amount of from 0.02% to 200% by mole ratio based on the total silicon containing compounds.

17 . A process according to claim 1 wherein the at least one solvent comprises a protic solvent.

18 . A process according to claim 17 wherein the protic solvent is selected from a group comprising water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and 2-butanol.

19 . A process according to claim 18 wherein the protic solvent is water, employed in an amount less than 8% by mole ratio based on the total silicon containing compounds.

20 . A process according to claim 1 wherein the at least one solvent comprises a non-protic solvent.

21 . A process according to claim 1 wherein the catalyst is employed in an amount of from 0.0005 to 5% by mole ratio based on the total silicon containing compounds.

22 . A process according to claim 1 further comprising separation of the catalyst from the organosilicon condensate.

23 . A process according to claim 1 wherein the organosilicon condensate has a viscosity in the range from 1,000 to 4,000 cP.

24 . A process for the preparation of an organosilicon condensate comprising condensing at least one silicon containing compound having:

at least one silanol group (a);

and

at least one —OX group (b),

wherein X is chosen from a group comprising hydrogen, an alkyl group having from 1 to 8 carbon atoms, and an alkoxyalkyl group having from 2 to 8 carbon atoms in the presence of a catalyst (c) selected from a group comprising strontium oxide, barium oxide, strontium hydroxide, barium hydroxide and mixtures thereof, and

at least one solvent (d) selected to allow the reaction to proceed.

25 . A process according to claim 24 wherein the at least one solvent is present in an amount of from 0.02% to 200% by mole ratio based on the total silicon containing compounds.

26 . A process according to claim 24 wherein the at least one solvent comprises a protic solvent.

27 . A process according to claim 26 wherein the protic solvent is selected from a group comprising water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and 2-butanol.

28 . A process according to claim 27 wherein the protic solvent is water, employed in an amount less than 8% by mole ratio based on the total silicon containing compounds.

29 . A process according to claim 24 wherein the at least one solvent comprises a non-protic solvent.

30 . A process according to claim 24 wherein the catalyst is employed in an amount of from 0.0005 to 5% by mole ratio based on the total silicon containing compounds.

31 . A process according to claim 24 further comprising separation of the catalyst from the organosilicon condensate.

32 . A process according to claim 24 wherein the organosilicon condensate has a viscosity in the range from 1,000 to 4,000 cP.

33 . A process for the preparation of an organosilicon condensate comprising reacting together:

at least one silicon containing compound (A) having at least one silanol group;

and

at least one silicon containing compound (B) having at least one silicon bonded —OX group wherein X is chosen from a group comprising hydrogen, an alkyl group having from 1 to 8 carbon atoms, or an alkoxyalkyl group having from 2 to 8 carbon atoms in the presence of a catalyst (C) selected from a group comprising strontium oxide, barium oxide, strontium hydroxide, barium hydroxide and mixtures thereof.

34 . A process according to claim 33 wherein the catalyst is selected from a group comprising strontium oxide and barium oxide.

35 . A process according to claim 33 wherein the organosilicon condensate is chosen from a group comprising siloxane and polysiloxane.

36 . A process according to claim 33 wherein (A) and (B) are chosen from a group comprising monomeric, dimeric, oligomeric and polymeric compounds.

37 . A process according to claim 33 wherein (A) is a silanol is chosen from a group comprising compounds with from one to three unsubstituted or substituted hydrocarbon groups having from 1 to 18 carbon atoms.

38 . A process according to claim 37 wherein the silanol is selected from is chosen from a group comprising diphenyl silanediol, vinyl-diphenyl silanediol and dipentafluorophenyl silanediol.

39 . A process according to claim 33 wherein (A) comprises a crosslinkable group.

40 . A process according to claim 39 wherein the crosslinkable group is chosen from a group comprising an epoxide group, a double bond of the acrylate type, a double bond of the methacrylate type and a double bond of the styrene type.

41 . A process according to claim 33 wherein (B) is a monomeric compound with the general formula

G y Si(OR) 4-y

wherein y has a value of 0, 1, 2 or 3,

G is chosen from a group comprising a unsubstituted and a substituted hydrocarbon group having from 1 to 18 carbon atoms; and

R is chosen from a group comprising alkyl groups having from 1 to 8 carbon atoms and alkoxyalkyl groups having from 2 to 8 carbon atoms.

42 . A process according to claim 41 wherein (B) is an alkoxysilane, which has from one to four alkoxy groups inclusive.

43 . A process according to claim 41 wherein OR is chosen from a group comprising methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy and t-butoxy.

44 . A process according to claim 41 wherein R or G are chosen from a group comprising crosslinkable groups.

45 . A process according to claim 44 wherein the crosslinkable group is chosen from a group comprising an epoxide group, a double bond of the acrylate type, a double bond of the methacrylate type and a double bond of the styrene type.

46 . A process according to claim 41 wherein (B) is chosen from a group comprising propyltrimethoxysilane, hexyltrimethoxysilane, octyltrimethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, hexadecyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, phenylethyltrimethoxysilane, phenylpropyltrimethoxysilane, 3,3,3-trifluoro-propyltrimethoxysilane, nonafluoro-1,1,2,2-tetrahydrohexyl-trimethoxysilane, tridecafluoro-1,1,2,2-tetrahydrooctyl-trimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-styrylpropyltrimethoxysilane and 3-glycidoxypropyltrimethoxysilane.

47 . A process according to claim 33 wherein (B) is an oligomeric or polymeric compound of general formula

R 1 3 SiO(SiR 1 2 O) n SiR 1 2 OR

wherein R is chosen from a group comprising an alkyl group having from 1 to 8 carbon atoms and an alkoxyalkyl group having from 2 to 8 carbon atoms, n is an integer ≧0, and each R 1 is chosen optionally from a group comprising an unsubstituted or substituted hydrocarbon group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 8 carbon atoms, and an alkoxyalkyl group having from 2 to 8 carbon atoms.

48 . A process according to claim 33 wherein (A) and (B) are each hydroxy-terminated siloxanes of general formula HO—(SiR 1 R 2 O) n —H

wherein R 1 and R 2 represent unsubstituted or substituted hydrocarbon groups having from 1 to 18 carbon atoms and may be the same or different and n is an integer >0.

49 . A process according to claim 33 wherein the catalyst is employed in an amount of from 0.0005 to 5% by mole ratio based on the total silicon containing compounds.

50 . A process according to claim 33 further comprising separation of the catalyst from the organosilicon condensate.

51 . A process according to claim 33 wherein the organosilicon condensate has a viscosity in the range from 1,000 to 4,000 cP.

52 . A process for the preparation of an organosilicon condensate comprising condensing at least one silicon containing compound having:

at least one silanol group (a);

and

at least one —OX group (b),

wherein X is chosen from a group comprising hydrogen, an alkyl group having from 1 to 8 carbon atoms, and an alkoxyalkyl group having from 2 to 8 carbon atoms in the presence of catalyst (c) chosen from a group comprising strontium oxide, barium oxide, strontium hydroxide, barium hydroxide and mixtures thereof.

53 . A process according to claim 52 wherein the catalyst is chosen from a group comprising strontium oxide and barium oxide.

54 . A process according to claim 52 wherein the catalyst is employed in an amount from 0.0005 to 5% by mole ratio based on the total silicon containing compounds.

55 . A process according to claim 52 further comprising separation of the catalyst from the organosilicon condensate.

56 . A process according to claim 52 wherein the organosilicon condensate has a viscosity in the range from 1,000 to 4,000 cP.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2013
From: RPO PTY LTD
To: TRINITY CAPITAL INVESTMENT LLC
Reel/Frame 029770/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2013
From: TRINITY CAPITAL INVESTMENT LLC
To: ZETTA RESEARCH AND DEVELOPMENT LLC - RPO SERIES
Reel/Frame 029770/0778 →
REASSIGNMENT AND RELEASE OF IP SECURITY INTEREST Recorded Aug 2, 2012
From: BRIDGE BANK, NATIONAL ASSOCIATION
To: RPO PTY LTD
Reel/Frame 028737/0963 →
SECURITY AGREEMENT Recorded Aug 17, 2010
From: RPO PTY LTD
To: BRIDGE BANK, NATIONAL ASSOCIATION
Reel/Frame 024838/0948 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2006
From: SCHAMSCHURIN, ANDREW; ATKINS, GRAHAM ROY; KUKULJ, DAX
To: RPO PTY LIMITED
Reel/Frame 018610/0139 →