US4046795A
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Process for preparing thiofunctional polysiloxane polymers
Assignee: Wacker Chemical Corp
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Filing: 1975-11-10
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Granted: 1977-09-06
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Expires: 1995-11-10
Abstract
Abstract The invention relates to a process for preparing thiofunctional polysiloxane polymers which comprises reacting a disiloxane and/or a hydroxy or hydrocarbonoxy containing silane or siloxane with a cyclic trisiloxane in the presence of an acid catalyst wherein at least one of the above organosilicon compounds contain a thiol group. These thiofunctional polysiloxane polymers are useful as metal protectants and as release agents, especially on metal substrates.
Inventors
- 👤 Eugene Ray Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 06:46
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/22; C08G77/28
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
330 words
A method for preparing thiofunctional polysiloxane polymers which comprises reacting in the presence of a catalyst having a pK value below 1.0 a cyclic trisiloxane with a silicon compound selected from the class consisting of silanes of the formula ##STR13## and siloxanes of the formula ##STR14## in which the cyclic trisiloxane or silicon compound contains at least one thiol group, R is selected from the group consisting of a monovalent hydrocarbon radical and a halogenated monovalent hydrocarbon radical, each having from 1 to 18 carbon atoms, M is selected from the class consisting of R'(SR"') y and ##STR15## R' is selected from the group consisting of substituted and unsubstituted divalent, trivalent and tetravalent hydrocarbon radicals free of aliphatic unsaturation having from 1 to 18 carbon atoms, hydrocarbon ether, hydrocarbon thioether, hydrocarbon ester and hydrocarbon thioester radicals in which R' is attached to a silicon atom via a silicon-carbon bond, R" is selected from the group consisting of hydrogen and a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R'" is selected from the group consisting of R" and a radical represented by the formula R""X, wherein X is a radical selected from the group consisting of ##STR16## and a cyanoalkyl radical, in which R"" is a divalent hydrocarbon radical free of a aliphatic unsaturation having from 1 to 18 carbon atoms, Y is a radical selected from the class consisting of R 3 SiO 1/2 , RC═O and ##STR17## where R and R" are the same as above, b is a number of from 0 to 3, c is a number of from 0 to 3 and the sum of b+c is a number up to 3, d is a number of from 0 to 2, e is a number of from 1 to 3, m and n are each equal to a number of from 0 to 999 and the sum of m+n is at least 1 and y is a number of from 1 to 3.
Claim 2
Independent Claim
330 words
A method for preparing thiofunctional polysiloxane polymers which comprises reacting in the presence of a catalyst having a pK value below 1.0 a cyclic trisiloxane with a silicon compound selected from the class consisting of silanes of the formula ##STR13## and siloxanes of the formula ##STR14## in which the cyclic trisiloxane or silicon compound contains at least one thiol group, R is selected from the group consisting of a monovalent hydrocarbon radical and a halogenated monovalent hydrocarbon radical, each having from 1 to 18 carbon atoms, M is selected from the class consisting of R'(SR"') y and ##STR15## R' is selected from the group consisting of substituted and unsubstituted divalent, trivalent and tetravalent hydrocarbon radicals free of aliphatic unsaturation having from 1 to 18 carbon atoms, hydrocarbon ether, hydrocarbon thioether, hydrocarbon ester and hydrocarbon thioester radicals in which R' is attached to a silicon atom via a silicon-carbon bond, R" is selected from the group consisting of hydrogen and a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R'" is selected from the group consisting of R" and a radical represented by the formula R""X, wherein X is a radical selected from the group consisting of ##STR16## and a cyanoalkyl radical, in which R"" is a divalent hydrocarbon radical free of a aliphatic unsaturation having from 1 to 18 carbon atoms, Y is a radical selected from the class consisting of R 3 SiO 1/2 , RC═O and ##STR17## where R and R" are the same as above, b is a number of from 0 to 3, c is a number of from 0 to 3 and the sum of b+c is a number up to 3, d is a number of from 0 to 2, e is a number of from 1 to 3, m and n are each equal to a number of from 0 to 999 and the sum of m+n is at least 1 and y is a number of from 1 to 3.
Claim 3
Dependent Claim
323 words
The method of claim 1 wherein a mixture containing a cyclic trisiloxane and an organodisiloxane is reacted with a silicon compound selected from the class consisting of silanes of the formula ##STR18## and siloxanes of the formula ##STR19## in which the cyclic trisiloxane, or disiloxane or silicon compound contains at least one thiol group, R is selected from the group consisting of a monovalent hydrocarbon radical and a halogenated monovalent hydrocarbon radical, each having from 1 to 18 carbon atoms, M is selected from the class consisting of R'(SR'") y and ##STR20## R' is selected from the group consisting of substituted and unsubstituted divalent, trivalent and tetravalent hydrocarbon radicals free of aliphatic unsaturation having from 1 to 18 carbon atoms, hydrocarbon ether, hydrocarbon thioether, hydrocarbon ester and hydrocarbon thioester radicals in which R' is attached to a silicon atom via a silicon-carbon bond, R" is selected from the group consisting of hydrogen and a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R'" is selected from the group consisting of R" and a radical represented by the formula R""X, wherein X is a radical selected from the group consisting of ##STR21## and a cyanoalkyl radical, in which R"" is a divalent hydrocarbon radical free of aliphatic unsaturation having from 1 to 18 carbon atoms, Y is a radical selected from the class consisting of R 3 SiO 1/2 , RC═O and ##STR22## where R and R" and the same as above, b is a number of from 0 to 3, c is a number of from 0 to 3 and the sum of b+c is a number up to 3, d is a number of from 0 to 2, e is a number of from 1 to 3, m and n are each equal to a number of from 0 to 999 and the sum of m+n is at least 1 and y is a number of from 1 to 3.
Claim 4
Dependent Claim
188 words
The method of claim 2 wherein the organodisiloxane is represented by the formula M.sub.a R.sub.(6-a) Si.sub.2 O wherein R is selected from the group consisting of a monovalent hydrocarbon radical and a halogenated hydrocarbon radical, each having from 1 to 18 carbon atoms, a is a number of from 0 to 6, M is selected from the class consisting of R'(SR'") y and ##STR23## wherein R' is selected from the group consisting of substituted and unsubstituted divalent, trivalent and tetravalent hydrocarbon radicals free of aliphatic unsaturation having from 1 to 18 carbon atoms, hydrocarbon ether, hydrocarbon thioether, hydrocarbon ester and hydrocarbon thioester radicals, in which R' is attached to a silicon atom via a silicon-carbon bond, R'" is selected from the group consisting of hydrogen, a monovalent hydrocarbon radical having from 1 to 18 carbon atoms and a radical represented by the formula R""X, wherein X is a radical selected from the group consisting of ##STR24## and a cyanoalkyl radical, in which R""is a divalent hydrocarbon radical free of aliphatic unsaturation having from 1 to 18 carbon atoms and y is a number of from 1 to 3.
Claim 5
Dependent Claim
190 words
The method of claim 1 wherein the cyclic trisiloxane is represented by the formula M.sub.a R.sub.6-a Si.sub.3 O.sub.3 wherein R is selected from the group consisting of a monovalent hydrocarbon radical and a halogenated hydrocarbon radical, each having from 1 to 18 carbon atoms, a is a number of from 0 to 6, M is selected from the class consisting of R'(SR'") y and ##STR25## wherein R' is selected from the group consisting of substituted and unsubstituted divalent, trivalent and tetravalent hydrocarbon radicals free of aliphatic unsaturation having from 1 to 18 carbon atoms, hydrocarbon ether, hydrocarbon thioether, hydrocarbon ester and hydrocarbon thioester radicals, in which R' is attached to a silicon atom via a silicon-carbon bond, R'" is selected from the group consisting of hydrogen, a monovalent hydrocarbon radical having from 1 to 18 carbon atoms and a radical represented by the formula R""X, wherein X is a radical selected from the group consisting of ##STR26## and a cyanoalkyl radical, in which R"" is a divalent hydrocarbon radical free of aliphatic unsaturation having from 1 to 18 carbon atoms and y is a number of from 1 to 3.
Claim 6
Dependent Claim
17 words
The method of claim 1 wherein the reaction is conducted in the presence of a hydrocarbon solvent.
Claim 7
Dependent Claim
10 words
The method of claim 4 wherein the solvent is toluene.
Claim 8
Dependent Claim
17 words
The method of claim 1 wherein the reaction is conducted at a temperature up to 200° C.
Claim 9
Dependent Claim
17 words
The method of claim 1 wherein the reaction is conducted in the presence of a protic compound.
Claim 10
Dependent Claim
11 words
The method of claim 8 wherein the protic compound is water.
Claim 11
Dependent Claim
12 words
The method of claim 8 wherein the protic compound is an alcohol.
Claim 12
Dependent Claim
10 words
The method of claim 2 wherein the organodisiloxane is hexamethyldisiloxane.
Claim 13
Dependent Claim
10 words
The method of claim 2 wherein the disiloxane is di(3-mercaptopropyl)tetramethyldisiloxane.
Claim 14
Dependent Claim
11 words
The method of claim 1 wherein the cyclic trisiloxane is hexamethylcyclotrisiloxane.
Claim 15
Dependent Claim
12 words
The method of claim 1 wherein the silicon compound is a mercaptoalkyltrihydrocarbonoxysilane.
Claim 16
Dependent Claim
12 words
The method of claim 14 wherein the silicon compound is a mercaptoalkyltrialkoxysilane.
Claim 17
Dependent Claim
11 words
The method of claim 14 wherein the silicon compound is beta-mercaptoethyltriethoxysilane.
Claim 18
Dependent Claim
12 words
The method of claim 14 wherein the silicon compound is a mercaptoalkyltrialkoxysilane.
Claim 19
Dependent Claim
13 words
The method of claim 1 wherein the silicon compound is a thioether alkyltrialkoxysilane.
Claim 20
Dependent Claim
19 words
The method of claim 1 wherein the silicon compound is obtained from the hydrolysis of a thiol containing silane.
Claim 21
Dependent Claim
16 words
The method of claim 19 wherein the silicon compound is obtained from the hydrolysis of 3-mercaptopropyltrimethoxysilane.
Claim 22
Dependent Claim
16 words
The method of claim 19 wherein the silicon compound is obtained from the hydrolysis of beta-mercaptoethyltriethoxysilane.
Claim 23
Dependent Claim
8 words
Thiofunctional polysiloxanes prepared in accordance with claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-05 | 1981-03-07 | 1981-09-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-05 | 1985-03-07 | 1985-09-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-05 | 1989-03-07 | 1989-09-06 | $7700.00 | Window Closed / Lapsed |