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US4384132A
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Bis-(silylethyl)-oligosulphides and process for their production
Assignee: Evonik Operations GmbH
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Filing: 1981-07-13
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Granted: 1983-05-17
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Expires: 2001-07-13
Abstract
Abstract Novel bis-(silylethyl)-oligosulphides are obtained by reacting a vinyl silane of the formula (CH 2 ═CH) m -- SiR n 1 R 4 -(m+n) in which R represents chlorine, bromine, iodine, C 1 -C 3 -alkoxy, 2-methoxyethoxy, 2-ethoxyethoxy or hydroxy, R 1 represents C 1 -C 3 -alkyl, phenyl or C 5 -C 7 -cycloalkyl, n is 0, 1 or 2, m is 1 or 2 and m+n is 1, 2 or 3 with sulphur as well as in a given case hydrogen sulphide in molar ratios of vinyl silane to sulphur of from 1:2.5 to 1:10 and vinyl silane to hydrogen sulphide of from 1:0 to 1:5 at temperatures between about 100° and 200° C. under pressure of from 1 to 25 bars (total pressure at the reaction temperature) and in the presence of sulphidation catalysts known per se, in a given case followed by hydrolysis or partial hydrolysis of the reaction products. The bis-(silylethyl)-oligosulphides are used as reinforcing additives (adhesive agents) in crosslinkable rubber mixtures containing silicate fillers and in a given case carbon black as well as in a given case sulphur and other customary constituents.
Inventors
- 👤 Rudolf Schwarz
- 👤 Peter Kleinschmit
- 👤 Christa Liedtke
- 👤 Siegfried Wolff
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:24
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/54; C08K5/548; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/12; C07F7/18; C07F7/1804; C08G; C08G75/00; C08G75/02; C08G75/14
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
176 words
A bis-(silylethyl)-oligosulphide corresponding to the following average formula: {R.sub.4-(m+n) R.sub.n.sup.1 Si[CH.sub.2 CH.sub.2 ].sub.m }.sub.2 S.sub.mx I in which R represents chlorine, bromine, iodine, C 1 -C 3 -alkoxy, 2-methoxy ethoxy, 2-ethoxy ethoxy or hydroxy, R 1 represents C 1 -C 3 -alkyl, phenyl or C 5 -C 7 -cycloalkyl, n=0, 1 or 2, m=1 or 2, m+n=1, 2 or 3, and x=2.0 to 8.0, by reacting a vinyl silane corresponding to the following formula (CH.sub.2 ═CH).sub.m --SiR.sub.n.sup.1 R.sub.4 -(m+n) II in which R, R 1 , n and m are as defined above, with sulphur and, optionally, hydrogen sulphide in molar ratios of vinyl silane to sulphur of from 1:2.5 to 1:10 and vinyl silane to hydrogen sulphide of from 1:0 to 1:5 at a temperature in the range from about 100° to 210° C., under a pressure of from 1 to 25 bars (total pressure at the reaction temperature) and in the presence of a sulphidation catalyst or a bis-(silylethyl)-oligosulphide prepared by at least partially hydrolyzing the R group of the oligosulphide of formula I.
Claim 2
Dependent Claim
176 words
A bis-(silylethyl)-oligosulphide corresponding to the following average formula: {R.sub.4-(m+n) R.sub.n.sup.1 Si[CH.sub.2 CH.sub.2 ].sub.m }.sub.2 S.sub.mx I in which R represents chlorine, bromine, iodine, C 1 -C 3 -alkoxy, 2-methoxy ethoxy, 2-ethoxy ethoxy or hydroxy, R 1 represents C 1 -C 3 -alkyl, phenyl or C 5 -C 7 -cycloalkyl, n=0, 1 or 2, m=1 or 2, m+n=1, 2 or 3, and x=2.0 to 8.0, by reacting a vinyl silane corresponding to the following formula (CH.sub.2 ═CH).sub.m --SiR.sub.n.sup.1 R.sub.4 -(m+n) II in which R, R 1 , n and m are as defined above, with sulphur and, optionally, hydrogen sulphide in molar ratios of vinyl silane to sulphur of from 1:2.5 to 1:10 and vinyl silane to hydrogen sulphide of from 1:0 to 1:5 at a temperature in the range from about 100° to 210° C., under a pressure of from 1 to 25 bars (total pressure at the reaction temperature) and in the presence of a sulphidation catalyst or a bis-(silylethyl)-oligosulphide prepared by at least partially hydrolyzing the R group of the oligosulphide of formula I.
Claim 3
Dependent Claim
16 words
A compound according to claim 1 wherein the reaction is at about 100° to 200° C.
Claim 4
Dependent Claim
13 words
A compound according to claim 2 wherein x is between 6.9 and 8.0.
Claim 5
Dependent Claim
13 words
A compound according to claim 3 wherein x is between 7.0 and 8.0.
Claim 6
Dependent Claim
11 words
A compound according to claim 4 wherein x is about 7.5.
Claim 7
Dependent Claim
15 words
A compound according to claim 2 which is prepared in the absence of hydrogen sulphide.
Claim 8
Dependent Claim
30 words
A compound according to claim 2 which is prepared in the presence of hydrogen sulphide there being employed 0.1 to 5 moles of hydrogen sulphide per mole of vinyl silane.
Claim 9
Dependent Claim
11 words
A compound according to claim 2 wherein there is no hydrolysis.
Claim 10
Dependent Claim
23 words
A compound according to claim 2 wherein R is C 1 -C 3 -alkoxy or chlorine, n is 0 and m is 1.
Claim 11
Dependent Claim
14 words
A compound according to claim 9 wherein R is C 1 -C 3 alkoxy.
Claim 12
Dependent Claim
10 words
A compound according to claim 10 wherein R is ethoxy.
Claim 13
Dependent Claim
13 words
A compound according to claim 11 wherein x is between 6.9 and 8.0.
Claim 14
Dependent Claim
11 words
A compound according to claim 12 wherein x is about 7.6.
Claim 15
Dependent Claim
13 words
A compound according to claim 11 prepared in the absence of hydrogen sulphide.
Claim 16
Dependent Claim
28 words
A compound according to claim 11 prepared in the presence of hydrogen sulphide, there being employed 0.1 to 5 moles of hydrogen sulphide per mole of vinyl silane.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-05-16 | 1986-11-15 | 1987-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-16 | 1990-11-15 | 1991-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-16 | 1994-11-15 | 1995-05-17 | $7700.00 | Window Closed / Lapsed |