US4444936A
Expired / Lapsed
US
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Bis-(silylethyl)-oligosulphides and process for their production
Assignee: Evonik Operations GmbH
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Filing: 1983-01-27
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Granted: 1984-04-24
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Expires: 2003-01-27
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
2026-10-25 15:38
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: 21
Claim 1
Independent Claim
197 words
In a rubber composition comprising a cross-linkable rubber, a siliceous filler and a bis-(silylethyl)-oligosulphide, the improvement comprising having present as the oligosulphide a bis-(silyethyl)-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 2.sup.S 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
197 words
In a rubber composition comprising a cross-linkable rubber, a siliceous filler and a bis-(silylethyl)-oligosulphide, the improvement comprising having present as the oligosulphide a bis-(silyethyl)-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 2.sup.S 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
14 words
A rubber composition according to claim 1 wherein x is between 6.9 and 8.0.
Claim 4
Dependent Claim
14 words
A rubber composition according to claim 2 wherein x is between 7.0 and 8.0.
Claim 5
Dependent Claim
12 words
A rubber composition according to claim 3 wherein x is about 7.5.
Claim 6
Dependent Claim
18 words
A rubber composition according to claim 1 wherein the oligosulphide is prepared in the absence of hydrogen sulphide.
Claim 7
Dependent Claim
33 words
A rubber composition according to claim 1 wherein the oligosulphide 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 8
Dependent Claim
16 words
A rubber composition according to claim 1 wherein there is no hydrolysis in making the oligosulphide.
Claim 9
Dependent Claim
23 words
A compound according to claim 1 wherein R is C 1 -C 3 -alkoxy or chlorine, n is 0 and m is 1.
Claim 10
Dependent Claim
14 words
A compound according to claim 8 wherein R is C 1 -C 3 alkoxy.
Claim 11
Dependent Claim
10 words
A compound according to claim 9 wherein R is ethoxy.
Claim 12
Dependent Claim
13 words
A compound according to claim 10 wherein x is between 6.9 and 8.0.
Claim 13
Dependent Claim
11 words
A compound according to claim 11 wherein x is about 7.6.
Claim 14
Dependent Claim
24 words
A rubber composition according to claim 1 wherein the rubber is natural rubber, polybutadiene, polyisoprene, butadiene-styrene copolymer, butadiene-acrylonitrile copolymer or ethylene-propylene non-conjugated polyene terpolymer.
Claim 15
Dependent Claim
20 words
A rubber composition according to claim 1 wherein the rubber is a sulphur curable rubber and the composition includes sulphur.
Claim 16
Dependent Claim
31 words
A rubber composition according to claim 1 wherein the rubber is a sulphur curable rubber and the composition is free from sulphur and the sole crosslinking agent present is said bis-(silylethyl)-oligosulphide.
Claim 17
Dependent Claim
16 words
A rubber composition according to claim 14 wherein the siliceous filler is silica or a silicate.
Claim 18
Dependent Claim
11 words
A crosslinked rubber produced by curing the composition of claim 1.
Claim 19
Dependent Claim
13 words
A rubber composition according to claim 1 wherein x is 6.9 to 8.0.
Claim 20
Dependent Claim
24 words
A rubber composition according to claim 1 wherein R is C 1 -C 3 -alkoxy or chlorine, n is 0 and m is 1.
Claim 21
Dependent Claim
24 words
A rubber composition according to claim 19 wherein R is C 1 -C 3 -alkoxy or chlorine, n is 0 and m is 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) | 1987-04-24 | 1987-10-24 | 1988-04-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-24 | 1991-10-24 | 1992-04-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-24 | 1995-10-24 | 1996-04-24 | $7700.00 | Window Closed / Lapsed |