WO2001074825A1 - Low-sulfur polysulfide silanes and process for preparation - Google Patents
Low-sulfur polysulfide silanes and process for preparation Download PDFInfo
- Publication number
- WO2001074825A1 WO2001074825A1 PCT/US2000/033181 US0033181W WO0174825A1 WO 2001074825 A1 WO2001074825 A1 WO 2001074825A1 US 0033181 W US0033181 W US 0033181W WO 0174825 A1 WO0174825 A1 WO 0174825A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silane
- sulfur
- group
- oligosulfide
- occurrence
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Definitions
- the invention relates to a method of preparing polysulfide-functional silanes
- Sulfur-containing silane coupling agents are particularly useful in providing
- Patents US 3,842,111 ; US 3,873,489; US 3,946,059; US 3,978,103; US 3,997,581 ;
- oligosulfide species is obtained, in which the number of sulfur atoms present in each
- sulfur ranks in which this term is taken to mean the number of sulfur
- the total amount of sulfur can be
- compositions by the methods known from the aforementioned prior art, in which the
- a second disadvantage is that to average a sulfur
- oxidizers based on oxygen such as manganese dioxide, chromates.
- this document describes the desulfurization of a mixture of oligosulfide silanes
- Cyanides can be toxic. Sulfites do not dissolve readily in the preferred
- Trivalent phosphorus compounds are expensive and
- silanes As in the two-step process starting from mercaptosilanes described in DE-PS
- polysulfide-functional silanes composed of novel sulfur rank distributions, i.e..
- the invention is less than the starting silane or mixture thereof. In one aspect, the invention
- oligosulfide silane containing a chain of more than two sulfur atoms, or a mixture thereof, comprising: reacting an oligosulfide silane with a mercaptosilane salt to obtain an oligosulfide
- polvsulfidic sulfur is
- method of the present invention can remove sulfur from oligosulfide silane
- silane components (monosulfides) remain inert to the desulfurization process.
- extraneous chemical groups or atoms such as cyanide, phosphorus, sulfite,
- thiosulfate. or thiocyanate are introduced or formed to require steps for removal, to
- the polysulfide-functional silanes of the present invention are
- the present invention describes the preparation of oligosulfide silane
- silane compositions comprising: oligosulfide silane "* shall refer to any single
- each occurrence of G is independently a divalent alkyl, alkenyl, aryl
- each R is independently alkyl, alkenyl, aryl or aralkyl wherein R can contain from 1 to
- each n is an
- n 3 to 8 (and in the course of the process n would be reduced
- alkyl includes straight, branched and cyclic alkyl groups
- alkenyl includes straight, branched and cyclic alkenyl groups containing one or
- alkyls include methyl, ethyl, propyl.
- isobutyl and specific aralkyls include phenyl, tolyl and phenethyl. As used herein,
- cyclic alkyl or “cyclic alkenyl” also includes bicyclic and higher cyclic structures
- examples include norbornyl. norbornenyl. ethylnorbornyl, ethylnorbornenyl.
- starting oligosulfide silanes include
- methoxy, or alkyl where ethoxy, methoxy, and methyl are particularly preferred, and ethoxy is most preferred: and in which G is -CH 2 -, -CH 2 CH 2 -, -CFLCFLCFL-, or
- -CH 2 CH 2 -. and -CH 2 CH 2 CH 2 - are particularly preferred, and -CH 2 CH 2 CH 2 - is most
- Formula (1 ) are bis-(3-triethoxysilyl-l -propyl) oligosulfides with varying n.
- salt is used to refer to an anion cation pair wherein the anion is the
- Such salts may be represented by the formula (2) X'X 2 X 3 SiG' - S " Z +
- silanes may be formed.
- the mercaptosilane starting material i.e., X i X 2 X , SiG'-SH
- X i X 2 X , SiG'-SH mercaptosilane starting material
- polysulfide silanes to yield the pure salt.
- the salts may be placed in solvents that are
- Suitable bases to form the salt of the mercaptosilane must be strong enough to
- alkali metals also could be used to deprotonate the mercaptosilane, and would release
- the preferred bases are sodium or potassium alkoxide or
- alkoxy group would be preferred if a single kind of alkoxy group is desired in the
- Preferred counterions (cations) ⁇ TL) are those whose sulfides and
- polysulfides are slightly soluble (preferably ⁇ 0.1 weight percent), most preferably
- the oligosulfide silane composition is desulfurized by reaction with the
- polysulfidic sulfur is sulfur chemically bound only to sulfur
- sulfide and/or polysulfide salt e.g., sodium sulfide
- the reaction preferably is run in a solvent, though it is not necessary if the
- polyethers glyme, diglyme and higher glymes.
- aromatic solvents such as toluene and
- the reaction temperature is not critical, but may be run at ambient temperature
- the pressure under which the reaction is run is not critical.
- the reaction may be run
- the products prepared according to the present invention can be used in any order.
- PHR parts per hundred parts rubber
- silica employed, preferably the ratio by weight of silica to silane being in
- Suitable rubber compositions are sulfur- vulcanizable synthetic rubber compositions.
- suitable rubber polymers include silicone rubber, rubber, rubber compositions.
- suitable rubber polymers include silicone rubber, rubber, rubber compositions.
- suitable rubber polymers include silicone rubber, silicone rubber, and silicone rubber compositions.
- SSBR solution styrene-butadiene rubber
- SBR styrene-butadiene rubber
- NR rubber
- BR polybutadiene
- EP ethylene-propylene co- and ter- polymers
- EPDM acrylonitrile-butadiene rubber
- NBR acrylonitrile-butadiene rubber
- preferabh' is comprised of at least one diene -based elastomer, or rubber.
- conjugated dienes are isoprene and 1,3-butadiene and suitable vinyl aromatic
- the rubber is a sulfur curable
- Such diene based elastomer, or rubber may be selected, for example, from at
- E-SBR emulsion polymerization derived styrene/butadiene
- the rubber compositions in addition to at least one elastomer of synthetic or
- the silica can be of the types known, for
- silica will be employed at a
- Precipitated silicas are preferred fillers.
- the silica may be characterized by
- the silica as well, having a BET surface area, as measured using nitrogen gas, preferably in the range of 40 to 600, and more usually in a range of 50 to 300 nr/g. Further, the silica, as well, the silica, as well, the silica, as well, the silica, as well
- alumina and aluminosilicate may be expected to have a CTAB
- the rubber composition may be compounded by methods known in the rubber
- additive materials such as, for example, curing aids,
- processing additives such as oils
- resins including tackifying resins, silicas, plasticizers. fillers, pigments, fatty acid.
- a rubber composition may prepared by a process such as by:
- thermomechanically mixing in at least one preparatory mixing step, to a
- conjugated diene and aromatic vinyl compound (ii) 5 to 100, preferably 25 to 80, phr
- particulate filler preferably contains 1 to 85 weight percent carbon black (iii) 0.05 to 20 parts by weight filler of at least one
- the rubber compositions of the invention may be employed, for example, to
- shoe soles or tire parts such as treads and sidewalls in the normal fashion as
- MS, and NMR respectively represent gram, milliliter, millimeter, molar
- the reactor consisted of a 5-liter flask fitted for reflux. Heat was supplied to
- thioether is suppressed by initially preparing an oligosulfide silane mixture rich in sulfur and thereby containing S3.
- S4 i.e. trisulfide.
- the reactor consisted of a 5-liter flask fitted to a 25-plate Oldershaw distilling
- step 1 was prepared (step 1) from 3-chloro-l-propyltriethoxysilane, anhydrous sodium sulfide, and sulfur in ethanol following methods well known in the art.
- step 2 was used as the starting silane to be partially desulfurized in the next step (step 2) of
- starting 3-mercapto-l-propyltriethoxysilane also contained methoxy contamination as
- the reactor was set up as in Example 3.
- the reactor was as in Example 3.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00982501A EP1268491B1 (en) | 2000-01-04 | 2000-12-06 | Low-sulfur polysulfide silanes and process for preparation |
DE60018483T DE60018483T2 (en) | 2000-01-04 | 2000-12-06 | POLYSULFIDE SILANE WITH A LOW SULFUR CONTENT AND A METHOD OF MANUFACTURING THEREOF |
AT00982501T ATE290008T1 (en) | 2000-01-04 | 2000-12-06 | LOW SULFUR POLYSULFIDE SILANES AND A METHOD FOR THE PRODUCTION THEREOF |
JP2001572515A JP2003534247A (en) | 2000-01-04 | 2000-12-06 | Low sulfur polysulfide silane and method for producing the same |
BR0016894-7A BR0016894A (en) | 2000-01-04 | 2000-12-06 | Low sulfur polysulfide silanes and process for preparation |
KR1020027008964A KR20020093791A (en) | 2000-01-04 | 2000-12-06 | Low-sulfur polysulfide silanes and process for preparation |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/477,394 US6452034B2 (en) | 2000-01-04 | 2000-01-04 | Low-sulfur polysulfide silanes and process for preparation |
US09/477,394 | 2000-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001074825A1 true WO2001074825A1 (en) | 2001-10-11 |
Family
ID=23895742
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/033181 WO2001074825A1 (en) | 2000-01-04 | 2000-12-06 | Low-sulfur polysulfide silanes and process for preparation |
Country Status (9)
Country | Link |
---|---|
US (1) | US6452034B2 (en) |
EP (2) | EP1439183B1 (en) |
JP (1) | JP2003534247A (en) |
KR (1) | KR20020093791A (en) |
CN (1) | CN1231486C (en) |
AT (2) | ATE290008T1 (en) |
BR (1) | BR0016894A (en) |
DE (2) | DE60037044T2 (en) |
WO (1) | WO2001074825A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1342750A1 (en) * | 2002-03-08 | 2003-09-10 | Shin-Etsu Chemical Co., Ltd. | Preparation of sulfide chain-bearing organosilicon compounds |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2823210B1 (en) * | 2001-04-10 | 2005-04-01 | Rhodia Chimie Sa | ORGANOXYSILANES POLYSULFIDES USED IN PARTICULAR AS A COUPLING AGENT, ELASTOMERIC COMPOSITIONS (S) CONTAINING SAME AND ARTICLES ELASTOMER (S) PREPARED FROM SUCH COMPOSITIONS |
JP3975323B2 (en) * | 2001-07-25 | 2007-09-12 | 信越化学工業株式会社 | Method for producing sulfide chain-containing organosilicon compound |
MY164448A (en) * | 2003-12-15 | 2017-12-15 | Ciba Holding Inc | Coupling agents between filler and elastomer |
EP1948668A1 (en) * | 2005-11-16 | 2008-07-30 | Dow Corning Corporation | Organosilanes and their preparation and use in elastomer compositions |
US8551339B2 (en) * | 2009-03-06 | 2013-10-08 | Heritage Environmental Services Llc | Use of silica for the removal of organosilanes |
JP5942868B2 (en) * | 2013-01-23 | 2016-06-29 | 信越化学工業株式会社 | Method for producing sulfide group-containing organosilicon compound |
DE102014209215A1 (en) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Process for the preparation of urea-containing silanes |
DE102014209239A1 (en) * | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Urea-containing silanes, process for their preparation and their use |
DE102014209226A1 (en) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Urea-containing silanes, process for their preparation and their use |
DE102014209233A1 (en) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Urea-containing mercaptosilanes, process for their preparation and their use |
DE102014209221A1 (en) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Process for the preparation of urea-containing mercaptosilanes |
CN104592315B (en) * | 2014-12-29 | 2017-09-15 | 北京彤程创展科技有限公司 | A kind of thio metallic compound nano material of siloxy and preparation method thereof |
DE102017221277A1 (en) * | 2017-11-28 | 2019-05-29 | Evonik Degussa Gmbh | Silane mixtures and process for their preparation |
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DE2405758A1 (en) * | 1974-02-07 | 1975-08-21 | Degussa | PROCESS FOR PRODUCING ORGANOSILICIUM COMPOUNDS CONTAINING SULFUR |
JPS575724A (en) * | 1980-06-13 | 1982-01-12 | Fujikura Ltd | Crosslinkable halogen-containing polymer composition and method of crosslinking the same |
EP0845472A2 (en) * | 1996-11-29 | 1998-06-03 | Shin-Etsu Chemical Co., Ltd. | Desulfurization of polysulfide silanes |
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DE2712866C3 (en) | 1977-03-24 | 1980-04-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Process for the preparation of organosilicon compounds containing sulfur |
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2000
- 2000-01-04 US US09/477,394 patent/US6452034B2/en not_active Expired - Lifetime
- 2000-12-06 BR BR0016894-7A patent/BR0016894A/en not_active Application Discontinuation
- 2000-12-06 DE DE60037044T patent/DE60037044T2/en not_active Expired - Lifetime
- 2000-12-06 JP JP2001572515A patent/JP2003534247A/en not_active Abandoned
- 2000-12-06 KR KR1020027008964A patent/KR20020093791A/en not_active Application Discontinuation
- 2000-12-06 CN CNB008185344A patent/CN1231486C/en not_active Expired - Fee Related
- 2000-12-06 DE DE60018483T patent/DE60018483T2/en not_active Expired - Lifetime
- 2000-12-06 AT AT00982501T patent/ATE290008T1/en not_active IP Right Cessation
- 2000-12-06 AT AT04004550T patent/ATE377604T1/en not_active IP Right Cessation
- 2000-12-06 WO PCT/US2000/033181 patent/WO2001074825A1/en active IP Right Grant
- 2000-12-06 EP EP04004550A patent/EP1439183B1/en not_active Expired - Lifetime
- 2000-12-06 EP EP00982501A patent/EP1268491B1/en not_active Expired - Lifetime
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1342750A1 (en) * | 2002-03-08 | 2003-09-10 | Shin-Etsu Chemical Co., Ltd. | Preparation of sulfide chain-bearing organosilicon compounds |
US7041843B2 (en) | 2002-03-08 | 2006-05-09 | Shin-Etsu Chemical Co., Ltd. | Preparation of sulfide chain-bearing organosilicon compounds |
Also Published As
Publication number | Publication date |
---|---|
CN1425020A (en) | 2003-06-18 |
ATE290008T1 (en) | 2005-03-15 |
DE60037044T2 (en) | 2008-08-28 |
DE60018483D1 (en) | 2005-04-07 |
BR0016894A (en) | 2002-12-10 |
KR20020093791A (en) | 2002-12-16 |
CN1231486C (en) | 2005-12-14 |
DE60037044D1 (en) | 2007-12-20 |
JP2003534247A (en) | 2003-11-18 |
EP1268491B1 (en) | 2005-03-02 |
EP1439183B1 (en) | 2007-11-07 |
US6452034B2 (en) | 2002-09-17 |
EP1268491A1 (en) | 2003-01-02 |
US20010051739A1 (en) | 2001-12-13 |
EP1439183A1 (en) | 2004-07-21 |
ATE377604T1 (en) | 2007-11-15 |
DE60018483T2 (en) | 2006-01-12 |
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