GB1022743A - A process for polymerising organosilicon compounds - Google Patents

A process for polymerising organosilicon compounds

Info

Publication number
GB1022743A
GB1022743A GB12684/64A GB1268464A GB1022743A GB 1022743 A GB1022743 A GB 1022743A GB 12684/64 A GB12684/64 A GB 12684/64A GB 1268464 A GB1268464 A GB 1268464A GB 1022743 A GB1022743 A GB 1022743A
Authority
GB
United Kingdom
Prior art keywords
radicals
hydrocarbon
ch2sna
radical
aliphatic unsaturation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB12684/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US269151A external-priority patent/US3243410A/en
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Publication of GB1022743A publication Critical patent/GB1022743A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
    • C08G77/52—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • 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
    • C07F7/0834—Compounds having one or more O-Si linkage
    • 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
    • C07F7/0896—Compounds with a Si-H linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages

Abstract

In polymerizing organosilicon compounds' an organosilicon compound selected from (a) organosilicon compounds having an average per Si atom 1 to 3 monovalent hydrocarbon, halohydrocarbon or cyanoalkyl radicals, and at least one SiOH group per molecule, any remaining Si valencies being satisfied by divalent oxygen atoms or divalent hydrocarbon, hydrocarbon ether (containing not more than one oxygen atom therein) and/or haloarylene radicals, (b) diorganosiloxane cyclic trimers, in which the organic radicals are as for (a) above, (c) diorgano-silethylenesiloxane cyclic dimers, in which the organic radicals are as for (a) above, except that they must be free from aliphatic unsaturation, and (d) mixtures thereof, is contacted with a compound of the formula R(SM)x, wherein R is a substituted or unsubstituted hydrocarbon radical of valency x, M is an alkali metal atom or a tetraorganonitrogen or -phosphorus radical, the organic radicals being monovalent hydrocarbon radicals free from aliphatic unsaturation, and x is at least 1, until the desired degree of polymerization is obtained. The preferred catalysts are CH3(CH2)3SK, HO.CH2.CH2SNa, C6H5SLi, CH3.CH(NO2)CH2SNa and CF3CH2.SK. The reaction, which proceeds at room temperature and is accelerated by heating, can be effected in an organic solvent for the reactants and product, any by-produced water being removed by any suitable means. In a typical Example (2) a mixture of KS.CH2.CH2OH and a hydroxyl-terminated dimethylpolysiloxane was heated at 110 DEG C. with stirring and under reduced pressure for 2 hours to yield a siloxane gum.ALSO:A compound suitable as a siloxane polymerization catalyst and having the formula R(SM)x, wherein R is a substituted or unsubstituted hydrocarbon radical of valency x, many examples of which are given, M is an alkali metal atom or a tetraorgano-nitrogen or -phosphorus radical, the organic radicals being monovalent hydrocarbon radicals free from aliphatic unsaturation, and x is at least 1, can be made by reacting storchiometric quantities of R(SH)x and MOH (though volatile thiols may be used in excess), preferably in a solvent for the reactants, e.g. water, alcohol and water-alcohol mixtures. The preferred compounds specified are CH3(CH2)3SK, HOCH2CH2SNa, C6H5SLi, CH3CH(NO2)CH2SNa and CF3CH2SK. In Example (1) a mixture of HSCH2CH2OH, KOH and CH3OH was agitated in a reactor until complete solution was attained, then by-produced water, methanol and excess thiol were removed by heating under reduced pressure to yield a white solid of KSCH2CH2OH. In Example (6) the following salts were made by the process of Example (1): C18H37SCs, (CH2CH2SLi)2, CH3CH2C[CH2SN(CH3)4]3, CF3CH2SN(CH3)3C12H25, CH3CH=CHCH2SNa, C6H5CH2SRb, <FORM:1022743/C2/1> <FORM:1022743/C2/2> <FORM:1022743/C2/3> and <FORM:1022743/C2/4>
GB12684/64A 1961-09-05 1964-03-25 A process for polymerising organosilicon compounds Expired GB1022743A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13578361A 1961-09-05 1961-09-05
US269151A US3243410A (en) 1963-03-29 1963-03-29 Organosilicon polymerizing catalyst

Publications (1)

Publication Number Publication Date
GB1022743A true GB1022743A (en) 1966-03-16

Family

ID=26833660

Family Applications (2)

Application Number Title Priority Date Filing Date
GB966059D Expired GB966059A (en) 1961-09-05
GB12684/64A Expired GB1022743A (en) 1961-09-05 1964-03-25 A process for polymerising organosilicon compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB966059D Expired GB966059A (en) 1961-09-05

Country Status (2)

Country Link
DE (2) DE1495427A1 (en)
GB (2) GB1022743A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0465129A1 (en) * 1990-06-29 1992-01-08 Shin-Etsu Chemical Co., Ltd. Fluorine-containing organosilicon compound
JPH0459785A (en) * 1990-06-29 1992-02-26 Shin Etsu Chem Co Ltd Fluorine-containing organic silicon compound
JPH0466587A (en) * 1990-06-29 1992-03-02 Shin Etsu Chem Co Ltd Fluorine-containing organosilicon compound
CN113214416A (en) * 2021-04-20 2021-08-06 国家能源集团宁夏煤业有限责任公司 Combined external electron donor, olefin polymerization catalyst and application thereof, and polyolefin and preparation method thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2353589A1 (en) * 1976-05-31 1977-12-30 Rhone Poulenc Ind PROCESS FOR THE PREPARATION OF ORGANOPOLYSILOXANES
US4101513A (en) * 1977-02-02 1978-07-18 Minnesota Mining And Manufacturing Company Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0465129A1 (en) * 1990-06-29 1992-01-08 Shin-Etsu Chemical Co., Ltd. Fluorine-containing organosilicon compound
JPH0459785A (en) * 1990-06-29 1992-02-26 Shin Etsu Chem Co Ltd Fluorine-containing organic silicon compound
JPH0466587A (en) * 1990-06-29 1992-03-02 Shin Etsu Chem Co Ltd Fluorine-containing organosilicon compound
CN113214416A (en) * 2021-04-20 2021-08-06 国家能源集团宁夏煤业有限责任公司 Combined external electron donor, olefin polymerization catalyst and application thereof, and polyolefin and preparation method thereof
CN113214416B (en) * 2021-04-20 2022-07-26 国家能源集团宁夏煤业有限责任公司 Combined external electron donor, olefin polymerization catalyst and application thereof, and polyolefin and preparation method thereof

Also Published As

Publication number Publication date
GB966059A (en) 1900-01-01
DE1495427A1 (en) 1969-04-10
DE1300288B (en) 1969-07-31

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