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US4011247A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for the preparation of an organohydrogenpolysiloxane as a product of a partial addition reaction

Assignee: Shin-Etsu Chemical Co Ltd
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Filing: 1974-10-04
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Granted: 1977-03-08
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Expires: 1994-10-04
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Abstract

Abstract Starting from an organohydrogenpolysiloxane having at least two hydrogen atoms directly bonded to the silicone atoms, an organohydrogenpolysiloxane is obtained in which part of the silicon-bonded hydrogen atoms have been converted into organic groups and the remaining silicon-bonded hydrogen atoms are left unreacted. The starting organohydrogenpolysiloxane is brought to the partial addition reaction with less than equivalent amount of an organic unsaturated compound having aliphatic double bond in the molecule in the presence of a platinum catalyst, and the reaction mixture is subjected to distillation while the platinum catalyst is deactivated by added benzothiazole or derivatives thereof, thus providing for the production of the organohydrogenpolysiloxane of the invention in reproducibly in high yield. The compounds are useful as crosslinking agents in the manufacture of various silicone products.

Inventors

  • 👤 Yasuhiko Sato
  • 👤 Hiroshi Inomata
  • 👤 Toshio Shiobara

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 07:52
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0896; C08; C08G; C08G77/00; C08G77/04; C08G77/045

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 245 words
A method for the preparation of an organohydrogenpolysiloxane comprising the steps of: A. partial addition reaction between a. a cyclic or non-cyclic organic unsaturated compound with an aliphatic double bond in the molecule selected from the group consisting of ethylene, propylene, cyclohexene, styrene, α-methylstyrene, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, allyl acetate, allyl acrylate, allyl methacrylate, allyl glycidyl ether, vinyl cyclohexene monoepoxide and 4-vinyl styreneoxide, and b. starting organohydrogenpolysiloxane represented by the average formula (R) a (H) b SiO.sub.( 4-a-b)/2 where R is methyl or phenyl, a and b are each positive numbers expressed as 1 ≦ a ≦ 2 and b ≦ 1, respectively, with the proviso that 2 ≦ (a + b) ≦ 3, and having at least two hydrogen atoms directly bonded to the silicon atoms through Si--H linkages in one molecule, in an amount such that the amount of said hydrogen atoms in said starting organohydrogenpolysiloxane is in excess over equimolar to said aliphatic double bond, in the presence of a platinum catalyst, by which part of said Si--H linkages are subjected to addition reaction with said aliphatic double bonds and the remaining of said Si--H linkages are left unreacted, B. addition of a compound selected from the group consisting of benzothiazole, 2,2'-dithiobisbenzothiazole, 2-(morpholinothio)benzothiazole, and 2-(morpholinodithio) benzothiazole to the reaction mixture obtained by said partial addition reaction in an amount larger than equimolar to said platinum catalyst, and C. recovery of an organohydrogenpolysiloxane as the finished product by distillation.
Claim 2
Independent Claim 245 words
A method for the preparation of an organohydrogenpolysiloxane comprising the steps of: A. partial addition reaction between a. a cyclic or non-cyclic organic unsaturated compound with an aliphatic double bond in the molecule selected from the group consisting of ethylene, propylene, cyclohexene, styrene, α-methylstyrene, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, allyl acetate, allyl acrylate, allyl methacrylate, allyl glycidyl ether, vinyl cyclohexene monoepoxide and 4-vinyl styreneoxide, and b. starting organohydrogenpolysiloxane represented by the average formula (R) a (H) b SiO.sub.( 4-a-b)/2 where R is methyl or phenyl, a and b are each positive numbers expressed as 1 ≦ a ≦ 2 and b ≦ 1, respectively, with the proviso that 2 ≦ (a + b) ≦ 3, and having at least two hydrogen atoms directly bonded to the silicon atoms through Si--H linkages in one molecule, in an amount such that the amount of said hydrogen atoms in said starting organohydrogenpolysiloxane is in excess over equimolar to said aliphatic double bond, in the presence of a platinum catalyst, by which part of said Si--H linkages are subjected to addition reaction with said aliphatic double bonds and the remaining of said Si--H linkages are left unreacted, B. addition of a compound selected from the group consisting of benzothiazole, 2,2'-dithiobisbenzothiazole, 2-(morpholinothio)benzothiazole, and 2-(morpholinodithio) benzothiazole to the reaction mixture obtained by said partial addition reaction in an amount larger than equimolar to said platinum catalyst, and C. recovery of an organohydrogenpolysiloxane as the finished product by distillation.
Claim 3
Dependent Claim 34 words
The method for the preparation of an organohydrogenpolysiloxane as claimed in claim 1 wherein said starting organohydrogenpolysiloxane is a cyclic methylhydrogenpolysiloxane with the number of silicon atoms from 3 to 6 in one molecule.
Claim 4
Dependent Claim 28 words
The method for the preparation of an organohydrogenpolysiloxane as claimed in claim 1 wherein said starting organohydrogenpolysiloxane is a linear polydimethylsiloxane terminated at both ends by dimethylhydrogensilyl groups.
Claim 5
Dependent Claim 19 words
The process of the preparation of an organohydrogenpolysiloxane as claimed in claim 1 wherein said starting organohydrogenpolysiloxane is 1,3,5,7-tetramethylcyclotetrasiloxane.
Claim 6
Dependent Claim 47 words
The method for the preparation of an organohydrogenpolysiloxane as claimed in claim 1 wherein said platinum catalyst is selected from the group consisting of chloroplatinic acid, adducts of chloroplatinic acid with alcohols, chloroplatinic acid-olefin complexes, platinum black and finely dispersed platinum supported on alumina or silica carriers.
Claim 7
Dependent Claim 45 words
The method for the preparation of an organohydrogenpolysiloxane as claimed in claim 1 wherein said platinum catalyst is employed in an amount ranging from 10 - 7 mole to 10 - 3 mole per mole of said aliphatic double bonds in said organic unsaturated compound.

References Cited (Backward Citations)

US2970150A Cited
US3666813A Cited
US3663181A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-07 1980-09-06 1981-03-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-07 1984-09-06 1985-03-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-07 1988-09-06 1989-03-08 $7700.00 Window Closed / Lapsed

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