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US4160775A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of novel organosilicon compounds

Assignee: OSI Specialties Inc
•
Filing: 1978-03-28
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Granted: 1979-07-10
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Expires: 1998-03-28
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Abstract

Abstract Organic compounds having the formula CH2=C(R DEG )CH3-mXm INCLUDING THOSE HAVING ALKALLYL GROUPS SUCH AS:

Inventors

  • 👤 Curtis L. Schilling, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 15:21
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10; C07F7/0834; C07F7/0838; C07F7/0872; C07F7/0876; C07F7/0878; C07F7/0879; C07F7/18; C07F7/1896; C08; C08G; C08G77/00; C08G77/04; C08G77/38

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 256 words
Process of making an organofunctional siloxane having bonded to silicon at least one monovalent group of the formula --CH.sub.2 CH(R°)CH.sub.3-m X.sub.m wherein R° is a monovalent hydrocarbon group, X is a hydrocarbonoxy group, a cyanohydrocarbonoxy group, an acyloxy group, a halogen atom, a hydroxy group, a cyano group or a group having the formula --OC(O)NR 2 wherein R is a monovalent nitrogen-free organic radical, a divalent hydrocarbon group when both R's are taken together or hydrogen and may be the same or different throughout the same group or molecule, when X is halogen, hydroxy, cyano or a group of the formula --OC(O)NR 2 , m is an integer of 1 and, when X is hydrocarbonoxy, cyanohydrocarbonoxy or acyloxy, m is 1 or 2, comprising subjecting a substituted allyl compound having the formula: CH.sub.2 ═ C(R°)CH.sub.3-m X.sub.m wherein X and m are as defined above and an organosiloxane having at least one silicon-bonded hydrogen to addition reaction conditions under which said silicon-bonded hydrogen and the silicon to which it is bonded become bonded respectively to the vicinal carbon atoms comprising the unsaturation of said substituted allyl compound, said organosiloxane and said substituted allyl compound having no groups that would interfere with said addition reaction and no groups, other than substituted allyl groups of said substituted allyl compound and silicon bonded hydrogen, that react under said addition reaction conditions, with the proviso that, when X is halogen, hydroxyl or cyano, the substituted allyl compound is added incrementally to said organosiloxane which is maintained at said addition reaction conditions.
Claim 2
Dependent Claim 256 words
Process of making an organofunctional siloxane having bonded to silicon at least one monovalent group of the formula --CH.sub.2 CH(R°)CH.sub.3-m X.sub.m wherein R° is a monovalent hydrocarbon group, X is a hydrocarbonoxy group, a cyanohydrocarbonoxy group, an acyloxy group, a halogen atom, a hydroxy group, a cyano group or a group having the formula --OC(O)NR 2 wherein R is a monovalent nitrogen-free organic radical, a divalent hydrocarbon group when both R's are taken together or hydrogen and may be the same or different throughout the same group or molecule, when X is halogen, hydroxy, cyano or a group of the formula --OC(O)NR 2 , m is an integer of 1 and, when X is hydrocarbonoxy, cyanohydrocarbonoxy or acyloxy, m is 1 or 2, comprising subjecting a substituted allyl compound having the formula: CH.sub.2 ═ C(R°)CH.sub.3-m X.sub.m wherein X and m are as defined above and an organosiloxane having at least one silicon-bonded hydrogen to addition reaction conditions under which said silicon-bonded hydrogen and the silicon to which it is bonded become bonded respectively to the vicinal carbon atoms comprising the unsaturation of said substituted allyl compound, said organosiloxane and said substituted allyl compound having no groups that would interfere with said addition reaction and no groups, other than substituted allyl groups of said substituted allyl compound and silicon bonded hydrogen, that react under said addition reaction conditions, with the proviso that, when X is halogen, hydroxyl or cyano, the substituted allyl compound is added incrementally to said organosiloxane which is maintained at said addition reaction conditions.
Claim 3
Dependent Claim 156 words
Process as claimed in claim 1 for making an organofunctional siloxane containing one or more unit of the formula: ##STR27## and having no other units or one or more unit of the formula: ##STR28## wherein X is as defined in claim 1, n is an integer of 1 to 18, R' is hydrogen or a monovalent hydrocarbon group which may be the same or different through the same unit or molecule, a is an integer of 1 to 3, b is an integer of 0 to 2, and c is an integer of 0 to 3, comprising reacting an alkallyl compound as defined in claim 1 wherein R° is --C n H 2n+1 - with a siloxane precursor having one or more unit of the formula: ##STR29## and having no other units or one or more unit of the formula: ##STR30## wherein R', a, b and c are as defined above to form said organofunctional siloxane.
Claim 4
Dependent Claim 17 words
Process as claimed in claim 2 wherein said alkallyl compound is added incrementally to said siloxane precursor.
Claim 5
Dependent Claim 33 words
Process as claimed in claim 2 wherein n is 1, a is 0 to 1, b is 1 to 2, a + b is 2 to 3, and c is 2 to 3.
Claim 6
Dependent Claim 31 words
Process as claimed in claim 2 wherein said alkallyl compound is a methallyl compound of the formula: CH.sub.2 ═ C(CH.sub.3)CH.sub.3-m X.sub.m wherein X and m are as defined in claim 1.
Claim 7
Dependent Claim 30 words
Process as claimed in claim 2 wherein X is chlorine, m is 1 and the alkallyl compound is methallyl chloride and said methallyl chloride is added incrementally to said organosiloxane.
Claim 8
Dependent Claim 11 words
Process as claimed in claim 6 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 9
Dependent Claim 11 words
Process as claimed in claim 6 wherein said organosiloxane is heptamethyltrisiloxane.
Claim 10
Dependent Claim 20 words
Process as claimed in claim 2 wherein X is acetyl, m is 1 and the alkallyl compound is methallyl acetate.
Claim 11
Dependent Claim 11 words
Process as claimed in claim 9 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 12
Dependent Claim 11 words
Process as claimed in claim 9 wherein said organosiloxane is heptamethyltrisiloxane.
Claim 13
Dependent Claim 20 words
Process as claimed in claim 2 wherein X is methacryloyl, m is 1 and the alkallyl compound is methallyl methacrylate.
Claim 14
Dependent Claim 11 words
Process as claimed in claim 12 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 15
Dependent Claim 20 words
Process as claimed in claim 2 wherein X is acetyl, m is 2 and the alkallyl compound is methallylidene diacetate.
Claim 16
Dependent Claim 11 words
Process as claimed in claim 14 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 17
Dependent Claim 11 words
Process as claimed in claim 14 wherein said organosiloxane is heptamethyltrisiloxane.
Claim 18
Dependent Claim 20 words
Process as claimed in claim 2 wherein X is carbamoyl, m is 1 and the alkallyl compound is methallyl carbamate.
Claim 19
Dependent Claim 11 words
Process as claimed in claim 17 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 20
Dependent Claim 11 words
Process as claimed in claim 17 wherein said organosiloxane is heptamethyltrisiloxane.
Claim 21
Dependent Claim 25 words
Process as claimed in claim 2 wherein X is methoxy, m is 1, the alkallyl compound is methallyl methyl ether and said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 22
Dependent Claim 23 words
Process as claimed in claim 2 wherein X is beta-cyanoethoxy, m is 1, the alkallyl compound is 3-methallyloxypropionitrile, and said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 23
Dependent Claim 24 words
Process as claimed in claim 2 wherein X is cyano, m is 1, the alkallyl compound is methallyl cyanide, and said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 24
Dependent Claim 20 words
Process as claimed in claim 2 wherein X is hydroxyl, m is 1, and the alkallyl compound is methallyl alcohol.
Claim 25
Dependent Claim 11 words
Process as claimed in claim 23 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 26
Dependent Claim 11 words
Process as claimed in claim 23 wherein said organosiloxane is heptamethyltrisiloxane.
Claim 27
Dependent Claim 11 words
Process as claimed in claim 2 wherein said organosiloxane is heptamethylcyclotetrasiloxane.
Claim 28
Dependent Claim 11 words
Process as claimed in claim 2 wherein said organosiloxane is heptamethyltrisiloxane.

References Cited (Backward Citations)

US2823218A Cited
US2970150A Cited
US3957843A Cited
US4059605A Cited
US3842112A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-07-09 1983-01-08 1983-07-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-07-09 1987-01-08 1987-07-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-07-09 1991-01-08 1991-07-10 $7700.00 Window Closed / Lapsed

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