US4093641A
Expired / Lapsed
US
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Preparation of silylalkyl esters of phosphorus
Assignee: Dow Silicones Corp
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Filing: 1977-09-26
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Granted: 1978-06-06
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Expires: 1997-09-26
Abstract
Abstract What is disclosed is a novel method of preparing silylalkyl esters of phosphorus using amines or phosphines, which are capable of forming onium compounds with the reactants, as catalysts. They are useful as flame retardant additives and lubricants on metals and textiles.
Inventors
- 👤 Edwin P. Plueddemann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 15:04
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C08; C08G; C08G79/00; C08G79/02; C08G79/04
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
194 words
A method of preparing silylalkyl esters of phosphorus which consists of (I) contacting and reacting silanes of the general formula (i) R 3 SiR'X or siloxanes of the general formula (ii) Me 3 SiO(Me 2 SiO) n (XR'MeSiO) m SiMe 3 or (iii) oligomers of the general formula (XR'Me.sub.2 Si).sub.2 O(Me.sub.2 SiO).sub.n with phosphorus compounds having the general formula ##STR37## at a temperature in the range of 100° C. to 300° C. in the presence of amines or phosphines capable of forming onium compounds with the reactants, for a period of time sufficient to remove all by-produced organic halide, and then (II) subjecting the resulting reaction mixture to a reduced pressure and an elevated temperature to remove undesired low boiling materials and (III) thereafter recovering the silylalkyl ester of phosphorus, wherein R is an alkyl group, aryl group, alkoxy group containing 1-4 carbon atoms, an R'X group or a siloxy group; X is chlorine, bromine or iodine; m is a positive integer; n is 0 or a positive integer; Me is methyl; R' is a divalent alkyl or aralkyl radical; R" is methyl, ethyl, phenyl, halobenzyl or --OR"' wherein R"' is methyl or phenyl.
Claim 2
Independent Claim
194 words
A method of preparing silylalkyl esters of phosphorus which consists of (I) contacting and reacting silanes of the general formula (i) R 3 SiR'X or siloxanes of the general formula (ii) Me 3 SiO(Me 2 SiO) n (XR'MeSiO) m SiMe 3 or (iii) oligomers of the general formula (XR'Me.sub.2 Si).sub.2 O(Me.sub.2 SiO).sub.n with phosphorus compounds having the general formula ##STR37## at a temperature in the range of 100° C. to 300° C. in the presence of amines or phosphines capable of forming onium compounds with the reactants, for a period of time sufficient to remove all by-produced organic halide, and then (II) subjecting the resulting reaction mixture to a reduced pressure and an elevated temperature to remove undesired low boiling materials and (III) thereafter recovering the silylalkyl ester of phosphorus, wherein R is an alkyl group, aryl group, alkoxy group containing 1-4 carbon atoms, an R'X group or a siloxy group; X is chlorine, bromine or iodine; m is a positive integer; n is 0 or a positive integer; Me is methyl; R' is a divalent alkyl or aralkyl radical; R" is methyl, ethyl, phenyl, halobenzyl or --OR"' wherein R"' is methyl or phenyl.
Claim 3
Dependent Claim
29 words
The method of claim 1 wherein an amine is present during the reaction, R 3 is (CH 3 O) 3 , X is chlorine, R' is an alkylene group.
Claim 4
Dependent Claim
30 words
The method of claim 1 wherein a phosphine is present during the reaction, R 3 is (CH 3 O) 3 , X is chlorine and R' is an alkylene group.
Claim 5
Dependent Claim
30 words
The method of claim 1 wherein an amine is present during the reaction, R 3 is (CH 3 O) 3 , X is bromine and R' is an alkylene group.
Claim 6
Dependent Claim
22 words
The method of claim 1 wherein the phosphorus compound has the formula ##STR38## and at least one R' is CH 3 O.
Claim 7
Dependent Claim
17 words
The method of claim 1 wherein the phosphorus compound has the formula ##STR39## and R" is phenoxy.
Claim 8
Dependent Claim
35 words
The method of claim 2 wherein the amine present during the reaction is benzyldimethylamine, R 3 is (CH 3 O) 3 , X is chlorine and R' is --CH 2 CH 2 CH 2 --.
Claim 9
Dependent Claim
47 words
The method of claim 2 wherein the amine present during the reaction is (CH 3 O) 3 SiCH 2 CH 2 CH 2 NHCH 3 , R 3 is (CH 3 O) 3 , X is chlorine and R' is --CH 2 CH 2 CH 2 --.
Claim 10
Dependent Claim
35 words
The method of claim 3 wherein the phosphine present during the reaction is tributylphosphine, R 3 is (CH 3 O) 3 , X is chlorine and R' is --CH 2 CH 2 CH 2 --.
Claim 11
Dependent Claim
29 words
The method of claim 4 wherein the amine present during the reaction is benzyldimethylamine, R 3 is (CH 3 O) 3 , X is bromine and R' is ##STR40##
Claim 12
Dependent Claim
12 words
The method of claim 5 wherein both R" are CH 3 O.
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) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |