US4608270A
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Acylamino silicon compounds, their use and preparation
Assignee: Dow Silicones Corp
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Filing: 1985-10-25
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Granted: 1986-08-26
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Expires: 2005-10-25
Abstract
Abstract Organosilicon compounds containing at least one acylamino-substituted hydrocarbon radical are prepared by reacting an organosilicon compound containing at least one amino-substituted hydrocarbon radical with an acyl halide in the presence of an aqueous solution of an alkaline material and a solvent for the aminosilicon compound. The reaction is particularly useful for preparing polydiorganosiloxanes which contain one or more acrylylamino-substituted hydrocarbon radicals, which are polymerizable and are useful in coating compositions such as adhesive release coating compositions.
Inventors
- 👤 Padmakumari J. Varaprath
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:21
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C08G77/382; C08G77/388; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0838; C07F7/0872; C07F7/0889; C08L; C08L83/00; C08L83/04; C08L83/08; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
72 words
An organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical having the formula --QNAQ'NAZ, wherein Z denotes H or R, R denotes a monovalent hydrocarbon radical, Q and Q' denote divalent hydrocarbon radicals, A denotes an acyl radical having the formula ##STR50## and B denotes H or CH 3 , any remaining silicon-bonded radicals therein being selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms.
Claim 2
Dependent Claim
72 words
An organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical having the formula --QNAQ'NAZ, wherein Z denotes H or R, R denotes a monovalent hydrocarbon radical, Q and Q' denote divalent hydrocarbon radicals, A denotes an acyl radical having the formula ##STR50## and B denotes H or CH 3 , any remaining silicon-bonded radicals therein being selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms.
Claim 3
Dependent Claim
44 words
An organosilicon compound according to claim 1 having the average unit formula Rc(NHAQ'NAQ) d SiO.sub.(4-c-d)/2, wherein c has a value of from 0 to 3, d has a value of from >0 to 4, and c+d has a value of from 1 to 4.
Claim 4
Dependent Claim
50 words
An organosilicon compound according to claim 2 having the formula YR 2 SiO(R 2 SiO) x (YRSiO) y SIR 2 Y wherein Y denotes R or --QNACH 2 CH 2 NAH, x has a value of from 0 to 5000 and y has a value of from 0 to 500.
Claim 5
Dependent Claim
29 words
An organosilicon compound according to claim 2 having the formula (R) e Si(QNACH 2 CH 2 NAH) 4-e wherein e has a value of 0, 1, 2 or 3.
Claim 6
Dependent Claim
20 words
An organosilicon compound according to claim 2 wherein R is selected from the group consisting of methyl, phenyl and vinyl.
Claim 7
Independent Claim
161 words
A method for preparing an organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical, said method comprising (I) admixing (i) a composition comprising an acyl halide to (ii) a composition comprising an aminosilicon compound having at least one silicon-bonded amino-substituted hydrocarbon radical containing at least one nitrogen-bonded hydrogen, all other silicon valences therein being satisfied by radicals selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms, said admixing being done in the presence of (iii) an aqueous solution of a water- soluble alkaline material and (iv) a water-insoluble solvent for (ii), the amounts of components (i), (ii) and (iii) being sufficient to acylate at least one amino nitrogen atom containing at least one nitrogen-bonded hydrogen atom per molecule of aminosilicon compound and to provide at least an equivalent amount of alkaline material relative to the amount of acyl halide, and thereafter (II) agitating the mixture comprising (i) and (ii) until the compound is formed.
Claim 8
Independent Claim
161 words
A method for preparing an organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical, said method comprising (I) admixing (i) a composition comprising an acyl halide to (ii) a composition comprising an aminosilicon compound having at least one silicon-bonded amino-substituted hydrocarbon radical containing at least one nitrogen-bonded hydrogen, all other silicon valences therein being satisfied by radicals selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms, said admixing being done in the presence of (iii) an aqueous solution of a water- soluble alkaline material and (iv) a water-insoluble solvent for (ii), the amounts of components (i), (ii) and (iii) being sufficient to acylate at least one amino nitrogen atom containing at least one nitrogen-bonded hydrogen atom per molecule of aminosilicon compound and to provide at least an equivalent amount of alkaline material relative to the amount of acyl halide, and thereafter (II) agitating the mixture comprising (i) and (ii) until the compound is formed.
Claim 9
Dependent Claim
65 words
A method according to claim 6 wherein the silicon-bonded amino-substituted hydrocarbon radical has the formula --Q(NHQ') a NZH and the acyl halide has the formula R"COX, wherein Q and Q' denote divalent hydrocarbon radicals, R" denotes a substituted or unsubstituted monovalent hydrocarbon radical, X denotes a halogen atom, Z denotes hydrogen or a monovalent hydrocarbon radical and a has a value of 0 or 1.
Claim 10
Dependent Claim
28 words
A method according to claim 7 wherein the acyl halide comprises a compound selected from the group consisting of CH 2 ═CHCOCl and CH 2 ═C(CH 3 )COCl.
Claim 11
Dependent Claim
57 words
A method according to claim 8 wherein the aminosilicon compound has the average unit formula R c (NH 2 (Q'NH) a Q) d SiO.sub.(4-c-d)/2 wherein R denotes a monovalent hydrocarbon radical, c has a value of from 0 to 3, d has a value of >0 to 4, and c+d has a value of 1 to 4.
Claim 12
Dependent Claim
58 words
A method according to claim 9 wherein the aminosilicon compound is a siloxane having the formula Y'R 2 SiO(R 2 SiO) x (Y'RSiO) y SiR 2 Y' wherein Y' denotes R or --QNHCH 2 CH 2 NH 2 , x has a value of from 0 to 5000 and y has a value of from 0 to 500.
Claim 13
Dependent Claim
37 words
A method according to claim 9 wherein the aminosilicon compound is a silane having the formula R e Si(QNHCH 2 CH 2 NH 2 ) 4-e wherein e has a value of 0, 1, 2, or 3.
Claim 14
Dependent Claim
19 words
A method according to claim 9 wherein R is selected from the group consisting of methyl, phenyl and vinyl.
Claim 15
Dependent Claim
15 words
A method according to claim 6 wherein the alkaline material is an alkali metal hydroxide.
Claim 16
Dependent Claim
20 words
A method according to claim 6 wherein component (i) is admixed to a mixture of components (ii), (iii), and (iv).
Claim 17
Dependent Claim
21 words
A method according to claim 6 further comprising (III) isolating the organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical.
Claim 18
Dependent Claim
28 words
A method according to claim 6 wherein the acyl halide comprises a compound selected from the group consisting of CH 2 ═CHCOCl and CH 2 ═C(CH 3 )COCl.
Claim 19
Dependent Claim
23 words
A method according to claim 6 wherein said admixing and said agitating is done at a temperature of from 0 to 10° C.
Claim 20
Dependent Claim
23 words
A method according to claim 8 wherein said admixing and said agitating is done at a temperature of from 0° to 10° C.
Claim 21
Dependent Claim
23 words
A method according to claim 15 wherein said admixing and said agitating is done at a temperature of from 0 to 10° C.
Claim 22
Dependent Claim
77 words
A curable coating composition comprising an organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical having the formula --QANQ'NAZ, wherein Z denotes H or R, R denotes a monovalent hydrocarbon radical, Q and Q' denote divalent hydrocarbon radicals, A denotes an acyl radical having the formula ##STR51## and B denotes H or CH 3 , any remaining silicon-bonded radicals therein being selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms.
Claim 23
Dependent Claim
77 words
A curable coating composition comprising an organosilicon compound containing at least one silicon-bonded acylamino-substituted hydrocarbon radical having the formula --QANQ'NAZ, wherein Z denotes H or R, R denotes a monovalent hydrocarbon radical, Q and Q' denote divalent hydrocarbon radicals, A denotes an acyl radical having the formula ##STR51## and B denotes H or CH 3 , any remaining silicon-bonded radicals therein being selected from the group consisting of organic radicals and divalent oxygen atoms linking silicon atoms.
Claim 24
Dependent Claim
13 words
A curable coating composition according to claim 20 further comprising a polymerization initiator.
Claim 25
Dependent Claim
55 words
A curable coating composition according to claim 20 wherein the organosilicon compound has the formula YR 2 SiO(R 2 SiO) z (YRSiO) g SiR 2 Y wherein Y denotes R or --QNACH 2 CH 2 NAH, z has a value of from 10 to 2000 and g has a value of from 0 to 0.1z.
Claim 26
Dependent Claim
12 words
A curable composition according to claim 22 further comprising a polymerization initiator.
Claim 27
Dependent Claim
15 words
A curable coating composition according to claim 22 wherein each R denotes the methyl radical.
Claim 28
Dependent Claim
37 words
A curable coating composition according to claim 24 wherein the organosilicon compound has the formula Me 3 SiO(Me 2 SiO) z (YMeSiO) h SiMe 3 and h has a value of from greater than zero to 0.1z.
Claim 29
Dependent Claim
24 words
A curable coating composition according to claim 24 wherein the organosilicon compound has the formula YMe 2 SiO(Me 2 SiO) z SiMe 2 Y.
Claim 30
Dependent Claim
38 words
A curable coating composition according to claim 24 wherein the organosilicon compound has the formula YMe 2 SiO(Me 2 SiO) z (YMeSiO) h SiMe 2 Y and h has a value of from greater than zero to 0.1z.
Claim 31
Dependent Claim
33 words
A process for providing a cured silicon-containing coating on a substrate, said process comprising (A) applying the curable coating composition of claim 20 to the substrate and thereafter (B) curing the applied coating.
Claim 32
Dependent Claim
22 words
A process according to claim 28 wherein said curing is done by exposing the applied coating to a free radical generating means.
Claim 33
Dependent Claim
20 words
A process according to claim 28 wherein said curing is done by exposing the applied coating to electron beam radiation.
Claim 34
Dependent Claim
19 words
A process according to claim 28 wherein said curing is done by exposing the applied coating to ultraviolet radiation.
Claim 35
Dependent Claim
33 words
A process for providing a cured silicone coating on a substrate, said process comprising (A) applying the curable coating composition of claim 22 to the substrate and thereafter (B) curing the applied coating.
Claim 36
Dependent Claim
22 words
A process according to claim 32 wherein said curing is done by exposing the applied coating to a free radical generating means.
Claim 37
Dependent Claim
20 words
A process according to claim 32 wherein said curing is done by exposing the applied coating to electron beam radiation.
Claim 38
Dependent Claim
19 words
A process according to claim 32 wherein said curing is done by exposing the applied coating to ultraviolet radiation.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-25 | 1990-02-24 | 1990-08-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-25 | 1994-02-24 | 1994-08-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-25 | 1998-02-24 | 1998-08-26 | $7700.00 | Window Closed / Lapsed |