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US4606933A
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Acrylate-functional organopolysiloxanes
Assignee: Wacker Chemical Corp
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Filing: 1985-09-25
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Granted: 1986-08-19
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Expires: 2005-09-25
Abstract
Abstract Radiation polymerizable acrylate-functional organopolysiloxanes having the formula ##STR1## where R is a radical selected from monovalent hydrocarbon radicals, substituted monovalent hydrocarbon radicals having from 1 to 20 carbon atoms or monovalent hydrocarbonoxy radicals having from 1 to 20 carbon atoms, or a radical of the formula ##STR2## in which at least one R is a radical having the above formula, R 1 is a divalent radical selected from a saturated divalent hydrocarbon radical having up to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 3 to 10 carbon atoms; R 2 is hydrogen or a methyl radical; R 3 is a linear or branched radical having 2, 3, 4, 5 or 6 valences in which the radical is selected from a substituted hydrocarbon radical, or a hydrocarbon ether or thioether radical having one or more repeating units and the terminal atoms of the R 3 radical are selected from oxygen or nitrogen; R 4 is a radical linked to the terminal oxygen or nitrogen atoms of R 3 and is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, an acryloyl radical, and a substituted acryloyl radical and when the terminal atom of R 3 is oxygen, then R 4 may also be hydrogen. R 5 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms or a radical of the formula --CH.sub.2 --CH.sub.2 --X wherein X represents --COOR 6 , --CONR 6 , --CN, --SO 2 R 6 , R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, a is a number having an average value of 0.7 to 2.6, b is a number of from 1 to 3, c is a number of from 0 to 4, d is a number of from 1 to 4, e is a number of from 0 to 4, x is a number of from 2 to 20,000 with the proviso that b+1=d+e. The acrylate-functional organopolysiloxanes are combined with a photosensitizer and/or peroxide and cured by radiation and/or heat.
Inventors
- 👤 Roy M. Griswold
- 👤 Walter L. Magee
- 👤 Paul A. Manis
- 👤 Eugene R. Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 13:01
CPC Classifications
C; C08; C08F; C08F299/00; C08F299/02; C08F299/08; C03; C03C; C03C17/00; C03C17/28; C03C17/30; C08G; C08G77/00; C08G77/04; C08G77/22; C08G77/26; C08G77/38; C08G77/382; C08G77/388; C08L; C08L83/00; C08L83/04; C08L83/08; C09; C09D; C09D155/00; C09D155/005; D; D21; D21H; D21H19/00; D21H19/10; D21H19/14; D21H19/24; D21H19/32; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 66
Claim 1
Independent Claim
375 words
A polymerizable acrylate-functional organopolysiloxane composition comprising an organopolysiloxane of the formula ##STR43## where R is selected from the group consisting of a monovalent hydrocarbon radical, a substituted monovalent hydrocarbon radical having from 1 to 20 carbon atoms, a monovalent hydrocarbonoxy radical having from 1 to 20 carbon atoms and a radical of the formula ##STR44## where at least one R is a radical having the above formula, R 1 is a divalent radical selected from the group consisting of a saturated divalent hydrocarbon radical having from 1 to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms; R 2 is selected from the group consisting of hydrogen, a methyl radical and mixtures thereof, R 3 is a radical having 2, 3, 4, 5 or 6 valences in which the radical is selected from the group consisting of a substituted hydrocarbon radical, a hydrocarbon ether radical, a thioether radical and the terminal atoms of the R 3 radical are selected from the group consisting of oxygen and nitrogen; R 4 is a radical linked to the terminal oxygen or nitrogen atcms of R 3 and is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, an acryloyl radical and a substituted acryloyl radical and when the terminal atom of R 3 is oxygen, then R 4 may be hydrogen; R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and --SO 2 R 6 ; R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, a is a number having an average value of 0.7 to 2.6, b is a number of from 1 to 3, c is a number of from 0 to 4, d is a number of from 1 to 4, e is a number of from 0 to 4, x is a number of from 2 to 20,000 with the proviso that b+1=d+e.
Claim 2
Dependent Claim
375 words
A polymerizable acrylate-functional organopolysiloxane composition comprising an organopolysiloxane of the formula ##STR43## where R is selected from the group consisting of a monovalent hydrocarbon radical, a substituted monovalent hydrocarbon radical having from 1 to 20 carbon atoms, a monovalent hydrocarbonoxy radical having from 1 to 20 carbon atoms and a radical of the formula ##STR44## where at least one R is a radical having the above formula, R 1 is a divalent radical selected from the group consisting of a saturated divalent hydrocarbon radical having from 1 to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms; R 2 is selected from the group consisting of hydrogen, a methyl radical and mixtures thereof, R 3 is a radical having 2, 3, 4, 5 or 6 valences in which the radical is selected from the group consisting of a substituted hydrocarbon radical, a hydrocarbon ether radical, a thioether radical and the terminal atoms of the R 3 radical are selected from the group consisting of oxygen and nitrogen; R 4 is a radical linked to the terminal oxygen or nitrogen atcms of R 3 and is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, an acryloyl radical and a substituted acryloyl radical and when the terminal atom of R 3 is oxygen, then R 4 may be hydrogen; R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and --SO 2 R 6 ; R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, a is a number having an average value of 0.7 to 2.6, b is a number of from 1 to 3, c is a number of from 0 to 4, d is a number of from 1 to 4, e is a number of from 0 to 4, x is a number of from 2 to 20,000 with the proviso that b+1=d+e.
Claim 3
Dependent Claim
19 words
The composition of claim 1, wherein the R 3 radical is a substituted hydrocarbon radical having terminal oxygen atoms.
Claim 4
Dependent Claim
20 words
The composition of claim 1, wherein the R 3 radical provides sites for linking up to four additional acryloyl radicals.
Claim 5
Dependent Claim
11 words
The composition of claim 1, wherein the composition contains a photosensitizer.
Claim 6
Dependent Claim
12 words
The composition of claim 1, wherein the composition contains an organic peroxide.
Claim 7
Dependent Claim
12 words
The composition of claim 4, wherein the composition contains an organic peroxide.
Claim 8
Dependent Claim
31 words
The composition of claim 4, wherein the photosensitizer is present in an amount of from about 0.5 to about 20 percent by weight based on the weight of the acrylate-functional organopolysiloxane.
Claim 9
Dependent Claim
31 words
The composition of claim 5, wherein the organic peroxide is present in an amount of from about 0.1 to 10 percent by weight based on the weight of the acrylate-functional organopolysiloxane.
Claim 10
Dependent Claim
20 words
The composition of claim 1, wherein R 1 is a divalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 11
Dependent Claim
21 words
The composition of claim 1, wherein R 1 is an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms.
Claim 12
Dependent Claim
60 words
The composition of claim 1, wherein R 1 is a divalent hydrocarbonoxy radical of the formula (CH.sub.2).sub.d (OC.sub.g H.sub.2g).sub.k, where d is a number of from 1 to 4, g is 2, 3 or 4, k is at least 1 and the sum of d+k is a number such that the hydrocarbonoxy radical has from 3 to 20 carbon atoms.
Claim 13
Dependent Claim
19 words
The composition of claim 1, wherein the terminal atoms of R 3 are oxygen and R 4 is hydrogen.
Claim 14
Dependent Claim
20 words
The composition of claim 1, wherein R 4 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 15
Dependent Claim
12 words
The composition of claim 1, wherein R 4 is an acryloyl radical.
Claim 16
Dependent Claim
20 words
The composition of claim 1, wherein R 5 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 17
Dependent Claim
52 words
The composition of claim 1, wherein R 5 is a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and SO 2 R 6 and R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 18
Dependent Claim
10 words
The composition of claim 1, wherein R 2 is hydrogen.
Claim 19
Dependent Claim
10 words
The composition of claim 4, wherein R 2 is hydrogen.
Claim 20
Dependent Claim
10 words
The composition of claim 5, wherein R 2 is hydrogen.
Claim 21
Dependent Claim
10 words
The composition of claim 6, wherein R 2 is hydrogen.
Claim 22
Dependent Claim
30 words
The composition of claim 1, wherein R 5 is a radical of the formula ##STR45## where R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 23
Dependent Claim
30 words
The composition of claim 17, wherein R 5 is a radical of the formula ##STR46## where R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 24
Dependent Claim
30 words
The composition of claim 18, wherein R 5 is a radical of the formula ##STR47## where R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 25
Dependent Claim
30 words
The composition of claim 19, wherein R 5 is a radical of the formula ##STR48## where R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 26
Dependent Claim
30 words
The composition of claim 20, wherein R 5 is a radical of the formula ##STR49## where R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms.
Claim 27
Independent Claim
201 words
A method for preparing a polymerizable acrylate functional organopolysiloxane composition which comprises reacting an aminofunctional organopolysiloxane having at least one unit of the formula ##STR50## where R 1 is a divalent radical selected from the group consisting of a saturated divalent hydrocarbon radical having from 1 to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms; R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and --SO 2 R 6 ; R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, R 10 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, b is a number of from 1 to 3, e is a number of from 0 to 4, m is 0, 1 or 2 and n is a number of from 1 to 5, with the proviso that n=b-e+1 with a polyacrylate containing compound.
Claim 28
Independent Claim
201 words
A method for preparing a polymerizable acrylate functional organopolysiloxane composition which comprises reacting an aminofunctional organopolysiloxane having at least one unit of the formula ##STR50## where R 1 is a divalent radical selected from the group consisting of a saturated divalent hydrocarbon radical having from 1 to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms; R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and --SO 2 R 6 ; R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, R 10 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, b is a number of from 1 to 3, e is a number of from 0 to 4, m is 0, 1 or 2 and n is a number of from 1 to 5, with the proviso that n=b-e+1 with a polyacrylate containing compound.
Claim 29
Dependent Claim
19 words
The method of claim 26, wherein the reaction is conducted at a temperature of from 25° to 150° C.
Claim 30
Dependent Claim
17 words
The method of claim 26, wherein the reaction is conducted in the presence of a hydrocarbon solvent.
Claim 31
Dependent Claim
27 words
The method of claim 26, wherein the molar ratio of the polyacrylate containing compound to the amine groups of the aminofunctional organopolysiloxane is from 0.75 to 10.
Claim 32
Dependent Claim
55 words
The method of claim 26, wherein the aminofunctional organopolysiloxane is obtained from the reaction of an aminofunctional silane having at least one hydrocarbonoxy group linked to a silicon atom with an organopolysiloxane selected from the group consisting of an organopolysiloxane having at least one hydroxyl group linked to a silicon atom and a cyclic trisiloxane.
Claim 33
Independent Claim
52 words
A method for preparing a polymerizable acrylate-functional organopolysiloxane composition which comprises reacting an acrylate-functional aminosilane having at least one hydrocarbonoxy group linked to a silicon atom with an organopolysiloxane selected from the group consisting of an organopolysiloxane having at least one hydroxyl group linked to a silicon atom and a cyclic trisiloxane.
Claim 34
Independent Claim
52 words
A method for preparing a polymerizable acrylate-functional organopolysiloxane composition which comprises reacting an acrylate-functional aminosilane having at least one hydrocarbonoxy group linked to a silicon atom with an organopolysiloxane selected from the group consisting of an organopolysiloxane having at least one hydroxyl group linked to a silicon atom and a cyclic trisiloxane.
Claim 35
Dependent Claim
46 words
The method of claim 31, wherein the acrylate-functional aminosilane is reacted with an organopolysiloxane having at least one hydroxyl group linked to the silicon atom of the organopolysiloxane in the presence of a catalyst which promotes the reaction of the hydrocarbonoxy group with the hydroxyl group.
Claim 36
Dependent Claim
70 words
The method of claim 31, wherein the hydroxyl-containing organopolysiloxane is represented by the formula ##STR51## where R" is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and hydroxyl radicals, in which at least one R" per molecule is a hydroxyl radical, n' has an average value of from 1.8 to 2.2 and x is a number of from 2 to 20,000.
Claim 37
Dependent Claim
32 words
The method of claim 31, wherein the molar ratio of acrylate-functional aminosilane to hydroxyl-containing organopolysiloxane may range from about 0.5 to 6 moles of acrylate-functional aminosilane per mole of hydroxyl containing organopolysiloxane.
Claim 38
Dependent Claim
19 words
The method of claim 31, wherein the reaction is conducted at a temperature of from 25° to 175° C.
Claim 39
Dependent Claim
17 words
The method of claim 31, wherein the reaction is conducted in the presence of an inert solvent.
Claim 40
Dependent Claim
12 words
The method of claim 32, wherein the catalyst is an organic amine.
Claim 41
Dependent Claim
12 words
The method of claim 32, wherein the catalyst is a lithium compound.
Claim 42
Dependent Claim
23 words
The method of claim 33, wherein the hydroxyl-containing organopolysiloxane has a viscosity of from about 25 to about 500,000 mPa.s at 25° C.
Claim 43
Dependent Claim
23 words
The method of claim 31, wherein the acrylate-functional aminosilane is obtained from the reaction of an aminofunctional silane and a polyacrylate containing compound.
Claim 44
Dependent Claim
186 words
The method of claim 40, wherein the aminofunctional silane is represented by the formula ##STR52## wherein R 1 is a divalent radical selected from the group consisting of a saturated divalent hydrocarbon radical having from 1 to 20 carbon atoms, a divalent hydrocarbonoxy radical in which the oxygen is in the form of an ether linkage and an unsaturated divalent hydrocarbon radical having from 2 to 20 carbon atoms; R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and a radical of the formula --CH.sub.2 --CH.sub.2 --X; X is selected from the group consisting of --COOR 6 , --CONR 6 , --CN and --SO 2 R 6 ; R 6 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, R 10 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, b is a number of from 1 to 3, e is a number of from 0 to 4, m is 0, 1 or 2, and n is a number of from 1 to 5, with the proviso that n=b-e+1.
Claim 45
Dependent Claim
12 words
The method of claim 40, wherein the polyacrylate-containing compound is trimethylol triacrylate.
Claim 46
Dependent Claim
12 words
The method of claim 40, wherein the polyacrylate-containing compound is pentaerythritol triacrylate.
Claim 47
Dependent Claim
12 words
The method of claim 39, wherein the polyacrylate-containing compound is hexanediol diacrylate.
Claim 48
Dependent Claim
20 words
The method of claim 40, wherein the acrylate is a mixture consisting of a polyacrylate-containing compound and a monoacrylate-containing compound.
Claim 49
Dependent Claim
27 words
The method of claim 40, wherein the molar ratio of the polyacrylate containing compound to the amine groups of the aminofunctional silane is from 0.75 to 10.
Claim 50
Dependent Claim
17 words
The method of claim 40, wherein the reaction is conducted in the presence of an organic solvent.
Claim 51
Dependent Claim
11 words
The method of claim 40, wherein the aminofunctional silane is gamma-aminopropyltriethoxysilane.
Claim 52
Dependent Claim
12 words
The method of claim 31, wherein the organopolysiloxane is a cyclic trisiloxane.
Claim 53
Dependent Claim
17 words
The method of claim 49, wherein the reaction is conducted in the presence of a lithium compound.
Claim 54
Dependent Claim
12 words
The method of claim 50, wherein the lithium compound is lithium silanolate.
Claim 55
Dependent Claim
19 words
The method of claim 49, wherein the reaction is conducted at a temperature of from 70° to 150° C.
Claim 56
Dependent Claim
17 words
The method of claim 49, wherein the reaction is conducted in the presence of a hydrocarbon solvent.
Claim 57
Dependent Claim
21 words
The method of claim 49, wherein the molar ratio of acrylate-containing aminosilane to cyclic trisiloxane is from about 0.00015 to 3.
Claim 58
Dependent Claim
11 words
The method of claim 49, wherein the cyclic trisiloxane is hexamethylcyclotrisiloxane.
Claim 59
Dependent Claim
26 words
A method for coating a substrate which comprises applying the composition of claim 4 to a substrate and thereafter exposing the composition to a radiation source.
Claim 60
Dependent Claim
12 words
The method of claim 56, wherein the radiation source is ultraviolet light.
Claim 61
Dependent Claim
24 words
The method of claim 56, wherein the composition of claim 5, is applied to a substrate and thereafter exposed to a source of heat.
Claim 62
Dependent Claim
24 words
The method of claim 56, wherein the composition of claim 6 is applied to a substrate and thereafter exposed to a source of radiation.
Claim 63
Dependent Claim
10 words
The coated substrate obtained from the method of claim 56.
Claim 64
Dependent Claim
10 words
The coated substrate obtained from the method of claim 57.
Claim 65
Dependent Claim
10 words
The coated substrate obtained from the method of claim 58.
Claim 66
Dependent Claim
10 words
The coated substrate obtained from the method of claim 59.
References Cited (Backward Citations)
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| 7.5 Years (Year 8) | 1993-08-18 | 1994-02-17 | 1994-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-18 | 1998-02-17 | 1998-08-19 | $7700.00 | Window Closed / Lapsed |