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US5084490A
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Styryloxy compounds and polymers thereof
Assignee: Henkel Loctite Ireland Ltd
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Filing: 1990-12-10
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Granted: 1992-01-28
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Expires: 2010-12-10
Abstract
Abstract Styryloxy compounds of the formula IV ##STR1## wherein R 1 and R 2 are H, or one of R 1 and R 2 is H and the other is methyl; R 7 and R 8 (which may be the same or different) are H, C 1 -C 5 alkyl or C 1 -C 5 alkenyl; or one of R 7 and R 8 may be --OR 6 or C 1 -C 5 alkoxy or C 1 -C 5 alkenyloxy if R 2 is not methyl; R 6 is selected from the group consisting of: ##STR2## where R 10 is C 1 -C 5 alkyl; and R 11 , R 12 and R 13 , which may be the same or different, are H or C 1 -C 5 alkyl, are described as new low viscosity liquid styryloxy monomers which can be photocured and which form transparent polymers. They have an advantageous effect in a mixture with 4-allyloxystyrene, and this mixture has a synergistic effect in combination with divinyl ethers of a polyalkylene oxide.
Inventors
- 👤 Ciaran B. McArdle
- 👤 Joseph Burke
- 👤 John G. Woods
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:02
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C08; C08F; C08F12/00; C08F12/34
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
129 words
Styryloxy compounds of the formula IV ##STR12## wherein R 1 and R 2 are H, or one of R 1 and R 2 is H and the other is methyl; R 7 and R 8 (which may be the same or different) are H, C 1 -C 5 alkyl or C 1 -C 5 alkenyl; or one of R 7 and R 8 may be --OR 6 or C 1 -C 5 alkoxyl or C 1 -C 5 alkenyloxy if R 2 is not methyl; R 6 is selected from the group consisting of: ##STR13## where R 10 is C 1 -C 5 alkyl; and R 11 , R 12 and R 13 , which may be the same of different, are H or C 1 -C 5 alkyl.
Claim 2
Dependent Claim
129 words
Styryloxy compounds of the formula IV ##STR12## wherein R 1 and R 2 are H, or one of R 1 and R 2 is H and the other is methyl; R 7 and R 8 (which may be the same or different) are H, C 1 -C 5 alkyl or C 1 -C 5 alkenyl; or one of R 7 and R 8 may be --OR 6 or C 1 -C 5 alkoxyl or C 1 -C 5 alkenyloxy if R 2 is not methyl; R 6 is selected from the group consisting of: ##STR13## where R 10 is C 1 -C 5 alkyl; and R 11 , R 12 and R 13 , which may be the same of different, are H or C 1 -C 5 alkyl.
Claim 3
Dependent Claim
23 words
According to claim 1 wherein at least one of R 11 , R 12 and R 13 is C 1 -C 5 alkyl.
Claim 4
Dependent Claim
19 words
Compounds according to claim 1 wherein R 1 , R 2 , R 7 and R 8 are H.
Claim 5
Dependent Claim
20 words
Compounds according to claim 1 wherein the styryl moiety (R 2 CH═C(R 1 )--) is para to --OR 6 .
Claim 6
Dependent Claim
16 words
Compounds according to claim 4 wherein at least one position ortho to --OR 6 is unsubstituted.
Claim 7
Dependent Claim
23 words
Compounds according to claim 1 which are of the formula V ##STR14## wherein R 9 is selected from the group consisting of: ##STR15##
Claim 8
Dependent Claim
19 words
A polymerizable composition comprising a styryloxy compound of formula IV as defined in claim 1 together with a photoinitiator.
Claim 9
Dependent Claim
23 words
A polymerizable composition comprising 4-allyloxystyrene in admixture with a styryloxy compound of formula IV as defined in claim 1 together with a photoinitiator.
Claim 10
Dependent Claim
41 words
A composition according to claim 8 wherein the styryloxy compound of formula IV is present in an amount of from about 1 to about 99% by weight based on the combined weight of 4-allyloxystyrene and the styryloxy compound of formula IV.
Claim 11
Dependent Claim
41 words
A composition according to claim 8 wherein the styryloxy compound of formula IV is present in an amount of from about 2.5 to about 35% by weight based on the combined weight of 4-allyloxystyrene and the styryloxy compound of formula IV.
Claim 12
Dependent Claim
41 words
A composition according to claim 8 wherein the styryloxy compound of formula IV is present in an amount of from about 3 to about 10% by weight based on the combined weight of 4-allyloxystyrene and the styryloxy compound of formula IV.
Claim 13
Dependent Claim
63 words
A photopolymerizable composition comprising: (A) a styryloxy component selected from the group consisting of (i) 4-allyloxystyrene, (ii) at least one styryloxy compound of formula IV as defined in claim 1 and (iii) a mixture of (i) and (ii) above, (B) a divinyl ether of a polyalkylene oxide and (C) a photoinitiator, the ratio of (A):(B) being in the range from 1:9 to 20:1.
Claim 14
Dependent Claim
16 words
A composition according to claim 12 wherein the ratio of (A):(B) is from 2:1 to 9:1.
Claim 15
Dependent Claim
17 words
A composition according to claim 12 where in the ratio of (A):(B) is from 1:1 to 4:1.
Claim 16
Dependent Claim
25 words
A composition, according to claim 12 wherein the styryloxy compound is a mixture (iii) of 4-allyloxystyrene (i) and a styryloxy compound of formula IV (ii).
Claim 17
Dependent Claim
16 words
A composition according to claim 15 wherein the ratio of (i):(ii) is from 20:1 to 1:2.
Claim 18
Dependent Claim
16 words
A composition according to claim 15 wherein the ratio of (i):(ii) is from 7.5:1 to 2:1.
Claim 19
Dependent Claim
16 words
A composition according to claim 15 wherein the ratio of (i):(ii) is from 6:1 to 3:1.
Claim 20
Dependent Claim
33 words
A composition according to claim 12 wherein the divinyl ether of a polyalkylene oxide is of the formula: CH.sub.2 ═CH--O--(CH.sub.2).sub.n --O].sub.m CH═CH.sub.2 wherein n=1-6 and m is greater than or equal to 2.
Claim 21
Dependent Claim
16 words
A composition according to claim 19 wherein n is 2 and m is 2 to 10.
References Cited (Backward Citations)
US4543397A
Cited
US4732956A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-01-27 | 1995-07-29 | 1996-01-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-01-27 | 1999-07-29 | 2000-01-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-01-27 | 2003-07-29 | 2004-01-28 | $7700.00 | Window Closed / Lapsed |