US4134814A
Expired / Lapsed
US
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Halogenated photopolymerizable adhesives
Assignee: UCB Inc
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Filing: 1976-05-03
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Granted: 1979-01-16
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Expires: 1996-05-03
Abstract
Abstract Halogenated photopolymerizable adhesive, which comprises: (a) 20 to 70% by weight of at least one halogenated polymer, which: (1) has a chain interrupted by at least one oxygen or nitrogen atom, (2) contains from 4 to 70% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp2, (called "active halogen atoms"), (3) has an average molecular weight between 700 and 10,000 and (4) has a glass transition temperature (Tg) between -80 DEG C and 20 DEG C; (b) 5 to 30% by weight of at least one organic monomer compound containing at least two acrylic and/or methacrylic acid radicals and containing from 0 to 65% by weight of active halogen atoms; (c) 20 to 70% by weight of at least one organic monomer compound containing an acrylic or methacrylic acid radical and containing from 0 to about 65% by weight of active halogen atoms; (d) about 1 to about 25% by weight of a photo-initiator system comprising: (1) 0.5 to 100% by weight of at least one aromatic ketone, (2) 0 to 99.5% by weight of at least one tertiary amine, at least one carbon atom of which, in the alpha position with regard to the nitrogen atom, carries at least one hydrogen atom, (3) 0 to 90% by weight of an aromatic or nonaromatic alpha-dione, the sum of (1) + (2) + (3) representing 100% by weight of the photo-initiator system, the total content of active halogen atoms amonting to 3 to 50% by weight of the total halogenated photopolymerizable adhesive and lamination or contact adhesives based on said halogenated photopolymerizable adhesive.
Inventors
- 👤 Michel De Poortere
- 👤 Marc Colpaert
- 👤 Paul Dufour
- 👤 August Vrancken
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:27
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/032; C; C09; C09J; C09J167/00; C09J4/00; C09J4/06; C08; C08L; C08L2666/00; C08L2666/28; C08L2666/34; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31786; Y10T428/31794
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
288 words
A halogenated photopolymerizable adhesive, which comprises: (a) 20 to 70% by weight of at least one halogenated polymer, which: (1) has a chain interrupted by at least one oxygen or nitrogen atom, (2) contains from 4 to 70% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 , (3) has an average molecular weight between about 700 and about 10,000 and (4) has a glass transition temperature (Tg) between about -80° C. and 20° C.; (b) 5 to 30% by weight of at least one organic monomer compound containing at least two acrylic and/or methacrylic acid radicals and containing from 0 to 65% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 ; (c) 20 to 70% by weight of at least one organic monomer compound containing an acrylic or methacrylic acid radical and containing from 0 to about 65% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 ; (d) about 1 to about 25% by weight of a photo-initiator system comprising: (1) 0.5 to 100% by weight of at least one aromatic ketone, (2) 0 to 99.5% by weight of at least one tertiary amine, at least one carbon atom of which, in the alpha position with regard to the nitrogen atom, carries at least one hydrogen atom, (3) 0 to 90% by weight of an aromatic or non-aromatic alpha-dione, the sum of (1) + (2) + (3) representing 100% by weight of the photoinitiator system; the total content of halogen atoms attached to carbon atoms having the electronic configuration sp 2 amounting to from about 3 to about 50% by weight of the total halogenated photopolymerizable adhesive.
Claim 2
Dependent Claim
288 words
A halogenated photopolymerizable adhesive, which comprises: (a) 20 to 70% by weight of at least one halogenated polymer, which: (1) has a chain interrupted by at least one oxygen or nitrogen atom, (2) contains from 4 to 70% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 , (3) has an average molecular weight between about 700 and about 10,000 and (4) has a glass transition temperature (Tg) between about -80° C. and 20° C.; (b) 5 to 30% by weight of at least one organic monomer compound containing at least two acrylic and/or methacrylic acid radicals and containing from 0 to 65% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 ; (c) 20 to 70% by weight of at least one organic monomer compound containing an acrylic or methacrylic acid radical and containing from 0 to about 65% by weight of halogen atoms attached to carbon atoms having the electronic configuration sp 2 ; (d) about 1 to about 25% by weight of a photo-initiator system comprising: (1) 0.5 to 100% by weight of at least one aromatic ketone, (2) 0 to 99.5% by weight of at least one tertiary amine, at least one carbon atom of which, in the alpha position with regard to the nitrogen atom, carries at least one hydrogen atom, (3) 0 to 90% by weight of an aromatic or non-aromatic alpha-dione, the sum of (1) + (2) + (3) representing 100% by weight of the photoinitiator system; the total content of halogen atoms attached to carbon atoms having the electronic configuration sp 2 amounting to from about 3 to about 50% by weight of the total halogenated photopolymerizable adhesive.
Claim 3
Dependent Claim
15 words
The adhesive according to claim 1, wherein the halogenated polymer (a) is a halogenated polyester.
Claim 4
Dependent Claim
16 words
The adhesive according to claim 2, wherein the halogenated polyester does not contain any polymerizable unsaturation.
Claim 5
Dependent Claim
14 words
The adhesive according to claim 2, wherein the halogenated polyester contains polymerizable ethylenic unsaturation.
Claim 6
Dependent Claim
31 words
The adhesive according to claim 2, wherein the acid component with active halogen atoms of the halogenated polyester is selected from 1,4,5,6,7,7-hexachloro-bicyclo[2,2,1]-hept-5-ene-2,3-dicarboxylic acid, 1,4,5,6,7,7-hexachloro-bicyclo[2,2,1]-hept-5-ene-2-carboxylic acid, tetrachlorophthalic acid, tetrabromophthalic acid and 2,3,5,6,2',3',5',6'-octabromo-4,4'-di(3-carboxypropoxy)biphenyl.
Claim 7
Dependent Claim
30 words
The adhesive according to claim 2, wherein the acid component without active halogen atoms of the halogenated polyester is selected from phthalic acid, benzoic acid, adipic acid and trimellitic acid.
Claim 8
Dependent Claim
41 words
The adhesive according to claim 2, wherein the alcohol component without active halogen atoms of the halogenated polyester is selected from ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, hydrogenated bisphenol A, oxyethylated bisphenol A, tricyclodecane-dimethanol, trimethylolpropane and dipentaerythritol.
Claim 9
Dependent Claim
56 words
The adhesive according to claim 1, wherein the organic monomer compound (b) is a condensation product of (1) at least one polyalcohol containing 2 to 6 hydroxyl groups with (2) at least one alpha,beta-ethylenically unsaturated monocarboxylic acid containing 3 or 4 carbon atoms and with or without (3) at least one organic mono- to tetracarboxylic acid.
Claim 10
Dependent Claim
15 words
The adhesive according to claim 1, wherein the organic monomer compound (b) is 2,3,5,6,2',3',5',6'-octachloro-4,4-di-(2-(2-hydroxyethoxy)-ethoxy-biphenyl diacrylate.
Claim 11
Dependent Claim
70 words
The adhesive according to claim 1, wherein the organic monomer compound (b) is selected from diethylene glycol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, oxypropylated glycerol triacrylate, pentaerythritol tetraacrylate, the condensation product of 1 mole C 36 -dimer acid, 2 moles pentaerythritol and 6 moles acrylic acid and the condensation product of 1 mole C 36 -dimer acid, 2 moles 1,6-hexanediol and 2 moles acrylic acid.
Claim 12
Dependent Claim
28 words
The adhesive according to claim 1, wherein the organic monomer compound (c) is a monoacrylate or a monomethacrylate of a mono- or polyhydric aliphatic, alicyclic or aromatic alcohol.
Claim 13
Dependent Claim
15 words
The adhesive according to claim 1, wherein the organic monomer compound (c) is 3-(pentachlorophenoxy)-propan-1-ol acrylate.
Claim 14
Dependent Claim
44 words
The adhesive according to claim 1, wherein the organic monomer compound (c) is selected from benzyl acrylate, 2-(2-phenoxyethoxy)-ethyl acrylate and the product obtained by esterifying, with acrylic acid, an ethyl acrylate-butyl acrylate-2-hydroxyethyl acrylate copolymer containing an average of one acrylic double bond per molecule.
Claim 15
Dependent Claim
50 words
The adhesive according to claim 1, wherein the aromatic ketone (1) of the photoinitiator system (d) is selected from benzophenone, Michler's ketone, 2-ethyl-anthraquinone, 2-chloro-thioxanthone and 1,6-hexanediol acrylate o-benzoylbenzoate; the tertiary amine (2) is selected from triethanolamine, diethylene glycol acrylate betadimethylamino-propionate and 1,6-hexanediol acrylate beta-dimethylamino-propionate, and the alpha-dione (3) is benzil.
Claim 16
Dependent Claim
29 words
The adhesive according to claim 1, wherein the halogenated polymer a) is the only component having halogen atoms fixed onto carbon atoms having the electronic configuration sp 2 .
Claim 17
Dependent Claim
36 words
The adhesive according to claim 1, wherein both the halogenated polymer (a) and one of the organic monomer compounds (b) or (c) contain halogen atoms fixed onto carbon atoms having the electronic configuration sp 2 .
Claim 18
Dependent Claim
29 words
The adhesive according to claim 1, wherein each of the components (a), (b) and (c) contains halogen atoms fixed onto carbon atoms having the electronic configuration sp 2 .
Claim 19
Dependent Claim
42 words
Process for the preparation of the adhesive according to claim 1, which comprises homogenously mixing together the components (a), (b), (c) and (d), at room temperature or at a temperature higher than room temperature but sufficiently low to avoid a premature polymerization.
Claim 20
Dependent Claim
28 words
A lamination or contact adhesive composition, which comprises: the adhesive according to claim 1 alone or in admixture with non-copolymerizable inert polymers, inert plasticizers and transparent filling materials.
Claim 21
Dependent Claim
28 words
The adhesive according to claim 2, wherein the alcohol component with active halogen atoms of the halogenated polyester is selected from the group consisting of 2,3,5,6,2',3',5',6'-octachloro-4,4'-di-(2-(2-hydroxyethoxy)-ethoxy)-biphenyl and 2,3,5,6,2',2',6'-octabromo-4,4'-di-(2-(2-hydroxyethoxy)-ethoxy)-biphenyl.
Claim 22
Dependent Claim
87 words
The adhesive according to claim 1 wherein component (a) is the esterification product of 0.275 moles tetrachlorophthalic anhydride, 0.9 moles phthalic anhydride, 1.26 moles ethylene glycol and 0.025 moles benzoic acid, component (b) is the polyester acrylate prepared by polycondensing 1 mole of a C 36 -dimer fatty acid with 2 moles of 1,6-hexane diol, followed by esterification with 2 moles of acrylic acid and components (c) and (d) are the mixed acrylate o-benzoylbenzoate ester of 1,6-hexanediol in admixture with the mixed acrylate beta-dimethylaminopropionate ester of 1,6-hexanediol.
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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) | 1982-01-15 | 1982-07-17 | 1983-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-15 | 1986-07-17 | 1987-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-15 | 1990-07-17 | 1991-01-16 | $7700.00 | Window Closed / Lapsed |