CA1176787A
Expired / Lapsed
CA
⏱️ 0.0 years remaining
Photosetting adhesive composition
Assignee: Deltaglass SA
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Filing: 1980-05-26
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Granted: 1984-10-23
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Expires: 2000-05-26
Abstract
Abstract ABSTRACT A photo-hardenable adhesive composition particularly suitable for use in the bonding of glass to other materials, especially plastics, as in the production of safety glass and armoured glass laminates and comprising (A) a photopolymerisable ester of an .alpha.,.beta. -ethylenically unsaturated acid and a hydroxylated urethane or urea and having a molecular weight of 500 to 10,00 (B) a photoinitiator (C) a substituted or unsubstituted aliphatic or cycloaliphatic N,N-dialkylamino alcohol ester of an .alpha.,.beta. -ethylenically unsaturated carboxylic acid, said alcohol having an alkylene moiety of up to six carbon atoms between hydroxy and the amino functions,and (D) an .alpha.,.beta. -ethylenically unsaturated carboxylic acid in an amount equal to one mole per mole of C, (C) and (D) being capable of reacting together to form a betaine, and preferably (E) at least one further copolymerisable monomer or oligomer and which may comprises an excess of (C) or (D) over equimolar.
Inventors
- 👤 Pierre Chevreux
- 👤 Van T. Nguyen
- 👤 Alain Roman
- 👤 Daniel Turpin
Bibliographic Details
Application Number
—
Jurisdiction
CA
Data Source
google_patents
Last Synchronized
2026-11-06 16:15
CPC Classifications
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Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
148 words
A.photohardenable composition polymerizable by irradiation under u.v. light to provide an adhesive and including: A) at least one olefinic photopolymerizable prepolymer having an olefinic double bond activated by an electrophilic substituent, and B) a polymerization photoinitiator, characterised in that the composition also includes C) a substituted or unsubstituted aliphatic or cycloaliphatic N,N-dialkylamino alcohol ester of an .alpha.,.beta.-ethylenically unsaturated carboxylic acid, said alcohol having an alkylene moiety of up to six carbon atoms between the hydroxy and the amino functions, and D) an .alpha.,.beta. -ethylenically unsaturated carboxylic acid in an amount equal to one mole per mole of C, (C) and (D) being capable of reacting together to form a betaine, and said oligomer or prepolymer A) is an ester of an .alpha.,.beta. -ethylenically unsaturated acid and a hydroxylated product containing urethane and/or urea links in the molecule thereof and having a molecular weight from about 500 to 10,000.
Claim 2
Dependent Claim
148 words
A.photohardenable composition polymerizable by irradiation under u.v. light to provide an adhesive and including: A) at least one olefinic photopolymerizable prepolymer having an olefinic double bond activated by an electrophilic substituent, and B) a polymerization photoinitiator, characterised in that the composition also includes C) a substituted or unsubstituted aliphatic or cycloaliphatic N,N-dialkylamino alcohol ester of an .alpha.,.beta.-ethylenically unsaturated carboxylic acid, said alcohol having an alkylene moiety of up to six carbon atoms between the hydroxy and the amino functions, and D) an .alpha.,.beta. -ethylenically unsaturated carboxylic acid in an amount equal to one mole per mole of C, (C) and (D) being capable of reacting together to form a betaine, and said oligomer or prepolymer A) is an ester of an .alpha.,.beta. -ethylenically unsaturated acid and a hydroxylated product containing urethane and/or urea links in the molecule thereof and having a molecular weight from about 500 to 10,000.
Claim 3
Dependent Claim
66 words
The composition of claim 1, characterised in that compounds (C) and (D) have the following formulae (I) (II) wherein the Q-Q link represents a straight or cyclic hydrocarbon connecting group of up to six carbon atoms, R1 to R3 represent H or lower alkyl groups, R4 and R5 are lower alkyls and R6 is H or a -COOR7 group where R7 is H or lower alkyl.
Claim 4
Dependent Claim
75 words
The composition of claim 1 characterised in that compound A has the structure of the product of reacting an isocyanate compound containing at least one isocyanate group and an ester of an .alpha.,.beta. -ethylenically unsaturated carboxylic acid the ester moiety of which has at least one active hydrogen atom, or is an ester of said acid and an oligomeric compound containing at least one free hydroxy group and at least one urethane or urea group.
Claim 5
Dependent Claim
134 words
The composition of claim 3, characterised in that the compound A has the structure of an ester of said acid and a hydroxylated product resulting from a condensation between an active hydrogen-containing compound selected from diols, polyols, and compounds containing at least one hydroxy group and one or more amino hydrogen atoms and an isocyanate compound selected from toluene diisocyanates, 4,4'-diphenyl diisocyanate, 4,4'-diphenyl alkane diisocyanates,dianisidine diisocyanates, 1,5-naphthalene diisocyanate, 4,4'-diphenyl ether diisocyanate, p-phenylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, ethylene diisocyanate, cyclohexylene diisocyanates, nonamethylene diisocyanate, octa-decamethylene diisocyanate, 2-chloropropane diisocyanate, 2,2'-diethyl-ether diisocyanate, 2'-(dimethylamino) pentane diisocyanate, tetrachlorophenylene-1,4-diisocyanate, 3-heptene diisocyanate and transvinylene diisocyanate and other polyisocyanates which are the higher molecular weight polyisocyanates obtained by reacting polyamines containing terminal primary or secondary amine groups, or polyhydric alcohols, with an excess of any of the above named diisocyanates.
Claim 6
Dependent Claim
37 words
The composition of claim 3 characterised in that component A is a substantially linear product derived from the .alpha.,.beta. -ethylenically unsaturated acid, at least one diol and at least one isocyanate having up to 2 isocyanate groups.
Claim 7
Dependent Claim
23 words
The composition of claim 5 characterised in that the diol is oligomeric and flexible and the isocyanate is a substantially rigid diisocyanate molecule.
Claim 8
Dependent Claim
19 words
The composition of claim 3, in which the acid is acrylic acid or an alpha-substituted derivative of acrylic acid.
Claim 9
Dependent Claim
27 words
The composition of claim 3 characterised in that component A has one olefinic unsaturation due to the acid per 800 to 3000 of molecular weight, in average.
Claim 10
Dependent Claim
19 words
The composition of claim 1 characterised in that it further includes at least one copolymerisable monomer or oligomer E.
Claim 11
Dependent Claim
28 words
The composition of claim 9 characterised in that component E is provided at least in part by an excess of component C or D over the equimolar amount.
Claim 12
Dependent Claim
31 words
The composition of claim 10 characterised in that component D is acrylic acid which is present in an excess of the equimolar amount so as to also contribute to component E.
Claim 13
Dependent Claim
36 words
The composition of claim 10 wherein component C is present in an amount up to 2 moles per mole of D or D is present in an amount up to 100 moles per mole of C.
Claim 14
Dependent Claim
26 words
The composition of claim 9 characterised in that the concentrations by weight of the ingred-ients are A 10-95%; B 0.001-10%; C plus D 1-10%, E 0.001-60%.
Claim 15
Dependent Claim
31 words
The composition of claim 13 character-ised in that compound E is selected from acrylic and methacrylic acid, the alkyl and cyanoalkyl esters thereof, the esters thereof with polyols and acrylic polyesters.
Claim 16
Dependent Claim
19 words
The composition of claim 1 character-ised in that compound C is dimethylaminoethyl methacrylate and compound D is acrylic acid.
Claim 17
Dependent Claim
34 words
A modification of the composition claimed in claim 1 wherein the equimolar amounts of components C and D are replaced by a betaine obtainable by reaction of a component C with a component D
Claim 18
Dependent Claim
60 words
A method of bonding a face of a material that is transparent to u.v. radiation to another face of the same or a different material, characterised in that a layer of the composition claimed in claim 1 is provided between the faces and the layer is then subjected to u.v. irradiation to cure the composition and bond the faces together.
Claim 19
Dependent Claim
19 words
A method as claimed in claim 17 characterised in that at least one of the faces is of glass.
Claim 20
Dependent Claim
21 words
A method as claimed in claim 18 characterised in that a glass face is laminated to a face of plastics material.
Claim 21
Dependent Claim
40 words
A method as claimed in claim 17 characterised in that a composite laminate is produced by bonding together two plates each of which is selected from organic glass plates and glass plates, said plates being bonded together by said composition.
Claim 22
Dependent Claim
23 words
A method as claimed in claim 20 characterised in that the organic glass is selected from polycarbonate, polyurethane, polymethacrylate and rigid polyvinyl chloride.
Claim 23
Dependent Claim
34 words
A method as claimed in claim 20 in which the laminate includes a thin flexible film of transparent plastics interposed between the plates, said film and plates all being bonded together by said composition.
Claim 24
Dependent Claim
30 words
A method as claimed in claim 22 characterised in that the thin flexible film of transparent plastic is made of a plastics selected from PVB, soft PVC and soft polyurethane.
Claim 25
Dependent Claim
18 words
A method as claimed in claim 18 in which glass is bonded to wood or a wood product.
Claim 26
Dependent Claim
14 words
A method as claimed in claim 18 in which glass is bonded to metal.
Claim 27
Dependent Claim
13 words
A method as claimed in claim 25 in which the metal is aluminium.
Claim 28
Dependent Claim
28 words
A laminate including two plates bonded together by u.v. irradiation of a composition claimed in claim 1, each plate being selected from organic glass plates and glass plates.
Claim 29
Dependent Claim
39 words
A laminate as claimed in claim 27 and further including a thin transparent flexible plastics film between the two plates, the plates and intermediate film all being bonded together by u.v. irradiation of a composition claimed in claim 1.
Claim 30
Dependent Claim
37 words
A laminate as claimed in claim 28 and including the structure ABC or ABCBA where each A is a glass plate, each B is a thin transparent flexible plastics film and C is an organic glass plate.
Claim 31
Dependent Claim
24 words
A laminate as claimed in claim 28 wherein said thin transparent flexible plastics film is selected from PVB, soft PVC and soft polyurethane film.
Claim 32
Dependent Claim
21 words
A laminate as claimed in claim 28 wherein said organic glass is selected from polycarbonate, polyurethane, polymethacrylate and rigid polyvinyl chloride.
Claim 33
Dependent Claim
21 words
A laminate as claimed in claim 27 wherein said organic glass is selected from polycarbonate, polyurethane, polymethacrylate and rigid polyvinyl chloride.
Claim 34
Dependent Claim
32 words
A double glazed unit wherein the bond between a glass sheet and a frame member is provided at least in part by u.v. irradiation of a composition as claimed in claim 1.
Claim 35
Dependent Claim
28 words
34 An article including a glass surface bonded to a surface of wood or a wood product by u.v. irradiation of a compositon as claimed in claim 1.
Claim 36
Dependent Claim
23 words
An article including a glass surface bonded to a surface of metal by u.v. irradiation of a composition as claimed in claim 1.
Claim 37
Dependent Claim
12 words
An article as claimed in claim 35 wherein the metal is aluminium.
References Cited (Backward Citations)
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