US5017433A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Glass laminate and method of forming a glass laminate
Assignee: Deltaglass SA
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Filing: 1989-02-13
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Granted: 1991-05-21
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Expires: 2009-02-13
Abstract
Abstract A radiation-curable composition suitable for use as an adhesive for bonding glass, and in particular for the production of clear glass laminates, and of the kind comprising a urethane acrylate material in an αβ-ethylenically unsaturated diluent therefor, wherein the urethane acrylate material comprises a first component which is generally difunctional and a second component which has a functionality of at least about 3 and a molecular weight M N above 1200.
Inventors
- 👤 Pierre Chevreux
- 👤 Christiane A. R. Chevreux
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 05:28
CPC Classifications
C; C09; C09J; C09J4/00; B; B32; B32B; B32B17/00; B32B17/06; B32B17/10; B32B17/10005; B32B17/1055; B32B17/10706; B32B17/10743; C08; C08F; C08F299/00; C08F299/02; C08F299/06; C08F299/065; C08L; C08L75/00; C08L75/04; C09J175/00; C09J175/04; C09J175/14; C09J175/16; Y; Y10; Y10S; Y10S525/00; Y10S525/92; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31573; Y10T428/3158; Y10T428/31598; Y10T428/31601
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
456 words
A method of forming a laminate by bonding a glass sheet to a plastics foil by interposing a layer of a radiation-curable adhesive composition between said sheet and said foil and thereafter exposing the assembly of said sheet and said foil with said layer inbetween to irradiation to cure the adhesive and bond the sheet to the foil, wherein there is used as the adhesive composition a radiation-curable clear, homogeneous liquid adhesive composition consisting essentially of urethane acrylate in a liquid α,β-ethylenically unsaturated diluent and said urethane acrylate comprises (i) a first urethane acrylate component which is generally difunctional, at least a major proportion of which is material having a molecular weight (MN) in the range 1,5000 to 10,000 and which is obtainable by reaction of an oligomeric urethane intermediate having end groups selected from --OH and --NCO with an α,β-ethylenically unsaturated compound which has a group reactive with an end group of the intermediate and also a carboxy (--COOH) group attached to a carbon atom which is attached to a methylene group by a double bond and substantially all of the unsaturation in the urethane acrylate is terminal alpha-beta unsaturation, and (ii) an effective amount of a second urethane acrylate component which has a functionality of at least about 3 and a molecular weight (MN) above 1,200 and which is obtainable by reaction of an urethane intermediate having end groups selected from --OH an d--NCO with an α,β-ethylenically unsaturated compound which has a group reactive with an end group of the intermediate and also a carboxy (--COOH) group attached to a carbon atom which is attached to a methylene group by a double bond and substantially all of the unsaturation in the urethane acrylate is terminal alpha-beta unsaturation; the urethane intermediate of said urethane acrylate component is derived from polyisocyanate material selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the isocyanate groups are attached to aliphatic carbon atoms, and polyol selected from the group consisting of polyether polyols and polyol material a major proportion of which is polyether polyol; the urethane intermediate of said second urethane acrylate component is derived from polyisocyanate material selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the ioscyanate groups are attached to aliphatic carbon atoms, and polyol material selected from the group consisting of polyester polyols and polyol material a major proportion of which is polyester polyol; and component (i) is present in an amount of at least 80% by weight based on the combined weights of component (i) and component (ii).
Claim 2
Independent Claim
456 words
A method of forming a laminate by bonding a glass sheet to a plastics foil by interposing a layer of a radiation-curable adhesive composition between said sheet and said foil and thereafter exposing the assembly of said sheet and said foil with said layer inbetween to irradiation to cure the adhesive and bond the sheet to the foil, wherein there is used as the adhesive composition a radiation-curable clear, homogeneous liquid adhesive composition consisting essentially of urethane acrylate in a liquid α,β-ethylenically unsaturated diluent and said urethane acrylate comprises (i) a first urethane acrylate component which is generally difunctional, at least a major proportion of which is material having a molecular weight (MN) in the range 1,5000 to 10,000 and which is obtainable by reaction of an oligomeric urethane intermediate having end groups selected from --OH and --NCO with an α,β-ethylenically unsaturated compound which has a group reactive with an end group of the intermediate and also a carboxy (--COOH) group attached to a carbon atom which is attached to a methylene group by a double bond and substantially all of the unsaturation in the urethane acrylate is terminal alpha-beta unsaturation, and (ii) an effective amount of a second urethane acrylate component which has a functionality of at least about 3 and a molecular weight (MN) above 1,200 and which is obtainable by reaction of an urethane intermediate having end groups selected from --OH an d--NCO with an α,β-ethylenically unsaturated compound which has a group reactive with an end group of the intermediate and also a carboxy (--COOH) group attached to a carbon atom which is attached to a methylene group by a double bond and substantially all of the unsaturation in the urethane acrylate is terminal alpha-beta unsaturation; the urethane intermediate of said urethane acrylate component is derived from polyisocyanate material selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the isocyanate groups are attached to aliphatic carbon atoms, and polyol selected from the group consisting of polyether polyols and polyol material a major proportion of which is polyether polyol; the urethane intermediate of said second urethane acrylate component is derived from polyisocyanate material selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the ioscyanate groups are attached to aliphatic carbon atoms, and polyol material selected from the group consisting of polyester polyols and polyol material a major proportion of which is polyester polyol; and component (i) is present in an amount of at least 80% by weight based on the combined weights of component (i) and component (ii).
Claim 3
Dependent Claim
9 words
The laminate formed by the method of claim 1.
Claim 4
Dependent Claim
20 words
A method as claimed in claim 1 in which component (i) has a functionality of about 1.8 to about 2.2.
Claim 5
Dependent Claim
37 words
A method as claimed in claim 1 wherein the polyol is at least one oligomer selected from the group consisting of oligomers of ethylene oxide, oligomers of propylene oxide and oligomers of ethylene oxide and propylene oxide.
Claim 6
Dependent Claim
30 words
A method as claimed in claim 1 wherein the polyisocyanate from which component (i) is derived is selected from the group consisting of polymethylene diioscyanates, di(isocyanatocyclohexyl)cyclohexanes, isophorone diisocyanate and bis(isocyanatocyclohexyl)alkanes.
Claim 7
Dependent Claim
23 words
A method as claimed in claim 1 wherein component (i) has a molecular weight (MN) in the range about 2000 to about 8000.
Claim 8
Dependent Claim
24 words
A method as claimed in claim 1 wherein component (i) forms up to about 99% by weight of total urethane acrylate in the composition.
Claim 9
Dependent Claim
21 words
A method as claimed in claim 1 wherein the polyol material from which component (ii) is derived is derived from lactone.
Claim 10
Dependent Claim
13 words
A method as claimed in claim 8 in which the lactone comprises caprolactone.
Claim 11
Dependent Claim
22 words
A method as claimed in claim 1 wherein component (ii) forms at least about 0.5% by weight of the total urethane acrylate.
Claim 12
Dependent Claim
22 words
A method as claimed in claim 1 wherein component (ii) forms at least about 0.8% by weight of the total urethane acrylate.
Claim 13
Dependent Claim
24 words
A method as claimed in claim 1 wherein component (ii) forms from about 1% to about 15% by weight of the total urethane acrylate.
Claim 14
Dependent Claim
13 words
A method as claimed in claim 1 wherein the diluent includes acrylic acid.
Claim 15
Dependent Claim
21 words
A method as claimed in claim 1 wherein the diluent comprises acrylic acid and at least one monoester of acrylic acid.
Claim 16
Dependent Claim
29 words
A method as claimed in claim 14 wherein said at least one monoester is derived from an alkanol having from 1 to 6 carbon atoms and substituted derivatives thereof.
Claim 17
Dependent Claim
21 words
A method as claimed in claim 15 wherein said alkanol or substituted derivative thereof contains only carbon, oxygen and hydrogen atoms.
Claim 18
Dependent Claim
87 words
A method as claimed in claim 16 wherein said at least one monoester is derived from an alcohol having the structure: R--C(R').sub.2 --C(R').sub.2 --OH where R is --H, --OH or a monovalent organic group containing atoms selected only from carbon, oxygen and hydrogen, and having not more than 4 atoms in a chain attached to the free valency, and each R' is individually selected from --H and --CH 3 or R and an R' together form a divalent group containing atoms selected from carbon, oxygen and hydrogen.
Claim 19
Dependent Claim
16 words
A method as claimed in claim 14 wherein said at least one monoester is n-butyl acrylate.
Claim 20
Dependent Claim
27 words
A method as claimed in claim 14 wherein said at least one monoester forms up to 80% by weight of the mixture of monoester and acrylic acid.
Claim 21
Dependent Claim
37 words
A method as claimed in claim 14 wherein said at least one monoester is present in an amount of from about 10% to about 70% by weight, based on the combined weight of acrylic acid and monoester.
Claim 22
Dependent Claim
37 words
A method as claimed in claim 14 wherein said at least one monoester is present in an amount of from about 14% to about 35% by weight, based on the combined weight of acrylic aid and monoester.
Claim 23
Dependent Claim
17 words
A method as claimed in claim 1 which includes a photoinitiator and is curable by ultra-violet radiation.
Claim 24
Dependent Claim
39 words
A method as claimed in claim 1 in which the composition has a viscosity of about 300 to about 1200 cps as measured at 20° C. on a Brookfield LV viscometer with a No. 1 spindle at 6 r.p.m.
Claim 25
Dependent Claim
89 words
A method as claimed in claim 1 wherein the adhesive composition has a viscosity of 1200 cp or less, measured using a Brookfield LV viscometer with a No. 1 spindle of 6 r.p.m. at 20° C., and a cure time, as herein defined, of 30 seconds or less, and which cures to a clear and colourless adhesive layer having a bond strength of at least 500 g/cm, a water-resistance of at least 4 and a u.v.-resistance of 0, where bond strength, water-resistance and u.v.-resistance are all as define herein.
Claim 26
Dependent Claim
238 words
A method as claimed in claim 1 wherein component (i) as an oligomeric material having a functionality of about 1.8 to about 2.2 and a molecular weight (MN) in the range of about 3000 to about 7000 and is derived from (a) polyol selected from the group consisting of polyether polyols and polyol material and a major proportion of which is polyether polyol and is substantially free of ester groups and (b) polyisocyanate which is selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the isocyanate groups are attached to aliphatic carbon atoms, component (ii) is derived from caprolactone and polyisocyanate material which is selected from the group consisting of polyisocyanates in which the isocyanate groups are attached to aliphatic carbon atoms and polyisocyanate material in a major proportion of which the isocyanate groups are attached to aliphatic carbon atoms and forms from about 1% to about 15% by weight of the total urethane acrylate; and the diluent comprises acrylic acid and at least one monoester of acrylic acid which is present in an amount of about 14% to 35% by weight, based on the combined weight of acrylic acid and monoester; said composition also optionally including resinous material selected from epoxy resins and balsamic resins, in an amount which forms not more than 50% by weight of the composition.
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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) | 1994-05-20 | 1994-11-19 | 1995-05-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-05-20 | 1998-11-19 | 1999-05-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-05-20 | 2002-11-19 | 2003-05-21 | $7700.00 | Window Closed / Lapsed |