US4793886A
Expired / Lapsed
US
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Bonding method and adhesive useful for the method
Assignee: Cemedine Co Ltd
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Filing: 1987-07-02
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Granted: 1988-12-27
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Expires: 2007-07-02
Abstract
Abstract A method for bonding two objects by means of the following two adhesives: (A) a moisture-inducible room temperature anion polymerization curing adhesive composed essentially of at least one anion polymerizable compound selected from the group consisting of an alpha -cyanoacrylate compound, and a 1,1-disubstituted diene compound; and (B) a room temperature self-curing adhesive containing from 0.05 to 50% by weight of an anion polymerization accelerator, said self-curing adhesive being selected from the group consisting of (1) a room temperature moisture-curing adhesive, (2) a room temperature curing two-part type epoxy resin adhesive, and (3) a room temperature curing synthetic resin aqueous emulsion adhesive, which comprises applying said two adhesives (A) and (B) at the bonding interface of the objects so that they do not contact each other and pressing the objects to each other to bring the two adhesives in contact with each other.
Inventors
- 👤 Naomi Okamura
- 👤 Hiroshi Aoki
- 👤 Junzo Makino
- 👤 Hajime Yagi
- 👤 Yasuo Arai
- 👤 Takashi Yamanaka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:01
CPC Classifications
C; C09; C09J; C09J5/00; C09J5/04; C08; C08L; C08L35/00; C08L35/04; C08L83/00; C08L83/04; C09J2483/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31536
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
352 words
A method for bonding two objects by means of the following two adhesives: (A) a moisture-inducible room temperature anion polymerization curing adhesive consisting essentially of at least one anion polymerizable compound selected from the group consisting of an α-cyanoacrylate compound of the formula: ##STR6## wherein R is an alkyl group having from 1to 16 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms, a haloalkyl group having from 1 to 16 carbon atoms, a cyanoalkyl group having from 2 to 16 carbon atoms, an aralkyl group having from 6 to 12 carbon atoms, an acyloxyalkyl group having from 2 to 16 carbon atoms, a cycloalkyl group having from 3 to 16 carbon atoms, an alkenyl group having from 2 to 16 carbon atoms or an aryl group having from 6 to 12 carbon atoms, and a 1,1-disubstituted diene compound of the formula: ##STR7## wherein each of R 1 and R 2 which may be the same or different, is a hydrogen atom, an alkyl group having from 1 to 5 carbon atoms, an aryl group, an aralkyl group having from 6 to 12 carbon atoms or a halogen atom, R 3 is a hydrogen atom or a methyl group, each of X and Y which may be the same or different is a cyano group, a carboxylic acid ester group having from 2 to 12 carbon atoms, an ethylsulfone group, a phenylsulfone group, a formyl group, an acetyl group, a benzoyl group, an amide group, a diethyl sulfonyl group, or a phenyl group; and (B) a room temperature self-curing adhesive containing from 0.05 to 50% by weight of an anion polymerization accelerator, said self-curing adhesive being selected from the group consisting of (1) a room temperature moisture-curing adhesive, (2) a room temperature curing two-part type epoxy resin adhesive, and (3) a room temperature curing synthetic resin aqueous emulsion adhesive, which comprises applying said two adhesives (A) and (B) at the bonding interface of the objects so that they do not contact each other and pressing the objects to each other to bring the two adhesives in contact with each other.
Claim 2
Independent Claim
352 words
A method for bonding two objects by means of the following two adhesives: (A) a moisture-inducible room temperature anion polymerization curing adhesive consisting essentially of at least one anion polymerizable compound selected from the group consisting of an α-cyanoacrylate compound of the formula: ##STR6## wherein R is an alkyl group having from 1to 16 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms, a haloalkyl group having from 1 to 16 carbon atoms, a cyanoalkyl group having from 2 to 16 carbon atoms, an aralkyl group having from 6 to 12 carbon atoms, an acyloxyalkyl group having from 2 to 16 carbon atoms, a cycloalkyl group having from 3 to 16 carbon atoms, an alkenyl group having from 2 to 16 carbon atoms or an aryl group having from 6 to 12 carbon atoms, and a 1,1-disubstituted diene compound of the formula: ##STR7## wherein each of R 1 and R 2 which may be the same or different, is a hydrogen atom, an alkyl group having from 1 to 5 carbon atoms, an aryl group, an aralkyl group having from 6 to 12 carbon atoms or a halogen atom, R 3 is a hydrogen atom or a methyl group, each of X and Y which may be the same or different is a cyano group, a carboxylic acid ester group having from 2 to 12 carbon atoms, an ethylsulfone group, a phenylsulfone group, a formyl group, an acetyl group, a benzoyl group, an amide group, a diethyl sulfonyl group, or a phenyl group; and (B) a room temperature self-curing adhesive containing from 0.05 to 50% by weight of an anion polymerization accelerator, said self-curing adhesive being selected from the group consisting of (1) a room temperature moisture-curing adhesive, (2) a room temperature curing two-part type epoxy resin adhesive, and (3) a room temperature curing synthetic resin aqueous emulsion adhesive, which comprises applying said two adhesives (A) and (B) at the bonding interface of the objects so that they do not contact each other and pressing the objects to each other to bring the two adhesives in contact with each other.
Claim 3
Dependent Claim
43 words
The method according to claim 1, wherein the anion polymerization accelerator is at least one member selected from the group consisting of a tertiary amine compound, a lactone compound, a silacrown compoud, a crown compound, an N,N-dicyclohexylcarbodiimide, succinic acid amide, ethylenethiourea and 1,2,6-hexanetriol.
Claim 4
Dependent Claim
111 words
The method according to claim 1, wherein the anion polymerization accelerator is an aromatic tertiary amine compound of the formula: ##STR8## wherein each of R 4 and R 5 which may be the same or different, is an alkyl group having from 1 to 3 carbon atoms, X is an alkyl group having from 1 to 17 carbon atoms, a phenyl group, a cyclohexyl group, an amino group, a halogen atom, a hydroxy group or an alkoxy group having from 1 to 4 carbon atoms, and n is 0, 1, 2 or 3, provided that when n is 2 or 3, the plurality of X may be the same or different.
Claim 5
Dependent Claim
20 words
The method according to claim 1, wherein the anion polymerization accelerator is N,N-dimethyl-p-toluidine, N,N-diethyl-p-toluidine, N,N-dimethyl-m-toluidine, N,N-diethyl-m-toluidine, or a mixture thereof.
Claim 6
Dependent Claim
38 words
The method according to claim 1, wherein the room temperature anion polymerization curing adhesive consists essentially of at least one compound of the formula I wherein R is an alkyl group having from 1 to 16 carbon atoms.
Claim 7
Dependent Claim
27 words
The method according to claim 1, wherein the room temperature anion polymerization curing adhesive consists essentially of methyl α-cyanoacrylate, ethyl α-cyanoacrylate, propyl α-cyanoacrylate, or a mixture thereof.
Claim 8
Dependent Claim
50 words
The method according to claim 1, wherein the self-curing adhesive, is a room temperature moisture-curing adhesive consisting essentially of a polyisocyanate compound having in its molecule at least two isocyanate groups, or an organic silicon compound having in its molecule at least two-silicon atoms having a hydrolyzable group attached thereto.
Claim 9
Dependent Claim
38 words
The method according to claim 7, wherein the anion polymerization accelerator is at least one member selected from the group consisting of a tertiary amine compound, a lactone compound, a silacrown compound, an N,N-dicyclohexylcarbodiimide, succinic amide and ethylenethiourea.
Claim 10
Dependent Claim
32 words
The method according to claim 8, wherein the room temperature moisture-curing adhesive consists essentially of an isocyanate terminal polyurethane obtained by the reaction of an organic polyhydroxyl compound with an organic polyisocyanate.
Claim 11
Dependent Claim
117 words
The method according to claim 8, wherein the room temperature moisture-curing adhesive consist essentially of an organic silicon compound having in its molecule at least two reactive silicon functional groups of the formula: ##STR9## wherein Z is a hydrolyzable group selected from the group consisting of an acyloxy group, a ketoxime group, an alkoxy group, an alkenyloxy group, an amino group, an aminoxy group, and an amide group, R 4 is a non-hydrolyzable group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group and an iminoalkyl group, which groups are unsubstituted or substituted by halogen, an n is an integer of from 0 to 2.
Claim 12
Dependent Claim
24 words
The method according to claim 8, wherein the room temperature moisture-curing adhesive contains from 0.5 to 40% by weight of the anion polymerization accelerator.
Claim 13
Dependent Claim
76 words
The method according to claim 1, wherein the self-curing adhesive is a room temperature curing two-part type epoxy resin adhesive comprising an epoxy resin component composed essentially of an epoxy resin having in its molecule at least two epoxy groups, and an epoxy resin curing agent component, and the two-part type epoxy resin adhesive contains the anion polymerization accelerator in either one or both of the epoxy resin component and the epoxy resin curing agent component.
Claim 14
Dependent Claim
128 words
The method according to claim 12, wherein the anion polymerization accelerator is at least one member selected from the group consisting of an aromatic tertiary amine of the formula: ##STR10## wherein each of R 4 and R 5 which may be the same or different, is an alkyl group having from 1 to 3 carbon atoms, X is an alkyl group having from 1 to 17 carbon atoms, a phenyl group, a cyclohexyl group, an amino group, a halogen atom, a hydroxyl group or an alkoxy group having from 1 to 4 carbon atoms, n is 0, 1, 2 or 3, provided that when n is 2 or 3, the plurality of X may be the same or different, a lactone compound, 1,2,6-hexanetriol, N,N'-dicyclohexylcarbodiimide and succinic acid amide.
Claim 15
Dependent Claim
26 words
The method according to claim 13, wherein the epoxy resin is a polyhydric phenol glycidyl ether epoxy resin obtained by the reaction of 2,2-bis-(4-hydroxyphenyl)propane with epichlorohydrin.
Claim 16
Dependent Claim
25 words
The method according to claim 13, wherein the two-part type epoxy resin adhesive contains from 0.5 to 10% by weight of the anion polymerization accelerator.
Claim 17
Dependent Claim
38 words
The method according to claim 1, wherein the self-curing adhesive is a synthetic resin aqueous emulsion adhesive containing from 0.05 to 50% by weight of the anion-polymerization accelerator, based on the solid content of the aqueous emulsion adhesive.
Claim 18
Dependent Claim
39 words
The method according to claim 16, wherein the anion polymerization accelerator is at least one member selected from the group consisting of a tertiary amine compound, a lactone compound, a crown compound, N,N-dicyclohexylcarbodiimide, succinic acid amide, ethylenethiourea and 1,2,6-hexanetriol.
Claim 19
Dependent Claim
53 words
The method according to claim 17, wherein the aqueous emulsion adhesive is selected from the group consisting of a vinyl acetate resin emulsion, a styrene-butadiene copolymer emulsion, a carboxyl-modified styrene-butadiene copolymer emulsion, an acrylonitrile-butadiene copolymer emulsion, a carboxyl-modified acrylonitrile-butadiene copolymer emulsion, a styrene-alkyl methacrylate-alkyl acrylate copolymer emulsion and an ethylene-vinyl acetate copolymer emulsion.
Claim 20
Dependent Claim
33 words
The method according to claim 17, wherein the aqueous emulsion adhesive contains from 0.5 to 10% by weight of the anion polymerization accelerator, based on the solid content of the aqueous emulsion adhesive.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-12-27 | 1992-06-27 | 1992-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-27 | 1996-06-27 | 1996-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-27 | 2000-06-27 | 2000-12-27 | $7700.00 | Window Closed / Lapsed |