US4477636A
Expired / Lapsed
US
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Hot-melt adhesive and method
Assignee: Individual
•
Filing: 1982-06-28
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Granted: 1984-10-16
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Expires: 2002-06-28
Abstract
Abstract A hot-melt adhesive comprising a self-curing unsaturated polyester resin having an air-drying functional group and an average polymerization degree of 8 or more has been found to have an excellent heat resistance and a high bonding strength when it is bonding-cured under heat and pressure. If an additive selected from a polymerization initiator, a polymerization promotor and a photosensitizer is incorporated into the present air-drying, self-curing polyester resin, the curing speed is extremely increased to such an extent as cannot be expected from the conventional curing type adhesives. The incorporation of such an additive into the self-curing unsaturated polyester resin is advantageously realized in the form of composite structures of various forms, e.g., a laminate form, a core-in-sheath form and an islands-in-sea form. Such a composite hot-melt adhesive structure is useful for improving a pot life. If a thermoplastic polymer is incorporated, the resulting hot-melt adhesive is further improved with respect to bonding strength. Since the present hot-melt adhesive is solvent-free and does not contain as a cross-linking agent a vinyl monomer, it is easy to handle and environmental pollution can be advantageously avoided.
Inventors
- 👤 Soichi Muroi
- 👤 Shigetoshi Seta
- 👤 Yoshio Matsumoto
- 👤 Koichi Yasui
- 👤 Kazuyoshi Imamura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 21:15
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/66; C08G63/668; C08G63/676; C08G63/02; C08G63/12; C08G63/52; C08G63/68; C08G63/682; C08G63/6824; C08G63/6828; C09; C09J; C09J167/00; C09J167/06
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
69 words
A hot-melt adhesive comprising: a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from an α,β-unsaturated dicarboxylic acid; and a thermoplastic saturated polyester resin, said adhesive being capable of performing bonding-curing under heat and pressure, and wherein a vinyl monomer is not contained.
Claim 2
Dependent Claim
69 words
A hot-melt adhesive comprising: a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from an α,β-unsaturated dicarboxylic acid; and a thermoplastic saturated polyester resin, said adhesive being capable of performing bonding-curing under heat and pressure, and wherein a vinyl monomer is not contained.
Claim 3
Dependent Claim
37 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are present in the self-curing unsaturated polyester resin at a concentration of 0.001 or more equivalent/100 g of the hot-melt adhesive.
Claim 4
Dependent Claim
29 words
A hot-melt adhesive as claimed in claim 1, wherein said self-curing unsaturated polyester resin has a double bond concentration of 0.05 or more equivalent/100 g of the hot-melt adhesive.
Claim 5
Dependent Claim
23 words
A hot-melt adhesive as claimed in claim 1, wherein said self-curing unsaturated polyester resin has an average polymerization degree of 12 or more.
Claim 6
Dependent Claim
50 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from the group consisting of unsaturated aliphatic groups, saturated alicyclic groups, unsaturated alicyclic groups, saturated heterocyclic groups, unsaturated heterocyclic groups and groups having active methylene or active methine.
Claim 7
Dependent Claim
101 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from the group consisting of a pendant vinylidene group, a pendant vinyl group, a pendant allyl group, unsaturated aliphatic groups having 6 to 20 carbon atoms, groups having a norbornane ring, a tricyclodecane ring, a pentacyclopentadecane ring, a cyclopropene ring, a norbornene ring, a tricyclodecene ring, a pentacyclopentadecene ring, a cyclohexene ring, a tetrahydrofuran ring, a five-membered acetal ring or a furan ring, a benzyl ether group, an allyl ether group, a benzoylacetate group and a glycidyl ether residue.
Claim 8
Dependent Claim
40 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from the group consisting of a pendant vinylidene group, a pendant vinyl group and a pendant allyl group.
Claim 9
Dependent Claim
32 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from unsaturated aliphatic groups having 6 to 20 carbon atoms.
Claim 10
Dependent Claim
39 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from groups having a norbornane ring, a tricyclodecane ring or a pentacyclopentadecane ring and substituted groups thereof.
Claim 11
Dependent Claim
42 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from groups having a norbornene ring, a tricyclodecene ring, a pentacyclopentadecene ring or a cyclohexene ring and substituted groups thereof.
Claim 12
Dependent Claim
37 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from groups having a tetrahydrofuran ring or a five-membered acetal ring and substituted groups thereof.
Claim 13
Dependent Claim
32 words
A hot-melt adhesive as claimed in claim 1, wherein said one or more air-drying functional groups are one or more members selected from groups having a furan ring and substituted groups thereof.
Claim 14
Dependent Claim
51 words
A hot-melt adhesive as claimed in claim 5, wherein said groups having active methylene or active methine are one or more members selected from the group consisting of a benzyl ether group, an allyl ether group, a benzoylacetate group, a glycidyl ether residue and a 1,4-pentadienylene group, and substituted groups thereof.
Claim 15
Dependent Claim
30 words
A hot-melt adhesive as claimed in claim 1, wherein said self-curing unsaturated polyester resin has alcohol component residues comprising saturated straight-chain aliphatic glycol residues having 4 to 10 carbon atoms.
Claim 16
Dependent Claim
85 words
A hot-melt adhesive as claimed in claim 1, which further comprises at least one additive selected from the group consisting of a polymerization initiator selected from hydrogen peroxide, persulfates, dialkyl peroxides, diaralkyl peroxides, alkyl aralkyl peroxides, alkyl aryl peroxides, diacyl peroxides, ester peroxides, hydroperoxides, ketal peroxides, peroxycarbonates, metallic peroxide compounds, azo compounds, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3 and 1,1-bis(t-butylperoxy)cyclohexane; a polymerization promoter selected from metallic soaps, metal chelate compounds, amine compounds, phosphorus-containing compounds and sulfur-containing compounds; and a photosensitizer selected from peroxides, azo compounds, sulfides and benzoyl group-containing compounds.
Claim 17
Dependent Claim
25 words
A hot-melt adhesive as claimed in claim 15, wherein said polymerization initiator has a half-life of 1 minute or more as measured at 120° C.
Claim 18
Dependent Claim
21 words
A hot-melt adhesive as claimed in claim 15, wherein said polymerization promotor is at least one member selected from metallic soaps.
Claim 19
Dependent Claim
192 words
A hot melt-adhesive which comprises: a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from α,β-unsaturated dicarboxylic acid; and at least one additive selected from the group consisting of a polymerization initiator selected from hydrogen peroxide, persulfates, dialkyl peroxides, diaralkyl peroxides, alkyl aralkyl peroxides, alkyl aryl peroxides, diacyl peroxides, ester peroxides, hydroperoxides, ketal peroxides, peroxycarbonates, metallic peroxide compounds, azo compounds, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3 and 1,1-bis(t-butylperoxy)cyclohexane; a polymerization promoter selected from metallic soaps, metal chelate compounds, amine compounds, phosphorus-containing compounds and sulfur-containing compounds; and a photosensitizer selected from peroxides, azo compounds, sulfides and benzoyl group-containing compounds, and wherein said self-curing unsaturated polyester resin is present in the form of the resin itself or a composition containing the resin and said additive is present in the form of the additive itself or a composition containing the additive, said resin or said composition containing the resin being adapted to cooperate with said additive or said composition containing the additive to form a blend, and wherein a vinyl monomer is not contained.
Claim 20
Dependent Claim
192 words
A hot melt-adhesive which comprises: a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from α,β-unsaturated dicarboxylic acid; and at least one additive selected from the group consisting of a polymerization initiator selected from hydrogen peroxide, persulfates, dialkyl peroxides, diaralkyl peroxides, alkyl aralkyl peroxides, alkyl aryl peroxides, diacyl peroxides, ester peroxides, hydroperoxides, ketal peroxides, peroxycarbonates, metallic peroxide compounds, azo compounds, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3 and 1,1-bis(t-butylperoxy)cyclohexane; a polymerization promoter selected from metallic soaps, metal chelate compounds, amine compounds, phosphorus-containing compounds and sulfur-containing compounds; and a photosensitizer selected from peroxides, azo compounds, sulfides and benzoyl group-containing compounds, and wherein said self-curing unsaturated polyester resin is present in the form of the resin itself or a composition containing the resin and said additive is present in the form of the additive itself or a composition containing the additive, said resin or said composition containing the resin being adapted to cooperate with said additive or said composition containing the additive to form a blend, and wherein a vinyl monomer is not contained.
Claim 21
Dependent Claim
102 words
A hot-melt adhesive as claimed in claim 15, wherein (1) said self-curing unsaturated polyester resin is present in the form of the resin itself or a composition containing the resin and said resin or said composition containing the resin is a powder, a chip, a flake, a fiber, a rope, a film or a tape; and (2) said at least one additive is present in the form of the additive itself or a composition containing the additive and said additive or said composition containing the additive is a powder, a chip, a flake, a fiber, a rope, a film or a tape.
Claim 22
Dependent Claim
84 words
A hot melt adhesive as claimed in claim 15, wherein said self-curing unsaturated polyester resin is present in the form of the resin itself or a composition containing the resin and said additive is present in the form of the additive itself or a composition containing the additive and wherein said resin or said composition containing the resin and said additive or said composition containing the additive are in the form of a composite structure selected from a laminate, a core-in-sheath and an islands-in-sea.
Claim 23
Independent Claim
117 words
A method of bonding adherends, which comprises: applying, onto the surface of at least one of a plurality of adherends having their respective surfaces to be bonded, a hot melt adhesive comprising a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from an α,β-unsaturated dicarboxylic acid, said adhesive being capable of performing bonding-curing under heat and pressure; and effecting curing of the adhesive under heat and pressure while said plurality of adherends are mutually in association, through said adhesive, at their respective surfaces to be bonded, thereby to bond the adherends.
Claim 24
Independent Claim
117 words
A method of bonding adherends, which comprises: applying, onto the surface of at least one of a plurality of adherends having their respective surfaces to be bonded, a hot melt adhesive comprising a self-curing unsaturated polyester resin having a softening point of 45° to 200° C., one or more air-drying functional groups, an average polymerization degree of 8 or more and one or more double bonds originating from an α,β-unsaturated dicarboxylic acid, said adhesive being capable of performing bonding-curing under heat and pressure; and effecting curing of the adhesive under heat and pressure while said plurality of adherends are mutually in association, through said adhesive, at their respective surfaces to be bonded, thereby to bond the adherends.
Claim 25
Dependent Claim
31 words
A method according to claim 21, wherein said hot-melt adhesive further comprises at least one additive selected from the group consisting of a polymerization initiator, a polymerization promotor and a photosensitizer.
Claim 26
Dependent Claim
82 words
A method according to claim 22, wherein said self-curing unsaturated polyester resin is present in the form of the resin itself or a composition containing the resin and said at least one additive is present in the form of the additive itself or a composition containing the additive; and said curing of the adhesive is effected after the resin or the composition containing the resin is melt-blended with the additive or the composition containing the additive on the surface of the adherend.
Claim 27
Dependent Claim
42 words
A method according to claim 23, wherein the melt-blending is effected by the pressure applied, while heating, through the adherends to the resin or the composition containing the resin and the additive or the composition containing the additive which constitute the adhesive.
Claim 28
Dependent Claim
14 words
A method according to claim 21, wherein said heat is generated by high-frequency heating.
Claim 29
Dependent Claim
37 words
A hot-melt adhesive as claimed in claim 2 wherein said one or more air-drying functional groups are present in the self-curing unsaturated polyester resin at a concentration of 0.01 or more equivalent/100 g of the hot-melt adhesive.
Claim 30
Dependent Claim
30 words
A hot-melt adhesive as claimed in claim 3 wherein said self-curing unsaturated polyester resin contains double bonds at a concentration of 0.01 or more equivalent/100 g of the hot-melt adhesive.
Claim 31
Dependent Claim
22 words
A hot-melt adhesive as claimed in claim 1 wherein said thermoplastic saturated polyester has a softening point of 200° C. or less.
Claim 32
Dependent Claim
22 words
A hot-melt adhesive as claimed in claim 28 wherein said thermoplastic saturated polyester has a softening point of 120° C. or less.
Claim 33
Dependent Claim
28 words
A hot-melt adhesive as claimed in claim 18 wherein the amount of the polymerization initiator is 0.005 to 10% by weight, based on the self-curing unsaturated polyester resin.
Claim 34
Dependent Claim
28 words
A hot-melt adhesive as claimed in claim 18 wherein the amount of the polymerization promotor is 0.001 to 5% by weight based on the self-curing unsaturated polyester resin.
Claim 35
Dependent Claim
27 words
A hot-melt adhesive as claimed in claim 18 wherein the amount of the photosensitizer is 0.005 to 10% by weight based on the self-curing unsaturated polyester resin.
Claim 36
Dependent Claim
47 words
A hot-melt adhesive as claimed in claim 1 wherein said thermoplastic saturated polyester resin is selected from polyethylene terephthalate adipate, polybutylene terephthalate adipate, polyethylene terephthalate azelate, polybutylene terephthalate sebacate, polyhexamethylene terephthalate adipate, polybutylene terephthalate glutarate, polyneopentylene terephthalate dodecanedicarboxylate, polybutylene terephthalate isophthalate adipate and polybutylene terephthalate isophthalate azelate.
References Cited (Backward Citations)
CA596105A
Cited
US3271353A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-16 | 1988-04-16 | 1988-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-16 | 1992-04-16 | 1992-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-16 | 1996-04-16 | 1996-10-16 | $7700.00 | Window Closed / Lapsed |