Patent US4846905A successfully refreshed from Google Patents.
US4846905A
Expired / Lapsed
US
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Acid catalyzed, toughened epoxy adhesives
Assignee: 3M Co
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Filing: 1988-04-06
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Granted: 1989-07-11
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Expires: 2008-04-06
Abstract
Abstract Disclosed is a thermally-curable, one-part epoxy adhesive composition comprising: (1) a glycidyl ether epoxide having a048477475 n epoxy functionality grater than one and a molecular weight between about 150 and 10,000; (2) a catalyst comprising (i) an acid of the formula H + SbF 5 X - wherein X is halogen, hydroxy, or --OR where --OR is the residue of an aliphatic or aromatic alcohol having a molecular weight less than about 10,000 and (ii) N,N-diethyl-o-toluidine; (3) an aliphatic or non-aromatic cyclic polyol having about 2 to 18 carbon atoms, at least two hydroxy groups of which are primary or secondary, and being free of electron-withdrawing substituents, amine substituents, or large substituents that cause steric hindrance in the α-position in relation to the carbon attached to the methylol group of the polyol; and (4) a toughening agent that does not react with the epoxide during curing and has an epoxide compatible component and an epoxide incompatible component.
Inventors
- 👤 Kent S. Tarbutton
- 👤 Janis Robins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:41
CPC Classifications
C; C09; C09J; C09J5/00; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/686; C08G59/40; C08G59/62; C08L; C08L63/00
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
155 words
A thermally-curable, one-part epoxy adhesive composition comprising: (1) a glycidyl ether epoxide having an epoxy functionality greater than one and a molecular weight between about 150 and 10,000; (2) a catalyst comprising (i) an acid of the formula H + SbF 5 X - wherein X is halogen, hydroxy, or --OR where --OR is the residue of an aliphatic or aromatic alcohol having a molecular weight less than about 10,000 and (ii) N,N- diethyl-o-toluidine; (3) an aliphatic or non-aromatic cyclic polyol having about 2 to 18 carbon atoms, at least two hydroxy groups of which are primary or secondary, and being free of electron-withdrawing substituents, amine substituents, or large substituents that cause steric hindrance in the α-position in relation to the carbon attached to the methylol group of the polyol; and (4) a toughening agent that does not react with the epoxide during curing and has an epoxide compatible component and an epoxide incompatible component.
Claim 2
Dependent Claim
155 words
A thermally-curable, one-part epoxy adhesive composition comprising: (1) a glycidyl ether epoxide having an epoxy functionality greater than one and a molecular weight between about 150 and 10,000; (2) a catalyst comprising (i) an acid of the formula H + SbF 5 X - wherein X is halogen, hydroxy, or --OR where --OR is the residue of an aliphatic or aromatic alcohol having a molecular weight less than about 10,000 and (ii) N,N- diethyl-o-toluidine; (3) an aliphatic or non-aromatic cyclic polyol having about 2 to 18 carbon atoms, at least two hydroxy groups of which are primary or secondary, and being free of electron-withdrawing substituents, amine substituents, or large substituents that cause steric hindrance in the α-position in relation to the carbon attached to the methylol group of the polyol; and (4) a toughening agent that does not react with the epoxide during curing and has an epoxide compatible component and an epoxide incompatible component.
Claim 3
Dependent Claim
26 words
The composition of claim 1 wherein the polyol is present in an amount sufficient to provide an hydroxy to epoxy ratio between about 0.5:1 and 1.1:1.
Claim 4
Dependent Claim
17 words
The composition of claim 2 wherein said hydroxy to epoxy ratio is between about 0.7:1 and 0.8:1.
Claim 5
Dependent Claim
20 words
The composition of claim 1 wherein the molar ratio of said acid to N,N-diethyl-o-toluidine is between about 1:1.5 and 1:10.
Claim 6
Dependent Claim
15 words
The composition of claim 4 wherein said molar ratio is between about 1:2 and 1:6.
Claim 7
Dependent Claim
22 words
The composition of claim 1 wherein said toughening agent is present at between about 3% and 35% by weight of the epoxide.
Claim 8
Dependent Claim
22 words
The composition of claim 1 wherein said toughening agent is a polymeric compound having both a rubbery phase and a thermoplastic phase.
Claim 9
Dependent Claim
41 words
The composition of claim 7 wherein said toughening agent is a graft polymer having a polymerized, diene, rubbery core and a shell grafted thereto of an acrylic acid ester, a methacrylic acid ester, a monovinyl aromatic hydrocarbon, or a mixture thereof.
Claim 10
Dependent Claim
20 words
The composition of claim 8 wherein said rubbery core comprises polymerized butadiene or a polymerized mixture of butadiene and styrene.
Claim 11
Dependent Claim
13 words
The composition of claim 9 wherein said shell comprises a methacrylic acid ester.
Claim 12
Dependent Claim
16 words
The composition of claim 10 wherein said methacrylic acid ester comprises a lower alkyl substituted methacrylate.
Claim 13
Dependent Claim
13 words
The composition of claim 9 wherein said shell comprises a monovinyl aromatic hydrocarbon.
Claim 14
Dependent Claim
21 words
The composition of claim 12 wherein said hydrocarbon is selected from styrene, alpha-methylstyrene, vinyltoluene, vinylxylene, ethylvinylbenzene, isopropylstyrene, chlorostyrene, dichlorostyrene, and ethylchlorostyrene.
Claim 15
Dependent Claim
51 words
The composition of claim 7 wherein said toughening agent is a core-shell polymer wherein the core is a rubbery polyacrylate polymer having a glass transition temperature below about 0° C. and the shell is grafted thereto and is a thermoplastic polyacrylate polymer having a glass transition temperature above about 25° C.
Claim 16
Dependent Claim
19 words
The composition of claim 14 wherein said core is selected from polybutylacrylate and polyisooctylacrylate and said shell is polymethylmethacrylate.
Claim 17
Dependent Claim
40 words
The composition of claim 7 wherein said toughening agent is an elastomeric particle having a T g below about 25° C. that is a polymerized mixture of free-radical polymerizable monomers and a polymeric stabilizer that is soluble in the epoxide.
Claim 18
Dependent Claim
14 words
The composition of claim 1 wherein X is the residue of an alkylene glycol.
Claim 19
Dependent Claim
9 words
The composition of claim 1 wherein X is 2-(2-hydroxyethoxy)ethoxy.
Claim 20
Dependent Claim
12 words
The composition of claim 1 wherein said polyol is an alkylene glycol.
Claim 21
Dependent Claim
10 words
The composition of claim 1 wherein said polyol is 1,4-cyclohexanedimethanol.
Claim 22
Dependent Claim
17 words
The composition of claim 1 wherein said epoxide has a molecular weight between about 300 and 1,000.
Claim 23
Dependent Claim
22 words
The composition of claim 1 wherein said epoxide is a diglycidyl ether of bisphenol A or a diglycidyl ether of bisphenol F.
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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) | 1992-07-10 | 1993-01-09 | 1993-07-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-07-10 | 1997-01-09 | 1997-07-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-07-10 | 2001-01-09 | 2001-07-11 | $7700.00 | Window Closed / Lapsed |