US4604230A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Thermally stable adhesive
Assignee: Ingredion Inc
•
Filing: 1984-10-15
•
Granted: 1986-08-05
•
Expires: 2004-10-15
Abstract
Abstract A novel adhesive exhibiting low outgassing upon exposure to high temperature is disclosed. The instant adhesive comprises: (a) a soluble polyimide resin, (b) a solvent for said polyimide resin, (c) a tackifier, (d) an epoxy resin, (e) a hardener for said epoxy resin, (f) a catalyst which catalyzes the reaction between the epoxy and hardener, (g) a cross-linking agent reactive with the polyimide solvent of (b), (h) a catalyst which accelerates the reaction between (b) and (g), and (i) a filler material. Optionally, the adhesive may also contain a conductive material. A process for making the adhesive is also disclosed.
Inventors
- 👤 Jagadish C. Goswami
- 👤 Joseph A. Aurichio
- 👤 Joseph R. Zingaro
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:35
CPC Classifications
C; C09; C09J; C09J179/00; C08; C08F; C08F283/00; C08L; C08L79/00; C08L79/04; C08L79/08; C09J163/00
Claims Analysis
Total Claims: 99
Claim 1
Independent Claim
70 words
An adhesive composition comprising: (a) a soluble polyimide resin; (b) an appropriate solvent for said polyimide resin; (c) a tackifier; (d) an epoxy resin; (e) a hardener for said epoxy resin; (f) a catalyst which accelerates the curing of said epoxy resin; (g) a cross-linking agent reactive with the polyimide solvent of (b); (h) a catalyst which catalyzes the cross-linking reaction of (b) and (g); and (i) a filler material.
Claim 2
Dependent Claim
70 words
An adhesive composition comprising: (a) a soluble polyimide resin; (b) an appropriate solvent for said polyimide resin; (c) a tackifier; (d) an epoxy resin; (e) a hardener for said epoxy resin; (f) a catalyst which accelerates the curing of said epoxy resin; (g) a cross-linking agent reactive with the polyimide solvent of (b); (h) a catalyst which catalyzes the cross-linking reaction of (b) and (g); and (i) a filler material.
Claim 3
Dependent Claim
29 words
A composition according to claim 1 wherein the soluble polyimide resin is a polyimide resin derived from phenylindane diamines and dianhydrides, polyamide acid or a partially imidized polyamide acid.
Claim 4
Dependent Claim
24 words
A composition according to claim 1 wherein said soluble polyimide resin comprises from about 1.5% to about 21% by weight of the reaction mixture.
Claim 5
Dependent Claim
22 words
A composition according to claim 1 wherein the polyimide solvent is an ethylenically unsaturated organic compound having one or more unsaturated sites.
Claim 6
Dependent Claim
13 words
A composition according to claim 4 wherein said polyimide solvent is N-vinyl pyrrolidinone.
Claim 7
Dependent Claim
23 words
A composition according to claim 1 wherein said polyimide solvent comprises from about 15% to about 60% by weight of the adhesive composition.
Claim 8
Dependent Claim
17 words
A composition according to claim 1 wherein said tackifier is selected from the group of conventional tackifiers.
Claim 9
Dependent Claim
12 words
A composition according to claim 7 wherein said tackifier is polyvinyl pyrrolidinone.
Claim 10
Dependent Claim
22 words
A composition according to claim 1 wherein said tackifier comprises from about 0.3% to about 3% by weight of the adhesive composition.
Claim 11
Dependent Claim
18 words
A composition according to claim 1 wherein said epoxy resin is a glycidyl polyether of a polyhydric phenol.
Claim 12
Dependent Claim
18 words
A composition according to claim 1 wherein said epoxy resin is a glycidyl ether of a polyhydric alcohol.
Claim 13
Dependent Claim
18 words
A composition according to claim 1 wherein said epoxy resin is a glycidyl ester of a polycarboxylic acid.
Claim 14
Dependent Claim
18 words
A composition according to claim 1 wherein said epoxy resin is a glycidyl polyether of a polyhydric alchohol.
Claim 15
Dependent Claim
23 words
A composition according to claim 1 wherein said epoxy resin comprises from but 3% to abot 30% by weight of the adhesive composition.
Claim 16
Dependent Claim
27 words
A composition according to claim 1 wherein said hardener for said epoxy resin is an aliphatic amine having at least three active amine hydrogen atoms per molecule.
Claim 17
Dependent Claim
25 words
A composition according to claim 1 wherein said hardener for said epoxy resin is an amidoamine obtained by reacting a polyamine with a fatty acid.
Claim 18
Dependent Claim
23 words
A composition according to claim 1 wherein said hardener for said epoxy resin is selected from the group consisting of mercaptans and isocyanates.
Claim 19
Dependent Claim
18 words
A composition according to claim 1 wherein said hardener for said epoxy resin is an anhydride curing agent.
Claim 20
Dependent Claim
19 words
A composition according to claim 18 wherein said hardeners for said epoxy resin are methyl-bicyclo (2.2.1)heptane-2,3 dicarboxylic anhydride isomers.
Claim 21
Dependent Claim
17 words
A composition according to claim 1 wherein said hardener for said epoxy resin is an aromatic amine.
Claim 22
Dependent Claim
26 words
A composition according to claim 1 wherein said hardener for said epoxy resin comprises from about 3% to about 15% by weight of the adhesive composition.
Claim 23
Dependent Claim
24 words
A composition according to claim 1 wherein said catalyst accelerating the curing of said epoxy resin is an alkyl or aryl substituted imidazole catalyst.
Claim 24
Dependent Claim
13 words
A composition according to claim 22 wherein said catalyst is 2-ethyl, 2-methyl imidazole.
Claim 25
Dependent Claim
22 words
A composition according to claim 1 wherein said catalyst comprises from about 0.3% to about 3% by weight of the adhesive composition.
Claim 26
Dependent Claim
21 words
A composition according to claim 1 wherein said cross-linking agent reactive with the polyimide solvent is a polyethylenically unsaturated organic compound.
Claim 27
Dependent Claim
13 words
A composition according to claim 25 wherein said cross-linking agent is triallyl-S-triazine-2,4,6 trione.
Claim 28
Dependent Claim
23 words
A composition according to claim 2 wherein said cross-linking agent comprises from about 15% to about 60% by weight of the adhesive composition.
Claim 29
Dependent Claim
37 words
A composition according to claim 1 wherein said catalyst catalyzing the cross-linking reaction of (b) and (g) is an organic catalyst having a half life of the same order as the cure time at the temperature chosen.
Claim 30
Dependent Claim
14 words
A composition according to claim 28 wherein said organic catalyst is an organic peroxide.
Claim 31
Dependent Claim
14 words
A composition according to claim 29 wherein said organic peroxide is di-tertiary butyl peroxide.
Claim 32
Dependent Claim
13 words
A composition according to claim 28 wherein said organic catalyst is a peroxyketal.
Claim 33
Dependent Claim
14 words
A composition according to claim 29 wherein said organic catalyst is a t-amyl peroxide.
Claim 34
Dependent Claim
19 words
A composition according to claim 1 wherein said catalyst catalyzing the cross-linking reaction between (b) and (g) is 1,1'-azobis(cyclohexanecarbonitrile).
Claim 35
Dependent Claim
30 words
A composition according to claim 1 wherein said catalyst catalyzing the cross-linking reaction between (b) and (g) comprises from about 1.5% to abut 15% by weight of the adhesive composition.
Claim 36
Dependent Claim
15 words
A composition according to claim 1 wherein said filler material comprises glass or silica fillers.
Claim 37
Dependent Claim
11 words
A composition according to claim 35 wherein said filler is glass.
Claim 38
Dependent Claim
34 words
A composition according to claim 36 wherein said filler material comprises glass fillers of a size less than 10 microns and preferably of a melting point from about 350° C. to about 500° C.
Claim 39
Dependent Claim
11 words
A composition according to claim 35 wherein said filler is silica.
Claim 40
Dependent Claim
18 words
A composition according to claim 38 wherein said filler is silica of a size less than 1 micron.
Claim 41
Dependent Claim
23 words
A composition according to claim 1 wherein said filler material comprises from about 0.3% to about 15% by weight of the adhesive composition.
Claim 42
Dependent Claim
11 words
A composition according to claim 1, further comprising a conductive material.
Claim 43
Dependent Claim
14 words
A composition according to claim 41 wherein the conductive material is a noble metal.
Claim 44
Dependent Claim
12 words
A composition according to claim 42 wherein the noble metal is silver.
Claim 45
Dependent Claim
19 words
A composition according to claim 42 wherein the conductive material is a noble metal coated on a non-noble metal.
Claim 46
Dependent Claim
23 words
A composition according to claim 41 wherein the conductive material comprises from about 55% to about 70% by weight of the reaction mixture.
Claim 47
Dependent Claim
102 words
A process for the manufacture of an adhesive composition comprising: (a) mixing together the polyimide resin and the polyimide solvent, (b) adding the tackifier which imparts tackiness to the B-staged adhesive film, (c) mixing together the epoxy and curing agent for the epoxy and then adding this mixture to (b), (d) adding a catalyst dissolved in the polyimide solvent to mixture (c), (e) mixing together the second cross-linking agent and a catalyst which catalyzes the cross-linking reaction between the cross-linking agent and the polyimide solvent and adding this mixture to the mixture of (d), and (f) adding a suitable amount of filler.
Claim 48
Dependent Claim
102 words
A process for the manufacture of an adhesive composition comprising: (a) mixing together the polyimide resin and the polyimide solvent, (b) adding the tackifier which imparts tackiness to the B-staged adhesive film, (c) mixing together the epoxy and curing agent for the epoxy and then adding this mixture to (b), (d) adding a catalyst dissolved in the polyimide solvent to mixture (c), (e) mixing together the second cross-linking agent and a catalyst which catalyzes the cross-linking reaction between the cross-linking agent and the polyimide solvent and adding this mixture to the mixture of (d), and (f) adding a suitable amount of filler.
Claim 49
Dependent Claim
29 words
A process according to claim 46 wherein the soluble polyimide resin is a polyimide resin derived from phenylindane diamines and dianhydrides, polyamide acid or a partially imidized polyamide acid.
Claim 50
Dependent Claim
24 words
A process according to claim 46 wherein said soluble polyimide resin comprises from about 1.5% to about 21% by weight of the reaction mixture.
Claim 51
Dependent Claim
22 words
A process according to claim 46 wherein the polyimide solvent is an ethylenically unsaturated organic compound having one or more unsaturated sites.
Claim 52
Dependent Claim
23 words
A process according to claim 46 wherein said polyimide solvent comprises from about 15% to about 60% by weight of the adhesive composition.
Claim 53
Dependent Claim
17 words
A process according to claim 46 wherein said tackifier is selected from the group of conventional tackifiers.
Claim 54
Dependent Claim
22 words
A process according to claim 46 wherein said tackifier comprises from about 0.3% to about 3% by weight of the adhesive composition.
Claim 55
Dependent Claim
18 words
A process according to claim 46 wherein said epoxy resin is a glycidyl polyether of a polyhydric phenol.
Claim 56
Dependent Claim
18 words
A process according to claim 46 wherein said epoxy resin is a glycidyl ether of a polyhydric alcohol.
Claim 57
Dependent Claim
18 words
A process according to claim 46 wherein said epoxy resin is a glycidyl ester of a polycarboxylic acid.
Claim 58
Dependent Claim
18 words
A process according to claim 46 wherein said epoxy resin is a glycidyl polyether of a polyhydric alcohol.
Claim 59
Dependent Claim
23 words
A process according to claim 46 wherein said epoxy resin comprises from about 3% to about 30% by weight of the adhesive composition.
Claim 60
Dependent Claim
27 words
A process according to claim 46 wherein said hardener for said epoxy resin is an aliphatic amine having at least three active amine hydrogen atoms per molecule.
Claim 61
Dependent Claim
25 words
A process according to claim 46 wherein said hardener for said epoxy resin is an amidoamine obtained by reacting a polyamine with a fatty acid.
Claim 62
Dependent Claim
23 words
A process according to claim 46 wherein said hardener for said epoxy resin is selected from the group consisting of mercaptans and isocyanates.
Claim 63
Dependent Claim
18 words
A process according to claim 46 wherein said hardener for said epoxy resin is an anhydride curing agent.
Claim 64
Dependent Claim
17 words
A process according to claim 46 wherein said hardener for said epoxy resin is an aromatic amine.
Claim 65
Dependent Claim
26 words
A process according to claim 46 wherein said hardener for said epoxy resin comprises from about 3% to about 15% by weight of the adhesive composition.
Claim 66
Dependent Claim
24 words
A process according to claim 46 wherein said catalyst accelerating the curing of said epoxy resin is an alkyl or aryl substituted imidazole catalyst.
Claim 67
Dependent Claim
22 words
A process according to claim 46 wherein said catalyst comprises from about 0.3% to about 3% by weight of the adhesive composition.
Claim 68
Dependent Claim
21 words
A process according to claim 46 wherein said cross-linking agent reactive with the polyimide solvent is a polyethylenically unsaturated organic compound.
Claim 69
Dependent Claim
23 words
A process according to claim 46 wherein said cross-linking agent comprises from about 15% to about 60% by weight of the adhesive composition.
Claim 70
Dependent Claim
41 words
A process according to claim 46 wherein said catalyst catalyzing the cross-linking reaction between the polyimide solvent and the cross-linking agent is an organic catalyst having a half life of the same order as the cure time at the temperature chosen.
Claim 71
Dependent Claim
14 words
A process according to claim 68 wherein said organic catalyst is an organic peroxide.
Claim 72
Dependent Claim
13 words
A process according to claim 68 wherein said organic catalyst is a peroxyketal.
Claim 73
Dependent Claim
14 words
A process according to claim 68 wherein said organic catalyst is a t-amyl peroxide.
Claim 74
Dependent Claim
24 words
A process according to claim 46 wherein said catalyst catalyzing the cross-linking reaction between the polyimide solvent and the cross-linking agent is 1,1'-azobis (cyclohexanecarbonitrile).
Claim 75
Dependent Claim
34 words
A process according to claim 46 wherein said catalyst catalyzing the cross-linking reaction between the polyimide solvent and the cross-linking agent comprises from about 1.5% to about 15% by weight of the adhesive composition.
Claim 76
Dependent Claim
15 words
A process according to claim 46 wherein said filler material comprises glass or silica fillers.
Claim 77
Dependent Claim
11 words
A process according to claim 74 wherein said filler is glass.
Claim 78
Dependent Claim
34 words
A process according to claim 75 wherein said filler material comprises glass fillers of a size less than 10 microns and preferably of a melting point from about 350° C. to about 500° C.
Claim 79
Dependent Claim
11 words
A process according to claim 74 wherein said filler is silica.
Claim 80
Dependent Claim
18 words
A process according to claim 46 wherein said filler is silica of a size less than 1 micron.
Claim 81
Dependent Claim
23 words
A process according to claim 46 wherein said filler material comprises from about 0.3% to about 15% by weight of the adhesive composition.
Claim 82
Dependent Claim
14 words
A process according to claim 46, further comprising the addition of a conductive material.
Claim 83
Dependent Claim
14 words
A process according to claim 80 wherein the conductive material is a noble metal.
Claim 84
Dependent Claim
19 words
A process according to claim 80 wherein the conductive material is a noble metal coated on a non-noble metal.
Claim 85
Dependent Claim
23 words
A process according to claim 80 wherein the conductive material comprises from about 55% to about 70% by weight of the reaction mixture.
Claim 86
Dependent Claim
26 words
A process according to claim 46 further comprising curing the adhesive composition at about 90° C. to about 120° C. for a suitable period of time.
Claim 87
Dependent Claim
23 words
A process according to claim 84 comprising curing the adhesive composition at about 90° C. to about 120° C. for about 45 minutes.
Claim 88
Dependent Claim
27 words
A process according to claim 84 further comprising further curing the adhesive composition at about 200° C. to about 240° C. for a suitable period of time.
Claim 89
Dependent Claim
25 words
A process according to claim 86 further comprising further curing the adhesive composition at about 200° C. to about 240° C. for about 30 minutes.
Claim 90
Dependent Claim
26 words
A process according to claim 80 further comprising curing the adhesive composition at about 90° C. to about 120° C. for a suitable period of time.
Claim 91
Dependent Claim
23 words
A process according to claim 88 comprising curing the adhesive composition at about 90° C. to about 120° C. for about 45 minutes.
Claim 92
Dependent Claim
27 words
A process according to claim 88 further comprising further curing the adhesive composition at about 200° C. to about 240° C. for a suitable period of time.
Claim 93
Dependent Claim
25 words
A process according to claim 90 further comprising further curing the adhesive composition at about 200° C. to about 240° C. for about 30 minutes.
Claim 94
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 46.
Claim 95
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 80.
Claim 96
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 84.
Claim 97
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 86.
Claim 98
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 88.
Claim 99
Dependent Claim
11 words
The adhesive composition produced according to the process of claim 90.
References Cited (Backward Citations)
US2864774A
Cited
US3073784A
Cited
GB1258241A
Cited
GB1256531A
Cited
US3684533A
Cited
US3746662A
Cited
US4181643A
Cited
US4147669A
Cited
US4312793A
Cited
US4210704A
Cited
US4311615A
Cited
US4401767A
Cited
US4436785A
Cited
US4459166A
Cited
US4519941A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-08-04 | 1990-02-03 | 1990-08-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-04 | 1994-02-03 | 1994-08-05 | $3760.00 | Window Closed / Lapsed |
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