Patent US5143785A successfully refreshed from Google Patents.
US5143785A
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US
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Cyanate ester adhesives for electronic applications
Assignee: 3M Co
•
Filing: 1990-08-20
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Granted: 1992-09-01
•
Expires: 2010-08-20
Abstract
Abstract The present invention provides an adhesive composition that is useful as an energy-curable, one-part adhesive, suitable for bonding electronic components. The adhesive composition, preferably provided as an adhesive film, comprises the reaction product of an admixture of an effective amount of a curable cyanate ester resin, a thermoplastic polymer, and a curing catalyst. The catalyst may be, for example, thermally or photochemically activated.
Inventors
- 👤 Jean-Marc P. Pujol
- 👤 Joyce B. Hall
- 👤 Peter B. Hogerton
- 👤 Fred B. McCormick
- 👤 Jeanne M. Tingerthal
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:48
CPC Classifications
C; C09; C09J; C09J179/00; C09J179/04; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C08G73/0655; C09J7/00; C09J7/10; H; H05; H05K; H05K3/00; H05K3/30; H05K3/32; H05K3/321; Y; Y10; Y10T; Y10T428/00; Y10T428/28; Y10T428/2839; Y10T428/2852; Y10T428/2878; Y10T428/2896
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
80 words
An energy curable, one-part, adhesive composition adapted to be used in electronic applications, comprising the reaction product of an admixture of: a) an effective amount of a curable cyanate ester resin including one or more cyanate ester compounds; b) an effective amount of a thermoplastic polymer; and c) an effective amount of a catalyst comprising an organometallic compound, for the reaction of said cyanate ester compounds; wherein said adhesive composition is curable in 60 seconds or less at 180° C.
Claim 2
Dependent Claim
80 words
An energy curable, one-part, adhesive composition adapted to be used in electronic applications, comprising the reaction product of an admixture of: a) an effective amount of a curable cyanate ester resin including one or more cyanate ester compounds; b) an effective amount of a thermoplastic polymer; and c) an effective amount of a catalyst comprising an organometallic compound, for the reaction of said cyanate ester compounds; wherein said adhesive composition is curable in 60 seconds or less at 180° C.
Claim 3
Dependent Claim
21 words
The adhesive composition of claim 1 wherein said cyanate ester compounds have a cyanate equivalent weight of about 50 to 500.
Claim 4
Dependent Claim
21 words
The adhesive composition of claim 2 wherein said cyanate ester compounds have a cyanate equivalent weight of about 50 to 250.
Claim 5
Dependent Claim
20 words
The adhesive composition of claim 1 wherein said cyanate ester resin is present at about 25 to 95 weight percent.
Claim 6
Dependent Claim
20 words
The adhesive composition of claim 4 wherein said cyanate ester resin is present at about 40 to 90 weight percent.
Claim 7
Dependent Claim
20 words
The adhesive composition of claim 1 wherein said thermoplastic polymer is present at about 5 to 75 percent by weight.
Claim 8
Dependent Claim
20 words
The adhesive composition of claim 6 wherein said thermoplastic polymer is present at about 10 to 60 percent by weight.
Claim 9
Dependent Claim
27 words
The adhesive composition of claim 1 wherein said cyanate ester resin includes one or more cyanate ester compounds having a molecular weight of about 150 to 2000.
Claim 10
Dependent Claim
20 words
The adhesive composition of claim 8 wherein said cyanate ester compounds have a molecular weight of about 250 to 1200.
Claim 11
Dependent Claim
12 words
The adhesive composition of claim 1 further including a silane coupling agent.
Claim 12
Dependent Claim
21 words
The adhesive composition of claim 10 wherein said silane coupling agent is present at about 0.1 to 5 percent by weight.
Claim 13
Dependent Claim
21 words
The adhesive composition of claim 11 wherein said silane coupling agent is present at about 0.5 to 1.5 percent by weight.
Claim 14
Dependent Claim
62 words
The adhesive composition of claim 10 wherein said silane coupling agent has the following formula: P.sub.(4-n) SiZ.sub.n in which: P represents an organic substituent of up to 12 carbon atoms; e.g., propyl, which should possess functional substituents selected from the group consisting of mercapto, epoxy, glycidoxy, acrylyl, methacrylyl and amino; Z represents a hydrolyzable group; and n is 1, 2, or 3.
Claim 15
Dependent Claim
220 words
The adhesive composition of claim 1 wherein said cyanate ester resin includes one or more cyanate ester compositions having the following general formulas: Q(OCN).sub.p Formula I wherein p can be an integer from 2 to 7, and wherein Q comprises at least one of: (1) a mono-, di-, tri-, or tetrasubstituted aromatic hydrocarbon containing 5 to carbon atoms, and (2) 1 to 5 aliphatic or polycyclic aliphatic mono-, di-, tri-, or tetrasubstituted hydrocarbons containing 7 to 20 carbon atoms; ##STR7## wherein X is a single bond, a C 1 -C 4 alkylene group, --S--, or the --SO 2 -- group; and where R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently --H, a C 1 -C 5 alkyl group, or the Cyanate Ester Group: --OC.tbd.N with at least two of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 being the Cyanate Ester Group; ##STR8## where n is 0 to 5; or ##STR9## wherein R 7 , R 8 are independently wherein R 9 , R 10 , and R 11 are independently --H, a C 1 -C 5 alkyl group, or the Cyanate Ester Group, where R 7 , R 8 combined include two or more Cyanate Ester Groups.
Claim 16
Dependent Claim
36 words
The adhesive composition of claim 14 wherein said cyanate ester compounds according to Formula I contain 1 to 10 heteroatoms selected from the group consisting of non-peroxidic oxygen, sulfur, non-phosphino phosphorus, non-amino nitrogen, halogen, and silicon.
Claim 17
Dependent Claim
22 words
The adhesive composition of claim 14 wherein said cyanate ester resin includes one or more cyanate ester compounds according to Formula II.
Claim 18
Dependent Claim
35 words
The adhesive composition of claim 16 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are --H, --CH 3 , or the Cyanate Ester Group.
Claim 19
Dependent Claim
26 words
The adhesive composition of claim 14 wherein R 9 , R 10 , and R 11 are --H, --CH 3 , or the Cyanate Ester Group.
Claim 20
Dependent Claim
19 words
The adhesive composition of claim 1 wherein said thermoplastic polymer has a molecular weight of about 3,000 to 200,000.
Claim 21
Dependent Claim
32 words
The adhesive composition of claim 19 wherein said thermoplastic polymer is selected from the group consisting of: polysulfones, polyvinyl acetals, polyamides, polyesters, polyimides, polycarbonates, polyethers, polyimidesiloxanes, polycarbonatesiloxanes, polyetherimides, polyvinylics, and phenoxy resins.
Claim 22
Dependent Claim
27 words
The adhesive composition of claim 19 wherein said thermoplastic polymer has the following formula: ##STR10## wherein m is 0 or 1, and n is 10 to 500.
Claim 23
Dependent Claim
17 words
The adhesive composition of claim 21 wherein m is 0 and n is about 12 to 50.
Claim 24
Dependent Claim
17 words
The adhesive composition of claim 21 wherein m is 1 and n is about 40 to 70.
Claim 25
Dependent Claim
44 words
The adhesive composition of claim 19 wherein said thermoplastic polymer has the following formula: ##STR11## wherein X is --H or a C 1 -C 4 alkyl group, and m is 80 to 2400, n is 10 to 2200, and p is 0 to 500.
Claim 26
Dependent Claim
28 words
The adhesive composition cf claim 24 wherein m is greater than n, n is greater than p, m is less than 800, and the monomers are randomly distributed.
Claim 27
Dependent Claim
22 words
The adhesive composition of claim 19 wherein said thermoplastic polymer has the following formula: ##STR12## wherein n is about 75 to 150.
Claim 28
Dependent Claim
25 words
The adhesive composition of claim 1 further including at least one additive selected from the group consisting of catalysts, conductive particles, coupling agents, and filler.
Claim 29
Dependent Claim
17 words
The adhesive composition of claim 1 wherein said catalyst is an organometallic compound containing a cyclopentadienyl group.
Claim 30
Dependent Claim
12 words
The adhesive composition of claim 1 wherein said catalyst is thermally activated.
Claim 31
Dependent Claim
12 words
The adhesive composition of claim 1 wherein said catalyst is photochemically activated.
Claim 32
Dependent Claim
19 words
The adhesive composition of claim 1 further including about 0.1 to 10 percent by weight of a monofunctional cyanate.
Claim 33
Dependent Claim
22 words
The adhesive composition of claim 31 wherein said monofunctional cyanate is a cyanate ester according to Formula I wherein p is 1.
Claim 34
Dependent Claim
26 words
The adhesive composition of claim 32 wherein said monofunctional cyanate is present at a concentration of about 1 to 20 percent of the cyanate ester resin.
Claim 35
Dependent Claim
14 words
The adhesive composition of claim 1 provided as a storage-stable, substantially tack-free adhesive film.
Claim 36
Dependent Claim
13 words
The adhesive composition of claim 34 wherein said adhesive film is anisotropically conductive.
Claim 37
Dependent Claim
15 words
The adhesive composition of claim 35 wherein said adhesive film contains randomly dispersed conductive particles.
Claim 38
Dependent Claim
19 words
The adhesive composition of claim 35 wherein said conductive particles are arranged in a uniform array of predetermined configuration.
Claim 39
Dependent Claim
21 words
The adhesive composition of claim 1 having an extractable ion content of less than about 10 parts per million by weight.
Claim 40
Dependent Claim
10 words
An adhesive film comprising the adhesive composition of claim 1.
Claim 41
Dependent Claim
11 words
The adhesive film of claim 39 further including a release liner.
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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) | 1995-09-01 | 1996-03-02 | 1996-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-09-01 | 2000-03-02 | 2000-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-09-01 | 2004-03-02 | 2004-09-01 | $7700.00 | Window Closed / Lapsed |