CA2004130A1 - High performance epoxy based laminating adhesive - Google Patents
High performance epoxy based laminating adhesiveInfo
- Publication number
- CA2004130A1 CA2004130A1 CA 2004130 CA2004130A CA2004130A1 CA 2004130 A1 CA2004130 A1 CA 2004130A1 CA 2004130 CA2004130 CA 2004130 CA 2004130 A CA2004130 A CA 2004130A CA 2004130 A1 CA2004130 A1 CA 2004130A1
- Authority
- CA
- Canada
- Prior art keywords
- component
- epoxy
- isocyanate
- polyester
- adhesive material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
Abstract
PATENT
ABSTRACT
A high performance laminating adhesive material is prepared using one or more epoxy components which inter-react with a high molecular weight polyester component through a two-stage reaction sequence. The first stage of the sequence is the reaction of a isocyanate component with a polyester component. The stage of the sequence is the reaction of the isocyanate/polyester component with the epoxy component(s). The result of the reaction process is an adhesive material providing a flexible, high temperature resistant, fully crosslinked adhesive with good Z-axis sta-bility without the evolution of by-products. The adhesive material has application to the bonding of polyimide films, copper or other metal foils and hardboards for use in the manufacture of flexible, hardboard or multilayer substrates as well as surface to surface bonding of other materials.
ABSTRACT
A high performance laminating adhesive material is prepared using one or more epoxy components which inter-react with a high molecular weight polyester component through a two-stage reaction sequence. The first stage of the sequence is the reaction of a isocyanate component with a polyester component. The stage of the sequence is the reaction of the isocyanate/polyester component with the epoxy component(s). The result of the reaction process is an adhesive material providing a flexible, high temperature resistant, fully crosslinked adhesive with good Z-axis sta-bility without the evolution of by-products. The adhesive material has application to the bonding of polyimide films, copper or other metal foils and hardboards for use in the manufacture of flexible, hardboard or multilayer substrates as well as surface to surface bonding of other materials.
Description
2~
PATENT
A HIGH PERFORMANCE EPOXY BASED LAMINATING ADHESIVE
by Thomas F. Gardeski and Diane G. Novak BACKGROUND
During the past quarter century, the growth of the electronic circuits industry at an unrivaled pace has resul-ted in the development of higher performance materials of construction. However, with the development of higher per-formance materials of construction has not resulted in thedevelopment of corresponding high performance adhesive materials and systems to bond the materials of construction together, especially in severe environmental conditions found in under-the-hood automotive and military applica-tions. Adhesive materials and systems that are currentlyavailable meet somP of the requirements for such properties as peel strength, chemical resistance, moisture resistance, high temperature stability, dimensional stability especially in the Z-axis direction and ease of processing, but typic-ally fail to meet one or more of the requirements for one ormore of the properties.
A need has therefore been felt for an adhesive material that meets all the requisite property requirements for severe environmental conditions while retaining the ease of application.
Z~ 3 SUMMARY
It is an object of the present invention to pro-vide an improved adhesive material.
It is a feature of the present invention to pro-vide an improved material suitable for US2 with electronicconstruction materials.
It is yet another feature of the present invention to provide an adhesive material that requires a two stage reaction process for bonding.
It is yet a further feature of the present inven-tion to combine an isocyanate component, a polyester compo-nent and one or more epoxy components using a two stage reaction to provid~ a high performance adhesive material.
The foregoing and other features are accomplished, according to the present invention, by combining at least one epoxy component chosen from the flexible bis-epi and the hard novolac epoxy families and at least one high moleculax weight polyester component along with an isocyanate cure mechanism. The isocyanate curing agent and the polyester component interact in a first reaction stage. The isocya-nate/polyester compound resulting from the first reaction stage and the epoxy components are combined. The resulting combination can be applied to a surface of a laminate layer or another first surface. A second surface can be placed in contact with the first sur~ace and a second reaction stage permitted to take p]ace, forming the high performance bond.
PATENT
A HIGH PERFORMANCE EPOXY BASED LAMINATING ADHESIVE
by Thomas F. Gardeski and Diane G. Novak BACKGROUND
During the past quarter century, the growth of the electronic circuits industry at an unrivaled pace has resul-ted in the development of higher performance materials of construction. However, with the development of higher per-formance materials of construction has not resulted in thedevelopment of corresponding high performance adhesive materials and systems to bond the materials of construction together, especially in severe environmental conditions found in under-the-hood automotive and military applica-tions. Adhesive materials and systems that are currentlyavailable meet somP of the requirements for such properties as peel strength, chemical resistance, moisture resistance, high temperature stability, dimensional stability especially in the Z-axis direction and ease of processing, but typic-ally fail to meet one or more of the requirements for one ormore of the properties.
A need has therefore been felt for an adhesive material that meets all the requisite property requirements for severe environmental conditions while retaining the ease of application.
Z~ 3 SUMMARY
It is an object of the present invention to pro-vide an improved adhesive material.
It is a feature of the present invention to pro-vide an improved material suitable for US2 with electronicconstruction materials.
It is yet another feature of the present invention to provide an adhesive material that requires a two stage reaction process for bonding.
It is yet a further feature of the present inven-tion to combine an isocyanate component, a polyester compo-nent and one or more epoxy components using a two stage reaction to provid~ a high performance adhesive material.
The foregoing and other features are accomplished, according to the present invention, by combining at least one epoxy component chosen from the flexible bis-epi and the hard novolac epoxy families and at least one high moleculax weight polyester component along with an isocyanate cure mechanism. The isocyanate curing agent and the polyester component interact in a first reaction stage. The isocya-nate/polyester compound resulting from the first reaction stage and the epoxy components are combined. The resulting combination can be applied to a surface of a laminate layer or another first surface. A second surface can be placed in contact with the first sur~ace and a second reaction stage permitted to take p]ace, forming the high performance bond.
3~
These and other features will be understood by the reading of the following description.
DESCRIPTION
The composition of materials of the present invention comprises at least one and preferably two epoxy components selected from the flexible bis-epi and hard novolac families, such as Celanese Epi-Rez-5132 and Dow D.E.N. 438 respectively; at least one high molecular weight polyester component such as DuPont's 49002 or DeSoto's 301 resin systems; and an isocyanate cure mechanism such as Upjohn's PAPI-135 or Mobay's Mondur MRS.
The cure sequence of the present invention consists of first reacting the isocyanate component with the hydroxyl groups which terminate the polyester component as shown in the following reaction sequence known in the related art.
HO~R)XOH + OCN-~C6H4 (CH2)]n N-C-O
1 R.T. to ~
P~
- o-~CH2) X- O-C-N--~C6~ -(CH2)~n H
where (R)x represents a high molecular weight polyester repeating unit with alcohol type hydroxyl end group func-tionality. This reaction takes place at room temperature 2~ 3~
These and other features will be understood by the reading of the following description.
DESCRIPTION
The composition of materials of the present invention comprises at least one and preferably two epoxy components selected from the flexible bis-epi and hard novolac families, such as Celanese Epi-Rez-5132 and Dow D.E.N. 438 respectively; at least one high molecular weight polyester component such as DuPont's 49002 or DeSoto's 301 resin systems; and an isocyanate cure mechanism such as Upjohn's PAPI-135 or Mobay's Mondur MRS.
The cure sequence of the present invention consists of first reacting the isocyanate component with the hydroxyl groups which terminate the polyester component as shown in the following reaction sequence known in the related art.
HO~R)XOH + OCN-~C6H4 (CH2)]n N-C-O
1 R.T. to ~
P~
- o-~CH2) X- O-C-N--~C6~ -(CH2)~n H
where (R)x represents a high molecular weight polyester repeating unit with alcohol type hydroxyl end group func-tionality. This reaction takes place at room temperature 2~ 3~
slowly and more rapidly with heating of the composition to approximately 250P. The secondary reaction, which is unique to the present invention, is comprised of reacting the - - group in the formed urethane linkage with the epoxide Cf~C groups of the epoxy components as follows:
- O-tR)X O-C-N-~C6H4 -(CE~2)~n + CH2 - CH - Rx - CH -~CH2 H ¦ ~(250-400~F) ~ O \ 0 o - 0-~CH2)x O-C ~ C~H4-(CH2)~n H - C - H
~Rx H - IC - O H
H - C - H
-0-~CH2)X O-C-N ---[CeH4 (CH2)]n where Rx in this formula represents the bis epi and/or novolac epoxy structures as shown below:
CH2-CH ~ CH2-~-0-0-C-0-OCH2-CH-CH23-n- -O-0-C-0-OC~ ~ CH-CH2 "BIS-EPI" EPOXY
CH2- CHCH2-O r ~~ ~O~
l OCH2--~H--CH2 O ~CH2-CH-~ CH2 ~ -CH2- - ~ CH2 , 0 2(:~0a~30 PATENT
"NOVOLAC"_EPOXY
Example of the Process The components of the adhesiv~ material of the present invention, according to one embodiment, are: a polyester resin having a solids content of 17-20~ composed of DuPont 49002 base in a solvent mixture of 90~ methylene chloride to 10% cyclohexanone by weight; an epoxy novolac at 85~ solids composed of Dow DEN 438-EK85 in methylethylke-tone; and a bis-epi epoxy composed of Celanese Epi-Rez 5132 at 100% solids; and a curative component of a polyfunctional isocyanate sold by Mobay under the trade name Mondur MRS.
The components can be combined according to the following two procedures:
Procedure l) The adhesive coating composition is made by adding 80% by solids of the polyester component to 10% by solids of the epoxy novolac to 10% by solids of the bis-epi epoxy to 1.2 parts by weight of the isocyanate in an open container without agitation. The composition is then agi-tated well for 1-5 minutes. The container is then capped with an air-tight lid for 30 minutes to allow for the onset of isocyanate/polyester reaction; or 3~) Procedure 2) The polyester and isocyanate are combined, thoroughly mixed, then allowed to stand at room temperature for a minimum of 30 minutes prior to the epoxy additions to allow onset of the isocyanate/hydroxyl reaction.
The adhesive coating composition resulting from either of the foregoing procedures is then applied by means of the reverse roll coating technique to a 1 mil polyimide film to yield a 1 mil thick dry coat weight. Drying (i.e., removal of the solvents) is accomplished through a 75 foot-3 zone oven at 212F and 25 feet per minute. The coated substrate is then positioned next to the treated side of 1 oz. copper foil, wherein the copper foil surface is treated with Oak CMC-lll compound (to enhance bondability).
The polyimide film and copper foil are heated to 300F to 325F with an applied pressure of 80 psi (pounds/square inch) to 120 psi through a coater/laminator combining station as part of a continuous operation. The resulting composite is rolled onto a 6" core, left at room temperature for one to seven days then post cured as follows:
2 hours @ 150F
2 hours @ 275F
2 hours @ 350F
The resulting composite structure exhibited the properties shown in Table I when tested per ANSI/IPC-FC-232B and 241 B
procedures:
Initial Peel 20 PLI
Peel After Solder 21 PLI
Chemical Resistance M~K 21 PLI
Tlll/MC 21 PLI
Solder Float Pass Aging (96 hrs @ 275F No Bond Strength in air circulating oven) Change where;
PLI = Pounds per lineal inch MEK = Methylethyl ketone TOL = Toluene IPA = Isopropylalcohol Tlll = Trichloroethylene MC = Methylene Chloride TABLE I
-~
The polyester compound of the preferred embodiment is a high molecular weight hydroxyl terminated polymer, while the curative compound is a polymeric isocyanate. In the preferred embodiment, a combination of a flexible bis-epi epoxy compound and a hard novolac epoxy compound are both included to achieve the properties of both compounds.
The second reaction provides a fully cross-linked network between the - - groups formed in the first reaction and the ~-~ in the epoxy components without evolution of by-products.
z~ o The present invention provides what is believed to be the first adhesive system with extremely balanced proper-ties and the added benefit of superior Z-axis stability through a unique and here-to-now undescribed cure mecha-nism. More specifically, the present invention provides thefirst epoxy based laminating adhesive which can be continu-ously processed and cured without the evolution of by-pro-ducts to provide a flexible bond-ply with overall properties superior to any currently available system with the added property of excellent Z-axis stability. The adhesive mater-ial is applicable to film substrates (e.g., polyimide), foil substrates (e.g., copper) and hardboard substrates (e.g., FR4 (fiberglass impregnated) hardboard).
The foregoing description is included to illustrate the operation of the preferred embodiment and is not meant to limit the scope of the invention. The scope of the invention is to be limited only by the following claims.
From the foregoing description, many variations will be apparent to those skilled in the art that would yet be encompassed by the spirit and scope of the invention.
- O-tR)X O-C-N-~C6H4 -(CE~2)~n + CH2 - CH - Rx - CH -~CH2 H ¦ ~(250-400~F) ~ O \ 0 o - 0-~CH2)x O-C ~ C~H4-(CH2)~n H - C - H
~Rx H - IC - O H
H - C - H
-0-~CH2)X O-C-N ---[CeH4 (CH2)]n where Rx in this formula represents the bis epi and/or novolac epoxy structures as shown below:
CH2-CH ~ CH2-~-0-0-C-0-OCH2-CH-CH23-n- -O-0-C-0-OC~ ~ CH-CH2 "BIS-EPI" EPOXY
CH2- CHCH2-O r ~~ ~O~
l OCH2--~H--CH2 O ~CH2-CH-~ CH2 ~ -CH2- - ~ CH2 , 0 2(:~0a~30 PATENT
"NOVOLAC"_EPOXY
Example of the Process The components of the adhesiv~ material of the present invention, according to one embodiment, are: a polyester resin having a solids content of 17-20~ composed of DuPont 49002 base in a solvent mixture of 90~ methylene chloride to 10% cyclohexanone by weight; an epoxy novolac at 85~ solids composed of Dow DEN 438-EK85 in methylethylke-tone; and a bis-epi epoxy composed of Celanese Epi-Rez 5132 at 100% solids; and a curative component of a polyfunctional isocyanate sold by Mobay under the trade name Mondur MRS.
The components can be combined according to the following two procedures:
Procedure l) The adhesive coating composition is made by adding 80% by solids of the polyester component to 10% by solids of the epoxy novolac to 10% by solids of the bis-epi epoxy to 1.2 parts by weight of the isocyanate in an open container without agitation. The composition is then agi-tated well for 1-5 minutes. The container is then capped with an air-tight lid for 30 minutes to allow for the onset of isocyanate/polyester reaction; or 3~) Procedure 2) The polyester and isocyanate are combined, thoroughly mixed, then allowed to stand at room temperature for a minimum of 30 minutes prior to the epoxy additions to allow onset of the isocyanate/hydroxyl reaction.
The adhesive coating composition resulting from either of the foregoing procedures is then applied by means of the reverse roll coating technique to a 1 mil polyimide film to yield a 1 mil thick dry coat weight. Drying (i.e., removal of the solvents) is accomplished through a 75 foot-3 zone oven at 212F and 25 feet per minute. The coated substrate is then positioned next to the treated side of 1 oz. copper foil, wherein the copper foil surface is treated with Oak CMC-lll compound (to enhance bondability).
The polyimide film and copper foil are heated to 300F to 325F with an applied pressure of 80 psi (pounds/square inch) to 120 psi through a coater/laminator combining station as part of a continuous operation. The resulting composite is rolled onto a 6" core, left at room temperature for one to seven days then post cured as follows:
2 hours @ 150F
2 hours @ 275F
2 hours @ 350F
The resulting composite structure exhibited the properties shown in Table I when tested per ANSI/IPC-FC-232B and 241 B
procedures:
Initial Peel 20 PLI
Peel After Solder 21 PLI
Chemical Resistance M~K 21 PLI
Tlll/MC 21 PLI
Solder Float Pass Aging (96 hrs @ 275F No Bond Strength in air circulating oven) Change where;
PLI = Pounds per lineal inch MEK = Methylethyl ketone TOL = Toluene IPA = Isopropylalcohol Tlll = Trichloroethylene MC = Methylene Chloride TABLE I
-~
The polyester compound of the preferred embodiment is a high molecular weight hydroxyl terminated polymer, while the curative compound is a polymeric isocyanate. In the preferred embodiment, a combination of a flexible bis-epi epoxy compound and a hard novolac epoxy compound are both included to achieve the properties of both compounds.
The second reaction provides a fully cross-linked network between the - - groups formed in the first reaction and the ~-~ in the epoxy components without evolution of by-products.
z~ o The present invention provides what is believed to be the first adhesive system with extremely balanced proper-ties and the added benefit of superior Z-axis stability through a unique and here-to-now undescribed cure mecha-nism. More specifically, the present invention provides thefirst epoxy based laminating adhesive which can be continu-ously processed and cured without the evolution of by-pro-ducts to provide a flexible bond-ply with overall properties superior to any currently available system with the added property of excellent Z-axis stability. The adhesive mater-ial is applicable to film substrates (e.g., polyimide), foil substrates (e.g., copper) and hardboard substrates (e.g., FR4 (fiberglass impregnated) hardboard).
The foregoing description is included to illustrate the operation of the preferred embodiment and is not meant to limit the scope of the invention. The scope of the invention is to be limited only by the following claims.
From the foregoing description, many variations will be apparent to those skilled in the art that would yet be encompassed by the spirit and scope of the invention.
Claims (17)
1. The process for providing an adhesive material which comprises:
reacting an isocyanate component with at least 1 polyester compound;
and reacting a isocyanate/polyester component resulting from said isocyanate/polyester reacting step with at least one epoxy component from the groups of bis epi and novolac epoxy components.
reacting an isocyanate component with at least 1 polyester compound;
and reacting a isocyanate/polyester component resulting from said isocyanate/polyester reacting step with at least one epoxy component from the groups of bis epi and novolac epoxy components.
2. The process for providing an adhesive material of Claim 1 further comprising:
mixing said isocyanate/polyester component with said epoxy compound and applying a resulting mixture to a location requiring said adhesive material prior to reaction between said isocyanate/polyester component and said at least one epoxy component.
mixing said isocyanate/polyester component with said epoxy compound and applying a resulting mixture to a location requiring said adhesive material prior to reaction between said isocyanate/polyester component and said at least one epoxy component.
3. The process for providing an adhesive material of Claim 2 further comprising:
applying said resulting mixture between substrates to bond said substrates, wherein said substrate are selected from the group including film substrates, foil substrates and hardboard substrates.
applying said resulting mixture between substrates to bond said substrates, wherein said substrate are selected from the group including film substrates, foil substrates and hardboard substrates.
4. The process for providing an adhesive material of Claim 1 further comprising;
using 50% - 90% by weight of the said polyester compound and 90% - 50% by weight of said at least one epoxy compound.
PATENT
using 50% - 90% by weight of the said polyester compound and 90% - 50% by weight of said at least one epoxy compound.
PATENT
5. The process for providing an adhesive material of Claim 1 further comprising:
selecting said polyester compound from the group of high molecular weight hydroxyl terminated polymer.
selecting said polyester compound from the group of high molecular weight hydroxyl terminated polymer.
6. The process for providing an adhesive material of Claim 1 wherein said reacting said epoxy component with said isocyanate/polyester component involves heating a mixture of said epoxy and said isocyanate/poly-ester components to a temperature between 250°F and 400°F.
7. An article having two surfaces bonded together in accordance with the process for providing an adhesive material of Claim 1.
8. A composite article with film to film bonding, foil to foil bonding or foil to film bonding having surfaces bonded together in accordance with the process of Claim 2.
9. The process of providing an adhesive material of Claim 1 wherein said isocyanate component, said polyester component and said epoxy component are mixed together prior to reacting of components.
10. An adhesive composite for application to surfaces to be bonded together prepared in accordance with Claim 2.
11. The process for providing an adhesive mater-ial of Claim 1 wherein said reacting said isocyanate/poly ester component with said at least one epoxy component includes reacting -?- group in the formed urethane linkage with the epoxide ?-c groups of the epoxy components.
12. A composite structure comprising:
at least a first and a second structure; and an adhesive material bonding a first surface of said first structure to a first surface of said second structure, said adhesive material including;
an isocyanate component, a polyester component, and at least one epoxy component chosen from the group of bis-epi epoxy family and the novolac epoxy family.
at least a first and a second structure; and an adhesive material bonding a first surface of said first structure to a first surface of said second structure, said adhesive material including;
an isocyanate component, a polyester component, and at least one epoxy component chosen from the group of bis-epi epoxy family and the novolac epoxy family.
13. The composite structure of Claim 12 wherein said first and said second structures are chosen from the group consisting of polyimide films, metal foils and hardboards.
14. The composite structure of Claim 13 wherein said polyester component is a high molecular weight hydroxyl terminated polymer, said polyester component and said isocyanate component having a reaction take place prior to a reaction involving said at least one epoxy component.
15. The composite structure of Claim 14 wherein a isocyanate/polyester component resulting from said reaction between said polyester component and said isocyanate and said at least one epoxy component are applied between said first structure first surface and said second structure second surface before a reaction between said isocya-nate/polyester component and said at least one epoxy component has taken place.
16. The composite structure of Claim 15 wherein said composite structure is heated to a temperature between 250°F and 400°F to permit a reaction between said isocya-nate/polyester component and said at least one epoxy com-ponent to take place.
17. The composite structure of Claim 16 wherein said reaction between said isocyanate/polyester component and said at least one epoxy component includes a reaction between isocyanate/polyester groups and epoxy groups.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2004130 CA2004130A1 (en) | 1989-11-29 | 1989-11-29 | High performance epoxy based laminating adhesive |
| JP1315132A JPH03182585A (en) | 1989-11-29 | 1989-12-04 | High performance laminating adhesive agent based on epoxy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2004130 CA2004130A1 (en) | 1989-11-29 | 1989-11-29 | High performance epoxy based laminating adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2004130A1 true CA2004130A1 (en) | 1991-05-29 |
Family
ID=4143657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2004130 Abandoned CA2004130A1 (en) | 1989-11-29 | 1989-11-29 | High performance epoxy based laminating adhesive |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH03182585A (en) |
| CA (1) | CA2004130A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0635035A1 (en) * | 1992-04-06 | 1995-01-25 | CPFILMS Inc. | A high performance epoxy based laminating adhesive |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6002065A (en) * | 1988-04-20 | 1999-12-14 | Norian Corporation | Kits for preparing calcium phosphate minerals |
-
1989
- 1989-11-29 CA CA 2004130 patent/CA2004130A1/en not_active Abandoned
- 1989-12-04 JP JP1315132A patent/JPH03182585A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0635035A1 (en) * | 1992-04-06 | 1995-01-25 | CPFILMS Inc. | A high performance epoxy based laminating adhesive |
| EP0635035A4 (en) * | 1992-04-06 | 1996-03-13 | Courtaulds Performance Films | A high performance epoxy based laminating adhesive. |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03182585A (en) | 1991-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |