CA1109986A - Storage, rapidly hardening epoxy resin adhesive - Google Patents
Storage, rapidly hardening epoxy resin adhesiveInfo
- Publication number
- CA1109986A CA1109986A CA294,389A CA294389A CA1109986A CA 1109986 A CA1109986 A CA 1109986A CA 294389 A CA294389 A CA 294389A CA 1109986 A CA1109986 A CA 1109986A
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- weight
- powder
- ethylene
- acrylate
- 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.)
- Expired
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 31
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 31
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 28
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 28
- 239000000843 powder Substances 0.000 claims abstract description 47
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005977 Ethylene Substances 0.000 claims abstract description 12
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 11
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 6
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 6
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 3
- 229930003836 cresol Natural products 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- -1 poly-glycidyl compound Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000004848 polyfunctional curative Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920001890 Novodur Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- NFXQSLJCYPIFTE-UHFFFAOYSA-N ethane-1,2-diamine;phenol Chemical compound NCCN.OC1=CC=CC=C1.OC1=CC=CC=C1 NFXQSLJCYPIFTE-UHFFFAOYSA-N 0.000 description 1
- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000012205 single-component adhesive Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5093—Complexes of amines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacturing Of Multi-Layer Textile Fabrics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17277A CH606252A5 (en, 2012) | 1977-01-07 | 1977-01-07 | |
| CH172/77 | 1977-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109986A true CA1109986A (en) | 1981-09-29 |
Family
ID=4180898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,389A Expired CA1109986A (en) | 1977-01-07 | 1978-01-05 | Storage, rapidly hardening epoxy resin adhesive |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4117038A (en, 2012) |
| JP (1) | JPS5385831A (en, 2012) |
| AT (1) | AT355695B (en, 2012) |
| CA (1) | CA1109986A (en, 2012) |
| CH (1) | CH606252A5 (en, 2012) |
| DE (1) | DE2800302A1 (en, 2012) |
| FR (1) | FR2376891A1 (en, 2012) |
| GB (1) | GB1556988A (en, 2012) |
| SE (1) | SE7800150L (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4250293A (en) * | 1979-03-19 | 1981-02-10 | Air Products And Chemicals, Inc. | Latent amine salts of bis-phenol A |
| EP0074218B1 (en) * | 1981-08-26 | 1985-11-13 | Raychem Limited | Heat recoverable article |
| CA1217310A (en) * | 1981-09-14 | 1987-02-03 | George B. Park | Heat recoverable article |
| GB8403823D0 (en) * | 1984-02-14 | 1984-03-21 | Raychem Ltd | Adhesive composition |
| GB8622998D0 (en) * | 1986-09-24 | 1986-10-29 | Ciba Geigy Ag | Curable compositions |
| JPH07100766B2 (ja) * | 1987-06-25 | 1995-11-01 | ソマール株式会社 | エポキシ樹脂粉体塗料組成物 |
| DE59310074D1 (de) * | 1992-07-09 | 2000-08-17 | Ciba Sc Holding Ag | Härtbare Suspensionen auf Basis von Epoxidharzen |
| ES2127803T3 (es) * | 1992-08-11 | 1999-05-01 | Hexcel Corp | Resinas termoestables endurecidas con polimeros de sulfona. |
| US5824732A (en) * | 1993-07-07 | 1998-10-20 | Alliedsignal Inc. | Process for producing coating compositions containing ethylene-acrylic acid copolymers with polyamide grafts as rheology modifiers |
| ATE163188T1 (de) | 1993-07-07 | 1998-02-15 | Allied Signal Inc | Beschichtungszusammensetzungen die mit polyamidpropfpunkten versehen ethylen- acrylsäurekopolymeren enthalten als rheologieveränderungsmittel |
| DE19856254A1 (de) * | 1998-12-07 | 2000-06-08 | Freudenberg Carl Fa | Klebstoffpulver |
| US7566122B2 (en) * | 2004-04-15 | 2009-07-28 | Hewlett-Packard Development Company, L.P. | Fluid ejection device utilizing a one-part epoxy adhesive |
| WO2009074532A1 (en) * | 2007-12-10 | 2009-06-18 | Arkema France | Elastomeric flexibilizer for thermosets |
| JP7654552B2 (ja) * | 2019-09-27 | 2025-04-01 | 株式会社カネカ | 接着剤、および接着剤の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126214C (en, 2012) * | 1961-06-21 | 1900-01-01 | ||
| US3519576A (en) * | 1966-11-23 | 1970-07-07 | Minnesota Mining & Mfg | Latent curing epoxy compositions containing a crystalline polyphenate salt of a polyamine and 2,4,4-trimethyl-2,4,7-trihydroxyflavan |
| US3496250A (en) * | 1967-02-21 | 1970-02-17 | Borg Warner | Blends of epoxy resins and acrylonitrile butadiene-styrene graft copolymers |
| US3520905A (en) * | 1969-05-16 | 1970-07-21 | Minnesota Mining & Mfg | Flavan salt |
| BE793212A (fr) * | 1971-12-24 | 1973-06-22 | Ciba Geigy | Matieres durcissables a base de resines epoxydiques |
| DE2423843C3 (de) | 1974-05-16 | 1978-05-18 | Th. Goldschmidt Ag, 4300 Essen | Verfahren zur Herstellung eines härtbaren Klebfilms |
-
1977
- 1977-01-07 CH CH17277A patent/CH606252A5/xx not_active IP Right Cessation
- 1977-12-27 US US05/864,285 patent/US4117038A/en not_active Expired - Lifetime
-
1978
- 1978-01-04 DE DE19782800302 patent/DE2800302A1/de not_active Withdrawn
- 1978-01-04 GB GB149/78A patent/GB1556988A/en not_active Expired
- 1978-01-05 AT AT8978A patent/AT355695B/de not_active IP Right Cessation
- 1978-01-05 CA CA294,389A patent/CA1109986A/en not_active Expired
- 1978-01-05 SE SE7800150A patent/SE7800150L/xx unknown
- 1978-01-06 FR FR7800279A patent/FR2376891A1/fr active Granted
- 1978-01-06 JP JP48778A patent/JPS5385831A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1556988A (en) | 1979-12-05 |
| FR2376891B1 (en, 2012) | 1980-04-18 |
| FR2376891A1 (fr) | 1978-08-04 |
| SE7800150L (sv) | 1978-07-08 |
| ATA8978A (de) | 1979-08-15 |
| DE2800302A1 (de) | 1978-07-13 |
| CH606252A5 (en, 2012) | 1978-10-31 |
| AT355695B (de) | 1980-03-10 |
| US4117038A (en) | 1978-09-26 |
| JPS5385831A (en) | 1978-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1109986A (en) | Storage, rapidly hardening epoxy resin adhesive | |
| US3860541A (en) | Storage-stable, rapidly curable epoxide resin composition | |
| US5043102A (en) | Conductive adhesive useful for bonding a semiconductor die to a conductive support base | |
| US3496250A (en) | Blends of epoxy resins and acrylonitrile butadiene-styrene graft copolymers | |
| US3723223A (en) | Heat curing adhesive | |
| US4695598A (en) | Epoxy resin coating composition | |
| EP0754742B1 (en) | Room-temperature stable, one-component, flexible epoxy adhesives | |
| GB1568914A (en) | Storable rapidly hardening epoxy resin adhesive | |
| US4195140A (en) | Adhesive-promoting compositions | |
| KR0159537B1 (ko) | 분말 코팅 조성물의 제조방법 | |
| US6110993A (en) | Thermosetting epoxy resin composition | |
| RU2221699C2 (ru) | Ламинат из плоского пористого субстрата с покрытием и способ его изготовления | |
| EP0877769B1 (en) | Process for coating a heat-sensitive substrate by using a storage-stable moulding powder based on epoxy resins | |
| JPH02292325A (ja) | マイクロカプセル型アミン系硬化剤を用いたエポキシ樹脂組成物 | |
| JPH03281625A (ja) | 液状エポキシ樹脂組成物 | |
| JPS60248725A (ja) | エポキシ樹脂粉体組成物 | |
| KR960008474B1 (ko) | 열경화성 에폭시 수지를 기본으로 하는 분말 피복 조성물 | |
| Meath | Epoxy resin adhesives | |
| JPH01304150A (ja) | 金属粉含有エポキシ樹脂組成物 | |
| JPS5855970B2 (ja) | イチエキガタエポキシジユシ | |
| JPS61195114A (ja) | 一液性エポキシ樹脂組成物 | |
| JPS62240375A (ja) | 熱硬化性接着シ−ト | |
| KR100579793B1 (ko) | 건축용 프라이머 조성물 | |
| JPS63230780A (ja) | スロツト絶縁に好適なエポキシ樹脂粉体塗料 | |
| JPS594619A (ja) | エポキシ−ポリアミド樹脂組成物の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |