CA2314924C - Method to achieve improved adhesion of urethane adhesive to a painted surface - Google Patents
Method to achieve improved adhesion of urethane adhesive to a painted surface Download PDFInfo
- Publication number
- CA2314924C CA2314924C CA002314924A CA2314924A CA2314924C CA 2314924 C CA2314924 C CA 2314924C CA 002314924 A CA002314924 A CA 002314924A CA 2314924 A CA2314924 A CA 2314924A CA 2314924 C CA2314924 C CA 2314924C
- Authority
- CA
- Canada
- Prior art keywords
- percent
- acid
- weight
- solvent
- composition
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000000853 adhesive Substances 0.000 title claims abstract description 22
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000011521 glass Substances 0.000 claims abstract description 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 4
- -1 alkyl aromatic compound Chemical class 0.000 claims abstract description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 claims description 3
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000758 substrate Substances 0.000 description 16
- 239000004591 urethane sealant Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 6
- 239000000565 sealant Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002987 primer (paints) Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 230000037452 priming Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RAADJDWNEAXLBL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene Chemical compound C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 RAADJDWNEAXLBL-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
- B05D3/101—Pretreatment of polymeric substrate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/10—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an adhesive surface
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
- C03C17/322—Polyurethanes or polyisocyanates
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
- C03C17/3405—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions with at least two coatings of organic materials
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
- C03C27/04—Joining glass to metal by means of an interlayer
- C03C27/048—Joining glass to metal by means of an interlayer consisting of an adhesive specially adapted for that purpose
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/14—Glass
- C09J2400/146—Glass in the pretreated surface to be joined
-
- 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
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/16—Metal
- C09J2400/166—Metal in the pretreated surface to be joined
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Ceramic Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Sealing Material Composition (AREA)
- Joining Of Glass To Other Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6803897P | 1997-12-18 | 1997-12-18 | |
| US60/068,038 | 1997-12-18 | ||
| PCT/US1998/027143 WO1999031191A1 (en) | 1997-12-18 | 1998-12-18 | Method to achieve improved adhesion of urethane adhesive to a painted surface |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2314924A1 CA2314924A1 (en) | 1999-06-24 |
| CA2314924C true CA2314924C (en) | 2008-01-22 |
Family
ID=22080038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002314924A Expired - Fee Related CA2314924C (en) | 1997-12-18 | 1998-12-18 | Method to achieve improved adhesion of urethane adhesive to a painted surface |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6053971A (enExample) |
| EP (1) | EP1042419B2 (enExample) |
| JP (3) | JP2002508431A (enExample) |
| KR (1) | KR100590437B1 (enExample) |
| CN (1) | CN1117128C (enExample) |
| AT (1) | ATE273357T1 (enExample) |
| AU (1) | AU741998B2 (enExample) |
| BR (1) | BR9815177B1 (enExample) |
| CA (1) | CA2314924C (enExample) |
| DE (1) | DE69825627T3 (enExample) |
| ES (1) | ES2223145T5 (enExample) |
| WO (1) | WO1999031191A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7294400B2 (en) * | 2003-03-17 | 2007-11-13 | Hewlett-Packard Development Company, L.P. | Flexible barrier film structure |
| WO2005089480A2 (en) | 2004-03-19 | 2005-09-29 | Stuart Arthur Bateman | Activation method |
| US20060079661A1 (en) * | 2004-10-08 | 2006-04-13 | Zhu Huide D | Low volatile isocyanate monomer containing polyurethane prepolymer and adhesive system |
| CA2589526C (en) | 2005-01-21 | 2014-12-02 | Commonwealth Scientific And Industrial Research Organisation | Activation method using modifying agent |
| US7781493B2 (en) * | 2005-06-20 | 2010-08-24 | Dow Global Technologies Inc. | Protective coating for window glass |
| EP1760129A1 (de) * | 2005-09-02 | 2007-03-07 | Sika Technology AG | Wässrige Haftreinigerzusammensetzung zur Erhöhung der Haftung von Klebstoffen und Dichtstoffen auf Lacken |
| CA2673346C (en) | 2006-12-19 | 2014-12-02 | Dow Global Technologies Inc. | Adhesion promotion additives and methods for improving coating compositions |
| US7955696B2 (en) | 2006-12-19 | 2011-06-07 | Dow Global Technologies Llc | Composites and methods for conductive transparent substrates |
| JP5512529B2 (ja) * | 2007-11-07 | 2014-06-04 | ダウ グローバル テクノロジーズ エルエルシー | 充填剤レベルの高いポリウレタン接着剤組成物 |
| BRPI0913143A2 (pt) * | 2008-09-10 | 2016-01-05 | Dow Global Technologies Llc | sistema e método de ligação de um adesivo reativo à pelo menos um substrato |
| JP5594004B2 (ja) * | 2010-09-14 | 2014-09-24 | 横浜ゴム株式会社 | ガラスの接着方法 |
| KR101724180B1 (ko) | 2011-02-17 | 2017-04-06 | 다우 글로벌 테크놀로지스 엘엘씨 | 탄산 칼슘을 함유하는 알콕시실란 함유 폴리우레탄 접착제 조성물 |
| JP5805854B2 (ja) | 2011-05-03 | 2015-11-10 | ダウ グローバル テクノロジーズ エルエルシー | ガラスに対する接合のために有用なデュアルキュア接着剤 |
| KR20130143661A (ko) | 2011-05-03 | 2013-12-31 | 다우 글로벌 테크놀로지스 엘엘씨 | 아이소시아네이트 작용성 예비중합체를 함유하는 촉진된 경화 조성물 |
| US9694565B2 (en) | 2012-10-08 | 2017-07-04 | Dow Global Technologies Llc | Accelerated bonding of isocyanate functional adhesive to fiber reinforced plastics |
| US9416301B2 (en) | 2012-11-08 | 2016-08-16 | Dow Global Technologies Llc | Ultrafast dual cure adhesive useful for bonding to glass |
| CN104877812A (zh) * | 2015-04-10 | 2015-09-02 | 济南汉斯曼时代技术有限公司 | 一种聚氨酯胶粘剂配套专用清洗活化剂 |
| KR102691177B1 (ko) | 2018-01-25 | 2024-08-01 | 메르크 파텐트 게엠베하 | 포토레지스트 리무버 조성물 |
| US11994803B2 (en) | 2019-07-11 | 2024-05-28 | Merck Patent Gmbh | Photoresist remover compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239549A (en) * | 1976-07-16 | 1980-12-16 | Basf Aktiengesellschaft | Easily water-dispersed formulations of finely divided phthalocyanines |
| US4758648A (en) * | 1986-10-20 | 1988-07-19 | Essex Specialty Products, Inc. | High speed cure sealant |
| US4857366A (en) * | 1988-03-11 | 1989-08-15 | Minnesota Mining And Manufacturing Company | Method for obtaining adhesion of urethane sealant to a painted or glass surface |
| US5063269A (en) * | 1990-01-16 | 1991-11-05 | Essex Specialty Products, Inc. | One-part primerless adhesive |
| DE4022484C1 (enExample) * | 1990-07-17 | 1991-07-11 | Gurit-Essex Ag, Freienbach, Ch | |
| JP2962620B2 (ja) * | 1992-08-05 | 1999-10-12 | 三井化学株式会社 | 金属接着性プライマー組成物 |
| US5238993A (en) * | 1992-10-02 | 1993-08-24 | The Dow Chemical Company | Primer composition for improving the bonding of urethane adhesives to acid resistant paints |
| CA2144530C (en) * | 1992-10-13 | 2005-07-26 | Wen Bin Chiao | Polyurethane sealant compositions |
| JP3938414B2 (ja) * | 1996-06-13 | 2007-06-27 | 横浜ゴム株式会社 | 電着型材用プライマー組成物 |
-
1998
- 1998-12-18 JP JP2000539100A patent/JP2002508431A/ja not_active Withdrawn
- 1998-12-18 CA CA002314924A patent/CA2314924C/en not_active Expired - Fee Related
- 1998-12-18 EP EP98964166A patent/EP1042419B2/en not_active Expired - Lifetime
- 1998-12-18 AT AT98964166T patent/ATE273357T1/de not_active IP Right Cessation
- 1998-12-18 KR KR1020007006612A patent/KR100590437B1/ko not_active Expired - Fee Related
- 1998-12-18 BR BRPI9815177-0A patent/BR9815177B1/pt not_active IP Right Cessation
- 1998-12-18 ES ES98964166T patent/ES2223145T5/es not_active Expired - Lifetime
- 1998-12-18 CN CN98812347A patent/CN1117128C/zh not_active Expired - Fee Related
- 1998-12-18 US US09/215,474 patent/US6053971A/en not_active Expired - Lifetime
- 1998-12-18 AU AU19351/99A patent/AU741998B2/en not_active Ceased
- 1998-12-18 WO PCT/US1998/027143 patent/WO1999031191A1/en not_active Ceased
- 1998-12-18 DE DE69825627T patent/DE69825627T3/de not_active Expired - Lifetime
-
2010
- 2010-08-20 JP JP2010185095A patent/JP2010280901A/ja not_active Withdrawn
-
2014
- 2014-05-29 JP JP2014111137A patent/JP2014177640A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1042419B1 (en) | 2004-08-11 |
| JP2010280901A (ja) | 2010-12-16 |
| DE69825627D1 (de) | 2004-09-16 |
| US6053971A (en) | 2000-04-25 |
| DE69825627T3 (de) | 2008-05-21 |
| CN1282359A (zh) | 2001-01-31 |
| EP1042419A1 (en) | 2000-10-11 |
| KR20010033216A (ko) | 2001-04-25 |
| JP2002508431A (ja) | 2002-03-19 |
| EP1042419B2 (en) | 2007-08-01 |
| ATE273357T1 (de) | 2004-08-15 |
| KR100590437B1 (ko) | 2006-06-19 |
| ES2223145T3 (es) | 2005-02-16 |
| BR9815177A (pt) | 2000-10-10 |
| CN1117128C (zh) | 2003-08-06 |
| BR9815177B1 (pt) | 2008-11-18 |
| AU741998B2 (en) | 2001-12-13 |
| WO1999031191A1 (en) | 1999-06-24 |
| DE69825627T2 (de) | 2005-09-22 |
| AU1935199A (en) | 1999-07-05 |
| ES2223145T5 (es) | 2008-02-01 |
| CA2314924A1 (en) | 1999-06-24 |
| JP2014177640A (ja) | 2014-09-25 |
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