CA2140378C - Coating system settable by heat - Google Patents
Coating system settable by heat Download PDFInfo
- Publication number
- CA2140378C CA2140378C CA002140378A CA2140378A CA2140378C CA 2140378 C CA2140378 C CA 2140378C CA 002140378 A CA002140378 A CA 002140378A CA 2140378 A CA2140378 A CA 2140378A CA 2140378 C CA2140378 C CA 2140378C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- coating system
- mol
- accordance
- atoms
- 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 - Lifetime
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 53
- 239000011248 coating agent Substances 0.000 title claims abstract description 35
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 229920001225 polyester resin Polymers 0.000 claims abstract description 16
- 239000004645 polyester resin Substances 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 9
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims abstract description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 8
- 239000004593 Epoxy Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 6
- 239000011241 protective layer Substances 0.000 claims abstract description 4
- 239000000155 melt Substances 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 17
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 16
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- 239000001361 adipic acid Substances 0.000 claims description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000007872 degassing Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims 1
- 238000009503 electrostatic coating Methods 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 230000032683 aging Effects 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 230000032050 esterification Effects 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920006125 amorphous polymer Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Fertilizers (AREA)
- Manufacturing Of Electric Cables (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4401438.4 | 1994-01-19 | ||
| DE4401438A DE4401438C2 (de) | 1994-01-19 | 1994-01-19 | Wärmehärtbares Beschichtungssystem, dessen Herstellung und Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2140378A1 CA2140378A1 (en) | 1995-07-20 |
| CA2140378C true CA2140378C (en) | 2001-04-03 |
Family
ID=6508230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002140378A Expired - Lifetime CA2140378C (en) | 1994-01-19 | 1995-01-17 | Coating system settable by heat |
Country Status (12)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19806284C2 (de) * | 1998-02-16 | 2000-02-24 | Inventa Ag | Wärmehärtbare Beschichtungsmassen, Verfahren zur Herstellung und deren Verwendung |
| GB9814437D0 (en) * | 1998-07-03 | 1998-09-02 | Ici Plc | Coating composition |
| AT411687B (de) * | 1998-12-07 | 2004-04-26 | Tigerwerk Lack U Farbenfabrik | Pulverbeschichtungssysteme, verfahren zu ihrer herstellung, ihre verwendung zur herstellung von überzügen, polyesterharz hiefür |
| JP3803784B2 (ja) * | 1999-02-25 | 2006-08-02 | 大日本インキ化学工業株式会社 | 粉体塗料用組成物 |
| US6787188B1 (en) | 2000-10-02 | 2004-09-07 | Imperial Chemical Industries Plc | Coating composition |
| US7192994B2 (en) | 2001-04-25 | 2007-03-20 | Mitsubishi Gas Chemical Co., Inc. | Method of producing polyester powdery coating material |
| DE60201700T2 (de) * | 2001-04-25 | 2005-12-15 | Mitsubishi Gas Chemical Co., Inc. | Verfahren zur Herstellung von Pulverbeschichtungsstoff aus Polyester |
| EP1319698A1 (en) * | 2001-12-12 | 2003-06-18 | Dsm N.V. | Method for hotmelt application |
| CA2491520A1 (en) * | 2002-06-19 | 2003-12-31 | Surface Specialties, S.A. | Semi-gloss powder coating compositions |
| JP4640132B2 (ja) * | 2005-11-22 | 2011-03-02 | カシオ計算機株式会社 | プロジェクタ |
| PL2548930T3 (pl) | 2011-07-22 | 2016-01-29 | Ems Patent Ag | Utwardzalny termicznie system powłokowy, sposób jego wytwarzania oraz jego zastosowanie |
| ES2685836T3 (es) | 2013-01-23 | 2018-10-11 | Adeka Corporation | Agente antiestático, composición de agente antiestático, composición de resina antiestática y cuerpo moldeado |
| CN106536592B (zh) * | 2014-07-25 | 2020-12-01 | 帝斯曼知识产权资产管理有限公司 | 无光泽粉末涂层 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1905825A1 (de) | 1969-02-06 | 1970-10-15 | Metallgesellschaft Ag | Verfahren zur Herstellung von Kunststoffueberzuegen aus Polyester |
| US3723572A (en) * | 1970-03-13 | 1973-03-27 | Albert Ag Chem Werke | Synthetic resins |
| BE838160A (fr) * | 1976-02-02 | 1976-05-28 | Nouvelles resines polyesters acides et produits de revetements en poudre prepares a partir de ces resines | |
| DE2621656A1 (de) | 1976-05-15 | 1977-12-01 | Dynamit Nobel Ag | Haertbare pulverfoermige ueberzugsmittel |
| NL164082C (nl) | 1978-10-31 | 1980-11-17 | Unilever Nv | Poederlak. |
| NL8204205A (nl) * | 1982-10-29 | 1984-05-16 | Dsm Resins Bv | Polyester en de toepassing daarvan in poederlak. |
| US4525504A (en) * | 1983-10-24 | 1985-06-25 | Eastman Kodak Company | Stabilized polyester compositions suitable for outdoor applications |
| DE3740932A1 (de) * | 1987-12-03 | 1989-06-15 | Bayer Ag | Verfahren zur herstellung von polyestern und ihre verwendung als bindemittel oder bindemittelkomponente in pulverlacken |
| US4801680A (en) * | 1987-12-30 | 1989-01-31 | Ppg Industries, Inc. | Hydroxyalkylamide powder coating curing system |
| JPH07113074B2 (ja) * | 1988-03-18 | 1995-12-06 | 日本石油株式会社 | ポリエチレン系樹脂組成物 |
| DE3936973A1 (de) | 1989-03-11 | 1991-05-08 | Hoechst Ag | Haertbare, pulverfoermige mischungen |
| US4933429A (en) | 1989-03-13 | 1990-06-12 | General Electric Company | Method for preparing polyester-polyepoxide compositions of high melt viscosity |
| ES2084610T3 (es) | 1989-03-23 | 1996-05-16 | Dsm Nv | Pintura en polvo y una resina de poliester para pintura en polvo. |
| US4999388A (en) | 1989-09-14 | 1991-03-12 | General Electric Company | Branched polyester resin composition having enhanced melt viscosity |
| US5006612A (en) * | 1989-10-18 | 1991-04-09 | Cargill, Incorporated | Polyesters for powder coating resins using an intermediate having low process viscosity |
| KR950012768B1 (ko) * | 1989-12-28 | 1995-10-21 | 고려화학주식회사 | 저온 경화형 폴리에스테르 수지의 제조방법 및 이를 함유하는 분체도료 조성물 |
| GB9006737D0 (en) * | 1990-03-26 | 1990-05-23 | Courtaulds Coatings Ltd | Coating compositions |
| JP2810500B2 (ja) | 1990-07-03 | 1998-10-15 | 日本ペイント株式会社 | 粉体塗料 |
| US5097006A (en) * | 1990-11-21 | 1992-03-17 | U C B S.A. | Weatherable powder coating compositions |
| US5266657A (en) * | 1991-05-29 | 1993-11-30 | Rohm And Haas Company | Monocarboxylic acid power coating curing systems |
| US5245003A (en) * | 1992-01-23 | 1993-09-14 | Eastman Kodak Company | Ternary mixtures of glycols and water that retain fluidity at ambient temperatures |
| US5280089A (en) * | 1992-02-03 | 1994-01-18 | Ferro Corporation | Polyester-acrylic graft polymers for use in powder coatings |
| GB9205137D0 (en) * | 1992-03-10 | 1992-04-22 | Scott Bader Co | Anti-popping agents for powder coating compositions |
-
1994
- 1994-01-19 DE DE4401438A patent/DE4401438C2/de not_active Expired - Fee Related
- 1994-12-22 NZ NZ270274A patent/NZ270274A/en not_active IP Right Cessation
-
1995
- 1995-01-17 KR KR1019950000663A patent/KR0148335B1/ko not_active Expired - Lifetime
- 1995-01-17 TW TW084100365A patent/TW270930B/zh not_active IP Right Cessation
- 1995-01-17 ES ES95100569T patent/ES2131221T3/es not_active Expired - Lifetime
- 1995-01-17 EP EP95100569A patent/EP0664325B1/de not_active Expired - Lifetime
- 1995-01-17 CA CA002140378A patent/CA2140378C/en not_active Expired - Lifetime
- 1995-01-17 DE DE59505735T patent/DE59505735D1/de not_active Expired - Lifetime
- 1995-01-17 AT AT95100569T patent/ATE179447T1/de active
- 1995-01-18 JP JP00591795A patent/JP3565930B2/ja not_active Expired - Lifetime
- 1995-01-18 ZA ZA95402A patent/ZA95402B/xx unknown
- 1995-01-18 AU AU10280/95A patent/AU662864B2/en not_active Expired
- 1995-06-06 US US08/469,171 patent/US6313234B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR950023687A (ko) | 1995-08-18 |
| DE4401438C2 (de) | 1997-09-18 |
| DE4401438A1 (de) | 1995-07-20 |
| TW270930B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-02-21 |
| NZ270274A (en) | 1995-10-26 |
| ATE179447T1 (de) | 1999-05-15 |
| AU662864B2 (en) | 1995-09-14 |
| CA2140378A1 (en) | 1995-07-20 |
| US6313234B1 (en) | 2001-11-06 |
| ES2131221T3 (es) | 1999-07-16 |
| EP0664325B1 (de) | 1999-04-28 |
| DE59505735D1 (de) | 1999-06-02 |
| ZA95402B (en) | 1995-09-26 |
| AU1028095A (en) | 1995-07-27 |
| EP0664325A3 (de) | 1995-10-18 |
| JP3565930B2 (ja) | 2004-09-15 |
| EP0664325A2 (de) | 1995-07-26 |
| JPH07216298A (ja) | 1995-08-15 |
| KR0148335B1 (ko) | 1998-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20150119 |