JP5868001B2 - 低voc塗料における材料およびオリゴマー - Google Patents
低voc塗料における材料およびオリゴマー Download PDFInfo
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- JP5868001B2 JP5868001B2 JP2010521841A JP2010521841A JP5868001B2 JP 5868001 B2 JP5868001 B2 JP 5868001B2 JP 2010521841 A JP2010521841 A JP 2010521841A JP 2010521841 A JP2010521841 A JP 2010521841A JP 5868001 B2 JP5868001 B2 JP 5868001B2
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- Prior art keywords
- carbamate
- group
- functional
- groups
- acid
- 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.)
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- 239000000463 material Substances 0.000 title claims description 100
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 159
- 150000001875 compounds Chemical class 0.000 claims description 140
- 125000000524 functional group Chemical group 0.000 claims description 119
- 239000000203 mixture Substances 0.000 claims description 110
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 90
- 239000007779 soft material Substances 0.000 claims description 89
- 239000008199 coating composition Substances 0.000 claims description 88
- 239000000178 monomer Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 239000003431 cross linking reagent Substances 0.000 claims description 46
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 41
- 239000007795 chemical reaction product Substances 0.000 claims description 38
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 25
- 239000000194 fatty acid Substances 0.000 claims description 25
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 17
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000005058 Isophorone diisocyanate Substances 0.000 description 15
- 150000003141 primary amines Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 14
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 12
- BSBQJOWZSCCENI-UHFFFAOYSA-N 3-hydroxypropyl carbamate Chemical compound NC(=O)OCCCO BSBQJOWZSCCENI-UHFFFAOYSA-N 0.000 description 12
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- 239000011248 coating agent Substances 0.000 description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 12
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
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- 125000001931 aliphatic group Chemical group 0.000 description 11
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 11
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
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- 125000003277 amino group Chemical group 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- DYXPFYWJHRUFPW-UHFFFAOYSA-N 4-ethyldecane-3,3-diol Chemical compound CCCCCCC(CC)C(O)(O)CC DYXPFYWJHRUFPW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 8
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 8
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- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
-
- 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
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
- Y10T428/24983—Hardness
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- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| PCT/US2008/008670 WO2009025703A1 (en) | 2007-08-17 | 2008-07-16 | Materials and oligomers in low voc coatings |
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| JP2010536988A JP2010536988A (ja) | 2010-12-02 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2445975B1 (en) | 2009-06-26 | 2013-10-16 | Basf Se | Method of curing a coating composition comprising a radical curable compound and an organoborane-amine complex |
| EP2780315B1 (de) * | 2011-11-17 | 2018-01-24 | BASF Coatings GmbH | Verwendung von glyceroldiestern als reaktivverdünner und diese enthaltende beschichtungsmittel |
| WO2015023905A1 (en) * | 2013-08-15 | 2015-02-19 | Dow Global Technologies Llc | A process to produce polycarbamate, polycarbamate produced thereby and a coating composition comprising the polycarbamate |
| US9215876B2 (en) | 2014-03-24 | 2015-12-22 | International Business Machines Corporation | 1,3,6-dioxazocan-2-ones and antimicrobial cationic polycarbonates therefrom |
| US9624191B2 (en) | 2014-03-24 | 2017-04-18 | International Business Machines Corporation | Cyclic carbonate monomers and ring opened polycarbonates therefrom |
| CN103923523B (zh) * | 2014-04-15 | 2015-07-15 | 浙江华宝油墨有限公司 | 一种多臂星形丙烯酸酯共聚物改性的聚氨酯油墨及其制备方法 |
| CN108473817B (zh) | 2015-12-28 | 2020-10-20 | 株式会社Kcc | 耐刮擦性优异的单组分型涂料组合物 |
| WO2018222712A1 (en) | 2017-06-02 | 2018-12-06 | Ppg Industries Ohio, Inc. | Polymers, coating compositions containing such polymers, and anti-fingerprint coatings formed therefrom |
| CN107307487B (zh) * | 2017-09-02 | 2018-12-14 | 泉州万商服饰有限公司 | 一种耐腐蚀手套 |
| US12187665B2 (en) * | 2018-05-03 | 2025-01-07 | Axalta Coating Systems Ip Co., Llc | Crosslinking component for binder resins |
| EP3587479A1 (en) * | 2018-06-30 | 2020-01-01 | SABIC Global Technologies B.V. | Composite material having improved aesthetics and color after secondary operations |
| US20240084167A1 (en) * | 2021-04-27 | 2024-03-14 | Allnex Austria Gmbh | Aqueous coating composition for corrosion protection |
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| US2842523A (en) * | 1954-08-12 | 1958-07-08 | Dow Chemical Co | Beta-amino lower-alkyl carbamates and resinous reaction products thereof |
| US2979514A (en) * | 1957-07-16 | 1961-04-11 | Rohm & Haas | Process for preparing carbonatoalkyl acrylates and methacrylates |
| US3082180A (en) * | 1960-10-04 | 1963-03-19 | American Cyanamid Co | Modified melamine-formaldehyde resin for decorative laminating and process for preparing same |
| US3479328A (en) * | 1966-11-18 | 1969-11-18 | Ashland Oil Inc | Novel monomers and polymers |
| US3674838A (en) * | 1969-06-05 | 1972-07-04 | Ashland Oil Inc | Vinyl carbamyloxy carboxylates |
| US4105708A (en) * | 1976-09-07 | 1978-08-08 | American Cyanamid Company | Dimethoxymethyl diethoxymethyl glycoluril and coating compositions containing the same as a cross-linking agent |
| US4126747A (en) * | 1976-12-28 | 1978-11-21 | Union Carbide Corporation | Carbamoyloxy acrylate compounds |
| US4293692A (en) * | 1977-11-17 | 1981-10-06 | American Cyanamid Company | Continuous process for manufacturing substantially fully methylated substantially fully methylolated melamine compositions |
| US4301257A (en) * | 1979-05-18 | 1981-11-17 | Akzona Incorporated | Polyfunctional isocyanates free of alkali and urea groups |
| US4279833A (en) * | 1979-12-17 | 1981-07-21 | Ashland Chemical Company | Acrylic monomers containing carbamate functionality |
| US4340497A (en) * | 1980-03-21 | 1982-07-20 | Union Carbide Corporation | (N-Substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters |
| CS223409B1 (en) * | 1981-04-17 | 1983-10-28 | Slavko Hudecek | Grafted copolymeres and method of preparation of the same |
| US4533254A (en) * | 1981-04-17 | 1985-08-06 | Biotechnology Development Corporation | Apparatus for forming emulsions |
| US4364913A (en) * | 1981-09-24 | 1982-12-21 | American Cyanamid Company | HNCO Manufacture by adiabatic air oxidation of HCN |
| US4389386A (en) * | 1981-09-24 | 1983-06-21 | American Cyanamid Company | HNCO Manufacture by catalytic oxidation of HCN with a Pd doped Ag catalyst |
| US4546046A (en) * | 1983-03-10 | 1985-10-08 | Glasurit America, Inc. | Substrates with flexible coatings from epsilon-caprolactone modified acrylics |
| US4758632A (en) * | 1984-02-17 | 1988-07-19 | American Cyanamid Company | Self-cross-linkable acrylic polymer containing hydroxyalkyl carbamate groups and coating compositions containing the same |
| US5356669A (en) * | 1992-10-23 | 1994-10-18 | Basf Corporation | Composite color-plus-clear coating utilizing carbamate-functional polymer composition in the clearcoat |
| BR9307434A (pt) * | 1992-10-30 | 1999-06-01 | Ppg Industries Inc | Composição formadora de película carável |
| US5336566A (en) * | 1993-04-30 | 1994-08-09 | Basf Corporation | Tri-carbamate-functional crosslinking agents |
| US5994479A (en) * | 1993-07-28 | 1999-11-30 | Basf Corporation | Curable coating compositions containing blends of carbamate-functional compounds |
| US6084038A (en) * | 1993-07-28 | 2000-07-04 | Basf Corporation | Curable coating compositions containing blends of carbamate-functional compounds |
| US5512639A (en) * | 1993-07-28 | 1996-04-30 | Basf Corporation | Curable compositions containing carbamate-modified polyisocyanates |
| US5379947A (en) * | 1993-11-09 | 1995-01-10 | Basf Corporation | Process for producing a powder coating composition |
| US5532061A (en) * | 1994-12-21 | 1996-07-02 | Basf Corporation | Carbamate-functional polyester polymer or oligomer having pendant carbomate groups |
| US5665852A (en) * | 1995-06-07 | 1997-09-09 | Cytec Technology Corp. | Substituted urea and oxime modified amino crosslinking agents, curable compositions containing the same and process for preparing pyrrolidone urea |
| DE19730889A1 (de) * | 1997-07-18 | 1999-01-21 | Basf Coatings Ag | Wäßriger Lack, enthaltend eine mehrkomponentige wäßrige Dispersion |
| US6624275B2 (en) * | 2001-11-02 | 2003-09-23 | Basf Corporation | Water- and organic-soluble carbamate material |
| DE10004498A1 (de) * | 2000-02-02 | 2001-08-09 | Basf Coatings Ag | Diethyloctandioldicarbamate und Diethyloctandioldiallophanate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US7321013B2 (en) * | 2000-12-19 | 2008-01-22 | Basf Corporation | Method for obtaining coating compositions having reduced VOC |
| US7696285B2 (en) * | 2000-12-19 | 2010-04-13 | Basf Coatings Ag | Carbamate functional reactive polymer composition |
| US7205029B2 (en) * | 2000-12-19 | 2007-04-17 | Basf Corporation | Method of providing cured coating films free of popping defects |
| US6541594B2 (en) * | 2000-12-19 | 2003-04-01 | Basf Corporation | Coating compositions containing crosslinkable monomeric difunctional compounds having at least thirty carbon atoms |
| US7163984B2 (en) * | 2000-12-19 | 2007-01-16 | Basf Corporation | Waterborne coating compositions containing monomeric difunctional compounds |
| US6812316B2 (en) * | 2000-12-19 | 2004-11-02 | Basf Corporation | Powder coating compositions and powder slurry coating compositions containing monomeric difunctional compounds |
| US20020136901A1 (en) * | 2000-12-22 | 2002-09-26 | Swaminathan Ramesh | Carbamate-functional resins and their use in high solids coating compositions |
| US6462144B1 (en) * | 2000-12-22 | 2002-10-08 | Basf Corporation | Carbamate-functional resins and their use in high solids coating compositions |
| US6977309B2 (en) * | 2002-10-31 | 2005-12-20 | Basf Corporation | Compounds having a secondary or tertiary hydroxy of halide group separated from a primary carbamate group by three or more carbon atoms and a method of making the same |
| US6858674B2 (en) * | 2002-10-31 | 2005-02-22 | Basf Corporation | Carbamate functional materials, a method of making said materials, and curable coating compositions containing said materials |
| US6900270B2 (en) * | 2002-10-31 | 2005-05-31 | Basf Corporation | Curable coating compositions with carbamate compounds |
| US6812300B2 (en) * | 2001-11-29 | 2004-11-02 | Basf Corporation | Method for making multifunctional materials |
| US6740706B2 (en) * | 2001-12-07 | 2004-05-25 | Basf Corporation | Method for obtaining coating compositions having reduced VOC |
| US6995208B2 (en) * | 2001-12-11 | 2006-02-07 | Basf Corporation | Clearcoat composition for primerless MVSS adhesion |
| US8686090B2 (en) * | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
| US7297742B2 (en) * | 2004-05-11 | 2007-11-20 | Basf Corporation | Low VOC waterborne primer with high film smoothness |
| MX274730B (es) * | 2004-06-11 | 2010-03-25 | Metodo para obtener composiciones de revestimiento que tienen un voc reducido. | |
| US20060217485A1 (en) * | 2005-03-23 | 2006-09-28 | Basf Corporation | Pigment dispersant, method of making coating compositions, and coating compositions |
| MX2009004317A (es) * | 2006-11-29 | 2009-05-05 | Basf Corp | Composicion de revestimiento clara con catalizador acido no bloqueado. |
-
2007
- 2007-08-17 US US11/840,411 patent/US20080124532A1/en not_active Abandoned
-
2008
- 2008-07-16 WO PCT/US2008/008670 patent/WO2009025703A1/en not_active Ceased
- 2008-07-16 EP EP08780207A patent/EP2181135A1/en not_active Withdrawn
- 2008-07-16 KR KR1020107005872A patent/KR20100044896A/ko not_active Withdrawn
- 2008-07-16 JP JP2010521841A patent/JP5868001B2/ja not_active Expired - Fee Related
- 2008-07-16 CN CN200880106418.3A patent/CN101802042A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20080124532A1 (en) | 2008-05-29 |
| WO2009025703A1 (en) | 2009-02-26 |
| CN101802042A (zh) | 2010-08-11 |
| KR20100044896A (ko) | 2010-04-30 |
| EP2181135A1 (en) | 2010-05-05 |
| JP2010536988A (ja) | 2010-12-02 |
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