JP2002526590A5 - - Google Patents
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- JP2002526590A5 JP2002526590A5 JP2000574179A JP2000574179A JP2002526590A5 JP 2002526590 A5 JP2002526590 A5 JP 2002526590A5 JP 2000574179 A JP2000574179 A JP 2000574179A JP 2000574179 A JP2000574179 A JP 2000574179A JP 2002526590 A5 JP2002526590 A5 JP 2002526590A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- coating composition
- powder coating
- anhydride
- diol
- 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.)
- Pending
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- 239000008199 coating composition Substances 0.000 description 74
- 239000000843 powder Substances 0.000 description 72
- 229920002601 oligoester Polymers 0.000 description 45
- 239000000376 reactant Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- -1 Hydroxyl Chemical group 0.000 description 31
- 150000002009 diols Chemical class 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
- 238000000034 method Methods 0.000 description 30
- 125000002723 alicyclic group Chemical group 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 28
- 229920005862 polyol Polymers 0.000 description 27
- 150000003077 polyols Chemical class 0.000 description 27
- 150000008064 anhydrides Chemical class 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- 239000004971 Cross linker Substances 0.000 description 16
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 16
- 150000004820 halides Chemical class 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 14
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 10
- QPGBFKDHRXJSIK-UHFFFAOYSA-N 2-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=C(C(O)=O)C=CC=C1C(O)=O QPGBFKDHRXJSIK-UHFFFAOYSA-N 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical group OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 6
- RYRZSXJVEILFRR-UHFFFAOYSA-N 2,3-dimethylterephthalic acid Chemical compound CC1=C(C)C(C(O)=O)=CC=C1C(O)=O RYRZSXJVEILFRR-UHFFFAOYSA-N 0.000 description 6
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 6
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 6
- MLEKPSLFBDMVPB-UHFFFAOYSA-N 4,4-dimethylcyclohexane-1,1-dicarboxylic acid Chemical compound CC1(C)CCC(C(O)=O)(C(O)=O)CC1 MLEKPSLFBDMVPB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 2
- RKLJSBNBBHBEOT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropanoyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)C(=O)OC(=O)C(C)(C)CO RKLJSBNBBHBEOT-UHFFFAOYSA-N 0.000 description 2
- MKRXFCTUDBWWFU-UHFFFAOYSA-N 1,2,2,4-tetramethylcyclobutane-1,3-diol Chemical compound CC1C(O)C(C)(C)C1(C)O MKRXFCTUDBWWFU-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- OKWPXFFBOOWJHC-UHFFFAOYSA-N 2-ethenylcyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1C=C OKWPXFFBOOWJHC-UHFFFAOYSA-N 0.000 description 2
- BUYHVRZQBLVJOO-UHFFFAOYSA-N 2-ethyl-2,4-dimethylhexane-1,3-diol Chemical compound CCC(C)C(O)C(C)(CC)CO BUYHVRZQBLVJOO-UHFFFAOYSA-N 0.000 description 2
- QNKRHLZUPSSIPN-UHFFFAOYSA-N 2-ethyl-2-(2-methylpropyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CC(C)C QNKRHLZUPSSIPN-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- SHDLPQHFZRTKBH-UHFFFAOYSA-N 4,4,6-trimethyloxepan-2-one Chemical compound CC1COC(=O)CC(C)(C)C1 SHDLPQHFZRTKBH-UHFFFAOYSA-N 0.000 description 2
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 2
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 229940100573 methylpropanediol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical group [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KVBJJSJIIHDBRJ-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid;cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1.OC(=O)C1CCCCC1C(O)=O KVBJJSJIIHDBRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011289 tar acid Substances 0.000 description 1
- CAWZOADDWCXSEF-UHFFFAOYSA-N triazolo[4,5-b]pyridine Chemical compound [CH]1C=CN=C2N=NN=C21 CAWZOADDWCXSEF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/156,050 US6248843B1 (en) | 1998-09-18 | 1998-09-18 | Powder coatings based on branched oligoesters and triazole blocked polyisocyanates |
| US09/156,050 | 1998-09-18 | ||
| PCT/US1999/020690 WO2000017276A1 (en) | 1998-09-18 | 1999-09-09 | Powder coatings based on branched oligoesters and triazole blocked polyisocyanates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002526590A JP2002526590A (ja) | 2002-08-20 |
| JP2002526590A5 true JP2002526590A5 (https=) | 2006-11-02 |
Family
ID=22557870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000574179A Pending JP2002526590A (ja) | 1998-09-18 | 1999-09-09 | 枝分れオリゴエステルおよびトリアゾール封鎖ポリイソシアネートに基づく粉体塗料 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6248843B1 (https=) |
| EP (1) | EP1114101B1 (https=) |
| JP (1) | JP2002526590A (https=) |
| KR (1) | KR100650830B1 (https=) |
| CN (1) | CN1194057C (https=) |
| AT (1) | ATE264373T1 (https=) |
| AU (1) | AU768278B2 (https=) |
| BR (1) | BR9913795A (https=) |
| CA (1) | CA2344539C (https=) |
| CZ (1) | CZ2001981A3 (https=) |
| DE (1) | DE69916472T2 (https=) |
| WO (1) | WO2000017276A1 (https=) |
| ZA (1) | ZA200102127B (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6506783B1 (en) * | 1997-05-16 | 2003-01-14 | The Procter & Gamble Company | Cancer treatments and pharmaceutical compositions therefor |
| FR2849042B1 (fr) * | 2002-12-24 | 2005-04-29 | Rhodia Chimie Sa | Composition polycondensable a reticulation retardee, son utilisation pour realiser des revetements et revetements ainsi obtenus |
| US20080289968A1 (en) * | 2007-05-25 | 2008-11-27 | Basf Corporation | Method of coating a substrate including a simultaneous cure |
| US20090155462A1 (en) * | 2007-12-18 | 2009-06-18 | Carmen Flosbach | Thermal curable polyester powder coating composition |
| EP2072585A1 (de) * | 2007-12-21 | 2009-06-24 | Ems-Patent Ag | Mattierungsmittel für Pulverlacke, wärmehärtbare Beschichtungsmasse sowie deren Verwendungszwecke |
| KR101492401B1 (ko) * | 2008-12-23 | 2015-02-13 | 에스케이케미칼주식회사 | 플라스틱 코팅용 에스테르계 폴리올 |
| US8163850B2 (en) * | 2009-02-06 | 2012-04-24 | Eastman Chemical Company | Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol |
| US9029460B2 (en) * | 2009-02-06 | 2015-05-12 | Stacey James Marsh | Coating compositions containing acrylic and aliphatic polyester blends |
| US8168721B2 (en) | 2009-02-06 | 2012-05-01 | Eastman Chemical Company | Coating compositions containing tetramethyl cyclobutanediol |
| US9029461B2 (en) * | 2009-02-06 | 2015-05-12 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
| US8324316B2 (en) * | 2009-02-06 | 2012-12-04 | Eastman Chemical Company | Unsaturated polyester resin compositions containing 2,2,2,4-tetramethyl-1,3-cyclobutanediol and articles made therefrom |
| KR101503871B1 (ko) * | 2013-04-19 | 2015-03-18 | 주식회사 케이씨씨 | 도료용 유용성 수지 및 그 제조 방법, 및 이를 포함하며 내치핑성 및 외관이 우수한 도막을 형성하는 도료 조성물 |
| US9487619B2 (en) | 2014-10-27 | 2016-11-08 | Eastman Chemical Company | Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol |
| US9650539B2 (en) | 2014-10-27 | 2017-05-16 | Eastman Chemical Company | Thermosetting compositions based on unsaturated polyesters and phenolic resins |
| US9598602B2 (en) | 2014-11-13 | 2017-03-21 | Eastman Chemical Company | Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds |
| US20160340471A1 (en) | 2015-05-19 | 2016-11-24 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
| US20170088665A1 (en) | 2015-09-25 | 2017-03-30 | Eastman Chemical Company | POLYMERS CONTAINING CYCLOBUTANEDIOL AND 2,2 BIS(HYDROXYMETHYL) AlKYLCARBOXYLIC ACID |
| US9988553B2 (en) | 2016-02-22 | 2018-06-05 | Eastman Chemical Company | Thermosetting coating compositions |
| US10011737B2 (en) | 2016-03-23 | 2018-07-03 | Eastman Chemical Company | Curable polyester polyols and their use in thermosetting soft feel coating formulations |
| CN108484894B (zh) * | 2018-05-10 | 2020-07-31 | 黄山嘉恒科技有限公司 | 一种高流平聚酯树脂及其制备方法应用 |
| CN112225860B (zh) * | 2020-10-12 | 2022-05-27 | 美瑞新材料股份有限公司 | 可在低温下多次软化的高硬热塑性聚氨酯树脂及其在异型材成型方面的应用 |
| CN113480706B (zh) * | 2021-07-27 | 2022-12-16 | 江苏斯迪克新材料科技股份有限公司 | 一种uv光固化无氟低表面能材料及其制备方法 |
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| US3721645A (en) | 1971-02-25 | 1973-03-20 | Liner Technology Inc | Polyurethanes stabilized with 1,2,3-,1,2,4-1,2,5-,and 1,3,4-triazoles |
| US3857818A (en) | 1972-09-18 | 1974-12-31 | Cook Paint & Varnish Co | Blocked polyurethane powder coating compositions |
| DE2812252A1 (de) | 1978-03-21 | 1979-10-04 | Bayer Ag | 1,2,4-triazol-blockierte polyisocyanate als vernetzer fuer lackbindemittel |
| US4197353A (en) | 1978-04-14 | 1980-04-08 | Mobil Oil Corporation | Thermosetting powder coating polyesters |
| DE3030588A1 (de) | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von blockierungsmittelfreien polyurethan-pulverlacken mit hoher lagerstabilitaet, die oberhalb 120(grad) c haertbar sind, sowie die danach hergestellten polyurethan-pulverlacke |
| US4442270A (en) * | 1981-06-29 | 1984-04-10 | Eastman Kodak Company | Thermosetting powder coating compositions |
| US4375539A (en) | 1981-07-22 | 1983-03-01 | Eastman Kodak Company | Solid blocked crosslinking agents based on 1,4-cyclohexane bis(methylisocyanate) |
| DE4114800A1 (de) | 1991-05-07 | 1992-11-12 | Bayer Ag | Neue polyesterpolyole sowie deren verwendung als haftvermittler fuer polymersysteme und als polymerweichmacher |
| BE1005819A3 (nl) * | 1992-05-15 | 1994-02-08 | Dsm Nv | Bindmiddelsamenstelling voor poedercoatings toepasbaar in de automobielindustrie. |
| DE4327573A1 (de) | 1993-08-17 | 1995-02-23 | Bayer Ag | Uretdion-Pulverlackvernetzer mit niedriger Schmelzviskosität |
| DE4335845C3 (de) * | 1993-10-20 | 2001-06-13 | Inventa Ag | Wärmehärtende Beschichtungsmasse, deren Herstellung und Verwendung |
| DE4339367A1 (de) | 1993-11-18 | 1995-05-24 | Bayer Ag | Blockierte Polyisocyanate |
| US5610263A (en) | 1994-01-25 | 1997-03-11 | Eastern Michigan University | Water thinned polymeric vehicle for coating compositions with low amounts of volatile oragnic compounds |
| US5910563A (en) | 1994-01-25 | 1999-06-08 | Exxon Chemical Patents, Inc. | Water thinned polymeric vehicle for coating compositions with low amounts of volatile organic compounds |
| US5955550A (en) | 1994-01-25 | 1999-09-21 | Exxon Chemical Patents, Inc. | Polymeric vehicle for providing solventless coating compositions |
| AU1733395A (en) | 1994-01-25 | 1995-08-08 | Eastern Michigan University | Polymeric vehicle effective for providing solventless coating compositions |
| AU1733695A (en) | 1994-01-25 | 1995-08-08 | Eastern Michigan University | Polymeric vehicle for high solids coatings |
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1998
- 1998-09-18 US US09/156,050 patent/US6248843B1/en not_active Expired - Lifetime
-
1999
- 1999-09-09 AU AU59151/99A patent/AU768278B2/en not_active Ceased
- 1999-09-09 WO PCT/US1999/020690 patent/WO2000017276A1/en not_active Ceased
- 1999-09-09 CZ CZ2001981A patent/CZ2001981A3/cs unknown
- 1999-09-09 BR BR9913795-0A patent/BR9913795A/pt not_active IP Right Cessation
- 1999-09-09 DE DE69916472T patent/DE69916472T2/de not_active Expired - Fee Related
- 1999-09-09 CA CA002344539A patent/CA2344539C/en not_active Expired - Fee Related
- 1999-09-09 EP EP99946831A patent/EP1114101B1/en not_active Expired - Lifetime
- 1999-09-09 AT AT99946831T patent/ATE264373T1/de not_active IP Right Cessation
- 1999-09-09 KR KR1020017003449A patent/KR100650830B1/ko not_active Expired - Fee Related
- 1999-09-09 CN CNB998110817A patent/CN1194057C/zh not_active Expired - Fee Related
- 1999-09-09 JP JP2000574179A patent/JP2002526590A/ja active Pending
-
2001
- 2001-03-14 ZA ZA200102127A patent/ZA200102127B/en unknown
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