JP4065849B2 - ヒドロキシル及びカルバメート官能樹脂 - Google Patents
ヒドロキシル及びカルバメート官能樹脂 Download PDFInfo
- Publication number
- JP4065849B2 JP4065849B2 JP2003560115A JP2003560115A JP4065849B2 JP 4065849 B2 JP4065849 B2 JP 4065849B2 JP 2003560115 A JP2003560115 A JP 2003560115A JP 2003560115 A JP2003560115 A JP 2003560115A JP 4065849 B2 JP4065849 B2 JP 4065849B2
- Authority
- JP
- Japan
- Prior art keywords
- carbamate
- hydroxyl
- groups
- functional
- group
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 110
- 229920005989 resin Polymers 0.000 title claims abstract description 77
- 239000011347 resin Substances 0.000 title claims abstract description 77
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 25
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 239000004202 carbamide Substances 0.000 claims abstract description 8
- 239000008199 coating composition Substances 0.000 claims abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 38
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 125000000524 functional group Chemical group 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000012860 organic pigment Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 230000002252 carbamoylating effect Effects 0.000 claims 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 150000003077 polyols Chemical group 0.000 abstract description 37
- 229920005862 polyol Polymers 0.000 abstract description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
- 239000000412 dendrimer Substances 0.000 abstract description 2
- 229920000736 dendritic polymer Polymers 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 description 62
- 239000011248 coating agent Substances 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000003973 paint Substances 0.000 description 36
- -1 p-xylylene diene Chemical class 0.000 description 30
- 125000005442 diisocyanate group Chemical group 0.000 description 24
- 150000008064 anhydrides Chemical group 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 229920003180 amino resin Polymers 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 150000002118 epoxides Chemical group 0.000 description 10
- 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 10
- 239000005058 Isophorone diisocyanate Substances 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 3
- AFVMPODRAIDZQC-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)cyclopentane Chemical compound O=C=NCC1CCCC1N=C=O AFVMPODRAIDZQC-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- IYJMQRLCWBFHJL-UHFFFAOYSA-N 1,11-diisocyanatoundecane Chemical compound O=C=NCCCCCCCCCCCN=C=O IYJMQRLCWBFHJL-UHFFFAOYSA-N 0.000 description 2
- XSJFAAMNRIJDGN-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclobutane Chemical compound O=C=NCC1CCC1CN=C=O XSJFAAMNRIJDGN-UHFFFAOYSA-N 0.000 description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- MYXZTICARLPUED-UHFFFAOYSA-N 1,3-diisocyanatocyclobutane Chemical compound O=C=NC1CC(N=C=O)C1 MYXZTICARLPUED-UHFFFAOYSA-N 0.000 description 2
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- QDTSVCYLAYAFCJ-UHFFFAOYSA-N 1-(isocyanatomethyl)-1-methylcyclohexane Chemical compound O=C=NCC1(C)CCCCC1 QDTSVCYLAYAFCJ-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HPVOTSMEHLZBJY-UHFFFAOYSA-N 2-(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)C(O)=O HPVOTSMEHLZBJY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- OZDFMZUKOBBNHM-UHFFFAOYSA-N 2-ethylhexyl carbamate Chemical compound CCCCC(CC)COC(N)=O OZDFMZUKOBBNHM-UHFFFAOYSA-N 0.000 description 1
- ZMZQVAUJTDKQGE-UHFFFAOYSA-N 2-ethylhydracrylic acid Chemical compound CCC(CO)C(O)=O ZMZQVAUJTDKQGE-UHFFFAOYSA-N 0.000 description 1
- BTDQXGUEVVTAMD-UHFFFAOYSA-N 2-hydroxyethyl carbamate Chemical compound NC(=O)OCCO BTDQXGUEVVTAMD-UHFFFAOYSA-N 0.000 description 1
- FZHYLXLEEBXHEG-UHFFFAOYSA-N 2-methyl-3-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)COC=C(C)C(N)=O FZHYLXLEEBXHEG-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- BSBQJOWZSCCENI-UHFFFAOYSA-N 3-hydroxypropyl carbamate Chemical compound NC(=O)OCCCO BSBQJOWZSCCENI-UHFFFAOYSA-N 0.000 description 1
- JYTYEGKJKIXWOJ-UHFFFAOYSA-N 4-hydroxy-2-methylbutanoic acid Chemical compound OC(=O)C(C)CCO JYTYEGKJKIXWOJ-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- PTOZKHGZLKYQRN-UHFFFAOYSA-N C(O)C(C(=O)O)(C)CO.OCC(C(=O)O)C Chemical compound C(O)C(C(=O)O)(C)CO.OCC(C(=O)O)C PTOZKHGZLKYQRN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- VSKFADHADUWCCL-UHFFFAOYSA-N carbamoperoxoic acid Chemical compound NC(=O)OO VSKFADHADUWCCL-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 239000002320 enamel (paints) Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- MSYLJRIXVZCQHW-UHFFFAOYSA-N formaldehyde;6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound O=C.NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 MSYLJRIXVZCQHW-UHFFFAOYSA-N 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical compound ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000012063 pure reaction product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3278—Hydroxyamines containing at least three hydroxy groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/043,816 US6927271B2 (en) | 2002-01-10 | 2002-01-10 | Hydroxyl and carbamate functional resins |
| PCT/US2002/032976 WO2003060025A1 (en) | 2002-01-10 | 2002-10-16 | Hydroxyl and carbamate functional resins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005514514A JP2005514514A (ja) | 2005-05-19 |
| JP2005514514A5 JP2005514514A5 (enExample) | 2006-01-05 |
| JP4065849B2 true JP4065849B2 (ja) | 2008-03-26 |
Family
ID=21929035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003560115A Expired - Fee Related JP4065849B2 (ja) | 2002-01-10 | 2002-10-16 | ヒドロキシル及びカルバメート官能樹脂 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6927271B2 (enExample) |
| EP (1) | EP1463782B1 (enExample) |
| JP (1) | JP4065849B2 (enExample) |
| AT (1) | ATE304039T1 (enExample) |
| AU (1) | AU2002337866A1 (enExample) |
| BR (1) | BR0214417A (enExample) |
| CA (1) | CA2463924A1 (enExample) |
| DE (1) | DE60206074T2 (enExample) |
| ES (1) | ES2249619T3 (enExample) |
| MX (1) | MXPA04003510A (enExample) |
| WO (1) | WO2003060025A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6838530B2 (en) | 2001-11-29 | 2005-01-04 | Basf Corporation | Method of preparing various multifunctional materials using limited starting reactants |
| US6825286B2 (en) | 2001-11-29 | 2004-11-30 | Basf Corporation | Method for determining the water solubility or water dispersibility of waterborne beta-hydroxy primary carbamate functional graft materials |
| US7122605B2 (en) | 2001-11-29 | 2006-10-17 | Basf Corporation | Method for selective graft polymerization |
| US6812300B2 (en) | 2001-11-29 | 2004-11-02 | Basf Corporation | Method for making multifunctional materials |
| DE102005023728A1 (de) * | 2005-05-23 | 2006-11-30 | Basf Coatings Ag | Lackschichtbildendes Korrosionsschutzmittel und Verfahren zu dessen stromfreier Applikation |
| DE102006053291A1 (de) * | 2006-11-13 | 2008-05-15 | Basf Coatings Ag | Lackschichtbildendes Korrosionsschutzmittel mit guter Haftung und Verfahren zu dessen stromfreier Applikation |
| US8206827B2 (en) * | 2007-03-15 | 2012-06-26 | Nanovere Technologies, Llc | Dendritic polyurethane coating |
| DE102007012406A1 (de) * | 2007-03-15 | 2008-09-18 | Basf Coatings Ag | Verfahren zur Korrosionsschutzausrüstung metallischer Substrate |
| US8568888B2 (en) | 2007-03-15 | 2013-10-29 | Nanovere Technologies, Inc. | Dendritic polyurethane coating |
| US20100163423A1 (en) | 2008-12-29 | 2010-07-01 | Basf Corporation | Electrocoat composition and process replacing phosphate pretreatment |
| JP5623423B2 (ja) | 2008-12-29 | 2014-11-12 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 水性の電着コーティング組成物、リン酸塩前処理の代用法を含む金属の自動車車体をコーティングするための方法、及び、該水性の電着コーティング組成物の製造方法 |
| US8153733B2 (en) | 2008-12-29 | 2012-04-10 | Basf Coatings Gmbh | Electrocoat compositions with amine ligand |
| DE102009007632A1 (de) | 2009-02-05 | 2010-08-12 | Basf Coatings Ag | Beschichtungsmittel für korrosionsstabile Lackierungen |
| KR20120124481A (ko) | 2010-02-05 | 2012-11-13 | 바스프 코팅스 게엠베하 | 코팅 조성물에의 사용을 위한 수지 |
| WO2012115691A1 (en) | 2011-02-22 | 2012-08-30 | Basf Coatings Gmbh | Electrocoat coating with low gloss |
| US20150267315A1 (en) | 2012-11-09 | 2015-09-24 | Basf Coatings Gmbh | Method For Improving Coating Cure For Article Coated In Phosphate-Contaminated Electrocoat Coating Composition And Electrocoat Coating Composition |
| US9334234B2 (en) * | 2014-05-08 | 2016-05-10 | Basf Coatings Gmbh | Method using titanium catalyst for producing carbamate-functional materials |
| US9938429B2 (en) | 2014-07-18 | 2018-04-10 | BASF Coating GmbH | Coatings with flexible hyperbranched polyols |
| JP6661305B2 (ja) | 2014-09-22 | 2020-03-11 | ダウ グローバル テクノロジーズ エルエルシー | 一価金属含有触媒、ポリオールおよび尿素化合物のカルバミル化組成物、ならびにこれを使用したカルバミル化プロセス |
| JP6572569B2 (ja) * | 2015-03-12 | 2019-09-11 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
| CN105968289B (zh) * | 2015-03-12 | 2020-12-25 | 东曹株式会社 | 耐紫外线吸收剂性聚氨酯组合物、使用该组合物的涂布材料 |
| JP6772441B2 (ja) * | 2015-09-02 | 2020-10-21 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
| JP6710975B2 (ja) * | 2015-07-29 | 2020-06-17 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
| US11242465B2 (en) | 2016-10-14 | 2022-02-08 | Sun Chemical Corporation | Aqueous inkjet ink compositions |
| EP4435068A1 (en) | 2023-03-23 | 2024-09-25 | Dover Europe Sàrl | Ink composition and ink jet printing process |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2979514A (en) * | 1957-07-16 | 1961-04-11 | Rohm & Haas | Process for preparing carbonatoalkyl acrylates and methacrylates |
| US3505297A (en) * | 1963-01-21 | 1970-04-07 | Dow Chemical Co | Alkenyl heterocycles and their polymers |
| 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 |
| US4126747A (en) * | 1976-12-28 | 1978-11-21 | Union Carbide Corporation | Carbamoyloxy acrylate compounds |
| 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 |
| US4477624A (en) * | 1981-11-09 | 1984-10-16 | Showa Electric Wire & Cable Co., Ltd. | Heat-resistant synthetic resin composition |
| 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 |
| US4522986A (en) * | 1984-07-20 | 1985-06-11 | General Motors Corporation | Urea flow control agents for urethane paint prepared by reaction of an isocyanate-terminated prepolymer and an ethanolamine |
| JP2592054B2 (ja) * | 1986-01-31 | 1997-03-19 | シャープ株式会社 | データ記録方法 |
| DE3701409A1 (de) * | 1987-01-20 | 1988-07-28 | Bayer Ag | Verfahren zur herstellung eines thioxotropiermittels, insbesondere fuer lagerstabile polyurethan-reaktivsysteme |
| US4820830A (en) * | 1987-03-02 | 1989-04-11 | King Industries, Inc. | Certain hydroxyalkyl carbamates, polymers and uses thereof |
| US4791168A (en) * | 1987-04-15 | 1988-12-13 | Basf Corporation, Inmont Division | Polyurethane resins in water-dilutable basecoats having low flash and quick-drying characteristics |
| US4868298A (en) * | 1988-06-22 | 1989-09-19 | Cargill, Incorporated | Continuous process for the production of blocked isocyanate containing polyisocyanurates |
| JPH06102773B2 (ja) * | 1988-12-07 | 1994-12-14 | 日本パーカライジング株式会社 | メッキ鋼板の表面処理方法 |
| US5223600A (en) * | 1989-08-22 | 1993-06-29 | Uwe Keppeler | Heterofunctional diols and polyurethane elastomers manufactured therefrom |
| SE468771B (sv) * | 1992-02-26 | 1993-03-15 | Perstorp Ab | Dendritisk makromolekyl av polyestertyp, foerfarande foer framstaellning daerav samt anvaendning daerav |
| DE4218184A1 (de) * | 1992-06-02 | 1993-12-09 | Bayer Ag | Wäßriges Bindemittelgemisch und seine Verwendung |
| US5326815A (en) * | 1992-09-29 | 1994-07-05 | Basf Corporation | Polyurethane coating composition derived from polyester polyol containing long-chain aliphatic polyol |
| 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 |
| US5792810A (en) * | 1995-10-06 | 1998-08-11 | Basf Corporation | Curable coating composition including compound having carbamate and hydroxyl functionality |
| US5373069A (en) * | 1993-07-28 | 1994-12-13 | Basf Corporation | Curable carbamate-functional polymers |
| SE503559C2 (sv) * | 1994-09-08 | 1996-07-08 | Inst Polymerutveckling Ab | Strålningshärdbar hypergrenad polyester, förfarande för dess framställning samt dess användning |
| SE503342C2 (sv) * | 1994-10-24 | 1996-05-28 | Perstorp Ab | Hyperförgrenad makromolekyl av polyestertyp samt förfarande för dess framställning |
| US5580922A (en) * | 1995-06-06 | 1996-12-03 | Weyerhaeuser Company | Cellulose products treated with isocyanate compositions |
| KR100237105B1 (ko) * | 1995-10-13 | 2000-01-15 | 우노 마사야스 | 열경화성 조성물, 도장마무리방법 및 도장물품 |
| SE509240C2 (sv) | 1996-05-28 | 1998-12-21 | Perstorp Ab | Termoplastisk kompound bestående av en termoplastisk polymer bunden till en dendritisk eller hyperförgrenad makromolekyl samt komposition och produkt därav |
| US5693724A (en) * | 1996-07-01 | 1997-12-02 | Basf Corporation | Low VOC curable coating composition utilizing carbamate-functional compound |
| US5693723A (en) * | 1996-07-01 | 1997-12-02 | Basf Corporation | Low voc curable coating composition utilizing carbamate-functional compound |
| KR20000057167A (ko) * | 1996-11-25 | 2000-09-15 | 오노 알버어스 | 산 작용성 및 에폭시 작용성 폴리에스테르 수지 |
| US5852162A (en) * | 1997-06-27 | 1998-12-22 | Morton International, Inc. | Low molecular weight hydroxy functional polyesters for coatings |
| US5976615A (en) * | 1997-07-09 | 1999-11-02 | Basf Corporation | Carbamate curable coating composition and method for improved adhesion |
| US5945499A (en) * | 1997-11-12 | 1999-08-31 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
| DE19953445A1 (de) | 1999-11-06 | 2001-05-17 | Basf Coatings Ag | Selbstvernetzende Polyurethane und Pfropfmischpolymerisate auf Polyurethanbasis sowie ihre Verwendung zur Herstellung von Beschichtungsstoffen, Klebstoffen und Dichtungsmassen |
| US6569956B1 (en) | 1999-12-22 | 2003-05-27 | Basf Corporation | Hyperbranched polyol macromolecule, method of making same, and coating composition including same |
| DE10030869A1 (de) | 2000-06-23 | 2002-01-03 | Basf Ag | Mehrfunktionelle Polyisocyanat-Polyadditionsprodukte |
| US6462144B1 (en) | 2000-12-22 | 2002-10-08 | Basf Corporation | Carbamate-functional resins and their use in high solids coating compositions |
| US7008995B2 (en) | 2001-09-27 | 2006-03-07 | Basf Corporation | Carboxy resin crosslinkers |
-
2002
- 2002-01-10 US US10/043,816 patent/US6927271B2/en not_active Expired - Lifetime
- 2002-10-16 CA CA002463924A patent/CA2463924A1/en not_active Abandoned
- 2002-10-16 BR BR0214417-4A patent/BR0214417A/pt not_active IP Right Cessation
- 2002-10-16 AU AU2002337866A patent/AU2002337866A1/en not_active Abandoned
- 2002-10-16 MX MXPA04003510A patent/MXPA04003510A/es active IP Right Grant
- 2002-10-16 EP EP02773768A patent/EP1463782B1/en not_active Expired - Lifetime
- 2002-10-16 JP JP2003560115A patent/JP4065849B2/ja not_active Expired - Fee Related
- 2002-10-16 AT AT02773768T patent/ATE304039T1/de not_active IP Right Cessation
- 2002-10-16 ES ES02773768T patent/ES2249619T3/es not_active Expired - Lifetime
- 2002-10-16 DE DE60206074T patent/DE60206074T2/de not_active Expired - Lifetime
- 2002-10-16 WO PCT/US2002/032976 patent/WO2003060025A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005514514A (ja) | 2005-05-19 |
| US6927271B2 (en) | 2005-08-09 |
| ES2249619T3 (es) | 2006-04-01 |
| WO2003060025A1 (en) | 2003-07-24 |
| ATE304039T1 (de) | 2005-09-15 |
| BR0214417A (pt) | 2004-09-14 |
| US20030130471A1 (en) | 2003-07-10 |
| DE60206074T2 (de) | 2006-06-29 |
| AU2002337866A1 (en) | 2003-07-30 |
| DE60206074D1 (de) | 2005-10-13 |
| MXPA04003510A (es) | 2004-07-22 |
| EP1463782A1 (en) | 2004-10-06 |
| EP1463782B1 (en) | 2005-09-07 |
| CA2463924A1 (en) | 2003-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4065849B2 (ja) | ヒドロキシル及びカルバメート官能樹脂 | |
| US5994479A (en) | Curable coating compositions containing blends of carbamate-functional compounds | |
| EP1370622B1 (en) | Carbamate-functional, resins and their use in high solids coating compositions | |
| US5854385A (en) | Coating compositions with low molecular weight carbamate or urea component | |
| JP3722891B2 (ja) | カルバメート基を有するポリウレタンポリマーあるいはオリゴマー、その製造法、およびコーティング組成物 | |
| US5639828A (en) | Carbamate or isocyanate component, carbamate-reactive or active H component and epoxide | |
| US5872195A (en) | Curable coating compositions containing carbamate additive | |
| US5576063A (en) | Multiple layer coating method | |
| US6084038A (en) | Curable coating compositions containing blends of carbamate-functional compounds | |
| US5770650A (en) | Curable compositions for coatings | |
| EP0718339A2 (en) | Carbamate-functional polyester polymer or oligomer having pendant carbamate groups | |
| EP0767232B1 (en) | Curable compositions for coatings | |
| US6080825A (en) | Curable coating compositions containing blends of carbamate-functional compounds | |
| JP2006504840A (ja) | ３個以上の炭素原子によって第一カルバメート基から分離された第二ヒドロキシ基もしくは第３ヒドロキシ基またはハロゲン化物基を有する反応性化合物を含有する硬化性塗料およびその製造法 | |
| US20020136901A1 (en) | Carbamate-functional resins and their use in high solids coating compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050418 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050418 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070426 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070516 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20070813 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20070820 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071116 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20071213 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080107 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4065849 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110111 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110111 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120111 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130111 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140111 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |