CN100432172C - 耐久性二组分聚氨酯地板涂料 - Google Patents
耐久性二组分聚氨酯地板涂料 Download PDFInfo
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- CN100432172C CN100432172C CNB2005101040134A CN200510104013A CN100432172C CN 100432172 C CN100432172 C CN 100432172C CN B2005101040134 A CNB2005101040134 A CN B2005101040134A CN 200510104013 A CN200510104013 A CN 200510104013A CN 100432172 C CN100432172 C CN 100432172C
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- acid
- polyhydroxy polycarboxylic
- acrylate
- functional
- monomer
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- 239000011248 coating agent Substances 0.000 title description 8
- 238000000576 coating method Methods 0.000 title description 8
- 239000004814 polyurethane Substances 0.000 title description 4
- 229920002635 polyurethane Polymers 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 5
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 5
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 150000004985 diamines Chemical group 0.000 claims 1
- 239000008199 coating composition Substances 0.000 abstract description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001879 gelation Methods 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- -1 propylidyne acetate Chemical compound 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 125000004427 diamine group Chemical group 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UPZFLZYXYGBAPL-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCCO1 UPZFLZYXYGBAPL-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical class OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- HPPRPVHAOUSJDK-WLHGVMLRSA-N C(\C=C\C(=O)O)(=O)O.C(C)C(CCCCC)SP(O)(O)=S Chemical class C(\C=C\C(=O)O)(=O)O.C(C)C(CCCCC)SP(O)(O)=S HPPRPVHAOUSJDK-WLHGVMLRSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH 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
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
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- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及一种二组分的地板涂料组合物，其包含：(a)一种以至少含有两个羟基的叔胺中和的具有酸性基团的多羟基聚丙烯酸酯的水溶液，所述溶液包含一种有机溶剂；和(b)一种脂肪族的聚异氰酸酯。
Description
本发明涉及一种含水、含溶剂的耐久性二组分聚氨酯地板涂料体系。
二组分含水、含溶剂的聚氨酯涂料体系在早先的技术领域中已被揭示，参见例如U.S.Pat.No.5,614,584等文献。然而，在早先的技术领域中所描述的这种涂料中通常使用中和剂以中和多羟基化合物组分上的酸性基团，这就导致了该涂料不适于作为地板涂料使用。
本发明所解决的问题是对用以制造耐久性地板涂料的含水、含溶剂二组分聚氨酯地板涂料体系的需求问题。
技术领域
本发明提供了一种二组分地板涂料组合物，其组成成分为：(a)一种以至少含有两个羟基的叔胺中和的具有酸性基团的多羟基聚丙烯酸酯的水溶液，所述溶液包含一种有机溶剂；和(b)一种脂肪族的聚异氰酸酯。
本发明进一步提供了一种利用上述二组分地板涂料组合物涂覆地板的方法。
发明内容
除特别说明外，本发明所述百分比均为以组合物整体为基准的重量百分比。本发明中，术语“(甲基)丙烯酸”指丙烯酸或甲基丙烯酸，术语“(甲基)丙烯酸酯”指丙烯酸酯或甲基丙烯酸酯。术语“丙烯酸聚合物”指丙烯酸单体(即丙烯酸(AA)、甲基丙烯酸(MAA)以及它们的酯类)的聚合物，和含有40％以上的丙烯酸单体的共聚物。AA和MAA的酯类包括但不限于：甲基丙烯酸甲酯(MMA)、甲基丙烯酸乙酯(EMA)、甲基丙烯酸丁酯(BMA)、甲基丙烯酸羟乙酯(HEMA)、丙烯酸甲酯(MA)、丙烯酸乙酯(EA)、丙烯酸丁酯(BA)、丙烯酸羟乙酯(HEA)和丙烯酸羟丙酯(HPA)，以及其它AA或MAA的烷基酯类。较佳的丙烯酸聚合物含有45％以上由(甲基)丙烯酸或(甲基)丙烯酸酯单体转化而来的单体残基，而最佳为含有50％以上。术语“乙烯基单体”指适于加成聚合且带有单一的可聚合碳-碳双键的单体。“乙烯基单体”包括但不限于：丙烯酸单体、苯乙烯(STY)和α-甲基苯乙烯(AMS)。
“酸官能的单体”指带有羧酸基团的单烯键式不饱和单体。适宜的羧酸单体包括单烯键式不饱和(C3-C9)羧酸单体，包括单羧酸或二羧酸。例如，不饱和的单羧酸包括丙烯酸、甲基丙烯酸、α-乙基丙烯酸、β，β-二甲基丙烯酸、乙烯基乙酸、烯丙基乙酸、次乙基乙酸、次丙基乙酸、巴豆酸、丙烯酰氧丙酸以及它们的碱和金属盐类。适宜的二羧酸单体包括，例如马来酸、马来酸酐、延胡索酸、衣康酸、柠康酸、中康酸、亚甲基丙二酸以及它们的碱和金属盐。其它适宜的酸性单烯键式不饱和单体包括不饱和脂肪二羧酸的偏酯(烷基半酯)；例如，衣康酸、延胡索酸、马来酸的烷基半酯，其中的烷基基团包含有1到6个碳原子(甲基酸衣康酸酯、丁基酸衣康酸酯、乙基酸延胡索酸酯、丁基酸延胡索酸酯和甲基酸马来酸酯)。较佳的是，单烯键式不饱和(C3-C9)羧酸单体选自丙烯酸和甲基丙烯酸中的一种或多种。
“羟基官能的单体”指带有羟基官能团的单烯键式不饱和单体。在一优选实施例中，所述的羟基官能的单体为(甲基)丙烯酸羟烷基酯。所述羟烷基团至少包含一个羟基基团。例举但不限于：HEA、HEMA、HPA、HPMA(甲基丙烯酸羟丙基酯)和HBA(丙烯酸羟丁基酯)。另一羟基官能的单体的例子是乙烯醇。
为了达到本发明的目的，使用含有至少两个羟基的叔胺中和所述涂料组合物中多羟基化合物组分中的酸基团。该化合物不含有伯胺或仲胺基团。较优的叔胺化合物包括，例如三链烷醇胺类、烷基二链烷醇胺类以及仲二胺与氧化烯的反应产物类。三链烷醇胺类举例包括：三乙醇胺和三异丙醇胺。烷基二链烷醇胺类举例包括：烷基二乙醇胺类(如甲基二乙醇胺(MDEA))和烷基二异丙基醇胺类。在烷基二链烷醇胺中，较优的烷基基团为C1-C4未取代烷基基团。仲二胺与氧化烯的反应产物类举例为1，4-双(2-羟乙基)哌嗪。较佳的是，涂料组合物应基本不含伯胺和仲胺。
涂料组合物中的多羟基化合物组分中含有含水的多羟基聚丙烯酸酯，即带有羟基官能度的丙烯酸聚合物。较优的，所述聚合物包含30％以上由羟基官能的单体衍生而来的单体单元，更优的则含35％以上，而最优的则达到40％以上。较优的，所述聚合物含有80％以下由羟基官能的单体衍生而来的单体单元，更优的则含60％以下。较优的，所述聚合物含有10％以下由酸官能的单体衍生而来的单体单元，更优的则含9％以下。较优的，所述聚合物含有5％以上的由酸官能的单体衍生而来的单体单元，更优的则含7％以上。在本发明的一个实施例中，所述聚合物包含20％以上由苯乙烯或α-甲基苯乙烯衍生而来的单体单元，更优的为含30％以上；较优的，所述聚合物含有60％以下由苯乙烯或α-甲基苯乙烯衍生而来的单体单元，更优的为含50％以下。较优的所述聚合物包含的单体单元是由苯乙烯衍生而来。
较佳的所述多羟基聚丙烯酸酯是通过溶液聚合反应制备而得。较优的供溶液聚合反应用的溶剂包括乙二醇醚和碳酸盐类。所述溶剂举例包括二(丙二醇)单甲醚、二(丙二醇)二甲醚、二(丙二醇)、丙二醇、二(乙二醇)、乙二醇、二(乙二醇)二乙醚、二(乙二醇)二甲醚、乙二醇单乙醚、乙二醇单丁醚、二(乙二醇)单乙醚、二(乙二醇)单丁醚、碳酸亚乙酯、碳酸亚丙酯和碳酸二乙酯。尤其优选的是二(丙二醇)单甲酯(以DowanolTMDPM的商品名由Dow公司提供)。将由溶液聚合反应得到的多羟基聚丙烯酸酯溶液与至少含有两个羟基基团的叔胺混合，以中和聚合物上的酸官能团，并加入其它成分以生成涂料组合物中的多羟基化合物组分。所述的其它成分包括：表面活性剂(如，氟表面活性剂类)、消泡剂(如，基于聚硅酮的消泡剂)和水。较优的在最终的多羟基聚丙烯酸酯水溶液中所含的有机溶剂量为25％以下，且较优的最终的多羟基聚丙烯酸水溶液中有机溶剂量为2％以上。
较优的通过凝胶渗透色谱法测得的多羟基聚丙烯酸酯的数均分子量为小于20,000，更优的则为不大于10,000，最优的则为小于5,000。较优的多羟基聚丙烯酸酯的数均分子量Mn为大于500，最优的则为大于1,000。
涂料组合物中多羟基化合物组分和异氰酸酯组分临用前混合，从而形成异氰酸酯在多羟基化合物组分中的分散体系。较优的，所得混合物在2h内涂覆于地板上。较优的异氰酸酯类为可溶于水或可分散于水中的脂肪族异氰酸酯类。尤为优选的是由己二异氰酸酯(HDI)构成的亲水化修饰的聚合异氰酸酯类，例如，所含异氰酸酯当量为200-320的聚合异氰酸酯。亲水性修饰的聚合物异氰酸酯可由亲水性的多羟基化合物制得，或通过与酸性的或带电荷的官能团结合制得。此类基于HDI的亲水性修饰的聚合物异氰酸酯的商业化实例为由Bayer公司提供的BayhydurTM302和BayhydurTMXP-7148。
实施例
多羟基聚丙烯酸酯树脂的制备：
将聚合反应溶剂(DowanolTMDPM)装入反应烧瓶内，加热至70℃以上。将引发剂料(根据单体量计为0.3重量％)和单体料(单体混合物的5％)加入前述的反应烧瓶内，加热至160℃。所述单体和引发剂给料在15min后进行且在3h内完成。残留单体水平随附加引发剂的添加而降低。将聚合物冷却至75℃，加入含水中和剂。MDEA指甲基二乙醇胺，DMEA则指N，N-二甲基-2-乙醇胺。将所述聚合物水溶液保持50℃15-20min后，冷却至室温。
所得样品溶于四氢呋喃(Fisher Scientific公司，认证级别，稳定化的)中，以备凝胶渗透色谱法测定，聚合物溶液经0.45μm滤膜过滤。分离在液相色谱仪上进行，所述液相色谱仪由一台AgilentTM1100型等度泵(Waldbronn，德国)、一台GilsonTM234型自动进样器(Villiers le Bel，法国)、以及均控温为40℃的一台EppendorfTMCH-430型柱温箱(麦迪逊Madison，威斯康星州)和一台WatersTM410型差示折光仪(马尔福德Milford，马萨诸塞州)组成。系统控制、数据获取以及数据处理通过2.0版的Cirrus
软件(Polymer Laboratories，Church Stretton，英国)进行。SEC分离以1ml/min的流速在THF(认证级别)中进行，所用的SEC柱组由三根用聚苯乙烯-二乙烯基苯凝胶(标明孔径为100
、103 
和104 
，粒径5μm)填充的PLgel柱(300×7.5mm ID)组成，购自Polymer Laboratories(Church Stretton，英国)。取100μl浓度C＝2mg/ml的样品溶液用于SEC分离。所分析样品的“表观”分子量通过样品GPC表以及PS标准的校正曲线(三级拟合)进行计算。
二组分透明涂料的制备：
二组分透明涂料中的组分A是由100％固体的脂肪族聚异氰酸酯组成。适用的聚异氰酸酯举例为由Bayer公司提供的BayhydurTM302和BayhydurTMXP-4178。
组分B溶液则是将实施例1-19所得的多羟基聚丙烯酸酯树脂加入到含有0.05份BykTM340消泡剂和0.01份BykTM025氟表面活性剂润湿助剂的水溶液中，所述的两种添加剂均由Byk Chemie出售。所述组分B溶液的固体水平经调整达到涂料总固体水平的35％。
将组分A和组分B用顶置搅拌器混合10min，然后将6mil厚度的(湿)涂料涂布于乙烯基复合物地板砖上。涂膜的性能数据列于表5-8中。光泽度测量在涂膜经24h干燥后进行。测定光泽度的方法记载于《Annual Book of ASTM Standards》第15部，卷15.04，Test Procedure ASTM D 1455(2000)中。以产品目录号为4520的格氏Byk Micro-Tri-光泽计(Gardner Byk Micro-Tri-Gloss meter)测定60°和20°的光泽度。防水性的评估则是在涂膜无粘性后以及1天后进行。防水性测定方法记载于《Annual Book ofASTM Standards》第15部，卷15.04，Test Procedure ASTMD 1793(2000)中。在将涂膜经水滴作用1h再擦去后，用以下所述的等级评估涂膜：Ex＝无影响，TrWh＝轻微泛白，Wh＝泛白，Hwh＝严重泛白，B1＝起泡。表5-8所列的铅笔硬度数据是通过《Annual Book of Standards》，卷06.01中ASTMD-3363(2000)所记载的方法测定。粘性时间是通过硝基清漆粘着试验器对表面粘性和干燥速度进行测定。将一层4.0mil厚的测试用抛光剂施加于所述地板砖的表面，并静置待其表观干燥(即当所述抛光剂膜看似干燥)。此时，将所述的粘着试验器{一片1/16英寸厚(1.6mm)、1英寸宽(2.54cm)、3.25英寸(8.3cm)长的铝片倾斜一定角度，使得1平方英寸的区域与抛光剂膜的表面接触。测定上述的倾斜角度，从而使得当5g重物通过一个干燥平坦的衬底被放置于该1平方英寸表面上时，粘着试验器将恰好平衡。}放置于所述抛光剂膜上(1平方英寸的表面(6.5cm2))。500g重物置于粘着试验器1平方英寸的表面之上，并保持5秒，然后移去。若将粘着试验器底部从所述抛光剂膜表面完全拉下所需的时间大于5秒，则认为该表面未消粘，在1min的时间间隔后再次重复上述试验直到测得消粘时间。数值自施加时起每分钟记录。凝胶化时间为所述抛光剂配方转变为非流动性的凝胶所需的时间。
表5：42Sty/8AA/50HEMA+BayhydurTM302
| 树脂 | 中和剂 | 涂膜外观 | 光泽度20°/60° | 凝胶化时间(h) | 粘性时间(h) | 抗水性(粘性/1天) | 铅笔硬度(1天/7天) |
| 1 | 氢氧化钾 | 严重起泡 | 27/64 | 1.3 | 2 | Wh/wh | B/HB |
| 2 | 三乙胺 | 模糊，薄处起泡 | 21/58 | 2 | 5 | Wh/ex | F/H |
| 3 | 氨水 | 透明<sup>*</sup> | 31/70 | 1.5 | 5.5 | TrWh/ex | B/F |
| 4 | DMAE | 模糊，少量起泡 | 18/49 | 2.5 | 4.5 | HWh/TrWh | B/HB |
| 5 | MDEA | 透明 | 44/74 | 2 | 4.5 | HWh/TrWh | B/HB |
| 6 | 三乙醇胺 | 透明 | 75/92 | 1.2 | 5.5 | Ex/ex | 2B/HB |
*凝胶化时可见大量泡沫
表6：42Sty/8AA/50HPA+BayhydurTM302
| 树脂 | 中和剂 | 涂膜外观 | 光泽度20°/60° | 凝胶化时间(h) | 粘性时间(h) | 抗水性(粘性/1天) | 铅笔硬度(1天/7天) |
| 7 | 氢氧化钾 | 薄处起泡 | 28/65 | 1.5 | 2.5 | HWh/Wh | 5B/3B |
| 8 | 三乙胺 | 模糊，少量起泡 | 15/51 | 2.3 | ＞6.5 | TrWh/ex | B/F |
| 9 | 氨水 | 透明<sup>*</sup> | 36/73 | 1.3 | ＞7.5 | TrWh/ex | HB/F |
| 10 | 三乙醇胺 | 透明 | 49/78 | 3.5 | 7 | Ex/ex | HB/HB |
*凝胶化时见大量泡沫
表7：不同水平的HEMA+BayhydurTMXP-7148的组合
| 树脂 | HEMA百分含量 | 涂膜外观 | 光泽度20°/60° | 凝胶化时间(h) | 粘性时间(h) | 抗水性(粘性/1天) | 铅笔硬度(1天/7天) |
| 11 | 50 | 透明 | 73/91 | 1.5 | 6 | TrWh/ex | B/HB |
| 12 | 40 | 透明 | 78/92 | 1.8 | 6.5 | TrWh/TrWh | 3B/B |
| 13 | 35 | 透明 | 78/90 | 2 | 5.8 | TrWh/TrWh | 3B/HB |
| 14 | 30 | 透明 | 77/89 | 2.3 | 5.5 | TrWh/TrWh | 4B/3B |
表8：不同水平的AA+BayhydurTMXP-7148的组合
| 树脂 | AA百分含量 | 涂膜外观 | 光泽度20°/60° | 凝胶化时间(h) | 粘性时间(h) | 抗水性(粘性/1天) | 铅笔硬度(1天/7天) |
| 15 | 8 | 透明 | 75/92 | 1.2 | 5.5 | Ex/ex | 2B/HB |
| 16 | 10 | 透明 | 81/89 | 1.8 | 6.8 | TrWh/TrWh | HB/HB |
| 17 | 15 | 透明 | 51/80 | 2.5 | 5.5 | WhBl/WhBl | 2B/HB |
| 18 | 25 | 模糊 | 4/23 | 1.2 | ＞7 | WhBl/WhBl | 6B+/5B |
Claims (4)
1.一种二组分地板涂料组合物，其包含：
(a)一种用至少含有两个羟基的叔胺中和的具有酸性基团的多羟基聚丙烯酸酯的水溶液，所述溶液包含一种有机溶剂；和
(b)一种脂肪族的聚异氰酸酯；
其中所述的多羟基聚丙烯酸酯含有至少30％的由羟基官能的单体衍生而来的单体单元和不超过10％的由酸官能的单体衍生而来的单体单元；
所述多羟基聚丙烯酸酯中的酸性基团是用三链烷醇胺、C1-C4未取代的烷基二链烷醇胺或用仲二胺与氧化烯的反应产物所中和的；并且
所述脂肪族的聚异氰酸酯可溶于水或可分散于水。
2.如权利要求1所述的组合物，其特征在于，所述的多羟基聚丙烯酸酯含有至少40％的由羟基官能的单体衍生而来的单体单元。
3.一种涂覆地板的方法，所述的方法包括施涂如权利要求1所述的二组分地板涂料组合物。
4.如权利要求3所述的方法，其特征在于，所述的多羟基聚丙烯酸酯是通过溶液聚合反应制备的，且其数均分子量不大于10,000。
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| US20070287824A1 (en) * | 2006-06-08 | 2007-12-13 | Johnson Mitchell T | Waterbased polyurethane floor coating composition |
| JP5484878B2 (ja) * | 2009-12-10 | 2014-05-07 | 日本乳化剤株式会社 | アルカノールアミンを含む水性樹脂組成物 |
| BR112012028721A2 (pt) | 2010-05-12 | 2016-07-19 | 3M Innovative Properties Co | método para reforçar rocha ou superfície de concreto irregulares, superfície revestida e compósito |
| US20120201963A1 (en) * | 2010-10-08 | 2012-08-09 | Ecolab Usa Inc. | Polyurethane floor finishes with hybrid performance |
| US10053597B2 (en) | 2013-01-18 | 2018-08-21 | Basf Se | Acrylic dispersion-based coating compositions |
| CN103540253A (zh) * | 2013-10-16 | 2014-01-29 | 苏州瑞邦塑胶有限公司 | 一种水性双组分聚氨酯涂料 |
| JP7026677B2 (ja) | 2016-10-05 | 2022-02-28 | ローム アンド ハース カンパニー | アミノアルコールで中和されたアクリルポリマー |
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| US5075370A (en) * | 1988-09-01 | 1991-12-24 | Bayer Aktiengesellschaft | Aqueous coating composition based on specific two-component polyurethanes and to a process for its production |
| US5670600A (en) * | 1993-07-03 | 1997-09-23 | Basf Lacke + Farben, Ag | Aqueous two-component polyurethane coating composition, process for its preparation, and its use in processes for the production of a multicoat finish |
| WO1999051658A1 (en) * | 1998-04-06 | 1999-10-14 | Arco Chemical Technology, L.P. | Two-component aqueous polyurethane coatings |
| CN1368524A (zh) * | 2001-01-30 | 2002-09-11 | 罗姆和哈斯公司 | 双组分涂料组合物和制备方法 |
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| DE4137229A1 (de) | 1991-11-13 | 1993-05-19 | Bayer Ag | Verwendung von polyetherpolyolen als zusatzmittel fuer waessrige polyurethanlacke |
| DE4206044A1 (de) * | 1992-02-27 | 1993-09-02 | Bayer Ag | Beschichtungsmittel, ein verfahren zu ihrer herstellung und ihre verwendung |
| US5508340A (en) | 1993-03-10 | 1996-04-16 | R. E. Hart Labs, Inc. | Water-based, solvent-free or low voc, two-component polyurethane coatings |
| DE4326670A1 (de) | 1993-08-09 | 1995-02-16 | Herberts Gmbh | Verfahren zur Herstellung von wäßrigen Überzugsmitteln, die Überzugsmittel und deren Verwendung |
| DE4421823A1 (de) | 1994-06-22 | 1996-01-04 | Basf Lacke & Farben | Aus mindestens 3 Komponenten bestehendes Beschichtungsmittel, Verfahren zu seiner Herstellung sowie seine Verwendung |
| DE4445355A1 (de) * | 1994-12-20 | 1996-06-27 | Herberts Gmbh | Bindemittel, diese enthaltende wäßrige und lösemittelhaltige Überzugsmittel, Verfahren zu deren Herstellung und zur Herstellung von Mehrschichtlackierungen |
| GB0015027D0 (en) | 2000-06-21 | 2000-08-09 | Ppg Ind Ohio Inc | Aqueous coating composition |
-
2005
- 2005-08-27 EP EP05255293A patent/EP1634900B1/en not_active Expired - Fee Related
- 2005-08-27 DE DE602005003081T patent/DE602005003081T2/de not_active Expired - Fee Related
- 2005-08-27 ES ES05255293T patent/ES2296098T3/es active Active
- 2005-08-30 BR BRPI0503809A patent/BRPI0503809B1/pt not_active IP Right Cessation
- 2005-09-08 US US11/222,094 patent/US7452935B2/en active Active
- 2005-09-08 JP JP2005260478A patent/JP2006077247A/ja not_active Withdrawn
- 2005-09-09 CN CNB2005101040134A patent/CN100432172C/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5075370A (en) * | 1988-09-01 | 1991-12-24 | Bayer Aktiengesellschaft | Aqueous coating composition based on specific two-component polyurethanes and to a process for its production |
| US5670600A (en) * | 1993-07-03 | 1997-09-23 | Basf Lacke + Farben, Ag | Aqueous two-component polyurethane coating composition, process for its preparation, and its use in processes for the production of a multicoat finish |
| WO1999051658A1 (en) * | 1998-04-06 | 1999-10-14 | Arco Chemical Technology, L.P. | Two-component aqueous polyurethane coatings |
| CN1368524A (zh) * | 2001-01-30 | 2002-09-11 | 罗姆和哈斯公司 | 双组分涂料组合物和制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1634900B1 (en) | 2007-10-31 |
| CN1746240A (zh) | 2006-03-15 |
| BRPI0503809B1 (pt) | 2016-10-04 |
| BRPI0503809A (pt) | 2006-04-25 |
| US20060058447A1 (en) | 2006-03-16 |
| DE602005003081D1 (de) | 2007-12-13 |
| DE602005003081T2 (de) | 2008-08-21 |
| ES2296098T3 (es) | 2008-04-16 |
| US7452935B2 (en) | 2008-11-18 |
| JP2006077247A (ja) | 2006-03-23 |
| EP1634900A1 (en) | 2006-03-15 |
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