DE4228510A1 - Wäßrige Polyurethanharzdispersion, Verfahren zu deren Herstellung und deren Verwendung in wäßrigen Überzugsmitteln - Google Patents
Wäßrige Polyurethanharzdispersion, Verfahren zu deren Herstellung und deren Verwendung in wäßrigen ÜberzugsmittelnInfo
- Publication number
- DE4228510A1 DE4228510A1 DE4228510A DE4228510A DE4228510A1 DE 4228510 A1 DE4228510 A1 DE 4228510A1 DE 4228510 A DE4228510 A DE 4228510A DE 4228510 A DE4228510 A DE 4228510A DE 4228510 A1 DE4228510 A1 DE 4228510A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- polyurethane resin
- aqueous
- group
- resin dispersion
- 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.)
- Ceased
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 79
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 63
- 239000008199 coating composition Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 36
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 36
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000007787 solid Substances 0.000 claims abstract description 20
- 125000003010 ionic group Chemical group 0.000 claims abstract description 14
- 239000003973 paint Substances 0.000 claims abstract description 12
- 238000009833 condensation Methods 0.000 claims abstract description 8
- 230000005494 condensation Effects 0.000 claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 229920005862 polyol Polymers 0.000 claims description 42
- 150000003077 polyols Chemical class 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 36
- 239000004814 polyurethane Substances 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 229920000728 polyester Polymers 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 19
- 229920002635 polyurethane Polymers 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 16
- 150000002009 diols Chemical class 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 150000001298 alcohols Chemical class 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- 239000004970 Chain extender Substances 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 229940015043 glyoxal Drugs 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- 238000010422 painting Methods 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 13
- 239000002609 medium Substances 0.000 claims 4
- 241000282376 Panthera tigris Species 0.000 claims 1
- 229920001744 Polyaldehyde Polymers 0.000 claims 1
- 150000001491 aromatic compounds Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 21
- 239000000049 pigment Substances 0.000 abstract description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 11
- 239000003960 organic solvent Substances 0.000 abstract description 7
- 239000000945 filler Substances 0.000 abstract description 5
- 239000004922 lacquer Substances 0.000 abstract description 2
- 239000002966 varnish Substances 0.000 abstract description 2
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 239000006259 organic additive Substances 0.000 abstract 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 41
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 37
- -1 amino polyol Chemical class 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000011248 coating agent Substances 0.000 description 31
- 239000010410 layer Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 229920000570 polyether Polymers 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 150000002596 lactones Chemical class 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000004971 Cross linker Substances 0.000 description 10
- 150000002334 glycols Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 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 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 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
- 150000004985 diamines Chemical class 0.000 description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 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 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical class C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000007306 functionalization reaction Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
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- FYJLPFHNDQTYAQ-UHFFFAOYSA-N (2,4-diaminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C(N)=C1 FYJLPFHNDQTYAQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
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- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- PUKYTZJZOCTJFQ-UHFFFAOYSA-N 5,9-diisocyanatotridecane Chemical compound CCCCC(N=C=O)CCCC(N=C=O)CCCC PUKYTZJZOCTJFQ-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- 238000000889 atomisation Methods 0.000 description 2
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- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 238000005886 esterification reaction Methods 0.000 description 2
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical class OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 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
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BNOIMFITGLLJTH-UHFFFAOYSA-N trimethyl methanetricarboxylate Chemical compound COC(=O)C(C(=O)OC)C(=O)OC BNOIMFITGLLJTH-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
- 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
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/83—Chemically modified polymers
-
- 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
- C08G18/83—Chemically modified polymers
- C08G18/84—Chemically modified polymers by aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4228510A DE4228510A1 (de) | 1992-08-27 | 1992-08-27 | Wäßrige Polyurethanharzdispersion, Verfahren zu deren Herstellung und deren Verwendung in wäßrigen Überzugsmitteln |
| CA002104845A CA2104845A1 (en) | 1992-08-27 | 1993-08-25 | Aqueous polyurethane resin dispersion, processes for its preparation, and its use in aqueous coating compositions |
| EP93113619A EP0584818B1 (de) | 1992-08-27 | 1993-08-26 | Wässrige Überzugsmittel enthaltend eine Polyurethanharzdispersion und Verfahren zu deren Herstellung und deren Verwendung |
| CZ931753A CZ175393A3 (en) | 1992-08-27 | 1993-08-26 | Aqueous dispersion of polyurethane resin, process of its preparation and its use in aqueous coating composition |
| ES93113619T ES2125286T3 (es) | 1992-08-27 | 1993-08-26 | Revestimientos acuosos que comprenden una dispersion de poliuretano acuosa, procedimiento para su preparacion y su utilizacion. |
| DE59309174T DE59309174D1 (de) | 1992-08-27 | 1993-08-26 | Wässrige Überzugsmittel enthaltend eine Polyurethanharzdispersion und Verfahren zu deren Herstellung und deren Verwendung |
| AT93113619T ATE174041T1 (de) | 1992-08-27 | 1993-08-26 | Wässrige überzugsmittel enthaltend eine polyurethanharzdispersion und verfahren zu deren herstellung und deren verwendung |
| KR1019930016849A KR940004031A (ko) | 1992-08-27 | 1993-08-27 | 수성폴리우레탄수지 분산액과 그 제조방법 및 수성코팅조성물에서 그 용도 |
| JP5212532A JPH06207141A (ja) | 1992-08-27 | 1993-08-27 | 水性ポリウレタン樹脂分散体、その製法および水性塗料におけるその使用 |
| CN93118235A CN1090309A (zh) | 1992-08-27 | 1993-08-27 | 含水聚氨酯树脂分散液及其制备方法和它在含水涂料组合物中的应用 |
| MX9305242A MX9305242A (es) | 1992-08-27 | 1993-08-27 | Dispersion acuosa de resina de poliuretano, procedimiento para su obtencion y su empleo en recubridores acuosos. |
| TW082107035A TW249810B (https=) | 1992-08-27 | 1993-08-30 | |
| US08/394,553 US5552496A (en) | 1992-08-27 | 1995-02-27 | Aqueous polyurethane resin dispersion, processes for its preparation, and its use in aqueous coating compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4228510A DE4228510A1 (de) | 1992-08-27 | 1992-08-27 | Wäßrige Polyurethanharzdispersion, Verfahren zu deren Herstellung und deren Verwendung in wäßrigen Überzugsmitteln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4228510A1 true DE4228510A1 (de) | 1994-03-03 |
Family
ID=6466565
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4228510A Ceased DE4228510A1 (de) | 1992-08-27 | 1992-08-27 | Wäßrige Polyurethanharzdispersion, Verfahren zu deren Herstellung und deren Verwendung in wäßrigen Überzugsmitteln |
| DE59309174T Expired - Fee Related DE59309174D1 (de) | 1992-08-27 | 1993-08-26 | Wässrige Überzugsmittel enthaltend eine Polyurethanharzdispersion und Verfahren zu deren Herstellung und deren Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59309174T Expired - Fee Related DE59309174D1 (de) | 1992-08-27 | 1993-08-26 | Wässrige Überzugsmittel enthaltend eine Polyurethanharzdispersion und Verfahren zu deren Herstellung und deren Verwendung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5552496A (https=) |
| EP (1) | EP0584818B1 (https=) |
| JP (1) | JPH06207141A (https=) |
| KR (1) | KR940004031A (https=) |
| CN (1) | CN1090309A (https=) |
| AT (1) | ATE174041T1 (https=) |
| CA (1) | CA2104845A1 (https=) |
| CZ (1) | CZ175393A3 (https=) |
| DE (2) | DE4228510A1 (https=) |
| ES (1) | ES2125286T3 (https=) |
| MX (1) | MX9305242A (https=) |
| TW (1) | TW249810B (https=) |
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| DE102007038487A1 (de) * | 2007-08-14 | 2009-02-19 | Basf Coatings Ag | Wässriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
| EP2514778A1 (en) | 2009-09-28 | 2012-10-24 | E. I. du Pont de Nemours and Company | Liquid two-component coating compositions |
| WO2012151357A2 (en) | 2011-05-03 | 2012-11-08 | E. I. Du Pont De Nemours And Company | Two-component coating compositions |
| WO2012151409A2 (en) | 2011-05-03 | 2012-11-08 | E. I. Du Pont De Nemours And Company | Catalyst compound for two-component coating compositions |
| US8865831B2 (en) | 2007-10-19 | 2014-10-21 | Axalta Coating Systems Ip Co., Llc | Two-component coating compositions |
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| US5795925A (en) * | 1995-01-24 | 1998-08-18 | Heywood; Newell W. | Varnish with skid resistant UV light resistant properties |
| DE19512017C1 (de) * | 1995-03-31 | 1996-07-18 | Herberts Gmbh | Verfahren zur Mehrschichtlackierung |
| DE19526478A1 (de) * | 1995-07-20 | 1997-01-23 | Herberts Gmbh | Lack, insbesondere zur Beschichtung von Polymerfolien, mit dem Lack beschichtete Polymerfolie und Verfahren zum Aufbringen der beschichteten Polymerfolie auf Formkörper |
| EP0774475A3 (de) | 1995-11-17 | 1997-10-01 | Basf Ag | Wässerige Dispersionen enthaltend ein Polyurethan mit oximblockierten Isocyanatgruppen und/oder Carbonylgruppen in Keto- oder Aldehydfunktion |
| JP2001509549A (ja) * | 1997-07-11 | 2001-07-24 | マグネシウム テクノロジー リミティド | 金属及び／又は陽極処理した金属基板の封孔方法 |
| US5929190A (en) * | 1997-07-31 | 1999-07-27 | Eastman Kodak Company | (2-Cyanoacetamido) reactive polyurethanes |
| US6037440A (en) * | 1997-07-31 | 2000-03-14 | Eastman Kodak Company | Cross-linked linear (2-cyanoacetamido) reactive polyurethanes |
| WO2000003069A1 (en) * | 1998-07-09 | 2000-01-20 | Magnesium Technology Limited | Sealing procedures for metal and/or anodised metal substrates |
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| KR20010093802A (ko) | 1998-12-07 | 2001-10-29 | 빌프리더 하이더 | 말론산 에스테르/트리아졸 혼합물로 차단된ｈｄｉ삼량체/포름알데히드 안정화 |
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| CN115613369B (zh) * | 2022-10-20 | 2024-04-16 | 莆田达凯新材料有限公司 | 耐热压聚氨酯鞋面涂料、耐热压聚氨酯涂层鞋面及其制备方法 |
| CN116004107B (zh) * | 2022-12-27 | 2023-09-26 | 广州集泰化工股份有限公司 | 一种3c水性涂料及其制备方法和应用 |
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| CN117867483A (zh) * | 2024-01-31 | 2024-04-12 | 武汉迪赛新材料有限公司 | 一种锌铁合金镀层钢板用无铬表面处理液及其制备方法 |
| CN119639328A (zh) * | 2024-12-24 | 2025-03-18 | 安徽佳景美新材料有限公司 | 一种抗菌耐磨水性聚氨酯涂料的制备方法 |
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| GB2097414A (en) * | 1981-04-01 | 1982-11-03 | Fulmer Res Inst Ltd | Protection of metal surfaces |
| DE3326188A1 (de) * | 1983-07-20 | 1985-01-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von organischen polyisocyanaten mit zumindest teilweise blockierten isocyanatgruppen, die nach dem verfahren erhaeltlichen verbindungen und ihre verwendung zur herstellung von polyurethanen, einbrennlacken oder waessrigen polyisocyanatloesungen bzw. -dispersionen |
| DE3333834A1 (de) * | 1983-09-20 | 1985-04-04 | Herberts Gmbh, 5600 Wuppertal | Verfahren zur herstellung von lack-kunstharzen und diese enthaltendes elektrotauchlack-ueberzugsmittel |
| ATE62920T1 (de) * | 1986-09-24 | 1991-05-15 | Akzo Nv | Waesserige ueberzugszusammensetzung und verfahren zum ueberziehen eines substrats damit. |
| JPH03124778A (ja) * | 1989-10-09 | 1991-05-28 | Origin Electric Co Ltd | 二液型ウレタン塗料組成物 |
| GB9101204D0 (en) * | 1990-02-14 | 1991-02-27 | Ici Plc | Production of polyurethane polymers,the polymers so produced and compositions containing them |
| DE4101697A1 (de) * | 1991-01-22 | 1992-07-23 | Bayer Ag | Waessrige polyester fuer festkoerperreiche einbrennlacke |
| US5254637A (en) * | 1991-06-03 | 1993-10-19 | Eastman Kodak Company | Thermosetting coating compositions |
-
1992
- 1992-08-27 DE DE4228510A patent/DE4228510A1/de not_active Ceased
-
1993
- 1993-08-25 CA CA002104845A patent/CA2104845A1/en not_active Abandoned
- 1993-08-26 ES ES93113619T patent/ES2125286T3/es not_active Expired - Lifetime
- 1993-08-26 DE DE59309174T patent/DE59309174D1/de not_active Expired - Fee Related
- 1993-08-26 EP EP93113619A patent/EP0584818B1/de not_active Expired - Lifetime
- 1993-08-26 AT AT93113619T patent/ATE174041T1/de not_active IP Right Cessation
- 1993-08-26 CZ CZ931753A patent/CZ175393A3/cs unknown
- 1993-08-27 KR KR1019930016849A patent/KR940004031A/ko not_active Withdrawn
- 1993-08-27 JP JP5212532A patent/JPH06207141A/ja active Pending
- 1993-08-27 MX MX9305242A patent/MX9305242A/es unknown
- 1993-08-27 CN CN93118235A patent/CN1090309A/zh active Pending
- 1993-08-30 TW TW082107035A patent/TW249810B/zh active
-
1995
- 1995-02-27 US US08/394,553 patent/US5552496A/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5824733A (en) * | 1994-04-30 | 1998-10-20 | Wacker-Chemie Gmbh | Aqueous coating product and a process for producing multiple layer paint coatings whose perceived color varies with the angle from which they are viewed |
| DE10124576A1 (de) * | 2001-05-28 | 2002-12-12 | Basf Coatings Ag | Wäßrige Funktions-Beschichtungsstoffe und integriertes Verfahren zur Herstellung farb- und/oder effektgebender Mehrschichtlackierungen |
| DE10124576B4 (de) * | 2001-05-28 | 2006-03-16 | Basf Coatings Ag | Verfahren zur Herstellung farb- und/oder effektgebender Mehrschichtlackierungen, wäßrige Funktions-Beschichtungsstoffe und deren Verwendung |
| DE102007038487A1 (de) * | 2007-08-14 | 2009-02-19 | Basf Coatings Ag | Wässriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
| US8865831B2 (en) | 2007-10-19 | 2014-10-21 | Axalta Coating Systems Ip Co., Llc | Two-component coating compositions |
| US8907007B2 (en) | 2007-10-19 | 2014-12-09 | Axalta Coating Systems Ip Co., Llc | Process for painting substrates |
| EP2514778A1 (en) | 2009-09-28 | 2012-10-24 | E. I. du Pont de Nemours and Company | Liquid two-component coating compositions |
| WO2012151357A2 (en) | 2011-05-03 | 2012-11-08 | E. I. Du Pont De Nemours And Company | Two-component coating compositions |
| WO2012151409A2 (en) | 2011-05-03 | 2012-11-08 | E. I. Du Pont De Nemours And Company | Catalyst compound for two-component coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| US5552496A (en) | 1996-09-03 |
| MX9305242A (es) | 1994-05-31 |
| EP0584818A1 (de) | 1994-03-02 |
| JPH06207141A (ja) | 1994-07-26 |
| CZ175393A3 (en) | 1994-03-16 |
| KR940004031A (ko) | 1994-03-14 |
| EP0584818B1 (de) | 1998-12-02 |
| CN1090309A (zh) | 1994-08-03 |
| TW249810B (https=) | 1995-06-21 |
| DE59309174D1 (de) | 1999-01-14 |
| ATE174041T1 (de) | 1998-12-15 |
| ES2125286T3 (es) | 1999-03-01 |
| CA2104845A1 (en) | 1994-02-28 |
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