JPH09241347A - 水性ポリウレタン−ウレア、その調製方法、及び塗料におけるその使用 - Google Patents
水性ポリウレタン−ウレア、その調製方法、及び塗料におけるその使用Info
- Publication number
- JPH09241347A JPH09241347A JP9057130A JP5713097A JPH09241347A JP H09241347 A JPH09241347 A JP H09241347A JP 9057130 A JP9057130 A JP 9057130A JP 5713097 A JP5713097 A JP 5713097A JP H09241347 A JPH09241347 A JP H09241347A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- urea
- molecular weight
- component
- film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920003226 polyurethane urea Polymers 0.000 title claims description 27
- 238000000576 coating method Methods 0.000 title abstract description 33
- 239000011248 coating agent Substances 0.000 title abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000463 material Substances 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000654 additive Substances 0.000 claims abstract description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 239000006185 dispersion Substances 0.000 claims description 39
- 150000001875 compounds Chemical group 0.000 claims description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000007259 addition reaction Methods 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 238000001035 drying Methods 0.000 abstract description 3
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 abstract 2
- 229920003009 polyurethane dispersion Polymers 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 22
- 229920002635 polyurethane Polymers 0.000 description 19
- 239000004814 polyurethane Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- -1 diaryl carbonate Chemical compound 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000004922 lacquer Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- 230000003472 neutralizing effect Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 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 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- SXROUBQUPINISW-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)prop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CN1 SXROUBQUPINISW-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940044613 1-propanol Drugs 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- NJYOAXKKIWINHK-UHFFFAOYSA-N 2-(diethylaminomethyl)-2-ethylpropane-1,3-diol Chemical compound CCN(CC)CC(CC)(CO)CO NJYOAXKKIWINHK-UHFFFAOYSA-N 0.000 description 1
- ZRIHBQRZLROJKT-UHFFFAOYSA-N 2-(diethylaminomethyl)-2-methylpropane-1,3-diol Chemical compound CCN(CC)CC(C)(CO)CO ZRIHBQRZLROJKT-UHFFFAOYSA-N 0.000 description 1
- SQBOBWQFUZSVIL-UHFFFAOYSA-N 2-[(dibutylamino)methyl]-2-ethylpropane-1,3-diol Chemical compound CCCCN(CCCC)CC(CC)(CO)CO SQBOBWQFUZSVIL-UHFFFAOYSA-N 0.000 description 1
- FGRGEJHAFNAVAS-UHFFFAOYSA-N 2-[(dibutylamino)methyl]-2-methylpropane-1,3-diol Chemical compound CCCCN(CCCC)CC(C)(CO)CO FGRGEJHAFNAVAS-UHFFFAOYSA-N 0.000 description 1
- PBIHVCKVWPFHMN-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)CN(C)C PBIHVCKVWPFHMN-UHFFFAOYSA-N 0.000 description 1
- MWSMRYINWRINLC-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-2-methylpropane-1,3-diol Chemical compound CN(C)CC(C)(CO)CO MWSMRYINWRINLC-UHFFFAOYSA-N 0.000 description 1
- AYPUNJXVHMPYJH-UHFFFAOYSA-N 2-[4-(2-aminopropan-2-yl)cyclohexyl]propan-2-amine Chemical compound CC(C)(N)C1CCC(C(C)(C)N)CC1 AYPUNJXVHMPYJH-UHFFFAOYSA-N 0.000 description 1
- KHBBRIBQJGWUOW-UHFFFAOYSA-N 2-methylcyclohexane-1,3-diamine Chemical compound CC1C(N)CCCC1N KHBBRIBQJGWUOW-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- ULMZOZMSDIOZAF-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)propanoic acid Chemical compound OCC(CO)C(O)=O ULMZOZMSDIOZAF-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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Classifications
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- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- 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
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- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- 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
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- 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
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- 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
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- 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
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- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
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- 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
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- 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
- C08G18/48—Polyethers
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- 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
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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- 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
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- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
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- 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
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- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- 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
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- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
-
- 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
-
- 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
-
- 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
- C09D175/02—Polyureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996107853 DE19607853A1 (de) | 1996-03-01 | 1996-03-01 | In Wasser lösliche oder dispergierbare Polyharnstoffe, ein Verfahren zu deren Herstellung und ihre Verwendung zur Beschichtung beliebiger Substrate |
| DE19611850.6 | 1996-03-26 | ||
| DE19611850A DE19611850A1 (de) | 1996-03-26 | 1996-03-26 | Verwendung von ionischen und nichtionischen wäßrigen Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan als Bindemittel für Glasfaserschlichten sowie spezielle ionische und nichtionische wäßrige Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan |
| DE19607853.9 | 1996-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09241347A true JPH09241347A (ja) | 1997-09-16 |
Family
ID=26023372
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9057130A Pending JPH09241347A (ja) | 1996-03-01 | 1997-02-26 | 水性ポリウレタン−ウレア、その調製方法、及び塗料におけるその使用 |
| JP05858597A Expired - Fee Related JP3844840B2 (ja) | 1996-03-01 | 1997-02-27 | １−メチル−２，４−及び／又は−２，６−ジイソシアナトシクロヘキサンをベースとする水性ポリウレタン分散液及びガラス繊維サイズ用結合剤としてのその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05858597A Expired - Fee Related JP3844840B2 (ja) | 1996-03-01 | 1997-02-27 | １−メチル−２，４−及び／又は−２，６−ジイソシアナトシクロヘキサンをベースとする水性ポリウレタン分散液及びガラス繊維サイズ用結合剤としてのその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5804647A (enExample) |
| EP (2) | EP0792899B1 (enExample) |
| JP (2) | JPH09241347A (enExample) |
| KR (1) | KR100468548B1 (enExample) |
| BR (1) | BR9701138A (enExample) |
| CA (2) | CA2198445A1 (enExample) |
| DE (2) | DE59709939D1 (enExample) |
| ES (2) | ES2197959T3 (enExample) |
| MX (1) | MX9701566A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000034331A (ja) * | 1998-06-02 | 2000-02-02 | Bayer Ag | 改善された貯蔵安定性をもつ高固形分ポリウレタン―尿素分散液 |
| JP2007125889A (ja) * | 2005-11-02 | 2007-05-24 | Bayer Material Science Llc | 複合品およびその製造法 |
| JP2011505434A (ja) * | 2007-11-13 | 2011-02-24 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 非イオン的親水化結合剤分散体 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19731864A1 (de) * | 1997-07-24 | 1999-01-28 | Bayer Ag | Wäßrige PUR-Dispersionen mit verbesserten Eigenschaften |
| US6325887B1 (en) | 1998-04-30 | 2001-12-04 | Morton International, Inc. | Heat-activatable polyurethane/urea adhesive in aqueous dispersion |
| DE19914882A1 (de) † | 1999-04-01 | 2000-10-05 | Bayer Ag | Selbstvernetzende Polyurethan-, Polyurethan-Polyharnstoff- bzw. Polyharnstoff-Dispersionen für Schlichten |
| DE10056183A1 (de) * | 2000-11-13 | 2002-05-29 | Basf Ag | Hochverzweigte Polymere zur Antiknitterausrüstung von cellulosehaltigen Textilien |
| DE10133789A1 (de) * | 2001-07-16 | 2003-02-06 | Basf Ag | Wässrige Dispersionen für hydrolysefeste Beschichtungen |
| GB0207351D0 (en) | 2002-03-28 | 2002-05-08 | Avecia Bv | Aqueous coating composition |
| DE10226933A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Glasfaserverstärkte Kunststoffe |
| US6784243B2 (en) | 2002-06-17 | 2004-08-31 | Bayer Aktiengesellschaft | Polyurethane-polyurea dispersions |
| GB0300225D0 (en) * | 2003-01-04 | 2003-02-05 | Neoresins Inc | Aqueous polyurethane coating composition |
| DE10315175A1 (de) * | 2003-04-03 | 2004-10-14 | Degussa Construction Chemicals Gmbh | Elektrosterisch stabilisierte wässrige Polyurethan-Harze, Verfahren zu ihrer Herstellung und deren Verwendung |
| GB0320994D0 (en) * | 2003-09-09 | 2003-10-08 | Avecia Bv | Aqueous polymer compositions |
| DE102004002527A1 (de) * | 2004-01-16 | 2005-08-04 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| DE102005018692A1 (de) * | 2005-04-22 | 2006-10-26 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| WO2007027921A1 (en) | 2005-09-02 | 2007-03-08 | Dow Global Technologies Inc. | Solvent free polyurethane dispersions for hard surface coatings |
| DE102006046649A1 (de) * | 2006-09-29 | 2008-04-03 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| DE102007023319A1 (de) * | 2007-05-16 | 2008-11-20 | Bayer Materialscience Ag | Aufgesäuerte Polyesterpolyurethan-Dispersion |
| US20130022746A9 (en) * | 2007-12-10 | 2013-01-24 | Harry Joseph Spinelli | Aqueous inkjet inks with ionically stabilized dispersions and polyurethane ink additives |
| US9410010B2 (en) | 2007-12-10 | 2016-08-09 | E I Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| US20100093927A1 (en) * | 2007-12-10 | 2010-04-15 | Roberts C Chad | Polyurethanes with Nonionic Hydrophilic Terminating Groups and Aqueous Dispersions Thereof |
| US20110039028A1 (en) * | 2008-05-23 | 2011-02-17 | E,I. Du Pont De Nemours And Company | Inkjet ink with self dispersed pigments and polyurethane ink additives |
| WO2009143441A1 (en) | 2008-05-23 | 2009-11-26 | E. I. Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| US20110045219A1 (en) * | 2009-08-18 | 2011-02-24 | Bayer Materialscience Llc | Coating compositions for glass substrates |
| US9868862B2 (en) | 2011-05-25 | 2018-01-16 | Diversey, Inc. | Surface coating system and method of using surface coating system |
| EP2877509B1 (en) * | 2012-07-26 | 2018-11-21 | Covestro Deutschland AG | Aqueous polyurethane dispersion comprising a terephthalic acid polyester |
| JP7241487B2 (ja) | 2017-09-25 | 2023-03-17 | エボニック オペレーションズ ゲーエムベーハー | ポリウレタン系の製造 |
| JP7289975B1 (ja) * | 2022-08-08 | 2023-06-12 | 第一工業製薬株式会社 | 繊維集束剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3339580A1 (de) * | 1983-11-02 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Waessrige dispersionen vernetzer-haltiger lackbindemittel auf polyesterbasis |
| DE3412611A1 (de) * | 1984-04-04 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | Waessrige dispersionen auf polyesterbasis, ihre herstellung und ihre verwendung zur herstellung von einbrennlacken |
| US5194487A (en) * | 1991-01-22 | 1993-03-16 | Miles Inc. | Two-component aqueous polyurethane dispersions with reduced solvent content and coatings prepared therefrom with improved gloss |
| US5212230A (en) * | 1991-03-28 | 1993-05-18 | Miles Inc. | Aqueous polyurea dispersions prepared by an emulsion polymerization process |
| US5185200A (en) * | 1991-03-28 | 1993-02-09 | Miles Inc. | Aqueous polyisocyanate dispersions with reduced isocyanate contents and their use for the production of fiberglass mats |
| US5157074A (en) * | 1991-07-23 | 1992-10-20 | Miles Inc. | Aqueous compositions containing an at least partially blocked polyisocyanates and a trimerization catalyst and coatings and binders prepared therefrom |
| DE19506736A1 (de) * | 1995-02-27 | 1996-08-29 | Bayer Ag | Wäßrige Bindemittel auf Polyester-Polyurethan-Basis |
| DE19517185A1 (de) * | 1995-05-11 | 1996-11-14 | Bayer Ag | Biologisch abbaubare und kompostierbare Formkörper einschließlich Flächengebilden |
-
1997
- 1997-02-17 ES ES97102544T patent/ES2197959T3/es not_active Expired - Lifetime
- 1997-02-17 DE DE59709939T patent/DE59709939D1/de not_active Expired - Lifetime
- 1997-02-17 EP EP97102544A patent/EP0792899B1/de not_active Expired - Lifetime
- 1997-02-21 US US08/804,462 patent/US5804647A/en not_active Expired - Lifetime
- 1997-02-25 CA CA002198445A patent/CA2198445A1/en not_active Abandoned
- 1997-02-26 ES ES97103058T patent/ES2208777T3/es not_active Expired - Lifetime
- 1997-02-26 JP JP9057130A patent/JPH09241347A/ja active Pending
- 1997-02-26 EP EP97103058A patent/EP0792900B1/de not_active Expired - Lifetime
- 1997-02-26 CA CA002198567A patent/CA2198567A1/en not_active Abandoned
- 1997-02-26 DE DE59710872T patent/DE59710872D1/de not_active Expired - Lifetime
- 1997-02-27 JP JP05858597A patent/JP3844840B2/ja not_active Expired - Fee Related
- 1997-02-27 KR KR1019970006273A patent/KR100468548B1/ko not_active Expired - Fee Related
- 1997-02-28 MX MX9701566A patent/MX9701566A/es unknown
- 1997-02-28 BR BR9701138A patent/BR9701138A/pt not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000034331A (ja) * | 1998-06-02 | 2000-02-02 | Bayer Ag | 改善された貯蔵安定性をもつ高固形分ポリウレタン―尿素分散液 |
| JP2007125889A (ja) * | 2005-11-02 | 2007-05-24 | Bayer Material Science Llc | 複合品およびその製造法 |
| JP2011505434A (ja) * | 2007-11-13 | 2011-02-24 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 非イオン的親水化結合剤分散体 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9701138A (pt) | 1998-12-15 |
| KR970065581A (ko) | 1997-10-13 |
| KR100468548B1 (ko) | 2005-09-26 |
| ES2208777T3 (es) | 2004-06-16 |
| DE59710872D1 (de) | 2003-11-27 |
| MX9701566A (es) | 1998-04-30 |
| US5804647A (en) | 1998-09-08 |
| ES2197959T3 (es) | 2004-01-16 |
| DE59709939D1 (de) | 2003-06-05 |
| CA2198567A1 (en) | 1997-09-01 |
| JPH09241348A (ja) | 1997-09-16 |
| EP0792900A1 (de) | 1997-09-03 |
| EP0792899A1 (de) | 1997-09-03 |
| EP0792900B1 (de) | 2003-10-22 |
| CA2198445A1 (en) | 1997-09-01 |
| JP3844840B2 (ja) | 2006-11-15 |
| EP0792899B1 (de) | 2003-05-02 |
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