CA2364603C - Self-crosslinking polyurethane, polyurethane-polyurea or polyurea dispersions for sizing materials - Google Patents
Self-crosslinking polyurethane, polyurethane-polyurea or polyurea dispersions for sizing materials Download PDFInfo
- Publication number
- CA2364603C CA2364603C CA002364603A CA2364603A CA2364603C CA 2364603 C CA2364603 C CA 2364603C CA 002364603 A CA002364603 A CA 002364603A CA 2364603 A CA2364603 A CA 2364603A CA 2364603 C CA2364603 C CA 2364603C
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- Canada
- Prior art keywords
- component
- dispersion
- reactive
- isocyanate groups
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000006185 dispersion Substances 0.000 title claims abstract description 145
- 238000004132 cross linking Methods 0.000 title claims abstract description 42
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 36
- 239000004814 polyurethane Substances 0.000 title claims abstract description 18
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 16
- 238000004513 sizing Methods 0.000 title claims 2
- 239000000463 material Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 125000003277 amino group Chemical group 0.000 claims description 35
- 229920000570 polyether Polymers 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 27
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229920005862 polyol Polymers 0.000 claims description 24
- 150000003077 polyols Chemical class 0.000 claims description 24
- 239000002981 blocking agent Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000003365 glass fiber Substances 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 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 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- 150000002009 diols Chemical class 0.000 claims description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001449 anionic compounds Chemical class 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- 239000004970 Chain extender Substances 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920000909 polytetrahydrofuran Polymers 0.000 claims 1
- 239000000306 component Substances 0.000 description 95
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- -1 ethylene glycol Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 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
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 229920003009 polyurethane dispersion Polymers 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 4
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940031098 ethanolamine Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
- 229940043276 diisopropanolamine Drugs 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 description 2
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 2
- NRESEGNWLZRQBR-UHFFFAOYSA-N 3-methylheptane-2,2-diamine Chemical compound CCCCC(C)C(C)(N)N NRESEGNWLZRQBR-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- AXPMRSNNJUSOPB-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylcyclohexyl)methyl]-2,6-diethylcyclohexan-1-amine Chemical compound C1C(CC)C(N)C(CC)CC1CC1CC(CC)C(N)C(CC)C1 AXPMRSNNJUSOPB-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
- GLBHAWAMATUOBB-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diamine Chemical compound CC(C)(C)CCCCC(N)N GLBHAWAMATUOBB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010422 painting Methods 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
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ROAIHDOATZBRFC-UHFFFAOYSA-N 1,2-diisocyanato-1,2-dimethylcyclohexane Chemical group O=C=NC1(C)CCCCC1(C)N=C=O ROAIHDOATZBRFC-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- WAWYSJFTGINOCE-UHFFFAOYSA-N 1-(2-aminoethylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NCCN WAWYSJFTGINOCE-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-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
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8074—Lactams
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2938—Coating on discrete and individual rods, strands or filaments
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914882.1 | 1999-04-01 | ||
| DE19914882A DE19914882A1 (de) | 1999-04-01 | 1999-04-01 | Selbstvernetzende Polyurethan-, Polyurethan-Polyharnstoff- bzw. Polyharnstoff-Dispersionen für Schlichten |
| PCT/EP2000/002486 WO2000059973A1 (de) | 1999-04-01 | 2000-03-21 | Selbstvernetzende polyurethan-, polyurethan-polyharnstoff- bzw. polyharnstoff-dispersionen für schlichten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2364603A1 CA2364603A1 (en) | 2000-10-12 |
| CA2364603C true CA2364603C (en) | 2009-12-22 |
Family
ID=7903257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002364603A Expired - Fee Related CA2364603C (en) | 1999-04-01 | 2000-03-21 | Self-crosslinking polyurethane, polyurethane-polyurea or polyurea dispersions for sizing materials |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6586523B1 (enExample) |
| EP (1) | EP1169369B2 (enExample) |
| JP (1) | JP4740460B2 (enExample) |
| KR (1) | KR100642177B1 (enExample) |
| CN (1) | CN1345344A (enExample) |
| AT (1) | ATE252117T1 (enExample) |
| AU (1) | AU3963200A (enExample) |
| BR (1) | BR0009500A (enExample) |
| CA (1) | CA2364603C (enExample) |
| CZ (1) | CZ20013530A3 (enExample) |
| DE (2) | DE19914882A1 (enExample) |
| ES (1) | ES2208302T5 (enExample) |
| HK (1) | HK1045702A1 (enExample) |
| MX (1) | MXPA01009822A (enExample) |
| PL (1) | PL350997A1 (enExample) |
| RU (1) | RU2252942C2 (enExample) |
| TR (1) | TR200102774T2 (enExample) |
| TW (1) | TWI228515B (enExample) |
| UA (1) | UA73734C2 (enExample) |
| WO (1) | WO2000059973A1 (enExample) |
Families Citing this family (64)
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|---|---|---|---|---|
| DE10147546B4 (de) * | 2001-09-26 | 2006-04-13 | Basf Coatings Ag | Polyurethan, Verfahren zu seiner Herstellung und seine Verwendung |
| DE10216945A1 (de) | 2002-04-17 | 2003-11-06 | Bayer Ag | Selbstvernetzende PUR-Dispersionen |
| DE10226933A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Glasfaserverstärkte Kunststoffe |
| DE10306243A1 (de) * | 2003-02-14 | 2004-08-26 | Bayer Ag | Einkomponenten-Beschichtungssysteme |
| US6989429B2 (en) * | 2003-10-02 | 2006-01-24 | Tremco Incorporated | Prepolymer compositions and sealants made therefrom |
| CN2689322Y (zh) * | 2004-02-28 | 2005-03-30 | 鸿富锦精密工业（深圳）有限公司 | 主机板固定装置 |
| US20070072989A1 (en) * | 2004-03-19 | 2007-03-29 | Piret Willy H | Two-part sizing composition for reinforcement fibers |
| US20050228121A1 (en) * | 2004-04-01 | 2005-10-13 | Ziegler Michael J | Oligomer suitable for coating compositions for wood substrates |
| WO2006047746A1 (en) * | 2004-10-26 | 2006-05-04 | Noveon, Inc. | Water-borne dispersions of oil modified urethane polymers |
| US7240371B2 (en) | 2005-02-11 | 2007-07-10 | Invista North America S.A.R.L. | Solvent free aqueous polyurethane dispersions and adhesive films therefrom for stretch fabrics |
| US20080004395A1 (en) * | 2005-02-11 | 2008-01-03 | Invista North America S.A.R.L. | Aqueous polyurethaneurea compositions including dispersions and films |
| US20060183850A1 (en) * | 2005-02-11 | 2006-08-17 | Invista North America S.A.R.L. | Solvent free aqueous polyurethane dispersions and shaped articles therefrom |
| ATE430771T1 (de) | 2005-03-24 | 2009-05-15 | Medtronic Inc | Modifizierung von thermoplastischen polymeren |
| DE102005018692A1 (de) * | 2005-04-22 | 2006-10-26 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| US20070256789A1 (en) * | 2005-06-24 | 2007-11-08 | Invista North Americal S.A.R.L. | Guide for bonding tapes or films |
| US8389653B2 (en) * | 2006-03-30 | 2013-03-05 | Basf Corporation | Method of catalyzing a reaction to form a urethane coating and a complex for use in the method |
| DE102006025313A1 (de) * | 2006-05-31 | 2007-12-06 | Bayer Materialscience Ag | Lösemittelarme oder lösemittelfreie Vernetzer-Dispersion mit Pyrazol-blockierten Isocyanatgruppen |
| JP4797843B2 (ja) * | 2006-07-11 | 2011-10-19 | コニカミノルタエムジー株式会社 | 圧電性合成樹脂膜の形成方法 |
| DE102006052240A1 (de) * | 2006-11-03 | 2008-05-08 | Bayer Materialscience Ag | Lösungen blockierter Polyimide bzw. Polyamidimide |
| KR100860009B1 (ko) * | 2006-12-13 | 2008-09-25 | (주)아텍스 | 고부착력의 폴리우레아 코팅제의 제조방법 및 폴리우레아의 코팅방법 |
| DE102006059680A1 (de) * | 2006-12-18 | 2008-06-19 | Bayer Materialscience Ag | Colöserfreie, selbstvernetzende PUR-Dispersionen |
| US20080160281A1 (en) * | 2006-12-29 | 2008-07-03 | Vickery Eric L | Sizing composition for glass fibers |
| DE102007023319A1 (de) * | 2007-05-16 | 2008-11-20 | Bayer Materialscience Ag | Aufgesäuerte Polyesterpolyurethan-Dispersion |
| CL2008003124A1 (es) * | 2007-11-07 | 2009-11-27 | Bayer Materialscience Ag | Dispersiones acuosas de poliuretano-urea acuosa de; poliol(es) difuncional (es) o funcionalidad superior, compuestos(s) monofuncional (es) con la menos 50% p/p de óxido de etileno, componente(s)di o poliiocianato; y mezcla de compuestos monoamina primarios y/o secundarios; procedimiento; uso; composición; y compuesto adhesivo. |
| DE102007054002A1 (de) * | 2007-11-13 | 2009-05-14 | Bayer Materialscience Ag | Nicht-ionisch hydrophilierte Bindemittel-Dispersionen |
| EP2103316A1 (de) | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Hydrophile Polyurethandispersionen |
| EP2103638A1 (de) * | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Hydrophile Polyurethanlösungen |
| EP2103318A1 (de) * | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Medizinische Geräte mit hydrophilen Beschichtungen |
| EP2103317A1 (de) * | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Medizinische Geräte mit hydrophilen Beschichtungen |
| DE102008025613A1 (de) | 2008-05-28 | 2009-12-03 | Bayer Materialscience Ag | Hydrophile Polyurethanbeschichtungen |
| NZ587326A (en) * | 2008-05-28 | 2012-07-27 | Clariant Finance Bvi Ltd | Aqueous polyurethane-polyurea dispersions |
| DE102008025614A1 (de) * | 2008-05-28 | 2009-12-03 | Bayer Materialscience Ag | Hydrophile Polyurethanbeschichtungen |
| US8791200B2 (en) | 2008-09-04 | 2014-07-29 | Bayer Materialscience Ag | TCD based hydrophilic polyurethane dispersions |
| DK2331596T3 (da) * | 2008-09-04 | 2012-05-29 | Bayer Materialscience Ag | TCD baserede hyddrofile polyurethadispersioner |
| MX2011003996A (es) * | 2008-10-17 | 2011-05-10 | Invista Tech Sarl | Composiciones acuosas de poliuretanourea que incluyen dispersiones y peliculas. |
| EP2186841A1 (de) * | 2008-11-14 | 2010-05-19 | Bayer MaterialScience AG | Vernetzbare Polyurethan-Dispersionen |
| EP2221330A1 (de) | 2009-02-19 | 2010-08-25 | Bayer MaterialScience AG | Funktionalisierte Polyurethanpolyharnstoff-Dispersionen |
| EP2298825A1 (de) | 2009-09-17 | 2011-03-23 | Bayer MaterialScience AG | Hydrophile Polyurethanharnstoffdispersionen |
| US9617453B2 (en) | 2009-12-14 | 2017-04-11 | Air Products And Chemicals, Inc. | Solvent free aqueous polyurethane dispersions and methods of making and using the same |
| KR101225580B1 (ko) * | 2010-07-19 | 2013-01-24 | 애경화학 주식회사 | 사이즈제용 수성 폴리우레탄 분산액 및 그 제조방법, 및 이를 포함하는 유리섬유 사이즈제 |
| JP6106515B2 (ja) * | 2012-05-09 | 2017-04-05 | 第一工業製薬株式会社 | ガラス繊維用集束剤 |
| US9587139B2 (en) | 2012-06-15 | 2017-03-07 | 3M Innovative Properties Company | Curable polyurea forming composition, method of making, and composite article |
| US10907005B2 (en) * | 2012-09-25 | 2021-02-02 | Battelle Memorial Institute | Aqueous prepolymer dispersions |
| KR101368339B1 (ko) | 2013-07-26 | 2014-02-28 | 설태윤 | 작업성 및 설비조작성이 우수한 신발갑피용 1액형 폴리우레아 수지 조성물 |
| CN103696321A (zh) * | 2013-12-20 | 2014-04-02 | 天津商业大学 | 一种复合表面施胶剂的制备方法 |
| US10793672B2 (en) | 2014-06-11 | 2020-10-06 | Battelle Memorial Institute | Alkoxylated bio-oil polyol compositions |
| RU2690360C2 (ru) * | 2014-09-19 | 2019-05-31 | Санио Кемикал Индастриз, Лтд. | Композиция проклеивающего средства для волокна, дисперсия проклеивающего средства для волокна, раствор проклеивающего средства для волокна, способ для производства пучков волокон, композитный промежуточный материал и армированный волокном композиционный материал |
| US10836927B2 (en) * | 2014-12-09 | 2020-11-17 | Basf Coatings Gmbh | Aqueous polyurethane-polyurea dispersion and aqueous base paint containing said dispersion |
| CN105968285A (zh) * | 2016-06-02 | 2016-09-28 | 深圳市深赛尔股份有限公司 | 一种水性硅烷聚脲树脂及其制备方法 |
| EP3500609B1 (en) | 2016-08-17 | 2020-12-30 | The LYCRA Company UK Limited | Aqueous polyurethane dispersions, prepolymers, and shaped articles made therefrom |
| CN109134804B (zh) * | 2016-12-19 | 2021-10-22 | 科思创德国股份有限公司 | 聚氨酯水性分散体 |
| CN107267050A (zh) * | 2017-07-27 | 2017-10-20 | 上海展辰涂料有限公司 | 一种水性木器双组分亮光调色浅色面漆的发明 |
| WO2019089516A1 (en) | 2017-11-03 | 2019-05-09 | A&At Llc | Methods for use of aqueous polyurethane dispersions and articles made thereby |
| CN107936212B (zh) * | 2017-11-29 | 2020-12-18 | 广州冠志新材料科技有限公司 | 指甲油用水性聚氨酯树脂及其制备方法 |
| WO2019190997A1 (en) * | 2018-03-27 | 2019-10-03 | Advansix Resins & Chemicals Llc | Thixotropic rheology modifying agent compositions |
| US12441918B2 (en) * | 2019-09-27 | 2025-10-14 | Lg Chem, Ltd. | Adhesive composition, and polarizing plate and display device manufactured using same |
| CN113718534B (zh) * | 2020-05-25 | 2023-09-15 | 中国石油化工股份有限公司 | 一种防爆抗冲击纤维增强聚脲复合材料及其制备方法和应用 |
| WO2022107811A1 (en) * | 2020-11-19 | 2022-05-27 | Japan Fine Coatings Co., Ltd. | Composition for forming coating layer of optical fiber and cured layer thereof, optical fiber having cured layer, and use thereof |
| JP7716208B2 (ja) * | 2020-11-19 | 2025-07-31 | 日本特殊コーティング株式会社 | 光ファイバ被覆層形成用組成物及びその硬化層、並びに硬化層を有する光ファイバ及び光ファイバ被覆層形成用組成物の使用 |
| CN116601201A (zh) | 2020-12-08 | 2023-08-15 | 科思创德国股份有限公司 | 水性聚氨酯脲分散体 |
| EP4029894A1 (en) | 2021-01-15 | 2022-07-20 | Covestro Deutschland AG | Aqueous polyurethane urea dispersion |
| EP4112670A1 (de) * | 2021-07-01 | 2023-01-04 | Covestro Deutschland AG | Nicht-ionisch hydrophilierte polyurethan-dispersionen mit acrylat-doppelbindungen |
| EP4112669A1 (de) * | 2021-07-01 | 2023-01-04 | Covestro Deutschland AG | Nicht-ionisch hydrophilierte polyurethan-dispersionen mit methacrylat-doppelbindungen |
| WO2025108924A1 (en) * | 2023-11-21 | 2025-05-30 | Covestro Deutschland Ag | Water-dispersible blocked isocyanate prepolymer system, method for preparing the same, and application thereof |
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| US4108814A (en) | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
| DE2553839C3 (de) * | 1975-05-22 | 1978-11-23 | Bayer Ag, 5090 Leverkusen | Beschlichtete Glasfasern |
| US4255317A (en) | 1978-11-20 | 1981-03-10 | Owens-Corning Fiberglas Corporation | Non-discoloring glass strand size |
| US4310646A (en) * | 1979-04-09 | 1982-01-12 | Basf Aktiengesellschaft | Self-crosslinking cationic binders and their preparation |
| DE3015143A1 (de) * | 1979-04-30 | 1980-11-06 | Grace W R & Co | Polyurethanpolymere in waessrigem medium und verfahren zu deren herstellung |
| US4387181A (en) | 1980-04-09 | 1983-06-07 | Textron, Inc. | Polymer compositions and manufacture |
| DE3641494A1 (de) * | 1986-12-04 | 1988-06-09 | Bayer Ag | In wasser loesliche oder dispergierbare poylurethane, ein verfahren zu ihrer herstellung und ihre verwendung zur beschichtung beliebiger substrate |
| JPH04325510A (ja) * | 1991-04-26 | 1992-11-13 | Dainippon Ink & Chem Inc | 接着剤 |
| CA2072931C (en) | 1991-07-23 | 2003-12-30 | Robin E. Tirpak | A process for the preparation of aqueous dispersions containing both blocked polyisocyanates and polyhydroxyl compounds |
| DE4142734A1 (de) † | 1991-12-21 | 1993-06-24 | Hoechst Ag | Wasserverduennbares, urethanmodifiziertes und hydroxylgruppen enthaltendes selbstvernetzendes bindemittel und zubereitungen davon |
| DE4218184A1 (de) | 1992-06-02 | 1993-12-09 | Bayer Ag | Wäßriges Bindemittelgemisch und seine Verwendung |
| JP3205786B2 (ja) * | 1992-08-18 | 2001-09-04 | 関西ペイント株式会社 | 自己架橋性樹脂 |
| US5574083A (en) * | 1993-06-11 | 1996-11-12 | Rohm And Haas Company | Aromatic polycarbodiimide crosslinkers |
| DE19548030A1 (de) * | 1995-12-21 | 1997-06-26 | Bayer Ag | Verwendung wässriger Dispersionen nachvernetzbarer Beschichtungsmittel zur Textil- und Lederbeschichtung |
| EP0792899B1 (de) † | 1996-03-01 | 2003-05-02 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyurethanharnstoffe, ein Verfahren zu deren Herstellung und ihre Verwendung zur Beschichtung beliebiger Substrate |
| DE19611850A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | 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 |
| JP3783283B2 (ja) * | 1996-05-14 | 2006-06-07 | 日東紡績株式会社 | ガラス繊維用集束剤 |
| WO1998002494A1 (fr) * | 1996-07-12 | 1998-01-22 | Kansai Paint Company, Limited | Composition d'electrodeposition cationique de revetement |
| DE19822631A1 (de) † | 1998-05-20 | 1999-11-25 | Basf Coatings Ag | Beschichtungsmittel, die geblockte Polyurethanprepolymere enthalten, und deren Verwendung |
| JP2002506414A (ja) * | 1998-06-04 | 2002-02-26 | オウェンス コーニング コンポジッツ エスピーアールエル | 繊維用の高溶解度サイズ剤組成物 |
-
1999
- 1999-04-01 DE DE19914882A patent/DE19914882A1/de not_active Withdrawn
-
2000
- 2000-03-21 WO PCT/EP2000/002486 patent/WO2000059973A1/de not_active Ceased
- 2000-03-21 US US09/937,835 patent/US6586523B1/en not_active Expired - Lifetime
- 2000-03-21 EP EP00918820A patent/EP1169369B2/de not_active Expired - Lifetime
- 2000-03-21 AT AT00918820T patent/ATE252117T1/de not_active IP Right Cessation
- 2000-03-21 HK HK02107369.6A patent/HK1045702A1/zh unknown
- 2000-03-21 CZ CZ20013530A patent/CZ20013530A3/cs unknown
- 2000-03-21 JP JP2000609478A patent/JP4740460B2/ja not_active Expired - Fee Related
- 2000-03-21 TR TR2001/02774T patent/TR200102774T2/xx unknown
- 2000-03-21 RU RU2001129498/04A patent/RU2252942C2/ru not_active IP Right Cessation
- 2000-03-21 BR BR0009500-1A patent/BR0009500A/pt not_active IP Right Cessation
- 2000-03-21 KR KR1020017012405A patent/KR100642177B1/ko not_active Expired - Fee Related
- 2000-03-21 UA UA2001107428A patent/UA73734C2/uk unknown
- 2000-03-21 ES ES00918820T patent/ES2208302T5/es not_active Expired - Lifetime
- 2000-03-21 DE DE50004081T patent/DE50004081D1/de not_active Expired - Lifetime
- 2000-03-21 AU AU39632/00A patent/AU3963200A/en not_active Abandoned
- 2000-03-21 PL PL00350997A patent/PL350997A1/xx not_active Application Discontinuation
- 2000-03-21 CA CA002364603A patent/CA2364603C/en not_active Expired - Fee Related
- 2000-03-21 CN CN00805504A patent/CN1345344A/zh active Pending
- 2000-03-21 MX MXPA01009822A patent/MXPA01009822A/es unknown
- 2000-03-30 TW TW089105876A patent/TWI228515B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1169369A1 (de) | 2002-01-09 |
| EP1169369B2 (de) | 2006-05-17 |
| TWI228515B (en) | 2005-03-01 |
| PL350997A1 (en) | 2003-02-24 |
| JP2002541280A (ja) | 2002-12-03 |
| CZ20013530A3 (cs) | 2002-01-16 |
| UA73734C2 (en) | 2005-09-15 |
| KR20020027303A (ko) | 2002-04-13 |
| ES2208302T5 (es) | 2007-02-01 |
| JP4740460B2 (ja) | 2011-08-03 |
| US6586523B1 (en) | 2003-07-01 |
| ES2208302T3 (es) | 2004-06-16 |
| WO2000059973A1 (de) | 2000-10-12 |
| BR0009500A (pt) | 2002-01-15 |
| DE50004081D1 (de) | 2003-11-20 |
| CA2364603A1 (en) | 2000-10-12 |
| CN1345344A (zh) | 2002-04-17 |
| KR100642177B1 (ko) | 2006-11-10 |
| MXPA01009822A (es) | 2002-06-21 |
| RU2252942C2 (ru) | 2005-05-27 |
| ATE252117T1 (de) | 2003-11-15 |
| HK1045702A1 (zh) | 2002-12-06 |
| DE19914882A1 (de) | 2000-10-05 |
| EP1169369B1 (de) | 2003-10-15 |
| AU3963200A (en) | 2000-10-23 |
| TR200102774T2 (tr) | 2002-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150323 |