JP2018532830A - 改善された特性を有する水乳化性イソシアネート - Google Patents
改善された特性を有する水乳化性イソシアネート Download PDFInfo
- Publication number
- JP2018532830A JP2018532830A JP2018512260A JP2018512260A JP2018532830A JP 2018532830 A JP2018532830 A JP 2018532830A JP 2018512260 A JP2018512260 A JP 2018512260A JP 2018512260 A JP2018512260 A JP 2018512260A JP 2018532830 A JP2018532830 A JP 2018532830A
- Authority
- JP
- Japan
- Prior art keywords
- group
- polyisocyanate
- acid
- mixture
- water
- 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.)
- Granted
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 46
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 34
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 144
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 144
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 13
- -1 polyethylene Polymers 0.000 claims description 40
- 238000000576 coating method Methods 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 23
- 239000004815 dispersion polymer Substances 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 229920005862 polyol Polymers 0.000 claims description 17
- 150000003077 polyols Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 10
- 125000003010 ionic group Chemical group 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- 229920000058 polyacrylate Polymers 0.000 claims description 8
- 229920001281 polyalkylene Polymers 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 125000005442 diisocyanate group Chemical group 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000005058 Isophorone diisocyanate Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 239000002253 acid Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 9
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000002596 lactones Chemical class 0.000 description 8
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 7
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 7
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 6
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 6
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 4
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Chemical compound CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 3
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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- 230000004048 modification Effects 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 2
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 2
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- CCNSVURUCGIWPV-UHFFFAOYSA-N 2,4-diethyloctane-1,3-diol Chemical compound CCCCC(CC)C(O)C(CC)CO CCNSVURUCGIWPV-UHFFFAOYSA-N 0.000 description 2
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- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- HYFFNAVAMIJUIP-UHFFFAOYSA-N 2-ethylpropane-1,3-diol Chemical compound CCC(CO)CO HYFFNAVAMIJUIP-UHFFFAOYSA-N 0.000 description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical class COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
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- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 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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- C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
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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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- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate 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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- C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
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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
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- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the 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
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- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
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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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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- 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
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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Abstract
Description
a)少なくとも1つのポリイソシアネート、
b)少なくとも1つのポリイソシアネートb1)と、イソシアネートに対して反応性ではない少なくとも1つの親水性の基(基A)及びイソシアネートに対して反応性のある正確に1つの基(基B)を有する少なくとも1つの化合物b2)との、少なくとも1つの反応生成物、並びに
c)ジオキソラン
を含む混合物に関する。
少なくとも1つのポリイソシアネートの平均NCO官能価は、一般に少なくとも1.8であり、8まで、例えば6まで、好ましくは2から5まで、特に好ましくは2.4から4までであってよい。
1) 芳香族ジイソシアネート、脂肪族ジイソシアネート及び/又は脂環式ジイソシアネートから誘導される1つ以上のイソシアヌレート基含有ポリイソシアネート。特に好ましくは、相応する脂肪族イソシアネートイソシアヌレート及び/又は脂環式イソシアネートイソシアヌレート、殊にヘキサメチレンジイソシアネート及びイソホロンジイソシアネートに基づくものである。ここで存在するイソシアヌレートは、殊に、ジイソシアネートの環状三量体であるトリス−イソシアネートアルキルもしくはトリス−イソシアネートシクロアルキルイソシアヌレート、又はより高級な1を超えるイソシアヌレート環を含むそれらの同族体との混合物である。イソシアネートイソシアヌレートは、一般にNCO含有量10〜30質量%、殊に15〜25質量%、及び平均NCO官能価2.6〜8を有する。イソシアヌレート基含有ポリイソシアネートは、ウレタン基及び/又はアロファネート基を少量で、好ましくはポリイソシアネートに対して2質量%未満の結合したアルコールの含有量で有してよい。
シュウ酸、マレイン酸、フマル酸、コハク酸、グルタル酸、アジピン酸、セバシン酸、ドデカン二酸、o−フタル酸、イソフタル酸、テレフタル酸、トリメリト酸、アゼライン酸、1,4−シクロヘキサンジカルボン酸又はトラヒドロフタル酸、コルク酸、アゼライン酸、フタル酸無水物、テトラヒドロフタル酸無水物、ヘキサヒドロフタル酸無水物、テトラヒドロフタル酸無水物、エンドメチレンテトラヒドロフタル酸無水物、グルタル酸無水物、マレイン酸無水物、二量体脂肪酸、それらの異性体及び水素化生成物、並びに前記酸のエステル化可能な誘導体、例えば無水物又はジアルキルエステル、例えばC1〜C4−アルキルエステル、好ましくはメチルエステル、エチルエステルもしくはn−ブチルエステル。一般式HOOC−(CH2)y−COOH [式中、yは1〜20の数であり、好ましくは2〜20の偶数である]のジカルボン酸が好ましく、コハク酸、アジピン酸、セバシン酸、及びドデカンジカルボン酸が特に好ましい。
水分散性ポリイソシアネート1:
NCO含有量22.2%及び23℃での粘度2800mPa*sを有するHDIイソシアヌレート(BASF SE(Ludwigshafen)からBasonat(登録商標)HI 100として市販されている)100gと、メタノールから出発し、水酸化カリウム触媒下で製造されるOH価112(DIN 53240による)及び分子量500g/molを有する一官能性ポリエチレンオキシド15gとを混合し、加熱し、そして互いに反応させた。90℃で3時間後に、その反応を、示されたNCO含有量に達した時点で停止させたが、これはウレタンの完全な形成に相応した。相応する生成物は、23℃での粘度2600mPa*s及びNCO含有量17.9%を有した。
文献国際公開第2001/88006号に記載されるように、NCO含有量22.2%及び23℃で粘度2800mPa*sを有するHDIイソシアヌレート(BASF SE(Ludwigshafen)からBasonat(登録商標)HI 100として市販されている)237.5gと、ジメチルシクロヘキシルアミン(BASF SE)5.8gと、3−(シクロヘキシルアミノ)−1−プロパンスルホン酸10gとを混合した。80℃で3時間後に、その反応を、示されたNCO含有量に達した時点で停止させたが、これは尿素の完全な形成に相応した。相応する生成物は、23℃での粘度13300mPa*s及びNCO含有量19.3%を有した。
水分散性ポリイソシアネート1及び2を、さらに種々の溶媒で希釈し(90%、80%及び70%)、そして対応する溶液の粘度を測定した。
a) 水乳化性ポリイソシアネート1 90gを、ジプロピレングリコールジメチルエーテル10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、ジプロピレングリコールジメチルエーテル20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、ジプロピレングリコールジメチルエーテル30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、メトキシプロピルアセテート10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、メトキシプロピルアセテート20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、メトキシプロピルアセテート30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、ブチルグリコールアセテート10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、ブチルグリコールアセテート20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、ブチルグリコールアセテート30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、プロピレンカーボネート10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、プロピレンカーボネート20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、プロピレンカーボネート30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、TME(1,1,2,2,−テトラメトキシエタン)10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、TME(1,1,2,2,−テトラメトキシエタン)20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、TME(1,1,2,2,−テトラメトキシエタン)30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、ジオキサン10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、ジオキサン20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、ジオキサン30gと混合した。
a) 水乳化性ポリイソシアネート1 90gを、ジオキソラン10gと混合した。
b) 水乳化性ポリイソシアネート1 80gを、ジオキソラン20gと混合した。
c) 水乳化性ポリイソシアネート1 70gを、ジオキソラン30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、ジプロピレングリコールジメチルエーテル10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、ジプロピレングリコールジメチルエーテル20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、ジプロピレングリコールジメチルエーテル30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、メトキシプロピルアセテート10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、メトキシプロピルアセテート20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、メトキシプロピルアセテート30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、ブチルグリコールアセテート10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、ブチルグリコールアセテート20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、ブチルグリコールアセテート30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、プロピレンカーボネート10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、プロピレンカーボネート20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、プロピレンカーボネート30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、TME(1,1,2,2,−テトラメトキシエタン)10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、TME(1,1,2,2,−テトラメトキシエタン)20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、TME(1,1,2,2,−テトラメトキシエタン)30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、ジオキサン10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、ジオキサン20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、ジオキサン30gと混合した。
a) 水乳化性ポリイソシアネート2 90gを、ジオキソラン10gと混合した。
b) 水乳化性ポリイソシアネート2 80gを、ジオキソラン20gと混合した。
c) 水乳化性ポリイソシアネート2 70gを、ジオキソラン30gと混合した。
Claims (15)
- 以下、
a)少なくとも1つのポリイソシアネート、
b)少なくとも1つのポリイソシアネートb1)と、イソシアネートに対して反応性ではない少なくとも1つの親水性の基(基A)及びイソシアネートに対して反応性のある正確に1つの基(基B)を有する少なくとも1つの化合物b2)との、少なくとも1つの反応生成物、並びに
c)ジオキソラン
を含む混合物。 - 前記基(A)が、イオン性基及び/又はイオン性基に変換可能な基である、請求項1に記載の混合物。
- 前記基(A)の含有量が、成分a)及びb)1kgあたり0.1〜3molである、請求項2に記載の混合物。
- 前記基(A)が、非イオン性基である、請求項1に記載の混合物。
- 前記基(A)が、ポリアルキレンエーテル基である、請求項4に記載の混合物。
- 前記基(A)が、ポリエチレンエーテル基である、請求項4又は5に記載の混合物。
- 前記基(A)の含有量が、成分a)及びb)の合計に対して0.1〜30質量%である、請求項4から6までのいずれか1項に記載の混合物。
- 前記ポリイソシアネート(a)が、脂肪族ポリイソシアネートである、請求項1から7までのいずれか1項に記載の混合物。
- 前記ポリイソシアネート(a)が、2を超える官能価を有する、請求項1から8までのいずれか1項に記載の混合物。
- 前記反応性のある基が、ヒドロキシ基、メルカプト基、第一級アミノ基又は第二級アミノ基である、請求項1から9までのいずれか1項に記載の混合物。
- 前記成分a)〜c)の合計に対して、ジオキソラン2〜40質量%を含む、請求項1から10までのいずれか1項に記載の混合物。
- 水性ポリマー分散液のための添加剤としての、請求項1から11までのいずれか1項に記載の混合物の使用。
- 二成分コーティング材料であって、
a)少なくとも1つのポリイソシアネート、
b)ポリイソシアネートb1)と、少なくとも1つの親水性の基(基A)及びイソシアネートに対して反応性のある正確に1つの基(基B)を有する少なくとも1つの化合物b2)との、少なくとも1つの反応生成物、並びに
c)ジオキソラン
を含む混合物を、水性ポリマー分散液に添加することにより得られる、前記二成分コーティング材料。 - 水性ポリマー分散液中で分散されるポリマーが、ポリアクリレートポリオール、ポリエステルポリオール及びポリウレタンポリオールである、請求項13に記載の二成分コーティング材料。
- 請求項13又は14に記載の二成分コーティング材料を使用して得られる被覆された基材。
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JP5404598B2 (ja) * | 2007-03-26 | 2014-02-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 水乳化性ポリイソシアネート |
ITVA20070066A1 (it) * | 2007-07-26 | 2009-01-27 | Lamberti Spa | Composizioni idrodisperdibili di poliisocianati |
CN104736605B (zh) * | 2012-09-28 | 2018-02-06 | 巴斯夫欧洲公司 | 具有改进的光泽度的水可乳化型异氰酸酯 |
DE102012218081A1 (de) | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität |
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WO2020241479A1 (ja) * | 2019-05-29 | 2020-12-03 | 東ソー株式会社 | 自己乳化型ポリイソシアネート組成物、2液型塗料組成物及び塗膜 |
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EP3347397B1 (de) | 2022-01-26 |
US20180244827A1 (en) | 2018-08-30 |
WO2017042111A1 (de) | 2017-03-16 |
EP3347397A1 (de) | 2018-07-18 |
JP6856630B2 (ja) | 2021-04-07 |
US10696776B2 (en) | 2020-06-30 |
CN108350144B (zh) | 2021-11-05 |
RU2018112479A (ru) | 2019-10-09 |
KR20180050673A (ko) | 2018-05-15 |
CN108350144A (zh) | 2018-07-31 |
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