JP2021530592A - 乾燥が向上したイオン性親水化ポリイソシアネート - Google Patents
乾燥が向上したイオン性親水化ポリイソシアネート Download PDFInfo
- Publication number
- JP2021530592A JP2021530592A JP2021501289A JP2021501289A JP2021530592A JP 2021530592 A JP2021530592 A JP 2021530592A JP 2021501289 A JP2021501289 A JP 2021501289A JP 2021501289 A JP2021501289 A JP 2021501289A JP 2021530592 A JP2021530592 A JP 2021530592A
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- JP
- Japan
- Prior art keywords
- polyisocyanate
- sulfonic acid
- weight
- group
- aliphatic
- 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
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 216
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 216
- 238000001035 drying Methods 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 54
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 44
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 35
- 239000008199 coating composition Substances 0.000 claims abstract description 15
- -1 hydroxy- Chemical class 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- 239000004814 polyurethane Substances 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 9
- PJWWRFATQTVXHA-UHFFFAOYSA-N Cyclohexylaminopropanesulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCC1 PJWWRFATQTVXHA-UHFFFAOYSA-N 0.000 claims description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- MKWKNSIESPFAQN-UHFFFAOYSA-N N-cyclohexyl-2-aminoethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCCC1 MKWKNSIESPFAQN-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 4
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- GHSGJYANZVSEPH-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanesulfonic acid Chemical compound CC(C)NCCS(O)(=O)=O GHSGJYANZVSEPH-UHFFFAOYSA-N 0.000 claims description 3
- ZBSWKBYXONRLTM-UHFFFAOYSA-N 3-(propan-2-ylamino)propane-1-sulfonic acid Chemical compound CC(C)NCCCS(O)(=O)=O ZBSWKBYXONRLTM-UHFFFAOYSA-N 0.000 claims description 3
- XNPKNHHFCKSMRV-UHFFFAOYSA-N 4-(cyclohexylamino)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCNC1CCCCC1 XNPKNHHFCKSMRV-UHFFFAOYSA-N 0.000 claims description 3
- ZCVOCAWBPMHJPF-UHFFFAOYSA-N 4-(propan-2-ylamino)butane-1-sulfonic acid Chemical compound C(C)(C)NCCCCS(=O)(=O)O ZCVOCAWBPMHJPF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000006384 oligomerization reaction Methods 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 description 41
- 239000011248 coating agent Substances 0.000 description 34
- 239000011230 binding agent Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 15
- 239000003431 cross linking reagent Substances 0.000 description 13
- 239000003973 paint Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 9
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 8
- 229920002396 Polyurea Polymers 0.000 description 8
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000000126 substance Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical class OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- XREKCAGAPAEVFE-UHFFFAOYSA-J tri(hexadecanoyloxy)stannyl hexadecanoate Chemical compound [Sn+4].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O XREKCAGAPAEVFE-UHFFFAOYSA-J 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SUXIKHBBPQWLHO-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-(8-methyl-1-phenylnonyl)-lambda5-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C(CCCCCCC(C)C)C1=CC=CC=C1 SUXIKHBBPQWLHO-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
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-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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-
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- C08G18/8029—Masked aromatic polyisocyanates
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Abstract
Description
ここで、R1は10個までの炭素原子を有するアルキルまたはアリール基であり、これはエステル基、カルボニル基、2個までの第三級アミノ基および/またはヒドロキシル基を含み得るか、または5員もしくは6員の環状脂肪族基であり、これは任意に、窒素原子または酸素原子を含んでもよく、そしてまた、さらなるヒドロキシル基によって置換されていてもよい。
ここで、R2、R3およびR4は、それぞれ独立して同一または異なる基であり、水素または飽和または不飽和、線状または分岐、脂肪族、環状脂肪族、芳香脂肪族または芳香族有機基を表し、これはさらにその鎖中にヘテロ原子を含んでいてもよく、ここで、R3およびR4は、一体となって環、好ましくは互いに組み合わせて縮合芳香族環を形成してもよく、ただし、基R3およびR4の少なくとも1つは水素ではない。
ここで、R5およびR6は、それぞれ独立して同一または異なる基であり、水素、または飽和または不飽和、線状または分岐、脂肪族または環状脂肪族または芳香族の、1〜18個の炭素原子を有する有機基であり、これは、置換または非置換であり、および/またはその鎖中にヘテロ原子を含み、ここで、R5およびR6は、互いにおよび任意に1つのさらなる窒素原子または1つの酸素原子と組み合わせて、3〜8個の炭素原子を有する環状脂肪族環または複素環を形成してもよく、これは、任意にさらに置換されてもよく、そして、R7は、2〜6個の炭素原子を有する線状または分岐の脂肪族基である。
(i)本発明によるスルホネート基で親水性に変性されたポリイソシアネート混合物および
(ii)例として述べたタイプの未変性ポリイソシアネート
の混合物からなるため、本発明によるポリイソシアネート混合物でもある。
NCO含量は、DIN EN ISO 11909:2007−05に従って滴定により測定された。
全ての粘性測定は、DIN EN ISO 3219:1994−10に従って、Anton Paar Germany GmbH(DE)からのPhysica MCR 51レオメーターを用いて、250sー1のせん断速度で行われた。
残留モノマー含量は、DIN EN ISO 10283:2007−11に従って、内部標準を用いたガスクロマトグラフィーにより測定された。
水分含量は、MethromからのTitrando 841自動滴定ユニットを使用して、DIN 53715(DIN 51777 Part 1(1973年版)に基づいて作成)に従って、Karl Fischerによる体積滴定によって決定された。この方法の測定範囲は0.01〜99重量%である。
得られたコーティングの光沢は、DIN EN ISO 2813:2015−02に従って60°および20°の角度で反射率測定によって測定された。測定値が高いほど、光沢は高い。
ヘイズは、DIN EN ISO 13803:2015−02に従って60°および20°の角度で測定された。ヘイズ値が低いほど、コーティングは曇りがなくなる。
Koenigによる振り子減衰は、DIN EN ISO 1522;2007−04に従って、ガラス板上で決定された。
コーティングシステムの乾燥特性は、DIN 53 150:2002−09に従って決定された。
ふくれのない最大層厚さ(ふくれの程度)は、DIN EN ISO 4628ー2:2016−07に従って決定された。
耐薬品性は、コーヒー、赤ワイン、水、マスタードおよびエタノールを試験液として用いて、DIN EN 12720:2014−02に記載された方法によって測定された。
ポリイソシアネートC)
ポリイソシアネートC1
イソシアヌレート基を含むHDIポリイソシアネートは、EP−A 330 966の例11に基づきHDIの触媒三量化によって製造され、ここで、粗混合物のNCO含有量40%でジブチルホスフェートの添加により反応を停止させる変更を伴った。その後、未転化のHDIを130℃の温度および0.2mbarの圧力で薄膜蒸留によって除去した。
NCO含有量: 21.7%
NCO官能価: 3.4
モノマーHDI: 0.1%
粘度(23℃): 3080mPas
色数(ハーゼン): 18
イソシアヌレート基を含むPDIポリイソシアネートは、ポリイソシアネート成分A2)についてのWO2016/146579に記載の方法によりPDIを触媒三量化することにより製造された。その反応は、使用した触媒の量に基づいて、等モル量のリン酸ジブチルを添加することと、さらに80℃で30分間撹拌することにより、粗混合物のNCO含量36.7%にて失活させた。その後、温度140℃、圧力0.5mbarで薄膜蒸留により未転化PDIを除去した。
NCO含有量: 21.8%
NCO官能価: 3.5
モノマーPDI: 0.09%
粘度(23℃): 9850mPas
色数(ハーゼン): 34
3−(シクロヘキシルアミノ)プロパンスルホン酸(Sigma−Aldrich Chemie Gmbh、Munich、DE)をアミノスルホン酸として使用し、これは、真空下(100℃/約0.5mbar)で3時間乾燥した後に0.4%の含水率を有した。
943.9g(4.88val)のイソシアヌレート基含有開始ポリイソシアネートC1)を、36.0g(0.16val)の3−(シクロヘキシルアミノ)プロパンスルホン酸(CAPS)、20.1g(0.16mol)のジメチルシクロヘキシルアミンおよび0.05g(50ppm)の2,6−ジ−tert−ブチル−4−メチルフェノールと共に、乾燥窒素下、100℃で4:00時間、スルホネート基を含む実質的に透明なポリイソシアネート混合物が優勢になるまで撹拌した。室温に冷却し、T5500フィルター層(Seitz)で濾過した後、以下の特性データを決定した:
NCO含有量: 19.8%
NCO官能価: 3.3
粘度(23℃): 8210mPas
色数(ハーゼン): 18
スルホネート基含有量: 1.30%(SO3として計算;モル重量%=80g/mol)
960.7g(4.92val)のイソシアヌレート基含有開始ポリイソシアネートC1)を、25.0g(0.11val)の3−(シクロヘキシルアミノ)プロパンスルホン酸(CAPS)、14.3g(0.11mol)のジメチルシクロヘキシルアミンおよび0.05g(50ppm)の2,6−ジ−tert−ブチル−4−メチルフェノールと共に、乾燥窒素下、100℃で3:30時間、スルホネート基を含む実質的に透明なポリイソシアネート混合物が優勢になるまで撹拌した。室温に冷却し、T5500フィルター層(Seitz)で濾過した後、以下の特性データを決定した:
NCO含有量: 20.2%
NCO官能価: 3.3
粘度(23℃): 4050mPas
色数(ハーゼン): 18
スルホネート基含有量: 0.90%(SO3として計算;モル重量%=80g/mol)
965.3g(4.99val)のイソシアヌレート基含有開始ポリイソシアネートC1)を、22.1g(0.10val)の3−(シクロヘキシルアミノ)プロパンスルホン酸(CAPS)、12.6g(0.10mol)のジメチルシクロヘキシルアミンおよび0.05g(50ppm)の2,6−ジ−tert−ブチル−4−メチルフェノールと共に、乾燥窒素下、100℃で3:30時間、スルホネート基を含む実質的に透明なポリイソシアネート混合物が優勢になるまで撹拌した。室温に冷却し、T5500フィルター層(Seitz)で濾過した後、以下の特性データを決定した:
NCO含有量: 20.5%
NCO官能価: 3.3
粘度(23℃): 3740 mPas
色数(ハーゼン): 20
スルホネート基含有量: 0.80%(SO3として計算;モル重量%=80g/mol)
937.2g(4.86val)のイソシアヌレート基含有開始ポリイソシアネートC2)を、40.0g(0.18val)の3−(シクロヘキシルアミノ)プロパンスルホン酸(CAPS)、22.8g(0.18mol)のジメチルシクロヘキシルアミン、0.05g(50ppm)の2,6−ジ−tert−ブチル−4−メチルフェノールおよび250gのMPAと一緒に、乾燥窒素下、100℃で3:15時間、スルホネート基を含む実質的に透明なポリイソシアネート混合物が優勢になるまで撹拌した。室温に冷却し、T5500フィルター層(Seitz)で濾過した後、以下の特性データを決定した:
NCO含有量: 15.7%
NCO官能価: 3.4
固形分: 80%
粘度(23℃): 3420mPas
色数(ハーゼン): 17
スルホネート基含有量: 1.45%(SO3として計算;モル重量%=80g/mol、固体に対して)
ウレタン基含有TDIポリイソシアネートは、EP−A 0546399の例4に基づいて製造され、ここで、80%の2,4−TDIと20%の2,6−TDIの混合物を使用し、得られた淡黄色樹脂を1−メトキシ−2−プロピルアセテート(MPA)中に60%の濃度で溶解するという改変を伴う。
NCO含有量: 10.6%
NCO官能価: 3.3
モノマー2,4−TDI: 0.13%
モノマー2,6−TDI: 0.14%
粘度(23℃): 370mPas
色数(ハーゼン): 34
ポリイソシアネート成分A1)、A2)およびA3)を、様々な比率で30℃にてポリイソシアネート成分B1)と混合し、30分間撹拌することによって均質化した。その後、ポリイソシアネート混合物の固体含有量をそれぞれの場合においてMPAで70%に調整した。
Bayhydrol A 2651(Covestro AG、Leverkusen)の名称で入手できる、樹脂固体に対して、40%の固形分および3.0%のOH含有量を有する市販の水性ヒドロキシ官能性ポリアクリレート分散液100重量部を、市販の非イオン性湿潤剤(Surfynol AD01、Evonik Materials Netherlands BV、Utrecht)2.6重量部、市販の流量制御添加剤(TEGO Flow 425、Evonik Resource Efficiency GmbH、Essen)0.16重量部、および市販の増粘剤(OPTIFLO−TVS VF、BYK−Chemie GmbH、Wesel)0.16重量部と混合した。このクリアコート材料に、例1〜10のポリイソシアネート混合物を、それぞれの場合において表2に特定された量(それぞれの場合において、イソシアネート基対アルコール性水酸基の当量比1.5:1に相当する)で加え、その混合物を1000rpmで5分間撹拌することによって均質化した。次いで、クリアコートの固形分を、水の添加によって、45%に調整した。
ふくれのない(blister−free)最大の層厚さを決定するために、例20および比較例11からのクリアコートを、ステップギャップフィルムアプリケーターの助けを借りて黒色プレキシガラスシートに適用し、それぞれの場合において、室温(約25℃)および55%相対空気湿度で乾燥させた。以下の表は、DIN EN ISO 4628−2:2016−07(0=最良の等級;5=最悪の等級)に従って、適用された種々の層の厚さについての視覚的に評価されたふくれの程度を示す。
Bayhydrol A 2651(Covestro AG、Leverkusen)の名称で入手できる、樹脂固体に対して、40%の固形分および3.0%のOH含有量を有する市販の水性ヒドロキシ官能性ポリアクリレート分散液100重量部を、市販の非イオン性湿潤剤(Surfynol AD01、Evonik Materials Netherlands BV、Utrecht)2.8重量部、市販の水性白色顔料分散液(White Aquamac 6、Proquimac PFC,S.A.、Barcelona、Spain)38.2重量部、市販の増粘剤(OPTIFLO−TVS VF、BYK−Chemie GmbH、Wesel)2.0重量部および脱イオン水29.8重量部と混合して、白色コーティングを得た。この原料混合物に、例9からのポリイソシアネート混合物37.4重量部を加え(イソシアネート基対アルコール性水酸基の当量比1.7:1に相当する)、その混合物を1000rpmで5分間撹拌することによって均質化した。
Claims (15)
- 脂肪族的および/または環状脂肪族的に結合したイソシアネート基を有するポリイソシアネート成分A)と、芳香脂肪族的および/または芳香族的に結合したイソシアネート基を有するポリイソシアネート成分B)とを含むポリイソシアネート混合物であって、前記ポリイソシアネート成分A)が化学的に結合した形態でスルホネート基(SO3として計算される;モル重量=80g/mol)を少なくとも0.85重量%含み、前記ポリイソシアネート成分B)の割合が、前記成分A)およびB)の総量の7〜43重量%であることを特徴とする、ポリイソシアネート混合物。
- 前記ポリイソシアネート成分A)が、少なくとも1つの脂肪族および/または環状脂肪族ポリイソシアネートC)の、イソシアネート基に反応性である少なくとも1つの基を有し、1つ以上のスルホン酸および/またはスルホネート基を含む少なくとも1つの有機化合物D)と、任意選択でイソシアネート基に反応性である少なくとも1つの基を含む少なくとも1つの非イオン性親水性または疎水性化合物E)との反応生成物であり、該反応生成物は、さらなる助剤および添加剤F)の存在下で調製されたものでもよいことを特徴とする、請求項1に記載のポリイソシアネート混合物。
- 前記ポリイソシアネートC)が、脂肪族的および/または環状脂肪族的に結合したイソシアネート基を有するジイソシアネートおよび/またはポリイソシアネートであることを特徴とする、請求項2に記載のポリイソシアネート混合物。
- 前記ポリイソシアネートC)が、PDI、HDI、IPDIおよび/または4,4’−ジイソシアナトジシクロヘキシルメタン、好ましくはPDIおよび/またはHDIに基づくものであることを特徴とする、請求項2または3に記載のポリイソシアネート混合物。
- 前記有機化合物D)が、ヒドロキシ−、メルカプト−および/またはアミノ−官能性スルホン酸および/またはその塩であることを特徴とする、請求項2〜4のいずれかに記載のポリイソシアネート混合物。
- 前記有機化合物D)が、一般式(III)のアミノ官能性スルホン酸および/またはその塩であることを特徴とする、請求項2〜5のいずれかに記載のポリイソシアネート混合物。
〔式(III)において、R5およびR6は、それぞれ独立して同一または異なる基であり、水素または飽和または不飽和で、線状または分岐の、脂肪族または環状脂肪族または芳香族の、1〜18個の炭素原子を有する有機基であり、前記有機基が、置換または非置換であり、および/またはその鎖中にヘテロ原子を含み、ここで、R5およびR6は、互いにおよび任意選択で1つのさらなる窒素原子または1つの酸素原子と組み合わせて、3〜8個の炭素原子を有する脂肪族環または複素環を形成してもよく、前記環はさらに置換されていてもよく、そして、R7は、2〜6個の炭素原子を有する線状または分岐脂肪族基である。〕 - 前記有機化合物D)が、2−イソプロピルアミノエタン−1−スルホン酸、3−イソプロピルアミノプロパン−1−スルホン酸、4−イソプロピルアミノブタン−1−スルホン酸、2−シクロヘキシルアミノエタン−1−スルホン酸、3−シクロヘキシルアミノプロパン−1−スルホン酸および/または4−シクロヘキシルアミノブタン−1−スルホン酸および/またはそれらの塩であることを特徴とする、請求項2〜6のいずれかに記載のポリイソシアネート混合物。
- 前記有機化合物D)が、N,N−ジメチルブチルアミン、N,N−ジエチルメチルアミン、N,N−ジイソプロピルエチルアミン、N,N−ジメチルシクロヘキシルアミン、N−メチルピペリジン、N−エチルモルホリンで中和されたスルホネート基の形態で少なくとも20mol%の範囲で存在していることを特徴とする、請求項2〜7のいずれかに記載のポリイソシアネート混合物。
- 前記非イオン性親水性または疎水性有機化合物E)が、純粋なポリエチレンオキシドポリエーテルアルコールおよび/または混合ポリアルキレンオキシドポリエーテルアルコール(ここで、そのアルキレンオキシド単位が、少なくとも70mol%の範囲のエチレンオキシド単位からなる)、および/またはそれぞれの場合において少なくとも8個の炭素原子を含む脂肪族アルコールまたは脂肪酸エステルアルコールであることを特徴とする、請求項2〜8のいずれかに記載のポリイソシアネート混合物。
- 前記ポリイソシアネート成分A)が、化学的に結合した形態でスルホネート基(SO3として計算される;モル重量=80g/mol)を少なくとも0.90重量%、好ましくは0.95重量%、より好ましくは1.00〜3.00重量%、最も好ましくは1.10〜1.80重量%含むことを特徴とする、請求項1〜9のいずれかに記載のポリイソシアネート混合物。
- 前記ポリイソシアネート成分B)が、ポリオールとの反応および/またはオリゴマー化によってモノマー2,4−および/または2,6−TDIから得られるウレタンおよび/またはイソシアネート構造を有するポリイソシアネートであることを特徴とする、請求項1〜10のいずれかに記載のポリイソシアネート混合物。
- 前記ポリイソシアネート成分B)の割合が、前記成分A)およびB)の総量の10〜40重量%、好ましくは15〜35重量%、最も好ましくは20〜30重量%であることを特徴とする、請求項1〜11のいずれかに記載のポリイソシアネート混合物。
- ポリウレタンプラスチックの製造における開始成分としての、請求項1〜12のいずれかに記載の少なくとも1つのポリイソシアネート混合物の使用。
- 請求項1〜12のいずれかに記載の少なくとも1つのポリイソシアネート混合物を含むコーティング組成物。
- 請求項14に記載のコーティング組成物でコーティングされた基材であって、該コーティング組成物が熱の作用によって硬化されてもよい、基材。
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Application Number | Priority Date | Filing Date | Title |
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CNPCT/CN2018/096488 | 2018-07-20 | ||
PCT/CN2018/096488 WO2020014971A1 (en) | 2018-07-20 | 2018-07-20 | Ionically hydrophilized polyisocyanates with improved drying |
EP18185060.3 | 2018-07-23 | ||
EP18185060.3A EP3599255A1 (en) | 2018-07-23 | 2018-07-23 | Ionically hydrophilized polyisocyanates with improved drying |
PCT/EP2019/068780 WO2020016116A1 (en) | 2018-07-20 | 2019-07-12 | Ionically hydrophilized polyisocyanates with improved drying |
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US (1) | US20210130530A1 (ja) |
EP (1) | EP3824009B1 (ja) |
JP (1) | JP7397056B2 (ja) |
CN (2) | CN113651944B (ja) |
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WO2024000342A1 (zh) * | 2022-06-30 | 2024-01-04 | 万华化学集团股份有限公司 | 一种亲水改性聚异氰酸酯及其制备方法和应用 |
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- 2019-07-12 CN CN201980039268.7A patent/CN112566957B/zh active Active
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US20210130530A1 (en) | 2021-05-06 |
WO2020016116A1 (en) | 2020-01-23 |
CN112566957A (zh) | 2021-03-26 |
CN112566957B (zh) | 2021-12-10 |
CN113651944A (zh) | 2021-11-16 |
CN113651944B (zh) | 2022-07-15 |
JP7397056B2 (ja) | 2023-12-12 |
ES2913002T3 (es) | 2022-05-30 |
EP3824009B1 (en) | 2022-03-09 |
EP3824009A1 (en) | 2021-05-26 |
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