JPWO2019124511A1 - ブロックイソシアネート - Google Patents
ブロックイソシアネート Download PDFInfo
- Publication number
- JPWO2019124511A1 JPWO2019124511A1 JP2019560571A JP2019560571A JPWO2019124511A1 JP WO2019124511 A1 JPWO2019124511 A1 JP WO2019124511A1 JP 2019560571 A JP2019560571 A JP 2019560571A JP 2019560571 A JP2019560571 A JP 2019560571A JP WO2019124511 A1 JPWO2019124511 A1 JP WO2019124511A1
- Authority
- JP
- Japan
- Prior art keywords
- blocking agent
- compound
- polyisocyanate
- group
- isocyanate
- 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 138
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 138
- 239000002981 blocking agent Substances 0.000 claims abstract description 204
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 204
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 204
- 229920005862 polyol Polymers 0.000 claims abstract description 168
- 150000003077 polyols Chemical class 0.000 claims abstract description 158
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 131
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 22
- 230000003197 catalytic effect Effects 0.000 claims abstract description 14
- 230000003213 activating effect Effects 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- -1 amine compounds Chemical class 0.000 claims description 151
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 40
- 125000001931 aliphatic group Chemical group 0.000 claims description 39
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 229920005906 polyester polyol Polymers 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 17
- 229920005749 polyurethane resin Polymers 0.000 description 58
- 239000002904 solvent Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 44
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 43
- 239000000178 monomer Substances 0.000 description 38
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 36
- 239000002994 raw material Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 25
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 24
- 238000000576 coating method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 15
- 238000005452 bending Methods 0.000 description 13
- 238000010494 dissociation reaction Methods 0.000 description 13
- 230000005593 dissociations Effects 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 239000011342 resin composition Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229920002635 polyurethane Polymers 0.000 description 12
- 239000004814 polyurethane Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 9
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 150000002460 imidazoles Chemical class 0.000 description 7
- 229940049920 malate Drugs 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 229940043279 diisopropylamine Drugs 0.000 description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000013638 trimer Substances 0.000 description 5
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 4
- ZWXQPERWRDHCMZ-UHFFFAOYSA-N 2-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)NC(C)(C)C ZWXQPERWRDHCMZ-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 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 150000003217 pyrazoles Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 4
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000002483 hydrogen compounds Chemical class 0.000 description 3
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001944 Plastisol Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
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Classifications
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Abstract
【化1】
(式中、R1〜R3は、炭素数1〜12の炭化水素基または水素原子を示し、R1〜R3の少なくともいずれか1つが水素原子を示し、R1およびR3が互いに結合してヘテロ環を形成してもよい。R4およびR5は、炭素数1〜12の炭化水素基を示し、R4およびR1が互いに結合してヘテロ環を形成するとともに、R5およびR3が互いに結合してヘテロ環を形成してもよい。)
Description
本発明[2]は、前記高分子量ポリオールは、ポリカーボネートポリオール、ポリエステルポリオール、および、ポリテトラメチレンエーテルグリコールからなる群から選択される少なくとも1つのポリオールである、上記[1]に記載のブロックイソシアネートを含む。
まず、本発明のブロックイソシアネートの第1実施形態としての溶剤系ブロックイソシアネートについて説明する。溶剤系ブロックイソシアネートは、例えば、非水分散性ブロックイソシアネートであり、例えば、溶剤(後述)に溶解して用いられる。
ポリイソシアネート化合物は、ポリイソシアネートと、数平均分子量が250以上の高分子量ポリオールとの反応生成物であり、2つ以上の遊離のイソシアネート基を有する。
ポリイソシアネートとして、例えば、脂肪族ポリイソシアネート、芳香族ポリイソシアネート、芳香脂肪族ポリイソシアネートなどが挙げられる。ポリイソシアネートは、単独使用または2種以上併用することができる。
芳香族ポリイソシアネート誘導体は、単独使用または2種類以上併用することができる。
高分子量ポリオールは、ポリイソシアネートを変性する変性剤である。高分子量ポリオールの数平均分子量は、250以上、好ましくは、400以上、さらに好ましくは、500以上、とりわけ好ましくは、1000以上、例えば、10000以下、好ましくは、5000以下である。
次に、ポリイソシアネート化合物の調製について説明する。
ブロック剤は、第1ブロック剤と、第2ブロック剤とを含む。
第1ブロック剤は、イソシアネート基をブロックして不活性化する一方、脱ブロック後にはイソシアネート基を活性化し、また、イソシアネート基をブロックした状態および脱ブロックされた状態において、イソシアネート基を活性化させる触媒作用(後述)を有する。
上記一般式(1)において、R1〜R3は、互いに同一または相異なって、炭素数1〜12の炭化水素基または水素原子を示し、かつ、R1〜R3の少なくともいずれか1つが水素原子を示す。
第2ブロック剤は、イソシアネート基をブロックして不活性化する一方、脱ブロック後にはイソシアネート基を再生するブロック剤であって、また、再生されたイソシアネート基を活性化させる程度の触媒作用(後述)を有しないか、または、再生されたイソシアネート基を活性化させる程度の触媒作用(後述)を有したとしてもその触媒作用(後述)が上記の第1ブロック剤よりも小さいブロック剤である。
次に、溶剤系ブロックイソシアネートの製造について説明する。
次に、本発明のブロックイソシアネートの第2実施形態としての水系ブロックイソシアネートについて説明する。
親水性ポリイソシアネート化合物は、上記したポリイソシアネートと、上記した高分子量ポリオールと、活性水素基含有親水性化合物との反応生成物である。
次に、親水性ポリイソシアネート化合物の調製について説明する。
水系ブロックイソシアネートは、活性水素基含有親水性化合物により変性されていないポリイソシアネート化合物を親水性ポリイソシアネート化合物に変更する以外は、第1実施形態と同様の方法により製造される。つまり、水系ブロックイソシアネートは、上記した親水性ポリイソシアネート化合物と、上記した第1ブロック剤および第2ブロック剤とを反応させることにより製造される。そのため、水系ブロックイソシアネートの製造方法の詳細な説明を省略する。
上記したブロックイソシアネート(溶剤系ブロックイソシアネートおよび水系ブロックイソシアネート)では、ブロック剤によってブロックされる前のポリイソシアネート化合物(親水性ポリイソシアネート化合物)が、高分子量ポリオールとポリイソシアネートとの反応生成物であり、高分子量ポリオールによって変性されている。
そして、上記したブロックイソシアネート(溶剤系ブロックイソシアネートおよび水系ブロックイソシアネート)は、例えば、ポリウレタン樹脂原料、ポリオレフィン樹脂原料、ポリアクリル樹脂原料、ポリエステル樹脂原料などの公知の樹脂原料として用いることができ、好ましくは、ポリウレタン樹脂原料として用いられる。
1.実施例1〜20および比較例1〜4
室温(25℃)において、攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量2Lの反応器に、表1〜表5に示すポリイソシアネートおよび高分子量ポリオールを、表1〜表5に示す処方となるように、ジエチレングリコールエチルメチルエーテル(有機溶媒)79質量部に加えて、90℃において、残存するイソシアネート量に変化がなくなるまでウレタン化反応させ、ポリイソシアネート化合物を調製した。なお、比較例1では、高分子量ポリオールを添加せず、ポリイソシアネートをそのまま使用した。
次いで、表1〜表5に示す第2ブロック剤を、表1〜表5に示す処方となるように、反応溶液の温度が50℃を超えないように調整しながら、反応溶液に数回に分けて加えた。なお、比較例2では、第2ブロック剤を添加しなかった。
実施例1の溶剤系ブロックイソシアネートと、比較例1の溶剤系ブロックイソシアネートとを、表4に示す配合割合となるように混合して、溶剤系ブロックイソシアネートを得た。
アクリルポリオール(商品名:Q182、三井化学社製)およびt−ブタノール(モノオール)を、ジエチレングリコールエチルメチルエーテル(有機溶媒)に溶解したポリオール成分(溶液)を準備した。ポリオール成分は、最終的な溶剤系一液型ポリウレタン樹脂原料の固形分濃度が40質量%となり、t−ブタノール(モノオール)の濃度が5質量%となるように濃度調整した。
1.実施例23〜44および比較例5〜8
室温(25℃)において、攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量2Lの反応器に、表6〜表10に示すポリイソシアネート、高分子量ポリオールおよび親水性化合物を、表6〜表10に示す処方となるように、ジエチレングリコールエチルメチルエーテル(有機溶媒)89質量部に加えて、90℃において、残存するイソシアネート量に変化がなくなるまでウレタン化反応させ、親水性ポリイソシアネート化合物を調製した。なお、比較例5では、高分子量ポリオールを添加せず、ポリイソシアネートと親水性化合物とを反応させて、親水性ポリイソシアネート化合物を調製した。
実施例23の水系ブロックイソシアネートと、比較例5の水系ブロックイソシアネートとを、表9に示す配合割合となるように混合して、水系ブロックイソシアネートを得た。
アクリルポリオール(商品名:RE4788、三井化学社製)を、水に分散したポリオール成分(分散液)を準備した。ポリオール成分は、最終的な水系一液型ポリウレタン樹脂原料の固形分濃度が30質量%となるように濃度調整した。
1.塗膜の耐溶剤性
上記のように調製した溶剤系一液型ポリウレタン樹脂原料および水系一液型ポリウレタン樹脂原料のそれぞれを、100μmのアプリケーターにより、ブリキ基板上に塗布して、120℃で30分硬化させた。
上記のように調製した溶剤系一液型ポリウレタン樹脂原料および水系一液型ポリウレタン樹脂原料のそれぞれを、100μmのアプリケーターにより、鋼板上に塗布して、120℃で30分硬化させた。JIS K 5600−5−2(1999年)に準拠して、鋼板上の塗膜表面と反対側から、塗膜が形成された鋼板に20mm径の押し込み器をあて、鋼板をしっかり固定しておき、所定の速度で押し込み器を押し出して塗膜表面に割れ、剥がれを生じた時の押し出し長さ(mm)を評価した。その結果を表1〜10に示す。
上記のように調製した溶剤系一液型ポリウレタン樹脂原料および水系一液型ポリウレタン樹脂原料のそれぞれを、100μmのアプリケーターにより、鋼板上に塗布して、120℃で30分硬化させた。そして、塗膜が形成された鋼板を、デュポン式衝撃試験器の1/2インチの撃ち型と受け台との間に挟み、おもり(500g)を用いて、鋼板における塗膜が形成された面(表面)から衝撃を加えて、塗膜に損傷が現れるおもりの高さ(cm)を測定した。その結果を表1〜10に示す。
タケネートD127N:ビス(イソシアナトメチル)シクロヘキサンの3量体(H6XDIのイソシアヌレート変性体)、イソシアネート基含有量13.5質量%、三井化学社製、
タケネートD110N:キシリレンジイソシアネートのトリメチルロールプロパンアダクト体(ポリオール変性体、XDIのTNPアダクト体)、イソシアネート基含有量11.5質量%、三井化学社製、
タケネートD103H:トリレンジイソシアネートのトリメチルロールプロパンアダクト体(ポリオール変性体、TDIのTNPアダクト体)、イソシアネート基含有量13.0質量%、三井化学社製、
PTMG1000:ポリテトラメチレンエーテルグリコール、数平均分子量1000、三菱ケミカル社製、
PTMG650:ポリテトラメチレンエーテルグリコール、数平均分子量650、三菱ケミカル社製、
PTMG2000:ポリテトラメチレンエーテルグリコール、数平均分子量2000、三菱ケミカル社製、
PPG2000:ポリオキシプロピレングリコール、数平均分子量2000、和光純薬工業社製、
UH−100:1,6−ヘキサンジオールと炭酸ジメチルとの反応生成物であるポリカーボネートジオール、数平均分子量1000、宇部興産社製、
U−5620:タケラックU−5620、アジペート系ポリエステルポリオール、数平均分子量2000、三井化学社製、
TMG:1,1,3,3−テトラメチルグアニジン、
IMZ:イミダゾール、日本合成化学社製、
DMP:3,5−ジメチルピラゾール、
MEKO:メチルエチルケトキシム、東京化成工業社製、
DiPA:ジイソプロピルアミン、東京化成工業社製、
TMPDI:2,2,6,6−テトラメチルピペリジン、東京化成工業社製、
TMPDO:2,2,6,6−テトラメチルピペリジン−4−オン、東京化成工業社製、
TBIPA:N−tert−ブチルイソプロピルアミン、Aldrich社製、
MePEG1000:メトキシPEG#1000、ポリ(オキシエチレン)メチルエーテル、数平均分子量1000、東邦化学工業社製。
Claims (5)
- ポリイソシアネート化合物がブロック剤によってブロックされたブロックイソシアネートであって、
第1ブロック剤によりイソシアネート基がブロックされている第1潜在イソシアネート基と、第2ブロック剤によりイソシアネート基がブロックされている第2潜在イソシアネート基とを含有し、
前記第1ブロック剤は、下記一般式(1)で示され、前記第2ブロック剤よりもイソシアネート基を活性化させる触媒作用が大きく、
前記ポリイソシアネート化合物は、数平均分子量が250以上の高分子量ポリオールと、ポリイソシアネートとの反応生成物であることを特徴とする、ブロックイソシアネート。
- 前記高分子量ポリオールは、ポリカーボネートポリオール、ポリエステルポリオール、および、ポリテトラメチレンエーテルグリコールからなる群から選択される少なくとも1つのポリオールであることを特徴とする、請求項1に記載のブロックイソシアネート。
- 前記ポリイソシアネートは、脂肪族ポリイソシアネートからなることを特徴とする、請求項1に記載のブロックイソシアネート。
- 前記第2ブロック剤は、
イミダゾール系化合物、アルコール系化合物、フェノール系化合物、活性メチレン系化合物、アミン系化合物、イミン系化合物、オキシム系化合物、カルバミン酸系化合物、尿素系化合物、酸アミド系化合物、酸イミド系化合物、トリアゾール系化合物、ピラゾール系化合物、メルカプタン系化合物、重亜硫酸塩、イミダゾリン系化合物、および、ピリミジン系化合物からなる群から選択される2種のブロック剤を含有することを特徴とする、請求項1に記載のブロックイソシアネート。 - 活性水素基を含有する親水性化合物により変性されていることを特徴とする、請求項1に記載のブロックイソシアネート。
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PCT/JP2018/047053 WO2019124511A1 (ja) | 2017-12-22 | 2018-12-20 | ブロックイソシアネート |
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EP3950758A4 (en) * | 2019-03-29 | 2022-11-30 | Mitsui Chemicals, Inc. | CROSSLINKING AGENT FOR FIBERS OR LEATHER |
EP3950759A4 (en) * | 2019-03-29 | 2022-11-30 | Mitsui Chemicals, Inc. | BLOCKED ISOCYANATE, METHOD OF MAKING A MULTILAYER FILM AND MULTILAYER FILM |
WO2021059835A1 (ja) * | 2019-09-25 | 2021-04-01 | 日清紡ケミカル株式会社 | 親水性基を有する変性ポリカルボジイミド化合物 |
JP2021066782A (ja) * | 2019-10-21 | 2021-04-30 | Dic株式会社 | ブロックイソシアネートプレポリマー、硬化性組成物、硬化物及び接着剤 |
JP7528442B2 (ja) | 2019-12-27 | 2024-08-06 | Toppanホールディングス株式会社 | 蓄電デバイス用外装材 |
EP4215592A4 (en) * | 2020-09-18 | 2024-08-07 | Mitsui Chemicals Inc | WATER-DISPERSIBLE BLOCKED ISOCYANATE, FIBER TREATMENT AGENT, WATER-REPELLENT COMPOSITION, COATING COMPOSITION AND ADHESIVE |
WO2022107881A1 (ja) * | 2020-11-20 | 2022-05-27 | 東洋インキScホールディングス株式会社 | 無溶剤型反応性接着剤、その硬化物及び積層体 |
JP2023070109A (ja) * | 2021-11-05 | 2023-05-18 | 旭化成株式会社 | ブロックポリイソシアネート組成物及びその製造方法、樹脂組成物、樹脂膜及びその製造方法、並びに、積層体 |
WO2023162870A1 (ja) * | 2022-02-28 | 2023-08-31 | 旭化成株式会社 | ブロックイソシアネート組成物、塗料組成物及び塗膜 |
CN114672066A (zh) * | 2022-04-20 | 2022-06-28 | 浙江大学 | 一种聚氨酯的回收利用方法 |
GB2624517A (en) * | 2022-09-22 | 2024-05-22 | Vuba Building Products Ltd | Resin bonded/bound surfacing |
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CN112204068B (zh) | 2022-05-27 |
JP7106576B2 (ja) | 2022-07-26 |
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