JP6703529B2 - Nco不含化合物および硬化性組成物におけるその使用 - Google Patents
Nco不含化合物および硬化性組成物におけるその使用 Download PDFInfo
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- JP6703529B2 JP6703529B2 JP2017517344A JP2017517344A JP6703529B2 JP 6703529 B2 JP6703529 B2 JP 6703529B2 JP 2017517344 A JP2017517344 A JP 2017517344A JP 2017517344 A JP2017517344 A JP 2017517344A JP 6703529 B2 JP6703529 B2 JP 6703529B2
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- 150000001875 compounds Chemical class 0.000 title claims description 97
- 239000000203 mixture Substances 0.000 title claims description 91
- 150000003077 polyols Chemical class 0.000 claims description 66
- 229920005862 polyol Polymers 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000005056 polyisocyanate Substances 0.000 claims description 29
- 229920001228 polyisocyanate Polymers 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 229920000768 polyamine Polymers 0.000 claims description 28
- 229920000570 polyether Polymers 0.000 claims description 18
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 8
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-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 7
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 7
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 229960002887 deanol Drugs 0.000 claims description 4
- RLKMOPWWGZKHOP-UHFFFAOYSA-N 1-butylpiperidin-4-ol Chemical compound CCCCN1CCC(O)CC1 RLKMOPWWGZKHOP-UHFFFAOYSA-N 0.000 claims description 3
- HUXGPXHPGSIYOD-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound O=C=NC1CCCCC1CC1C(N=C=O)CCCC1 HUXGPXHPGSIYOD-UHFFFAOYSA-N 0.000 claims description 3
- FPWRWTXOOZSCTB-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CC(N=C=O)CCC1CC1C(N=C=O)CCCC1 FPWRWTXOOZSCTB-UHFFFAOYSA-N 0.000 claims description 3
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 3
- VGUWFGWZSVLROP-UHFFFAOYSA-N 1-pyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 VGUWFGWZSVLROP-UHFFFAOYSA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- SMBYUOXUISCLCF-UHFFFAOYSA-N n-ethyl-n-methylpropan-1-amine Chemical compound CCCN(C)CC SMBYUOXUISCLCF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 22
- 239000012948 isocyanate Substances 0.000 description 13
- 150000002513 isocyanates Chemical class 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 13
- 239000004814 polyurethane Substances 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- -1 aromatic hydrocarbon radical Chemical class 0.000 description 12
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920000909 polytetrahydrofuran Polymers 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000009864 tensile test Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005263 alkylenediamine group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
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- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical group C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
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- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- YSPXCGLGTIULDQ-UHFFFAOYSA-N 1,6-diisocyanato-2,3,3-trimethylhexane;2,2,4-trimethylhexane Chemical compound CCC(C)CC(C)(C)C.O=C=NCC(C)C(C)(C)CCCN=C=O YSPXCGLGTIULDQ-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
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- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- KSQSUDDRZLCKSW-UHFFFAOYSA-N 2,4-dimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)CCN KSQSUDDRZLCKSW-UHFFFAOYSA-N 0.000 description 1
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- NSKYMLWGJWRTQE-UHFFFAOYSA-N bis(2-isocyanatoethyl) benzene-1,2-dicarboxylate Chemical compound O=C=NCCOC(=O)C1=CC=CC=C1C(=O)OCCN=C=O NSKYMLWGJWRTQE-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- WVRQIJKYSIFASA-UHFFFAOYSA-N nonane-1,2,9-triamine Chemical compound NCCCCCCCC(N)CN WVRQIJKYSIFASA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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Description
実施例1:PTHFジエステルと共役したイソホロンジイソシアネート(IPDI)(以下、PITHF)の合成
40gのポリテトラヒドロフラン(PTHF、Mn=1000g/mol)を、250mLの3つ口丸底フラスコ中に加え、真空下、120℃で1.5時間加熱した。次いで、該温度を90℃まで冷却し、該反応混合物に窒素(または同等の不活性ガス)をパージし、4.45gのイソホロンジイソシアネート(IPDI)を添加し、該温度を110℃まで高めた。反応混合物を少なくとも12時間、滴定(遊離イソシアネート含量は、例えば、アミンを用いる遊離イソシアネートの滴定、および、未反応アミンの逆滴定により容易に測定することができる)により確認されたように、全てのNCO基が消費されるまで撹拌した。
50gのPTHF(Mn=1000g/mol)を、250mLの3つ口丸底フラスコに添加し、真空下、120℃で1.5時間加熱した。次いで、該温度を90℃まで冷却し、窒素をパージし、4.21gのヘキサメチレンジイソシアネート(HDI)を添加した後、該温度を110℃まで高めた。反応混合物を少なくとも12時間、滴定により確認されるように、全てのNCO基が消費されるまで撹拌した。
実施例3:実施例1から得た化合物(PITHF)および追加の化合物を有する組成物
実施例1で得た2gの化合物、および、3つの−O−(C=O)−C≡C−H基を含む0.048gの追加の化合物(Mn 約1000g/mol)を、DABCO(0.0058g)のエチルアセテート(0.4ml)溶液中に添加し、該混合物を、室温で、大気中に暴露して放置した。2時間後、茶色の非粘着性ポリマー(硬化した本発明の組成物)が得られた。
破断点伸び:330%
引張強度:3.38MPa
実施例1で得た2gの化合物を、DABCO(0.005g)のエチルアセテート(0.4ml)溶液中に添加し、該混合物を、室温で、大気中に暴露して放置した。2時間後、薄茶色の非粘着性ポリマーが得られた。
破断点伸び:123%
引張強度:1.66MPa
実施例2で得た2gの化合物を、DABCO(0.005g)のエチルアセテート(0.4ml)溶液中に添加し、該混合物を、室温で、大気中に暴露して放置した。2時間後、薄茶色の非粘着性ポリマーが得られた。
破断点伸び:60%
引張強度:1.67MPa
(分解温度(Td))
次の表に、上記に述べた実施例のいくつかによる硬化組成物、ならびに、詳細には記載されていないが実施例4および5に従い調製した2つのさらなる硬化した本発明の組成物の分解温度を示す。
以下の表に、本発明の硬化組成物のいくつかについての破断点伸び/引張強度を示す、ここで、全ての組成物は上記のようにして調製し、硬化させた。
表2は、(同一のポリオールを維持する際の)これらの特性に対するイソシアネート基の影響を示し、
表3は、側鎖(ポリオール)の分子量の影響を示し、
表4は、3つの−O−(C=O)−C≡C−H基を含むさらなる化合物(実施例1参照)の影響を示す。
本明細書の当初の開示は、少なくとも下記の態様を包含する。
〔1〕少なくとも2つの−(NH−C=O)−基および少なくとも2つの−(C=O)−C≡C−R 1 基を含む化合物であって、
ここで、R 1 は、水素または1〜12個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表す、化合物。
〔2〕a)
i.少なくとも2つのイソシアネート基を有するポリイソシアネートと、
ii.ポリオールもしくはポリアミンまたはそれらの混合物とを反応させて中間体を形成すること、
ここで、ポリオールおよびポリアミンのヒドロキシル基、第1級アミノ基および第2級アミノ基の合計に対する、ポリイソシアネートのNCO基のモル比は、1より小さい、
b)式R 2 O−(C=O)−C≡C−R 1 で表される化合物を、ステップa)の中間体と、該中間体のヒドロキシル基、第1級アミノ基および第2級アミノ基の合計に対してモル過剰で反応させること、
ここで、R 1 は水素または1〜12個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表し、
R 2 は、水素または1〜4個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表す、
により得ることができる、前記〔1〕に記載の化合物。
〔3〕−(NH−C=O)−基は、尿素および/またはウレタン基、好ましくはウレタン基により供される、前記〔1〕または〔2〕に記載の化合物。
〔4〕ポリオールは、ポリエーテルポリオール、ポリエーテルポリオールブロックコポリマー、ポリエステルポリオール、ポリエステルポリオールブロックコポリマーまたはそれらの混合物を含む群から、好ましくはポリエチレングリコール、ポリプロピレングリコールおよびポリテトラヒドロフラン、ならびにそれらの混合物を含む群から選択される、前記〔2〕〜〔3〕のいずれかに記載の化合物。
〔5〕ポリオール/ポリアミンの数平均分子量(M n )は、少なくとも200、好ましくは200〜20000、最も好ましくは1000〜5000g/molである、前記〔2〕〜〔4〕のいずれかに記載の化合物。
〔6〕ポリイソシアネートは、2,4-トルエンジイソシアネート、2,6-トルエンジイソシアネート、4,4’-ジフェニルメタンジイソシアネート、2,4’−ジフェニルメタンジイソシアネート、2,2’-ジフェニルメタンジイソシアネート、イソホロンジイソシアネート、ヘキサメチレンジイソシアネート、4,4’-メチレンジシクロヘキシルジイソシアネート、2,4’−メチレンジシクロヘキシルジイソシアネート、2,2’-メチレンジシクロヘキシルジイソシアネート、およびそれらの混合物を含む群から選択される、前記〔2〕〜〔5〕のいずれかに記載の化合物。
〔7〕少なくとも2つの−(NH−C=O)−基を含む第1ユニット、
少なくとも2つの−(C=O)−C≡C−R 1 基を含む第2ユニット、および、
触媒
を含み、ここで、R 1 は水素または1〜12個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表す、硬化性組成物。
〔8〕−(NH−C=O)−基は尿素および/またはウレタン基により供される、前記〔7〕に記載の硬化性組成物。
〔9〕第1ユニットおよび第2ユニットは1つの化合物の部分である、前記〔7〕または〔8〕に記載の硬化性組成物。
〔10〕第1ユニットおよび第2ユニットを含む化合物は、前記〔1〕〜〔6〕のいずれかに記載の化合物である、前記〔9〕に記載の硬化性組成物。
〔11〕第1ユニットおよび第2ユニットは異なる化合物の部分であり、好ましくは第1ユニットは熱可塑性ポリウレタンの部分である、前記〔7〕または〔8〕に記載の硬化性組成物。
〔12〕触媒は、第2級または第3級アミンであり、好ましくは、1,4-ジアザビシクロ[2.2.2]オクタン、テトラメチルエチレンジアミン、N,N-ジイソプロピルエチルアミン、トリエタノールアミン、トリス(2-ピリジルメチル)アミン、トリブチルアミン、4-ジメチルアミノフェノール、N-エチル-N-メチルプロピルアミン、N-メチルピペリジン、N-ブチル-4-ヒドロキシピペリジン、1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン、1,5-ジアザビシクロ[4.3.0]ノナ-5-エン、イミダゾリン、ベンズイミダゾール、ジメチルアミノエタノール、ピロール、モルホリン、ピペリジン、ピペラジン、インドール、およびそれらの混合物からなる群から選択され、より好ましくは1,4-ジアザビシクロ[2.2.2]オクタンである、前記〔7〕〜〔11〕のいずれかに記載の硬化性組成物。
〔13〕第2ユニットは、少なくとも2つのOH基を有するポリエーテルポリオール、好ましくはグリセロールプロポキシレートと、式R 2 O−(C=O)−C≡C−R 1 で表される化合物とを、ポリエーテルポリオールの2つのOH基に対して少なくとも等量で反応させることにより得られる化合物により供され、
ここで、R 1 は、水素または1〜12個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表し、
R 2 は、水素または1〜4個の炭素原子を有する基、好ましくは水素またはCH 3 、最も好ましくは水素を表す、
前記〔11〕〜〔12〕のいずれかに記載の硬化性組成物。
〔14〕第2ユニットを含む化合物の数平均モル質量(M n )は500〜1500g/molである、前記〔13〕に記載の硬化性組成物。
〔15〕接着剤、コーティング、流延用組成物としての、または、シーラントとしての、前記〔7〕〜〔14〕のいずれかに記載の組成物の使用。
Claims (9)
- 少なくとも2つの−(NH−C=O)−基を含む第1ユニット、
少なくとも2つの−(C=O)−C≡C−R1基を含む第2ユニット、および、
触媒
を含み、ここで、R1は水素または1〜12個の炭素原子を有する基を表し、−(NH−C=O)−基は尿素および/またはウレタン基により供され、第1ユニットおよび第2ユニットは1つの化合物の部分であり、かつ、室温で硬化性である、硬化性組成物。 - 第1ユニットおよび第2ユニットを含む化合物は、
a)
i.少なくとも2つのイソシアネート基を有するポリイソシアネートと、
ii.ポリオールもしくはポリアミンまたはそれらの混合物とを反応させて中間体を形成すること、
ここで、ポリオールおよびポリアミンのヒドロキシル基、第1級アミノ基および第2級アミノ基の合計に対する、ポリイソシアネートのNCO基のモル比は、1より小さい、
b)式R 2 O−(C=O)−C≡C−R 1 で表される化合物を、ステップa)の中間体と、該中間体のヒドロキシル基、第1級アミノ基および第2級アミノ基の合計に対してモル過剰で反応させること、
ここで、R 1 は水素または1〜12個の炭素原子を有する基を表し、
R 2 は、水素または1〜4個の炭素原子を有する基を表す、
により得ることができる化合物である、請求項1に記載の硬化性組成物。 - ポリオールは、ポリエーテルポリオール、ポリエーテルポリオールブロックコポリマー、ポリエステルポリオール、ポリエステルポリオールブロックコポリマーまたはそれらの混合物を含む群から選択される、請求項2に記載の硬化性組成物。
- ポリオール/ポリアミンの数平均分子量(Mn)は、少なくとも200g/molである、請求項2または3に記載の硬化性組成物。
- ポリイソシアネートは、2,4-トルエンジイソシアネート、2,6-トルエンジイソシアネート、4,4’-ジフェニルメタンジイソシアネート、2,4’−ジフェニルメタンジイソシアネート、2,2’-ジフェニルメタンジイソシアネート、イソホロンジイソシアネート、ヘキサメチレンジイソシアネート、4,4’-メチレンジシクロヘキシルジイソシアネート、2,4’−メチレンジシクロヘキシルジイソシアネート、2,2’-メチレンジシクロヘキシルジイソシアネート、およびそれらの混合物を含む群から選択される、請求項2〜4のいずれかに記載の硬化性組成物。
- 触媒は、第2級または第3級アミンである、請求項1〜5のいずれかに記載の硬化性組成物。
- 触媒は、1,4-ジアザビシクロ[2.2.2]オクタン、テトラメチルエチレンジアミン、N,N-ジイソプロピルエチルアミン、トリエタノールアミン、トリス(2-ピリジルメチル)アミン、トリブチルアミン、4-ジメチルアミノフェノール、N-エチル-N-メチルプロピルアミン、N-メチルピペリジン、N-ブチル-4-ヒドロキシピペリジン、1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン、1,5-ジアザビシクロ[4.3.0]ノナ-5-エン、イミダゾリン、ベンズイミダゾール、ジメチルアミノエタノール、ピロール、モルホリン、ピペリジン、ピペラジン、インドール、およびそれらの混合物からなる群から選択される、請求項1〜5のいずれかに記載の硬化性組成物。
- 触媒は、1,4-ジアザビシクロ[2.2.2]オクタンである、請求項1〜5のいずれかに記載の硬化性組成物。
- 接着剤、コーティング、流延用組成物としての、または、シーラントとしての、請求項1〜8のいずれかに記載の組成物の使用。
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PCT/EP2015/072622 WO2016050878A1 (en) | 2014-09-30 | 2015-09-30 | Nco-free compounds and usage thereof in a curable composition |
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