JP6304467B1 - セミipn型複合体の製造方法 - Google Patents
セミipn型複合体の製造方法 Download PDFInfo
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- JP6304467B1 JP6304467B1 JP2017560828A JP2017560828A JP6304467B1 JP 6304467 B1 JP6304467 B1 JP 6304467B1 JP 2017560828 A JP2017560828 A JP 2017560828A JP 2017560828 A JP2017560828 A JP 2017560828A JP 6304467 B1 JP6304467 B1 JP 6304467B1
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- acrylic monomer
- acrylate
- meth
- polymer
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- 239000002131 composite material Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 239000004814 polyurethane Substances 0.000 claims abstract description 33
- 229920002635 polyurethane Polymers 0.000 claims abstract description 33
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 20
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 11
- 125000003368 amide group Chemical group 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000010408 film Substances 0.000 description 27
- 239000005056 polyisocyanate Substances 0.000 description 25
- 229920001228 polyisocyanate Polymers 0.000 description 25
- -1 polyoxyethylene Polymers 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 150000003077 polyols Chemical class 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 17
- 229920005862 polyol Polymers 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000004793 Polystyrene Substances 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000000835 fiber Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- 239000002649 leather substitute Substances 0.000 description 13
- 239000004744 fabric Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 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 10
- 239000000463 material Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000004970 Chain extender Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 9
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 9
- 230000035699 permeability Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000007869 azo polymerization initiator Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007877 V-601 Substances 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000003373 anti-fouling effect Effects 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-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
- 229920002972 Acrylic fiber Polymers 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 3
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920006221 acetate fiber Polymers 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 235000009120 camo Nutrition 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000005607 chanvre indien Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000011487 hemp Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000747 poly(lactic acid) Polymers 0.000 description 3
- 239000004626 polylactic acid Substances 0.000 description 3
- 229920006306 polyurethane fiber Polymers 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- YPQKTLPPOXNDMC-UHFFFAOYSA-N isocyanic acid;methylcyclohexane Chemical compound N=C=O.CC1CCCCC1 YPQKTLPPOXNDMC-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 229920002857 polybutadiene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
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- 210000002374 sebum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
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- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 1
- KQSKOJFWRUTJAE-UHFFFAOYSA-N (2-cyanophenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C#N KQSKOJFWRUTJAE-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- UKPSAIWEFPZIGN-UHFFFAOYSA-N (3-cyanophenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(C#N)=C1 UKPSAIWEFPZIGN-UHFFFAOYSA-N 0.000 description 1
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- QZTSARXNYCUCRQ-UHFFFAOYSA-N (4-cyanophenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=C(C#N)C=C1 QZTSARXNYCUCRQ-UHFFFAOYSA-N 0.000 description 1
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- FHDKOYJQTNVJSJ-UHFFFAOYSA-N 1,1-dicyanoethyl prop-2-enoate Chemical compound C(C=C)(=O)OC(C)(C#N)C#N FHDKOYJQTNVJSJ-UHFFFAOYSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- JFRQLKNEDLLXOQ-UHFFFAOYSA-N 1,3-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1N=C=O JFRQLKNEDLLXOQ-UHFFFAOYSA-N 0.000 description 1
- BQHPNDYUVBBCQF-UHFFFAOYSA-N 1,3-diisocyanato-5-methylbenzene Chemical compound CC1=CC(N=C=O)=CC(N=C=O)=C1 BQHPNDYUVBBCQF-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
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- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- AXTADRUCVAUCRS-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCN1C(=O)C=CC1=O AXTADRUCVAUCRS-UHFFFAOYSA-N 0.000 description 1
- BHPDNFUVYQFFNK-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrole-2,5-dione Chemical compound OCN1C(=O)C=CC1=O BHPDNFUVYQFFNK-UHFFFAOYSA-N 0.000 description 1
- KTCCGEXQRZSXIJ-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1OC1 KTCCGEXQRZSXIJ-UHFFFAOYSA-N 0.000 description 1
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度0.4質量%のテトラヒドロフラン溶液)
標準試料:下記の標準ポリスチレンを用いて検量線を作成した。
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(新中村化学工業株式会社製「AM−90G」、オキシエチレン基の平均付加モル数が9モル)/3−メタクリロキシプロピルメチルジエトキシシランの混合物(モル比=71/24/5)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−1)を得た。得られた重合物(B−1)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−90G)/3−メタクリロキシプロピルメチルジエトキシシランの混合物(モル比=68/22/10)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−2)を得た。得られた重合物(B−2)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−90G)/3−メタクリロキシプロピルトリエトキシシランの混合物(モル比=71/24/5)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−3)を得た。得られた重合物(B−3)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−90G)/3−メタクリロキシプロピルトリエトキシシランの混合物(モル比=68/22/10)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−4)を得た。得られた重合物(B−4)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−90G)/3−メタクリロキシプロピルトリメトキシシランの混合物(モル比=71/24/5)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−5)を得た。得られた重合物(B−5)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−90G)/3−メタクリロキシプロピルトリメトキシシランの混合物(モル比=68/22/10)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−6)を得た。得られた重合物(B−6)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(新中村化学工業株式会社製「AM−130G」、オキシエチレン基の平均付加モル数が13モル)/3−メタクリロキシプロピルメチルジエトキシシランの混合物(モル比=71/24/5)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−7)を得た。得られた重合物(B−7)の重量平均分子量は2万、固形分は50質量%であった。
攪拌機、温度計及び窒素ガス導入管を備えた反応装置に、2−プロパノールを仕込み、その後、N,N−ジメチルアクリルアミド/メトキシポリエチレングリコールアクリレート(AM−130G)/3−メタクリロキシプロピルメチルジエトキシシランの混合物(モル比=68/22/10)と、和光純薬工業株式会社製アゾ系重合開始剤「V−601」を2質量%とを加え、80℃の反応装置内に6時間反応し、重合物(B−8)を得た。得られた重合物(B−8)の重量平均分子量は2万、固形分は50質量%であった。
ジフェニルメタンジイソシアネートを原料としたポリエステル系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;20質量%、以下「MDI/PEs系Pu」と略記する。)100質量部に、重合物(B−1)を30質量部、酸触媒としてリン酸を0.5質量部添加して、5時間反応させてセミIPN型複合体を得た。
用いるポリウレタン(A)、重合物(B)の種類及び/又は量を表1〜2に示す通りに変更した以外は、実施例1と同様にしてセミIPN型複合体を得た。
ジフェニルメタンジイソシアネートを原料とした親水性ポリエーテル/ポリエステル共重合系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;30質量%)で以下の評価を行った。
4,4’−ジシクロヘキシルメタンジイソシアネートを原料とした親水性ポリエーテル/ポリカーボネート共重合系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;25質量%)で以下の評価を行った。
実施例得られたセミIPN型複合体100質量部、及び比較例で使用するポリウレタン100質量部に、それぞれN,N−ジメチルホルムアミド30質量部を加え希釈し、乾燥後の厚さが15μmとなるように離型紙上に塗布した。これを乾燥機にて70℃で2分間、次いで120℃で2分間乾燥させ、評価用皮膜を得た。
全ての評価用皮膜を、2cm(縦)×5cm(横)に裁断したものを試験片とした。得られた試験片を25℃のイオン交換水中に1時間浸漬し、取出した皮膜の横方向の長さを測定し、下記式(1)により耐水膨潤率(%)を算出した。
耐水膨潤率(%)=浸漬後の透湿フィルム及びフィルムの長さ(cm)−5(cm)/5(cm)×100 (1)
実施例1〜8で得られたセミIPN型複合体で作製した評価用皮膜、及び、比較例1のポリウレタン(A)で作製した評価用皮膜を、JISL1099:2012のB−1法(酢酸カリウム法)に準拠して透湿度(g/m2/24h)を測定した。
実施例9〜18で得られたセミIPN型複合体で作製した評価用皮膜、及び、比較例2のポリウレタン(A)で作製した評価用皮膜を、協和界面科学株式会社製の温度計測ユニット(DM)付きの「DropMaster700」(固液界面解析システムオプション)を使用して水に対する接触角を測定した。
実施例9〜18で得られたセミIPN型複合体で作製した評価用皮膜、及び、比較例のポリウレタン(A)で作製した評価用皮膜を、振磨耗試験機の摩擦面に貼り付け、摩擦子には黒染み試験布(Swissatest社製「EMPA104」)を貼り付け、1kg荷重で100回往復試験を行った。次いで試験片を純水で湿らせたBEMCOTでふき取った際の黒染みの有無で以下のように評価した。
「○」;黒染みが完全にふき取られている
「△」;黒染みが一部残っている
「×」;黒染みが全くふき取れない
「MDI/PEs系Pu」:ジフェニルメタンジイソシアネートを原料としたポリエステル系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;20質量%)
「MDI/PEs・PEt系Pu」:ジフェニルメタンジイソシアネートを原料とした親水性ポリエーテル/ポリエステル共重合系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;30質量%)
「H12MDI/PC系Pu」:4,4’−ジシクロヘキシルメタンジイソシアネートを原料としたポリカーボネート系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;25質量%)
「H12MDI/PC・PEt系Pu」:4,4’−ジシクロヘキシルメタンジイソシアネートを原料とした親水性ポリエーテル/ポリカーボネート共重合系ウレタンのN,N−ジメチルホルムアミド溶液(固形分;25質量%)
「DMAA」:N,N−ジメチルアクリルアミド
「KBE−502」:3−メタクリロキシプロピルメチルジエトキシシラン
「KBE−503」:3−メタクリロキシプロピルトリエトキシシラン
「KBM−503」:3−メタクリロキシプロピルトリメトキシシラン
Claims (3)
- ポリウレタン(A)と、アミド基を有するアクリルモノマー(b1−1)、及び、オキシエチレン基を有するアクリルモノマー(b1−2)を含有する親水性アクリルモノマー(b1)並びに加水分解性シリル基を有するアクリルモノマー(b2)の重合物(B)とを、混合し、前記重合物(B)を架橋させることを特徴とするセミIPN型複合体の製造方法。
- 前記アミド基を有するアクリルモノマー(b1−1)、オキシエチレン基を有するアクリルモノマー(b1−2)、及び、加水分解性シリル基を有するアクリルモノマー(b2)の重合比率(モル比)が、(b1−1)/(b1−2)/(b2)=50/49.5/0.5〜89/1/10の範囲である請求項1記載のセミIPN型複合体の製造方法。
- 前記重合物(B)の配合量が、前記ポリウレタン(A)100質量部に対して、10〜70質量部の範囲である請求項1又は2記載のセミIPN型複合体の製造方法。
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WO2017082010A1 (ja) * | 2015-11-11 | 2017-05-18 | Dic株式会社 | セミipn型複合体の製造方法、及び、合成皮革の製造方法 |
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