JPWO2019235125A1 - 合成皮革 - Google Patents
合成皮革 Download PDFInfo
- Publication number
- JPWO2019235125A1 JPWO2019235125A1 JP2019562006A JP2019562006A JPWO2019235125A1 JP WO2019235125 A1 JPWO2019235125 A1 JP WO2019235125A1 JP 2019562006 A JP2019562006 A JP 2019562006A JP 2019562006 A JP2019562006 A JP 2019562006A JP WO2019235125 A1 JPWO2019235125 A1 JP WO2019235125A1
- Authority
- JP
- Japan
- Prior art keywords
- urethane resin
- mass
- synthetic leather
- parts
- preferable
- 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
- 239000002649 leather substitute Substances 0.000 title claims abstract description 40
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 146
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 48
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 48
- 239000010410 layer Substances 0.000 claims abstract description 43
- 239000012790 adhesive layer Substances 0.000 claims abstract description 37
- 239000002994 raw material Substances 0.000 claims abstract description 29
- 125000000129 anionic group Chemical group 0.000 claims abstract description 27
- 239000011342 resin composition Substances 0.000 claims abstract description 26
- 239000000758 substrate Substances 0.000 claims abstract description 11
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 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 7
- 239000012875 nonionic emulsifier Substances 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 5
- 239000010985 leather Substances 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 93
- -1 polyoxyethylene Polymers 0.000 description 54
- 150000003077 polyols Chemical class 0.000 description 39
- 229920005862 polyol Polymers 0.000 description 37
- 238000000034 method Methods 0.000 description 33
- 210000003491 skin Anatomy 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- 239000004970 Chain extender Substances 0.000 description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000004793 Polystyrene Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 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 6
- 238000007664 blowing Methods 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000006353 oxyethylene group Chemical group 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 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 5
- 229920000570 polyether Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002344 surface layer Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 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
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
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- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 2
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 2
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- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
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- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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Abstract
Description
(1)基材(i)、接着層(ii)、表皮層(iii)
(2)基材(i)、接着層(ii)、中間層、表皮層(iii)
(3)基材(i)、多孔層、接着層(ii)、表皮層(iii)
(4)基材(i)、多孔層、接着層(ii)、中間層、表皮層(iii)
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(旭化成ケミカルズ株式会社製「DURANOL T5652」数平均分子量:2,000)500質量部、2,2−ジメチロールプロピオン酸(以下「DMPA」と略記する。)8質量部、メチルエチルケトン394質量部を加え、均一に混合した後、トルエンジイソシアネート(以下「TDI」と略記する。)68質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、1,3−ブタンジオールを14質量部加え、70℃で約1時間反応させて反応を終了させ、ウレタンポリマーのメチルエチルケトン溶液を得た。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にトリエチルアミン6質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水886質量部を加えた後、メチルエチルケトンを減圧下留去することによって、接着層形成用ウレタン樹脂(A−1)組成物(不揮発分;40質量%、アニオン性基(カルボキシル基、以下同じ。)の濃度;0.11mmol/g、重量平均分子量;29,000、芳香環の濃度;0.67mol/kg)を得た。
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリテトラメチレングリコール(数平均分子量:2,000)500質量部、エチレングリコール3質量部、DMPA12質量部、メチルエチルケトン403質量部を加え、均一に混合した後、TDI79質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、1,3−BGを11質量部加え、70℃で約1時間反応させて反応を終了させ、ウレタンポリマーのメチルエチルケトン溶液を得た。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にトリエチルアミン9質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水907質量部を加えた後、メチルエチルケトンを減圧下留去することによって、接着層形成用ウレタン樹脂(A−2)組成物(不揮発分;40質量%、重量平均分子量;46,000、アニオン性基の濃度;0.15mmol/g、芳香環の濃度;0.75mol/kg)を得た。
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリプロピレングリコール(数平均分子量:2,000)500質量部、1,4−ブタンジオール9質量部、DMPA10質量部、メチルエチルケトン400質量部を加え、均一に混合した後、TDI78質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、1,3−BGを4質量部加え、70℃で約1時間反応させて反応を終了させ、ウレタンポリマーのメチルエチルケトン溶液を得た。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にN,N−ジメチルエタノールアミン7質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水901質量部を加えた後、メチルエチルケトンを減圧下留去することによって、接着層形成用ウレタン樹脂(A−3)組成物(不揮発分;40質量%、アニオン性基の濃度;0.13mmol/g、重量平均分子量;68,000、芳香環の濃度;0.74mol/kg)を得た。
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリテトラメチレングリコール(数平均分子量:1,000)500質量部、DMPA15質量部、メチルエチルケトン428質量部を加え、均一に混合した後、TDI117質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、1,3−ブタンジオールを11質量部加え、70℃で約1時間反応させて反応を終了させ、ウレタンポリマーのメチルエチルケトン溶液を得た。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にN,N−ジメチルエタノールアミン10質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水964質量部を加えた後、メチルエチルケトンを減圧下留去することによって、接着層形成用ウレタン樹脂(A−4)組成物(不揮発分;40質量%、アニオン性基の濃度;0.17mmol/g、重量平均分子量;55,000、芳香環の濃度;1.05mol/kg)を得た。
メチルエチルケトン3,281質量部及びオクチル酸第一錫0.1質量部の存在下、ポリカーボネートポリオール(日本ポリウレタン株式会社製「ニッポラン980R」、数平均分子量;2,000)1,000質量部と、DMPA17質量部と、エチレングリコール47質量部と、ジフェニルメタンジイソシアネート(以下、「MDI」と略記する。)344質量部と、を溶液粘度が20,000mPa・sに達するまで70℃で反応させた後、メタノール3質量部を加えて反応を停止させてウレタン樹脂のメチルエチルケトン溶液を得た。このウレタン樹脂溶液に、ポリオキシエチレンジスチレン化フェニルエーテル(Hydrophile−Lipophile Balance(以下、「HLB」と略記する);14、オキシエチレン基の平均付加モル数;10、以下、「(Y−1)」と略記する。)70質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水800質量部を加えて転相乳化させることで前記ウレタン樹脂(X−1)が水に分散した乳化液を得た。
次いで、前記乳化液からメチルエチルケトンを留去することによって、不揮発分;40質量%、芳香環の含有量;1.95mol/kgの表皮層形成用ウレタン樹脂(X−1)組成物を得た。
メチルエチルケトン3,281質量部及びオクチル酸第一錫0.1質量部の存在下、ポリエーテルポリオール(三菱化型株式会社製「PTMG2000」、数平均分子量;2,000)1,000質量部と、DMPA17質量部と、エチレングリコール47質量部と、MDI344質量部とを溶液粘度が20,000mPa・sに達するまで70℃で反応させた後、メタノール3質量部を加えて反応を停止させてウレタン樹脂のメチルエチルケトン溶液を得た。このウレタン樹脂溶液に(Y−1)70質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水800質量部を加えて転相乳化させることで前記ウレタン樹脂(X−2)が水に分散した乳化液を得た。
次いで、前記乳化液からメチルエチルケトンを留去することによって、不揮発分;40質量%、芳香環の含有量;1.95mol/kgの表皮層形成用ウレタン樹脂(X−2)組成物を得た。
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリテトラメチレングリコール(数平均分子量;1,000)を500質量部、DMPA15質量部、メチルエチルケトン450質量部を加え、均一に混合した後、イソホロンジイソシアネート(以下「IPDI」と略記する。)149質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、1,3−BGを11質量部加え、70℃で1時間反応させ、ウレタンプレポリマーのメチルエチルケトン溶液を得た。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にN,N−ジメチルエタノールアミン10質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水1,012質量部を加えた。反応終了後、メチルエチルケトンを減圧下留去することによって、接着層形成用ウレタン樹脂(AR−1)組成物(不揮発分;40質量%、アニオン性基の濃度;0.16mmol/g、重量平均分子量;28,000、芳香環の濃度;0mol/kg)を得た。
撹拌機、還流冷却管、温度計及び窒素吹き込み管を備えた4ツ口フラスコに、窒素気流下、ポリカーボネートジオール(旭化成ケミカルズ株式会社製「DURANOL T5652」数平均分子量:2,000)100質量部、ポリテトラメチレングリコール(数平均分子量;1,000)を100質量部、DMPA20質量部、メチルエチルケトン151質量部を加え、均一に混合した後、IPDI133質量部を加え、次いでジブチル錫ジラウレート0.1質量部を加え、70℃で約4時間反応させた。次いで、前記方法で得られたウレタンポリマーのメチルエチルケトン溶液にトリエチルアミン15質量部を加え、前記ウレタンポリマー中のカルボキシル基を中和した後、イオン交換水683質量部を加えた後、80%水加ヒドラジン15質量部を加え、反応させた。反応終了後、メチルエチルケトンを減圧下留去することによって、表皮層形成用ウレタン樹脂(XR−1)組成物(不揮発分;35質量%、尿素結合の濃度;2.6mol/kg、芳香環の濃度;0mol/kg)を得た。
合成例5で得られた表皮層形成用ウレタン樹脂(X−1)組成物100質量部、水分散性黒色顔料(DIC株式会社製「ダイラックHS−9530」)を10質量部、会合型増粘剤(DIC株式会社製「ハイドラン アシスター T10」)を1質量部からなる配合液をフラット離型紙(味の素株式会社製「DN−TP−155T」)上に乾燥後の膜厚が30μmとなる様に塗布し、70℃で2分間、さらに120℃で2分間乾燥させた。
次いで、合成例1で得られた接着層形成用ウレタン樹脂(A−1)組成物100質量部、会合型増粘剤(DIC株式会社製「ハイドラン アシスター T10」)を1質量部、ポリイソシアネート系架橋剤(DIC株式会社製「ハイドラン アシスター C5」)を9質量部からなる配合液を乾燥後の膜厚が50μmとなるように塗布し、70℃で3分間乾燥させた。乾燥後直ちにポリウレタン含浸不織布を貼り合わせた後、120℃で2分間熱処理し、50℃で2日間熟成させてから離型紙を剥離して合成皮革を得た。
用いる表皮層形成用ウレタン樹脂組成物、接着層形成用ウレタン樹脂組成物の種類を表1〜3に変更した以外は、実施例1と同様にして合成皮革を得た。
合成例で用いたポリオールの数平均分子量、及び、合成例で得られたウレタン樹脂の重要平均分子量は、ゲル・パーミエーション・カラムクロマトグラフィー(GPC)法により、下記の条件で測定し得られた値を示す。
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」
実施例及び比較例で得られた合成皮革を、島津オートグラフ「AG−1」(株式会社島津製作所製)を使用して、フルスケール5kg、ヘッドスピード20mm/分の条件にて剥離強度を測定し、以下のように評価した。
「A」;0.15MPa以上
「B」;0.1MPa以上0.15MPa未満
「C」;0.1MPa未満
実施例及び比較例で得られた合成皮革の表皮層上に、表皮層と同重量のオレイン酸を染み込ませた濾紙を載置し、80℃の条件下で24時間放置した。その後、濾紙を取り除き、ウエスでオレイン酸を拭き取った後、外観を観察し、以下のように評価した。
「A」;外観に変化無し
「B」;外観にごく一部の膨潤が確認されたが、表皮層の剥離はなかった。
「C」;外観に明確に確認できる膨潤が確認されたが、表皮層の剥離はなかった。
「D」;外観に明確に確認できる膨潤が確認され、表皮層の部分的剥離が確認された。
実施例及び比較例で得られた合成皮革を70℃、湿度95%の条件下で5週間放置した。その後の外観観察および指触により、以下のように評価した。
「A」;外観・指触に異常なし。
「B」;外観に艶変化が生じたが、指触では異常は確認されなかった。
「C」;外観に艶変化が生じ、かつ、ベタツキが確認された。
実施例及び比較例で得られた合成皮革を、650ppmのNOxガスに1時間暴露し、暴露後の黄変度を目視観察し、以下のように評価した。
「A」;外観に変化なし。
「B」;外観に軽度の黄変が確認される。
「C」;外観に大きな黄変が確認される。
Claims (10)
- 少なくとも、基材(i)、接着層(ii)、及び、表皮層(iii)を有する合成皮革であって、
前記接着層(ii)と表皮層(iii)とが、ともに、芳香族ポリイソシアネートを原料とするウレタン樹脂、及び、水を含有するウレタン樹脂組成物により形成されたものであることを特徴とする合成皮革。 - 前記接着層(ii)を形成するウレタン樹脂組成物が、芳香族ポリイソシアネート(a1)と原料とするウレタン樹脂(A)、及び、水(B)を含有するものである請求項1記載の合成皮革。
- 前記芳香族ポリイソシアネート(a1)が、トルエンジイソシアネートを含むものである請求項2記載の合成皮革。
- 前記ウレタン樹脂(A)がアニオン性基を有するものであり、そのアニオン性基の濃度が、0.35mmol/g以下である請求項2又は3記載の合成皮革。
- 前記ウレタン樹脂(A)中の芳香環の濃度が、0.1〜2.5mol/kgの範囲である請求項2〜4のいずれか1項記載の合成皮革。
- 前記ウレタン樹脂(A)の重量平均分子量が、2,000〜150,000の範囲である請求項2〜5のいずれか1項記載の合成皮革。
- 前記表皮層(iii)を形成するウレタン樹脂組成物が、芳香族ポリイソシアネート(x1)と原料とするウレタン樹脂(X)、ノニオン性乳化剤(Y)、及び、水(Z)を含有するものである請求項1〜6のいずれか1項記載の合成皮革。
- 前記芳香族ポリイソシアネート(x1)が、ジフェニルメタンジイソシアネートである請求項7記載の合成皮革。
- 前記ウレタン樹脂(X)中の尿素結合の濃度が、1.2mol/kg以下である請求項7又は8記載の合成皮革。
- 前記ウレタン樹脂(X)中の芳香環の濃度が、0.1〜50mol/kgの範囲である請求項7〜9のいずれか1項記載の合成皮革。
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