JP6485726B1 - 合成皮革の製造方法 - Google Patents
合成皮革の製造方法 Download PDFInfo
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- 239000002649 leather substitute Substances 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000012943 hotmelt Substances 0.000 claims abstract description 40
- 239000011342 resin composition Substances 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 22
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 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 4
- 239000002994 raw material Substances 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 8
- 239000003960 organic solvent Substances 0.000 abstract description 7
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- 150000003077 polyols Chemical class 0.000 description 25
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- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 239000006260 foam Substances 0.000 description 2
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- 239000011261 inert gas Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
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- 229920005749 polyurethane resin Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 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 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical group NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical group 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000010985 leather Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
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- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
温度計、撹拌機、不活性ガス導入口、及び還流冷却器を備えた反応容器に、ポリオキシテトラメチレングリコール(数平均分子量;1,000)を250質量部、ポリエステルポリオール(1,6−ヘキサンジオールとアジピン酸との反応物、数平均分子量;2,000)を250質量部を仕込み、減圧条件下で水分含有率が0.05質量%以下となるまで脱水した。
次いで、4,4’−ジフェニルメタンジイソシアネートを133質量部を加え、110℃まで昇温して、イソシアネート基含有率が一定となるまで約2時間反応させて、ウレタンプレポリマー(A−1)を得た。
ウレタンプレポリマー(A−1)を110℃で溶融後、ロールコーターにセットした離型紙上に、0.2kg/m2の量で塗布した後、タックのある状態でウレタン樹脂を含浸した不織布(以下、「含浸不織布」と略記する。)と貼り合わせて温度23℃、湿度50%RHの雰囲気下で2日間放置して合成皮革を得た。
塗布量、及び/又は基材を表1〜2に示す通りに変更した以外は実施例1と同様にして合成皮革を得た。
ウレタンプレポリマー(A−1)を110℃で溶融後、ロールコーターにセットした熱可塑性ウレタンフィルム(以下「TPU」と略記する。)上に、0.2kg/m2の量で塗布した後、温度23℃、湿度50%RHの雰囲気下で2日間放置して合成皮革を得た。
温度計、撹拌機、不活性ガス導入口、及び還流冷却器を備えた反応容器に、ポリオキシ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、ポリエステルポリオール(1,6−ヘキサンジオール、ネオペンチルグリコール、及びアジピン酸の反応物、数平均分子量;2,000)を100質量部を仕込み、減圧条件下で水分含有率が0.05質量%以下となるまで脱水した。
次いで、4,4’−キシリレンジイソシアネートを99質量部を加え、80℃まで昇温して、イソシアネート基含有率が一定となるまで約6時間反応させて、ウレタンプレポリマー(A−2)を得た。
実施例、及び、比較例で得られた合成皮革の外観を目視観察し、以下のように評価した。
「○」:湿気硬化型ウレタンホットメルト樹脂組成物の硬化物層が透明で下地基材が良く見える。
「×」:湿気硬化型ウレタンホットメルト樹脂組成物の硬化物層が濁っている。
実施例、及び、比較例で得られた合成皮革を手で揉み、以下のように評価した。
「○」:柔らかく、ボリューム感がある。
「×」:硬い、又は、ボリューム感が感じられない。
実施例、及び、比較例で得られた合成皮革を株式会社東洋精機製作所製「MIT屈曲試験機」を使用し、常温(23℃)で10万回の屈曲試験を行い、表面に亀裂が入らなければ「○」、試験途中で亀裂が入った場合は「×」と評価した。
実施例、及び、比較例で得られた合成皮革において、湿気硬化型ウレタンホットメルト樹脂組成物の硬化物層上に、ホットメルト布テープを130℃に5秒かけて接着した後に、テンシロン(オリエンテック株式会社製テンシロン万能試験機「RTC−1210A」)を使用して、クロスヘッド測度;200mm/分の条件で剥離強度を測定し、常態での剥離強度とした。2kg/cm以上のものは「○」、それ以外のものは「×」と評価した。
Claims (2)
- 湿気硬化型ウレタンホットメルト樹脂組成物の硬化物層を有する合成皮革の製造方法であって、
前記湿気硬化型ウレタンホットメルト樹脂組成物が、イソシアネート基を有するウレタンプレポリマーを含有し、かつ、水酸基及び/又はアミノ基を有する架橋剤を含有しないものであり、
前記イソシアネート基を有するウレタンプレポリマーが、ジフェニルメタンジイソシアネートを原料とするものであり、かつ、水酸基含有(メタ)アクリレートを原料としないものであり、
前記湿気硬化型ウレタンホットメルト樹脂組成物を、基材に対して、0.03〜0.5kg/m2の量を塗布することにより、その硬化物層を形成することを特徴とする合成皮革の製造方法。 - (i)離型基材上に、前記湿気硬化型ウレタンホットメルト樹脂組成物を塗布し、次いで、該塗布面を離型基材以外の基材に貼り合わせること、又は、(ii)前記湿気硬化型ウレタンホットメルト樹脂組成物を離型基材以外の基材に塗布すること、により湿気硬化型ウレタンホットメルト樹脂組成物の硬化物層を形成する請求項1記載の合成皮革の製造方法。
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JP2017183663 | 2017-09-25 | ||
JP2017183663 | 2017-09-25 | ||
PCT/JP2018/029887 WO2019058804A1 (ja) | 2017-09-25 | 2018-08-09 | 合成皮革の製造方法 |
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JP6485726B1 true JP6485726B1 (ja) | 2019-03-20 |
JPWO2019058804A1 JPWO2019058804A1 (ja) | 2019-11-14 |
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Cited By (1)
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EP4079779A1 (en) | 2021-04-21 | 2022-10-26 | Asahi Kasei Kabushiki Kaisha | Polyol composition |
Citations (7)
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WO2005083173A1 (ja) * | 2004-02-26 | 2005-09-09 | Dainippon Ink And Chemicals, Inc. | 皮革様シートの製造方法 |
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EP4079779A1 (en) | 2021-04-21 | 2022-10-26 | Asahi Kasei Kabushiki Kaisha | Polyol composition |
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