JP2017014663A - 熱応答性液晶エラストマーを含む単繊維、フィラメント糸、繊維製品 - Google Patents
熱応答性液晶エラストマーを含む単繊維、フィラメント糸、繊維製品 Download PDFInfo
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- JP2017014663A JP2017014663A JP2015132560A JP2015132560A JP2017014663A JP 2017014663 A JP2017014663 A JP 2017014663A JP 2015132560 A JP2015132560 A JP 2015132560A JP 2015132560 A JP2015132560 A JP 2015132560A JP 2017014663 A JP2017014663 A JP 2017014663A
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- 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 1
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- 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 description 1
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- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- RTWAGNSZDMDWRF-UHFFFAOYSA-N [1,2,2-tris(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1(CO)CO RTWAGNSZDMDWRF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 238000004898 kneading Methods 0.000 description 1
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- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
Classifications
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/70—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
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- D10B2401/04—Heat-responsive characteristics
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2501/00—Wearing apparel
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
【解決手段】 本発明の単繊維は、液晶相から等方相へ、又は等方相から液晶相へ相転移する転移温度(Ti)を境に、可逆的に伸縮する熱応答性液晶エラストマーを含む。
【選択図】 なし
Description
(式中、Xは活性水素基であり、R1は単結合、−N=N−、−CO−、−CO−O−、又は−CH=N−であり、R2は単結合、又は−O−であり、R3は単結合、又は炭素数1〜20のアルキレン基である。ただし、R2が−O−であり、かつR3が単結合である場合を除く。)
(式中、Xは活性水素基であり、R1は単結合、−N=N−、−CO−、−CO−O−、又は−CH=N−であり、R2は単結合、又は−O−であり、R3は単結合、又は炭素数1〜20のアルキレン基である。ただし、R2が−O−であり、かつR3が単結合である場合を除く。)
(液晶性ウレタン化合物及び熱応答性液晶ポリウレタンエラストマーのガラス転移温度(Tg)、メソゲンの融点(Tm)、及び液晶相から等方相への転移温度(Ti)の測定)
Tg、Tm、及びTiは、示差走査熱量分析器DSC(株式会社日立ハイテクサイエンス社製、商品名:X−DSC 7000)を用いて、20℃/分の条件で測定した。
液晶性ウレタン化合物の粘度は、キャピラリーレオメーター(安田精機製、商品名:セミオートマチックキャピラリーレオメーター(SAS-2002))を用い、JIS K 7199に準拠して、60℃、せん断速度1000sec-1で測定した。
液晶性ウレタン化合物及び熱応答性液晶ポリウレタンエラストマーの液晶性の有無は、偏光顕微鏡(ニコン社製、商品名:LV−100POL)及び示差走査熱量分析器DSC(株式会社日立ハイテクサイエンス社製、商品名:X−DSC 7000)を用いて、20℃/分の条件で評価した。
伸縮率は、単繊維の転移温度(Ti)前後の長さを測定し、下記式により算出した。
伸縮率(%)=(L1/L2)×100
L1:転移温度(Ti)未満での繊維長
L2:転移温度(Ti)以上での繊維長
なお、実施例のサンプルについては、L1は10℃での繊維長を採用し、L2は80℃での繊維長を採用した。
単繊維の伸縮力(締付力)は、転移温度(Ti)前後の繊維長変化時に発生する応力を、恒温槽付きの引張試験機を用いて測定した。詳しくは、0℃に温度調節された槽内で、チャック間に、単繊維サンプルをたるまないようにセットし、転移温度以上に昇温(Ti+10℃)させた時の発生応力(kPa)を測定した。
反応容器にBH6(500g)、KOH19.0g、及びDMF3000mlを入れて混合し、その後、プロピレンオキシドをBH6(1モル)に対して5当量添加し、加圧条件下で120℃で2時間反応させた。その後、シュウ酸15.0gを添加して付加反応を停止させ、吸引ろ過により塩を除去し、さらにDMFを減圧蒸留により除去して、目的物であるメソゲンジオールA(構造異性体を含んでいてもよい)を得た。当該反応を下記に示す。
反応容器にBH6(500g)、KOH19.0g、及びDMF3000mlを入れて混合し、その後、プロピレンオキシドをBH6(1モル)に対して4当量添加し、加圧条件下で120℃で2時間反応させた。その後、シュウ酸15.0gを添加して付加反応を停止させ、吸引ろ過により塩を除去し、さらにDMFを減圧蒸留により除去して、目的物であるメソゲンジオールB(構造異性体を含んでいてもよい)を得た。
延伸倍率を300%に変更した以外は実施例2と同様の方法で単繊維を製造した。
反応容器にBH6(500g)、KOH19.0g、及びDMF3000mlを入れて混合し、その後、プロピレンオキシドをBH6(1モル)に対して3当量添加し、加圧条件下で120℃で2時間反応させた。その後、シュウ酸15.0gを添加して付加反応を停止させ、吸引ろ過により塩を除去し、さらにDMFを減圧蒸留により除去して、目的物であるメソゲンジオールC(構造異性体を含んでいてもよい)を得た。
延伸倍率を300%に変更した以外は実施例4と同様の方法で単繊維を製造した。
反応容器にBH4(500g)、KOH19.0g、及びDMF3000mlを入れて混合し、その後、プロピレンオキシドをBH4(1モル)に対して3当量添加し、加圧条件下で120℃で2時間反応させた。その後、シュウ酸15.0gを添加して付加反応を停止させ、吸引ろ過により塩を除去し、さらにDMFを減圧蒸留により除去して、目的物であるメソゲンジオールD(構造異性体を含んでいてもよい)を得た。当該反応を下記に示す。
Claims (12)
- 液晶相から等方相へ、又は等方相から液晶相へ相転移する転移温度(Ti)を境に、可逆的に伸縮する熱応答性液晶エラストマーを含む単繊維。
- 前記熱応答性液晶エラストマーは、少なくとも、活性水素基を有するメソゲン基含有化合物、アルキレンオキシド及び/又はスチレンオキシド、及びジイソシアネート化合物を反応させて得られる液晶性ウレタン化合物と、当該液晶性ウレタン化合物の活性水素基又はイソシアネート基と反応する3官能以上の多官能化合物とを反応させることにより得られる熱応答性液晶ポリウレタンエラストマーである請求項1に記載の単繊維。
- 前記アルキレンオキシドは、エチレンオキシド、プロピレンオキシド、及びブチレンオキシドからなる群より選択される少なくとも1種である請求項2又は3に記載の単繊維。
- 前記アルキレンオキシド及び/又はスチレンオキシドは、前記メソゲン基含有化合物1モルに対して2〜10モル付加している請求項2〜4のいずれかに記載の単繊維。
- 前記熱応答性液晶ポリウレタンエラストマーは、ガラス転移温度(Tg)と前記転移温度(Ti)の温度間にメソゲンの融点が存在せず、TgとTiの温度間で液晶が発現する請求項2〜5のいずれかに記載の単繊維。
- 前記転移温度(Ti)が、0〜100℃である請求項1〜6のいずれかに記載の単繊維。
- 前記転移温度(Ti)が、20〜35℃である請求項1〜6のいずれかに記載の単繊維。
- 伸縮率が102〜300%である請求項1〜8のいずれかに記載の単繊維。
- 請求項1〜9のいずれかに記載の単繊維を含むフィラメント糸。
- 請求項1〜9のいずれかに記載の単繊維、又は請求項10に記載のフィラメント糸を用いた繊維製品。
- 伸縮率が異なる2種以上の単繊維又はフィラメント糸を用いて、部分ごとに伸縮度合いを変化させた請求項11に記載の繊維製品。
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JP2019090137A (ja) * | 2017-11-16 | 2019-06-13 | Toyo Tire株式会社 | 熱応答性布帛 |
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