JP6938771B2 - ポリウレタンゲル材料、ポリウレタンゲル、疑似生体材料、および、ポリウレタンゲルの製造方法 - Google Patents
ポリウレタンゲル材料、ポリウレタンゲル、疑似生体材料、および、ポリウレタンゲルの製造方法 Download PDFInfo
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- JP6938771B2 JP6938771B2 JP2020512253A JP2020512253A JP6938771B2 JP 6938771 B2 JP6938771 B2 JP 6938771B2 JP 2020512253 A JP2020512253 A JP 2020512253A JP 2020512253 A JP2020512253 A JP 2020512253A JP 6938771 B2 JP6938771 B2 JP 6938771B2
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- polyurethane gel
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- 238000006243 chemical reaction Methods 0.000 claims description 60
- 125000001931 aliphatic group Chemical group 0.000 claims description 51
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- 125000000524 functional group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 43
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- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 3
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- 210000002216 heart Anatomy 0.000 description 1
- 210000000514 hepatopancreas Anatomy 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000244 kidney pelvis Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- YMQPOZUUTMLSEK-UHFFFAOYSA-L lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O YMQPOZUUTMLSEK-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical class O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 210000002990 parathyroid gland Anatomy 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 210000003635 pituitary gland Anatomy 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 210000004994 reproductive system Anatomy 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate 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
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- 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
- C08G2220/00—Compositions for preparing gels other than hydrogels, aerogels and xerogels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
<イソシアネート基濃度(単位:質量%)、イソシアネート基の転化率(単位:質量%)>
電位差滴定装置(京都電子工業社製、型番:AT−510)を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法によりイソシアネート基濃度(イソシアネート基含有率)を測定し、以下の式により、測定試料のイソシアネート基の転化率を算出した。
<イソシアネートモノマー濃度(単位:質量%)>
国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートまたは市販のヘキサメチレンジイソシアネートを標準物質として用い、ジベンジルアミンによりラベル化させ、以下のHPLC測定条件下で得られたクロマトグラムの面積値から作成した検量線により、未反応のイソシアネートモノマー(ペンタメチレンジイソシアネートモノマーまたはヘキサメチレンジイソシアネートモノマー)の濃度を算出した。
ポンプ LC−20AT
デガッサ DGU−20A3
オートサンプラ SIL−20A
カラム恒温槽 COT−20A
検出器 SPD−20A
カラム;SHISEIDO SILICA SG−120
カラム温度;40℃
溶離液;n−ヘキサン/メタノール/1,2−ジクロロエタン=90/5/5(体積比)
流量;0.2mL/min
検出方法;UV 225nm
<粘度(単位:mPa・s)>
東機産業社製のE型粘度計TV−30(ローター角度:1°34’、ローター半径:24cm)を用いて、JIS K5600−2−3(2014年)のコーンプレート粘度計法に準拠して、25℃で測定試料の粘度を測定した。測定時のコーンプレートの回転数は、粘度が高くなるのに合わせて、100rpmから2.5rpmまでの間で順次変更した。
下記の装置および条件にて1H−NMRを測定し、脂肪族ポリイソシアネートにおける、イソシアヌレート基1モルに対するアロファネート基の含有割合(アロファネート基/イソシアヌレート基のモル比率)を以下の式により算出した。なお、化学シフトppmの基準として、D6−DMSO溶媒中のテトラメチルシラン(0ppm)を用いた。
装置; JNM−AL400(JEOL製)
条件; 測定周波数:400MHz、溶媒:D6−DMSO、溶質濃度:5質量%
イソシアヌレート基(イソシアヌレート基に直接結合するメチレン基(CH2基))のプロトンの帰属ピーク(6H):3.8ppm
アロファネート基(アロファネート基内のNH基)のプロトンの帰属ピーク(1H):8.3〜8.7ppm
アロファネート基/イソシアヌレート基(モル比率)=アロファネート基のプロトンの帰属ピークの積分値/(イソシアヌレート基のプロトンの帰属ピークの積分値/6)
<平均イソシアネート基数(平均官能基数)>
脂肪族ポリイソシアネートの平均イソシアネート基数を、イソシアネート基濃度、固形分濃度(NV)、および、以下の装置および条件にて測定されるゲルパーミエーションクロマトグラフィーの数平均分子量から、下記式により算出した。
(式中、Aは、イソシアネート基濃度を示し、Bは、固形分濃度を示し、Cは、数平均分子量を示す。)
装置:HLC−8220GPC(東ソー製)
カラム:TSKgelG1000HXL、TSKgelG2000HXL、およびTSKgelG3000HXL(東ソー製)を直列連結
検出器: 示差屈折率計
測定条件
注入量:100μL
溶離液:テトラヒドロフラン
流量:0.8mL/min
温度:40℃
検量線:106〜22450の範囲の標準ポリエチレンオキシド(東ソー製、商品名:TSK標準ポリエチレンオキシド)
<平均水酸基数(平均官能基数)>
水酸基価を、ポリオキシアルキレンポリオール1g中の水酸基に相当する水酸化カリウムのmg数と定義した。そして、JIS K1557(2007年)6.4項「水酸基価」に従って、ポリオールの水酸基価を測定した。
(1)脂肪族ポリイソシアネート(A)
調製例1(イソシアネート(a−1)(PDIのアルコール変性イソシアヌレート誘導体))
温度計、撹拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネート(以下、PDIとする。)を500質量部、イソブチルアルコールを6.9質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
温度計、撹拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、PDIを500質量部、イソブチルアルコールを0.5質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
温度計、撹拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、PDIを500質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃に加温した。次いで、イソシアヌレート化触媒としてN−(2−ヒドロキシプロピル)−N,N,N−トリメチルアンモニウム−2−エチルヘキサノエートを0.05質量部配合した。
イソシアネート基濃度を測定し、その濃度が49.0質量%(すなわち、転化率10質量%)に至るまで反応を継続した。50分後に所定の転化率(転化率10質量%)に達したところで、o−トルエンスルホンアミドを0.12質量部添加した。得られた反応混合液を薄膜蒸留装置(温度:150℃、真空度:0.093kPa)に通液して未反応のペンタメチレンジイソシアネートモノマーを除去し、さらに、得られたろ物100質量部に対し、o−トルエンスルホンアミドを0.02質量部および塩化ベンゾイルを0.003質量部添加し、PDIのイソシアヌレート誘導体を得た。これを、イソシアネート(a−3)とした。
温度計、撹拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、PDIを500質量部、イソブチルアルコールを0.5質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
温度計、撹拌装置、窒素導入管および冷却管が装着された反応機において、窒素雰囲気下、PDIを1500質量部、イソブタノールを24質量部、2,6−ジ(t−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部装入し、85℃で3時間ウレタン化反応させた。
PDIをヘキサメチレンジイソシアネート(三井化学社製、商品名:タケネート700(以下、HDIとする。))に変更した以外は、調製例1と同じ方法で、HDIのアルコール変性イソシアヌレート誘導体を得た。これを、イソシアネート(a−6)とした。
撹拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、PDIを200質量部装入し、窒素雰囲気下、撹拌しながら95℃まで昇温した。次いで滴下ロートにトリメチロールプロパン(以下、TMPとする。)を21.1質量部仕込み、リボンヒーターにより加熱した。
準備例1(ポリオール(b−1))
ポリオキシアルキレンポリオール(プロピレングリコールにプロピレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=2000、平均官能基数2、水酸基価56mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=0質量%)を、ポリオール(b−1)とした。
ポリオキシアルキレンポリオール(プロピレングリコールにプロピレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=1000、平均官能基数2、水酸基価112mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=0質量%)を、ポリオール(b−2)とした。
数平均分子量2000のポリオール(b−1)と、数平均分子量1000のポリオール(b−2)とを、1:1(b−1:b−2(質量比))となるように混合し、混合物として、ポリオール(b−2−1)を得た。ポリオール(b−2−1)の数平均分子量は約1300(1335)、平均官能基数2、水酸基価84mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度0質量%であった。
数平均分子量2000のポリオール(b−1)と、数平均分子量1000のポリオール(b−2)とを、4:1(b−1:b−2(質量比))となるように混合し、混合物として、ポリオール(b−2−2)を得た。ポリオール(b−2−2)の数平均分子量は約1700(1674)、平均官能基数2、水酸基価67mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度0質量%であった。
ポリオキシアルキレンポリオール(プロピレングリコールにプロピレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=3000、平均官能基数2、水酸基価37mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=0質量%)を、ポリオール(b−3)とした。
ポリオキシアルキレンポリオール(プロピレングリコールにプロピレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=4000、平均官能基数2、水酸基価28mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=0質量%)を、ポリオール(b−4)とした。
ポリオキシアルキレンポリオール(グリセリンにプロピレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=3000、平均官能基数3、水酸基価56mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=0質量%)を、ポリオール(b−5)とした。
ポリオキシアルキレンポリオール(グリセリンにプロピレンオキサイドを付加重合し、次いでエチレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=2000、平均官能基数2、水酸基価56mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=20質量%)を、ポリオール(b−6)とした。
ポリオキシアルキレンポリオール(グリセリンにプロピレンオキサイドを付加重合し、次いでエチレンオキサイドを付加重合したポリエーテルポリオール、数平均分子量(Mn)=2000、平均官能基数2、水酸基価56mgKOH/g、全オキシアルキレン中のエチレンオキサイド濃度=40質量%)を、ポリオール(b−7)とした。
数平均分子量2000のポリテトラメチレンエーテルグリコール(PTMEG、保土谷化学社製、商品名:PTG―2000SN、水酸基価56mgKOH/g、平均官能基数2)を、ポリオール(b−8)とした。
数平均分子量1000のポリテトラメチレンエーテルグリコール(PTMEG、保土谷化学社製、商品名:PTG―1000、水酸基価112mgKOH/g、平均官能基数2)を、ポリオール(b−9)とした。
数平均分子量1800の非晶性ポリテトラメチレンエーテルグリコール(旭化成せんい社製、商品名:PTXG、水酸基価60mgKOH/g、平均官能基数2、テトラヒドロフランとネオペンチルグリコールとの共重合体)を、ポリオール(b−10)とした。
準備例11(可塑剤(c−1))
ジイソノニルシクロヘキサン−1,2−ジカルボキシレート(BASF社製、商品名:Hexamol DINCH、沸点394℃)を、可塑剤(c−1)とした。
ジイソノニルアジペート(三菱ケミカル社製、商品名:DINA、沸点250℃)を、可塑剤(c−2)とした。
ジ−(2−エチルヘキシル)フタレート(三菱ケミカル社製、商品名:DOP、沸点386℃)を、可塑剤(c−3)とした。
クロロパラフィン(SIGMA−ALDRICH社製、商品名:Chloroparaffin)を、可塑剤(c−4)とした。
(4)触媒(d)
東京化成工業社製、試薬 ジブチルチンジラウレート
(5)消泡剤(e)
ビックケミー・ジャパン社製、商品名:BYK−088
3.ポリウレタンゲルの製造
実施例1
表1に示す質量割合で、イソシアネート(a−1)と、ポリオール(b−1)と、可塑剤(c−1)とを準備し、ポリウレタンゲル材料を得た(準備工程)。
・5cm×5cm×高さ15mmの角ブロック金型
・直径29mm×高さ13mmの円柱状金型
このポリウレタンゲルを23℃、相対湿度55%の室内で7日間静置した後、各種物性測定に供した。
表1〜表4に示す処方に変更した以外は、実施例1と同じ方法で、ポリウレタンゲルを得た。
<ポリウレタンゲルの硬化性>
ブロック金型にポリウレタンゲル材料の混合液を流し込み、80℃にて2時間反応させた。その後のポリウレタンゲル材料の流動性を確認し、ポリウレタンゲルの硬化性を評価した。評価の基準を下記する。
2mmシート金型で作成したポリウレタンゲルを、3号形試験片形状に打抜いて測定試料を作製した。測定試料に対して、引張圧縮試験機(インテスコ社製、Model205N)を用いて、JIS K−6400(2012年)に従って引張試験し、破断時における伸びを算出した。
円柱状金型で得られたポリウレタンゲルを、円柱状試験片に打ち抜いて測定試料を作製し、重量を測定した(W1)。
ブロック金型で得られたポリウレタンゲルに、厚み1mm×4cm×4cmのステンレス板(材質:JIS G 4305 SUS304、表面仕上げBA、表面粗度:JIS
B0601 、公差Ra=50±25nm)を乗せ、23℃、相対湿度55%の室内で1日間静置した後、プッシュプルゲージでステンレス板を剥がすときに必要な応力(kgf/16cm2)を測定した。
ブロック金型で得られたポリウレタンゲルのアスカーC硬度を、JIS K 7312(1996年)のタイプC硬さ試験により測定した。
Claims (11)
- 平均官能基数2.3以上3.2以下の脂肪族ポリイソシアネート(A)と、
平均官能基数2.0以上2.3以下のポリオール(B)と、
エステル基を含有する可塑剤(C)と
を含有するポリウレタンゲル材料であって、
前記脂肪族ポリイソシアネート(A)は、脂肪族ジイソシアネートのイソシアヌレート誘導体、および/または、脂肪族ジイソシアネートのアルコール変性イソシアヌレート誘導体を含み、
前記ポリオール(B)は、エチレンオキサイドの含有量が30質量%以下であるポリオキシアルキレン(炭素数2〜3)ポリオール、および/または、ポリテトラメチレンエーテルグリコールを含み、
前記ポリオール(B)の平均水酸基価が30mgKOH/g以上70mgKOH/g以下であり、
前記可塑剤(C)の割合が、前記ポリオール成分(B)100質量部に対して、50質量部以上400質量部以下である
ことを特徴とする、ポリウレタンゲル材料。 - 前記ポリオール(B)の平均官能基数が、2.0である
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 前記ポリオール(B)の平均水酸基価が37mgKOH/g以上56mgKOH/g以下である
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 前記脂肪族ポリイソシアネート(A)の平均官能基数が2.3以上3.0以下である
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 前記脂肪族ジイソシアネートが、ペンタメチレンジイソシアネートおよび/またはヘキサメチレンジイソシアネートを含む
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 前記可塑剤(C)の割合が、前記ポリオール成分(B)100質量部に対して、100質量部以上200質量部以下である
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 前記可塑剤(C)が、シクロヘキサンジカルボン酸エステル類および/またはアジピン酸エステル類である
ことを特徴とする、請求項1に記載のポリウレタンゲル材料。 - 請求項1に記載のポリウレタンゲル材料の反応生成物である
ことを特徴とする、ポリウレタンゲル。 - 前記ポリウレタンゲル材料において、
ポリオール(B)中の水酸基に対する脂肪族ポリイソシアネート(A)中のイソシアネート基の当量比(NCO/水酸基)が、0.8以上1.2以下である
ことを特徴とする、請求項8に記載のポリウレタンゲル。 - 請求項8に記載のポリウレタンゲルからなることを特徴とする、疑似生体材料。
- 請求項1に記載のポリウレタンゲル材料を準備する準備工程と、
前記ポリウレタンゲル材料を反応および硬化させ、ポリウレタンゲルを得る反応工程とを備え、
前記反応工程において、
ポリオール(B)中の水酸基に対する脂肪族ポリイソシアネート(A)中のイソシアネート基の当量比(NCO/水酸基)が、0.8以上1.2以下である
ことを特徴とする、ポリウレタンゲルの製造方法。
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