JP7458574B2 - 硬化性樹脂組成物、硬化物及び立体造形物 - Google Patents
硬化性樹脂組成物、硬化物及び立体造形物 Download PDFInfo
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- JP7458574B2 JP7458574B2 JP2021565522A JP2021565522A JP7458574B2 JP 7458574 B2 JP7458574 B2 JP 7458574B2 JP 2021565522 A JP2021565522 A JP 2021565522A JP 2021565522 A JP2021565522 A JP 2021565522A JP 7458574 B2 JP7458574 B2 JP 7458574B2
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- 239000011342 resin composition Substances 0.000 title claims description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 105
- -1 acrylate compound Chemical class 0.000 claims description 62
- 229920005906 polyester polyol Polymers 0.000 claims description 31
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 25
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
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- 230000009477 glass transition Effects 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- 238000012360 testing method Methods 0.000 description 9
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
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- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
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- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
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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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/112—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using individual droplets, e.g. from jetting heads
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- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
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- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
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- C08F2/00—Processes of polymerisation
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
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- 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
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
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- 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
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
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- 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
- C08G18/67—Unsaturated compounds having active hydrogen
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
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- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y80/00—Products made by additive manufacturing
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Description
カラム ; 東ソー株式会社製ガードカラムHXL-H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC-8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
攪拌機、コンデンサー、温度計が備えられた反応容器に3-メチル-1,5-ペンタンジオール448質量部、アジピン酸352質量部を投入した。窒素気流下で撹拌しながら200~250℃で18時間反応させて、ポリエステルポリオール(1)を得た。このポリエステルポリオール(1)は、数平均分子量(Mn)が500であり、重量平均分子量が(Mw)1,100であり、酸価が2.4mgKOH/gであり、水酸基価が220mgKOH/gであった。なお、水酸基価及び酸価は、JIS K 0070(1992)の中和滴定法に基づいて測定される値である。
攪拌機、コンデンサー、温度計が備えられた反応容器に3-メチル-1,5-ペンタンジオール378質量部、アジピン酸422質量部を投入した。窒素気流下で撹拌しながら200~250℃で18時間反応させて、ポリエステルポリオール(2)を得た。このポリエステルポリオール(2)は、数平均分子量(Mn)が2,100であり、重量平均分子量(Mw)が3,800であり、酸価が3.0mgKOH/gであり、水酸基価が56mgKOH/gであった。
攪拌機、コンデンサー、温度計が備えられた反応容器に3-メチル-1,5-ペンタンジオール359質量部、アジピン酸441質量部を投入した。窒素気流下で撹拌しながら200~250℃で18時間反応させて、ポリエステルポリオール(3)を得た。このポリエステルポリオール(3)は、数平均分子量(Mn)が9,800であり、重量平均分子量(Mw)が19,400であり、酸価が3.2mgKOH/gであり、水酸基価が9mgKOH/gであった。
攪拌機、コンデンサー、温度計が備えられた反応容器にネオペンチルグリコール353質量部、アジピン酸450質量部を投入した。窒素気流下で撹拌しながら200~250℃で18時間反応させて、ポリエステルポリオール(4)を得た。このポリエステルポリオール(4)は、数平均分子量(Mn)が2,000であり、重量平均分子量が(Mw)4,200であり、酸価が3.0mgKOH/gであり、水酸基価が53mgKOH/gであった。
攪拌機、コンデンサー、温度計が備えられた反応容器にエチレングリコール262質量部、アジピン酸571質量部を投入した。窒素気流下で撹拌しながら200~250℃で18時間反応させて、ポリエステルポリオール(5)を得た。このポリエステルポリオール(5)は、数平均分子量(Mn)が2,300であり、重量平均分子量(Mw)が4,800であり、酸価が2.0mgKOH/gであり、水酸基価が49mgKOH/gであった。
攪拌機、ガス導入管、コンデンサー、及び温度計を備えた1リットルのフラスコに、イソホロンジイソシアネート297質量部、ターシャリブチルヒドロキシトルエン1.6質量部、メトキシハイドロキノン0.2質量部、ジブチル錫ジアセテート0.2質量部を加え、70℃に昇温し、合成例1で得たポリエステルポリオール(1)347質量部を1時間にわたって滴下した。滴下後、70℃で3時間反応させた後、ヒドロキシエチルアクリレート155質量部を1時間にわたって滴下した。滴下後、イソシアネート基を示す2250cm-1の赤外吸収スペクトルが消失するまで70℃で反応を行い、アクリロイル基を有するウレタン樹脂(A-1)を得た。
攪拌機、ガス導入管、コンデンサー、及び温度計を備えた1リットルのフラスコに、イソホロンジイソシアネート131質量部、ターシャリブチルヒドロキシトルエン1.6質量部、メトキシハイドロキノン0.2質量部、ジブチル錫ジアセテート0.2質量部を加え、70℃に昇温し、合成例2で得たポリエステルポリオール(2)600質量部を1時間にわたって滴下した。滴下後、70℃で3時間反応させた後、ヒドロキシエチルアクリレート68質量部を1時間にわたって滴下した。滴下後、イソシアネート基を示す2250cm-1の赤外吸収スペクトルが消失するまで70℃で反応を行い、アクリロイル基を有するウレタン樹脂(A-2)を得た。
攪拌機、ガス導入管、コンデンサー、及び温度計を備えた1リットルのフラスコに、イソホロンジイソシアネート27質量部、ターシャリブチルヒドロキシトルエン1.6質量部、メトキシハイドロキノン0.2質量部、ジブチル錫ジアセテート0.2質量部を加え、70℃に昇温し、合成例3で得たポリエステルポリオール(3)760質量部を1時間にわたって滴下した。滴下後、70℃で3時間反応させた後、ヒドロキシエチルアクリレート14質量部を1時間にわたって滴下した。滴下後、イソシアネート基を示す2250cm-1の赤外吸収スペクトルが消失するまで70℃で反応を行い、アクリロイル基を有するウレタン樹脂(A-3)を得た。
攪拌機、ガス導入管、コンデンサー、及び温度計を備えた1リットルのフラスコに、イソホロンジイソシアネート125質量部、ターシャリブチルヒドロキシトルエン1.6質量部、メトキシハイドロキノン0.2質量部、ジブチル錫ジアセテート0.2質量部を加え、70℃に昇温し、合成例4で得たポリエステルポリオール(4)609質量部を1時間にわたって滴下した。滴下後、70℃で3時間反応させた後、ヒドロキシエチルアクリレート65質量部を1時間にわたって滴下した。滴下後、イソシアネート基を示す2250cm-1の赤外吸収スペクトルが消失するまで70℃で反応を行い、アクリロイル基を有するウレタン樹脂(A-4)を得た。
攪拌機、ガス導入管、コンデンサー、及び温度計を備えた1リットルのフラスコに、イソホロンジイソシアネート118質量部、ターシャリブチルヒドロキシトルエン1.6質量部、メトキシハイドロキノン0.2質量部、ジブチル錫ジアセテート0.2質量部を加え、70℃に昇温し、合成例5で得たポリエステルポリオール(5)620質量部を1時間にわたって滴下した。滴下後、70℃で3時間反応させた後、ヒドロキシエチルアクリレート62質量部を1時間にわたって滴下した。滴下後、イソシアネート基を示す2250cm-1の赤外吸収スペクトルが消失するまで70℃で反応を行い、アクリロイル基を有するウレタン樹脂(A-5)を得た。
攪拌機、温度計及び冷却管を備えた4つ口のフラスコに、合成例6で得たアクリロイル基を有するウレタン樹脂(A-1)30質量部、アクリロイルモルホリン(KJケミカルズ社製「ACMO」)70質量部を仕込んだ後、60℃以下で、均一溶解するまで攪拌し、硬化性樹脂組成物(1)を得た。
アクリロイル基を有するウレタン樹脂、及び(メタ)アクリレート化合物を表1に示した組成及び配合量に変更した以外は、実施例1と同様の方法にて硬化性樹脂組成物(2)~(9)を得た。
実施例1で用いたアクリロイル基を有するポリウレタン樹脂、及び(メタ)アクリレート化合物を表1に示した組成及び配合量に変更した以外は、実施例1と同様の方法にて硬化性樹脂組成物(C1)~(C3)を得た。
E型粘度計(東機産業株式会社製「TV-22」)を用いて、各実施例及び比較例で得られた硬化性樹脂組成物の25℃における粘度を測定した。
光造形3Dプリンター(株式会社ディーメック社製「ACCULAS BA-30S」)を用いて、引っ張り試験用ダンベル(ASTM D638 TYPE1準拠)、及びアイゾット衝撃試験用テストピース(ASTM D256準拠)を作製した。次いで、光造形により得られた前記引っ張り試験用ダンベル、及び前記アイゾット衝撃試験用テストピースをイソプロピルアルコールで洗浄し、常温で1時間乾燥後、後硬化として高圧水銀ランプにて、両面をそれぞれUV照射(各10000mJ/cm2)して、試験片1(引っ張り試験用ダンベル)及び試験片2(アイゾット衝撃試験用テストピース)を得た。
ASTM D638に準拠し、前記試験片1を用いて、島津製作所製オートグラフ「AG-Xplus 100kN」(ロードセル100kN、ヘッドスピード5mm/min、試験片幅10mm)により、引っ張り試験を行い、弾性率及び伸度を測定した。
ASTM D256に準拠し、前記試験片2を用いて、株式会社東洋精機製作所製「ユニバーサルインパクトテスター」により、アイゾット衝撃強度を測定した。
Claims (5)
- (メタ)アクリロイル基を有するウレタン樹脂(A)と、単官能(メタ)アクリレート化合物(B1)とを含有する硬化性樹脂組成物であって、
前記ウレタン樹脂(A)が、ポリエステルポリオール(a1)と、ポリイソシアネート(a2)と、水酸基及び(メタ)アクリロイル基を有する化合物(a3)とを必須の反応原料とするものであり、
前記ポリエステルポリオール(a1)が、側鎖に炭化水素基を有するグリコール(a1-1)と、ポリカルボン酸(a1-2)とを必須の反応原料とするものであり、
前記グリコール(a1-1)が、3-メチルペンタンジオールであり、
前記単官能(メタ)アクリレート化合物(B1)が、ジシクロペンテニル(メタ)アクリレート及びジシクロペンタニル(メタ)アクリレートからなる群より選ばれる1種以上であり、
前記ポリエステルポリオール(a1)の数平均分子量(Mn)が、1,500~8,000の範囲であることを特徴とする硬化性樹脂組成物。 - 前記ウレタン樹脂(A)の含有率が、前記硬化性樹脂組成物の固形分中に3~50質量%の範囲である請求項1記載の硬化性樹脂組成物。
- 前記単官能(メタ)アクリレート化合物(B1)の重合体のガラス転移温度が、80℃以上である請求項1記載の硬化性樹脂組成物。
- 請求項1~3のいずれか1項記載の硬化性樹脂組成物の硬化反応物であることを特徴とする硬化物。
- 請求項4記載の硬化物からなることを特徴とする立体造形物。
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