JP6406002B2 - 光学的立体造形活性エネルギー線重合性樹脂組成物、及び立体造形物 - Google Patents
光学的立体造形活性エネルギー線重合性樹脂組成物、及び立体造形物 Download PDFInfo
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- JP6406002B2 JP6406002B2 JP2014264321A JP2014264321A JP6406002B2 JP 6406002 B2 JP6406002 B2 JP 6406002B2 JP 2014264321 A JP2014264321 A JP 2014264321A JP 2014264321 A JP2014264321 A JP 2014264321A JP 6406002 B2 JP6406002 B2 JP 6406002B2
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- meth
- vinyl
- acid
- acrylic acid
- acrylate
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- 238000004088 simulation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940006186 sodium polystyrene sulfonate Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- XMRZNNGTCUALQE-UHFFFAOYSA-N tert-butyl 3-(4-ethenylphenoxy)propanoate Chemical compound CC(C)(C)OC(=O)CCOC1=CC=C(C=C)C=C1 XMRZNNGTCUALQE-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YQPZJBVEKZISEF-UHFFFAOYSA-N tetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YQPZJBVEKZISEF-UHFFFAOYSA-N 0.000 description 1
- NPWJBNPQTPEEGC-UHFFFAOYSA-N tetradecyl 4-ethenylbenzoate Chemical compound C(CCCCCCCCCCCCC)OC(C1=CC=C(C=C1)C=C)=O NPWJBNPQTPEEGC-UHFFFAOYSA-N 0.000 description 1
- FKGZHILWPVEUNC-UHFFFAOYSA-N tetrakis(dimethylsilyl)silane Chemical compound C[SiH](C)[Si]([SiH](C)C)([SiH](C)C)[SiH](C)C FKGZHILWPVEUNC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- KXEMQEGRZWUKJS-QIYNHLNTSA-N tetraphylline Chemical class COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-QIYNHLNTSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
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- 239000001017 thiazole dye Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
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- 150000004992 toluidines Chemical class 0.000 description 1
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- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
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- 239000005052 trichlorosilane Substances 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- NELVVTIEGZVCKM-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CCCNC(=O)C=C.C[N+](C)(C)CCCNC(=O)C=C NELVVTIEGZVCKM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- QTKHQYWRGFZFHG-UHFFFAOYSA-N trioctylsilicon Chemical compound CCCCCCCC[Si](CCCCCCCC)CCCCCCCC QTKHQYWRGFZFHG-UHFFFAOYSA-N 0.000 description 1
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- XJXSSNSCWGKDOW-UHFFFAOYSA-N tripentoxysilane Chemical compound CCCCCO[SiH](OCCCCC)OCCCCC XJXSSNSCWGKDOW-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
- GSDMVIWNWCWYFB-UHFFFAOYSA-N tris(2-chloroethoxy)silane Chemical compound ClCCO[SiH](OCCCl)OCCCl GSDMVIWNWCWYFB-UHFFFAOYSA-N 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- GEUFMGZEFYJAEJ-UHFFFAOYSA-N tris(2-methylpropyl)silicon Chemical compound CC(C)C[Si](CC(C)C)CC(C)C GEUFMGZEFYJAEJ-UHFFFAOYSA-N 0.000 description 1
- KYJXEJLEWKXHOC-UHFFFAOYSA-N tris(3-methoxypropoxy)-methylsilane Chemical compound COCCCO[Si](C)(OCCCOC)OCCCOC KYJXEJLEWKXHOC-UHFFFAOYSA-N 0.000 description 1
- GIRKRMUMWJFNRI-UHFFFAOYSA-N tris(dimethylamino)silicon Chemical compound CN(C)[Si](N(C)C)N(C)C GIRKRMUMWJFNRI-UHFFFAOYSA-N 0.000 description 1
- SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- CIBGZAYGXFGOFK-UHFFFAOYSA-L zinc;2-phenylethenesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C=CC1=CC=CC=C1.[O-]S(=O)(=O)C=CC1=CC=CC=C1 CIBGZAYGXFGOFK-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
これらは、活性エネルギー線で重合し得る樹脂とα,β−不飽和二重結合基を有する単量体のみを含有し、単量体が溶媒の機能をかねていることから塗膜や成型品形成時に溶剤が揮発しないという利点があるからである。そして、この活性エネルギー線重合性を有する樹脂として、低分子量のポリエステル系樹脂、ポリウレタン系樹脂、ポリエポキシ系樹脂、ポリアクリル系樹脂等の分子末端にα,β−不飽和二重結合基を有するオリゴマーやα,β−不飽和二重結合基を有する単量体等が利用されている。
この光造形法は、従来の切削加工などと比べて、切削困難な複雑な形状にも対応可能、完全自動化プロセスであり取り扱いが容易、製造時間が短くコスト面でも有利などの様々な利点を有しており、樹脂製品の生産の他、デザイン検討、性能試験、広告用等の試作モデルや医療モデルなどの製造に幅広く用いられるようになってきている。
この立体造形法の代表的な例としては、容器に入れた液状の光硬化性樹脂組成物の液面に、所望パターンの重合硬化層が得られるように、光、例えば、活性エネルギー線の一種である紫外線レーザー光を選択的に照射して重合硬化層を得、次に該硬化層の上に液状の光硬化性樹脂組成物を層状に供給し、次いで前記と同様に光を選択的に照射して前記の硬化層と連続した重合硬化層を形成する。この積層操作を繰り返すことにより、最終的に所望の立体造形物を得る方法である。この立体造形法は、製作する造形物の形状が複雑な場合でも、容易にしかも短時間で目的の造形物を得ることができるため注目されている。
さらに、特許文献7には、エチレン系不飽和モノマーや光開始剤との屈折率の差の絶対値が0でない微小中空球を含有する光硬化性液体組成物が開示されており、該光硬化性液体組成物の透明度が減少することが記載されている。さらに、特許文献8には、発色剤を含有する照射硬化性樹脂組成物が開示されており、該照射硬化性樹脂組成物から製造された三次元物品は、硬化の前後で異なる色を示すことが記載されている。
しかしながら、上記樹脂組成物を硬化して得られる樹脂硬化物も、強靱性、耐水性、物性安定性や経時的変形の抑制の全ての要求を満足するには至っていないのが現状である。
すなわち、本発明は、水と、
分子内に1個以上の水酸基を有するα,β−不飽和二重結合基含有化合物(A)と、
分子内に水酸基を有しないα,β−不飽和二重結合基含有化合物(B)と、開始剤(E)と
を含有する光学的立体造形用活性エネルギー線重合性樹脂組成物であり、
化合物(A)が、水酸基を有する脂肪酸エステル系(メタ)アクリル酸エステル、および水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類からなる群より選ばれる一つ以上の化合物であり、
化合物(B)が、(メタ)アクリル酸環状エステル類、2官能(メタ)アクリル酸環状エステル類、ヘテロ環状アクリルアミド類、酸素原子を有するヘテロ環含有(メタ)アクリル酸エステル類および2官能(メタ)アクリル酸エステル類からなる群より選ばれる一つ以上の化合物であり、
開始剤(E)が、光ラジカル発生剤である光学的立体造形用活性エネルギー線重合性樹脂組成物に関する。
ただし、活性エネルギー線重合性組成物(ただし、水を除く)100重量部に対し、水を0.01〜10重量部含有する。
ただし、活性エネルギー線重合性組成物(ただし、水を除く)100重量部に対し、水を0.01〜10重量部、化合物(A)を0.5〜40重量部、および化合物(B)を20〜99重量部含有する。
活性エネルギー線で重合硬化してなる樹脂硬化物に関する。
<光学的立体造形用活性エネルギー線重合性樹脂組成物の構成>
本発明の光学的立体造形用樹脂組成物は、水と、
分子内に1個以上の水酸基を有するα,β−不飽和二重結合基含有化合物(A)と、
分子内に水酸基を有しないα,β−不飽和二重結合基含有化合物(B)と、
を含有する光学的立体造形用活性エネルギー線重合性樹脂組成物に関するものである。
ただし、活性エネルギー線重合性組成物(ただし、水を除く)100重量部に対し、水を0.01〜10重量部含有する。
<化合物(A)>
本発明の樹脂組成物において、分子内に1個以上の水酸基を有するα,β−不飽和二重結合基含有化合物(A)について説明する。
化合物(a1)としては、基材との密着性の面より、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸4−ヒドロキシブチル、ε−カプロラクトン1〜2mol付加(メタ)アクリル酸2−ヒドロキシエチル等の炭素数2〜18であるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
本発明の樹脂組成物において、分子内に水酸基を有しないα,β−不飽和二重結合基含有化合物(B)について説明する。本発明において、上記化合物(B)は、分子内に水酸基を有しないα,β−不飽和二重結合基を含有する化合物の単量体であり、上記樹脂組成物に上記成分(B)を含有することによって、前記化合物(A)との共重合反応の効率化及び高感度化を図ることが容易である。また、上記樹脂組成物を容易に低粘度化できるとともに、造形時の作業性を向上させることが容易となる。また、造形物のガラス転移点(Tg)を向上させて高凝集力を発現させたり、耐熱性や耐水性等の耐性の良好な立体造形物を形成することが可能となるものである。特に限定するものではないが、成分(B)として使用可能な化合物としては、以下が挙げられる。
4−ビニル安息香酸メチルポリ(エチレンオキサイド)、4−ビニル安息香酸エチルポリ(エチレンオキサイド)、4−イソプロペニル安息香酸メチルポリ(プロピレンオキサイド)、4−イソプロペニル安息香酸エチルポリ(プロピレンオキサイド)などのポリアルキレンオキサイド部位を有するビニル安息香酸エステル系またはイソプロペニル安息香酸エステル系単量体類;
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
本発明の化合物(B)は、前述の分子内に水酸基を有するα,β−不飽和二重結合基含有化合物(A)との共重合反応性と共重合反応後における硬化物の凝集力向上の点をを考慮すると、化合物(B)に含有されるα,β−不飽和二重結合基が、アクリロイル基、またはメタクリロイル基であることが好ましい。さらに、後述の立体造形物の硬化収縮を低減したり、可撓性の向上を可能にすることができる。
樹脂組成物全量中、水と、化合物(A)とが、それぞれ0.01重量%、0.5重量%以上であれば、十分な凝集力が得られ易く耐熱性や耐湿熱性の向上効果が期待できる。一方、樹脂組成物全量中、水と、化合物(A)とが、それぞれ10重量%、40重量%以下であれば、樹脂組成物を光造形材料として用いた場合に、立体造形物の硬化収縮が低減でき、可撓性が向上するので好ましい。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、カチオン重合性化合物(C)を含んでもよい。カチオン重合性化合物(C)を使用することによって、樹脂組成物を立体造形物として使用した時に、活性エネルギー線照射による異種重合硬化が可能なるため、硬化物が相分離構造を形成し、弾性と応力緩和性やクリープ特性を制御しやすいため、適度な弾性や可撓性維持と硬化収縮抑制をより向上させることができる。また樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
工業的には、プロピオラクトン、ブチロラクトン、バレロラクトン、カプロラクトン、1,3−ジオキソラン、1,2−ジオキサン、1,3−ジオキサン、1,4−ジオキサン、1,3,5−トリオキサン、エチレンカーボネート、プロピレンカーボネート、グリセリンカーボネート等が反応性の点で好ましく用いられる。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、オリゴマー(D)を含んでもよい。オリゴマー(D)を使用することによって、樹脂組成物を光造形材料として使用した時に、造形性及び硬化収縮性をより向上させることができる。また樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
ポリエステル系オリゴマー(d1)としては、主鎖骨格に多塩基酸と多価アルコールを重縮合して得られるポリエステルの末端あるいはポリエステル鎖中の水酸基と(メタ)アクリル酸、マレイン酸などの分子内に1個以上のカルボキシル基を有するα,β−エチレン性不飽和二重結合基含有化合物とのエステル化によって得られる化合物、あるいはポリエステルの末端あるいはポリエステル鎖中のカルボキシル基と(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピルなどの前述の化合物(A)とのエステル化によって得られる化合物である。その他、酸無水物と(メタ)アクリル酸グリシジルと少なくとも1個の水酸基を有する化合物とから得られるポリエステルオリゴマー等もポリエステルオリゴマー(d1)として使用可能である。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
ポリウレタン系オリゴマー(d2)は、少なくとも1個以上のイソシアネート基を有する化合物と前記化合物(A)を反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と上述の多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(A)を反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、更に少なくとも1個以上のアミノ基を有する化合物とを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(A)とを反応させて得られる化合物である。また、イソシアネート基とアミノ基とを反応させて得られるウレア結合基を含有したものもポリウレタン系オリゴマー(d2)に含む。
また、アミノ基を有するアミン類としては、、例えばアミノメタン、アミノエタン、1−アミノプロパン、2−アミノプロパン、1−アミノブタン、2−アミノブタン、1−アミノペンタン、2−アミノペンタン、3−アミノペンタン、イソアミルアミン、1−アミノヘキサン、1−アミノヘプタン、2−アミノヘプタン、2−オクチルアミン、1−アミノノナン、1−アミノデカン、1−アミノドデカン(ラウリルアミン)、1−アミノトリデカン、1−アミノヘキサデカン、1−アミノテトラデデカン(ミリスチルアミン)、1−アミノペンタデカン、セチルアミン、オレイルアミン、ココアルキルアミン、牛脂アルキルアミン、硬化牛脂アルキルアミン、アリルアミン、ステアリルアミン、アミノシクロプロパン、アミノシクロブタン、アミノシクロペンタン、アミノシクロヘキサン、アミノシクロドデカン、1−アミノ−2−エチルヘキサン、1−アミノ−2−メチルプロパン、2−アミノ−2−メチルプロパン、3−アミノ−1−プロペン、3−アミノメチルヘプタン、3−イソプロポキシプロピルアミン、3−ブトキシプロピルアミン、3−イソブトキシプロピルアミン、2−エチルヘキシロキシプロピルアミン、3−デシロキシプロピルアミン、3−ラウリロキシプロピルアミン、3−ミリスチロキシプロピルアミン、2−アミノメチルテトラヒドロフラン、アニリン、o−アミノトルエン、m−アミノトルエン、p−アミノトルエン、o−ベンジルアニリン、p−ベンジルアニリン、1−アニリノナフタレン、1−アミノアントラキノン、2−アミノアントラキノン、1−アミノアントラセン、2−アミノアントラセン、5−アミノイソキノリン、o−アミノジフェニル、4−アミノジフェニルエーテル、2−アミノベンゾフェノン、4−アミノベンゾフェノン、o−アミノアセトフェノン、m−アミノアセトフェノン、p−アミノアセトフェノン、ベンジルアミン、α−フェニルエチルアミン、フェネシルアミン、p−メトキシフェネシルアミン、p−アミノアゾベンゼン、m−アミノフェノール、p−アミノフェノール、アリルアミン等の1級アミン類;
ポリエポキシ系オリゴマー(d3)は、グリシジル基を有する化合物とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有するα,β−不飽和二重結合基含有化合物との反応により得られる化合物であり、実質的にグリシジル基を有さず、かつα,β−不飽和二重結合基含有化合物を有する化合物である。代表例としてビスフェノール型、エポキシ化油型、フェノールノボラック型、脂環型が挙げられる。ビスフェノール型ポリエポキシ系オリゴマーとしては、ビスフェノール類とエピクロルヒドリンとを反応させて得られるビスフェノール型ジグリシジルエーテルと(メタ)アクリル酸などの分子内に1個以上のカルボキシル基を有するα,β−不飽和二重結合基含有化合物とを反応して得られるものである。
本発明では、オリゴマー(D)として、アクリル系オリゴマー(d4)を使用することもできる。使用可能な化合物の具体例として、α,β−不飽和二重結合基を有する変性ポリエーテル、アミン変性されたα,β−不飽和二重結合基含有化合物、並びに、アルキッド樹脂、スピロアセタール樹脂、ポリブタジエン樹脂、ポリチオールポリエン樹脂及び多価アルコール等の各種化合物にα,β−不飽和二重結合基を付加させた変性α,β−不飽和二重結合基含有化合物、からなる群より選択される1以上の化合物の、オリゴマーまたはプレポリマーを使用することができる。
なお、数平均分子量(Mn)、重量平均分子量(Mw)、酸価(AV)及び水酸基価(OHV)の測定方法については後述する。
本発明の樹脂組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。しかし、上記樹脂組成物は、必要に応じて、活性エネルギー線重合開始剤(E)を含んでもよい。活性エネルギー線重合開始剤(E)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましく、紫外線の照射によって重合反応を進行させる場合、樹脂組成物は、活性エネルギー線重合開始剤(E)を含むことが好ましい。
具体例として、例えば、以下が挙げられる。2,2−ジメトキシ−2−フェニルアセトフェノン、アセトフェノン、ベンゾフェノン、キサントフルオレノン、ベンズアルデヒド、アントラキノン、3−メチルアセトフェノン、4−クロロベンゾフェノン、4,4’−ジアミノベンゾフェノン、ベンゾインプロピルエーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4−チオキサントン、カンファーキノン、及び2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン等の光ラジカル発生剤(e1)。
上記、増感剤の中でチオキサントン誘導体としては、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジクロロチオキサントン、2−イソプロピルチオキサントン、4−イソプロピルチオキサントン、1−クロロ−4−プロポキシチオキサントン等を挙げることができ、ベンゾフェノン類としては、ベンゾフェノン、4−メチルベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4,4'−ジメチルベンゾフェノン、4,4'−ジメトキシベンゾフェノン、4,4'−ビス(ジエチルアミノ)ベンゾフェノン等を挙げることができ、クマリン類としては、クマリン1、クマリン338、クマリン102等を挙げることができ、ケトクマリン類としては、3,3'−カルボニルビス(7−ジエチルアミノクマリン)等を挙げることができるが、これらに限定されるものではない。
次に、シラン化合物(F)について、説明する。
本発明の樹脂組成物には、シラン化合物(F)を含有することが好ましい。シラン化合物(F)としては、公知のシラン化合物を用いることができ、後述の立体造形物の強度が向上するものであれば特に限定されない。例えば、アルキル系アルコキシシラン、アリール系アルコキシシラン、ビニル系アルコキシシラン、アミノ系アルコキシシラン、エポキシ系アルコキシシラン、ハロゲン系アルコキシシラン、(メタ)アクリロイル系アルコキシシラン、メルカプト系アルコキシシラン、カチオン系アルコキシシラン、イソシアネート系アルコキシシラン等のアルコキシル基を有するアルコキシシラン類、及び/または、珪素原子に水素原子が直接結合して反応性を有する有機シラン類等が挙げられる。より具体的に、例えば、テトラメトキシシラン、テトラエトキシシラン、テトライソプロポキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリイソプロポキシシラン、メチルトリアセトキシシラン、メチルトリス( メトキシエトキシ) シラン、メチルトリス( メトキシプロポキシ)シラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリイソプロポキシシラン、プロピルトリメトキシシラン、プロピルトリエトキシシラン、プロピルトリイソプロポキシシラン、ブチルトリメトキシシラン、ブチルトリエトキシシラン、ヘキシルトリメトキシシラン、ヘキシルトリエトキシシラン、オクチルトリメトキシシラン、オクチルトリエトキシシラン、デシルトリメトキシシラン、デシルトリエトキシシラン、シクロヘキシルトリメトキシシラン、シクロヘキシルトリエトキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジイソプロポキシシラン、ジメチルジアセトキシシラン、ジメチルビス(メトキシエトキシ)シラン、ジメチルビス(メトキシプロポキシ)シラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチルジイソプロポキシシラン、ジエチルジアセトキシシラン、メチルエチルジメトキシシラン、メチルエチルジエトキシシラン、メチルエチルジイソプロポキシシラン、メチルエチルジアセトキシシラン、メチルプロピルジメトキシシラン、メチルプロピルジエトキシシラン、メチルプロピルジイソプロポキシシラン、メチルプロピルジアセトキシシラン、等のアルキル系アルコキシシラン類;
次に、酸化防止剤(G)について、説明する。
本発明における樹脂組成物は、更に酸化防止剤を含んでも良い。酸化防止剤(G)を含むことによって、活性エネルギー線重合後の樹脂硬化物の経時での着色を抑制することができる。
酸化防止剤としては、例えば、アデカスタブAO‐50、アデカスタブAO‐80(アデカ社製)などのフェノール系酸化防止剤や、アデカスタブPEP−8(アデカ社製)、IRGAFOS168(BASF社製)などのリン系酸化防止剤、IRGANOX‐PS‐800FD(BASF社製)などのイオウ系酸化防止剤、TINUBIN622LD、TINUBIN144、TINUBIN765(3種ともBASF社製)等のヒンダードアミン系の光安定剤等の市販品が挙げられるが、これらに限定されるものではない。
酸化防止剤(G)の配合割合は、光学的立体造形用樹脂組成物100重量部(ただし、水分を除く)に対して、0.01〜20重量部であり、0.01〜10重量部であることが好ましい。0.01重量部より少ないと、活性エネルギー線により早期に消費されてしまうため、重合率が下がり、逆に20重量部より多くなると、重合率は上がるが、樹脂硬化物の分子量が低下し、立体造形物としての凝集力が低下するため、耐久性が低下する。
本発明の樹脂組成物は、上記成分に加えて、色材(H)を含有しても良い。色材(H) を使用することによって、立体造形物として使用して使用した場合、含有される染料や顔料によって、意匠性だけで無く、熱特性、電気特性、あるいは光学特性等の様々な機能性を付与することが可能となる。
例えば、有機顔料としては、トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー、ピラゾロンレッドなどの不溶性アゾ顔料、
リトールレッド、ヘリオボルドー、ピグメントスカーレット、パーマネントレッド2Bなどの溶性アゾ顔料、
アリザリン、インダントロン、チオインジゴマルーンなどの建染染料からの誘導体、
フタロシアニンブルー、フタロシアニングリーンなどのフタロシアニン系有機顔料、
キナクリドンレッド、キナクリドンマゼンタなどのキナクリドン系有機顔料、
ペリレンレッド、ペリレンスカーレットなどのペリレン系有機顔料、
イソインドリノンエロー、イソインドリノンオレンジなどのイソインドリノン系有機顔料、
ピランスロンレッド、ピランスロンオレンジなどのピランスロン系有機顔料、チオインジゴ系有機顔料、縮合アゾ系有機顔料、ベンズイミダゾロン系有機顔料、
キノフタロンエローなどのキノフタロン系有機顔料、
イソインドリンエローなどのイソインドリン系有機顔料、
その他の顔料として、フラバンスロンエロー、アシルアミドエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド、ジオキサジンバイオレット等の有機顔料類が挙げられる。
これら色素誘導体であれば、特に問題無く使用できる。
分散樹脂は、染料や顔料(h1)100重量部に対し、不揮発分換算で10〜60重量部の範囲で使用する事が好ましい。また、化合物(A)、化合物(B)、化合物(C)、あるいはオリゴマー(D)を併用使用する場合には、染料や顔料(h1)100重量部に対し、不揮発分換算で100〜800重量部の範囲で使用する事が好ましい。
分散樹脂や化合物(A)、化合物(B)、化合物(C)、あるいはオリゴマー(D)が、この範囲より少ないと分散安定性が低下して、樹脂組成物の分散安定性、保存安定性が悪化する場合がある。一方、この範囲を超えると樹脂組成物の粘度が著しく上昇し、樹脂組成物の保存安定性に悪影響を及ぼす場合があったり、樹脂硬化物の造形不良が発生したり、立体造形物表面へのマイグレーションが発生したりするため、立体造形物の造形性や強度についても低下する場合がある。
このような極性樹脂としては、例えば、ポリビニルアルコール、ポリビニルピロリドン、ポリエチレングリコール、ポリ(メタ)アクリル酸、(メタ)アクリル酸−(メタ)アクリル酸アルキルエステル共重合体、スチレン−マレイン酸共重合体、スチレン−マレイン酸−(メタ)アクリル酸アルキルエステル共重合体、酢酸ビニル−クロトン酸共重合体、酢酸ビニル−(メタ)アクリル酸共重合体、ポリスチレンスルホン酸、ポリスチレンスルホン酸ナトリウム、スチレンスルホン酸−マレイン酸共重合体、ポリイタコン酸、等の親水性のビニル系共重合体;
メチルセルロース、エチルセルロース、プロピルセルロース、エチルメチルセルロース、ヒドロキシアルキルセルロース、ヒドロキシプロピルメチルセルロース、カルボシキメチルスセルロース、アルカリ金属カルボキシメチルセルロース、アルカリ金属セルロース硫酸塩、セルロースグラフト重合体等のセルロース誘導体;
ポリグルタミン酸、ポリアスパラギン酸等のポリペプチド類;
長鎖ポリアミノアマイドと極性酸エステルの塩、長鎖ポリアミノアマイドと高分子量酸エステルの塩、ナフタレンスルホン酸ホルマリン縮合物塩、ステアリルアミンアセテート等のアミドエステル塩;
等が挙げられるが、特にこれらに限定されるものではない。これらは1種類または2種以上を併用して用いることができる。
また、Efka CHEMICALS社製「エフカ44、46、47、48、49、54、63、64、65、66、71、701、764、766」、「エフカポリマー100(変性ポリアクリレート)、150(脂肪族系変性ポリマー)、400、401、402、403、450、451、452、453(変性ポリアクリレート)、745(銅フタロシアニン系)」、共栄社化学社製「フローレン TG−710(ウレタンオリゴマー)、「フローノンSH−290、SP−1000」、「ポリフローNo.50E、No.300(アクリル系共重合物)」、楠本化成社製「ディスパロン KS−860、873SN、874(高分子分散剤)、#2150(脂肪族多価カルボン酸)、#7004(ポリエーテルエステル型)」が挙げられる。
本発明の樹脂組成物は、本発明の効果を損なわない範囲で有れば、前記したような成分の他に各種添加剤(Q)を適宜配合することが可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、着色向上等の観点から有機又は無機の充填剤を配合できる。このような充填剤としては、ポリマー、セラミックス、金属、金属酸化物、金属塩等を用いることができ、形状については粒子状、繊維状等特に限定されない。なお、上記ポリマーの配合に当っては、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、消泡剤等、充填剤としてではなくポリマーブレンド、ポリマーアロイとして、光学的立体造形用樹脂組成物中に溶解、半溶解又はミクロ分散させることも可能である。
次に、光学的立体造形用活性エネルギー線重合性樹脂組成物の性状について、説明する。
本発明の樹脂組成物は、上記、水、化合物(A)、化合物(B)を必須成分とし、更に、必要に応じて、化合物(C)、化合物(D)、光重合開始剤(E)、シラン化合物(F)、酸化防止剤(G)、色剤(H)およびその他の各種添加剤(Q)を配合後、均一に混合することによって製造することができる。
攪拌・混合する際には、減圧装置を備えた1軸または多軸エクストルーダー、ニーダー、ディソルバーのような汎用の機器を使用し攪拌・混合することにより調製してもよい。攪拌・混合する際の温度は、通常、10〜60℃に設定されるのが好ましい。調製時の設定温度が10℃未満では、粘度が高すぎて均一な撹拌・混合作業が困難になる場合があり、逆に、調製時の温度が60℃を超えると、熱による硬化反応が起きる場合があり、正常な脂組成物が得られない場合があるので、好ましくない。
なお、本発明における樹脂組成物は、実質的に有機溶剤を含まないことが好ましいが、機溶剤を含有することも可能である。 例えば、メタノール、エタノール、イソプロピルアルコール、アセトン、メチルエチルケトン、メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢酸ブチル、シクロヘキサン、トルエン、キシレンその他の炭化水素系溶媒等の有機溶媒や、水をさらに添加して、光学的立体造形用樹脂組成物の粘度を調整することもできるし、光学的立体造形用樹脂組成物を加熱して粘度を低下させることもできる。
樹脂組成物の粘度は、化合物(A)、及び化合物(B)の粘度で殆ど決定されるため、これらの粘度を1〜100,000mPa・sの範囲で管理することにより、樹脂組成物の粘度も管理が可能である。
次に、樹脂硬化物、光学的立体造形用活性エネルギー線重合性樹脂組成物の造形プロセス(光学的立体造形法)について、説明する。
本発明の樹脂組成物は、光学的立体造形法(以下、光造形法ともいう)における光硬化性液状樹脂材料として好適に使用される。すなわち、本発明の樹脂組成物に対して、紫外線等の活性エネルギー線を選択的に照射して重合硬化に必要なエネルギーを供給する光造形法により、所望の立体形状の樹脂硬化物を製造することができる。
活性エネルギー線の照射光源としては、150〜550nm波長域の光を主体としたもので、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、ケミカルランプ、ブラックライトランプ、マイクロウェーブ励起水銀灯、LEDランプ、キセノンランプ又はメタルハライドランプなどの他、半導体レーザー光線、電子線なども露光用活性エネルギー線として利用できる。コスト面や指向性、収束性の点で紫外線レーザー光線が好ましい。
活性エネルギー線の照射強度は、1〜500mW/cm2であることが好ましい。光照射強度が1mW/cm2未満であると、硬化に長時間を必要とし、500mW/cm2を超えると、ランプから輻射される熱により、未硬化の樹脂組成物に劣化が生じる可能性があるため、好ましくない。照射強度と照射時間の積として表される積算照射量は1〜5,000mJ/cm2とであることが好ましい。積算照射量が1mJ/cm2より少ないと、重合硬化に長時間を必要とし、5,000mJ/cm2より大きいと、照射時間が非常に長くなり、生産性が劣るため、好ましくない。
次に、立体造形物について、説明する。
本発明の樹脂組成物を用いて立体造形物を得る代表的な方法としては、液状である本発明の光学的立体造形用樹脂組成物に、所望のパターンを有する硬化層が得られるように光を選択的に照射して硬化層を形成し、次に該硬化層に隣接する未硬化の組成物層に同様にして光を照射して先に形成された硬化層と連続する新たな硬化層を形成し、この積層操作を繰り返すことにより、最終的に目的とする立体形状の造形物とする方法を挙げることができる。この方法のさらに具体的態様としては、次に例示する方法を挙げることができる。
[作製例1、2]
化合物(B)と分散樹脂とを攪拌し、分散樹脂が完全に溶解したことを確認した後、染料、または顔料(h1)を投入し、ハイスピードミキサー等で均一になるまで攪拌後、得られたミルベースを横型サンドミルで約2時間分散して作製した。作製した色材(H)(顔料分散体)の配合を表1に示す。
・染料、または顔料(h1)
E5B02:クラリアント社製 キナクリドン顔料 「Hostaperm Red E5B02」
E4GN:ランクセス社製 ニッケル錯体アゾ顔料 「YELLOW PIGMENT E4GN」
・分散樹脂
24000:アビシア社製 顔料分散剤「ソルスパーズ24000」
33000:アビシア社製 顔料分散剤「ソルスパーズ33000」
・化合物(B)
PhA:アクリル酸2−フェノキシエチル
本発明では、上述の成分に限定されることなく、各種特性に優れた色材の水性分散体を提供することができる。
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、水、化合物(A)、化合物(B)を必須成分として、さらに必要に応じて、カチオン重合性化合物(C)、オリゴマー(D)、活性エネルギー線重合開始剤(E)、シラン化合物(F)、酸化防止剤(G)、色材(H)および各種添加剤(Q)を表2に示す比率で仕込み、攪拌機にて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す樹脂組成物を得た。
各配合例で得られた樹脂組成物の液体外観を目視にて評価した。また、分子量、水酸基価、酸価、及びガラス転移温度の測定方法も記載した。
各配合例で得られた樹脂組成物を23℃の雰囲気下でE型粘度計(東機産業社製 TV−22)にて、約1.2mlを測定用試料とし、回転速度0.5〜100rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
数平均分子量(Mn)と重量平均分子量(Mw)の測定は、昭和電工社製GPC(ゲルパーミエーションクロマトグラフィー)「ShodexGPC System−21」を用いた。GPCは溶媒に溶解した物質をその分子サイズの差によって分離定量する液体クロマトグラフィーであり、溶媒としてはテトロヒドロフラン、重量平均分子量(Mn)の決定はポリスチレン換算で行った。
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容量比:トルエン/エタノール=2/1)混合液100mlを加えて溶解する。更にアセチル化剤(無水酢酸25gをピリジンで溶解し、容量100mlとした溶液)を正確に5ml加え、約1時間攪拌した。これに、フェノールフタレイン試液を指示薬として加え、30秒間持続する。その後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定する。
水酸基価は次式により求めた。水酸基価は樹脂の乾燥状態の数値とした(単位:mgKOH/g)。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
乾燥状態の樹脂の値として、酸価(mgKOH/g)を次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}/(不揮発分濃度/100)
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
ロボットDSC(示差走査熱量計、セイコーインスツルメンツ社製「RDC220」)に「SSC5200ディスクステーション」(セイコーインスツルメンツ社製)を接続して、測定に使用した。
表2の樹脂組成物を、剥離処理されたポリエステルフィルムに塗工し、活性エネルギー線を照射し、重合硬化させたものを約10mgかきとり、試料としてアルミニウムパンに入れ、秤量して示差走査熱量計にセットし、試料を入れない同タイプのアルミニウムパンをリファレンスとして、100℃の温度で5分間加熱した後、液体窒素を用いて−120℃まで急冷処理した。その後10℃/分で昇温し、昇温中に得られたDSCチャートからガラス転移温度(Tg、単位:℃)を決定した。
4HBA:アクリル酸4−ヒドロキシブチル
2HEA:アクリル酸2−ヒドロキシエチル
CHDMA:アクリル酸1,4−シクロヘキサンジメタノール
HPPA:アクリル酸2−ヒドロキシ−3−フェノキシプロピル
・化合物(B)
IBXA:アクリル酸イソボルニル
DCPA:アクリル酸ジシクロペンタニル
ADCP:ジアクリル酸ジシクロペンタニル
ACMO:4−アクリロイルモルホリン
GMA:メクリル酸グリシジル
NPGDA:ジアクリル酸ネオペンチルグリコール
・オリゴマー(D)
811:ダイセルサイテック社製 ポリエステルアクリレート「Ebecryl 811」
3000B:日本合成化学工業社製 ポリウレタン系オリゴマー(ウレタンアクリレート)「紫光UV3000B」
600:ダイセルサイテック社製 ポリエポキシ系オリゴマー(エポキシアクリレート)「Ebecryl 600」
・開始剤(E)
TPO:2,4,6−トリメチルベンゾイル-ジフェニル-フォスフィンオキサイト゛(BASF社製,DAROCUR TPO)
CPI−110P:p-フェニルチオフェニルジフェニルスルホニウムPF6塩
・シランカップリング剤(F)
A−174:タナック社製シランカップリング剤
・開始剤(G)
168:BASF社製 酸化防止剤「IRGAFOS168」
・色材(H)
表1の製造例参照。
・酸化防止剤(Q)
DIDP:フタル酸ジイソデシル(可塑剤)
を示す。
表2に示した光学的立体造形用樹脂組成物について、次の方法で力学特性を測定し、成型試験を行った。結果を表3に示す。
アプリケータを用いてガラス板上に樹脂組成物を250μm厚に塗布し、0.5J/cm2(波長 :350nm)の紫外線を照射して硬化フィルムを得た。次いで、ガラス板上から硬化フィルムを剥離し、23℃、相対湿度50%で24時間状態調節し、試験片とした。
測定23℃、相対湿度50%の恒温湿室内で、前記試験片のヤング率を引張り速度1mm/minおよび標線間25mmの条件で測定した。また23℃における前記試験片の破断伸びおよび破断強度を、引張り速度50mm/minおよび標線間25mmの条件で測定した。
このヤング率を4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
◎:120(kg/mm2)以上。全く問題なし。
○:100(kg/mm2)以上〜120(kg/mm2)未満。若干弱いが、問題なし。
△:80(kg/mm2)以上〜100(kg/mm2)未満。実用上、使用可。
×:80(kg/mm2)未満。実用上、問題あり。
光源としてArイオンレーザー(波長 351、385nm)を用いた光造形装置(ソリッドクリエーターJSC−2000:ソニー株式会社製)を使用し、液面でのレーザーパワー40mW、走査速度100cm/minで成形して試験片〔(幅50×長さ50×高さ1mm):1回の積層厚0.2mm×5回積層〕とした。
付着している樹脂液を丁寧に拭き取った後、板の重量W1 を測定した。次いで、該試験片を樹脂液中に25℃で24時間浸漬し、付着した樹脂液を拭き取った後、重量W2 を測定した。
次式により膨潤度を算出し、3段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
膨潤度(%)=〔(W2 −W1 )/W1 〕× 100
○:2(%)未満。全く問題なし。
△:2(%)以上〜5(%)未満。実用上、使用可。
×:5(%)以上。実用上、問題あり。
前述した光造形装置を用いて、液面でのレーザーパワー40mW、走査速度100cm/minで成形して試験片〔(幅50×長さ50×高さ40mm):1回の積層厚0.2mm×100回積層〕とした。
前述した光造形装置を用いて成形した(1回の積層厚 0.2mm×100回積層)。付着した樹脂液を拭き取った後、UVランプを用いてポストキュアーを行った(照射線量5J/cm2 )。
次いで、試験片の片方を水平な台に固定し、他端の持ち上がり量Δh(mm)で反りの評価を行った。
この反りを4段階で評価した。
◎:0.2(mm)未満。全く問題なし。「△」評価以上の場合、実際の使用時に特に問題ない。
○:0.2(mm)以上〜0.5(mm)未満。若干あるが、問題なし。
△:0.5(mm)以上〜1.0(mm)未満。実用上、使用可。
×:1.0(mm)以上。実用上、問題あり。
アプリケータを用いてガラス板上に樹脂組成物を250μm 厚に塗布し、0.5J/cm2(波長 :350nm)の紫外線を照射してガラス積層硬化フィルムを得、23℃、相対湿度50%で24時間状態調節し、試験片とした。
測定23℃、相対湿度50%の恒温湿室内で、前記試験片を#0000のスチールウールにより、硬化フィルムの表面を250g/cm2の荷重をかけながら10回摩擦し、耐擦傷性試験を行った。傷の発生の有無および傷の程度を目視により観察し、表面活性の指標とした。
評価は4段階で行った。「△」評価以上の場合、実際の使用時に特に問題ない。
◎:傷の発生なし。全く問題なし。
○:5本以下の傷が発生する。若干あるが、問題なし。
△:傷が6〜10本発生する。実用上、使用可。
×:傷が無数に発生する。実用上、問題あり。
Claims (3)
- 水と、
分子内に1個以上の水酸基を有するα,β−不飽和二重結合基含有化合物(A)と、
分子内に水酸基を有しないα,β−不飽和二重結合基含有化合物(B)と、開始剤(E)と
を含有する光学的立体造形用活性エネルギー線重合性樹脂組成物であり、
化合物(A)が、水酸基を有する脂肪酸エステル系(メタ)アクリル酸エステル、および水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類からなる群より選ばれる一つ以上の化合物であり、
化合物(B)が、(メタ)アクリル酸環状エステル類、2官能(メタ)アクリル酸環状エステル類、ヘテロ環状アクリルアミド類、酸素原子を有するヘテロ環含有(メタ)アクリル酸エステル類および2官能(メタ)アクリル酸エステル類からなる群より選ばれる一つ以上の化合物であり、
開始剤(E)が、光ラジカル発生剤である光学的立体造形用活性エネルギー線重合性樹脂組成物。
ただし、活性エネルギー線重合性組成物(ただし、水を除く)100重量部に対し、水を0.01〜10重量部、化合物(A)を0.5〜40重量部、および化合物(B)を20〜99重量部含有する。 - 請求項1記載の活性エネルギー線重合性樹脂組成物を、活性エネルギー線で重合硬化してなる樹脂硬化物。
- 請求項2記載の樹脂硬化物からなる立体造形物。
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