JP7443569B2 - 硬化性樹脂組成物、3dプリンター用硬化性樹脂組成物および樹脂硬化物 - Google Patents
硬化性樹脂組成物、3dプリンター用硬化性樹脂組成物および樹脂硬化物 Download PDFInfo
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- JP7443569B2 JP7443569B2 JP2022573113A JP2022573113A JP7443569B2 JP 7443569 B2 JP7443569 B2 JP 7443569B2 JP 2022573113 A JP2022573113 A JP 2022573113A JP 2022573113 A JP2022573113 A JP 2022573113A JP 7443569 B2 JP7443569 B2 JP 7443569B2
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- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- WDXUZXYGVVQRBC-UHFFFAOYSA-N dibutyl 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate Chemical compound C1C(C(=O)OCCCC)C(C(=O)OCCCC)CC2OC21 WDXUZXYGVVQRBC-UHFFFAOYSA-N 0.000 description 1
- ANSWCYTXKAIJOK-UHFFFAOYSA-N dibutyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1CCCCC1C(=O)OCCCC ANSWCYTXKAIJOK-UHFFFAOYSA-N 0.000 description 1
- DQAIJLIWTPSECO-UHFFFAOYSA-N dibutyl cyclohexane-1,3-dicarboxylate Chemical compound CCCCOC(=O)C1CCCC(C(=O)OCCCC)C1 DQAIJLIWTPSECO-UHFFFAOYSA-N 0.000 description 1
- QGUFKMSGOYILME-UHFFFAOYSA-N dibutyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCOC(=O)C1CCC(C(=O)OCCCC)CC1 QGUFKMSGOYILME-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- IYOROGQDQVJIGK-UHFFFAOYSA-N diethyl 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate Chemical compound C1C(C(=O)OCC)C(C(=O)OCC)CC2OC21 IYOROGQDQVJIGK-UHFFFAOYSA-N 0.000 description 1
- ZTUZDYWYNQDJKR-UHFFFAOYSA-N diethyl cyclohexane-1,2-dicarboxylate Chemical compound CCOC(=O)C1CCCCC1C(=O)OCC ZTUZDYWYNQDJKR-UHFFFAOYSA-N 0.000 description 1
- MAQGUOIUBYAVNL-UHFFFAOYSA-N diethyl cyclohexane-1,3-dicarboxylate Chemical compound CCOC(=O)C1CCCC(C(=O)OCC)C1 MAQGUOIUBYAVNL-UHFFFAOYSA-N 0.000 description 1
- KRJHRNUTLDTSKY-UHFFFAOYSA-N diethyl cyclohexane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCC(C(=O)OCC)CC1 KRJHRNUTLDTSKY-UHFFFAOYSA-N 0.000 description 1
- YKDMBTQVKVEMSA-UHFFFAOYSA-N diethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOC(=O)CCCCCCCCCCCCCCCCC YKDMBTQVKVEMSA-UHFFFAOYSA-N 0.000 description 1
- 229940111071 diethylene glycol distearate Drugs 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- BTSNCLCMCHPTBO-UHFFFAOYSA-N dimethyl 7-oxabicyclo[4.1.0]heptane-2,3-dicarboxylate Chemical compound COC(C1C(C(=O)OC)C2C(CC1)O2)=O BTSNCLCMCHPTBO-UHFFFAOYSA-N 0.000 description 1
- OBOPQSIGGSCTEL-UHFFFAOYSA-N dimethyl 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate Chemical compound C1C(C(=O)OC)C(C(=O)OC)CC2OC21 OBOPQSIGGSCTEL-UHFFFAOYSA-N 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- FUXJJBJXVZIIMV-UHFFFAOYSA-N dioctyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCC FUXJJBJXVZIIMV-UHFFFAOYSA-N 0.000 description 1
- BYGQIUHOWVUUPS-UHFFFAOYSA-N dioctyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCC)CC1 BYGQIUHOWVUUPS-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QQVHEQUEHCEAKS-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QQVHEQUEHCEAKS-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- DBIKWHSBKVRPBS-UHFFFAOYSA-N n,3,3,5-tetramethylcyclohexan-1-amine Chemical compound CNC1CC(C)CC(C)(C)C1 DBIKWHSBKVRPBS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 229920001778 nylon Polymers 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
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 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
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000002784 sclerotic effect Effects 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- GNCDUZFXTFAOBE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) benzene-1,2,4,5-tetracarboxylate Chemical compound CCCCC(CC)COC(=O)C1=CC(C(=O)OCC(CC)CCCC)=C(C(=O)OCC(CC)CCCC)C=C1C(=O)OCC(CC)CCCC GNCDUZFXTFAOBE-UHFFFAOYSA-N 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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-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
- WDRCVXGINNJWPH-UHFFFAOYSA-N tris(6-methylheptyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)=C1 WDRCVXGINNJWPH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- 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
- B29C64/20—Apparatus for additive manufacturing; Details thereof or accessories therefor
- B29C64/264—Arrangements for irradiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B33Y10/00—Processes of additive manufacturing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Optics & Photonics (AREA)
- Toxicology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を活性エネルギー線硬化させ、硬化膜を得る。
そのため、硬化性樹脂組成物および3Dプリンター用硬化性樹脂組成物は、優れた低照度硬化性と優れた薄膜造形性とを有し、低硬度性に優れた樹脂硬化物を得ることができる。
なお、(メタ)アクリロイルとは、アクリロイルおよび/またはメタクリロイルを示す。
また、(メタ)アクリルとは、アクリルおよび/またはメタクリルを示(メタ)アクリレートとは、アクリレートおよび/またはメタクリレートを示す。
)が挙げられる。
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を活性エネルギー線硬化させ、硬化膜を得る。
(1)イソシアネート基末端プレポリマーの合成
表1~表12に記載の処方に従って、イソシアネート基末端プレポリマーを合成した。より具体的には、表1~表12に記載の処方に従って、窒素雰囲気下、ガラス製のセパラブルフラスコに、ポリオール成分を投入した。次いで、セパラブルフラスコに、ポリイソシアネート成分を、当量比(NCO/OH)8.0となる割合で投入した。その後、混合物を、80℃に昇温した。その後、ウレタン化触媒としてのスタノクト(エチルヘキサン酸スズ(II))を、混合物に対して10ppmとなる割合で投入した。その後、混合物を4時間反応させた。これにより、イソシアネート基末端プレポリマーと、未反応のポリイソシアネート成分とを含む粗生成物を得た。
イソシアネート基末端プレポリマーを含む粗生成物を、スミス式薄膜蒸留装置にセットし、以下の条件で、イソシアネート基末端プレポリマーと、未反応のポリイソシアネート成分とを分離した。これにより、イソシアネート基末端プレポリマーを精製した。
圧力条件:70~100Pa
供給流量:3.5-4g/min
(3)活性エネルギー線硬化性ポリウレタン樹脂の合成
表1~表12に記載の処方に従って、大気下(ドライエアー下)、セパラブルフラスコに、精製したイソシアネート基末端プレポリマー(プレポリマー精製物)を投入した。次いで、セパラブルフラスコに、ヒドロキシ基含有不飽和化合物を、ヒドロキシ基含有不飽和化合物のヒドロキシ基に対するイソシアネート基末端プレポリマーのイソシアネート基の当量比(NCO/OH)が1.0となる割合で投入した。次いで、混合物を70℃に昇温した。
表1~表12に記載の処方に従って、活性エネルギー線硬化性ポリウレタン樹脂と、エステル系可塑剤、内部離型剤およびオレフィン類からなる群から選択される少なくとも1種と、ラジカル反応性希釈剤と、活性エネルギー線重合開始剤と、添加剤とを、合計100gとなるように褐色瓶に投入し、60℃で撹拌した。これにより、硬化性樹脂組成物を得た。
以下に示す方法で、硬化性樹脂組成物を硬化させ、樹脂硬化物を得た。
(1)外観
樹脂硬化物の外観を、目視で観察した。
3Dプリンターを用いて、下記の方法を繰り返して硬化膜を積層した。これにより、樹脂硬化物として、直径100mm×高さ25mmの円柱成型物を製造した。
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を、活性エネルギー線硬化させ、硬化膜を得る。
3Dプリンターを用いて、下記の方法を繰り返して硬化膜を積層した。これにより、樹脂硬化物として、直径30mm×高さ15mmの円柱成型物を製造した。
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を、活性エネルギー線硬化させ、硬化膜を得る。
◎:成形物が指に粘着せず、指がべたつかなかった。
○:成形物が指に粘着しないが、指がべたついた。
△:成形物が指に粘着した。
3Dプリンターを用いて、下記の方法を繰り返して硬化膜を積層した。これにより、樹脂硬化物として、直径40mm×最大高さ30mmの半球状成型物を製造した。
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を、活性エネルギー線硬化させ、硬化膜を得る。
△:成形物が千切れて縫合が困難であった。
IPDI:イソホロンジイソシアネート、商品名VESTANAT IPDI、Evonik製
H12MDI:4,4’-メチレンビス(シクロヘキシルイソシアネート)、商品名VESTANAT H12MDI、Evonik製
D2000:ポリオキシプロピレンポリオール、平均官能基数2、数平均分子量2000、三井化学SKCポリウレタン製
DL4000:ポリオキシプロピレンポリオール、平均官能基数2、数平均分子量4000、三井化学SKCポリウレタン製
DL6000:ポリオキシプロピレンポリオール、平均官能基数2、数平均分子量6000、三井化学SKCポリウレタン製
DL10000:ポリオキシプロピレンポリオール、平均官能基数2、数平均分子量10000、三井化学SKCポリウレタン製
DL12000:ポリオキシプロピレンポリオール、平均官能基数2、数平均分子量12000、三井化学SKCポリウレタン製
HEA:2-ヒドロキシエチルアクリレート
EHDG-AT:ラジカル反応性希釈剤、2-エチルヘキシル-ジグルコールアクリレート、鎖状エーテル骨格を有する反応性化合物、共栄社化学製
IBXA:ラジカル反応性希釈剤、イソボルニルアクリレート、脂環式炭化水素骨格を有する反応性化合物、大阪有機化学工業製
ACMO-LI:ラジカル反応性希釈剤、4-アクリロイルモルフォリン、脂環式エーテル骨格を有する反応性化合物、KJケミカルズ製
A-DOD-N:ラジカル反応性希釈剤、1,10-デカンジオールジアクリレート、(メタ)アクリロイル基およびビニル基併有化合物、新中村化学工業製
ビスコートCHA:ラジカル反応性希釈剤、シクロヘキシルアクリレート、脂環式炭化水素骨格を有する反応性化合物、大阪有機化学工業製
4HBA:ラジカル反応性希釈剤、4-ヒドロキシブチルアクリレート、ヒドロキシ基含有(メタ)アクリレート
ビスコート200:ラジカル反応性希釈剤、環状トリメチロールプロパンホルマールアクリレート(別名(5-エチル-1,3-ジオキサン-5-イル)メチルアクリラート)、脂環式エーテル骨格を有する反応性化合物、大阪有機化学工業製
MEDOL-10:ラジカル反応性希釈剤、(2ーメチル-2-エチル-1,3-ジオキソラン-4-イル)メチルアクリレート、脂環式エーテル骨格を有する反応性化合物、大阪有機化学工業製
AO-MA:ラジカル反応性希釈剤、2-(アリルオキシメチル)アクリル酸メチル、(メタ)アクリロイル基およびビニル基併有化合物、日本触媒製
サーフロンS-386:内部離型剤、フッ素系界面活性剤、AGCセイミケミカル製サーフロンS-658:内部離型剤、フッ素系界面活性剤、AGCセイミケミカル製サーフロンS-242:内部離型剤、フッ素系界面活性剤、AGCセイミケミカル製IF-FN1916:内部離型剤、フッ素系界面活性剤、AGCセイミケミカル製
ディスパロンLS-460:内部離型剤、変性シリコーン、楠本化成社製
ディスパロンLS-480:内部離型剤、変性シリコーン、楠本化成社製
DOWSIL SH 8700 Fluid:内部離型剤、ポリエーテル変性シリコーン、ダウ・ ケミカル社製
DOWSIL SH 8417 Fluid:内部離型剤、アミノ変性シリコーンオイル、ダウ・ケミカル社製
DOWSIL BY 16-201:内部離型剤、ポリジメチルシロキサンエチレングリコール、ダウ・ケミカル社製
Omnirad819:光重合開始剤、ビス(2,4,6-トリメチルベンゾイル)フェニルフォルフィンオキサイド、IGM resinsB.V.社製
リニアレン168:オレフィン単量体、炭素数16~18のオレフィン、出光興産製ルーカント HC-40:エチレン-αオレフィンオリゴマー、三井化学製
ルーカント LX020:エチレン-αオレフィンオリゴマー、三井化学製
ルーカント 酸変性LC A-5515:エチレン-αオレフィンオリゴマー、三井化学製
ルーカント OH変性LC:エチレン-αオレフィンオリゴマー、三井化学製
X-22-2445:潤滑剤、反応性シリコーンオイル、信越シリコーン製
KMP-602:潤滑剤、シリコーンパウダー、信越シリコーン製
KMP-605:潤滑剤、シリコーンパウダー、信越シリコーン製
Irganox245:酸化防止剤、ビス[3-(3-メチル-4-ヒドロキシ-5-tert-ブチルフェニル)プロピオン酸]エチレンビスオキシビスエチレン、BASFジャパン社製
Claims (5)
- 活性エネルギー線硬化性ポリウレタン樹脂と、
エステル系可塑剤、内部離型剤およびオレフィン類からなる群から選択される少なくとも1種と、
ラジカル反応性希釈剤と、
活性エネルギー線重合開始剤とを含有し、
前記エステル系可塑剤は、ジプロピレングリコールジベンゾアートを含有し、
前記オレフィン類は、炭素数16~18のオレフィンを含有し、
前記活性エネルギー線硬化性ポリウレタン樹脂は、アクリロイルオキシ基を有し、
前記ラジカル反応性希釈剤は、アクリロイルオキシ基を有し、
前記活性エネルギー線重合開始剤は、ラジカル重合系光重合開始剤を含有し、
前記活性エネルギー線硬化性ポリウレタン樹脂100質量部に対して、
前記エステル系可塑剤、前記内部離型剤および前記オレフィン類の含有割合の総量が、100質量部以上1500質量部以下であり、
前記活性エネルギー線重合開始剤の含有割合が、2.5質量部以上5.0質量部以下である、硬化性樹脂組成物。 - 下記の硬化膜を積層した直径100mm×高さ25mmの円柱成型物のアスカーC硬度が40以下であり、アスカーF硬度が1以上である、請求項1に記載の硬化性樹脂組成物。
(1)膜厚100μmの硬化性樹脂組成物の塗膜を得る。
(2)硬化性樹脂組成物の塗膜を、活性エネルギー線硬化させ、硬化膜を得る。 - 請求項1に記載の硬化性樹脂組成物を含む、3Dプリンター用硬化性樹脂組成物。
- 請求項1に記載の硬化性樹脂組成物の硬化物である、樹脂硬化物。
- アスカーC硬度が40以下であり、アスカーF硬度が1以上である、請求項4に記載の樹脂硬化物。
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