CN107652398A - A kind of high intensity 3D printing photosensitive resin material - Google Patents
A kind of high intensity 3D printing photosensitive resin material Download PDFInfo
- Publication number
- CN107652398A CN107652398A CN201710837600.7A CN201710837600A CN107652398A CN 107652398 A CN107652398 A CN 107652398A CN 201710837600 A CN201710837600 A CN 201710837600A CN 107652398 A CN107652398 A CN 107652398A
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- CN
- China
- Prior art keywords
- photosensitive resin
- parts
- resin material
- high intensity
- printing photosensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920005989 resin Polymers 0.000 title claims abstract description 43
- 239000011347 resin Substances 0.000 title claims abstract description 43
- 238000010146 3D printing Methods 0.000 title claims abstract description 33
- 239000000463 material Substances 0.000 title claims abstract description 30
- 239000000654 additive Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 239000002105 nanoparticle Substances 0.000 claims abstract description 6
- -1 olefin sulfonate Chemical class 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- DSYAPIPDAIWHFG-UHFFFAOYSA-N 1,1,1-trifluoronona-2,4-diene Chemical class FC(F)(F)C=CC=CCCCC DSYAPIPDAIWHFG-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- ZIZHEHXAMPQGEK-UHFFFAOYSA-N dirhenium decacarbonyl Chemical group [Re].[Re].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] ZIZHEHXAMPQGEK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000001506 calcium phosphate Substances 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 7
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000007493 shaping process Methods 0.000 description 5
- 238000010922 spray-dried dispersion Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000007974 melamines Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002171 ethylene diamines Chemical class 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical class C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- KRFFWELOYNJROH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 KRFFWELOYNJROH-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical class COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052956 cinnabar Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- WZWSOGGTVQXXSN-UHFFFAOYSA-N cyclohexanone;toluene Chemical compound CC1=CC=CC=C1.O=C1CCCCC1 WZWSOGGTVQXXSN-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011504 laterite Substances 0.000 description 1
- 229910001710 laterite Inorganic materials 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052957 realgar Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011276 wood tar Substances 0.000 description 1
Classifications
-
- 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
- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
- C08F267/06—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of esters
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- 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
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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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Abstract
The invention provides a kind of high intensity 3D printing photosensitive resin material, by weight, by 20~60 parts of prepolymers and 0.5~0.8 part of light trigger, 1.5~3 parts of terminators, 5~15 parts of crosslinking agents, 0.1~3 part of functional nanoparticle, 0.5~1 part of color additives, 0.5~2 part of solubilizer, mix at room temperature, polymerization, 3D printing photosensitive resin material is made.
Description
Technical field
The present invention relates to 3D(Rapid shaping and manufacture class)It is especially a kind of high such as the formula and preparation method of photosensitive resin
Intensity 3D printing photosensitive resin material.
Background technology
It for the material of photocureable rapid shaping is liquid photocurable resin that photosensitive resin, which is, or liquid photosensitive resin,
Mainly it is made up of oligomer, light trigger, diluent.Nearly 2 years, photosensitive resin had just been used for 3D printing emerging industry, photosensitive tree
Lipid 3D printing consumptive material is because its printing precision is high, and sharpness of border, surface is smooth, and interest in industry with paying attention to.
CN201510602875.3 discloses a kind of 3D printing photosensitive resin material containing modified butadiene rubber, by matter
Percentage is measured by component:Modified butadiene rubber is 10-30%;Acrylic resin is 30-80%;Diluent is 10-40%;
Initiator is 1-2%;Accelerator forms for 1-2%.The present invention obtains the polybutadiene with terminal hydroxy group by anionic polymerisation
Telechelic polymer, then be esterified with acrylic acid, introducing the effect that double bond group obtains is:By anionic synthesis methods, obtain
The narrower polymer of molecular weight distribution, beneficial to processing, rubber segment is introduced, efficiently solves the brittleness problems of generally existing, is led to
Cross and carry out esterification introducing double bond with the acrylic acid of one of the original system of photosensitive resin, consistency problem is solved at all.This
Invention additionally provides a kind of preparation method of the 3D printing photosensitive resin material containing modified butadiene rubber.
CN201510881469.5 disclose a kind of pure cationic 3D printing stereolithography rapid shaping photosensitive resin and
Preparation method and application, it is made up of by weight percent following raw material:15~95% silicone-containing cycloaliphatic epoxy resins;1~
30% oxetane compound;1~50% alicyclic epoxide compound;1~25% aliphatic epoxy compound;1~12% sun from
Subtype initiator.The material component is mixed by described quality proportioning;Then, heat, stir, i.e., in temperature 20~80
DEG C, stir 5~120 minutes, make transparent faint yellow uniform liquid.Photosensitive resin excitant prepared by the present invention it is small and
Volatile matter is few, and preparation process is easy;Light sensitivity is good, and its threshold exposure amount Ec is less than 19.0mJ/cm2.The precision of forming part is high,
The warp factor CF (6) of forming part is in the range of ± 0.01, and CF (11) is in the range of ± 0.03.The light prepared using the present invention
The part forming precision that the existing photosensitive resin of part forming ratio of precision that quick resin prints prints is higher.
3D printing for soft type, there is very strict requirement to the pliability of its consumptive material photosensitive resin, therefore, be made
3D printing material solve the matching of its mobility and the technical barrier that is matched with 3D printer of shaping speed, while solution is at present
The problems such as commercially available 3D printing strength of materials is low, coloring is difficult, comprehensive intensity, mobility and the release property for improving 3D printing material etc.
Performance, and the cost for reducing 3D printing material is that current industry breaks through difficult point.
The content of the invention
Present invention aims at solve above-mentioned technical problem present in prior art, there is provided a kind of the present invention relates to photosensitive
The formula and preparation method of resin, especially a kind of high intensity 3D printing photosensitive resin material, comprise the following steps:
1st, the preparation of prepolymer:
By weight, by 10~60 parts by photosensitive resin polymer monomer, 0.01~0.1 part of rhenium carbonyl of cyclopentadiene three, 0.1-1
Double (trifluoromethyl) -1,3- octadienes of 6,6,7,7,8,8,8- seven fluoro- 5,5- of part, 0.1-1 parts α-sodium olefin sulfonate, 0.5~2 part
Light trigger and 1~2 part of terminator, 5~20 parts of crosslinking agents, 100-200 part solvents, it is anti-that pre-polymerization is carried out at 90 DEG C~110 DEG C
Prepolymer should be made, in 1~2.5 hour reaction time, obtain prepolymer.
, 3D printing photosensitive resin preparation
By weight, by prepolymer made from 20~60 parts of above-mentioned steps 1 and 0.5~0.8 part of light trigger, 1.5~3 parts of terminations
Agent, 5~15 parts of crosslinking agents, 0.1~3 part of functional nanoparticle, 0.5~1 part of color additives, 0.5~2 part of solubilizer, room
Temperature is lower to be mixed, and polymerization, 3D printing photosensitive resin material is made
Photosensitive resin polymer monomer described in step (1) is selected from:Epoxy Acrylates compound monomer, methacrylic acid
Ester type compound monomer and acroleic acid polyurethane class compound monomer.
Solvent described in step (1) includes aromatic hydrocarbon solvent, fat hydrocarbon solvent, alicyclic hydrocarbon type solvent, halogenated hydrocarbon
Class solvent, alcohols solvent, ether solvent, esters solvent, ketones solvent, diol, derivatives and/or nitrogen-containing solvent, preferably benzene,
Toluene, dimethylbenzene, styrene, pentane, hexane, octane, hexamethylene, cyclohexanone, toluene cyclohexanone, chlorobenzene, dichloro-benzenes, dichloromethane
Alkane, chloroform, perchloroethylene, trichloro ethylene, methanol, ethanol, isopropanol, ether, expoxy propane, ethylene glycol ether, tumer
Ester, ethyl acetate, propyl acetate, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, acetonitrile, pyridine, phenol and/
Or triethanolamine.
The particle diameter of functional nanoparticle described in step 2 is 1nm~100 μm, and it includes metal oxide particle, salt
One or more in class particle, silicon-containing compound particle and nano metal powder, wherein, the metal oxide particle includes
Nano scale metal simple substance, the mixture of a variety of nano scale metal simple substances and nanoscale alloy powder, preferably nano-calcium phosphate, receive
Rice calcium carbonate, nano aluminium oxide.
Color additives described in step 2 include natural inorganic color additives and artificial color additive, wherein, day
Right inorganic color additives are selected from jet-black, chalk, cinnabar, laterite, realgar and natural iron oxide;Artificial color additive is selected from gold
Belong to oxide-based color additives and salt color additives, preferably metal oxide-type color additives, chromate face
Colour additive, carbonate color additives, Sulfates color additives, sulfide-based color additives, Nitrates face
Colour additive and acetic acid salt color additives.
Solubilizer described in step 2 is surfactant, including cationic surface active agent, anionic surface are lived
Property at least one of agent and nonionic surface active agent, be preferably, primary amine salt surfactant, secondary amine salt surfactant,
Quaternary surfactant and tertiary amine salt surfactant, heterocyclic surfactant, salt form surfactant, lecithin table
Face activating agent, amino acid type surfactant, betaine type amphoteric surfactant, fatty acid glycerine ester surfactant, sapn system
Surfactant and TWEEN Series surfactant.
Further, step 1 and step 2 kind:
The light trigger is selected from:Benzoin and its derivative, benzil class compound, alkylbenzene ketone compounds, acyl group phosphorus
Oxide, benzophenone compound, thioxanthones compound, salt compounds, metallorganic class and organosilicon alkanes
Compound;
The terminator is selected from:Quinones, nitro compound, nitroso compound, aryl polyol and sulfur-bearing
Compound, preferably hydroquinones, p-tert-Butylcatechol, wood tar, SDD, sodium polysulfide
And natrium nitrosum;
The crosslinking agent is melamine-formaldahyde crosslinking agent, aziridines crosslinking agent, polycarbodiimide class crosslinking agent, polyisocyanic acid
Class crosslinking agent, alkylene oxides crosslinking agent, metallic-ion crosslinking agent and epoxy resin crosslinking agent.
The product of the present invention has the advantages that:
A kind of 3D of the present invention(Rapid shaping and manufacture class)Such as the formula and preparation method of photosensitive resin, can solve 3D and beat
Print the requirement of material flexibility and toughness, the comprehensive intensity for improving 3D printing material.
Embodiment
Following instance is only to further illustrate the present invention, is not limitation the scope of protection of the invention.
Embodiment 1
1st, the preparation of prepolymer:
By weight, by 48.8 parts of dimethacrylates, 0.03 part of rhenium carbonyl of cyclopentadiene three, 0.2 part 6,6,
Double (trifluoromethyl) -1,3- octadienes of 7,7,8,8,8- seven fluoro- 5,5-, 0.2 part of α-sodium olefin sulfonate, 1 part of acure369
(BDMB) it is dissolved in 100 parts of dichloromethane, is carried out at 90 DEG C pre- with 1.0 parts of hydroquinones and 10.0 parts of methyl-etherified melamines
The prepolymer that the degree of polymerization is 50~200 is made in poly- reaction, and the viscosity of prepolymer is about 7000cps;
2nd, the preparation of 3D printing photosensitive resin
By weight, by prepolymer obtained above and 28.5 parts of dimethacrylates, 0.65 part of acure369
(BDMB), 2 parts of hydroquinones, 10.0 parts of methyl-etherified melamines, 1.0 parts of nano-calcium carbonates, 0.75 part of TiO2 and 1 part of octyl
Phenol APEO -10, are mixed at room temperature, polymerize and the 3D printing photosensitive resin material M-1 is made.
Embodiment 2
1st, the preparation of prepolymer:
By weight, will be by 60.0 parts of photosensitive resin polymer monomer double pentaerythritol methacrylates, 0.1 part of cyclopentadiene three
Rhenium carbonyl, 0.1 part 6, double (trifluoromethyl) -1,3- octadienes of 6,7,7,8,8,8- seven fluoro- 5,5-, 1 part of α-sodium olefin sulfonate,
2.0 parts of 4- methyl benzophenones, 2.0 parts of SDDs and 5.0 parts of methyl-etherified melamines are dissolved in 200 parts
In chloroform, prepolymerization reaction is carried out at 110 DEG C the prepolymer that the degree of polymerization is 50~200 is made, the viscosity of prepolymer is about
10000cps;
2nd, the preparation of 3D printing photosensitive resin
By weight, by prepolymer obtained above and 60.0 parts of esters of bipentaerythrite acrylic acid six, 0.8 part of 4- methyldiphenyl first
Ketone, 3.0 parts of SDDs, 15 parts of methyl-etherified melamines, 3 parts of nano-calcium phosphates, 1 part of cobalt blue and 2.0
Part AEO -7, are mixed at room temperature, polymerize and the 3D printing photosensitive resin material M-2 is made.
Embodiment 3
1st, the preparation of prepolymer:
By weight, by 10.0 parts of ethylene glycol methyl ether acrylates, 0.01 part of rhenium carbonyl of cyclopentadiene three, 1 part 6,6,7,
Double (trifluoromethyl) -1,3- octadienes of 7,8,8,8- seven fluoro- 5,5-, 0.1 part of α-sodium olefin sulfonate, 0.5 part of benzoin
(Benzoin) it is dissolved in 1.0 parts of SDDs and 20.0 parts of ethylenediamines in 150 parts of acetone, at 80 DEG C
Carry out prepolymerization reaction and the prepolymer that the degree of polymerization is 50~200 is made, the viscosity of prepolymer is about 3000cps;
2nd, the preparation of 3D printing photosensitive resin
By weight, by prepolymer obtained above and 20.0 parts of esters of bipentaerythrite acrylic acid six, 0.5 part of benzoin
(Benzoin), 1.5 parts of SDDs, 5 parts of crosslinking agent ethylenediamines, 0.1 part of nano aluminium oxide, 0.5 part
CuSO4 and 0.5 part of Tween 80 mixing, is mixed at room temperature, polymerize and the 3D printing photosensitive resin material M-3 is made.
Comparative example 1
Step 2 is added without photosensitive resin polymerized monomer, and other conditions are the same as embodiment 1.Production code member M-4.
Comparative example 2
Step 2 is added without the rhenium carbonyl of cyclopentadiene three, and other conditions are the same as embodiment 1.Production code member M-5.
Comparative example 3
Step 2 is added without double (trifluoromethyl) -1,3- octadienes of 6,6,7,7,8,8,8- seven fluoro- 5,5-, and other conditions are the same as implementation
Example 1.Production code member M-6.
Comparative example 4
Step 2 is added without functional nanoparticle, and other conditions are the same as embodiment 1.Production code member M-7.
Comparative example 5
Step 1 is cancelled, the other the same as in Example 1.Production code member M-8.
Embodiment 4
The 3D printing photosensitive resin material that embodiment 1-3 and comparative example 1-5 are produced, carry out liquid viscosity(cps/30
℃), solid carries out bending strength MPA, bending modulus MPA, elongation at break % detection after photocuring, and concrete outcome is shown in Table 1.
Table 1:The 3D printing photosensitive resin material viscosity that different process is produced(cps/30℃), solid state bending after photocuring
Intensity(MPA), bending modulus(MPA), elongation at break %/elastic recovery section % testing results.
Claims (5)
1. a kind of high intensity 3D printing photosensitive resin material, it is characterised in that its preparation method comprises the following steps:
By weight, by 20~60 parts of prepolymers and 0.5~0.8 part of light trigger, 1.5~3 parts of terminators, 5~15 parts of crosslinkings
Agent, 0.1~3 part of functional nanoparticle, 0.5~1 part of color additives, 0.5~2 part of solubilizer, are mixed at room temperature, polymerization,
3D printing photosensitive resin material is made.
A kind of 2. high intensity 3D printing photosensitive resin material described in claim 1, it is characterised in that the preparation of the prepolymer
Method comprises the following steps:
By weight, by 10~60 parts by photosensitive resin polymer monomer, 0.01~0.1 part of rhenium carbonyl of cyclopentadiene three, 0.1-1
Double (trifluoromethyl) -1,3- octadienes of 6,6,7,7,8,8,8- seven fluoro- 5,5- of part, 0.1-1 parts α-sodium olefin sulfonate, 0.5~2 part
Light trigger and 1~2 part of terminator, 5~20 parts of crosslinking agents, 100-200 part solvents, it is anti-that pre-polymerization is carried out at 90 DEG C~110 DEG C
Prepolymer should be made, in 1~2.5 hour reaction time, obtain prepolymer.
3. a kind of high intensity 3D printing photosensitive resin material described in claim 1, it is characterised in that described photosensitive resin gathers
Monomer adduct includes Epoxy Acrylates compound monomer, methyl acrylic ester compound monomer and acroleic acid polyurethane class
Compound monomer.
A kind of 4. high intensity 3D printing photosensitive resin material described in claim 1, it is characterised in that described functionalized nano
Particle includes nano-calcium phosphate, nano-calcium carbonate, nano aluminium oxide.
A kind of 5. high intensity 3D printing photosensitive resin material described in claim 1, it is characterised in that the terminator include pair
Benzenediol.
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CN104151526A (en) * | 2014-08-07 | 2014-11-19 | 浙江闪铸三维科技有限公司 | Novel photosensitive resin material applied to DLP3D printer |
CN104710573A (en) * | 2014-01-03 | 2015-06-17 | 刘毓海 | Preparation method of 3D printing material |
CN106957378A (en) * | 2017-04-07 | 2017-07-18 | 南京先临三维科技有限公司 | A kind of 3D printing preparation method of polymeric gradient material |
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CN104710573A (en) * | 2014-01-03 | 2015-06-17 | 刘毓海 | Preparation method of 3D printing material |
CN104710548A (en) * | 2014-01-03 | 2015-06-17 | 刘毓海 | 3D printing core material |
CN104151526A (en) * | 2014-08-07 | 2014-11-19 | 浙江闪铸三维科技有限公司 | Novel photosensitive resin material applied to DLP3D printer |
CN106957378A (en) * | 2017-04-07 | 2017-07-18 | 南京先临三维科技有限公司 | A kind of 3D printing preparation method of polymeric gradient material |
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