CN102660387B - 一种丙烯酸酯改性环氧大豆油及其制备方法和应用 - Google Patents
一种丙烯酸酯改性环氧大豆油及其制备方法和应用 Download PDFInfo
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- CN102660387B CN102660387B CN201210105919.8A CN201210105919A CN102660387B CN 102660387 B CN102660387 B CN 102660387B CN 201210105919 A CN201210105919 A CN 201210105919A CN 102660387 B CN102660387 B CN 102660387B
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- soybean oil
- epoxy soybean
- modified epoxy
- acrylate
- anhydride
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- 235000012424 soybean oil Nutrition 0.000 title claims abstract description 73
- 239000003549 soybean oil Substances 0.000 title claims abstract description 73
- 239000004593 Epoxy Substances 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 125000005396 acrylic acid ester group Chemical group 0.000 title abstract 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 34
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 238000007639 printing Methods 0.000 claims abstract description 10
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 8
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims abstract description 8
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 20
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 17
- -1 hydroxy acryl Chemical group 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000049 pigment Substances 0.000 abstract description 5
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 abstract description 3
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 abstract description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 abstract 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 abstract 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 abstract 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 abstract 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract 1
- GCNKJQRMNYNDBI-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(2-methylprop-2-enoyloxymethyl)butyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CC)COC(=O)C(C)=C GCNKJQRMNYNDBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 11
- 239000000976 ink Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 4
- 238000005352 clarification Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PXLDRBQDIXLCEK-UHFFFAOYSA-N C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC=CC=C1 Chemical compound C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC=CC=C1 PXLDRBQDIXLCEK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920000229 biodegradable polyester Polymers 0.000 description 1
- 239000004622 biodegradable polyester Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000008031 plastic plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
环氧大豆油改性丙烯酸酯 | 表干 | 硬度 | 柔韧性 | 附着力 | |
对照例1 | AA-ESO | OK | B | 1 | 1 |
实施例1 | HEAPTD-ESO | OK | HB | 1.5 | 0 |
实施例2 | PETAPTD-ESO | OK | F | 2.5 | 1 |
实施例3 | HEASCA-ESO | OK | B | 0.5 | 0 |
实施例4 | HEAMHHPA-ESO | OK | HB | 1.5 | 0 |
Claims (7)
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CN201210105919.8A CN102660387B (zh) | 2012-04-12 | 2012-04-12 | 一种丙烯酸酯改性环氧大豆油及其制备方法和应用 |
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CN201210105919.8A CN102660387B (zh) | 2012-04-12 | 2012-04-12 | 一种丙烯酸酯改性环氧大豆油及其制备方法和应用 |
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CN102660387B true CN102660387B (zh) | 2014-06-18 |
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CN104003874B (zh) * | 2014-04-25 | 2016-04-27 | 江苏利田科技股份有限公司 | 一种新的4官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003879A (zh) * | 2014-04-25 | 2014-08-27 | 江苏利田科技股份有限公司 | 一种2官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003877B (zh) * | 2014-04-25 | 2016-01-20 | 江苏利田科技股份有限公司 | 一种8官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003873B (zh) * | 2014-04-25 | 2016-01-20 | 江苏利田科技股份有限公司 | 一种4官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003880A (zh) * | 2014-04-25 | 2014-08-27 | 江苏利田科技股份有限公司 | 一种3官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003872A (zh) * | 2014-04-25 | 2014-08-27 | 江苏利田科技股份有限公司 | 一种新的2官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
CN104003876B (zh) * | 2014-04-25 | 2016-04-27 | 江苏利田科技股份有限公司 | 一种新的6官能度脂肪族环氧丙烯酸酯及其制备方法与应用 |
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CN107955113B (zh) * | 2017-11-29 | 2019-08-20 | 华南理工大学 | 一种无苯乙烯的柔韧型不饱和聚酯树脂及其制备方法 |
CN109180480A (zh) * | 2018-08-03 | 2019-01-11 | 武汉奥克特种化学有限公司 | 一种丙烯酸酯基羟烷基酸酯活性稀释剂及其制备方法和应用 |
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CN111454422B (zh) * | 2020-04-29 | 2021-10-01 | 东莞市冠力胶业有限公司 | 一种高剥离强度的真空吸塑胶及其制备方法 |
CN114561174B (zh) * | 2022-04-06 | 2023-04-25 | 湖南省和祥润新材料有限公司 | 一种uv固化压敏胶及其制备方法 |
CN115572446B (zh) * | 2022-09-20 | 2023-06-23 | 河南金牛新材料股份有限公司 | 一种高阻隔可降解复合包装材料及其制备方法 |
CN116199845A (zh) * | 2023-01-04 | 2023-06-02 | 广州佐晟化妆品有限公司 | 环氧大豆油基丙烯酸树脂及利用其制得的甲油胶 |
CN117003989B (zh) * | 2023-08-07 | 2024-05-17 | 广州佐晟化妆品有限公司 | 环氧大豆油基丙烯酸酯聚氨酯uv光固化树脂及所制不含tpo光引发剂的植物油基甲油胶 |
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Address after: Room 801, No. 8 Haicheng East Street, Xingang East Road, Haizhu District, Guangzhou City, Guangdong Province, 510000 Patentee after: Guangdong Boxing New Materials Technology Co.,Ltd. Address before: 510330 Room 801, Haicheng East Street, Xingang East Road, Haizhu District, Guangzhou City, Guangdong Province Patentee before: GUANGDONG BOSSIN NOVEL MATERIALS TECHNOLOGY Co.,Ltd. |