CN101838376A - 含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 - Google Patents
含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 Download PDFInfo
- Publication number
- CN101838376A CN101838376A CN201010168543A CN201010168543A CN101838376A CN 101838376 A CN101838376 A CN 101838376A CN 201010168543 A CN201010168543 A CN 201010168543A CN 201010168543 A CN201010168543 A CN 201010168543A CN 101838376 A CN101838376 A CN 101838376A
- Authority
- CN
- China
- Prior art keywords
- methyl
- acid
- citric acid
- multifunctional
- reaction
- 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.)
- Granted
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 147
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- -1 acrylic ester Chemical class 0.000 title claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- 239000000047 product Substances 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
- 230000032050 esterification Effects 0.000 claims abstract description 16
- 238000005886 esterification reaction Methods 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 12
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 8
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 238000007046 ethoxylation reaction Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 6
- 229940117969 neopentyl glycol Drugs 0.000 claims description 6
- 229940059574 pentaerithrityl Drugs 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 4
- 229940051250 hexylene glycol Drugs 0.000 claims description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 claims description 2
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 claims description 2
- ZCHGODLGROULLT-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;propane-1,2-diol Chemical compound CC(O)CO.OCC(CO)(CO)CO ZCHGODLGROULLT-UHFFFAOYSA-N 0.000 claims description 2
- YMHOBZXQZVXHBM-UHFFFAOYSA-N 2,5-dimethoxy-4-bromophenethylamine Chemical compound COC1=CC(CCN)=C(OC)C=C1Br YMHOBZXQZVXHBM-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 2
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000004258 Ethoxyquin Substances 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 241000545067 Venus Species 0.000 claims description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 claims description 2
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims description 2
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 claims description 2
- MUAXETKHGSOSCB-UHFFFAOYSA-N copper;2-methylprop-2-enoic acid Chemical compound [Cu].CC(=C)C(O)=O MUAXETKHGSOSCB-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 2
- 235000019800 disodium phosphate Nutrition 0.000 claims description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940093500 ethoxyquin Drugs 0.000 claims description 2
- 235000019285 ethoxyquin Nutrition 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 claims description 2
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 2
- JNQXVIAROPTRDY-UHFFFAOYSA-N manganese;2-methylprop-2-enoic acid Chemical compound [Mn].CC(=C)C(O)=O JNQXVIAROPTRDY-UHFFFAOYSA-N 0.000 claims description 2
- DMZUKDRIRUYBIU-UHFFFAOYSA-N manganese;prop-2-enoic acid Chemical compound [Mn].OC(=O)C=C DMZUKDRIRUYBIU-UHFFFAOYSA-N 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- GQKZRWSUJHVIPE-UHFFFAOYSA-N sec-amyl acetate Natural products CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 abstract description 7
- 230000005855 radiation Effects 0.000 abstract description 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 4
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- 238000007711 solidification Methods 0.000 abstract 1
- 230000008023 solidification Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000003518 caustics Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010168543.6A CN101838376B (zh) | 2010-05-11 | 2010-05-11 | 含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010168543.6A CN101838376B (zh) | 2010-05-11 | 2010-05-11 | 含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101838376A true CN101838376A (zh) | 2010-09-22 |
CN101838376B CN101838376B (zh) | 2014-03-26 |
Family
ID=42742070
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201010168543.6A Active CN101838376B (zh) | 2010-05-11 | 2010-05-11 | 含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101838376B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102311455A (zh) * | 2011-05-19 | 2012-01-11 | 张春华 | 可辐射固化的含膦酸基的多官能(甲基)丙烯酸酯的组合物及其制备方法 |
CN103524344A (zh) * | 2013-10-11 | 2014-01-22 | 天津市天骄化工有限公司 | 一种乙氧基化(2)1,6-己二醇二丙烯酸酯的制备方法 |
CN106317462A (zh) * | 2016-08-23 | 2017-01-11 | 成都米特瑞新材料科技有限公司 | 一种具有阻燃性的柠檬酸增塑剂的制备方法 |
CN108865040A (zh) * | 2018-06-26 | 2018-11-23 | 合肥萃励新材料科技有限公司 | 一种过流保护导电压敏胶的合成方法 |
CN111992191A (zh) * | 2020-08-26 | 2020-11-27 | 广西大学 | 一种快速高容量智能型纤维素基吸油材料及其制备方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474981A (en) * | 1981-08-11 | 1984-10-02 | Sumitomo Chemical Company, Limited | Process for preparing an acrylic or methacrylic acid ester |
CN1066859A (zh) * | 1991-02-20 | 1992-12-09 | 诺瓦蒙特股份公司 | 基于淀粉和热塑性聚合物的可生物降解的聚合物组合物 |
JP2007008828A (ja) * | 2005-06-28 | 2007-01-18 | Toagosei Co Ltd | アクリル酸エステル又はメタクリル酸エステルの製造方法 |
-
2010
- 2010-05-11 CN CN201010168543.6A patent/CN101838376B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474981A (en) * | 1981-08-11 | 1984-10-02 | Sumitomo Chemical Company, Limited | Process for preparing an acrylic or methacrylic acid ester |
CN1066859A (zh) * | 1991-02-20 | 1992-12-09 | 诺瓦蒙特股份公司 | 基于淀粉和热塑性聚合物的可生物降解的聚合物组合物 |
JP2007008828A (ja) * | 2005-06-28 | 2007-01-18 | Toagosei Co Ltd | アクリル酸エステル又はメタクリル酸エステルの製造方法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102311455A (zh) * | 2011-05-19 | 2012-01-11 | 张春华 | 可辐射固化的含膦酸基的多官能(甲基)丙烯酸酯的组合物及其制备方法 |
CN103524344A (zh) * | 2013-10-11 | 2014-01-22 | 天津市天骄化工有限公司 | 一种乙氧基化(2)1,6-己二醇二丙烯酸酯的制备方法 |
CN103524344B (zh) * | 2013-10-11 | 2015-11-18 | 天津市天骄辐射固化材料有限公司 | 一种乙氧基化(2)1,6-己二醇二丙烯酸酯的制备方法 |
CN106317462A (zh) * | 2016-08-23 | 2017-01-11 | 成都米特瑞新材料科技有限公司 | 一种具有阻燃性的柠檬酸增塑剂的制备方法 |
CN108865040A (zh) * | 2018-06-26 | 2018-11-23 | 合肥萃励新材料科技有限公司 | 一种过流保护导电压敏胶的合成方法 |
CN111992191A (zh) * | 2020-08-26 | 2020-11-27 | 广西大学 | 一种快速高容量智能型纤维素基吸油材料及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN101838376B (zh) | 2014-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101838376B (zh) | 含柠檬酸衍生的支化的多官能(甲基)丙烯酸酯组合物 | |
CN101838377B (zh) | 可辐射固化的多官能(甲基)丙烯酸酯的组合物 | |
US5424466A (en) | Improved process for the production of esters from fatty substances having a natural origin | |
US5648518A (en) | Process for producing esters of (meth) acrylic acid and polyhydric alcohols | |
CN103102478B (zh) | 一种腰果壳油醇酸树脂及其制备方法 | |
CN101148497A (zh) | 自干型水溶性醇酸树脂及其制备方法 | |
CN106916053A (zh) | 一种2,4‑二取代基苯酚制备联苯二酚的绿色生产工艺 | |
CN105368537A (zh) | 一种酯类润滑油基础油及其合成方法 | |
TW201821500A (zh) | 基於回收的pet之(甲基)丙烯酸酯化的化合物 | |
CN1684935A (zh) | 羟基苯甲酸类的制备方法 | |
CN101768256A (zh) | 一种水分散型短油聚酯树脂的制备方法 | |
CN111138278B (zh) | 一种丁二醇辛酸酯的制备方法 | |
CN106188514A (zh) | 一种水性妥尔油醇酸树脂乳液及其制备方法 | |
CN102311455A (zh) | 可辐射固化的含膦酸基的多官能(甲基)丙烯酸酯的组合物及其制备方法 | |
EP1799746A1 (de) | Verfahren zur herstellung von polyestern | |
CN101443305B (zh) | (甲基)丙烯酸酯的制造方法 | |
CN106188085B (zh) | 一种制备荧光素的工艺方法 | |
CN101716520A (zh) | 一种用于制备多聚甘油的催化剂的制备方法及应用 | |
CN114874421A (zh) | 一种低醛酮含量聚酯多元醇及其制备方法和应用 | |
CN101338197A (zh) | 3-(3,5-二叔丁基-4-羟基苯基)丙烯酸酯类抗氧剂及其制备方法 | |
CN114181219A (zh) | 一种烷基聚氧乙烯醚在铜酞菁合成过程中的应用方法 | |
CN107876037A (zh) | 固体碱催化剂、其制备方法、应用及利用其催化制备二元醇二醋酸酯的方法 | |
CN112371101A (zh) | 一种催化脂肪酸酯化反应的催化剂和脂肪酸酯绿色合成方法 | |
CN102826996A (zh) | 双醋瑞因的合成工艺 | |
CN108840998A (zh) | 一种具有改善的低温流动性的聚酯多元醇及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: HENGYANG YUTU POLYMER MATERIALS CO., LTD. Free format text: FORMER OWNER: ZHANG CHUNHUA Effective date: 20150818 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20150818 Address after: 421001 Hunan city of Hengyang Province Jin Jia Ling of Zhuhui District No. 1 Patentee after: Hengyang rabbit high polymer material Co.,Ltd. Address before: Department of chemistry and materials science Hengyang Normal University No. 165 421008 Hunan city of Hengyang Province Huang Bai Lu Yanfeng District Patentee before: Zhang Chunhua |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160711 Address after: 421001 Hunan province Hengyang Zhuhui District, Cha Shan Ao Jin Jia Ling Patentee after: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Address before: 421001 Hunan city of Hengyang Province Jin Jia Ling of Zhuhui District No. 1 Patentee before: Hengyang rabbit high polymer material Co.,Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Derived and branched multifunctional (methyl) acrylic ester composition containing citric acid Effective date of registration: 20190102 Granted publication date: 20140326 Pledgee: China Construction Bank Co.,Ltd. Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: 2018430000151 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20210205 Granted publication date: 20140326 Pledgee: China Construction Bank Co.,Ltd. Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL Co.,Ltd. Registration number: 2018430000151 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Branched multifunctional (meth) acrylate composition containing citric acid derived Effective date of registration: 20211108 Granted publication date: 20140326 Pledgee: Agricultural Bank of China Limited Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2021980012017 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220601 Granted publication date: 20140326 Pledgee: Agricultural Bank of China Limited Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2021980012017 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Citric acid-derived branched polyfunctional (meth)acrylate compositions Effective date of registration: 20220916 Granted publication date: 20140326 Pledgee: Bank of Beijing Limited by Share Ltd. Changsha branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2022430000086 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230725 Granted publication date: 20140326 Pledgee: Bank of Beijing Limited by Share Ltd. Changsha branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2022430000086 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Branched multifunctional (methyl) acrylate composition containing citric acid derivatives Effective date of registration: 20230920 Granted publication date: 20140326 Pledgee: Agricultural Bank of China Limited Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2023980057683 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20140326 Pledgee: Agricultural Bank of China Limited Hengyang Branch Pledgor: HUNAN CHUANGDA YUTU CHEMICAL CO.,LTD. Registration number: Y2023980057683 |