CN105482713A - 一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 - Google Patents
一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 Download PDFInfo
- Publication number
- CN105482713A CN105482713A CN201511008352.2A CN201511008352A CN105482713A CN 105482713 A CN105482713 A CN 105482713A CN 201511008352 A CN201511008352 A CN 201511008352A CN 105482713 A CN105482713 A CN 105482713A
- Authority
- CN
- China
- Prior art keywords
- height
- glycidyl methacrylate
- nilox resin
- preparation
- resin
- 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
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 title claims abstract description 89
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 48
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 44
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 229920005989 resin Polymers 0.000 claims abstract description 135
- 239000011347 resin Substances 0.000 claims abstract description 135
- 238000000034 method Methods 0.000 claims abstract description 25
- ZRIHAIZYIMGOAB-UHFFFAOYSA-N butabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=O)NC1=O ZRIHAIZYIMGOAB-UHFFFAOYSA-N 0.000 claims description 112
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000002844 melting Methods 0.000 claims description 18
- 230000008018 melting Effects 0.000 claims description 18
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 15
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 15
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 15
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 15
- 238000005886 esterification reaction Methods 0.000 claims description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- 239000012298 atmosphere Substances 0.000 claims description 11
- 239000011261 inert gas Substances 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910001510 metal chloride Inorganic materials 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- ZSAIDYISADJCTG-UHFFFAOYSA-N CC(CCCCCCC)P(CCCCCCCC)CCCCCCCC Chemical compound CC(CCCCCCC)P(CCCCCCCC)CCCCCCCC ZSAIDYISADJCTG-UHFFFAOYSA-N 0.000 claims description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 2
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 229960004418 trolamine Drugs 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 abstract description 24
- 229920000647 polyepoxide Polymers 0.000 abstract description 24
- 239000002994 raw material Substances 0.000 abstract description 4
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 2
- 230000006750 UV protection Effects 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 10
- -1 cyclohexyl compound Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 4
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 235000019687 Lamb Nutrition 0.000 description 3
- 235000011609 Pinus massoniana Nutrition 0.000 description 3
- 241000018650 Pinus massoniana Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002924 oxiranes Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011615 Pinus koraiensis Nutrition 0.000 description 1
- 240000007263 Pinus koraiensis Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000007520 diprotic acids Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- FEPCMSPFPMPWJK-OLPJDRRASA-N maleopimaric acid Chemical compound C([C@]12C=C([C@H](C[C@@H]11)[C@H]3C(OC(=O)[C@@H]23)=O)C(C)C)C[C@@H]2[C@]1(C)CCC[C@@]2(C)C(O)=O FEPCMSPFPMPWJK-OLPJDRRASA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000036561 sun exposure Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201511008352.2A CN105482713B (zh) | 2015-12-25 | 2015-12-25 | 一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201511008352.2A CN105482713B (zh) | 2015-12-25 | 2015-12-25 | 一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105482713A true CN105482713A (zh) | 2016-04-13 |
CN105482713B CN105482713B (zh) | 2018-08-07 |
Family
ID=55669999
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201511008352.2A Active CN105482713B (zh) | 2015-12-25 | 2015-12-25 | 一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105482713B (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106008921A (zh) * | 2016-05-20 | 2016-10-12 | 中国林业科学研究院林产化学工业研究所 | 一种松香基多元胺导电环氧固化剂及其制备方法和应用 |
CN109112021A (zh) * | 2018-06-25 | 2019-01-01 | 广东科茂林产化工股份有限公司 | 一种歧化松香钾皂的制备方法 |
CN109503382A (zh) * | 2018-12-17 | 2019-03-22 | 中国林业科学研究院林产化学工业研究所 | 一种12位苯并环丁烯脱氢枞酸(β-甲基丙烯酰氧基乙基)酯、其制备方法及其应用 |
CN109868066A (zh) * | 2018-08-28 | 2019-06-11 | 中国林业科学研究院林产化学工业研究所 | 松香基co2/n2响应型表面活性剂及制备方法和用途 |
CN109897551A (zh) * | 2019-02-21 | 2019-06-18 | 广西藤县通轩立信化学有限公司 | 一种环氧基烯烃及烯烃醚改性聚合松香树脂 |
CN110713797A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧接枝松香及其制备方法、包含该环氧接枝松香的组合物及其应用 |
CN110776607A (zh) * | 2019-10-12 | 2020-02-11 | 青岛大学 | 一种新型活性共聚物高凝原油驱油剂的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5825315A (ja) * | 1981-08-06 | 1983-02-15 | Osaka Soda Co Ltd | (メタ)アクリル酸グリシジル−ロジン付加物の製法 |
CN102337078A (zh) * | 2011-07-07 | 2012-02-01 | 景东力奥林产集团林业化工有限公司 | 松香树脂生产工艺 |
CN104262549A (zh) * | 2014-09-14 | 2015-01-07 | 桂林理工大学 | 用松香甲基丙烯酸缩水甘油酯酯化物合成聚合物微球的方法 |
-
2015
- 2015-12-25 CN CN201511008352.2A patent/CN105482713B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5825315A (ja) * | 1981-08-06 | 1983-02-15 | Osaka Soda Co Ltd | (メタ)アクリル酸グリシジル−ロジン付加物の製法 |
CN102337078A (zh) * | 2011-07-07 | 2012-02-01 | 景东力奥林产集团林业化工有限公司 | 松香树脂生产工艺 |
CN104262549A (zh) * | 2014-09-14 | 2015-01-07 | 桂林理工大学 | 用松香甲基丙烯酸缩水甘油酯酯化物合成聚合物微球的方法 |
Non-Patent Citations (3)
Title |
---|
任鹏等: "《松香和甲基丙烯酸缩水甘油酯酯化反应研究》", 《化学研究与应用》 * |
歧化松香乙烯基酯单体及其与苯乙烯共聚材料的制备与性能: "《歧化松香乙烯基酯单体及其与苯乙烯共聚材料的制备与性能》", 《工程塑料应用》 * |
韩长日: "《实用化学品配方手册(九)》", 31 January 1997, 四川科学技术出版社 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106008921A (zh) * | 2016-05-20 | 2016-10-12 | 中国林业科学研究院林产化学工业研究所 | 一种松香基多元胺导电环氧固化剂及其制备方法和应用 |
CN109112021A (zh) * | 2018-06-25 | 2019-01-01 | 广东科茂林产化工股份有限公司 | 一种歧化松香钾皂的制备方法 |
CN109112021B (zh) * | 2018-06-25 | 2021-03-30 | 广东科茂林产化工股份有限公司 | 一种歧化松香钾皂的制备方法 |
CN110713797A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧接枝松香及其制备方法、包含该环氧接枝松香的组合物及其应用 |
CN109868066A (zh) * | 2018-08-28 | 2019-06-11 | 中国林业科学研究院林产化学工业研究所 | 松香基co2/n2响应型表面活性剂及制备方法和用途 |
CN109503382A (zh) * | 2018-12-17 | 2019-03-22 | 中国林业科学研究院林产化学工业研究所 | 一种12位苯并环丁烯脱氢枞酸(β-甲基丙烯酰氧基乙基)酯、其制备方法及其应用 |
CN109503382B (zh) * | 2018-12-17 | 2021-03-19 | 中国林业科学研究院林产化学工业研究所 | 一种12位苯并环丁烯脱氢枞酸(β-甲基丙烯酰氧基乙基)酯、其制备方法及其应用 |
CN109897551A (zh) * | 2019-02-21 | 2019-06-18 | 广西藤县通轩立信化学有限公司 | 一种环氧基烯烃及烯烃醚改性聚合松香树脂 |
CN110776607A (zh) * | 2019-10-12 | 2020-02-11 | 青岛大学 | 一种新型活性共聚物高凝原油驱油剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN105482713B (zh) | 2018-08-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105482713A (zh) | 一种高度歧化松香甲基丙烯酸缩水甘油酯及其制备方法 | |
CN101544744B (zh) | 丙烯酸松香环氧树脂预聚体及其制备方法 | |
CN110066383B (zh) | 一种离子型的水性环氧固化剂及其制备方法和应用 | |
CN101555386B (zh) | 一种(甲基)丙烯酸改性环氧化有机硅紫外光固化涂料及其制备方法 | |
CN102924690B (zh) | 一种超支化聚醚型环氧树脂用于增韧增强的环氧树脂材料及其制备方法 | |
CN102206324B (zh) | 一种全生物基环氧树脂组合物及其固化物 | |
CN102321232B (zh) | 一种水溶性超支化环氧树脂及其制备方法 | |
CN108641066B (zh) | 一种环氧树脂组合物及其制备方法 | |
CN109384775A (zh) | 一种含环状酰胺结构的生物基环氧树脂前驱体及其制备方法和应用 | |
CN104892858A (zh) | 一种高生物基含量环氧树脂组合物及其固化方法和应用 | |
CN102827105A (zh) | 一种改性双酚a型环氧树脂及其制备方法 | |
CN111040131A (zh) | 一种基于儿茶酸的环氧树脂的合成和应用 | |
WO2024174291A1 (zh) | 生物质环氧单体、自固化环氧树脂及其制备方法 | |
CN106700033B (zh) | 一种阳离子型可见光固化组合物 | |
CN102627930A (zh) | 一种风轮叶片用环氧结构胶及其制备方法 | |
CN102250318A (zh) | 一种全松香基环氧树脂组合物及其固化物 | |
CN108129639A (zh) | 一种环氧树脂固化剂及制备方法 | |
CN109777040A (zh) | 一种生物质基可回收型环氧树脂及其制备方法和应用 | |
CN109825036A (zh) | 一种改性环氧树脂及其制备方法 | |
CN106519712B (zh) | 一种高性能全生物基环氧大豆油树脂及其制备方法 | |
CN102826995A (zh) | 低粘度松节油基单萜乙烯基酯树脂单体及其制备方法和应用 | |
CN109535655B (zh) | 一种环氧大豆油马来酰亚胺及其制备方法和应用 | |
CN104744703B (zh) | 一种含硅的桐油基醇酸树脂及其制备方法和应用 | |
JP4273530B2 (ja) | 環状カーボナート樹脂組成物及びその硬化物 | |
CN104341375A (zh) | 一种聚合松香二缩水甘油酯环氧树脂及其制备方法 |
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 | ||
TR01 | Transfer of patent right |
Effective date of registration: 20211216 Address after: 532500 Ningming County Industrial Park, Chongzuo, the Guangxi Zhuang Autonomous Region Patentee after: GUANGXI KEMAO FOREST CHEMICAL Co.,Ltd. Address before: 526238, Guangdong Zhaoqing hi tech Zone Yingbin Road, south side of the bridge side Patentee before: GUANGDONG KOMO Co.,Ltd. Patentee before: JIANGXI JIN'AN FOREST PRODUCTS INDUSTRIAL CO.,LTD. Patentee before: GUANGXI KEMAO FOREST CHEMICAL Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240109 Address after: 425300 No.1, north side of Industrial Avenue, Daoxian Industrial Park, Yongzhou City, Hunan Province Patentee after: HUNAN KOMO FOREST CHEMICAL CO.,LTD. Address before: 532500 Ningming County Industrial Park, Chongzuo, the Guangxi Zhuang Autonomous Region Patentee before: GUANGXI KEMAO FOREST CHEMICAL Co.,Ltd. |
|
TR01 | Transfer of patent right |