CN106243324B - 一种阻燃型环氧树脂及其制备方法 - Google Patents
一种阻燃型环氧树脂及其制备方法 Download PDFInfo
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- CN106243324B CN106243324B CN201610625854.8A CN201610625854A CN106243324B CN 106243324 B CN106243324 B CN 106243324B CN 201610625854 A CN201610625854 A CN 201610625854A CN 106243324 B CN106243324 B CN 106243324B
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- epoxy resin
- lignin
- fire
- preparation
- retardant epoxy
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 99
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 98
- 239000003063 flame retardant Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims description 28
- 229920005610 lignin Polymers 0.000 claims abstract description 90
- 238000012545 processing Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000009144 enzymatic modification Effects 0.000 claims abstract description 28
- 108090000790 Enzymes Proteins 0.000 claims abstract description 22
- 102000004190 Enzymes Human genes 0.000 claims abstract description 22
- 229940088598 enzyme Drugs 0.000 claims abstract description 22
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 13
- 108010059892 Cellulase Proteins 0.000 claims abstract description 11
- 108060008539 Transglutaminase Proteins 0.000 claims abstract description 11
- 229940106157 cellulase Drugs 0.000 claims abstract description 11
- 102000003601 transglutaminase Human genes 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 23
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 238000006735 epoxidation reaction Methods 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 238000005292 vacuum distillation Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- -1 polyoxyethylene Polymers 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 23
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 11
- 229920005989 resin Polymers 0.000 abstract description 7
- 239000011347 resin Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000012216 screening Methods 0.000 abstract description 2
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 15
- 150000002924 oxiranes Chemical group 0.000 description 12
- 239000012535 impurity Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 8
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 229910017053 inorganic salt Inorganic materials 0.000 description 5
- 229910002796 Si–Al Inorganic materials 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 3
- 239000010426 asphalt Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- VIRPUNZTLGQDDV-UHFFFAOYSA-N chloro propanoate Chemical compound CCC(=O)OCl VIRPUNZTLGQDDV-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Epoxy Resins (AREA)
Abstract
Description
编号 | 收率(%) | 环氧值(mol/100g) | 黏度(mPa.S) |
实施例1 | 98.9 | 0.42 | 36000 |
实施例2 | 98.8 | 0.41 | 37000 |
实施例3 | 99.1 | 0.45 | 41000 |
实施例4 | 99.0 | 0.43 | 40000 |
实施例5 | 99.0 | 0.43 | 39000 |
实施例6 | 99.4 | 0.47 | 43000 |
对比例1 | 75.5 | 0.23 | 19000 |
对比例2 | 80.1 | 0.27 | 20000 |
对比例3 | 70.2 | 0.21 | 17000 |
E-44环氧树脂 | 0.4 | 20000 |
编号 | Tg/℃ | 阻燃等级 | 是否熔滴 | LOI值/% |
实施例1 | 219 | UL94V-0 | 否 | 39.8 |
实施例2 | 220 | UL94V-0 | 否 | 40.1 |
实施例3 | 227 | UL94V-0 | 否 | 42.3 |
实施例4 | 223 | UL94V-0 | 否 | 39.7 |
实施例5 | 224 | UL94V-0 | 否 | 40.3 |
实施例6 | 236 | UL945-V | 否 | 44.5 |
对比例1 | 135 | 无级别 | 是 | 28.1 |
对比例2 | 141 | UL94V-2 | 否 | 33.4 |
对比例3 | 129 | 无级别 | 是 | 20.8 |
E-44环氧树脂 | 160 | UL94V-2 | 否 | 25.7 |
Claims (10)
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CN201610625854.8A CN106243324B (zh) | 2016-08-02 | 2016-08-02 | 一种阻燃型环氧树脂及其制备方法 |
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CN201610625854.8A CN106243324B (zh) | 2016-08-02 | 2016-08-02 | 一种阻燃型环氧树脂及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN106243324A CN106243324A (zh) | 2016-12-21 |
CN106243324B true CN106243324B (zh) | 2018-04-20 |
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CN201610625854.8A Active CN106243324B (zh) | 2016-08-02 | 2016-08-02 | 一种阻燃型环氧树脂及其制备方法 |
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CN (1) | CN106243324B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109796603A (zh) * | 2018-11-19 | 2019-05-24 | 青岛中科和源新材料有限公司 | 一种橡胶相溶剂及其制备方法 |
CN114350232A (zh) * | 2022-02-09 | 2022-04-15 | 上海正欧实业有限公司 | 一种阻燃环氧树脂地坪涂料及其制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100528926C (zh) * | 2006-10-21 | 2009-08-19 | 福州大学 | 酶解木质素环氧树脂的原料配方及其制备方法 |
CN101348558B (zh) * | 2008-09-12 | 2010-11-03 | 福州大学 | 一种酶解木质素环氧树脂及其制备方法 |
CN103524709B (zh) * | 2013-10-14 | 2016-05-11 | 南京林业大学 | 环氧树脂的制备方法 |
JP2016079328A (ja) * | 2014-10-20 | 2016-05-16 | ハリマ化成株式会社 | エポキシ樹脂およびエポキシ樹脂硬化剤 |
CN104892897A (zh) * | 2015-06-02 | 2015-09-09 | 安徽理工大学 | 利用木质素制备环氧树脂的方法 |
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