CN111116866A - Preparation method of high equivalent solvent type epoxy resin - Google Patents
Preparation method of high equivalent solvent type epoxy resin Download PDFInfo
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- CN111116866A CN111116866A CN201911407040.7A CN201911407040A CN111116866A CN 111116866 A CN111116866 A CN 111116866A CN 201911407040 A CN201911407040 A CN 201911407040A CN 111116866 A CN111116866 A CN 111116866A
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- CN
- China
- Prior art keywords
- epoxy resin
- solvent
- bisphenol
- parts
- catalyst
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- 239000002904 solvent Substances 0.000 title claims abstract description 30
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 18
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 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 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000003607 modifier Substances 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims abstract description 10
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000459 Nitrile rubber Polymers 0.000 claims abstract description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 8
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920001971 elastomer Polymers 0.000 claims abstract description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000000539 dimer Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical group CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims abstract description 4
- 239000001361 adipic acid Substances 0.000 claims abstract description 4
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 4
- 239000013557 residual solvent Substances 0.000 claims abstract description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000008096 xylene Substances 0.000 claims abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 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 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 3
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 claims 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- RZWDOHOQSSGFOR-UHFFFAOYSA-N bromo-ethyl-triphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(CC)C1=CC=CC=C1 RZWDOHOQSSGFOR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 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 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
The invention relates to a preparation method of high equivalent solvent type epoxy resin, which comprises the following raw materials, by weight, 100 parts of liquid epoxy resin, 50 parts of bisphenol A, 250 parts of solvent 220-one, 1-5 parts of modifier and 0.03-0.1 part of catalyst; the method comprises the following steps: (1) adding liquid epoxy resin, bisphenol A, a solvent and a modifier thereof into a four-neck flask, and completely dissolving the bisphenol A at the temperature of 110 ℃; (2) adding a catalyst at the temperature of 110 ℃, reacting for 6 hours, and adding the residual solvent to obtain the high equivalent solvent type epoxy resin product. The liquid epoxy resin is bisphenol A type glycidyl ether and bisphenol F glycidyl ether. The solvent is xylene, trimethylbenzene, methyl isobutyl ketone and the like, and the modifier is p-butyl phenol, dimer acid, mono-dimer acid, adipic acid, sebacic acid, carboxyl-terminated butadiene acrylonitrile rubber, amino-terminated butadiene acrylonitrile rubber and the like. The catalyst is sodium hydroxide, boron trifluoride, stannic chloride and the like. The product is mainly applied to the fields of coiled materials, tank coatings and the like.
Description
Technical Field
The invention relates to the field of epoxy resin, and in particular relates to a preparation method of high equivalent solvent type epoxy resin.
Background
High equivalent weight solvent-based epoxy resins are mainly used in the fields of coil materials, can coatings and the like, require high flexibility and machinability, and are particularly used for aluminum and iron beverage can lids, which are formed by punching and therefore need good flexibility and machinability. Currently, unmodified type 7 and type 9 epoxy resins are generally used, and cannot meet the processing requirements on can covers. Particularly, the processing requirements of the prior can are developed from a sheet coating process to a coil coating process, and the prior epoxy resin can not meet the processing requirements of a new process.
Disclosure of Invention
The invention aims to provide a preparation method of a high equivalent solvent type epoxy resin. The problem of the product processing performance that prior art exists is poor is solved.
The invention provides the following technical scheme:
a preparation method of a high equivalent solvent type epoxy resin comprises the following synthetic steps: the raw materials comprise, by weight, 100 parts of liquid epoxy resin, 50 parts of bisphenol A, 250 parts of solvent 220-5 parts of modifier and 0.03-0.1 part of catalyst;
(1) adding liquid epoxy resin, bisphenol A, a solvent and a modifier thereof into a four-neck flask, and completely dissolving the bisphenol A at the temperature of 110 ℃;
(2) adding a catalyst at the temperature of 110 ℃, reacting for several hours, and adding the residual solvent to obtain the high equivalent solvent type epoxy resin product.
The liquid epoxy resin is bisphenol A type glycidyl ether or bisphenol F glycidyl ether.
The solvent is one of dimethylbenzene, trimethylbenzene, methyl isobutyl ketone, ethylene glycol butyl ether, n-butyl alcohol, cyclohexanone and propylene glycol methyl ether acetate.
The modifier is one or a mixture of more than two of p-butyl phenol, dimer acid, mono-polyacid, adipic acid, sebacic acid, carboxyl-terminated butadiene acrylonitrile rubber and amino-terminated butadiene acrylonitrile rubber.
The catalyst is one of sodium hydroxide, boron trifluoride, stannic chloride, triphenyl ethyl phosphorus bromide, tetramethylammonium chloride, benzyltrimethylammonium chloride, ammonium hydroxide and 2 ethyl 4 methylimidazole.
The invention has the positive effects that: by embedding a flexible aliphatic long-chain structure in an epoxy resin structure and curing a phenolic resin, better flexibility and impact processing mechanical property of molecules can be provided so as to meet the application requirements of downstream customers. Compared with the existing high equivalent weight solvent type epoxy resin, after the flexible aliphatic long chain structure is embedded in the molecular weight and the phenolic resin is cured, the processing requirement of the coil coating process of the tank cover can be met, and the coating is free from abnormality after high-temperature sterilization and disinfection.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the specific embodiments of the present invention are not limited thereto.
In the following examples, the liquid epoxy resin is bisphenol a type glycidyl ether or bisphenol F glycidyl ether. The solvent is one of dimethylbenzene, trimethylbenzene, methyl isobutyl ketone, ethylene glycol butyl ether, n-butyl alcohol, cyclohexanone and propylene glycol methyl ether acetate. The modifier is one or a mixture of more than two of p-butyl phenol, dimer acid, mono-polyacid, adipic acid, sebacic acid, carboxyl-terminated butadiene acrylonitrile rubber and amino-terminated butadiene acrylonitrile rubber. The catalyst is one of sodium hydroxide, boron trifluoride, stannic chloride, triphenyl ethyl phosphorus bromide, tetramethylammonium chloride, benzyltrimethylammonium chloride, ammonium hydroxide and 2 ethyl 4 methylimidazole.
Example 1: 100g of bisphenol A epoxy resin YD-128, 50g of bisphenol A, 5g of modifier and 40g of solvent are added into a four-neck flask provided with a heating jacket, a stirrer and a condenser together to be heated to 110 ℃ to be fully dissolved, after the complete dissolution, a catalyst is added to be heated to 200 ℃ to react for 6 hours, and the rest 195g of solvent is added to obtain the final product.
Example 2: 100g of bisphenol F epoxy resin YDF-170, 50g of bisphenol A, 5g of modifier and 40g of solvent are added into a four-neck flask provided with a heating jacket and a condenser, the temperature is raised to 110 ℃ to completely dissolve the epoxy resin YDF-170, the modifier is added into the four-neck flask, the catalyst is added into the four-neck flask, the temperature is raised to 200 ℃ to react for 6 hours, and the residual solvent is added into the four-neck flask for 195g to obtain the final product.
Example 3: 100g of bisphenol A epoxy resin YD-128, 20g of bisphenol A and 5g of modifier are added into a four-neck flask provided with a heating jacket, a condenser is heated to 110 ℃ to be completely dissolved, a catalyst is added to the mixture, the temperature is raised to 170 ℃ to react for 2 hours, 30g of bisphenol A and 40g of solvent are added, the temperature of the catalyst is raised to 200 ℃ to react for 6 hours, and the rest solvent is added to 195g to obtain the final reaction product.
Example 4: 100g of bisphenol A epoxy resin YD-128 and 5g of modifier are added into a four-neck flask with a heating jacket, a condenser is heated to 110 ℃ and completely dissolved, then a catalyst is added, the temperature is raised to 170 ℃ for reaction for 2 hours, 50g of bisphenol A and 40g of solvent are added, the temperature of the catalyst is raised to 200 ℃ for reaction for 6 hours, and then the rest solvent is added to 195g to obtain the final reaction product.
Example 5: 100g of bisphenol A epoxy resin YD-128, 50g of bisphenol A and 5g of modifier are added into a four-neck flask provided with a heating jacket, a stirrer and a condenser together to be heated to 110 ℃ to be fully dissolved, after the complete dissolution, a catalyst is added to be heated to 200 ℃ to react for 6 hours, and 195g of solvent is added to obtain the final product.
Claims (5)
1. A preparation method of high equivalent solvent type epoxy resin comprises the following steps of taking 100 parts by weight of liquid epoxy resin, 50 parts by weight of bisphenol A, 250 parts by weight of solvent 220-5 parts by weight of modifier and 0.03-0.1 part by weight of catalyst as raw materials;
comprises the following synthetic steps:
(1) adding liquid epoxy resin, bisphenol A, a small part of solvent and a modifier thereof into a four-neck flask, and completely dissolving the bisphenol A at the temperature of 110 ℃;
(2) adding a catalyst at the temperature of 110 ℃, reacting for 6 hours, and adding the residual solvent to obtain the high equivalent solvent type epoxy resin product.
2. The method of claim 1, wherein the liquid epoxy resin is selected from the group consisting of bisphenol A glycidyl ether and bisphenol F glycidyl ether.
3. The preparation method of the solvent-type epoxy resin with high equivalent weight as claimed in claim 1, wherein the solvent is one of xylene, trimethylbenzene, methyl isobutyl ketone, ethylene glycol butyl ether, n-butanol, cyclohexanone and propylene glycol methyl ether acetate.
4. The method of claim 1, wherein the modifier is one or more of p-butyl phenol, dimer acid, adipic acid, sebacic acid, carboxyl-terminated butadiene acrylonitrile rubber, and amino-terminated butadiene acrylonitrile rubber.
5. The method of claim 1, wherein the catalyst is one of sodium hydroxide, boron trifluoride, tin tetrachloride, triphenyl ethyl phosphonium bromide, tetramethylammonium chloride, benzyltrimethylammonium chloride, ammonium hydroxide, and 2-ethyl-4-methylimidazole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911407040.7A CN111116866A (en) | 2019-12-31 | 2019-12-31 | Preparation method of high equivalent solvent type epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911407040.7A CN111116866A (en) | 2019-12-31 | 2019-12-31 | Preparation method of high equivalent solvent type epoxy resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111116866A true CN111116866A (en) | 2020-05-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911407040.7A Pending CN111116866A (en) | 2019-12-31 | 2019-12-31 | Preparation method of high equivalent solvent type epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111116866A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073701A (en) * | 2013-01-23 | 2013-05-01 | 宏昌电子材料股份有限公司 | Fatty acid modified epoxy resin and preparation method thereof |
| CN105017506A (en) * | 2015-07-21 | 2015-11-04 | 厦门双瑞船舶涂料有限公司 | Preparation method of modified epoxy resin |
| CN105985519A (en) * | 2016-05-31 | 2016-10-05 | 江山江环化学工业有限公司 | Synthesis method of phenoxy resin |
| CN107922588A (en) * | 2015-09-03 | 2018-04-17 | 三菱化学株式会社 | Epoxy resin, composition epoxy resin, solidfied material and electrical/electronic components |
-
2019
- 2019-12-31 CN CN201911407040.7A patent/CN111116866A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073701A (en) * | 2013-01-23 | 2013-05-01 | 宏昌电子材料股份有限公司 | Fatty acid modified epoxy resin and preparation method thereof |
| CN105017506A (en) * | 2015-07-21 | 2015-11-04 | 厦门双瑞船舶涂料有限公司 | Preparation method of modified epoxy resin |
| CN107922588A (en) * | 2015-09-03 | 2018-04-17 | 三菱化学株式会社 | Epoxy resin, composition epoxy resin, solidfied material and electrical/electronic components |
| CN105985519A (en) * | 2016-05-31 | 2016-10-05 | 江山江环化学工业有限公司 | Synthesis method of phenoxy resin |
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Address after: No. 16 Zijin Road, Circular Economy Park, Huizhou District, Huangshan City, Anhui Province Applicant after: Anhui Xinyuan Technology Co.,Ltd. Address before: No. 16 Zijin Road, Circular Economy Park, Huizhou District, Huangshan City, Anhui Province Applicant before: ANHUI XINYUAN CHEMICAL Co.,Ltd. |
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Application publication date: 20200508 |