CN106117540A - Epoxy curing agent and preparation method thereof, epoxy resin - Google Patents
Epoxy curing agent and preparation method thereof, epoxy resin Download PDFInfo
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- CN106117540A CN106117540A CN201610503713.9A CN201610503713A CN106117540A CN 106117540 A CN106117540 A CN 106117540A CN 201610503713 A CN201610503713 A CN 201610503713A CN 106117540 A CN106117540 A CN 106117540A
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- curing agent
- epoxy curing
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/54—Amino amides>
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/3331—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group cyclic
- C08G65/33313—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group cyclic aromatic
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
Abstract
The invention provides a kind of epoxy curing agent, it is characterised in that structural formula is:Wherein, PFPE is perfluoropolyether segment, containing CF in segment2CF2O—、—CF2CF(CF3)O—、—CF2O—、—CF(CF3)O—、—CF2CF2CF2O—、—C(CF3)2One or more repetitives in O, molecular weight is 300～10000, and R is aliphatic or aromatic divalent group, comprises the aliphatic group no less than two carbon, aromatic group.Compared with correlation technique, the present invention has the beneficial effects that, thermostability, weatherability, resistance to water, pliability, resistance to impact are good and environmental-protecting performance is strong.
Description
[technical field]
The present invention relates to firming agent technical field, particularly relate to a kind of epoxy curing agent and preparation method thereof, epoxy
Resin.
[background technology]
Amine curing agent is the epoxy curing agent that range is the widest, accounts for epoxy curing agent ratio
70%.The cured product of amine has a preferable performance, but has that volatility is big, toxicity big, poor water resistance, curing exotherm are violent
Etc. shortcoming.For overcoming disadvantage mentioned above, improving epoxy resin cured product performance, reply amine curing agent is modified, but changes at present
Property amine hardener still suffers from number of drawbacks.As polyether amine firming agent contains-CH2OCH2-structure, though pliability, impact resistance
Property is good, solidfied material water white transparency, but thermostability, weather resisteant are poor, easy xanthochromia.And introduce fluoroalkyl segment modified amine curing agent,
The thermostability of firming agent, weather resisteant, resistance to water can be improved, but be difficult to degrade more than the whole-fluoroalkyl chain segment of 8 carbon atoms, coating
Pliability is poor, and easily occurs being separated, and causes degradation under mechanical property, transparency.And less than the perfluoroalkyl chain of 8 carbon atoms
Though section degradable, the thermostability of solidfied material, weather resisteant, resistance to water are promoted inconspicuous.
Use fluoro-acrylate monomer common with ethylene oxidic ester/ether monomer as in China publication CN 104877111A
Poly-obtain fluorine-containing oxygen-containing random copolymer, then react with aliphatic polyamine and obtain random with fluoro-containing group and amino of side chain
Copolymer, i.e. modified fluoride-containing epoxy hardener.It is 84.3-98.4 degree with the water contact angle of this firming agent gained solidfied material, stretching
Intensity is 63.14-69.23MPa, and elongation at break is 7.3-10.7%, but owing to fluorinated volume is on the low side, hydrophobicity is the best.China
Open a kind of Flexible Curing Agents for Epoxy Resin and the synthetic method thereof of knowing clearly of publication CN104844784A, containing poly-in firming agent
Ether chain, the epoxy resin after solidification has certain pliability, but poor water resistance.Thus, the epoxy resin cure in correlation technique
There is thermostability, weatherability, resistance to water, pliability, resistance to impact is poor and environmental-protecting performance is relatively low deficiency in agent.
Therefore, it is necessary in fact to provide on a kind of new epoxy curing agent and preparation method thereof, epoxy resin overcomes
State technical problem.
[summary of the invention]
The technical issues that need to address of the present invention are to provide a kind of thermostability, weatherability, resistance to water, pliability, impact resistance
Property good and epoxy curing agent that environmental-protecting performance is strong.
One epoxy curing agent of the present invention, its structural formula is:
Wherein, PFPE is perfluoropolyether segment, containing CF in segment2CF2O—、—CF2CF(CF3)O—、—
CF2O—、—CF(CF3)O—、—CF2CF2CF2O—、—C(CF3)2One or more repetitives in O, molecular weight is
300～10000, R are aliphatic or aromatic divalent group, comprise the aliphatic group no less than two carbon, aromatic series base
Group.
Present invention also offers the preparation method of a kind of epoxy curing agent, it comprises the steps:
Step one, under inert gas shielding, by solvent, PFPE acyl fluorides, polyamine and solvent put into be provided with cold
In the reactor of solidifying reflux, react 2～24 hours in the environment of 20～80 DEG C；
Step 2, one or more the washing impurity used in methanol, ethanol, methyl acetate, butyl acetate, acetone, so
Detach solvent by vacuum rotary steam afterwards, then remove solid impurity by filtering；
Step 3, detach solvent by vacuum rotary steam, obtain described epoxy curing agent,
Wherein, described PFPE acyl fluorides is 1 (0.8～1.5) with the mol ratio of polyamine, the input amount of described solvent
For the twice of described PFPE acyl fluorides input amount or one times, in described methanol, ethanol, methyl acetate, butyl acetate, acetone
The usage amount of one or more is equal with the input amount of solvent.
Preferably, described solvent be methyl acetate, ethyl acetate, butyl acetate, acetone, butanone, a fluorine dichloroethanes,
Trifluorotrichloroethane, benzotrifluoride, two chlorobenzotrifluoride, tetrafluoro ethyl-methyl ether, tetrafluoro ethyl diethyldithiocarbamate ether, four fluoro ethyls third
The mixture of one or more in base ether, tetrafluoro ethyl-butyl ether, tetrafluoro ethylo benzene methyl ether.
Preferably, the one during described polyamine is ethylenediamine, p-phenylenediamine, diethylenetriamine.
Preferably, in step one, the response time in the environment of 20～80 DEG C is 6～8 hours.
Preferably, in step one, described noble gas is nitrogen.
Present invention also offers a kind of epoxy resin, it includes the component of following weight portion:
Epoxy curing agent 10～70 parts；
Bisphenol A epoxide resin 100 parts,
Wherein, the epoxide number of described bisphenol A epoxide resin is 0.10～0.56.
Compared with correlation technique, the beneficial effects of the present invention is, introduce perfluoropolyether segment modified amine curing agent, long
Chain PFPE can be greatly improved the thermostability of solidfied material, weather resisteant, color inhibition, resistance to water；In long-chain perfluoropolyether segment greatly
The introducing of amount flexible ether linkage, improves the pliability of firming agent molecule, and preferable with the compatibility of epoxy resin, is difficult to phase occur
Separate, make epoxy resin cured product have preferable pliability, resistance to impact；PFPE is biodegradable, does not have accumulation
Toxicity and zest, harmless with organism to environment, solve the environmental issue caused by long-chain perfluoroalkyl.Thus, heat-resisting
Property, weatherability, resistance to water, pliability, resistance to impact are more preferable and environmental-protecting performance is higher.
[detailed description of the invention]
For the ease of understanding the present invention, the present invention will be described more fully below.The present invention can with many not
Same form realizes, however it is not limited to embodiment described herein.On the contrary, providing the purpose of these embodiments is to make this
The understanding of disclosure of the invention content is more thorough comprehensively.
One epoxy curing agent of the present invention, its structural formula is:
Wherein, PFPE is perfluoropolyether segment, containing CF in segment2CF2O—、—CF2CF(CF3)O—、—
CF2O—、—CF(CF3)O—、—CF2CF2CF2O—、—C(CF3)2One or more repetitives in O, molecular weight is
300～10000, R are aliphatic or aromatic divalent group, comprise the aliphatic group no less than two carbon, aromatic series base
Group.
Present invention also offers the preparation method of a kind of epoxy curing agent, it comprises the steps:
Step one, under inert gas shielding, by solvent, PFPE acyl fluorides, polyamine and solvent put into be provided with cold
In the reactor of solidifying reflux, react 2～24 hours in the environment of 20～80 DEG C；
Step 2, one or more the washing impurity used in methanol, ethanol, methyl acetate, butyl acetate, acetone, so
Detach solvent by vacuum rotary steam afterwards, then remove solid impurity by filtering；
Step 3, detach solvent by vacuum rotary steam, obtain described epoxy curing agent,
Wherein, described PFPE acyl fluorides is 1 (0.8～1.5) with the mol ratio of polyamine, the input amount of described solvent
For the twice of described PFPE acyl fluorides input amount or one times, in described methanol, ethanol, methyl acetate, butyl acetate, acetone
The usage amount of one or more is equal with the input amount of solvent.
In present embodiment, more specifically, described solvent is methyl acetate, ethyl acetate, butyl acetate, acetone, first
Ethyl ketone, a fluorine dichloroethanes, trifluorotrichloroethane, benzotrifluoride, two chlorobenzotrifluoride, tetrafluoro ethyl-methyl ether, tetrafluoro second
The mixture of one or more in benzyl ethyl ether, tetrafluoro ethyl propyl ether, tetrafluoro ethyl-butyl ether, tetrafluoro ethylo benzene methyl ether.
In present embodiment, more specifically, during described polyamine is ethylenediamine, p-phenylenediamine, diethylenetriamine
Kind.
In present embodiment, more specifically, in step one, the response time in the environment of 20～80 DEG C is 6～8
Hour.
Present invention also offers a kind of epoxy resin, it includes the component of following weight portion: epoxy curing agent 10～
70 parts；Bisphenol A epoxide resin 100 parts, wherein, the epoxide number of described bisphenol A epoxide resin is 0.10～0.56.
Introduce perfluoropolyether segment modified amine curing agent, long-chain PFPE can be greatly improved solidfied material thermostability,
Weather resisteant, color inhibition, resistance to water；In long-chain perfluoropolyether segment, the introducing of a large amount of flexible ether linkage, improves firming agent molecule
Pliability, and preferable with the compatibility of epoxy resin, it is difficult to appearance and is separated, make epoxy resin cured product have the most pliable and the toughest
Property, resistance to impact；PFPE is biodegradable, does not have cumulative toxicity and zest, harmless with organism to environment, solves
Environmental issue caused by long-chain perfluoroalkyl.
It it is below specific embodiment.
Embodiment one:
500g benzotrifluoride is put into and is provided with in the reactor of condensation reflux unit, be then 3000 by 250g molecular weight
PFPE acyl fluorides is dissolved in benzotrifluoride under conditions of nitrogen is protected, and then drips 5g ethylenediamine under the protection of nitrogen,
Time for adding is 0.5 hour, reacts 6 hours at 25 DEG C.The methanol washing impurity of 500g is used after having reacted, then by subtracting
Pressure rotation steaming detaches solvent, then removes solid impurity by filtering, and detaches solvent finally by vacuum rotary steam, obtains water white transparency and glues
Shape liquid, is perfluoropolyether-modified epoxy curing agent.
The above-mentioned epoxy curing agents of 10 parts are mixed with 100 parts of bisphenol A epoxide resins that epoxide number is 0.51, room temperature
Epoxy resin is obtained after solidification 24h.Recording water contact angle 102 °, hexadecane contact angle 64 °, Tg point 180 DEG C, outside decocting in water 12h
Seeing unchanged, it is qualified that accelerated ageing Ageing machine QUV surveys 12h performance, tests the resistance to of coating by standard GB/T 22374-2008
Impact property, recording coating resistance to impact is II level.
Embodiment two:
250g tetrafluoro ethyl-butyl ether is put in the reactor being provided with condensation reflux unit, then by 250g molecular weight be
The PFPE acyl fluorides of 5000 is dissolved in tetrafluoro ethyl-butyl ether under conditions of nitrogen is protected, and then drips under the protection of nitrogen
Adding 3g p-phenylenediamine, time for adding is 0.5 hour, reacts 12 hours at 50 DEG C.The ethanol using 250g after having reacted is washed
Wash impurity, then detach solvent by vacuum rotary steam, then by filtering removal solid impurity, detach finally by vacuum rotary steam molten
Agent, obtains water white transparency and glues shape liquid, be perfluoropolyether-modified epoxy curing agent.
50 parts of above-mentioned firming agent are mixed, after normal temperature cure 24h with 100 parts of bisphenol A epoxide resins that epoxide number is 0.42
Obtain epoxy resin.Recording water contact angle 107 °, hexadecane contact angle 60 °, Tg point reaches 185 DEG C, and decocting in water 24h outward appearance is without becoming
Changing, it is qualified that accelerated ageing Ageing machine QUV surveys 24h performance, by the resistance to impact of standard GB/T 22374-2008 test coating
Can, recording coating resistance to impact is II level.
Embodiment three:
250g trifluorotrichloroethane is put in the reactor being provided with condensation reflux unit, be 3000 by 250g molecular weight
PFPE acyl fluorides is dissolved in trifluorotrichloroethane under conditions of nitrogen is protected, and then drips 5g diethyl under the protection of nitrogen
Alkene triamine, time for adding is 0.5 hour, reacts 24 hours under 50 DEG C of environment.The methanol using 250g after having reacted washs
Impurity, then detach solvent by vacuum rotary steam, then remove solid impurity by filtering, detach solvent finally by vacuum rotary steam,
Obtain water white transparency and glue shape liquid, be perfluoropolyether-modified epoxy curing agent.
70 parts of these firming agent are mixed with 100 parts of bisphenol A epoxide resins that epoxide number is 0.48, after normal temperature cure 24h
To epoxy resin.Recording water contact angle 105 °, hexadecane contact angle 65 °, Tg point reaches 175 DEG C, and decocting in water 24h outward appearance is without becoming
Changing, it is qualified that accelerated ageing Ageing machine QUV surveys 12h performance, by the resistance to impact of standard GB/T 22374-2008 test coating
Can, recording coating resistance to impact is II level.
Compared with correlation technique, the beneficial effects of the present invention is, thermostability, weatherability, resistance to water, pliability, resistance to punching
Hitting property is good and environmental-protecting performance is strong.
Above-described is only embodiments of the present invention, it should be noted here that for those of ordinary skill in the art
For, without departing from the concept of the premise of the invention, it is also possible to make improvement, but these belong to the protection model of the present invention
Enclose.
Claims (7)
1. an epoxy curing agent, it is characterised in that structural formula is:
Wherein, PFPE is perfluoropolyether segment, containing CF in segment2CF2O—、—CF2CF(CF3)O—、—CF2O—、—CF
(CF3)O—、—CF2CF2CF2O—、—C(CF3)2One or more repetitives in O, molecular weight is 300～10000, R
For aliphatic or aromatic divalent group, comprise the aliphatic group no less than two carbon, aromatic group.
2. the preparation method of an epoxy curing agent as claimed in claim 1, it is characterised in that comprise the steps:
Step one, under inert gas shielding, solvent, PFPE acyl fluorides, polyamine and solvent are put into and are provided with and condense back
In the reactor of stream device, react 2～24 hours in the environment of 20～80 DEG C；
Step 2, one or more the washing impurity used in methanol, ethanol, methyl acetate, butyl acetate, acetone, then lead to
Cross vacuum rotary steam and detach solvent, then remove solid impurity by filtering；
Step 3, detach solvent by vacuum rotary steam, obtain described epoxy curing agent,
Wherein, described PFPE acyl fluorides is 1 (0.8～1.5) with the mol ratio of polyamine, and the input amount of described solvent is institute
State the twice of PFPE acyl fluorides input amount or one times, the one in described methanol, ethanol, methyl acetate, butyl acetate, acetone
Or several usage amounts is equal with the input amount of solvent.
The preparation method of epoxy curing agent the most according to claim 2, it is characterised in that described solvent is tumer
Ester, ethyl acetate, butyl acetate, acetone, butanone, a fluorine dichloroethanes, trifluorotrichloroethane, benzotrifluoride, a dichloro three
Toluene fluoride, tetrafluoro ethyl-methyl ether, tetrafluoro ethyl diethyldithiocarbamate ether, tetrafluoro ethyl propyl ether, tetrafluoro ethyl-butyl ether, tetrafluoro ethylo benzene
The mixture of one or more in methyl ether.
The preparation method of epoxy curing agent the most according to claim 2, it is characterised in that described polyamine is second two
One in amine, p-phenylenediamine, diethylenetriamine.
The preparation method of epoxy curing agent the most according to claim 2, it is characterised in that in step one, 20
～the response time in the environment of 80 DEG C is 6～8 hours.
The preparation method of epoxy curing agent the most according to claim 2, it is characterised in that in step one, described lazy
Property gas is nitrogen.
7. an epoxy resin, it is characterised in that include the component of following weight portion:
Epoxy curing agent 10～70 parts；
Bisphenol A epoxide resin 100 parts,
Wherein, the epoxide number of described bisphenol A epoxide resin is 0.10～0.56.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610503713.9A CN106117540B (en) | 2016-06-30 | 2016-06-30 | Epoxy curing agent and preparation method thereof, epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610503713.9A CN106117540B (en) | 2016-06-30 | 2016-06-30 | Epoxy curing agent and preparation method thereof, epoxy resin |
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| Publication Number | Publication Date |
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| CN106117540A true CN106117540A (en) | 2016-11-16 |
| CN106117540B CN106117540B (en) | 2018-06-29 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107349871A (en) * | 2017-06-28 | 2017-11-17 | 龙岩思康特种化学品有限公司 | A kind of long-chain perfluoropolyether surfactants and preparation method thereof |
| CN111356714A (en) * | 2017-09-27 | 2020-06-30 | 阿科玛股份有限公司 | Addition and condensation polymers prepared from halogenated reactants |
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| CN101407620A (en) * | 2007-10-11 | 2009-04-15 | 同济大学 | High performance epoxy resins composite material and preparation thereof |
| CN101652404A (en) * | 2007-04-06 | 2010-02-17 | 优迈特株式会社 | Fluorinated polyether compound, process for producing the same, and curable composition containing the same |
| CN102061063A (en) * | 2010-12-10 | 2011-05-18 | 湖北省京珠高速公路管理处 | Epoxy resin injecting paste material for maintenance of road engineering and preparation method thereof |
| CN102151515A (en) * | 2011-03-11 | 2011-08-17 | 上海瀛正科技有限公司 | Amino acid type fluorocarbon surfactant, synthesis method and application |
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| CA2435924A1 (en) * | 2002-08-01 | 2004-02-01 | Solvay Solexis S.P.A. | Process for the preparation of perfluoropolyethers having aldehyde, alcohol, amine end groups by catalytic reduction |
| CN101652404A (en) * | 2007-04-06 | 2010-02-17 | 优迈特株式会社 | Fluorinated polyether compound, process for producing the same, and curable composition containing the same |
| CN101407620A (en) * | 2007-10-11 | 2009-04-15 | 同济大学 | High performance epoxy resins composite material and preparation thereof |
| CN102061063A (en) * | 2010-12-10 | 2011-05-18 | 湖北省京珠高速公路管理处 | Epoxy resin injecting paste material for maintenance of road engineering and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107349871A (en) * | 2017-06-28 | 2017-11-17 | 龙岩思康特种化学品有限公司 | A kind of long-chain perfluoropolyether surfactants and preparation method thereof |
| CN111356714A (en) * | 2017-09-27 | 2020-06-30 | 阿科玛股份有限公司 | Addition and condensation polymers prepared from halogenated reactants |
| US11525026B2 (en) | 2017-09-27 | 2022-12-13 | Arkerna Inc. | Addition and condensation polymers prepared from halogenated reactants |
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| CN106117540B (en) | 2018-06-29 |
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Effective date of registration: 20210701 Address after: No.203, jinhongyuan, 229 tongzipo West Road, Changsha hi tech Development Zone, Hunan Province, 410205 Patentee after: Hunan Tianfu New Materials Co.,Ltd. Address before: 230022 material building, East District, University of science and technology of China, 96 Jinzhai Road, Hefei City, Anhui Province Patentee before: Dong Qibao |
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