CN106987013A - The preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature is improved - Google Patents
The preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature is improved Download PDFInfo
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- CN106987013A CN106987013A CN201710346121.5A CN201710346121A CN106987013A CN 106987013 A CN106987013 A CN 106987013A CN 201710346121 A CN201710346121 A CN 201710346121A CN 106987013 A CN106987013 A CN 106987013A
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- prepreg
- epoxy
- temperature setting
- preparation
- glass transition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
Abstract
A kind of preparation method of the intermediate temperature setting epoxy prepreg improved the present invention relates to glass transition temperature, which solve the technical problem that general intermediate temperature setting prepreg heat resistance is contradicted with toughness and manufacturability, it is under catalyst action, isocyanates and epoxy resin are reacted, prepare modified epoxy, into modified epoxy, add liquid epoxies and curing system, prepare prepreg resin system, obtained prepreg is used into adhesive film machine film with resin system, then it is compound via compounding machine and reinforcing fiber or fabric, prepare intermediate temperature setting prepreg.The present invention can be used for the preparation field of prepreg.
Description
Technical field
The invention belongs to high performance resin based composites field, relate in particular in a kind of glass transition temperature raising
The preparation method of warm cured epoxy resin prepreg.
Background technology
Carbon fibre composite because the features such as its light weight is high-strength, performance can be designed and moulding process is various, extensively should
For in advanced composite material, based on the harshness of the leading-edge field such as Aero-Space use condition, general epoxy resin-matrix is combined
Not only fragility is big for material, and is difficult to meet its high temperature resistant demand.
It is general to improve heat resistance and tough sexual approach：One is to be consolidated using high performance polyfunctional group resin with resistant to elevated temperatures toughness
Agent, the higher cost of material of this method and solidification temperature so that the manufacturing cost of composite is greatly increased；Two be to coordinate resistance to
The thermoplastic resin of hot and tenacity excellent, although toughness of material is improved, it is very small on rigidity and heat resistance influence, but cause
Resin system viscosity steeply rises, and prepreg processing characteristics deteriorates.
Publication No. CN 102165010A Chinese invention patent application discloses a based epoxy resin composition, preimpregnation
Material base and fibre reinforced composites, the invention realize the high resistance to of composite by adding a kind of control block copolymer
Heat and high tenacity, but resin system viscosity steeply rises, and prepeg process is deteriorated；And solidification temperature is higher.
The B2 of United States Patent (USP) US 7883766 disclose a class prepreg and its resin combination, and the invention is first with heat
Plastic polyamide resin prepares performed polymer with phenol compound under 180 DEG C of high temperature, is then added to containing many officials of high temperature resistant
In the resin system that epoxy can be rolled into a ball, glass transition temperature has been obtained more than 150 DEG C, toughness and the excellent composite wood of impact resistance
Material, but the process is complex, the addition of high temperature prepolymerization reaction and multifunction group epoxy, makes production cost high, no
Beneficial to promoting the use of.
The content of the invention
The present invention is exactly to solve the skill that general intermediate temperature setting prepreg heat resistance is contradicted with toughness and manufacturability
Art problem, by designing the modification route of cost degradation, is modified using isocyanates to general purpose epoxy resin, Bei Gao Evil processed
The high temperature toughened epoxy resin of oxazolidone content, applied in prepreg resin system, obtains a kind of heat resistance, toughness and work
The preparation method for the intermediate temperature setting epoxy prepreg that the excellent inexpensive glass transition temperature of skill is improved.
Therefore, the present invention comprises the following steps：(1) under catalyst action, isocyanates and epoxy resin are pressed 1:(5
~mol ratio 2) reacts 3~6h in modified epoxy at 150~180 DEG C, prepares modified epoxy, relative to isocyanates with
100 parts of epoxy resin quality sum, the mass fraction of catalyst is 0.1~1.0 part；In described modified epoxy reaction, in real time
Infrared spectroscopy monitor oxazolidone rings conversion ratio is 100%；(2) in the modified epoxy obtained into the step (1),
Liquid epoxies and curing system are added, prepreg resin system is prepared, wherein relative to 100 parts modified epoxies,
The mass fraction of liquid epoxies is 35~65 parts, and the mass fraction of curing system is 10~15 parts；(3) by the step
(2) prepreg obtained uses adhesive film machine film with resin system, then compound via compounding machine and reinforcing fiber or fabric, system
Standby intermediate temperature setting prepreg.
It is preferred that, isocyanates is methyl diphenylene diisocyanate (MDI), toluene di-isocyanate(TDI) (TDI), different Fo Er
One or more in ketone diisocyanate (IPDI), hexamethylene diisocyanate (HDI).
It is preferred that, it is bisphenol-type epoxy resin, novolac epoxy resin, orthoresol ring with the epoxy resin that isocyanates reacts
Oxygen tree fat, bisphenol-A phenolic epoxy resin, the one or more of bisphenol-s epoxy resin.
It is preferred that, catalyst is imidazoles, imdazole derivatives, tertiary ammonium salt, quaternary ammonium salt, quaternary alkylphosphonium salt, metal halide, metal have
One or more in machine compound.Above-mentioned catalytic agent also includes lewis acid and alkali complex compound, and its with Above-mentioned catalytic agent
Combination.
It is preferred that, liquid epoxies is bis-phenol A glycidyl ether, Bisphenol F glycidol ether, bisphenol-A D-ring oxygen tree
The one or more of fat, cycloaliphatic epoxy resin.
It is preferred that, curing system is one kind or several in dicyandiamide, modified dicyandiamine, carbamide derivative, imdazole derivatives
Kind.
It is preferred that, reinforcing fiber or fabric are glass fibre, carbon fiber, aramid fiber, basalt fibre, polyamide fibre
One or more in dimension, polyester fiber, acrylic fiber, string.
It is preferred that, the solidification temperature of intermediate temperature setting prepreg is 130~150 DEG C.
The beneficial effects of the present invention are：First, compared with general purpose epoxy resin, five yuan of the rigidity of Gao Han Liang oxazolidones
The introducing of ring structure, improves the glass transition temperature of solidfied material, while strong pole property oxazolidone ring increases in intrinsic structure
The caking property of fiber and resin is added；Secondly, by reasonably controlling raw material proportioning and modified technique route, make isocyanates complete
Portion's Zhuanization Wei oxazolidone ring structure , oxazolidone ring conversion ratios are 100%, the linear chain extender as general purpose epoxy resin,
So as to increase the distance in solidfied material cross-linked network between rigid crosslinking points, the toughness of resin is improved well；Moreover, general ring
Oxygen tree fat considerably increases the molecular mass and viscosity of modified resin, is conducive to carrying for resin system viscosity after chain extending reaction
The high extension with high temperature viscosity platform area, effectively prevent the gummosis of prepreg resin system.Therefore, prepreg tree of the invention
Resin system preparation technology rationally, while guarantee prepreg excellent manufacturability and caking property, significantly improves composite wood
The heat resistance and toughness of material.
Embodiment
OX conversion ratios in the present invention：Refer to reaction end, the hundred of isocyano (- NCO) Zhuanization Wei oxazolidones ring (OX rings)
Divide ratio, detected using REAL TIME INFRARED THERMAL IMAGE, according to the infrared peak integral area of OX rings is converted into, account for OX rings and isocyanurate ring (IS rings)
The percentage of corresponding infrared peak integral area sum is calculated；Solidified resin and the glass transition temperature of composite in the present invention
(Tg) tested using DMTA methods；The viscosity of modified epoxy and resin system is surveyed using standard GB/T22314-2008 in the present invention
Examination.
Embodiment of the present invention is further illustrated with embodiment below, but the invention is not restricted to following examples.
Embodiment 1
By MDI under imidazoles catalyst action with bisphenol-A phenolic epoxy resin according to mol ratio 1:5 in anti-at 150 DEG C
6h is answered to prepare modified epoxy, relative to 100 parts of the two quality sum, the mass fraction of imidazoles catalyst is 0.1 part.Take
Above-mentioned 100 parts of modified epoxy (mass fraction, similarly hereinafter), adds 25 parts of liquid bis-phenol A glycidyl ether respectively and liquid is double
10 parts of phenol F glycidyl ether mixtures, add 10 parts of modified dicyandiamine curing agent, prepare middle temperature epoxy resin for prepreg
System.Above-mentioned resin system is prepared into glued membrane using adhesive film machine, preimpregnation is prepared via compounding machine and reinforcing fiber or fabric are compound
Material, then solidifies 2h respectively at 150 DEG C by resin system and prepreg and prepares pour mass batten and composite board.
Embodiment 2
TDI is pressed under triphenyl phosphorus catalyst action with bisphenol A type epoxy resin and o-cresol epoxy resin mixture
According to mol ratio 1:2:1.5, modified epoxy is prepared in reacting 4.5h at 165 DEG C, relative to TDI and epoxy resin quality sum 100
Part, the mass fraction of triphenyl phosphorus is 0.5 part.Above-mentioned 100 parts of modified epoxy is taken, 50 parts of liquid bisphenol-A water glycerin ether is added, then
The dicy-curing agent of 12.5 parts of addition, prepares middle temperature epoxy resin for prepreg system.Above-mentioned resin system is used into glued membrane
Machine prepares glued membrane, prepreg is prepared via compounding machine and reinforcing fiber or fabric are compound, then by resin system and prepreg point
Do not solidify 3h in 140 DEG C and prepare pour mass batten and composite board.
Embodiment 3
MDI is pressed under imidazoles catalyst action with bisphenol-A phenolic epoxy resin and bisphenol-s epoxy resin mixture
According to mol ratio 1:1:1, modified epoxy is prepared in reacting 3h at 180 DEG C, relative to 100 parts of MDI and epoxy resin quality sum, miaow
The mass fraction of azole catalyst is 1.0 parts.Above-mentioned 100 parts of modified epoxy is taken, 65 parts of liquid bis-phenol A glycidyl ether is added,
Add 14 parts dicy-curing agent and 1 part of carbamide derivative accelerator, prepare middle temperature epoxy resin for prepreg system.Will
Above-mentioned resin system prepares glued membrane using adhesive film machine, prepares prepreg via compounding machine and reinforcing fiber or fabric are compound, then
Resin system and prepreg are solidified into 4.5h respectively at 130 DEG C and prepare pour mass batten and composite board.
Comparative example 1
Take 100 parts of bisphenol-A phenolic epoxy resin to be placed in reactor, 25 parts of liquid bis-phenol A glycidyl ether is added respectively
With 10 parts of liquid bisphenol F glycidyl ether mixtures, 10 parts of modified dicyandiamine curing agent is added, middle temperature prepreg is prepared and uses
Epoxy-resin systems.Above-mentioned resin system is prepared into glued membrane using adhesive film machine, it is compound via compounding machine and reinforcing fiber or fabric
Prepreg is prepared, resin system and prepreg then are solidified into 2h respectively at 150 DEG C prepares pour mass batten and composite panel
Material.
The physical properties of the resin system of table 1 and composite
Claims (8)
1. the preparation method for the intermediate temperature setting epoxy prepreg that a kind of glass transition temperature is improved, it is characterized in that including following step
Suddenly：
(1) under catalyst action, isocyanates and epoxy resin are pressed 1:The mol ratio of (5~2) changes at 150~180 DEG C
Property 3~6h of epoxy reaction, prepares modified epoxy, relative to 100 parts of isocyanates and epoxy resin quality sum, catalyst
Mass fraction be 0.1~1.0 part；Described modified epoxy reaction Zhong , oxazolidone rings conversion ratio is 100%；
(2) in the modified epoxy obtained into the step (1), liquid epoxies and curing system are added, is prepared pre-
Material resin system is soaked, wherein relative to 100 parts modified epoxies, the mass fraction of liquid epoxies is 35~65 parts,
The mass fraction of curing system is 10~15 parts；
(3) prepreg for obtaining the step (2) uses adhesive film machine film with resin system, then via compounding machine and enhancing
Fiber or fabric are compound, prepare intermediate temperature setting prepreg.
2. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate
One or more in ester, hexamethylene diisocyanate.
3. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described is bisphenol-type epoxy resin, novolac epoxy resin, orthoresol ring with the epoxy resin that isocyanates reacts
Oxygen tree fat, bisphenol-A phenolic epoxy resin, the one or more of bisphenol-s epoxy resin.
4. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described catalyst is imidazoles, imdazole derivatives, tertiary ammonium salt, quaternary ammonium salt, quaternary alkylphosphonium salt, metal halide, metal have
One or more in machine compound, lewis acid and alkali complex compound.
5. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described liquid epoxies be bis-phenol A glycidyl ether, Bisphenol F glycidol ether in, bisphenol-A D-ring oxygen tree
The one or more of fat, cycloaliphatic epoxy resin.
6. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described curing system is one kind or several in dicyandiamide, modified dicyandiamine, carbamide derivative, imdazole derivatives
Kind.
7. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：Described reinforcing fiber or fabric are glass fibre, carbon fiber, aramid fiber, basalt fibre, polyamide fibre
One or more in dimension, polyester fiber, acrylic fiber, string.
8. the preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature according to claim 1 is improved, its
It is characterised by：The solidification temperature of described intermediate temperature setting prepreg is 130~150 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201710346121.5A CN106987013A (en) | 2017-05-17 | 2017-05-17 | The preparation method for the intermediate temperature setting epoxy prepreg that glass transition temperature is improved |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107325292A (en) * | 2017-09-01 | 2017-11-07 | 江苏欧亚铂瑞碳复合材料有限公司 | A kind of method of modifying of cyanate ester resin |
| CN107674222A (en) * | 2017-11-02 | 2018-02-09 | 北京化工大学 | A kind of aramid fiber composite material preparation method of interfacial adhesion enhancing |
| CN108858883A (en) * | 2018-05-30 | 2018-11-23 | 江苏兆鋆新材料股份有限公司 | A kind of method that phenoxy resin prepreg and hot melt prepare the phenoxy resin prepreg |
| CN110527255A (en) * | 2019-09-09 | 2019-12-03 | 东莞泰合复合材料有限公司 | A kind of epoxy resin-base, composite material, vehicle frame and preparation method thereof |
| CN111004408A (en) * | 2019-12-23 | 2020-04-14 | 江苏恒神股份有限公司 | Preparation method of white-point-free fast-curing epoxy prepreg |
| CN111440420A (en) * | 2020-05-08 | 2020-07-24 | 江苏扬农锦湖化工有限公司 | Preparation method of high-performance epoxy toughening material |
| CN112375242A (en) * | 2020-11-03 | 2021-02-19 | 北京化工大学常州先进材料研究院 | Preparation method of quickly-formed ultrathin flame-retardant composite material plate |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107325292A (en) * | 2017-09-01 | 2017-11-07 | 江苏欧亚铂瑞碳复合材料有限公司 | A kind of method of modifying of cyanate ester resin |
| CN107674222A (en) * | 2017-11-02 | 2018-02-09 | 北京化工大学 | A kind of aramid fiber composite material preparation method of interfacial adhesion enhancing |
| CN108858883A (en) * | 2018-05-30 | 2018-11-23 | 江苏兆鋆新材料股份有限公司 | A kind of method that phenoxy resin prepreg and hot melt prepare the phenoxy resin prepreg |
| CN110527255A (en) * | 2019-09-09 | 2019-12-03 | 东莞泰合复合材料有限公司 | A kind of epoxy resin-base, composite material, vehicle frame and preparation method thereof |
| CN111004408A (en) * | 2019-12-23 | 2020-04-14 | 江苏恒神股份有限公司 | Preparation method of white-point-free fast-curing epoxy prepreg |
| CN111440420A (en) * | 2020-05-08 | 2020-07-24 | 江苏扬农锦湖化工有限公司 | Preparation method of high-performance epoxy toughening material |
| CN111440420B (en) * | 2020-05-08 | 2023-04-11 | 江苏扬农锦湖化工有限公司 | Preparation method of high-performance epoxy toughening material |
| CN112375242A (en) * | 2020-11-03 | 2021-02-19 | 北京化工大学常州先进材料研究院 | Preparation method of quickly-formed ultrathin flame-retardant composite material plate |
| CN112375242B (en) * | 2020-11-03 | 2022-03-22 | 北京化工大学常州先进材料研究院 | Preparation method of quickly-formed ultrathin flame-retardant composite material plate |
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