CN107083025B - A kind of preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system - Google Patents
A kind of preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system Download PDFInfo
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- CN107083025B CN107083025B CN201710433658.5A CN201710433658A CN107083025B CN 107083025 B CN107083025 B CN 107083025B CN 201710433658 A CN201710433658 A CN 201710433658A CN 107083025 B CN107083025 B CN 107083025B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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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
- 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
- C08G59/5026—Amines cycloaliphatic
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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
- 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
- C08G59/5033—Amines aromatic
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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
- 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
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
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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
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
Abstract
The present invention relates to a kind of preparation methods of carbon fiber Automobile Part rapid shaping fire resistant resin system, which solve existing resin system curing time is long, gel time under shaping efficiency is low and injection temperature is short, viscosity build is too fast, the technical problem poor to the wellability of fiber preform body, it includes the following steps: for high-active multiple amine and low activity aromatic amine to be stirred the curing agent component A to form stable homogeneous, anionic initiator and low molecule epoxide are heated, prepare modified anion type catalyst, catalytic component B is uniformly mixing to obtain with chain-transferring agent, the epoxy resin of different epoxide numbers is uniformly mixing to obtain resin Composition E, with curing agent component A, catalytic component B is uniformly mixed lower, prepare rapid shaping high-temperature-resistant epoxy resin system.The present invention can be used for the preparation field of carbon fiber Automobile Part.
Description
Technical field
The present invention relates to field of compound material, relate in particular to a kind of carbon fiber Automobile Part rapid shaping high temperature resistant tree
The preparation method of resin system.
Background technique
Carbon fibre composite will really be applied to the fields such as new-energy automobile, electronic apparatus, it is necessary to adapt to high yield certainly
The cost and speed of production that dynamic metaplasia produces, this proposes the scale, automation, rapid shaping technique of composite material higher
It is required that.RTM(Resin Transfer Molding, resin transfer molding) technique can realize semi-automatic or automatic metaplasia
It produces, becomes the developing direction of the following automobile-used CFRP moulding process by its advantage with short production cycle, and realize RTM and efficiently form
Key be exploitation fast-curing resin system and its matched curing process.
It is curing agent that fast-curing epoxy resin system, which mostly uses high-active multiple amine, at present, but the disadvantage is that resin system
Low viscosity plateau time is shorter, and fiber infiltration is not enough.
A kind of resin system of the International Patent Application Publication of Publication No. WO/2008/153542, uses high activity
Aliphatic cyclic amine makees curing agent, is prepared for RTM molding epoxy resin system, and longer working life meets large-scale composite material structural member
Technique requirement, but curing time is long, shaping efficiency is low.
A kind of resin system of the International Patent Application Publication of Publication No. WO/2015/014277, uses high activity rouge
Fat amine and Mannich modified firming agent, are prepared for quick-setting RTM molding epoxy resin system, and high solidification rate reduces multiple
Condensation material molding time, but gel time of the resin system under injection temperature is short, and viscosity build is too fast, to fiber preform
The wellability of body is poor.
Summary of the invention
The present invention is exactly to solve the gel under existing resin system curing time is long, shaping efficiency is low and injection temperature
The technical problem that time is short, viscosity build is too fast, poor to the wellability of fiber preform body provides a kind of while meeting quick
Solidify the preparation method of the high temperature resistant RTM epoxy-resin systems required with RTM moulding process.
For this purpose, the present invention provides a kind of preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system,
Include the following steps: that high-active multiple amine and low activity aromatic amine are stirred to form stable homogeneous by (1) at 60~90 DEG C
Curing agent component A, wherein the molar ratio of high-active multiple amine and low activity aromatic amine is 15:(1~5);(2) anion is drawn
Hair agent is heated to 70~100 DEG C with low molecule epoxide and reacts 3~6h, modified anion type catalyst is prepared, wherein living
The molar ratio for sprinkling hydrogen and epoxy group is 1:(0.8~1.3);Then catalytic component B is uniformly mixing to obtain with chain-transferring agent,
The molar ratio of middle modified anion type catalyst and chain-transferring agent is 1:(1~5);(3) epoxy resin of different epoxide numbers is existed
It is uniformly mixing to obtain resin Composition E in 40~70 DEG C of reaction kettle, is uniformly mixed with curing agent component A, catalytic component B, makes
Standby rapid shaping high-temperature-resistant epoxy resin system, wherein the mass ratio of component E, component A and component B are 100:(16~24): (3
~6);High-active multiple amine hardener is Meng's alkane diamines, isophorone diamine, diamino-dicyclohexyl methane, the bis- ammonia first of 1,3-
One of butylcyclohexane, N- aminoethyl piperazine, bis- (4- amino -3- methyl cyclohexyl) methane, fatty amines curing agent are several
The combination of kind;Low activity polyamine curing agent be diaminodiphenylsulfone, m-phenylene diamine (MPD), m-xylene diamine, diethyl toluene diamine,
One or more of combinations of diaminodiphenyl-methane;Tertiary amine anion initiator is 4-dimethylaminopyridine, imidazoles are solid
Agent and its derivative, N, N '-lupetazin, triethylamine, tripropyl amine (TPA), 2,4,6- tri- (dimethylamino methyl) phenol, three second
One or more of combinations of alkene diamines.
Preferably, low molecule epoxide is that n-butyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl are sweet
Oily ether, to the one or more of isobutyl glycidyl ether, diglycidyl ether.
Preferably, chain-transferring agent is glycerine, propylene glycol, ethylene glycol, butanediol, benzyl alcohol, diethylene glycol (DEG), phenol, ethyl
The one or more of phenol, ethyl mercaptan, small carboxylic acid molecules' class compound.
Preferably, epoxy resin-base is bisphenol A epoxide resin, bisphenol F epoxy resin, hydrogenated bisphenol A epoxy resin, contracting
The one or more of water glyceramine epoxy resin, ethylene oxidic ester epoxy resin, cycloaliphatic epoxy resin, novolac epoxy resin
Combination.
Effect of the present invention is, the resin system of this method preparation has longer working life, have at curing temperatures compared with
High reactivity, it can be achieved that in 5min rapid curing, significantly shorten molding cycle, can satisfy automotive field and quickly make
Make requirement of the technology to production efficiency, specific manifestation are as follows:
(1) with the epoxide number of blending epoxy regulation resin matrix, make resin system that there is good reactivity, together
When meet requirement of the RTM technique to low viscosity again, ensure that the good wellability of fiber preform, it is quick to be advantageously implemented RTM
Injection.
(2) the gradient solidification for causing resin with different activities polyamine curing agent, utilizes high-active multiple amine curing heat release
The curing reaction for causing low activity aromatic amine, improves curing efficiency, by solidification duration control within 5min, while aromatic amine
Introducing improve the heat resistance of resin.
(3) anionic initiator is modified with low molecule epoxide, reduces primary amine or secondary amine group low temperature
Lower reactivity improves the latent stability under low temperature, introduces chain-transferring agent and carries out chain tra nsfer to chain is caused, and realizes the two association
With catalysis, inhibit polymerization reaction early period, accelerates cured later.
Specific embodiment
More detailed description is done to the present invention below by way of specific embodiment: in embodiments, resin system curing degree
It is obtained by differential scanning calorimetry (DSC) test;Resin system mechanical property is tried by the universal material of U.S. Instron company
The machine of testing is tested to obtain;Resin stretched performance and bending property testing standard are according to GB/T 2567-2008;Glass transition temperature
It is obtained by dynamic thermomechanical analysis (DMA) test.
Embodiment 1
(1) isophorone diamine and diethyl toluene diamine are stirred to the curing agent to form stable homogeneous at 60 DEG C
Component, wherein isophorone diamine and the molar ratio of diethyl toluene diamine are 15:1.
(2) 2-methylimidazole is heated to 70 DEG C with n-butyl glycidyl ether and reacts 6h, prepared modified anion type and urge
Agent, wherein the molar ratio of active hydrogen and epoxy group is 1:0.8;The modified anion type catalyst and glycerine stirring is equal
Even to obtain catalytic component, wherein the molar ratio of modified anion type catalyst and chain-transferring agent is 1:1.
It (3) is in mass ratio the ratio of 6:4 in 40 DEG C of reaction kettle by bisphenol A type epoxy resin and novolac epoxy resin
It is uniformly mixing to obtain resin Composition, resin Composition, curing agent component, catalytic component are uniformly mixed, is prepared quick-setting
RTM resin system, wherein the mass ratio of resin Composition, curing agent component and catalytic component is 100:16:6, by what is prepared
Resin system constant temperature 5min in 120 DEG C of vacuum ovens, it is cooling, obtain resin-cast body.
The curing degree of resin system is 95%, and 80 DEG C of gel times are 11.5min, the glass transition temperature of resin-cast body
Degree is 148 DEG C, tensile strength 78MPa, stretch modulus 2800MPa, elongation at break 5.5%, and bending strength is
120MPa, bending modulus 2900MPa.
Embodiment 2
(1) isophorone diamine and 3,3- diaminodiphenylsulfone are stirred to the solidification to form stable homogeneous at 90 DEG C
Agent component, wherein the molar ratio of isophorone diamine and 3,3- diaminodiphenylsulfone is 15:5.
(2) 2-ethyl-4-methylimidazole and phenyl glycidyl ether are heated to 100 DEG C and react 4h, prepare modified yin from
Subtype catalyst, wherein the molar ratio of active hydrogen and epoxy group is 1:1.3.By the modified anion type catalyst and 1,4- fourth
Glycol is uniformly mixing to obtain catalytic component, and wherein the molar ratio of modified anion type catalyst and 1,4-butanediol is 1:5.
It (3) is in mass ratio reaction of the ratio of 7:3 at 70 DEG C by bisphenol A type epoxy resin and bisphenol f type epoxy resin
It is uniformly mixing to obtain resin Composition in kettle, resin Composition, curing agent component, catalytic component are uniformly mixed, prepares quickly solid
The RTM resin system of change, wherein the mass ratio of resin Composition, curing agent component and catalytic component is 100:24:3, will be prepared
Good resin system constant temperature 5min in 120 DEG C of vacuum drying ovens, cooling obtain resin-cast body.
The curing degree of resin system is 96%, and 80 DEG C of gel times are 12min, the glass transition temperature of resin-cast body
It is 150 DEG C, tensile strength 80MPa, stretch modulus 2850MPa, elongation at break 5.0%, bending strength 115MPa,
Bending modulus is 2950MPa.
Embodiment 3
(1) Meng's alkane diamines and m-phenylene diamine (MPD) are stirred to the curing agent component to form stable homogeneous at 70 DEG C, wherein
The molar ratio of Meng's alkane diamines and m-phenylene diamine (MPD) is 15:3.
(2) 2-methylimidazole is heated to 80 DEG C with allyl glycidyl ether and reacts 5h, prepared modified anion type and urge
Agent, wherein the molar ratio of active hydrogen and epoxy group is 1:1.The modified anion type catalyst is stirred evenly with butanediol
Obtained catalytic component, wherein the molar ratio of modified anion type catalyst and butanediol is 1:3.
(3) ratio that bisphenol A type epoxy resin and three-functionality-degree ethylene oxidic ester epoxy resin are 7:3 in mass ratio is existed
It is uniformly mixing to obtain resin Composition in 60 DEG C of reaction kettle, resin Composition, curing agent component, catalytic component are uniformly mixed,
Quick-setting RTM resin system is prepared, wherein the mass ratio of resin Composition, curing agent component and catalytic component is 100:
20:4, by the resin system prepared, constant temperature 5min, cooling obtain resin-cast body in 120 DEG C of vacuum ovens.
The curing degree of resin system is 95%, and 80 DEG C of gel times are 12min, and the glass transition temperature of resin is 142
DEG C, tensile strength 80MPa, stretch modulus 2800MPa, elongation at break 5.2%, bending strength 112MPa, bending die
Amount is 2900MPa.
Comparative example 1
For the resin system in addition to not having to add chain-transferring agent group exceptionally, other resin Compositions are identical with embodiment 1.
(1) isophorone diamine and diethyl toluene diamine are stirred to the curing agent to form stable homogeneous at 60 DEG C
Component, wherein isophorone diamine and the molar ratio of diethyl toluene diamine are 15:1.
(2) 2-methylimidazole is heated to 70 DEG C with n-butyl glycidyl ether and reacts 6h, prepared modified anion type and urge
Agent, wherein the molar ratio of active hydrogen and epoxy group is 1:0.8.
It (3) is in mass ratio the ratio of 6:4 in 40 DEG C of reaction kettle by bisphenol A type epoxy resin and novolac epoxy resin
It is uniformly mixing to obtain resin Composition, resin Composition, curing agent component, catalytic component are uniformly mixed, is prepared quick-setting
RTM resin system, wherein resin Composition, curing agent component, catalytic component mass ratio be 100:16:3, the tree that will be prepared
Resin system constant temperature 5min in 120 DEG C of vacuum ovens, it is cooling, obtain resin-cast body.
The curing degree of resin system is 85%, and 80 DEG C of gel times are 11min, the glass transition temperature of resin-cast body
It is 135 DEG C, tensile strength 70MPa, stretch modulus 2700MPa, elongation at break 4.8%, bending strength 108MPa,
Bending modulus is 2800MPa.
Comparative example 2
For the resin system other than not adding fragrant amine component, other resin Compositions are identical with embodiment 2.
(1) 2-ethyl-4-methylimidazole and phenyl glycidyl ether are heated to 100 DEG C and react 4h, prepare modified yin from
Subtype catalyst, wherein the molar ratio of active hydrogen and epoxy group is 1:1.3.By the latency anionic catalyst and 1,4- fourth
Glycol is uniformly mixing to obtain catalytic component, and wherein the molar ratio of modified anion type catalyst and 1,4-butanediol is 1:5.
It (2) is in mass ratio reaction of the ratio of 7:3 at 50 DEG C by bisphenol A type epoxy resin and bisphenol f type epoxy resin
It is uniformly mixing to obtain resin Composition in kettle, resin Composition, isophorone diamine, catalytic component are uniformly mixed, preparation is quick
Cured RTM resin system, wherein resin Composition, isophorone diamine, catalytic component mass ratio be 100:21:3, will make
The resin system got ready constant temperature 5min in 120 DEG C of vacuum drying ovens, it is cooling, obtain resin-cast body.
The curing degree of resin system is 90%, and 80 DEG C of gel times are 11.5min, the glass transition temperature of resin-cast body
Degree is 140 DEG C, tensile strength 70MPa, stretch modulus 2750MPa, elongation at break 4.5%, and bending strength is
105MPa, bending modulus 2800MPa.
As can be seen from the above Examples and Comparative Examples, it effect of the invention is that shortening the curing time of resin, mentions
High shaping efficiency, and working life of the resin under injection temperature is extended, be conducive to the infiltration to fiber preform body.
Claims (4)
1. a kind of preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system, it is characterized in that including following step
It is rapid: high-active multiple amine and low activity aromatic amine (1) are stirred to the curing agent group to form stable homogeneous at 60~90 DEG C
Divide A, wherein the molar ratio of high-active multiple amine and low activity aromatic amine is 15:(1~5);(2) by anionic initiator and low point
Subring oxygen compound is heated to 70~100 DEG C of 3~6h of reaction, prepares modified anion type catalyst, wherein active hydrogen and epoxy
The molar ratio of group is 1:(0.8~1.3);Then catalytic component B is uniformly mixing to obtain with chain-transferring agent, wherein modified yin from
The molar ratio of subtype catalyst and chain-transferring agent is 1:(1~5);(3) by the epoxy resin of different epoxide numbers at 40~70 DEG C
It is uniformly mixing to obtain resin Composition E in reaction kettle, is uniformly mixed with curing agent component A, catalytic component B, prepares rapid shaping
High-temperature-resistant epoxy resin system, wherein the mass ratio of component E, component A and component B are 100:(16~24): (3~6);The height
Active polyamine is Meng's alkane diamines, isophorone diamine, diamino-dicyclohexyl methane, the bis- aminomethyl cyclohexanes of 1,3-, N- ammonia
The combination of one or more of ethyl piperazidine, bis- (4- amino -3- methyl cyclohexyl) methane, fatty amines curing agent;It is described
Low activity aromatic amine is diaminodiphenylsulfone, m-phenylene diamine (MPD), m-xylene diamine, diethyl toluene diamine, diamino-diphenyl first
One or more of combinations of alkane;The anionic initiator be 4-dimethylaminopyridine, imidazole curing agent and its derivative,
N, N '-lupetazin, triethylamine, tripropyl amine (TPA), 2,4,6- tri- (dimethylamino methyl) phenol, triethylene diamine one kind or
Several combinations.
2. the preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system according to claim 1, special
Sign is: the low molecule epoxide is n-butyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl
Ether, to the one or more of isobutyl glycidyl ether, diglycidyl ether.
3. the preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system according to claim 1, special
Sign is: the chain-transferring agent is glycerine, propylene glycol, ethylene glycol, butanediol, benzyl alcohol, diethylene glycol (DEG), phenol, ethylo benzene
The one or more of phenol, ethyl mercaptan, small carboxylic acid molecules' class compound.
4. the preparation method of carbon fiber Automobile Part rapid shaping fire resistant resin system according to claim 1, special
Sign is: the epoxy resin-base is bisphenol A epoxide resin, bisphenol F epoxy resin, hydrogenated bisphenol A epoxy resin, shrink
One or more of groups of glyceramine epoxy resin, ethylene oxidic ester epoxy resin, cycloaliphatic epoxy resin, novolac epoxy resin
It closes.
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