CN108752878A - A kind of fibre reinforced thermoplastic polyester - Google Patents
A kind of fibre reinforced thermoplastic polyester Download PDFInfo
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- CN108752878A CN108752878A CN201810590891.9A CN201810590891A CN108752878A CN 108752878 A CN108752878 A CN 108752878A CN 201810590891 A CN201810590891 A CN 201810590891A CN 108752878 A CN108752878 A CN 108752878A
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- carbon fiber
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- thermoplastic polyester
- short fine
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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
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Abstract
The present invention relates to a kind of fiber reinforced thermolplastic polyester, the short fine strengthened thermoplastic polyester of especially a kind of carbon fiber, including following components：100 parts by weight of polyethylene naphthalate；Short fine 10~100 parts by weight of carbon fiber；0.1~5 parts by weight of epoxide；Wherein, the short fine average length of the carbon fiber is 1~5mm, and the short fibre of carbon fiber is surface-modified, and surface has at least one layer of polycarbodiimide layer and at least one layer of polymeric layer containing carboxylic acid functional.The present invention also provides a kind of preparation methods of fiber reinforced thermolplastic polyester simultaneously, by improving the compatibility of carbon fiber and polyethylene naphthalate, to improve the performance of the short fine strengthened thermoplastic polyester composite material of carbon fiber.
Description
Technical field
The present invention relates to a kind of fiber reinforced thermolplastic polyester, the short fine strengthened thermoplastic polyester of especially a kind of carbon fiber.
Background technology
Carbon fiber (CF) is a kind of novel metalloid material, has big intensity height, scale, endurance and creep-resistant property high
Equal excellent performances.
Carbon fiber enhancement resin base composite material (CFRP) has the superiority such as high ratio modulus, high specific strength and low-density
Energy.The performance of composite material depends not only on its component material, while also heavily depending on interface between each component, compound
The interface of material is the interphase of reinforced phase and matrix phase, is bridge and stress, heat that reinforced phase is connected with matrix
Transmitter, good interface bonding energy effectively transmit load and heat, improve the thermal conductivity and its mechanical property of composite material.
But carbon fiber surface inertia is big, and surface energy is low, lacks active function groups, reactivity is low, the bad adhesion with matrix, in interface
There are more defects, this directly affects the performance of composite material, hinder its further application.
Patent CN201010614830.5 provides a kind of carbon-fiber-reinforced polyester composite material, is by polyester, carbon fiber
With additive injection molding be prepared, used in carbon fiber surface by liquid polypropylene nitrile oligomer pre-oxidize and adsorption
Active itrile group improves the mechanical strength of composite material, but effect is still unsatisfactory to improve the caking property with polyester matrix.
Invention content
The present invention provides a kind of short fine strengthened thermoplastic polyesters of carbon fiber, including following components：
100 parts by weight of polyethylene naphthalate；
Short fine 10~100 parts by weight of carbon fiber；
0.1~5 parts by weight of epoxide；
Wherein, 1~5mm of the short fine average length of the carbon fiber, and the short fibre of carbon fiber is surface-modified, surface tool
There are at least one layer of polycarbodiimide layer and at least one layer of polymeric layer containing carboxylic acid functional.
Polyethylene naphthalate (PEN) is by 2,6- naphthalene diformic acid dimethyl esters (NDC) or 2,6- naphthalenedicarboxylic acids (NDA)
It is formed with ethylene glycol (EG) polycondensation, there is preferably than polyethylene terephthalate (PET) mechanical performance, barrier properties for gases
Can, the performances such as chemical stability and heat-resisting, UV resistant, radiation hardness.
The short fibre of carbon fiber is that two dimension or three-dimensional fiber material made of being woven with carbon fiber are formed by cutting machine is chopped, is put down
Equal length is generally 1~5mm.The short fibre of carbon fiber is added in PEN can significantly improve mechanical strength (such as tensile strength of PEN
And bending strength).Content preferably 30~80 parts by weight can provide the enough mechanical strengths of material and thermal conductivity without influencing other
Property.
Due to the chemical inertness of carbon fiber, and the compatibility of organic matrix resin is weak, interfacial adhesion is indifferent, needs to lead to
It crosses surface to be modified to improve matrix resin in the effect of impregnation of carbon fiber surface, reduces the defect inside carbon fibre composite,
Improve the mechanical strength of material.It refers to being improved by manufacturing process such as oxidation, coating, grafting on the surface of carbon fiber that surface, which is modified,
The compatibility and caking property of the chemical substances such as carbon fiber and polyester resin, improve the mechanical performance of composite material.Specific such as strong oxygen
Agent oxidation, grafting organic matter etc..The present invention has at least one layer of polycarbodiimide layer and at least one layer of using surface
The short fibre of carbon fiber of polymeric layer containing carboxylic acid functional.
The polycarbodiimide is the organic compound for containing multiple carbodiimide-baseds in molecule.Poly- carbonization two is sub-
Amine can be reacted with the group by the carbon fiber surface after oxidizing, be grafted to the surface of carbon fiber, and can with containing
The polymer reaction of carboxylic acid functional and increase unit mass carbon fiber surface grafting organic matter quality.Whether contain by molecule
There are aromatic structure, polycarbodiimide that can be divided into two kinds of aliphatic polycarbodiimide, aromatic polycarbodiimide.
Further, the polycarbodiimide is in aliphatic polycarbodiimide or aromatic polycarbodiimide
It is one or more.
Further, the polycarbodiimide is poly- isophorone carbodiimides, poly- hexahydrotoluene carbonization two
Imines, gathers to benzene carbodiimides, poly- 3,3 ', 5,5 '-tetra isopropyl diphenyl -4,4 '-carbonization two poly- isophthalic carbodiimides
It is one or more in imines.Preferably poly- hexahydrotoluene carbodiimides or poly- 3,3 ', 5,5 '-tetra isopropyl diphenyl-
It is one or more in 4,4 '-carbodiimides.
The polymer containing carboxylic acid functional is the organic polymer containing carboxyl in middle molecule, can be with carbon fiber surface
The polycarbodiimide reaction of face grafting, further increases the quality of unit mass carbon fiber surface grafting organic matter, improves ring
Effect of impregnation of the oxygen compound in carbon fiber surface.Specific such as poly and its copolymer, gathers polyacrylic acid and its copolymer
Methacrylic acid and its copolymer, poly-aspartate and its polymer or one kind or more in poly-epoxy succinic acid and its polymer
Kind；Preferably, the polymer containing carboxylic acid functional be poly and its copolymer, polyacrylic acid and its copolymer or
It is one or more in polymethylacrylic acid and its copolymer.
Further, the polymer containing carboxylic acid functional be poly and its copolymer, polyacrylic acid and its
It is one or more in copolymer or polymethylacrylic acid and its copolymer.
Further, the polymer containing carboxylic acid functional is poly acrylic acid-poly acrylamide.
Epoxide refers to the compound containing epoxy-functional.It can be anti-with the hydroxyl of modified carbon fiber surface
It answers, is grafted to carbon fiber surface, meanwhile, it can also be grafted to its point with the hydroxyl reaction in polyethylene naphthalate
In subchain.Since a large amount of organic molecule chain and the production of epoxide hydroxyl reaction are contained in the surface of surface-modified carbon fiber
Object, the also reaction product containing epoxide and hydroxyl on polyethylene naphthalate strand, to improve carbon fiber
With the interface compatibility of polyethylene naphthalate, composite inner defect is reduced, improves carbon fiber reinforced polyester resin
Mechanical strength.It is preferred that the compound containing 2 or 2 or more epoxy-functionals in each molecule of the epoxide.
It is preferred that in terms of 100 parts by weight of polyethylene naphthalate, the epoxide is 1~5 parts by weight.
Further, the epoxide contains epoxidized soybean oil, polyethyleneglycol diglycidylether or poly- the third two
It is one or more in alcohol diglycidyl ether.
Further, inorganic salts can also be contained in a kind of short fine enhancing thermoplastic polyurethane of carbon fiber, for tristearin
It is one or more in hydrochlorate, caprylate, caprate or citrate.The speed of epoxide and pet reaction can be improved
Rate improves mechanical property, specifically such as, zinc stearate, Sodium Caprylate, ironic citrate and barium caprate.Preferably ironic citrate and capric acid
One or both of barium.With polyethylene naphthalate for 100 listed as parts by weight, contain 0.1~2 parts by weight, preferably
0.5~1 parts by weight.
Further, the inorganic salts are the mixture of ironic citrate and barium caprate.Two kinds of mass ratio is (1:1)~
(1:10), preferably (1:3)~(1:8).
Further, a kind of short fine strengthened thermoplastic polyester preparation method of carbon fiber comprises the steps of：
Step A：Under nitrogen atmosphere protection, the short fibre of carbon fiber is heated 0.5 hour or more at 250~450 DEG C；For
The removal for going slurry processing and impurity of carbon fiber, temperature is too low, and the time is too short, influences the treatment effect of subsequent step, to shadow
Ring the mechanical strength of carbon fibre composite.Preferably, heating temperature is 300~400 DEG C, and heating time is more than 2 hours.
Step B：The short fibre of carbon fiber that step A is obtained is immersed in pH<In 5 solution, heated 2 hours at 40~70 DEG C
More than；Oxygen-containing group can be introduced with carbon oxide fiber surface, prepared for subsequent carbon fiber surface modification.Wherein, solution is
Acid solution with strong oxidizing property, it is specific such as sulfuric acid-liquor potassic permanganate, it is salpeter solution, sulfuric acid-potassium bichromate solution, dense
Sulfuric acid solution and its mixed liquor.Preferably, solution is the salpeter solution of 0.1~10mol/L, and heating temperature is 50~60 DEG C, is added
The hot time is more than 4 hours.
Step C：The short fibre of carbon fiber that step B is obtained is immersed in the solution containing polycarbodiimide 0.5 hour or more；
It can allow the carbon fiber of surface oxidation and polycarbodiimide react and surface coats a strata carbodiimides.Containing poly- carbonization two
The solution of imines is specifically such as the benzole soln of polycarbodiimide, the carbon tetrachloride solution of polycarbodiimide, polycarbodiimide
Ethyl acetate solution, polycarbodiimide dichloromethane solution, polycarbodiimide content is 5~50wt% in solution,
It is preferred that 8~30wt%.Time of the impregnated carbon fiber in the solution containing polycarbodiimide is more than 1 hour, and the temperature of dipping is big
In 20 DEG C；It is preferred that dipping temperature is 40~60 DEG C, dip time is 1~3 hour.
Step D：The short fibre of carbon fiber that step C is obtained heats 0.5 hour or more at 60~100 DEG C；Promote previous step
The reaction was complete carries out, and removes the solvent of the polycarbodiimide solution adhered on carbon fiber, it is preferred that heating time is more than 1
Hour.
Step E：It is small that the short fibre of carbon fiber that step D is obtained is immersed in the aqueous solutions of polymers containing carboxylic acid functional 0.5
When more than；In the aqueous solutions of polymers containing carboxylic acid functional the mass fraction of the polymer containing carboxylic acid functional be 5~
50wt%, preferably 8~30wt%.Preferably, the dip time of carbon fiber should be greater than 1 hour, and dipping temperature should be greater than 20 DEG C.
Step F：Once again, the short fibre of the carbon fiber that step E is obtained heats 0.5 hour or more at 60~100 DEG C；It allows
Single step reaction is fully completed, and removes moisture therein.Preferably, the time of heating is more than 1 hour.
Step G：PART EPOXY compound is taken, the carbon fiber that step F is obtained is short fine with epoxide premixing, makes ring
Oxygen compound is coated on the surface of the short fibre of carbon fiber；Promote thermoplastic resin carbon fiber surface bond, be not in gap and
It is divided into phenomenon, improves the compactness of composite material, enhances the mechanical performance of composite material.This step has used epoxide total
The 30~70%, preferably 45~55% of amount, in this way, can further promote the compatibility of carbon fiber and resin.
Step H：Using tools such as extruder, mixers, under heating, shear action, by polyethylene naphthalate,
Short fine, the remaining epoxide of carbon fiber of epoxide and inorganic salt blend have been coated made from step G.
Advantageous effect：The short fine strengthened thermoplastic polyester of carbon fiber of the present invention is by carrying out at the modification of surface carbon fiber
Reason, by the effect of polycarbodiimide and carboxylic acid, carbon fiber surface form at least one layer of polycarbodiimide layer and
At least one layer of polymeric layer containing carboxylic acid functional then, in modified carbon fiber and polyethylene naphthalate is distinguished
Epoxide is added, improves the compatibility of carbon fiber and polyethylene naphthalate, improves the short fine enhancing heat of carbon fiber
The performance of plasticity polyester composite.
Further, inventor has found that partial salts compound is very helpful for the raising of this system mechanical property, especially
It is the addition that ironic citrate and barium caprate have synergistic effect, can substantially increase epoxide and reacting for polyester is fast
Rate improves the mechanical property of material.
Specific implementation mode：
Test event and its test method of the present invention：
Tensile strength：It is measured by GB/T1447-2005, the size of sample is：Length × width x thickness=250mm × 25mm ×
5mm；Gauge length=100mm；Tensile speed=5mm/min.
Bending strength：It is carried out according to GB/T 1449-2005.The size of sample is：Length × width x thickness=80mm × 15mm ×
4mm；Test speed=2mm/min.
The embodiment of the present invention and comparative example are raw materials used：
【Polyethylene naphthalate】Japanese Teijin Ltd produces TN-8065S；
【The short fibre of carbon fiber】Toray Co., Ltd. produces T008-003, length 3mm；
【Epoxide】
H1：Ethylene glycol diglycidylether：Shanghai such as hair Chemical Industry Science Co., Ltd production RF-162, epoxide number >=
0.65mol/L。
H2：Polyethyleneglycol diglycidylether：Shanghai such as hair Chemical Industry Science Co., Ltd production PEGGE-400, epoxide number=
0.30~0.36mol/L.
H3：Epoxidized soybean oil:Dongguan Ling Chuan environment-friendly materials Science and Technology Ltd. produces, and acid value≤0.5%, epoxy content >=
6.2%, iodine number≤3.0%；
H4：Polypropylene glycol diglycidyl ether：Shanghai such as hair Chemical Industry Science Co., Ltd produces RF-PPGDGE400, epoxide number
For 0.28~0.36mol/L；
【Inorganic salts】
Y1：Ironic citrate：Nantong Feiyu Fine Chemicals Co., Ltd. produces；
Y2：Barium caprate：It produces the bio tech ltd Guang Zhonglaiyu；
Y3：Anhydrous acetic acid calcium：The industrial top grade of Wuxi Ao Nite Chemical Co., Ltd.s production；
Y4：Zinc stearate：Shijiazhuang Fu Run reaches Chemical Industry Science Co., Ltd, 400 mesh of fineness；
【Polycarbodiimide】
A1：The carbon tetrachloride solution of poly- diphenyl methane carbodiimides：Poly- diphenyl methane carbodiimides is (by hexichol
Dicyclohexylmethane diisocyanate catalyst phosphine oxide moiety effect under be made) be dissolved in carbon tetrachloride be made, a concentration of 20wt%.
A2：The carbon tetrachloride solution of poly- hexahydrotoluene carbodiimides：Poly- hexahydrotoluene carbodiimides is (by methyl
Cyclohexane diisocyanate catalyst phosphine oxide moiety effect under be made) be dissolved in carbon tetrachloride be made, a concentration of 20wt%.
【Polymer containing carboxylic acid functional】
S1：The aqueous solution of polyacrylic acid：Polyacrylic acid (Changzhou Run Yang Chemical Co., Ltd.s production GY303) is dissolved in water system
, a concentration of 20wt%.
S2：The aqueous solution of poly acrylic acid-poly acrylamide：Poly acrylic acid-poly acrylamide is (by acrylic monomers and propylene
Amide monomer solution be copolymerized under the action of potassium peroxydisulfate be made) be dissolved in water be made, a concentration of 20wt%.
Embodiment 1~14
According to the formula of raw material in table 1, the short fine strengthened thermoplastic polyester of carbon fiber is prepared according to following production method.
Step A：Under nitrogen atmosphere protection, by carbon fiber short fine (toray Co., Ltd. production T008-003, length
3mm) heated 2 hours at 350 DEG C；
Step B：The short fibre of carbon fiber made from step A is immersed in the salpeter solution of 1mol/L, it is small that 4 are heated at 50 DEG C
When；
Step C：The short fibre of carbon fiber made from step B is immersed in 50 DEG C of solution containing polycarbodiimide 2 hours；
Step D：The short fibre of carbon fiber made from step C is heated 2 hours at 60 DEG C；
Step E：The short fibre of carbon fiber that step D is obtained is immersed in 2 in 30 DEG C of aqueous solutions of polymers containing carboxylic acid functional
Hour；
Step F：Once again, the short fibre of carbon fiber made from step E is heated 2 hours at 80 DEG C；
Step G：PART EPOXY compound is taken, the short fibre of carbon fiber made from step F is premixed with epoxide at 30 DEG C
It closes 2 hours；
Step H：Using mixer, at 280 DEG C, 100rpm, will be wrapped made from polyethylene naphthalate, step G
The short fine and remaining epoxide of carbon fiber and inorganic salts mixing 10min of epoxide are covered.
Finally, after 280 DEG C of compression moldings, it is cooled to room temperature.
Table 1：The formula of raw material
Comparative example 1：
The composition of raw materials and preparation method of reference implementation example 1, but the short fine surface without step A~H of carbon fiber is modified
Processing, surface do not have a polycarbodiimide layer and the polymeric layer containing carboxylic acid functional, directly with polyethylene naphthalate,
Epoxide is mixed with out the short fine strengthened thermoplastic polyester of carbon fiber.
Comparative example 2：
The composition of raw materials and preparation method of reference implementation example 1, but it is added without epoxide, prepare the short fine increasing of carbon fiber
Strong thermoplastic polyester.
Comparative example 3：
The composition of raw materials and preparation method of reference implementation example 1, but carbon fiber is not immersed in polycarbodiimide solution, system
It is standby go out the short fine strengthened thermoplastic polyester of carbon fiber.
Comparative example 4：
The composition of raw materials and preparation method of reference implementation example 1, but carbon fiber is not immersed in the polymer containing carboxylic acid functional
In aqueous solution, the short fiber reinforced polyester of carbon fiber is prepared.
Comparative example 5：
The composition of raw materials and preparation method of reference implementation example 4, but the short fine surface without step A~F of carbon fiber is modified
Processing, surface do not have a polycarbodiimide layer and the polymeric layer containing carboxylic acid functional, directly with polyethylene naphthalate,
Epoxide is mixed with out the short fine strengthened thermoplastic polyester of carbon fiber.
The short fiber reinforced polyester sample of carbon fiber that each embodiment and comparative example is prepared carries out the measurement of mechanical performance,
Measurement result is as shown in table 2.
Table 2：Properties of sample measurement result
| Performance | Tensile strength (MPa) | Bending strength (MPa) |
| Embodiment 1 | 150 | 245 |
| Embodiment 2 | 193 | 300 |
| Embodiment 3 | 158 | 252 |
| Embodiment 4 | 164 | 259 |
| Embodiment 5 | 169 | 265 |
| Embodiment 6 | 174 | 271 |
| Embodiment 7 | 175 | 272 |
| Embodiment 8 | 186 | 283 |
| Embodiment 9 | 183 | 280 |
| Embodiment 10 | 188 | 291 |
| Embodiment 11 | 190 | 290 |
| Embodiment 12 | 199 | 301 |
| Embodiment 13 | 200 | 302 |
| Embodiment 14 | 205 | 308 |
| Comparative example 1 | 123 | 182 |
| Comparative example 2 | 140 | 225 |
| Comparative example 3 | 130 | 192 |
| Comparative example 4 | 136 | 214 |
| Comparative example 5 | 158 | 250 |
From Table 2, it can be seen that compared with comparative example, the short fine enhancing of carbon fiber prepared by embodiment according to the invention is hot
Tensile strength, the bending strength of plasticity polyester are greatly improved.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto.
Any one skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (9)
1. a kind of short fine strengthened thermoplastic polyester of carbon fiber, which is characterized in that include following components：
100 parts by weight of polyethylene naphthalate；
Short fine 10~100 parts by weight of carbon fiber；
0.1~5 parts by weight of epoxide；
Wherein, the short fine average length of the carbon fiber is 1~5mm, and the short fibre of carbon fiber is surface-modified, and surface has extremely
A few strata carbodiimides layer and at least one layer of polymeric layer containing carboxylic acid functional.
2. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 1, which is characterized in that the poly- carbonization two
Imines is one or more in aliphatic polycarbodiimide or aromatic polycarbodiimide.
3. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 2, which is characterized in that the poly- carbonization two
Imines is poly- isophorone carbodiimides, poly- hexahydrotoluene carbodiimides, poly- isophthalic carbodiimides, gathers to benzene carbonization
It is one or more in diimine or poly- 3,3 ', 5,5 '-tetra isopropyl diphenyl -4,4 '-carbodiimides.
4. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 1, which is characterized in that described contains carboxylic acid
The polymer of functional group is poly and its copolymer, polyacrylic acid and its copolymer or polymethylacrylic acid and its copolymer
In it is one or more.
5. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 4, which is characterized in that described contains carboxylic acid
The polymer of functional group is poly acrylic acid-poly acrylamide.
6. according to a kind of short fine strengthened thermoplastic polyester of carbon fiber of claim 1-5 any one of them, which is characterized in that described
Epoxide contain one kind in epoxidized soybean oil, polyethyleneglycol diglycidylether or polypropylene glycol diglycidyl ether or
It is a variety of.
7. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 6, which is characterized in that also contain inorganic salts
0.1~2 parts by weight, the inorganic salts are one or more in stearate, caprylate, caprate or citrate.
8. a kind of short fine strengthened thermoplastic polyester of carbon fiber according to claim 7, which is characterized in that the inorganic salts are
The mixture of ironic citrate and barium caprate, wherein the mass ratio of ironic citrate and barium caprate is (1:1)~(1:10).
9. according to a kind of short fine strengthened thermoplastic polyester of carbon fiber of claim 1-8 any one of them, which is characterized in that it is made
Preparation Method comprises the steps of：
Step A：Under nitrogen atmosphere protection, the short fibre of carbon fiber is heated 0.5 hour or more at 250~450 DEG C；
Step B：The short fibre of carbon fiber that step A is obtained is immersed in pH<In 5 solution, heated at 40~70 DEG C 2 hours with
On；
Step C：The short fibre of carbon fiber that step B is obtained is immersed in the solution containing polycarbodiimide 0.5 hour or more；
Step D：The short fibre of carbon fiber that step C is obtained heats 0.5 hour or more at 60~100 DEG C；
Step E：By the short fibre of carbon fiber that step D is obtained be immersed in the aqueous solutions of polymers containing carboxylic acid functional 0.5 hour with
On；
Step F：Once again, the short fibre of the carbon fiber that step E is obtained heats 0.5 hour or more at 60~100 DEG C；
Step G：PART EPOXY compound is taken, the carbon fiber that step F is obtained is short fine with epoxide premixing, makes epoxidation
Close the surface that object is coated on the short fibre of carbon fiber；
Step H：Using tools such as extruder, mixers, under heating, shear action, by polyethylene naphthalate, step
The short fine and remaining epoxide of carbon fiber that epoxide has been coated made from G is blended.
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| CN201810590891.9A CN108752878A (en) | 2018-06-09 | 2018-06-09 | A kind of fibre reinforced thermoplastic polyester |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105683293A (en) * | 2013-10-29 | 2016-06-15 | 东丽株式会社 | Fiber-reinforced resin composition, and fiber-reinforced composite material |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105683293A (en) * | 2013-10-29 | 2016-06-15 | 东丽株式会社 | Fiber-reinforced resin composition, and fiber-reinforced composite material |
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Application publication date: 20181106 |