CN105860009B - A kind of polyurethane of the structure containing electrophilic and preparation method thereof - Google Patents
A kind of polyurethane of the structure containing electrophilic and preparation method thereof Download PDFInfo
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- CN105860009B CN105860009B CN201610374738.3A CN201610374738A CN105860009B CN 105860009 B CN105860009 B CN 105860009B CN 201610374738 A CN201610374738 A CN 201610374738A CN 105860009 B CN105860009 B CN 105860009B
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a kind of polyurethane of structure containing electrophilic, using organic acid dianhydride, hydroxylamine, diisocyanate and oligomer dihydric alcohol as raw material, the new polyurethane of preparation is increased dramatically compared to mechanical performances such as traditional elastomeric material elasticity, modulus, intensity and elongation at break, due to the presence of electrophilic structure, the polyurethane material can prepare functional material with various functionalization filler compoundings, have potential application in fields such as machinery, chemical industry, functional materials.The invention further relates to preparation method, have many advantages, such as simply, easy to implement and control, production efficiency are higher.
Description
Technical field
The present invention relates to polyurethane fields, and in particular to a kind of polyurethane of the structure containing electrophilic and preparation method thereof.
Background technique
Polyurethane material is the current best thermal insulation material of performance in the world.Main chain constitutional repeating unit Han-NHCOO-
One quasi polymer.It is polymerized by isocyanates (monomer) with hydroxy compounds.Due to containing highly polar carbamate groups, no
It is dissolved in non-polar group, there is good oil resistivity, toughness, wearability, resistance to ag(e)ing and adhesiveness.It can be made with different material
Adapt to the material of wide temperature range (- 50~150 DEG C), including elastomer, thermoplastic resin and thermosetting resin.Under high temperature not
Hydrolysis, also not alkali-proof medium.
Common monomer such as toluene di-isocyanate(TDI), diisocyanate diphenyl-methane etc..3 classes of polyalcohol point: simple polynary
Alcohol (ethylene glycol, glycerine etc.)；Polyester oligomer containing terminal hydroxyl, for preparing polyester polyurethane；Containing terminal hydroxyl
Polyether oligomers, for preparing polyether polyurethane.Polymerization is different with material properties.It is first prepared when synthetic elastomer low
Molecular weight dihydric alcohol, then reacted with excessive aromatic isocyanate, the prepolymer that isocyanates is end group is generated, then expand with butanediol
Chain obtains thermoplastic elastomer；If being crosslinked with aromatic diamine chain extension and further, casting type elastomer is obtained.Prepolymer hydrazine or
Diamine chain extension, obtains elastomer；Excessively more performed polymer mixes isocyanates with catalyst, foaming agent, can directly obtain
To rigid foam.Such as monomer, polyethers, water, catalyst are mixed, flex foam can be obtained in single step reaction.It is single
Body reacts in the solution with polyalcohol, and coating can be obtained；Adhesive then with polyisocynate monomer and low molecular weight polyester or gathers
Ether is mixed and is reacted when in use.
Currently, polyurethane material is synthesized by diisocyanate with oligomer polyol two-step method, generated by microphase-separated
Special construction assign the preferable mechanical performance of polyurethane, but since rigid chain segment hydrogen bond action deficiency frequently results in polyurethane
The problems such as mechanical performance declines.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide the polyurethane and its system of a kind of structure containing electrophilic
Preparation Method, the polyurethane of the structure containing electrophilic being prepared compared to traditional elastomeric material, elasticity, modulus, intensity with
And the mechanical performances such as elongation at break are increased dramatically, and have potential application in fields such as machinery, chemical industry.
A kind of technical solution provided by the present invention are as follows: polyurethane of the structure containing electrophilic, wherein the polyurethane
Structural formula is as follows:
In formula (I), n is that 1~5, m is 1~30；
The polyurethane is obtained by following structural formula (II), (III) and (IV) reaction:
HO-R1-OH (Ⅱ)；
O=C=N-R2- N=C=O (III)；
HO-R3-OH (Ⅳ)；
The formula (II) is oligomer dihydric alcohol；Described (III) is diisocyanate；The formula (IV) is by organic
Acid dianhydride reacts to obtain with hydroxylamine.
In above-mentioned technical proposal, the polyurethane of the structure containing electrophilic is prepared by conventional organic micromolecule compound, energy
All kinds of polyurethane synthesis are enough widely used in, the mechanical performance of polyurethane material is substantially improved, can be widely applied to chemical industry, machinery etc.
Field.Hydroxy-end capped acid imide ring-type chain extender is reacted to obtain by organic acid dianhydride and hydroxylamine, and reaction is related to polyimides
Synthesis chemistry is cyclized polyamic acid by controlling temperature.Due to the presence of electrophilic structure, the polyurethane material can with it is each
Kind functionalization filler compounding prepares functional material, has potential application in fields such as machinery, chemical industry, functional materials.
Preferably, organic acid dianhydride is hexafluorodianhydride (6FDA), pyromellitic dianhydride, 4,4 '-biphenyl ether dianhydrides, second two
Amine tetrem acid dianhydride, -3,4,9,10- tetracarboxylic dianhydride, 3,3', 4,4'- bibenzene tetracarboxylic dianhydride, 3,3'4,4'- hexichol first
Ketone tetracarboxylic dianhydride, diethylene-triamine pentaacetic acid dianhydride, bicyclic [2.2.2] octyl- 7- alkene -2,3,5,6- tetracarboxylic dianhydride, 1,
4,5,8- naphthalenetetracarbacidic acidic dianhydride, Bisphenol A Type Diether Dianhydride, 1.2.4.5- cyclohexanetetracarboxylic acid dianhydride, 3,3,4,4- diphenyl ether four
One or more of formic acid dianhydride or the chloro- 3,4,9,10- tetracarboxylic acid dianhydride of 1,6,7,12- tetra-.
Preferably, the hydroxylamine be ethanol amine, isopropanolamine, n-propanolamine, diglycolamine, D- aminopropanol,
One of the different bright amine alcohol of hydroxyl acetamide, L-, 4- amino-n-butyl alcohol, 5- amino -1- amylalcohol or 6- amino -1- hexanol are several
Kind.
Preferably, the oligomer dihydric alcohol is polyester diol or polyether Glycols.Further preferably, described
Polyether Glycols are polytetrahydrofuran ether glycol.The polytetrahydrofuran ether glycol is polytetrahydrofuran 250, polytetrahydrofuran
650, polytetrahydrofuran 1000, polytetrahydrofuran 2000 or polytetrahydrofuran 3000.
Preferably, the diisocyanate is toluene di-isocyanate(TDI), methyl diphenylene diisocyanate, 1,5- naphthalene
Diisocyanate, hexamethylene diisocyanate, isofoer diisocyanate, benzene dimethylene diisocyanate or to benzene two
One or more of isocyanates.
The present invention also provides a kind of preparation methods of such as polyurethane of the above-mentioned structure containing electrophilic, which is characterized in that including
Following step:
1) in polar solvent, organic acid dianhydride is added and reacts 10~14h with hydroxylamine, generates amide acid solution, is added
Temperature is risen to 160~180 DEG C, flowed back 2~4 hours by water entrainer, and water entrainer takes the water that amic acid cyclisation generates out of, is obtained
Hydroxy-end capped acid imide ring-type chain extender；
2) oligomer dihydric alcohol and diisocyanate are added in polar solvent, under the action of catalyst, urethane occur
Change reaction, obtains polyurethane prepolymer；
3) determination step 2) in polyurethane prepolymer-content of NCO group, it is cyclic annular that hydroxy-end capped acid imide is added
Chain extender is warming up to 70~90 DEG C of 2~3h of reaction；
4) reaction system in step 3) is added in methanol, product is precipitated to get the poly- ammonia of the structure containing electrophilic in filtering
Ester.
Above-mentioned preparation method, preparation method is simple, and easy to implement and control, production efficiency is higher, equipment is simple.
Preferably, the polar solvent is n,N-Dimethylformamide, n,N-dimethylacetamide or dimethyl sulfoxide.
Preferably, catalyst is tertiary amine or organotin in the step 2).Further preferably, the catalyst is
Dibutyltin dilaurate catalyst.
Preferably, the molar ratio of oligomer dihydric alcohol and diisocyanate is 1:2~2.1 in the step 2).
Preferably, mole of hydroxy-end capped acid imide ring-type chain extender and-NCO group is added in the step 3)
Than being 0.5~0.55.
Preferably, the method for measurement-NCO group content is infrared spectroscopy detection in the step 3).
Compared with the existing technology, the beneficial effects of the present invention are embodied in:
(1) preparation method of the polyurethane of hydroxy-end capped acid imide ring-type chain extender and the structure containing electrophilic is more simple
It is single, and the mechanical performance of polymer material is increased dramatically compared with conventional urethane material.
(2) in the polyurethane of the structure containing electrophilic, due to the presence of electrophilic structure, the polyurethane material can with it is various
Functionalization filler compounding prepares functional material, has potential application in fields such as machinery, chemical industry, functional materials.
Detailed description of the invention
Fig. 1 is the stress-strain diagram of the polyurethane of the structure containing electrophilic prepared in embodiment 1；
Fig. 2 is the nmr spectrum of the polyurethane of the structure containing electrophilic prepared in embodiment 1.
Specific embodiment
Below with reference to embodiment, the present invention is further explained.
Nuclear magnetic resonance spectroscopy in embodiment1H-NMR uses the III type spectroscope of 400AVANCE of Brooker company (Bruker)
(Spectrometer) it measures, 400MHz, solvent is deuterated dimethyl sulfoxide.
Embodiment 1
100mlN is added in 10g pyromellitic acid anhydride, 5.0g ethanol amine, in dinethylformamide, is stirred under room temperature
12h is reacted, amide acid solution is generated, 30ml toluene is added into above-mentioned amic acid solution, temperature is risen to 170 DEG C, by dividing
Hydrophone constantly separates the water that amic acid cyclisation generates, and water to be separated reaches variable, stops reaction, is evaporated under reduced pressure removal system
In toluene and n,N-Dimethylformamide, drying obtain hydroxy-end capped imide ring chain extender.
It is characterized by nuclear magnetic resonance spectroscopy, nuclear magnetic data is as follows:
δ/ppm=3.55-3.75 (m, 4H), 4.83-4.93 (m, 2H), 8.20 (s, 2H)
Obtained product such as formula I:
By 4g polytetrahydrofuran ether glycol (molecular weight 650), 30g N, N- is added in 2.07g hexamethylene diisocyanate
In dimethylformamide, and 3-5 drop dibutyltin dilaurate catalyst is added dropwise, reacts 4h at 65 DEG C.
Measure the content of-NCO in above-mentioned system, the hydroxy-end capped acid imide chain extender of the amount 1/2 of addition-NCO substance,
80 DEG C are raised the temperature to, the reaction was continued 2h.
Above-mentioned reactant is added in methanol, product is precipitated, filters out product, is dissolved in appropriate N, N- dimethyl methyl
In amide, solution is poured into mold, drying and moulding obtains the film of polyether polyols containing imide structure.
The ess-strain performance of the polyurethane of the structure containing electrophilic is measured, as a result as shown in Figure 1.
The polyurethane of the resulting structure containing electrophilic is characterized by nuclear magnetic resonance spectroscopy, as shown in Figure 2.
Embodiment 2
10g pyromellitic acid anhydride, 6.9g Propanolamine are added in 100ml n,N-dimethylacetamide, stirred under room temperature
12h is reacted, amide acid solution is generated, 30ml toluene is added into above-mentioned amic acid solution, temperature is risen to 170 DEG C, by dividing
Hydrophone constantly separates the water that amic acid cyclisation generates, and water to be separated reaches variable, stops reaction, is evaporated under reduced pressure removal system
In toluene and n,N-dimethylacetamide, drying obtain hydroxy-end capped imide ring chain extender.
Obtained product such as formula II:
By 6.2g polytetrahydrofuran ether glycol (molecular weight 1000), 30gN is added in 2.07g hexamethylene diisocyanate,
In dinethylformamide, and 3-5 drop dibutyltin dilaurate catalyst is added dropwise, reacts 4h at 65 DEG C.
Measure the content of-NCO in above-mentioned system, the hydroxy-end capped acid imide chain extender of the amount 1/2 of addition-NCO substance,
80 DEG C are raised the temperature to, the reaction was continued 2h.
Above-mentioned reactant is added in methanol, product is precipitated, filters out product, is dissolved in appropriate N, N- dimethyl methyl
In amide, solution is poured into mold, drying and moulding obtains the film of polyether polyols containing imide structure.
Embodiment 3
10g pyromellitic acid anhydride, 5.0g ethanol amine are added in 100ml dimethyl sulfoxide, are stirred to react 12h under room temperature,
Amide acid solution is generated, 30ml toluene is added into above-mentioned amic acid solution, temperature is risen to 170 DEG C, it is continuous by water segregator
The water that amic acid cyclisation generates is separated, water to be separated reaches variable, stops reaction, the toluene being evaporated under reduced pressure in removal system
And n,N-Dimethylformamide, drying obtain hydroxy-end capped imide ring chain extender.Such as formula III:
By 12.4g polytetrahydrofuran ether glycol (molecular weight 2000), 30g is added in 2.07g hexamethylene diisocyanate
In n,N-Dimethylformamide, and 3-5 drop dibutyltin dilaurate catalyst is added dropwise, reacts 4h at 65 DEG C.
Measure the content of-NCO in above-mentioned system, the hydroxy-end capped acid imide chain extender of the amount 1/2 of addition-NCO substance,
80 DEG C are raised the temperature to, the reaction was continued 2h.
Above-mentioned reactant is added in methanol, product is precipitated, filters out product, is dissolved in appropriate N, N- dimethyl methyl
In amide, solution is poured into mold, drying and moulding obtains the film of polyether polyols containing imide structure.
Embodiment 4
4,4 '-biphenyl ether dianhydride of 10g, 3.94g ethanol amine are added in 100ml dimethyl sulfoxide, are stirred to react under room temperature
12h generates amide acid solution, and 30ml toluene is added into above-mentioned amic acid solution, temperature is risen to 170 DEG C, passes through water segregator
The water that amic acid cyclisation generates constantly is separated, water to be separated reaches variable, stops reaction, is evaporated under reduced pressure in removal system
Toluene and n,N-Dimethylformamide, drying obtain hydroxy-end capped imide ring chain extender.Such as formula IV:
By 6.2g polytetrahydrofuran ether glycol (molecular weight 1000), 30gN is added in 2.07g hexamethylene diisocyanate,
In dinethylformamide, and 3-5 drop dibutyltin dilaurate catalyst is added dropwise, reacts 4h at 65 DEG C.
Measure the content of-NCO in above-mentioned system, the hydroxy-end capped acid imide chain extender of the amount 1/2 of addition-NCO substance,
80 DEG C are raised the temperature to, the reaction was continued 2h.
Above-mentioned reactant is added in methanol, product is precipitated, filters out product, is dissolved in appropriate N, N- dimethyl methyl
In amide, solution is poured into mold, drying and moulding obtains the film of polyether polyols containing imide structure.
Embodiment 5
The equal tetracarboxylic acid dianhydride of 10g, 1.92g isopropanolamine are added in 100ml n,N-dimethylacetamide, under room temperature
It is stirred to react 12h, generates amide acid solution, 30ml toluene is added into above-mentioned amic acid solution, temperature is risen to 170 DEG C, is led to
It crosses water segregator and constantly separates the water that amic acid cyclisation generates, water to be separated reaches variable, stops reaction, vacuum distillation removal
Toluene and n,N-dimethylacetamide in system, drying obtain hydroxy-end capped imide ring chain extender.
Obtained product such as formula V:
By 12.4g polytetrahydrofuran ether glycol (molecular weight 2000), 2.07g hexamethylene diisocyanate is added
In 30gN.N- dimethylformamide, and 3-5 drop dibutyltin dilaurate catalyst is added dropwise, reacts 4h at 65 DEG C.
Measure the content of-NCO in above-mentioned system, the hydroxy-end capped acid imide chain extender of the amount 1/2 of addition-NCO substance,
80 DEG C are raised the temperature to, the reaction was continued 2h.
Above-mentioned reactant is added in methanol, product is precipitated, filters out product, is dissolved in appropriate N, N- dimethyl methyl
In amide, solution is poured into mold, drying and moulding obtains the film of polyether polyols containing imide structure.
Performance test
The polyurethane containing electrophilic structure being prepared in embodiment 1 measures its elasticity modulus, tensile stress, breaks
Elongation, response rate and molecular weight are split, as a result as shown in the table.
Above-mentioned is to elaborate in conjunction with the embodiments to the present invention, but embodiments of the present invention are not by above-mentioned implementation
The limitation of example, other any changes made under the invention patent core guiding theory, combine simplified etc. be included at replacement
Within the scope of protection of the patent of the present invention.
Claims (8)
1. a kind of polyurethane elastomer of structure containing electrophilic, which is characterized in that the structural formula of the polyurethane elastomer is such as
Under:
In formula (I), n is that 1~5, m is 1~30；
The polyurethane elastomer is obtained by following structure formula (II), (III) and (IV) reaction:
HO-R1-OH (II)；
O=C=N-R2- N=C=O (III)；
HO-R3-OH (IV)；
The formula (II) is oligomer dihydric alcohol；(III) is diisocyanate；The formula (IV) is by organic acid two
Acid anhydride reacts to obtain with hydroxylamine；The oligomer dihydric alcohol is polyester diol or polyether Glycols；The diisocyanate
Ester be toluene di-isocyanate(TDI), methyl diphenylene diisocyanate, 1,5- naphthalene diisocyanate, hexamethylene diisocyanate,
One or more of isofoer diisocyanate, benzene dimethylene diisocyanate or paraphenylene diisocyanate.
2. the polyurethane elastomer of the structure according to claim 1 containing electrophilic, which is characterized in that the organic acid two
Acid anhydride is hexafluorodianhydride (6FDA), pyromellitic dianhydride, 4,4 '-biphenyl ether dianhydrides, ethylenediamine tetra-acetic acid dianhydride, -3,4,9,10- tetrabasic carboxylic acids
Dianhydride, 3,3 ', 4,4 '-bibenzene tetracarboxylic dianhydrides, 3,3 ' 4,4 '-benzophenone tetracarboxylic dianhydrides, diethylene-triamine pentaacetic acid
Dianhydride, bicyclic [2.2.2] octyl- 7- alkene -2,3,5,6- tetracarboxylic dianhydrides, Isosorbide-5-Nitrae, 5,8- naphthalenetetracarbacidic acidic dianhydrides, bisphenol A-type diether two
Acid anhydride, 1.2.4.5- cyclohexanetetracarboxylic acid dianhydride, 3,3,4,4- diphenyl ether tetraformic dianhydrides or 1,6,7,12- tetra- chloro- 3,4,9,10-
One or more of tetracarboxylic acid dianhydride.
3. the polyurethane elastomer of the structure according to claim 1 containing electrophilic, which is characterized in that the hydroxylamine is
The different bright amine alcohol of ethanol amine, isopropanolamine, n-propanolamine, diglycolamine, D- aminopropanol, hydroxyl acetamide, L-, 4- amino -1-
One or more of butanol, 5- amino -1- amylalcohol or 6- amino -1- hexanol.
4. a kind of method for preparing polyurethane elastic body of the structure containing electrophilic as described in claims 1 to 3 is any, feature
It is, comprises the following steps that
1) in polar solvent, organic acid dianhydride is added and reacts 10~14h with hydroxylamine, generates amide acid solution, band water is added
Temperature is risen to 160~180 DEG C, flowed back 2~4 hours by agent, and water entrainer takes the water that amic acid cyclisation generates out of, obtains hydroxyl
The acid imide ring-type chain extender of sealing end；
2) oligomer dihydric alcohol and diisocyanate are added in polar solvent, under the action of catalyst, it is anti-that urethaneization occur
It answers, obtains polyurethane prepolymer；The oligomer dihydric alcohol is polyester diol or polyether Glycols；The diisocyanate
Ester be toluene di-isocyanate(TDI), methyl diphenylene diisocyanate, 1,5- naphthalene diisocyanate, hexamethylene diisocyanate,
One or more of isofoer diisocyanate, benzene dimethylene diisocyanate or paraphenylene diisocyanate；
3) determination step 2) in polyurethane prepolymer-content of NCO group, hydroxy-end capped acid imide ring-type chain extension is added
Agent is warming up to 70~90 DEG C of 2~3h of reaction；
4) reaction system in step 3) is added in methanol, product is precipitated to get the polyurethane bullet of the structure containing electrophilic in filtering
Property body.
5. the method for preparing polyurethane elastic body of the structure according to claim 4 containing electrophilic, which is characterized in that described
Step 2) in catalyst be tertiary amine or organotin.
6. the method for preparing polyurethane elastic body of the structure according to claim 4 containing electrophilic, which is characterized in that described
Step 2) in the molar ratio of oligomer dihydric alcohol and diisocyanate be 1: 2~2.1.
7. the method for preparing polyurethane elastic body of the structure according to claim 4 containing electrophilic, which is characterized in that described
Step 3) in the molar ratio of hydroxy-end capped acid imide ring-type chain extender and-NCO group is added is 0.5~0.55.
8. the method for preparing polyurethane elastic body of the structure according to claim 4 containing electrophilic, which is characterized in that described
Step 3) in measurement-NCO group content method be infrared spectroscopy detection.
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| CN110041502B (en) * | 2019-03-22 | 2021-01-26 | 中国科学院宁波材料技术与工程研究所 | Thermoplastic polyurethane elastomer and preparation method and application thereof |
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| CN111607058B (en) * | 2020-06-12 | 2021-12-10 | 苏州宝乾新材料科技股份有限公司 | High-thermal-conductivity thermoplastic imidized polyurethane material and preparation method thereof |
| CN113980338B (en) * | 2021-12-09 | 2023-05-30 | 万华化学集团股份有限公司 | Thermoplastic polyurethane foaming particle, preparation method and application thereof in low-temperature bending-resistant sole material |
| CN115260698B (en) * | 2022-08-25 | 2023-10-20 | 佛山市湘聚新材料有限公司 | Heat-conducting ABS and preparation method thereof |
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| CN103030763A (en) * | 2012-12-28 | 2013-04-10 | 青岛海洋新材料科技有限公司 | Polyimide modified polyisocyanurate foam and preparation method thereof |
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