CN109749078A - A kind of high temperature resistant nylon and preparation method thereof - Google Patents
A kind of high temperature resistant nylon and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of high temperature resistant nylon, structural formulas are as follows:Formulas I;OrFormula II;Wherein, the R1It is selected from、、、、One or more of;R2Selected from the aliphatic comprising 4~12 carbon atoms or aromatic alkyl.Diamine of the present invention by that will contain the binary acid of specific fragrant hexichol ether structure or containing specific fragrant hexichol ether structure is reacted with aliphatic or aromatic diamine or aliphatic or aromatic acid, fragrant hexichol ether structure is introduced into nylon molecules chain by realization, and the flexibility and fluidity of molten that high temperature resistant nylon is prepared are significantly improved;And the preparation method does solvent, the postprocessing working procedures of solvent-free recycling with water, and processing step is simple, improves production efficiency, reduces production cost, is suitble to large-scale mass production.
Description
Technical field
The present invention relates to technical field of polymer materials, and in particular to a kind of high temperature resistant nylon and preparation method thereof.
Background technique
Nylon has very excellent property, plays a very important role in engineering plastics.The synthesis of nylon is general
Just there are diacid and diamines to generate macromolecule nylon by polycondensation reaction.Fatty acid diacid is reacted with aliphatic diamine generates aliphatic
Phenyl ring is usually added in nylon molecules chain by nylon in order to improve the heat resistance of nylon, i.e. aromatic diacid and aliphatic two
Amine or the reaction of aliphatic diacid and aromatic diamine obtain the high-temperature nylon of fine heat-resisting performance, in currently on the market
PA6T/6, PA9T, PA10T, MXD6 etc..In order to preferably excavate the excellent properties of nylon, polymer chain structure is preferably utilized
Different structures is introduced into nylon molecules chain, Chinese patent by the relationship between performance there are many researcher
CN1935338A is reported is introduced into biphenyl structural in the strand of aromatic polyamide, to widen the material of reverse osmosis membrane
Range of choice.It is reported in Chinese patent CN103524730A and ether ketone structure is introduced into the strand of aromatic polyamides, with
The dissolubility of aromatic polyamides is improved, the compatibility of aromatic polyamide and PEEK is improved.Chinese patent CN105801843A will
Furans mechanism is introduced into aromatic polyamide, and the more excellent aramid fiber material of performance is made.
But up to the present, do not have also for fragrant hexichol ether structure to be introduced into nylon molecules chain both at home and abroad and be prepared
Nylon product relevant report.
Summary of the invention
In order to overcome the above-mentioned deficiencies of the prior art or defect, the purpose of the present invention is to provide a kind of flexibility and melts
Mobility is significantly improved high temperature resistant nylon.
It is a further object of the present invention to provide the preparation methods of above-mentioned high temperature resistant nylon.
The present invention is achieved through the following technical solutions:
A kind of high temperature resistant nylon, structural formula are as follows:
Formulas I;
Or
Formula II;
Wherein, the R1It is selected from、、、、One or more of;
R2Selected from the aliphatic comprising 4~12 carbon atoms or aromatic alkyl.
In addition, including the following steps: the invention also discloses the preparation method of above-mentioned high temperature resistant nylon
1) polymerization reaction: binary acid, diamine, reaction promoter, deionized water are proportionally added into reaction kettle, indifferent gas is used
Air in body displacement kettle, is filled with the inert gas of 0.05~0.2MPa, is warming up to 120 DEG C~180 DEG C, pressure is stablized 0.3
~1.1MPa reacts 1~2h, and temperature is then risen to 220 DEG C~260 DEG C, 1.5~4.8MPa of steady pressure, reacts 2h~6h
It slowly deflating, puts pressure in kettle to normal pressure afterwards in 1~2h, the reaction was continued 1~2h then discharges, and product crushes, drying,
It is spare;
2) thickening reaction: the polymeric reaction product of drying is added in rotary drum, and temperature is controlled at 240 DEG C~270 DEG C, is vacuumized
To -0.098MPa~-0.099Pa, 8h~16h is reacted, is discharged to get high temperature resistant nylon.
Wherein, in step 1), the binary acid is in comprising 4~12 fat of carbon atom races or aromatic diacid
It is one or several kinds of;And the diamine is selected from bisphenol A-type diphenyldiamine, bisphenol S type diphenyldiamine, '-biphenyl diphenol type
Diphenyldiamine, hydroquinone type diphenyldiamine, resorcinol type diphenyldiamine, two phenolic diphenyldiamine of more phenyl ring,
One of polycyclic fragrant two phenolic diphenyldiamine, two phenolic diphenyldiamine of heteroaromatic are several;The binary acid
Molar ratio with diamine is 1:1~1:1.1, preferably 1:1.01~1:1.05.
Wherein, in step 1), the diamine is in comprising 4~12 fat of carbon atom races or aromatic diamine
It is one or several kinds of;And the binary acid is selected from bisphenol A-type diphenyl ether diacid, bisphenol S type diphenyl ether diacid, '-biphenyl diphenol type
Diphenyl ether diacid, hydroquinone type diphenyl ether diacid, resorcinol type diphenyl ether diacid, two phenolic diphenyl ether diacid of more phenyl ring,
One of polycyclic fragrant two phenolic diphenyl ether diacid, two phenolic diphenyl ether diacid of heteroaromatic are several;The binary acid
Molar ratio with diamine is 1:1~1:1.1, preferably 1:1.01~1:1.05.
Wherein, in step 1), the reaction promoter is in end-capping reagent, catalyst, antioxidant, uvioresistant additive
It is one or several kinds of;The end-capping reagent is selected from one of benzoic acid, acetic acid, propionic acid or phthalic anhydride or several,
Additive amount is the 0.5%~2% of dicarboxylic acid monomer total mole number, preferably: 0.5%~1.5%;The catalyst is selected from sodium phosphate, phosphorus
It is sour calcium, sodium phosphite, Arizona bacilli, phosphorous acid magnesium, zinc phosphite, sodium hypophosphite, Lime Hypophosphate, ortho phosphorous acid magnesium, secondary
One of zinc phosphite is several, and additive amount is the 0.01%~0.05% of binary acid and diamine monomer gross mass;It is described
Antioxidant is selected from one of antioxidant 1010, antioxidant 1098, antioxidant 1076 or several, and additive amount is binary acid and two
The 0%~0.05% of first amine monomers gross mass;The uvioresistant additive is selected from salicylic acid esters, benzophenone class, benzotriazole,
Additive amount is the 0%~0.05% of binary acid and diamine monomer gross mass.
Wherein, in step 1), the additive amount of the deionized water be binary acid and diamine monomer gross mass 50%~
300%;The inert gas is selected from one of nitrogen, carbon dioxide, argon gas;It is described to crush as polymerizate to be ground into
The particle of 0.5mm~3.0mm or so size;The drying is with vacuum drying oven, and 80~105 DEG C of temperature, the time is 12~for 24 hours.
Compared with prior art, the present invention having the following beneficial effects:
1) binary acid of the invention by the way that specific fragrant hexichol ether structure will be contained or two containing specific fragrant hexichol ether structure
First amine is reacted with aliphatic or aromatic diamine or aliphatic or aromatic acid, is realized fragrant hexichol ether structure
It is introduced into nylon molecules chain, the flexibility and fluidity of molten for the high temperature resistant nylon being prepared are significantly improved.
2) preparation method of the invention does solvent, the postprocessing working procedures of solvent-free recycling with water, and processing step is simple, mentions
High production efficiency reduces production cost, is suitble to large-scale mass production.
Specific embodiment
Further illustrate that the present invention, following embodiment are the specific embodiment party of the present invention below by specific embodiment
Formula, but embodiments of the present invention are not limited by following embodiments.
The test method of each performance indicator is as follows:
Table 1
Performance project | Testing standard |
Melt index g/10min | ISO 1133 |
Tensile strength/MPa | ISO 527-1/-2 |
Elongation at break/% | ISO 527-1/-2 |
Bending strength/MPa | ISO 178 |
Notch impact strength kJ/m2 | ISO 180/1A |
Fusing point/DEG C | ISO 11357-1 |
Embodiment 1:
Polymerization reaction: precise molar ratio is that the decanedioic acid of 1:1.01 and the total 15KG of bisphenol A-type diphenyldiamine are added to band
In the reaction kettle of stirring, it is sequentially added end-capping reagent benzoic acid 14g, sodium hypophosphite 15g and deionized water 30L, is replaced with nitrogen
Gas reactor 5 times, emptying is filled with 0.05~0.2MPa of nitrogen, opens heating, is raised to reactor temperature in 1.5~2h
180 DEG C, stirring is opened when reactor temperature is at 100 DEG C, stablizing mixing speed is 50r/min.Equilibrium temperature at 180 DEG C,
Pressure 1.1MPa or so reacts 2h in kettle, after temperature in the kettle is increased to 230 DEG C, steady pressure 2.8MPa in 1h, react 2h,
It is subsequent slowly to deflate, it in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure, the reaction was continued 2h, rear discharging.Product
After crushing, 80 DEG C of vacuum drying oven processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 10KG, is put into rotary drum, is warming up to 250 DEG C, reaction time 15h
Afterwards, it discharges, obtains poly- decanedioyl bisphenol A-type diphenyldiamine;Each performance of the poly- decanedioyl bisphenol A-type diphenyldiamine of gained refers to
Mapping test result is as shown in table 2.
Embodiment 2:
Polymerization reaction: precise molar ratio is that the adipic acid of 1:1.02 and the total 15KG of bisphenol S type diphenyldiamine are added to band
In the reaction kettle of stirring, it is sequentially added end-capping reagent benzoic acid 28g, sodium hypophosphite 30g and deionized water 30L, uses carbon dioxide
Displacement gas reactor 5 times, emptying, is filled with 0.05~0.2MPa of carbon dioxide, opens heating, make reactor temperature 1.5~
It is raised to 160 DEG C in 2h, stirring is opened when reactor temperature is at 100 DEG C, stablizing mixing speed is 45r/min.Equilibrium temperature
At 160 DEG C, in kettle pressure 0.7MPa or so react 2h, after temperature in the kettle is increased to 240 DEG C in 1h, steady pressure
3.3MPa reacts 2h, then slowly deflates, and in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure, the reaction was continued
1h, it is rear to discharge.After product crushes, 80 DEG C of vacuum drying oven processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 10KG, is put into rotary drum, is warming up to 260 DEG C, reaction time 13h
Afterwards, processing obtains poly hexamethylene adipamide bisphenol S type diphenyldiamine;The poly- paraphenylene terephthalamide's '-biphenyl diphenol type diphenyldiamine of gained it is each
The results are shown in Table 2 for testing performance index.
Embodiment 3:
Polymerization reaction: the '-biphenyl diphenol type diphenyldiamine of the azelaic acid acid and 18.4KG that weigh 9.4KG is added in reaction kettle,
It is sequentially added end-capping reagent benzoic acid 30g, sodium hypophosphite 13.5g and deionized water 17L, with argon gas displacement gas reactor 5 times, row
Sky is filled with 0.05~0.2MPa of argon gas, opens heating, so that reactor temperature is raised to 180 DEG C in 1.5~2h, work as reaction kettle
Interior temperature opens stirring at 100 DEG C, and stablizing mixing speed is 50r/min.Equilibrium temperature is at 180 DEG C, pressure 1.1MPa in kettle
Left and right reaction 2h, after temperature in the kettle is increased to 230 DEG C, steady pressure 2.8MPa in 1h, react 2h, then slowly deflate,
It in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure, the reaction was continued 2h, rear discharging.After product crushes, vacuum is dried
80 DEG C of case processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 25KG, is put into rotary drum, is warming up to 250 DEG C, reaction time 15h
Afterwards, it discharges, obtains poly- nonanedioyl '-biphenyl diphenol type diphenyldiamine;The poly- nonanedioyl '-biphenyl diphenol type diphenyldiamine of gained it is each
The results are shown in Table 2 for testing performance index.
Embodiment 4:
Polymerization reaction: the hydroquinone type diphenyldiamine of the dodecanedioic acid and 13.09KG that weigh 9.9KG is added to reaction kettle
In, it is sequentially added end-capping reagent benzoic acid 60g, sodium hypophosphite 25g and deionized water 27L, with nitrogen displacement gas reactor 5 times,
Emptying is filled with 0.05~0.2MPa of nitrogen, opens heating, so that reactor temperature is raised to 140 DEG C in 1.0~1.5h, when anti-
Temperature in the kettle is answered to open stirring at 100 DEG C, stablizing mixing speed is 50r/min.Equilibrium temperature is at 140 DEG C, pressure in kettle
0.4MPa or so reacts 2h, after temperature in the kettle is increased to 250 DEG C, steady pressure 4.0MPa in 1.5h, react 2h, it is then slow
Slow play gas is put in the case where the unobvious decline of guarantee temperature in the kettle to normal pressure, the reaction was continued 2h, rear discharging.Product crushes
Afterwards, 80 DEG C of vacuum drying oven processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 20KG, is put into rotary drum, is warming up to 270 DEG C, reaction time 10h
Afterwards, it discharges, obtains poly- two acyl hydroquinone type diphenyldiamine of dodecane;The poly- two acyl hydroquinone type diphenyl ether of dodecane of gained
The results are shown in Table 2 for each testing performance index of diamines.
Embodiment 5:
Polymerization reaction: the decamethylene diamine of the resorcinol type diphenyl ether diacid and 10.1KG that weigh 17.8KG is added in reaction kettle,
It is sequentially added end-capping reagent benzoic acid 40g, sodium hypophosphite 13g and deionized water 40L, with nitrogen displacement gas reactor 5 times, row
Sky is filled with 0.05~0.2MPa of nitrogen, opens heating, so that reactor temperature is raised to 120 DEG C in 1.0~1.5h, work as reaction
Temperature in the kettle opens stirring at 100 DEG C, and stablizing mixing speed is 60r/min.Equilibrium temperature is at 120 DEG C, pressure in kettle
0.3MPa or so reacts 2h, after temperature in the kettle is increased to 250 DEG C, steady pressure 4.0MPa in 1.5~2h, react 2h, with
It slowly deflates, in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure afterwards, the reaction was continued 2h, rear discharging.Product powder
After broken, 80 DEG C of vacuum drying oven processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 20KG, is put into rotary drum, is warming up to 240 DEG C, reaction time 17h
Afterwards, it discharges, obtains poly- two acyl decamethylene diamine of resorcinol type diphenyl ether;The poly- two acyl decamethylene diamine of resorcinol type diphenyl ether of gained it is each
The results are shown in Table 2 for testing performance index.
Embodiment 6:
Polymerization reaction: precise molar ratio is that 1:1.05 '-biphenyl diphenol type diphenyl ether diacid and 12 carbon diamine 25KG are added
Into reaction kettle, it is sequentially added end-capping reagent benzoic acid 25g, sodium hypophosphite 20g and deionized water 30L, in nitrogen displacement kettle
Gas 5 times, emptying is filled with 0.05~0.2MPa of nitrogen, opens heating, reactor temperature is made to be raised to 180 in 1.0~1.5h
DEG C, stirring is opened when reactor temperature is at 100 DEG C, stablizing mixing speed is 60r/min.Equilibrium temperature is at 180 DEG C, in kettle
Pressure 1.1MPa or so reacts 2h, after temperature in the kettle is increased to 250 DEG C, steady pressure 4.0MPa in 1.5~2h, reaction
2h, it is subsequent slowly to deflate, it in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure, the reaction was continued 2h, rear discharging.
After product crushes, 80 DEG C of vacuum drying oven processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 20KG, is put into rotary drum, is warming up to 240 DEG C, reaction time 17h
Afterwards, it discharges, obtains poly- two acyl dodecamethylene diamine of '-biphenyl diphenol type diphenyl ether;The poly- two acyl dodecane of '-biphenyl diphenol type diphenyl ether of gained
The results are shown in Table 2 for each testing performance index of diamines.
Embodiment 7:
Polymerization reaction: the hexamethylene diamine of the bisphenol A-type diphenyl ether diacid and 5.7KG that weigh 23.4KG is added in reaction kettle, in succession
End-capping reagent benzoic acid 40g, sodium hypophosphite 13g and deionized water 40L is added, with nitrogen displacement gas reactor 5 times, emptying is filled
Enter 0.05~0.2MPa of nitrogen, open heating, reactor temperature is made to be raised to 180 DEG C in 1.0~1.5h, when warm in reaction kettle
Degree opens stirring at 100 DEG C, and stablizing mixing speed is 60r/min.Equilibrium temperature is at 180 DEG C, pressure 1.1MPa or so in kettle
React 2h, after temperature in the kettle is increased to 250 DEG C, steady pressure 4.0MPa in 1.5~2h, react 2h, then slowly deflate,
It in the case where the unobvious decline of guarantee temperature in the kettle, puts to normal pressure, the reaction was continued 2h, rear discharging.After product crushes, vacuum is dried
80 DEG C of case processing are for 24 hours, spare;
Thickening reaction: the product that polymerization reaction is obtained weighs 20KG, is put into rotary drum, is warming up to 250 DEG C, reaction time 14h
Afterwards, it discharges, obtains two acyl last of the ten Heavenly stems hexamethylene diamine of poly bisphenol type diphenyl ether;Each property of two acyl last of the ten Heavenly stems hexamethylene diamine of gained poly bisphenol type diphenyl ether
The results are shown in Table 2 for energy index test.
Comparative example 1:
The molar ratio of binary acid and diamine is 1:0.90, other are surveyed with embodiment 1, each performance indicator of gained high temperature resistant nylon
Test result is as shown in table 2.
Comparative example 2:
The molar ratio of binary acid and diamine is 1:1.20, other are surveyed with embodiment 1, each performance indicator of gained high temperature resistant nylon
Test result is as shown in table 2.
Table 2
Test item | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | Comparative example 1 | Comparative example 2 | Commercially available PA12T |
Relative viscosity | 2.3 | 2.1 | 2.1 | 2.0 | 1.9 | 2.0 | 2.1 | 1.2 | 1.2 | 2.3 |
Tensile strength/MPa | 76 | 93 | 82 | 66 | 70 | 68 | 90 | / | / | 72 |
Bending strength/MPa | 87 | 102 | 93 | 75 | 82 | 80 | 97 | / | / | 93 |
Notch impact strength kJ/m2 | 11 | 8.7 | 9.5 | 15 | 14.5 | 19 | 8.5 | / | / | 6.7 |
Fusing point/DEG C | 285 | 312 | 302 | 270 | 281 | 275 | 310 | 274 | 276 | 292 |
Elongation at break/% | 60 | 45 | 52 | 65 | 53 | 67 | 54 | / | / | 35 |
Melt index g/10min | 45 | 50 | 53 | 55 | 60 | 57 | 55 | / | / | 20 |
Claims (6)
1. a kind of high temperature resistant nylon, which is characterized in that structural formula are as follows:
Formulas I;
Or
Formula II;
Wherein, the R1It is selected from、、、、One or more of;
R2Selected from the aliphatic comprising 4~12 carbon atoms or aromatic alkyl.
2. a kind of preparation method of high temperature resistant nylon as described in claim 1, which comprises the steps of:
1) polymerization reaction: binary acid, diamine, reaction promoter, deionized water are proportionally added into reaction kettle, indifferent gas is used
Air in body displacement kettle, is filled with the inert gas of 0.05~0.2MPa, is warming up to 120 DEG C~180 DEG C, pressure is stablized 0.3
~1.1MPa reacts 1~2h, and temperature is then risen to 220 DEG C~260 DEG C, 1.5~4.8MPa of steady pressure, reacts 2h~6h
It slowly deflating, puts pressure in kettle to normal pressure afterwards in 1~2h, the reaction was continued 1~2h then discharges, and product crushes, drying,
It is spare;
2) thickening reaction: the polymeric reaction product of drying is added in rotary drum, and temperature is controlled at 240 DEG C~270 DEG C, is vacuumized
To -0.098MPa~-0.099Pa, 8h~16h is reacted, is discharged to get high temperature resistant nylon.
3. the preparation method of high temperature resistant nylon according to claim 2, which is characterized in that in step 1), the binary acid
Selected from including one of 4~12 fat of carbon atom races or aromatic diacid or several;And the diamine is selected from
Bisphenol A-type diphenyldiamine, bisphenol S type diphenyldiamine, '-biphenyl diphenol type diphenyldiamine, hydroquinone type diphenyl ether two
Amine, resorcinol type diphenyldiamine, two phenolic diphenyldiamine of more phenyl ring, polycyclic fragrant two phenolic diphenyldiamine, heterocycle
One of fragrant two phenolic diphenyldiamines are several;The molar ratio of the binary acid and diamine is 1:1~1:1.1,
Preferably 1:1.01~1:1.05.
4. the preparation method of high temperature resistant nylon according to claim 2, which is characterized in that in step 1), the diamine
Selected from including one of 4~12 fat of carbon atom races or aromatic diamine or several;And the binary acid is selected from
Bisphenol A-type diphenyl ether diacid, bisphenol S type diphenyl ether diacid, '-biphenyl diphenol type diphenyl ether diacid, hydroquinone type diphenyl ether two
Acid, resorcinol type diphenyl ether diacid, two phenolic diphenyl ether diacid of more phenyl ring, polycyclic fragrant two phenolic diphenyl ether diacid, heterocycle
One of fragrant two phenolic diphenyl ether diacid are several;The molar ratio of the binary acid and diamine is 1:1~1:1.1,
Preferably 1:1.01~1:1.05.
5. the preparation method of high temperature resistant nylon according to claim 2, which is characterized in that in step 1), the reaction is helped
Agent is selected from one of end-capping reagent, catalyst, antioxidant, uvioresistant additive or several;The end-capping reagent is selected from benzene first
One of acid, acetic acid, propionic acid or phthalic anhydride are several, and additive amount is the 0.5% of dicarboxylic acid monomer total mole number
~2%, preferably: 0.5%~1.5%;The catalyst be selected from sodium phosphate, calcium phosphate, sodium phosphite, Arizona bacilli, phosphorous acid magnesium,
One of zinc phosphite, sodium hypophosphite, Lime Hypophosphate, ortho phosphorous acid magnesium, ortho phosphorous acid zinc are several, and additive amount is
The 0.01%~0.05% of binary acid and diamine monomer gross mass;The antioxidant is selected from antioxidant 1010, antioxidant 1098, resists
One of oxygen agent 1076 is several, and additive amount is the 0%~0.05% of binary acid and diamine monomer gross mass;The anti-purple
Outside line additive is selected from salicylic acid esters, benzophenone class, benzotriazole, and additive amount is binary acid and diamine monomer gross mass
0%~0.05%.
6. the preparation method of high temperature resistant nylon according to claim 2, which is characterized in that in step 1), the deionization
The additive amount of water is the 50%~300% of binary acid and diamine monomer gross mass;The inert gas is selected from nitrogen, titanium dioxide
One of carbon, argon gas;Described crush is the particle that polymerizate is ground into 0.5mm~3.0mm or so size;The drying
For with vacuum drying oven, 80~140 DEG C of temperature, the time is 12~for 24 hours.
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CN111217996A (en) * | 2020-03-16 | 2020-06-02 | 珠海派锐尔新材料有限公司 | 4-arm star-shaped nylon and preparation method thereof |
CN116606433A (en) * | 2023-04-28 | 2023-08-18 | 湘潭大学 | Preparation method and application of heat-resistant transparent polyether amide |
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Cited By (4)
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CN110204459A (en) * | 2019-04-30 | 2019-09-06 | 珠海派锐尔新材料有限公司 | A kind of aromatic series diether dioctyl phthalate and preparation method thereof |
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CN116606433A (en) * | 2023-04-28 | 2023-08-18 | 湘潭大学 | Preparation method and application of heat-resistant transparent polyether amide |
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Application publication date: 20190514 |