CN108383998A - A kind of high intensity humidity response polyhydroxyamide and preparation method thereof - Google Patents
A kind of high intensity humidity response polyhydroxyamide and preparation method thereof Download PDFInfo
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- CN108383998A CN108383998A CN201810504788.8A CN201810504788A CN108383998A CN 108383998 A CN108383998 A CN 108383998A CN 201810504788 A CN201810504788 A CN 201810504788A CN 108383998 A CN108383998 A CN 108383998A
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
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Abstract
The present invention relates to a kind of high intensity humidity to respond polyhydroxyamide and preparation method thereof.The preparation method of polyhydroxyamide includes step：It dissolves by heating and stirs evenly dimethyl ester compound and alcohol ammoniac compounds to form reaction solution；It is added basic catalyst into reaction solution, 68~72 DEG C of reactions 2 of heated sealed~for 24 hours；Then reaction system is heated to 95~105 DEG C, water pump vacuumizes reaction 1~3 hour；Again by reaction system to 145~155 DEG C, oil pump vacuumizes reaction 0.5~1.5 hour；Reaction system is finally heated to 210~230 DEG C, oil pump vacuumizes reaction 0.5~1.5 hour, obtains polyhydroxyamide.The polyhydroxyamide that the present invention prepares has humidity response while the high-intensity performance for possessing polyamide, and toughness increases substantially after absorbing water, so that polyhydroxyamide has wider application prospect in terms of functional material.
Description
Technical field
The invention belongs to functionality polyamide Material Fields, are specifically related to a kind of high intensity humidity response polyhydroxyamide
And preparation method thereof.
Background technology
Polyamide is the macromolecule with recurring amide radical group on strand, is commonly called as nylon.Since it is with excellent heat
Performance and mechanical performance, the every field being widely used in life.With the development of science and technology functionality polyamide becomes most
Important and most popular one of research field.Scientists have been prepared for various functions polyamide at present, such as：Fragrant adoption
Amide, Flameproof polyamide, ultrabranching polyamide, soluble polyamide, polyamide-imide, the high molecular materials such as polyhydroxyamide.
Wherein polyhydroxyamide receives extensive research due to unique performance.
Currently, the preparation of polyhydroxyamide is mainly condensed by diacid or diacid halide compound and the diamines containing hydroxyl
Polymerization obtains.But it since esterification also easily occurs for hydroxyl and carboxyl or acyl halide group, is caused to the preparation of polyhydroxyamide
Great difficulty.Phenolic hydroxyl group is not easy to be applied to prepare fragrant adoption hydroxyl with carboxyl or acyl halide group generation esterification
Amide.Polyhydroxyamide is prepared by the aromatic diamine polymerization containing hydroxyl on diacid or diacid halide compound and phenyl ring
Method breaches the influence of carboxyl and carboxylic acid halides to hydroxyl to a certain extent.However, up to the present, the preparation of polyhydroxyamide
It is also only limitted to aromatic series, and type is seldom, significantly limits the extensive use of polyhydroxyamide.Secondly because aromatic group
In the presence of easily cyclisation forms oxazole in case of heating for phenolic hydroxyl group and amide group, largely limits polyhydroxyamide
It prepares.
Functional material becomes the research hotspot of Material Field, and wherein humidity responsive materials are received due to unique performance
Favor extensively.Humidity responsive materials lead to light due to the presence of a large amount of hydrophilic radical in macromolecular structure after absorbing moisture
Performance, thermodynamic property, electric conductivity, mechanical performance change.Due to the particularity of humidity responsive materials, answered extensively
Used in capacitance resistance field and sensory field.Current humidity responsive materials number of species are various, but most in absorption moisture
Mechanical performance generally reduces afterwards.
Invention content
In order to solve the above technical problem, the present invention provides a kind of high intensity humidity response polyhydroxyamide and its preparation sides
Method.
In order to achieve the object of the present invention, present invention employs following technical schemes：
A kind of high intensity humidity response polyhydroxyamide, the structural formula of the polyhydroxyamide are as follows：
Wherein, R be alkyl, naphthenic base, alkenyl, cycloalkenyl group, aromatic radical,
The combination of a kind of group or a variety of groups in hydroxyl, carbonyl；R1For a kind of group or a variety of groups in alkyl, alkenyl, aromatic radical
Combination；N is integer, 10≤n≤1000.
Further, the structural formula of the polyhydroxyamide is：
Further, the polyhydroxyamide fracture strength is 50~200MPa, and elongation at break is 1~80%；It is described poly-
After hydroxy amide water suction saturation, fracture strength is 20~60MPa, and elongation at break is 80~400%.
A kind of preparation method of the high intensity humidity response polyhydroxyamide, includes the following steps：
Step 1, by the alcohol ammoniac compounds of 35~156 parts by weight dimethyl ester compounds and 28~87 parts by weight heat it is molten
It solves and stirs evenly to form reaction solution；
Step 2 is added 0.1~0.3 parts by weight basic catalyst into the reaction solution, heated sealed to 68~72 DEG C it is anti-
Answer 2~for 24 hours；
Reaction solution described in step 2 is heated to 95~105 DEG C by step 3, and water pump vacuumizes reaction 1~3 hour；
Reaction solution described in step 3 is heated to 145~155 DEG C by step 4, and oil pump vacuumizes reaction 0.5~1.5 hour；
Reaction solution described in step 4 is heated to 210~230 DEG C by step 5, and oil pump vacuumizes reaction 0.5~1.5 hour,
Obtain polyhydroxyamide.
Further, the dimethyl ester compound is the compound that two ends of chain are methyl esters group, the dimethyl ester
The structural formula of class compound isThe alcohol ammoniac compounds are that two ends of chain are amino and contain hydroxyl
The structural formula of the compound of base, the alcohol ammoniac compounds is
Further, the catalyst is sodium methoxide solution, methanol potassium solution, any one of alcohol sodium solution, described to urge
A concentration of 4.5~5.5mol/L of agent.
Further, the dimethyl ester compound be dimethyl sebacate, it is dimethyl adipate, dimethyl malenate, right
Rutgers, repefral, cyclopropyl -1,1- diformate mono methyl esters, 1,4- cyclohexyl dicarboxylic acids dimethyl ester,
1,4- cyclohexanedione -2,5- dicarboxylic acid dimethyl esters, methylmalonic acid dimethyl ester, diethyl malonic acid dimethyl ester, tartaric acid diformazan
Any one of ester, apple dimethyl phthalate, furandicarboxylic acid dimethyl ester；The alcohol ammoniac compounds are 1,3 diamino -2- third
Alcohol.
The beneficial effects of the present invention are：
(1) present invention prepares polyhydroxyamide by melt condensation polymerization, and amido bond and hydroxyl, which exist simultaneously, makes poly- hydroxyl
Amide has humidity response while the high-intensity performance for possessing polyamide, and toughness increases substantially after absorbing water, greatly
Application and application surface are improved greatly, so that before polyhydroxyamide has widely application in terms of the functional material
Scape.
(2) significant changes can occur polyhydroxyamide material of the present invention for mechanical performance after moisture absorption in air, more into
One step shows the increase of tensile toughness.Polyhydroxyamide moisture absorption post-tensioning intensity of the present invention is slow as humidity exposure time increases
It is slow to reduce, and elongation at break then sharply increases relatively, toughness dramatically increases.
(3) polyhydroxyamide material mechanical parameters of the present invention are as follows：The polyhydroxyamide fracture strength is
50~200MPa, elongation at break are 1~80%；After the polyhydroxyamide water suction saturation, fracture strength is 20~60MPa,
Elongation at break is 80~400%.
(4) polyhydroxyamide of the present invention need not add solvent by dimethyl ester compound and alcohol ammoniac compounds
In the case of synthesize and obtain, synthetic method is simple, environmentally safe, and product does not need clarification, and recycling is easy.
The chemical equation of dimethyl ester compound of the present invention and alcohol ammoniac compounds is as follows：
The effect that water pump of the present invention vacuumizes is the impurity removed in reaction system；The effect that oil pump vacuumizes is to prevent instead
System is answered to be aoxidized；High-temperature heating makes molecular weight of product gradually increase, and performance is more preferable.
Description of the drawings
Fig. 1 is the structural schematic diagram of batten.
Fig. 2 shows the infrared spectrum of polyhydroxyamide 1.
Fig. 3 shows the when m- hydroscopicity curve of polyhydroxyamide 1.
Influence of 1 moisture absorption of Fig. 4 polyhydroxyamides to thermodynamic property.
Influence of 1 moisture absorption of Fig. 5 polyhydroxyamides to mechanical performance.
Fig. 6 shows the infrared spectrum of polyhydroxyamide 2.
Fig. 7 shows the load-deformation curve of polyhydroxyamide 2.
Specific implementation mode
More specific detail is made to technical solution of the present invention with reference to embodiment：
The preparation of 1 polyhydroxyamide 1 of embodiment
Prepare polyhydroxyamide 1 as follows：Dimethyl sebacate 9.5g, 1,3 diamino -2- propyl alcohol 3.7g is taken to be mixed at 70 DEG C
Uniformly, 250 μ L sodium methoxide solutions (concentration 5mol/L) are added, seal 70 DEG C of heating 12h.Water pump vacuumizes and is heated to 100
DEG C reaction 2h has that (since reaction raw materials are liquid, byproduct of reaction methanol is also liquid, but mesh to reaction system no liquid
It is at this moment solid under temperature condition to mark product), water pump is changed to oil pump and vacuumizes and is heated to 150 DEG C of reaction 1h, finally
Oil pump, which vacuumizes, is heated to 220 DEG C of reaction 1h.After reaction, product taking-up is sealed.
As shown in Figure 2：Raw material dimethyl sebacate of the present invention according to embodiment 1 after reacting, and ester group peak disappears substantially, newly
The peak of amide group is generated, representative is reacted successfully, and ester is substantially transitioned to amide group.Simultaneously there are still hydroxyl, indicate that hydroxyl exists
It is not reacted in reaction process namely polyhydroxyamide is successfully prepared in the present invention.
The preparation of 2 polyhydroxyamide 2 of embodiment
Prepare polyhydroxyamide 2 as follows：Dimethyl adipate 3.5g, 1,3 diamino -2- propyl alcohol 1.9g is taken to be mixed at 70 DEG C
Uniformly, 130 μ L sodium methoxide solutions (concentration 5mol/L) are added, seal 70 DEG C of heating 10h.Water pump vacuumizes and is heated to 100
DEG C reaction 1.5h to reaction system no liquid exist, by water pump be changed to oil pump vacuumize and be heated to 150 DEG C reaction 0.9h, most
Rear pump or output pump, which vacuumizes, is heated to 220 DEG C of reaction 0.8h.After reaction, product taking-up is sealed.
As shown in Figure 6：Raw material dimethyl adipate of the present invention according to embodiment 2 after reacting, and ester group peak disappears substantially, newly
The peak of amide group is generated, representative is reacted successfully, and ester is substantially transitioned to amide group.Simultaneously there are still hydroxyl, indicate that hydroxyl exists
It is not reacted in reaction process namely polyhydroxyamide is successfully prepared in the present invention.
The preparation of 3 polyhydroxyamide 3 of embodiment
Prepare polyhydroxyamide 3 as follows：Dimethyl malenate 13.5g, 1,3 diamino -2- propyl alcohol 9.3g is taken to be mixed at 70 DEG C
Uniform, 650 μ L sodium methoxide solutions (concentration 5mol/L) of addition are closed, 70 DEG C of heating 10h are sealed.Water pump is vacuumized and is heated to
100 DEG C of reaction 1h exist to reaction system no liquid, and water pump, which is changed to oil pump, vacuumizes and be heated to 150 DEG C of reaction 0.8h,
Last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 1h.After reaction, product taking-up is sealed.
The preparation of 4 polyhydroxyamide 4 of embodiment
Prepare polyhydroxyamide 4 as follows：Dimethyl terephthalate (DMT) 5.9g is taken, 1,3 diamino -2- propyl alcohol 2.8g is at 70 DEG C
It is uniformly mixed, 190 μ L sodium methoxide solutions (concentration 5mol/L) is added, seal 70 DEG C of heating 10h.Water pump is vacuumized and is heated to
100 DEG C of reaction 1.5h exist to reaction system no liquid, are changed to oil pump and vacuumize and be heated to 150 DEG C water pump and react
0.5h, last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 0.8h.After reaction, reactant taking-up is sealed.
The preparation of 5 polyhydroxyamide 5 of embodiment
Prepare polyhydroxyamide 5 as follows：Isosorbide-5-Nitrae-cyclohexyl dicarboxylic acid dimethyl ester 6.0g, 1,3 diamino -2- propyl alcohol 5.6g is taken to exist
70 DEG C are uniformly mixed, and 360 μ L sodium methoxide solutions (concentration 5mol/L) are added, and seal 70 DEG C of heating 12h.Water pump vacuumizes and adds
Heat exists to 100 DEG C of reaction 2h to reaction system no liquid, is changed to oil pump and vacuumizes and be heated to 150 DEG C water pump and react
0.7h, last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 1h.After reaction, product taking-up is sealed.
The preparation of 6 polyhydroxyamide 6 of embodiment
Prepare polyhydroxyamide 6 as follows：Methylmalonic acid dimethyl ester 14.6g is taken, 1,3 diamino -2- propyl alcohol 9.3g is 70
DEG C be uniformly mixed, be added 600 μ L sodium methoxide solutions (concentration 5mol/L), seal 70 DEG C heating 11.5h.Water pump vacuumizes and adds
Heat exists to 100 DEG C of reaction 2h to reaction system no liquid, is changed to oil pump and vacuumizes and be heated to 150 DEG C water pump and react
1h, last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 1h.After reaction, product taking-up is sealed.
The preparation of 7 polyhydroxyamide 7 of embodiment
Prepare polyhydroxyamide 7 as follows：Dimethyl tartrate 17.2g, 1,3 diamino -2- propyl alcohol 9.3g is taken to be mixed at 68 DEG C
Uniform, 600 μ L sodium methoxide solutions (concentration 5mol/L) of addition are closed, 68 DEG C of heating 2h are sealed.Water pump vacuumizes and is heated to 95
DEG C reaction 1h to reaction system no liquid exist, by water pump be changed to oil pump vacuumize and be heated to 145 DEG C reaction 0.5h, finally
Oil pump, which vacuumizes, is heated to 210 DEG C of reaction 0.5h.After reaction, product taking-up is sealed.
The preparation of 8 polyhydroxyamide 8 of embodiment
Prepare polyhydroxyamide 8 as follows：Take Isosorbide-5-Nitrae-cyclohexanedione -2,5- dicarboxylic acid dimethyl ester 1.8g, 1,3 diamino -2-
Propyl alcohol 7.4g is uniformly mixed at 72 DEG C, and 100 μ L sodium methoxide solutions (concentration 5.5mol/L) are added, and seals 72 DEG C of heating for 24 hours.Water receiving
Pumping vacuum is simultaneously heated to 105 DEG C of reaction 3h and exists to reaction system no liquid, and water pump, which is changed to oil pump, to be vacuumized and heat
To 155 DEG C of reaction 5h, last oil pump, which vacuumizes, is heated to 230 DEG C of reaction 5h.After reaction, product taking-up is sealed.
The preparation of 9 polyhydroxyamide 9 of embodiment
Prepare polyhydroxyamide 9 as follows：Furandicarboxylic acid dimethyl ester 11.0g is taken, 1,3 diamino -2- propyl alcohol 5.4g is 70
DEG C be uniformly mixed, be added 300 μ L sodium methoxide solutions (concentration 4.5mol/L), seal 70 DEG C heating 12h.Water pump vacuumizes and adds
Heat exists to 100 DEG C of reaction 2h to reaction system no liquid, is changed to oil pump and vacuumizes and be heated to 150 DEG C water pump and react
3h, last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 3h.After reaction, product taking-up is sealed.
The preparation of 10 polyhydroxyamide 10 of embodiment
Prepare polyhydroxyamide 10 as follows：Take 1,3- dimethyl acetone-1,3-dicarboxylates 17.4g, 1,3 diamino -2- propyl alcohol 9.1g
It is uniformly mixed at 70 DEG C, 700 μ L sodium methoxide solutions (concentration 5.5mol/L) is added, seal 70 DEG C of heating for 24 hours.Water pump vacuumizes
And be heated to 100 DEG C of reaction 2h and exist to reaction system no liquid, by water pump be changed to oil pump vacuumize and be heated to 150 DEG C it is anti-
3h is answered, last oil pump, which vacuumizes, is heated to 220 DEG C of reaction 1.5h.After reaction, product taking-up is sealed.
The preparation of 10 polyhydroxyamide 10 of embodiment
Prepare polyhydroxyamide 10 as follows：Allyl malonic acid dimethyl ester 3.5g, 1,3 diamino -2- propyl alcohol 1.8g is taken to exist
75 DEG C are uniformly mixed, and 150 μ L sodium methoxide solutions (concentration 5.5mol/L) are added, and seal 75 DEG C of heating 22h.Water pump vacuumizes simultaneously
Be heated to 100 DEG C of reaction 1.5h and exist to reaction system no liquid, by water pump be changed to oil pump vacuumize and be heated to 155 DEG C it is anti-
2h is answered, last oil pump, which vacuumizes, is heated to 225 DEG C of reaction 1h.After reaction, product taking-up is sealed.
The experiment of progress extension test after being the polyhydroxyamide water absorption test below and absorbing water：
It is that the batten (structure of the batten is as shown in Figure 1) of 0.2mm is positioned over 70 DEG C of bakings in vacuum drying chamber to take thickness
It weighs after dry, is denoted as G0.Batten is positioned over climatic chamber after weighing, it is 20 DEG C to maintain the temperature inside the box, humidity 65%, often
Batten is taken out after a period of time to weigh, and is denoted as Gi, i=(1,2,3,4 ...), batten is still put back in constant-humidity constant-temperature case after weighing.
Water absorption rate (the W of batten is calculated as followsi)：
Wi=(Gi-G0)/G0 × 100%.
As shown in figure 3, the polyhydroxyamide of the preparation of present example 1 moisture absorption process in 65% environment, when with moisture absorption
Between increase water absorption rate increase, finally tend to balance.
As shown in figure 4, polyhydroxyamide prepared by present example 1 is in 65% environment after moisture absorption, with humidity exposure time
Increasing the glass transition temperature of polyhydroxyamide reduces, and thermodynamic property changes, and indicates that material is opposite and softens, mechanical performance will
It changes.
Batten tensile property is by GB/T 1040.3-2006 tests, rate of extension 1mm/min, in constant temperature and humidity after moisture absorption
Under the conditions of test.
As shown in Figure 5：Polyhydroxyamide prepared by present example 1 is in 65% environment after moisture absorption, with humidity exposure time
The mechanical property for increasing polyhydroxyamide changes, and the relatively small amplitude reduction of stress, strain increases considerably, and toughness promotes 60
Times or so.
As shown in Figure 7：Polyhydroxyamide prepared by present example 2 equally has high intensity.
It is found through experiment that：The polyhydroxyamide moisture absorption post-tensioning intensity that the present invention prepares is slow as humidity exposure time increases
It is slow to reduce, and elongation at break then sharply increases relatively, polyhydroxyamide toughness dramatically increases.
Claims (7)
1. a kind of high intensity humidity responds polyhydroxyamide, it is characterised in that：The structural formula of the polyhydroxyamide is as follows：
Wherein, R is alkyl, naphthenic base, alkenyl, cycloalkenyl group, aromatic radical, hydroxyl
The combination of a kind of group or a variety of groups in base, carbonyl；R1For a kind of group in alkyl, alkenyl, aromatic radical or a variety of groups
Combination；N is integer, 10≤n≤1000.
2. high intensity humidity as described in claim 1 responds polyhydroxyamide, it is characterised in that：The knot of the polyhydroxyamide
Structure formula is：
3. high intensity humidity as described in claim 1 responds polyhydroxyamide, it is characterised in that：The polyhydroxyamide fracture
Intensity is 50~200MPa, and elongation at break is 1~80%；After polyhydroxyamide water suction saturation, fracture strength is 20~
60MPa, elongation at break are 80~400%.
4. a kind of preparation method responding polyhydroxyamide such as claims 1 to 3 any one of them high intensity humidity, feature
It is to include the following steps：
Step 1 dissolves by heating the alcohol ammoniac compounds of 35~156 parts by weight dimethyl ester compounds and 28~87 parts by weight simultaneously
It stirs evenly to form reaction solution；
0.1~0.3 parts by weight basic catalyst, heated sealed to 68~72 DEG C of reactions 2 are added into the reaction solution for step 2
~for 24 hours；
Reaction solution described in step 2 is heated to 95~105 DEG C by step 3, and water pump vacuumizes reaction 1~3 hour；
Reaction solution described in step 3 is heated to 145~155 DEG C by step 4, and oil pump vacuumizes reaction 0.5~1.5 hour；
Reaction solution described in step 4 is heated to 210~230 DEG C by step 5, and oil pump vacuumizes reaction 0.5~1.5 hour, obtains
Polyhydroxyamide.
5. the preparation method of high intensity humidity response polyhydroxyamide as claimed in claim 4, it is characterised in that：The diformazan
Ester type compound is the compound that two ends of chain are methyl esters group, and the structural formula of the dimethyl ester compound isThe alcohol ammoniac compounds are that two ends of chain are amino and the compound containing hydroxyl, the alcohol ammonia
The structural formula of class compound is
6. the preparation method of high intensity humidity response polyhydroxyamide as claimed in claim 4, it is characterised in that：The catalysis
Agent is any one of sodium methoxide solution, methanol potassium solution, alcohol sodium solution, and the catalyst concn is 4.5~5.5mol/L.
7. the preparation method of high intensity humidity response polyhydroxyamide as claimed in claim 4, it is characterised in that：The diformazan
Ester type compound is dimethyl sebacate, dimethyl adipate, dimethyl malenate, dimethyl terephthalate (DMT), O-phthalic
Dimethyl phthalate, cyclopropyl -1,1- diformate mono methyl esters, 1,4- cyclohexyl dicarboxylic acids dimethyl ester, 1,4- cyclohexanedione -2,5- dioctyl phthalate
Dimethyl ester, methylmalonic acid dimethyl ester, diethyl malonic acid dimethyl ester, dimethyl tartrate, apple dimethyl phthalate, furans diformazan
Any one of dimethyl phthalate；The alcohol ammoniac compounds are 1,3 diamino -2- propyl alcohol.
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| CN112920403A (en) * | 2021-01-26 | 2021-06-08 | 安徽农业大学 | Process for preparing reprocessable thermosetting polyesteramides, and the resulting thermosetting polyesteramides |
| CN113527875A (en) * | 2021-08-23 | 2021-10-22 | 安徽农业大学 | Bio-based nylon composite material and preparation method thereof |
| CN113651956A (en) * | 2021-08-23 | 2021-11-16 | 安徽农业大学 | Preparation method of ultrahigh-toughness branched polyamide copolymer and prepared polyamide copolymer |
| CN115073728A (en) * | 2022-07-14 | 2022-09-20 | 江苏富琪森新材料有限公司 | Glass-like thermosetting resin and preparation method thereof |
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| CN101681099A (en) * | 2007-06-05 | 2010-03-24 | 日产化学工业株式会社 | Positive photosensitive resin composition and polyhydroxyamide resin |
| WO2017164129A1 (en) * | 2016-03-22 | 2017-09-28 | 日産化学工業株式会社 | Polyhydroxyamide composition for manufacturing substrate for electronic device, and polybenzoxazole resin film |
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| CN112920403A (en) * | 2021-01-26 | 2021-06-08 | 安徽农业大学 | Process for preparing reprocessable thermosetting polyesteramides, and the resulting thermosetting polyesteramides |
| CN113527875A (en) * | 2021-08-23 | 2021-10-22 | 安徽农业大学 | Bio-based nylon composite material and preparation method thereof |
| CN113651956A (en) * | 2021-08-23 | 2021-11-16 | 安徽农业大学 | Preparation method of ultrahigh-toughness branched polyamide copolymer and prepared polyamide copolymer |
| CN115073728A (en) * | 2022-07-14 | 2022-09-20 | 江苏富琪森新材料有限公司 | Glass-like thermosetting resin and preparation method thereof |
| CN115073728B (en) * | 2022-07-14 | 2023-12-05 | 江苏富琪森新材料有限公司 | Glass-like thermosetting resin and preparation method thereof |
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