CN108383998B - 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
- Publication number
- CN108383998B CN108383998B CN201810504788.8A CN201810504788A CN108383998B CN 108383998 B CN108383998 B CN 108383998B CN 201810504788 A CN201810504788 A CN 201810504788A CN 108383998 B CN108383998 B CN 108383998B
- Authority
- CN
- China
- Prior art keywords
- polyhydroxyamide
- reaction
- heated
- dimethyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
-
- 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
Abstract
The present invention relates to a kind of high-intensitive humidity response polyhydroxyamides and preparation method thereof.The preparation method of polyhydroxyamide is comprising steps of dissolve by heating and stir 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 heated sealed reactions 2~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 responsiveness 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-intensitive humidity response polyhydroxyamide
And preparation method thereof.
Background technique
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
One of important and most popular research field.Scientists have been prepared for various functionality polyamides 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 mainly passes through diacid or diacid halide compound and the condensation of 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
Preparation.
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 after absorbing moisture due to the presence of hydrophilic radical a large amount of in macromolecular structure
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.
Summary of the invention
In order to solve the above technical problem, the present invention provides a kind of high-intensitive humidity response polyhydroxyamide and its preparation sides
Method.
In order to achieve the object of the present invention, the invention adopts the following technical scheme:
A kind of high intensity humidity response polyhydroxyamide, the structural formula of the polyhydroxyamide are as follows:
Wherein, R is alkylidene, cycloalkylidene, alkenylene, sub- fragrance
Base, secondary hydroxyl, in ketone carbonyl a kind of group or a variety of groups combination；R1For methylene；N is integer, 10≤n≤1000.
Further, the structural formula of the polyhydroxyamide are as follows:
Further, the polyhydroxyamide breaking strength is 50~200MPa, and elongation at break is 1~80%；It is described poly-
After hydroxy amide water suction saturation, breaking strength is 20~60MPa, and elongation at break is 80~400%.
A kind of preparation method of the high-intensitive humidity response polyhydroxyamide, comprising the following steps:
Step 1, by 35~156 parts by weight dimethyl ester compounds and the alcohol ammoniac compounds of 28~87 parts by weight heating it is molten
It solves and stirs evenly to form reaction solution；
Be added 0.1~0.3 parts by weight basic catalyst in step 2, Xiang Suoshu 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 be any one of sodium methoxide solution, methanol potassium solution, alcohol sodium solution, it is described to urge
Agent concentration is 4.5~5.5mol/L.
Further, the dimethyl ester compound be dimethyl sebacate, it is dimethyl adipate, dimethyl malenate, right
Rutgers, repefral, cyclopropyl -1,1- dicarboxylic acid dimethyl ester, 1,4- cyclohexyl dicarboxylic acid dimethyl ester,
1,4- cyclohexanedione -2,5- dicarboxylic acid dimethyl ester, 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 responsiveness 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 breaking strength is
50~200MPa, elongation at break are 1~80%；After the polyhydroxyamide water suction saturation, breaking strength is 20~60MPa,
Elongation at break is 80~400%.
(4) polyhydroxyamide of the present invention is not needing addition solvent by dimethyl ester compound and alcohol ammoniac compounds
In the case where synthesize and obtain, synthetic method is simple, no pollution to the environment, and product does not need clarification, and recycling is easy.
The chemical equation of dimethyl ester compound and alcohol ammoniac compounds of the present invention 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 oxidized；High-temperature heating gradually increases molecular weight of product, and performance is more preferable.
Detailed description of the invention
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 polyhydroxyamide to thermodynamic property.
Influence of 1 moisture absorption of Fig. 5 polyhydroxyamide to mechanical performance.
Fig. 6 shows the infrared spectrum of polyhydroxyamide 2.
Fig. 7 shows the load-deformation curve of polyhydroxyamide 2.
Specific embodiment
More specific detail is made to technical solution of the present invention below with reference to embodiment:
The preparation of 1 polyhydroxyamide 1 of embodiment
It prepares polyhydroxyamide 1 as follows: taking dimethyl sebacate 9.5g, 1,3-diamino-2-propanol 3.7g is mixed at 70 DEG C
It closes uniformly, 250 μ L sodium methoxide solutions (concentration 5mol/L) is added, seal 70 DEG C of heating 12h.Water pump is vacuumized and is heated to
100 DEG C of reaction 2h to reaction system no liquid exist (since reaction raw materials are liquid, byproduct of reaction methanol is also liquid,
But target product is at this moment solid under the conditions of temperature), water pump is changed to oil pump and vacuumizes and be heated to 150 DEG C of reaction 1h,
Last 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
It prepares polyhydroxyamide 2 as follows: taking dimethyl adipate 3.5g, 1,3-diamino-2-propanol 1.9g is mixed at 70 DEG C
It closes uniformly, 130 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
0.9h, last oil 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
It prepares polyhydroxyamide 3 as follows: taking dimethyl malenate 13.5g, 1,3-diamino-2-propanol 9.3g is mixed at 70 DEG C
It closes uniformly, 650 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 1h exist to reaction system no liquid, and water pump is changed to oil pump and 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
It prepares polyhydroxyamide 4 as follows: taking dimethyl terephthalate (DMT) 5.9g, 1,3-diamino-2-propanol 2.8g is 70
DEG C be uniformly mixed, be added 190 μ L sodium methoxide solutions (concentration 5mol/L), seal 70 DEG C of heating 10h.Water pump is vacuumized and is heated
Exist to 100 DEG C of reaction 1.5h to reaction system no liquid, water pump is changed to oil pump and vacuumizes and be heated to 150 DEG C and is reacted
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
It prepares polyhydroxyamide 5 as follows: taking Isosorbide-5-Nitrae-cyclohexyl dicarboxylic acid dimethyl ester 6.0g, 1,3-diamino-2-propanol 5.6g
It is uniformly mixed at 70 DEG C, 360 μ L sodium methoxide solutions (concentration 5mol/L) is added, seal 70 DEG C of heating 12h.Water pump vacuumizes simultaneously
It is heated to 100 DEG C of reaction 2h to exist to reaction system no liquid, water pump is changed to oil pump and vacuumizes and be heated to 150 DEG C and is reacted
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
It prepares polyhydroxyamide 6 as follows: taking methylmalonic acid dimethyl ester 14.6g, 1,3-diamino-2-propanol 9.3g is 70
DEG C be uniformly mixed, be added 600 μ L sodium methoxide solutions (concentration 5mol/L), seal 70 DEG C of 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
It prepares polyhydroxyamide 7 as follows: taking dimethyl tartrate 17.2g, 1,3-diamino-2-propanol 9.3g is mixed at 68 DEG C
It closes uniformly, 600 μ L sodium methoxide solutions (concentration 5mol/L) is added, seal 68 DEG C of heating 2h.Water pump vacuumizes and is heated to 95
DEG C reaction 1h exists to reaction system no liquid, and water pump is changed to oil pump and vacuumizes and is heated to 145 DEG C of 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
It prepares polyhydroxyamide 8 as follows: taking 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 is changed to oil pump and vacuumizes and heats
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
It prepares polyhydroxyamide 9 as follows: taking furandicarboxylic acid dimethyl ester 11.0g, 1,3-diamino-2-propanol 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 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
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
It prepares polyhydroxyamide 10 as follows: taking 1,3- dimethyl acetone-1,3-dicarboxylate 17.4g, 1,3-diamino-2-propanol
9.1g is uniformly mixed at 70 DEG C, and 700 μ L sodium methoxide solutions (concentration 5.5mol/L) are added, and seals 70 DEG C of heating for 24 hours.Water receiving pumping
Vacuum is simultaneously heated to 100 DEG C of reaction 2h and exists to reaction system no liquid, and water pump is changed to oil pump and vacuumizes and is heated to 150
DEG C reaction 3h, 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
It prepares polyhydroxyamide 10 as follows: allyl malonic acid dimethyl ester 3.5g, 1,3-diamino-2-propanol 1.8g being taken to exist
75 DEG C are uniformly mixed, and 150 μ L sodium methoxide solutions (concentration 5.5mol/L) are added, 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 following are the tests that extension test is carried out after the polyhydroxyamide water absorption test and water suction:
The batten (structure of the batten is as shown in Figure 1) with a thickness of 0.2mm is taken to place 70 DEG C of bakings in a vacuum drying oven
It weighs after dry, is denoted as G0.Batten is placed in climatic chamber after weighing, maintaining the temperature inside the box is 20 DEG C, humidity 65%, often
Batten weighing is taken out after a period of time, 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
The glass transition temperature for increasing polyhydroxyamide reduces, and thermodynamic property changes, and indicates that material is opposite and softens, mechanical performance will
It changes.
Batten tensile property is tested by GB/T 1040.3-2006 after moisture absorption, rate of extension 1mm/min, in constant temperature and humidity
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 (6)
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 be alkylidene, it is cycloalkylidene, alkenylene, arylene, secondary
The combination of a kind of group or a variety of groups in hydroxyl, ketone carbonyl；R1For methylene；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 are as follows:
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, breaking strength is 20~
60MPa, elongation at break are 80~400%.
4. a kind of preparation method of high-intensitive humidity response polyhydroxyamide as claimed in any one of claims 1 to 3, feature
Be the following steps are included:
Step 1 dissolves by heating 35~156 parts by weight dimethyl ester compounds and the alcohol ammoniac compounds of 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 in step 2, Xiang Suoshu reaction solution
~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.
The dimethyl ester compound is the compound that two ends of chain are methyl esters group, the knot of the dimethyl ester compound
Structure formula isThe alcohol ammoniac compounds are that two ends of chain are amino and the compound containing hydroxyl, institute
The structural formula for stating alcohol ammoniac compounds is
5. 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.
6. 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- dicarboxylic acid dimethyl ester, 1,4- cyclohexyl dicarboxylic acid dimethyl ester, 1,4- cyclohexanedione -2,5- dioctyl phthalate
Dimethyl ester, methylmalonic acid dimethyl ester, diethyl malonic acid dimethyl ester, dimethyl tartrate, any in apple dimethyl phthalate
Kind；The alcohol ammoniac compounds are 1,3-diamino-2-propanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810504788.8A CN108383998B (en) | 2018-05-24 | 2018-05-24 | A kind of high intensity humidity response polyhydroxyamide and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810504788.8A CN108383998B (en) | 2018-05-24 | 2018-05-24 | A kind of high intensity humidity response polyhydroxyamide and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108383998A CN108383998A (en) | 2018-08-10 |
| CN108383998B true CN108383998B (en) | 2019-10-08 |
Family
ID=63071349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810504788.8A Active CN108383998B (en) | 2018-05-24 | 2018-05-24 | A kind of high intensity humidity response polyhydroxyamide and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108383998B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112920403B (en) * | 2021-01-26 | 2022-03-11 | 安徽农业大学 | Process for preparing reprocessable thermosetting polyesteramides, and the resulting thermosetting polyesteramides |
| CN113527875B (en) * | 2021-08-23 | 2022-05-13 | 安徽农业大学 | Bio-based nylon composite material and preparation method thereof |
| CN113651956B (en) * | 2021-08-23 | 2022-09-16 | 安徽农业大学 | Preparation method of ultrahigh-toughness branched polyamide copolymer and prepared polyamide copolymer |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2159637A4 (en) * | 2007-06-05 | 2011-12-21 | Nissan Chemical Ind Ltd | Positive photosensitive resin composition and polyhydroxyamide resin |
| JP6904332B2 (en) * | 2016-03-22 | 2021-07-14 | 日産化学株式会社 | Organic electroluminescence device |
| CN107501116B (en) * | 2017-09-14 | 2020-05-19 | 安徽农业大学 | Functional polyamide monomer, functional polyamide and preparation method |
-
2018
- 2018-05-24 CN CN201810504788.8A patent/CN108383998B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN108383998A (en) | 2018-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108383998B (en) | A kind of high intensity humidity response polyhydroxyamide and preparation method thereof | |
| Ali et al. | Syntheses of high-performance biopolyamides derived from itaconic acid and their environmental corrosion | |
| CN102898650B (en) | MTQ silicon resin with T-chain unit containing phenyl and preparation method thereof | |
| CN105646876B (en) | A kind of method that organic catalysis prepares polyesteramide | |
| CN108219457B (en) | Preparation method of colorless transparent norbornene structure-containing polyimide film | |
| CN103012798A (en) | Preparation method of methyl phenyl vinyl silicone resin | |
| CN101412566B (en) | Green environment-protective scale inhibitor and use thereof | |
| CN102127173B (en) | High-polymer ultraviolet light initiator and preparation method thereof | |
| CN104448714B (en) | Organic fluorine random copolymer modified epoxy material for packaging LEDs and preparation method of organic fluorine random copolymer modified epoxy material | |
| JP2019143026A (en) | Liquid organosilicon compound and thermosetting resin composition containing the same | |
| Breslow et al. | The synthesis and polymerization of ethylenesulfonic acid | |
| CN106566193A (en) | Fluorine and silicon-containing epoxy polymer modified alicyclic epoxy LED composite packaging material and preparation method thereof | |
| KR20200124670A (en) | Polyimide resin, polyimide varnish and polyimide film | |
| CN111732748B (en) | Cross-linked colorless transparent high-temperature-resistant polyimide film material and preparation method thereof | |
| CN110054731B (en) | Preparation method of reversible acid-base discoloration maleimide copolymer | |
| CN115260929A (en) | Hydrophobic self-adhesive cellulose-based transparent adhesive tape and synthesis method thereof | |
| JPH0465429A (en) | Polysilethylene siloxane | |
| Rejaibi et al. | Synthesis and physicochemical properties of new fatty (co) polyamides as potential UV powder coating | |
| CN1230462C (en) | Prepn of phenyl and methyl sesquisiloxane prepolymer | |
| CN1027816C (en) | Process for preparing copolyamide-imide having thermostability and groups of diorganopolysiloxane | |
| CN106750198A (en) | A kind of thermotropic liquid crystalline polyester of monomer ratio stabilization with and preparation method and application | |
| CN106633074A (en) | Polysiloxane with electrochromic property and preparation method thereof | |
| JP2018048289A (en) | Liquid crystal material, liquid crystal film and production method of the same, sensor, and optical element | |
| CN112225712B (en) | Epoxidized soybean oil propylene pimaric acid ester and preparation method and application thereof | |
| JPH0465428A (en) | Polysilethylene siloxane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |