CN104292459A - Preparation method of high-solid-content and low-viscosity polyimide material - Google Patents
Preparation method of high-solid-content and low-viscosity polyimide material Download PDFInfo
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- CN104292459A CN104292459A CN201410557628.1A CN201410557628A CN104292459A CN 104292459 A CN104292459 A CN 104292459A CN 201410557628 A CN201410557628 A CN 201410557628A CN 104292459 A CN104292459 A CN 104292459A
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Abstract
The invention relates to a preparation method of a high-solid-content and low-viscosity polyimide material. The preparation method comprises the following steps: dissolving aromatic diamine into a proper amount of organic solvent under protection of an inert gas, carrying out mechanical agitation, after aromatic diamine is completely dissolved, adding aromatic anhydride, a swelling binder and an end-capping reagent; and reacting at room temperature to obtain a polyamide acid solution, wherein the mass ratio of the aromatic diamine to the aromatic anhydride is (1:1) to (1:1.1). According to the preparation method, the polyamide acid solution of which the solid content is 30%-35% can be prepared; the viscosity range is 500-10,000cp; the preparation method is concise in reaction steps, and high in yield, which is close to 100%; and the polyimide film prepared by the method is excellent in mechanical property, thermal property, electric property and the like, and can be widely applied to microelectronics and other fields.
Description
Technical field
The present invention relates to polyimide material technical field, specifically, is the preparation method of a kind of high solids content, low viscosity polyimide prepolymer.
Background technology
Polyimide (polyimide, PI) refers to containing a base polymer of imide ring on main chain, is generally formed by aromatic diamines and fatty dianhydride or aromatic dianhydride polycondensation.Due to the resonant interaction of its half trapezoidal and trapezoidal backbone structure, aromatic ring, make it have outstanding thermostability, chemical stability, electrical insulating property and high physical strength, become the high performance material with widespread use.In addition, it also has the adhesivity good with substrate, and the feature such as the matching good with semiconductor technology, is therefore widely used in microelectronic in the last few years, as the insulation layer of microelectronic device, passivation layer or stress-buffer layer.
Due to the restriction of solubleness, the solid content of existing polyimide prepolymer solution, generally 10 ~ 20%, improves solid content further and can cause polymers soln gel.But numerous electron device user proposes the requirement of high thickness polyimide coating, therefore need that a kind of reactions steps is simple, solid content is high, viscosity is low, be suitable for the preparation method of industrialization badly.The invention provides and a kind ofly yet there are no the high solids content of report, the preparation method of low viscosity polyimide prepolymer.
Summary of the invention
The object of the invention is for deficiency of the prior art, the preparation method of a kind of high solids content, low viscosity polyimide prepolymer is provided.
For achieving the above object; the technical scheme that the present invention takes is: the preparation method of a kind of high solids content, low viscosity polyimide prepolymer; described preparation method comprises the following steps: under protection of inert gas; aromatic diamines is dissolved in organic solvent; mechanical stirring, after aromatic diamines all dissolves, adds aromatic diacid acid anhydride, adhesion promotor and end-capping reagent; at room temperature react to obtain polyamic acid solution, i.e. polyimide prepolymer.
Reaction system solid content is 30% ~ 35%.
System viscosity is 500 ~ 10000cp.
Described aromatic diamines and fragrant four dicarboxylic anhydride amount of substance ratios are 1:1 ~ 1:1.1.
Described adhesion promotor and the mol ratio of aromatic diamines are 1% ~ 10%.
Described end-capping reagent and aromatic dianhydride mol ratio are 1% ~ 20%.
Described aromatic diamines is selected from 4, 4 '-diaminodiphenyl oxide, 3, 4 '-diaminodiphenyl oxide, 3, 3 '-diaminodiphenyl oxide, 2, 3 '-diaminodiphenyl oxide, 2, 4 '-diaminodiphenyl oxide, 4, 4 '-diaminodiphenylmethane, 3, 4 '-diaminodiphenylmethane, 3, 3 '-diaminodiphenylmethane, 2, 3 '-diaminodiphenylmethane, 2, 4 '-diaminodiphenylmethane, 4, 4 '-diamino-3, 3 '-dimethyl diphenyl methane, 4, 4 '-diamino-3, 3 '-diethyl ditane, 4, 4 '-diamino-3, 3 '-dimethyl diphenyl, 1, two (the 4 '-amino phenolic group) benzene of 3-, 1, two (the 3 '-amino phenolic group) benzene of 3-, 1, two (the 4 '-amino phenolic group) benzene of 4-, 1, two (the 3 '-amino phenolic group) benzene of 4-, 4, 4 '-diaminobenzophenone, 3, 4 '-diaminobenzophenone, 3, 3 '-diaminobenzophenone, 2, 3 '-diaminobenzophenone, 2, the derivative of 4 '-diaminobenzophenone or above-mentioned aromatic diamines.
Described fragrance four dicarboxylic anhydride is selected from 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, pyromellitic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 4, the two Tetra hydro Phthalic anhydride, 3 of 4 '-oxygen, 4, the derivative of 3 ', 4 '-diphenyl sulfone dianhydride, 3,6-bis-(methoxyl group) benzene dianhydride, hexafluorodianhydride or above-mentioned fragrant four dicarboxylic anhydrides.
Described adhesion promotor is selected from 1,3 pairs of (3-aminopropyls)-1,1,3,3-tetramethyl disiloxane, 1,3 pairs of (3-aminopropyls)-1,1, the derivative of 3,3-tetraphenyl sily oxide, two (3-aminopropyl)-tetramethyl-polysiloxane, two (3-aminopropyl)-tetraphenyl polysiloxane or above-mentioned adhesion promotor.
Described end-capping reagent is selected from the derivative of maleic anhydride, cyanate, benzocyclobutene, maleimide, trifluoro-ethylene oxygen, acetylene, phenylacetylene, benzo maleimide, norbornylene imines, duplex benzene, cyano group or above-mentioned end-capping reagent.
Described organic solvent is selected from N-Methyl pyrrolidone, N,N-dimethylacetamide, DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF)/methyl alcohol, phenylformic acid or Whitfield's ointment.
The invention has the advantages that:
1, the present invention with aromatic tetrahydric dianhydride and aromatic diamines for raw material is polymerized, control the relative proportion of aromatic tetrahydric dianhydride and aromatic diamines or control the relative proportion of aromatic tetrahydric dianhydride and end-capping reagent, the viscosity of reaction system can be regulated, finally obtain high solids content, low viscosity polyimide prepolymer, the method reactions steps is simple, and productive rate is quite high, close to 100%, production process height is controlled, is suitable for industrialization.
2, solid content controls between 30% to 35% by the present invention in reaction process, can meet the requirement of electron device user height thickness polyimide coating, can improve resistance to sparking and other aspect performances of electron device.
3, solid content controls between 30% to 35% by the present invention in reaction process, can effectively reduce the usage quantity of solvent, reduces production and the transportation cost of product, reduces organic reagent to the pollution of environment.
Accompanying drawing explanation
Accompanying drawing 1 is Kapton infrared spectrum of the present invention.
Accompanying drawing 2 is that Kapton TGA of the present invention schemes.
Accompanying drawing 3 is Kapton frequency of the present invention and specific inductivity graph of a relation.
Accompanying drawing 4 is Kapton frequency of the present invention and dielectric loss graph of a relation.
Embodiment
Below in conjunction with accompanying drawing, embodiment provided by the invention is elaborated.
Polyamic acid prepared by the present invention has following chemical structure:
Wherein, R
1be selected from:
R
2be selected from:
R
3be selected from:
The preparation method of high solids content of the present invention, low viscosity polyimide prepolymer comprises the following steps: under protection of inert gas; aromatic diamines is dissolved in organic solvent; mechanical stirring; after aromatic diamines all dissolves; add aromatic diacid acid anhydride, adhesion promotor and end-capping reagent; at room temperature react to obtain polyamic acid solution, i.e. polyimide prepolymer.Wherein, reaction system solid content is 30% ~ 35%, and system viscosity is 500 ~ 10000cp, and aromatic diamines and fragrant four dicarboxylic anhydride amount of substance ratios are 1:1 ~ 1:1.1, the mol ratio of adhesion promotor and aromatic diamines is 1% ~ 10%, and end-capping reagent and aromatic dianhydride mol ratio are 1% ~ 20%.
Aromatic diamines is selected from 4, 4 '-diaminodiphenyl oxide, 3, 4 '-diaminodiphenyl oxide, 3, 3 '-diaminodiphenyl oxide, 2, 3 '-diaminodiphenyl oxide, 2, 4 '-diaminodiphenyl oxide, 4, 4 '-diaminodiphenylmethane, 3, 4 '-diaminodiphenylmethane, 3, 3 '-diaminodiphenylmethane, 2, 3 '-diaminodiphenylmethane, 2, 4 '-diaminodiphenylmethane, 4, 4 '-diamino-3, 3 '-dimethyl diphenyl methane, 4, 4 '-diamino-3, 3 '-diethyl ditane, 4, 4 '-diamino-3, 3 '-dimethyl diphenyl, 1, two (the 4 '-amino phenolic group) benzene of 3-, 1, two (the 3 '-amino phenolic group) benzene of 3-, 1, two (the 4 '-amino phenolic group) benzene of 4-, 1, two (the 3 '-amino phenolic group) benzene of 4-, 4, 4 '-diaminobenzophenone, 3, 4 '-diaminobenzophenone, 3, 3 '-diaminobenzophenone, 2, 3 '-diaminobenzophenone, 2, the derivative of 4 '-diaminobenzophenone or above-mentioned aromatic diamines.
Fragrance four dicarboxylic anhydrides are selected from 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, pyromellitic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 4, the two Tetra hydro Phthalic anhydride, 3 of 4 '-oxygen, 4, the derivative of 3 ', 4 '-diphenyl sulfone dianhydride, 3,6-bis-(methoxyl group) benzene dianhydride, hexafluorodianhydride or above-mentioned fragrant four dicarboxylic anhydrides.
Adhesion promotor is selected from 1,3 pairs of (3-aminopropyls)-1,1,3,3-tetramethyl disiloxane, 1,3 pairs of (3-aminopropyls)-1,1, the derivative of 3,3-tetraphenyl sily oxide, two (3-aminopropyl)-tetramethyl-polysiloxane, two (3-aminopropyl)-tetraphenyl polysiloxane or above-mentioned adhesion promotor.
End-capping reagent is selected from the derivative of maleic anhydride, cyanate, benzocyclobutene, maleimide, trifluoro-ethylene oxygen, acetylene, phenylacetylene, benzo maleimide, norbornylene imines, duplex benzene, cyano group or above-mentioned end-capping reagent.
Organic solvent is selected from N-Methyl pyrrolidone, N,N-dimethylacetamide, DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF)/methyl alcohol, phenylformic acid or Whitfield's ointment.
embodiment 1
By 4 of 10.27g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 60ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.49g maleic anhydride and 1.34g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 16.11g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 10.3ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 30%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 934cp.
embodiment 2
By 4 of 9.99g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 60ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.49g maleic anhydride and 1.30g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 16.11g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 9.5ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 30%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 1145cp.
embodiment 3
By 4 of 9.80g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 60ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.49g maleic anhydride and 1.28g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 16.11g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 9ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 30%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 1473cp.
embodiment 4
By 4 of 10.21g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 60ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 0.82g norbornene dicarboxylic anhydride, then add 3,3 ', 4 of 16.11g, 4 '-benzophenone tetracarboxylic dianhydride in batches, add the N,N-dimethylacetamide of 7.6ml, make solution solid content reach 30%, under room temperature, react 7h.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 2400cp.
embodiment 5
By 4 of 19.02g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 120ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.98g maleic anhydride and 2.48g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 32.22g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 16.3ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 30%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 3159cp.
embodiment 6
By 4 of 19.02g, 4 '-diamino-3,3 '-dimethyl diphenyl methane adds in there-necked flask, then adds 115ml N,N-dimethylacetamide, stirring and dissolving 15min.Dissolve complete, add 1 of 0.98g maleic anhydride and 2.48g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 32.22g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 9.1ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 32%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record the viscosity of reaction solution for 4319cp.
embodiment 7
By 4 of 19.02g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 110ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.98g maleic anhydride and 2.48g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 32.22g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 8.6ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 33%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record soltion viscosity for 7550cp.
embodiment 8
By 4 of 19.02g, 4 '-diaminodiphenyl oxide adds in there-necked flask, then adds 100ml N,N-dimethylacetamide, stirring and dissolving 40min.Dissolve complete, add 1 of 0.98g maleic anhydride and 2.48g, 3 pairs of (3-aminopropyls)-1,1,3,3-tetraphenyl sily oxide, then add 3 of 32.22g in batches, 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, add the N of 8.5ml, N-N,N-DIMETHYLACETAMIDE, makes solution solid content reach 35%, reacts 7h under room temperature.At 25 DEG C, Brookfield DV-S digital display type viscometer is used to record soltion viscosity for 9992cp.
the imidization of embodiment 9 polyamic acid
By the solution that embodiment 1 ~ 6 is synthesized, be paved into film after press filtration, 50 ~ 100 DEG C are gone down to desolventize.Above-mentioned steps process rear film puts into retort furnace, (starting temperature is 25 DEG C to gradient increased temperature, is warmed up to 120 DEG C through 95min, 120 DEG C of insulation 90min, 30min is warming up to 150 DEG C, 150 DEG C of insulations 60min, 50min are warming up to 200 DEG C, 200 DEG C of insulation 60min, 220 DEG C are warming up in 20min, 220 DEG C of insulations 60min, 30min are warming up to 250 DEG C, 250 DEG C of insulation 120min).Obtain Kapton.
embodiment 10 Kapton is tested
By polyimide prepolymer solution prepared in embodiment 3, the step through embodiment 7 obtains Kapton, this film is used for the tests such as infrared, mechanics, calorifics, electricity.Result is as shown in accompanying drawing 1-4 and table 1.
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the prerequisite not departing from the inventive method; can also make some improvement and supplement, these improve and supplement and also should be considered as protection scope of the present invention.
Claims (10)
1. the preparation method of a high solids content, low viscosity polyimide prepolymer; it is characterized in that; described preparation method comprises the following steps: under protection of inert gas; aromatic diamines is dissolved in organic solvent; mechanical stirring, after aromatic diamines all dissolves, adds aromatic diacid acid anhydride, adhesion promotor and end-capping reagent; at room temperature react to obtain polyamic acid solution, i.e. polyimide prepolymer.
2. preparation method according to claim 1, is characterized in that, reaction system solid content is 30% ~ 35%, and system viscosity is 500 ~ 10000cp.
3. preparation method according to claim 1, is characterized in that, described aromatic diamines and fragrant four dicarboxylic anhydride amount of substance ratios are 1:1 ~ 1:1.1.
4. preparation method according to claim 1, is characterized in that, described adhesion promotor and the mol ratio of aromatic diamines are 1% ~ 10%.
5. preparation method according to claim 1, is characterized in that, described end-capping reagent and aromatic dianhydride mol ratio are 1% ~ 20%.
6. preparation method according to claim 1, is characterized in that, described aromatic diamines is selected from 4,4 '-diaminodiphenyl oxide, 3,4 '-diaminodiphenyl oxide, 3,3 '-diaminodiphenyl oxide, 2,3 '-diaminodiphenyl oxide, 2,4 '-diaminodiphenyl oxide, 4,4 '-diaminodiphenylmethane, 3,4 '-diaminodiphenylmethane, 3,3 '-diaminodiphenylmethane, 2,3 '-diaminodiphenylmethane, 2,4 '-diaminodiphenylmethane, 4,4 '-diamino-3,3 '-dimethyl diphenyl methane, 4,4 '-diamino-3,3 '-diethyl ditane, 4,4 '-diamino-3,3 '-dimethyl diphenyl, two (the 4 '-amino phenolic group) benzene of 1,3-, two (the 3 '-amino phenolic group) benzene of 1,3-, Isosorbide-5-Nitrae-bis-(4 '-amino phenolic group) benzene, Isosorbide-5-Nitrae-bis-(3 '-amino phenolic group) benzene, 4,4 '-diaminobenzophenone, 3,4 '-diaminobenzophenone, 3,3 '-diaminobenzophenone, 2,3 '-diaminobenzophenone, 2, the derivative of 4 '-diaminobenzophenone or above-mentioned aromatic diamines.
7. preparation method according to claim 1, is characterized in that, described fragrance four dicarboxylic anhydride is selected from 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, pyromellitic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 4, the two Tetra hydro Phthalic anhydride, 3 of 4 '-oxygen, 4, the derivative of 3 ', 4 '-diphenyl sulfone dianhydride, 3,6-bis-(methoxyl group) benzene dianhydride, hexafluorodianhydride or above-mentioned fragrant four dicarboxylic anhydrides.
8. preparation method according to claim 1, it is characterized in that, described adhesion promotor is selected from 1,3 pairs of (3-aminopropyls)-1,1,3,3-tetramethyl disiloxane, 1,3 pairs of (3-aminopropyls)-1,1, the derivative of 3,3-tetraphenyl sily oxide, two (3-aminopropyl)-tetramethyl-polysiloxane, two (3-aminopropyl)-tetraphenyl polysiloxane or above-mentioned adhesion promotor.
9. preparation method according to claim 1, it is characterized in that, described end-capping reagent is selected from the derivative of maleic anhydride, cyanate, benzocyclobutene, maleimide, trifluoro-ethylene oxygen, acetylene, phenylacetylene, benzo maleimide, norbornylene imines, duplex benzene, cyano group or above-mentioned end-capping reagent.
10. preparation method according to claim 1, is characterized in that, described organic solvent is selected from N-Methyl pyrrolidone, N,N-dimethylacetamide, DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF)/methyl alcohol, phenylformic acid or Whitfield's ointment.
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| CN201410557628.1A CN104292459B (en) | 2014-10-21 | A kind of preparation method of high-solid-content and low-viscosity polyimide material |
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| CN201410557628.1A CN104292459B (en) | 2014-10-21 | A kind of preparation method of high-solid-content and low-viscosity polyimide material |
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| CN104292459A true CN104292459A (en) | 2015-01-21 |
| CN104292459B CN104292459B (en) | 2017-01-04 |
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| CN107573842A (en) * | 2016-07-04 | 2018-01-12 | 大亚电线电缆股份有限公司 | The polyimide insulative coating and enamel-covered wire of low dielectric |
| CN109762535A (en) * | 2019-02-12 | 2019-05-17 | 西南石油大学 | Shale intercalation inhibitor made of a kind of hyperbranched polyamine |
| CN110655650A (en) * | 2019-11-11 | 2020-01-07 | 同济大学 | Benzoxazine bridged polyimide precursor and preparation method thereof |
| CN110818897A (en) * | 2019-11-11 | 2020-02-21 | 同济大学 | Benzoxazine-terminated polyimide precursor and preparation method thereof |
| CN112585228A (en) * | 2018-08-22 | 2021-03-30 | Pi尖端素材株式会社 | Polyimide varnish for coating conductor containing aromatic carboxylic acid and method for producing same |
| CN113912848A (en) * | 2021-12-02 | 2022-01-11 | 王植源 | One-step method for preparing polyimide by using organic aromatic acid as reaction medium |
| CN114181392A (en) * | 2021-11-17 | 2022-03-15 | 北京化工大学 | High-solid-content low-viscosity polyamic acid solution and preparation method and application thereof |
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| CN101426338A (en) * | 2007-10-30 | 2009-05-06 | 达胜科技股份有限公司 | Lamination board and manufacturing method thereof |
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| CN1288925A (en) * | 1999-09-21 | 2001-03-28 | 中国科学院化学研究所 | Soluble polyimide coating glue and its preparation and use |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107573842A (en) * | 2016-07-04 | 2018-01-12 | 大亚电线电缆股份有限公司 | The polyimide insulative coating and enamel-covered wire of low dielectric |
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| CN112585228A (en) * | 2018-08-22 | 2021-03-30 | Pi尖端素材株式会社 | Polyimide varnish for coating conductor containing aromatic carboxylic acid and method for producing same |
| CN112585228B (en) * | 2018-08-22 | 2022-07-08 | Pi尖端素材株式会社 | Polyimide varnish for coating conductor containing aromatic carboxylic acid and method for producing same |
| CN109762535A (en) * | 2019-02-12 | 2019-05-17 | 西南石油大学 | Shale intercalation inhibitor made of a kind of hyperbranched polyamine |
| CN109762535B (en) * | 2019-02-12 | 2021-01-29 | 西南石油大学 | Shale intercalation inhibitor prepared from hyperbranched polyamine |
| CN110655650A (en) * | 2019-11-11 | 2020-01-07 | 同济大学 | Benzoxazine bridged polyimide precursor and preparation method thereof |
| CN110818897A (en) * | 2019-11-11 | 2020-02-21 | 同济大学 | Benzoxazine-terminated polyimide precursor and preparation method thereof |
| CN110818897B (en) * | 2019-11-11 | 2020-11-03 | 同济大学 | Benzoxazine-terminated polyimide precursor and preparation method thereof |
| CN114181392A (en) * | 2021-11-17 | 2022-03-15 | 北京化工大学 | High-solid-content low-viscosity polyamic acid solution and preparation method and application thereof |
| CN114181392B (en) * | 2021-11-17 | 2022-11-08 | 北京化工大学 | High-solid-content low-viscosity polyamic acid solution and preparation method and application thereof |
| CN113912848A (en) * | 2021-12-02 | 2022-01-11 | 王植源 | One-step method for preparing polyimide by using organic aromatic acid as reaction medium |
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