CN113651701A - High-heat-resistance aromatic diamine organic matter and preparation method thereof - Google Patents
High-heat-resistance aromatic diamine organic matter and preparation method thereof Download PDFInfo
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- 150000004984 aromatic diamines Chemical class 0.000 title claims abstract description 54
- 239000005416 organic matter Substances 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000003960 organic solvent Substances 0.000 claims abstract description 45
- 238000003756 stirring Methods 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 16
- 239000012074 organic phase Substances 0.000 claims abstract description 14
- 238000005406 washing Methods 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 239000005457 ice water Substances 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 230000007935 neutral effect Effects 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 11
- 239000012071 phase Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 19
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000008367 deionised water Substances 0.000 claims description 17
- 229910021641 deionized water Inorganic materials 0.000 claims description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 230000002194 synthesizing effect Effects 0.000 claims description 15
- 239000012153 distilled water Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 claims description 8
- VEEXIHQTCQUWED-UHFFFAOYSA-N 3-(4-methylphenyl)benzaldehyde Chemical compound C1=CC(C)=CC=C1C1=CC=CC(C=O)=C1 VEEXIHQTCQUWED-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 8
- RZSUJIUTUGMZPG-UHFFFAOYSA-N 2,6-ditert-butylaniline Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1N RZSUJIUTUGMZPG-UHFFFAOYSA-N 0.000 claims description 7
- RHOGHORSTBGFPJ-UHFFFAOYSA-N 8-methylnaphthalene-1-carbaldehyde Chemical compound C1=CC(C=O)=C2C(C)=CC=CC2=C1 RHOGHORSTBGFPJ-UHFFFAOYSA-N 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 239000008399 tap water Substances 0.000 claims description 7
- 235000020679 tap water Nutrition 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229920005989 resin Polymers 0.000 abstract description 15
- 239000011347 resin Substances 0.000 abstract description 15
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 abstract description 14
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract description 14
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- -1 aromatic nitro compounds Chemical class 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- ZUTCJXFCHHDFJS-UHFFFAOYSA-N 1,5-dinitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1[N+]([O-])=O ZUTCJXFCHHDFJS-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-KHWBWMQUSA-N 2,6-diethylaniline Chemical group CCC1=CC=CC(CC)=C1[15NH2] FOYHNROGBXVLLX-KHWBWMQUSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- OPZGHHMHHWXKAA-UHFFFAOYSA-N benzenesulfonic acid;hydrochloride Chemical group Cl.OS(=O)(=O)C1=CC=CC=C1 OPZGHHMHHWXKAA-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a high heat-resistant aromatic diamine organic matter with a chemical structural formula shown in formula (I) and a preparation method thereof, wherein the preparation method of the high heat-resistant aromatic diamine organic matter comprises the following steps: adding an acid catalyst and water into a round-bottom flask provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, dropwise adding aromatic monoamine into an ice-water bath, heating, dropwise adding aromatic aldehyde, reacting at 50-70 ℃ for 2-4 h, and heating to 90-110 ℃ for 4-6 h; and cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution to the reaction mixture while stirring until the pH value is 8-9, adding an organic solvent, stirring, standing to separate out a water phase, washing the organic phase to be neutral by using water, removing water, and distilling to remove the organic solvent to obtain the catalyst. The high heat-resistant aromatic diamine organic matter can be used for preparing electronic-grade special bismaleimide resin and curing epoxyThe resin is suitable for the field of printed circuit boards and has good performance.
Description
Technical Field
The invention belongs to organic compounds and preparation thereof, and relates to a high heat-resistant aromatic diamine organic matter and a preparation method thereof. The high heat-resistant aromatic diamine organic matter can be used for preparing electronic grade special bismaleimide resin and cured epoxy resin, so that the product is suitable for the field of printed circuit boards.
Background
The 5G technology has become a hot spot pursued by various industries, and brings convenience and hope to people, and meanwhile brings a series of problems, such as higher power consumption and higher heat productivity. In order to meet the development trend of increasingly high frequency and high speed of electronic signal processing and signal transmission and high precision and high integration of electronic components, higher requirements are provided for the thermal property, dielectric property and processing property of electronic grade synthetic resin used for a printed circuit board bearing electronic components.
Bismaleimide resin is widely used in the field of copper clad laminate by virtue of its excellent heat resistance, dielectric property and mechanical property. Since a diamine monomer for synthesizing bismaleimide has excellent structural design, and can impart excellent properties to bismaleimide by introducing functional groups having different structures to be applicable to different scenes, the development of bismaleimide resins having high heat resistance and solubility has become an important research direction for electronic resins. The relationship between the aromatic diamine structure and the bismaleimide resin performance and the mechanism are not perfect, and the application of the aromatic diamine resin is limited. Therefore, it is necessary to further develop intensive studies for designing and synthesizing aromatic diamine monomers.
In the prior art, aromatic hydrocarbons with corresponding structural units are usually used as raw materials for synthesizing aromatic diamines with different structures, and aromatic amine organic matters are finally obtained through nitration reaction and reduction reaction. The nitration reaction usually uses mixed acid of nitric acid and sulfuric acid as a nitration reagent, the heat release amount is large in the reaction process, especially the dinitration reaction can cause safety risk if the heat is not removed; hydrazine is often used for reducing nitro products, for example, a method for preparing 1, 5-diaminonaphthalene by reducing 1, 5-dinitronaphthalene with hydrazine hydrate disclosed in CN102070467A, a method for preparing aromatic amine by reducing aromatic nitro compounds with hydrazine hydrate disclosed in CN105669338A, and the like, the usage amount of hydrazine hydrate is usually 3-10 times of the molar amount of nitro groups in the aromatic nitro compounds, and the method has the disadvantages of large usage amount of hydrazine hydrate, difficult recovery, environmental pollution, difficult separation of byproducts and products, and is not favorable for large-scale industrial production. Therefore, a path with simple synthesis process, easy purification and high yield of aromatic diamine is needed.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a high-heat-resistance aromatic diamine organic matter and a preparation method thereof. Thereby providing the high heat-resistant aromatic diamine organic matter which can be used as a raw material for synthesizing bismaleimide resin, can also be used as a curing agent of epoxy resin and can further improve the thermal property and the solubility and the preparation method thereof. .
The content of the invention is as follows: a high heat-resistant aromatic diamine organic matter is characterized in that: the high heat-resistant aromatic diamine organic matter has a chemical structure general formula shown in a formula (I):
in formula (I): r1Are identical or different substituents, R1＝-H，-CN，-CnH2n+1(n＝1～10)；R2The corresponding aromatic aldehyde is any one of formulas (II) to (V); r3Are identical or different substituents, R3＝-H，-F，-Cl，-Br，-CnH2n+1(n is 1 to 10). The high heat-resistant aromaThe diamine organic matter is light yellow solid powder or brownish red solid powder, and the softening point is between 52 and 83 ℃.
Another aspect of the invention is: a preparation method of high heat-resistant aromatic diamine organic matters is characterized by comprising the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 1-2 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.5-1 h after the dropwise adding is finished, and gradually heating to 50-70 ℃ after the aromatic monoamine is completely dissolved; then 0.1-0.5 mol (preferably 0.1-0.2 mol) of aromatic aldehyde (dropping speed of 1-2 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 2-4 h at the temperature of 50-70 ℃ after the dripping is finished; heating to 90-110 ℃ (keeping the temperature for reaction for 4-6 hours) to obtain a reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: and (2) cooling the reacted material to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 2-4 ml/min) into the reacted material through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted material to 8-9, stopping dropwise adding, adding 30-80 ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted material in the organic solvent, standing for 0.5h, separating out an aqueous phase, washing the organic phase to be neutral with water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue, namely the prepared high-heat-resistance aromatic diamine organic matter.
In another aspect of the invention: the recovered organic solvent can be separated by rectification and used next time.
In another aspect of the invention: the acid catalyst can be one or a mixture of more than two of hydrochloric acid, sulfuric acid, phosphoric acid, benzenesulfonic acid and p-toluenesulfonic acid.
In another aspect of the invention: the alkali in the alkaline aqueous solution can be one or a mixture of more than two of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide.
In another aspect of the invention: the organic solvent can be one or a mixture of more than two of toluene, ethyl acetate, N-methyl pyrrolidone, N-dimethylformamide and N-butanol.
In another aspect of the invention: the water used for the water washing may be tap water, deionized water or distilled water.
Compared with the prior art, the invention has the following characteristics and beneficial effects:
(1) the molecular chain of the high heat-resistant aromatic diamine organic matter introduces large-volume biphenyl groups and naphthalene groups, which is more favorable for improving the heat resistance, moisture resistance and solubility of corresponding polymers, reducing dielectric constant, dielectric loss and the like;
(2) the high heat-resistant aromatic diamine organic matter can be used as a raw material for synthesizing bismaleimide resin and can also be used as a curing agent of epoxy resin; the introduction of high heat-resistant groups and groups which destroy the regularity of the molecular chain into the molecular chain of the aromatic diamine can not only improve the thermal property of the polymer, but also improve the solubility of the polymer; the high heat-resistant aromatic diamine organic matter (prepared) can be used for preparing electronic-grade special bismaleimide resin and cured epoxy resin, and the product is suitable for the field of printed circuit boards; the bismaleimide resin prepared by the (prepared) high heat-resistant aromatic diamine organic matter has excellent performance, good solubility in common organic solvents of toluene, acetone, butanone, chloroform and N, N-dimethylformamide, and the initial thermal decomposition temperature of a condensate is 360-420 ℃, and the carbon residue rate in a nitrogen atmosphere at 700 ℃ is 52-68%.
(3) The synthesis of the high heat-resistant aromatic diamine organic matter is obtained by condensation reaction of aromatic monoamine and aromatic aldehyde under the action of a catalyst; the preparation process is simple, the operation is easy, the byproducts are few, the cost is low, the used organic solvent can be recycled, the safety and the stability are high, and the practicability is high.
Detailed Description
The following examples are intended to further illustrate the present invention and should not be construed as limiting the scope of the invention, which is intended to be covered by the claims appended hereto.
Example 1:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water into a four-neck round-bottom flask provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing the mixture into an ice-water bath; dropwise adding 0.25mol of aromatic monoamine into the round-bottom flask through a constant-pressure dropping funnel at the dropping speed of 1.5ml/min, stirring for 1h after the dropwise adding is finished, and gradually heating to 60 ℃ after the aromatic monoamine is completely dissolved; after the temperature is stable, dropwise adding 0.2mol of benzaldehyde into the round-bottom flask through a constant-pressure dropping funnel at the dropping speed of 1ml/min, and maintaining the temperature for 4 hours after the dropwise adding is finished; the temperature is increased to 100 ℃ continuously and kept for 6 h.
b. And (3) post-treatment: after the reaction is completed, cooling to room temperature, under the condition of stirring, dropwise adding an alkali solution into a product at the dropping speed of 3ml/min through a constant-pressure dropping funnel, adjusting the pH to 9, stopping dropwise adding, then adding 80ml of an organic solvent, stirring for 0.5h, fully dissolving the product into the organic solvent, standing for 0.5h, separating out a water phase, retaining the organic phase, washing the organic phase with water (which can be tap water, deionized water or distilled water) to be neutral, removing water, and finally removing the organic solvent through reduced-pressure distillation to obtain a yellow transparent solid, namely the prepared high-heat-resistant aromatic diamine organic matter, wherein the product yield is 94%. Note: the recovered organic solvent can be separated by rectification and used for the next time.
The acid catalyst is hydrochloric acid or benzenesulfonic acid;
the aromatic monoamine is 2, 6-diethylaniline or 2, 6-diisopropylaniline;
the alkali in the alkaline aqueous solution can be any one of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide;
the organic solvent may be toluene or ethyl acetate.
The bismaleimide resin synthesized by the high heat-resistant aromatic diamine organic matter prepared in the embodiment 1 has good solubility in toluene, acetone, butanone, chloroform and N, N-dimethylformamide, the initial thermal decomposition temperature of a cured product is higher than 360 ℃, and the carbon residue rate in a nitrogen atmosphere at 700 ℃ reaches 52%.
Example 2:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water into a four-neck round-bottom flask provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing the mixture into an ice-water bath; dropwise adding 0.25mol of aromatic monoamine into the round-bottom flask at the dropping speed of 2ml/min through a constant-pressure dropping funnel, stirring for 0.5h after the dropwise adding is finished, and gradually heating to 70 ℃ after the aromatic monoamine is completely dissolved; after the temperature is stable, 0.1mol of 3- (4-methylphenyl) benzaldehyde is dripped into the round-bottom flask through the constant pressure dropping funnel at the dropping speed of 1ml/min, and the temperature is maintained for 4 hours after the dripping is finished; the temperature is increased to 105 ℃ and kept for 8 h.
b. And (3) post-treatment: after the reaction is completed, cooling to room temperature, under the condition of stirring, dropwise adding an alkali solution into a product at a dropping speed of 4ml/min through a constant-pressure dropping funnel, adjusting the pH to 9, stopping dropwise adding, then adding 80ml of an organic solvent, stirring for 0.5h, fully dissolving the product into the organic solvent, standing for 0.5h, separating out a water phase, retaining the organic phase, washing the organic phase with water (which can be tap water, deionized water or distilled water) to be neutral, removing water, and finally removing the organic solvent through reduced-pressure distillation to obtain a brown transparent solid, namely the prepared high-heat-resistant aromatic diamine organic matter, wherein the product yield is 92%. Note: the recovered organic solvent can be separated by rectification and used for the next time.
The acid catalyst is sulfuric acid or benzenesulfonic acid;
the aromatic monoamine is aniline or 2, 6-diisopropylaniline;
the alkali in the alkaline aqueous solution is any one of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide;
the organic solvent is toluene or ethyl acetate.
The bismaleimide resin synthesized by the high heat-resistant aromatic diamine organic matter prepared in the embodiment 2 has good solubility in toluene, acetone, butanone, chloroform and N, N-dimethylformamide, the initial thermal decomposition temperature of a cured product is higher than 400 ℃, and the carbon residue rate in a nitrogen atmosphere at 700 ℃ reaches 61%.
Example 3:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water into a four-neck round-bottom flask provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing the mixture into an ice-water bath; dropwise adding 0.25mol of aromatic monoamine into the round-bottom flask at the dropping speed of 2ml/min through a constant-pressure dropping funnel, stirring for 1h after the dropwise adding is finished, and gradually heating to 65 ℃ after the aromatic monoamine is completely dissolved; after the temperature is stable, dropwise adding a solution prepared by 0.1mol of 2-naphthaldehyde and an organic solvent into the round-bottom flask at the dropping speed of 1ml/min through a constant-pressure dropping funnel, and maintaining the temperature for 4 hours after the dropwise addition is finished; the temperature is increased to 110 ℃ continuously and kept for 8 h.
b. And (3) post-treatment: after the reaction is completed, cooling to room temperature, under the condition of stirring, dropwise adding an alkali solution into a product at a dropping speed of 4ml/min through a constant-pressure dropping funnel, adjusting the pH to 9, stopping dropwise adding, then adding 80ml of an organic solvent, stirring for 0.5h, fully dissolving the product into the organic solvent, standing for 0.5h, separating out a water phase, retaining the organic phase, washing the organic phase with water (which can be tap water, deionized water or distilled water) to be neutral, removing water, and finally removing the organic solvent through reduced-pressure distillation to obtain a brownish red transparent solid, namely the prepared high-heat-resistance aromatic diamine organic matter with a product yield of 91%. Note: the recovered organic solvent can be separated by rectification and used for the next time.
The aromatic monoamine is aniline or 2, 6-diethylaniline;
the acidic catalyst is benzenesulfonic acid hydrochloride or benzenesulfonic acid;
the alkali in the alkaline aqueous solution is any one of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide;
the organic solvent is toluene or N-methyl pyrrolidone.
The bismaleimide resin synthesized by the high heat-resistant aromatic diamine organic matter prepared in the embodiment 3 has good solubility in toluene, acetone, butanone, chloroform and N, N-dimethylformamide, the initial thermal decomposition temperature of a cured product is higher than 400 ℃, and the carbon residue rate in a nitrogen atmosphere at 700 ℃ reaches 60%.
Example 4:
a high heat-resistant aromatic diamine organic matter has a chemical structural general formula shown in formula (I):
in formula (I): r1Are identical or different substituents, R1＝-H，-CN，-CnH2n+1(n＝1～10)；R2The corresponding aromatic aldehyde is any one of formulas (II) to (V); r3Are identical or different substituents, R3＝-H，-F，-Cl，-Br，-CnH2n+1(n is 1 to 10). The high heat-resistant aromatic diamine organic matter is light yellow solid powder or brownish red solid powder, and the softening point is between 52 and 83 ℃.
Example 5:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 1 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.5h after the dropwise adding is finished, and gradually heating to 50 ℃ after the aromatic monoamine is completely dissolved; then 0.1mol of aromatic aldehyde (dropping speed of 1 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 2 hours at the temperature of 50 ℃ after the dripping is finished; heating to 90 deg.C, and reacting for 4h to obtain reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 2 ml/min) into the reacted materials through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted materials to 8, stopping dropwise adding, adding 30ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted materials in the organic solvent, standing for 0.5h, separating out a water phase, washing the organic phase to be neutral by using water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue, namely the prepared high-heat-resistant aromatic diamine organic matter.
Example 6:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 2 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 1h after the dropwise adding is finished, and gradually heating to 70 ℃ after the aromatic monoamine is completely dissolved; then 0.5mol of aromatic aldehyde (dropping speed of 2 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 4 hours at the temperature of 70 ℃ after the dripping is finished; heating to 110 deg.c for 6 hr to obtain reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 4 ml/min) into the reacted materials through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted materials to 9, stopping dropwise adding, adding 80ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted materials in the organic solvent, standing for 0.5h, separating out a water phase, washing the organic phase to be neutral by using water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue (yellow transparent solid), namely the prepared high-heat-resistance aromatic diamine organic matter.
Example 7:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 1.5 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.8h after the dropwise adding is finished, and gradually heating to 60 ℃ after the aromatic monoamine is completely dissolved; then 0.3mol of aromatic aldehyde (dropping speed of 1.5 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 3 hours at the temperature of 60 ℃ after the dripping is finished; heating to 100 deg.c for 5 hr to obtain reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 3 ml/min) into the reacted materials through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted materials to 8.5, stopping dropwise adding, adding 55ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted materials in the organic solvent, standing for 0.5h, separating out a water phase, washing the organic phase with water (tap water, deionized water or distilled water) to be neutral, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue (yellow transparent solid), namely the prepared high-heat-resistance aromatic diamine organic matter.
Example 8:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 1 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.5h after the dropwise adding is finished, and gradually heating to 55 ℃ after the aromatic monoamine is completely dissolved; then 0.12mol of aromatic aldehyde (dropping speed of 1 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 2.5 hours at the temperature of 53 ℃ after the dripping is finished; heating to 95 deg.C, and reacting for 4.5h to obtain reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 2 ml/min) into the reacted materials through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted materials to 8, stopping dropwise adding, adding 45ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted materials in the organic solvent, standing for 0.5h, separating out a water phase, washing the organic phase to be neutral by using water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue (yellow transparent solid), namely the prepared high-heat-resistance aromatic diamine organic matter.
Example 9:
a preparation method of high heat-resistant aromatic diamine organic matters comprises the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask (namely a four-mouth round-bottom flask) provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine (at the dropping speed of 1.5 ml/min) into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.7h after the dropwise adding is finished, and gradually heating to 58 ℃ after the aromatic monoamine is completely dissolved; then 0.2mol of aromatic aldehyde (dropping speed of 1.5 ml/min) is dripped into the round-bottom flask through a constant pressure dropping funnel, and the reaction is carried out for 3 hours at the temperature of 58 ℃ after the dripping is finished; heating to 98 deg.c for 5 hr to obtain reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: cooling the reacted materials to room temperature, dropwise adding an alkaline aqueous solution (dropping speed of 3 ml/min) into the reacted materials through a constant-pressure dropping funnel under stirring, adjusting the pH of the reacted materials to 9, stopping dropwise adding, adding 60ml of an organic solvent, stirring for 0.5h, fully dissolving the reacted materials in the organic solvent, standing for 0.5h, separating out a water phase, washing the organic phase to be neutral by using water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue (yellow transparent solid), namely the prepared high-heat-resistance aromatic diamine organic matter.
In the above examples 5 to 9: the recovered organic solvent can be separated by rectification and used next time.
In the above examples 5 to 9: the acid catalyst is one or a mixture of more than two of hydrochloric acid, sulfuric acid, phosphoric acid, benzenesulfonic acid and p-toluenesulfonic acid.
In the above examples 5 to 9: the alkali in the alkaline aqueous solution is one or a mixture of more than two of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide.
In the above examples 5 to 9: the organic solvent is one or a mixture of more than two of toluene, ethyl acetate, N-methyl pyrrolidone, N-dimethylformamide and N-butanol.
In the above examples 5 to 9: the water used for the water washing may be tap water, deionized water or distilled water.
The percentages used in the above examples, not specifically indicated, are percentages by weight or known to those skilled in the art; the proportions used, not specifically noted, are mass (weight) proportions; the parts by mass (by weight) may all be grams or kilograms.
In the above embodiment: the process parameters (temperature, time, concentration, dropping speed, etc.) and the amount of each component in each step are within the range, and any point can be applicable.
The present invention and the technical contents not specifically described in the above examples are the same as those of the prior art, and the raw materials are all commercially available products.
The present invention is not limited to the above-described embodiments, and the present invention can be implemented with the above-described advantageous effects.
Claims (7)
1. A high heat-resistant aromatic diamine organic matter is characterized in that: the high heat-resistant aromatic diamine organic matter has a chemical structure general formula shown in a formula (I):
in formula (I): r1＝-H，-CN，-CnH2n+1(n＝1～10)；R2The corresponding aromatic aldehyde is represented by the formula (II) to (C)Any one of V); r3＝-H，-F，-Cl，-Br，-CnH2n+1(n＝1～10)。
2. A preparation method of high heat-resistant aromatic diamine organic matters is characterized by comprising the following steps:
a. synthesizing: adding 0.2mol of acid catalyst and 20ml of deionized water or distilled water into a round-bottom flask provided with a stirrer, a thermometer, a reflux condenser and a constant-pressure dropping funnel, stirring and mixing uniformly, and placing in an ice-water bath; dropwise adding 0.25mol of aromatic monoamine into the round-bottom flask through a constant-pressure dropping funnel, stirring for 0.5-1 h after dropwise adding is finished, and heating to 50-70 ℃; dropwise adding 0.1-0.5 mol of aromatic aldehyde into the round-bottom flask through a constant-pressure dropping funnel, and reacting at 50-70 ℃ for 2-4 h after dropwise adding; heating to 90-110 ℃ and reacting for 4-6 h to obtain a reacted material;
the aromatic monoamine is one or a mixture of more than two of aniline, 2, 6-diethylaniline, 2, 6-diisopropylaniline and 2, 6-di-tert-butylaniline;
the aromatic aldehyde is any one of benzaldehyde, 1-methyl-8-naphthaldehyde, 1, 3-benzodioxy-4-formaldehyde and 3- (4-methylphenyl) benzaldehyde;
b. and (3) post-treatment: and (2) cooling the reacted material to room temperature, dropwise adding an alkaline water solution into the reacted material through a constant-pressure dropping funnel while stirring, adjusting the pH of the reacted material to 8-9, adding 30-80 ml of an organic solvent, stirring for 0.5h, standing for 0.5h, separating out a water phase, washing the organic phase to be neutral by using water, removing water, and finally removing the organic solvent through reduced pressure distillation to obtain a residue, namely the prepared high-heat-resistance aromatic diamine organic matter.
3. The method for preparing the highly heat-resistant aromatic diamine organic substance as set forth in claim 2, wherein: the 0.1 to 0.5mol of the aromatic aldehyde is 0.1 to 0.2mol of the aromatic aldehyde.
4. The method for preparing the highly heat-resistant aromatic diamine organic substance as set forth in claim 2 or 3, wherein: the acid catalyst is one or a mixture of more than two of hydrochloric acid, sulfuric acid, phosphoric acid, benzenesulfonic acid and p-toluenesulfonic acid.
5. The method for preparing the highly heat-resistant aromatic diamine organic substance as set forth in claim 2 or 3, wherein: the alkali in the alkaline aqueous solution is one or a mixture of more than two of sodium hydroxide, lithium hydroxide, potassium hydroxide and calcium hydroxide.
6. The method for preparing the highly heat-resistant aromatic diamine organic substance as set forth in claim 2 or 3, wherein: the organic solvent is one or a mixture of more than two of toluene, ethyl acetate, N-methyl pyrrolidone, N-dimethylformamide and N-butanol.
7. The method for preparing the highly heat-resistant aromatic diamine organic substance as set forth in claim 2 or 3, wherein: the water used for washing is tap water, deionized water or distilled water.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1448384A (en) * | 2002-03-29 | 2003-10-15 | 中国科学院化学研究所 | Polyalkyl substituted aromatic diamidogen containing aromatic lateral group and prep. and use thereof |
| CN101514164A (en) * | 2009-04-03 | 2009-08-26 | 东华大学 | Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof |
| CN103483206A (en) * | 2013-09-27 | 2014-01-01 | 桂林理工大学 | Diamine monomer containing asymmetric and non-coplanar structure, and preparation method of diamine monomer |
| CN103864648A (en) * | 2013-12-20 | 2014-06-18 | 中国海洋石油总公司 | Sulfonated aromatic diamine compound as well as preparation method and application thereof |
| CN104447351A (en) * | 2014-11-11 | 2015-03-25 | 桂林理工大学 | Fluorine-containing diamine monomer with large side group and non-coplanar structure and preparation method of fluorine-containing diamine monomer |
| CN106831447A (en) * | 2016-12-05 | 2017-06-13 | 中山大学 | How alkyl-substituted diamine compound of a kind of structure containing condensed-nuclei aromatics and its preparation method and application |
| CN108530304A (en) * | 2018-04-24 | 2018-09-14 | 武汉理工大学 | Aromatic diamines, polyimides containing tolyl and non-co-planar structure and preparation method thereof |
-
2021
- 2021-08-16 CN CN202110936625.9A patent/CN113651701A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1448384A (en) * | 2002-03-29 | 2003-10-15 | 中国科学院化学研究所 | Polyalkyl substituted aromatic diamidogen containing aromatic lateral group and prep. and use thereof |
| CN101514164A (en) * | 2009-04-03 | 2009-08-26 | 东华大学 | Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof |
| CN103483206A (en) * | 2013-09-27 | 2014-01-01 | 桂林理工大学 | Diamine monomer containing asymmetric and non-coplanar structure, and preparation method of diamine monomer |
| CN103864648A (en) * | 2013-12-20 | 2014-06-18 | 中国海洋石油总公司 | Sulfonated aromatic diamine compound as well as preparation method and application thereof |
| CN104447351A (en) * | 2014-11-11 | 2015-03-25 | 桂林理工大学 | Fluorine-containing diamine monomer with large side group and non-coplanar structure and preparation method of fluorine-containing diamine monomer |
| CN106831447A (en) * | 2016-12-05 | 2017-06-13 | 中山大学 | How alkyl-substituted diamine compound of a kind of structure containing condensed-nuclei aromatics and its preparation method and application |
| CN108530304A (en) * | 2018-04-24 | 2018-09-14 | 武汉理工大学 | Aromatic diamines, polyimides containing tolyl and non-co-planar structure and preparation method thereof |
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