CN106831447A - How alkyl-substituted diamine compound of a kind of structure containing condensed-nuclei aromatics and its preparation method and application - Google Patents
How alkyl-substituted diamine compound of a kind of structure containing condensed-nuclei aromatics and its preparation method and application Download PDFInfo
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- 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
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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Abstract
The invention belongs to materials science field, a kind of how alkyl-substituted diamine compound of structure containing condensed-nuclei aromatics is specifically disclosed, shown in structural formula such as formula (I) or formula (II)：Wherein, X is hydrogen or alkyl；Y is hydrogen, phenyl, substituted-phenyl, polycyclic aromatic base, hydroxyl or halogen.The how alkyl-substituted diamine compound of structure containing condensed-nuclei aromatics provided by the present invention, condensed-nuclei aromatics steric hindrance is big on molecular structure, alkyl groups are more, be conducive to structure regulating, with the structural distortion that it is polyimide molecule chain prepared by monomer, pile up tight ness rating small, be suppressed with interchain CTC effects in strand.Simultaneously as condensed-nuclei aromatics structural stability is high, be conducive to keeping the heat endurance of polymer.Diamine compound synthesis of the invention is simple, and raw material is easy to get, and is adapted to industrialized production.There are very big potentiality in solvable, water white transparency polyimides is prepared, while being also applied for synthesizing polyamides and polyamidoimide high performance material.
Description
Technical field
The invention belongs to materials science field, more particularly, to a kind of many alkyl substitutions of structure containing condensed-nuclei aromatics
Diamine compound and its preparation method and application.
Background technology
Polyimides is the macromolecular material that a class contains imide ring structure, possesses excellent heat resistance, chemically stable
Property, the performance such as mechanical performance and dielectric properties, space flight and aviation, electrically and many necks such as automobile has been widely used in now
Domain.But traditional polyimides causes to form electric charge transfer network in intermolecular and intramolecular due to the height conjugation of its strand
Compound (charge transfer complexs, CTC) so that polyimides dissolubility is poor, color depth, and limits it micro-
The high-tech sector application such as electronics and photoelectron.Therefore, it is the one of polyimide material to research and develop solvable and colorless polyimide
Individual important research direction.
The method of the dissolubility and optical property that regulate and control polyimides from structure focuses primarily upon design synthesis containing non-co-
The diamines or dianhydride of yoke group.At present, nonconjugated group include flexible ether linkage (Macromolecules, 2006,39,7555-
7560), big steric hindrance side base (Chem.Mater., 2001,13,2472-2475), helical structure, fluoro-containing group
(J.Polym.Sci.Part A:Polym.Chem., 2013,51,4413-4422) and fat units
(Macromol.Rapid.Commun.,2000,21,1166–1170；J.Polym.Sci.Part A:Polym.Chem.,
2009,47,3309-3317) etc..But the introducing of these nonconjugated groups has certain limitation, ehter bond and fat are for example introduced
Unit often reduces the heat endurance and mechanical performance of material, and introducing trifluoromethyl can influence the dimensional stability of polymer.
Therefore, recent people are more paid close attention to different groups while be incorporated into same monomer, to improve polyamides sub-
While the dissolubility and optical transparence of amine, other properties of material are not influenceed.Wherein, many alkyl substitution containing fragrant side base
Diamine compound the stability of aromatic radical is had concurrently due to the steric effect of existing alkyl again, and enjoy favor.Chinese patent
CN1206203A and CN1970527A report the how alkyl-substituted diamine monomer that a class contains fragrant side base.These patent reports
How alkyl-substituted diamine monomer side base all be phenyl or fluorination benzene analog derivative, meanwhile, alkyl the position of substitution is single.
The content of the invention
It is an object of the invention to according to deficiency of the prior art, there is provided a kind of many alkyl of structure containing condensed-nuclei aromatics take
The diamine compound in generation.
Preparation method another object of the present invention is to provide above-mentioned diamine compound.
It is still another object of the present invention to provide the application of above-mentioned diamine compound.
The how alkyl-substituted diamine compound of structure containing polycyclic aromatic synthesized by the present invention, because condensed-nuclei aromatics has more
Big steric effect, the polymer molecular chain interaction as prepared by such diamine monomer is smaller, and free volume is bigger, and makes material
Material has excellent dissolubility and colorless transparency.
The purpose of the present invention is achieved through the following technical solutions：
The invention provides a kind of how alkyl-substituted diamine compound of structure containing condensed-nuclei aromatics, structural formula such as formula (I) or
Shown in formula (II)：
Wherein, X is hydrogen or alkyl；Y is hydrogen, phenyl, substituted-phenyl, polycyclic aromatic base, hydroxyl or halogen.
Preferably, X is hydrogen or C1~5Alkyl.
Most preferably, X is hydrogen, methyl or isopropyl.
Preferably, Y is polycyclic aromatic base.
Preferably, X is hydrogen or C1~3Alkyl.
Preferably, Y is selected from the one kind in following group：
Most preferably, Y is
Present invention simultaneously provides the preparation method of described diamine compound, including by aldehyde compound Y-CHO and replace
Anil reacts under the catalysis of Bronsted acid and obtains；
Shown in the structural formula of the substituted aniline derivative such as formula (III) or formula (IV)：
Wherein, X is hydrogen or alkyl；Y is hydrogen, phenyl, substituted-phenyl, polycyclic aromatic base, hydroxyl or halogen.
Preferably, the Bronsted acid be hydrochloric acid, sulfuric acid, trifluoroacetic acid, TFMS, p-methyl benzenesulfonic acid in one kind or
It is various.
Preferably, the reaction temperature is 80~160 DEG C.
Preferably, the aldehyde compound Y-CHO and the reaction mol ratio of substituted aniline derivative are 1：(2~8).
Compared with prior art, the present invention has advantages below and beneficial effect：
1st, the how alkyl-substituted diamine compound of structure containing condensed-nuclei aromatics provided by the present invention, the condensed ring on molecular structure
Aromatic hydrocarbons steric hindrance is big, and alkyl groups are more, are conducive to structure regulating, with the torsion that it is polyimide molecule chain prepared by monomer
Song, it is small to pile up tight ness rating, is suppressed with interchain CTC effects in strand.Simultaneously as condensed-nuclei aromatics structural stability is high,
Be conducive to keeping the heat endurance of polymer.
2nd, diamine compound of the invention is reacted a step by substitution formaldehyde and polyalkylbenzene amine derivative and is obtained, synthesis letter
Single, purifying is easy, and raw material is easy to get, and is adapted to industrialized production.
3rd, the how alkyl-substituted diamine monomer of structure containing condensed-nuclei aromatics of the invention is preparing solvable, water white transparency polyamides
There are very big potentiality, while being also applied for synthesizing polyamides and polyamidoimide high performance material in imines.
Brief description of the drawings
The diamine compound that Fig. 1 the present embodiment 1 is synthesized by aniline and 1- naphthaldehydes1H NMR spectras.
The diamine compound that Fig. 2 the present embodiment 2 is synthesized by 2,6- dimethylanilines and 1- naphthaldehydes1HNMR spectrograms.
The diamine compound that Fig. 3 the present embodiment 3 is synthesized by 2,6- diisopropyl anilines and 1- naphthaldehydes1H H NMR spectroscopies
Figure.
The diamine compound that Fig. 4 the present embodiment 4 is synthesized by 2,4- dimethylanilines and 1- naphthaldehydes1H NMR spectras.
Specific embodiment
The present invention is further illustrated below in conjunction with specific embodiments and the drawings, but embodiment does not do any to the present invention
The restriction of form.Unless stated otherwise, the reagent for using of the invention, method and apparatus are the art conventional reagent, method
And equipment.
Unless stated otherwise, agents useful for same of the present invention and material are purchased in market.
Embodiment 1
The diamine structures formula of the present embodiment synthesis is as follows：
The synthesis step of above-mentioned diamines is as follows：16.63g aniline is placed in 100mL there-necked flasks, is stirred, lead to nitrogen displacement
Air in bottle, after being heated to 130 DEG C, is instilled the concentrated hydrochloric acid mixed solution of 7.87g 1- naphthaldehydes and 4.2mL with dropping funel
In reaction system, thermotonus 18h is kept, reaction system retrogradation is dark-brown.Reaction terminates rear system and is cooled to 60 DEG C,
After the sodium hydrate aqueous solution of 10g 20wt% is added dropwise under agitation, instill in 100mL methyl alcohol, separate out solid.Through filtering, methyl alcohol
After repeatedly washing solid with water, with recrystallizing methanol, tan crystals are separated out, crystal is collected by filtration, be vacuum dried at 60 DEG C
12h, obtains 6.93g products, and yield is 24%.
Product fusing point：219~220 DEG C.
Infrared spectrum (KBr, cm-1)：3436,3416,3337,3212,3025,1619,1509,1271,1176,830,
800,572,507.
Proton nmr spectra (400MHz, DMSO-d6, ppm), δ=8.04 (d, J=8.0Hz, 1H), 7.89-7.85 (m,
1H), 7.73 (d, J=8.2Hz, 1H), 7.45-7.34 (m, 3H), 6.93 (d, J=7.1Hz, 1H), 6.74 (t, J=7.9Hz,
4H), 6.48 (t, J=8.3Hz, 4H), 5.94 (s, 1H), 4.86 (s, 4H).
Elementary analysis:found:H.5.903%, C.84.86%, N.8.81%；Calc.:H.8.21%, C.85.15%,
N.8.63%.
Embodiment 2
The diamine structures formula of the present embodiment synthesis is as follows：
Above-mentioned diamines synthesis step is as follows：15.59g 2,6- dimethylanilines are placed in 100mL there-necked flasks, stirring is led to
Air in nitrogen displacement bottle, is heated to 80 DEG C.4.29g 1- naphthaldehydes are sufficiently mixed with 2.5mL concentrated hydrochloric acids activates it, and
Activation 1- naphthaldehyde solution is added dropwise in reaction system in 1.5h.It is then heated to 120 DEG C, back flow reaction 10h.With reaction
Carrying out, reaction system is changed into blue, eventually becomes blue thick liquid from brown solution.After system drops to 60 DEG C, add
The sodium hydrate aqueous solution of 7.5g 20wt%.Room temperature is cooled to again, under agitation, reaction system is added to 200mL methyl alcohol
In, separate out faint yellow solid.Through filtering, after first alcohol and water repeatedly washs solid, with recrystallizing methanol, greyish crystals are separated out,
Crystal is collected by filtration, after being vacuum dried 12h at 60 DEG C, 3.60g products is obtained, yield is 36%.
Product fusing point：214~215 DEG C.
Infrared spectrum (KBr, cm-1)：3448,3396,2972,2924,1623,1956,1490,1438,1307,1145,
883,788,736.
Proton nmr spectra (400MHz, DMSO-d6, ppm), δ=8.02 (d, J=7.7Hz, 1H), 7.88-7.84 (m,
1H), 7.72 (d, J=8.2Hz, 1H), 7.44-7.33 (m, 3H), 6.96 (d, J=7.1Hz, 1H), 6.53 (s, 4H), 5.87
(s,1H),4.33(s,4H),1.98(s,12H)。
Elementary analysis:found:H.7.469%, C.85.06%, N.7.47%；Calc.:H.7.42%, C.85.22%,
N.7.36%.
Embodiment 3
The diamine structures formula of the present embodiment synthesis is as follows：
Above-mentioned diamines synthesis step is as follows：Successively by 22.33g 2,6- diisopropyl anilines, 15mL water, 30mL ethylene glycol
Methyl ether is added in 100mL there-necked flasks, leads to air in nitrogen displacement bottle, is heated to 90 DEG C.The 7.5mL concentrated sulfuric acids are slowly dropped into bottle,
Colourless transparent solution is obtained, then instills 10.40g 1- naphthaldehydes, be warming up to 100 DEG C, react 14h.Occurs yellow in reaction system
Sediment.Reaction is cooled to room temperature after terminating, and by reaction system addition 800mL water, adjusts pH to 9~10,4h is stirred, through filtering
Solid is obtained, with a large amount of water cyclic washing solids.Solid is dissolved in into dichloromethane, water is extracted three times, removes inorganic salts, and revolving is removed
Dichloromethane is removed, white solid is obtained, then with recrystallizing methanol, white crystal is separated out, crystal is collected by filtration, it is true at 60 DEG C
After sky dries 12h, 7.20g products are obtained, yield is 49%.
Product fusing point：132~133 DEG C.
Infrared spectrum (KBr, cm-1)：3460,3385,2959,2869,1622,1595,1465,1392,1353,1287,
786。
Proton nmr spectra (400MHz, DMSO-d6, ppm), δ=8.24-8.17 (m, 1H), 7.88-7.82 (m, 1H),
7.70 (d, J=8.2Hz, 1H), 7.41 (dd, J=9.6,5.0Hz, 2H), 7.37 (t, J=5.4Hz, 1H), 6.97 (d, J=
7.1Hz, 1H), 6.71 (s, 4H), 5.99 (d, J=8.7Hz, 1H), 4.35 (s, 4H), 2.95 (hept, J=6.6Hz, 4H),
1.02 (dd, J=8.2,7.0Hz, 24H).
Elementary analysis:found:H.9.035%, C.85.43%, N.5.57%；Calc.:H.9.00%, C.85.31%,
N.5.69%.
Embodiment 4
The diamine structures formula of the present embodiment synthesis is as follows：
Above-mentioned diamines synthesis step is as follows：15.61g 2,4- dimethylanilines are added in 100mL there-necked flasks, lead to nitrogen
Air in displacement bottle, is heated to 120 DEG C.During 4.17g 1- naphthaldehydes and 2.5mL concentrated hydrochloric acids mixed solution instilled into reaction system,
After keeping 120 DEG C of reaction 15h, 140 DEG C of reaction 1h are warmed up to, final system is changed into clear yellow viscous liquid.After system cools to 60 DEG C,
The sodium hydrate aqueous solution of 7.5g 20% is added, room temperature is then cooled to, under agitation, reaction system instills 200mL methyl alcohol
In, separate out the solid of brown color.Through filtering, after first alcohol and water repeatedly washs solid, with recrystallizing methanol, yellow solid is obtained,
Solid is collected by filtration, after being vacuum dried 12h at 60 DEG C, 2.10g products is obtained, yield is 22%.
Infrared spectrum (KBr, cm-1)：3445,3416,3363,2865,2859,1642,1541,1521,1490,1439,
1394,1255,866,796,776,675,560.
Proton nmr spectra (400MHz, DMSO-d6, ppm), δ=7.93 (d, J=7.6Hz, 1H), 7.82 (d, J=
8.1Hz, 2H), 7.51-7.38 (m, 3H), 6.94 (d, J=7.1Hz, 1H), 6.72 (s, 2H), 6.19 (s, 2H), 6.03 (s,
1H),4.13(s,4H),2.10(s,6H),1.96(s,6H)。
Elementary analysis:found:H.7.14%, C.85.64%, N.7.10%；Calc.:H.7.42%, C.85.22%,
N.7.36%.
Diamine compound provided in an embodiment of the present invention is prepared into polyimides, wherein, provided with embodiment 1~3
Compound as a example by, respectively withThe corresponding polyimides of reaction generation,Its
Dissolubility and optical transmission are respectively as shown in Tables 1 and 2.
The dissolubility of the polyimides of the different diamine compound synthesis of table 1
++：Is dissolved at room temperature
+：Is dissolved in the case where being heated to 100 DEG C
+-：Is partly dissolved in the case where 100 DEG C or boiling temperature is heated to
-：The insoluble solubility of heating is to judge after being heated 24 hours under the concentration of 10mg/mL
1/ODPA represents the polyimide material that the diamine compound of the preparation of embodiment 1 is prepared with ODPA, other classes
Push away.
The optical transmission of the polyimides of the different diamine compound synthesis of table 2
Wherein, λ0%/ nm represents the wavelength that transmitance is as 0%, T400nm/ % represents the light transmittance under 400nm wavelength.
From the point of view of from Tables 1 and 2, the dissolubility and light transmittance of the material that embodiment 3 is provided are optimal, are particularly suitable as system
Standby feature polyimide material.
Claims (10)
1. a kind of how alkyl-substituted diamine compound of structure containing condensed-nuclei aromatics, it is characterised in that structural formula such as formula (I) or formula
(II) shown in：
Wherein, X is hydrogen or alkyl；Y is hydrogen, phenyl, substituted-phenyl, polycyclic aromatic base, hydroxyl or halogen.
2. diamine compound according to claim 1, it is characterised in that X is hydrogen or C1~5Alkyl.
3. diamine compound according to claim 1, it is characterised in that Y is polycyclic aromatic base.
4. diamine compound according to claim 1, it is characterised in that X is hydrogen or C1~3Alkyl.
5. diamine compound according to claim 1, it is characterised in that Y is selected from the one kind in following group：
6. the preparation method of the diamine compound described in a kind of claim 1, it is characterised in that including by aldehyde compound Y-
CHO reacts under the catalysis of Bronsted acid with substituted aniline derivative and obtains；
Shown in the structural formula of the substituted aniline derivative such as formula (III) or formula (IV)：
Wherein, X is hydrogen or alkyl；Y is hydrogen, phenyl, substituted-phenyl, polycyclic aromatic base, hydroxyl or halogen.
7. preparation method according to claim 6, it is characterised in that the Bronsted acid be hydrochloric acid, sulfuric acid, trifluoroacetic acid,
One or more in TFMS, p-methyl benzenesulfonic acid.
8. preparation method according to claim 6, it is characterised in that the reaction temperature is 80~160 DEG C.
9. preparation method according to claim 6, it is characterised in that the aldehyde compound Y-CHO spreads out with substituted aniline
Biological reaction mol ratio is 1：(2~8).
10. any described diamine compound of claim 1 to 5 is preparing polyamide, polyimides or polyamide as monomer
Application in imide polymer.
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| CN113651701A (en) * | 2021-08-16 | 2021-11-16 | 艾蒙特成都新材料科技有限公司 | High-heat-resistance aromatic diamine organic matter and preparation method thereof |
| CN114591188A (en) * | 2022-04-02 | 2022-06-07 | 南京工业大学 | Full-bio-based aryl diamine chain extender and preparation method and application thereof |
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