CN105503649A - Polyols containing quaternary ammonium cations and Salen or Salophen functional groups and preparation method thereof - Google Patents
Polyols containing quaternary ammonium cations and Salen or Salophen functional groups and preparation method thereof Download PDFInfo
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- CN105503649A CN105503649A CN201610028950.4A CN201610028950A CN105503649A CN 105503649 A CN105503649 A CN 105503649A CN 201610028950 A CN201610028950 A CN 201610028950A CN 105503649 A CN105503649 A CN 105503649A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Abstract
In the invention, based on the molecular design principle and the advantages of the private research result 5-chloromethyl salicylaldehyde in industrial scale, a series of polyols containing quaternary ammonium cations and Salen or Salophen functional groups are prepared by adopting 5-chloromethyl salicylaldehyde as a major raw material, wherein the polyol has an anion-cation double exchange function and can be used as a raw material of polyester, polyurethane and polyether; and a raw material basis is laid for preparing special-structure functional polymer materials such as polymer electrolytes, ionic guide film materials, water-absorbing antibacterial fiber, anion-cation exchange resin and immobilized metallic catalytic materials.
Description
Technical field
The present invention relates to a kind of polyvalent alcohol and preparation method thereof, in particular to the polyvalent alcohol containing quaternary ammonium cation and Salen or Salophen function base in molecular structure, can be used for preparing the functional high molecule material such as polymer dielectric, ion guide mould material, water suction antibacterial fiber, anion-cation exchange resin, immobilized metal catalytic material, belong to organic functional material field.
Technical background
Polyvalent alcohol is a kind of raw material for the preparation of macromolecular materials such as polyester, urethane, polyethers.In polyol molecule structure, introduce ion or functional group is the main method of the macromolecular materials such as polyester, urethane, polyethers being carried out to modification or functionalization, occur positively charged ion polyvalent alcohol, anionic polyol alcohol, flame-proof polyol or unsaturated polyol etc. thus.Ammonium in its cationic polyol molecule structure, sulfonium base and Phosphonium base positively charged ion, preferred ammonium cation is the main raw material preparing the macromolecular materials such as cationic polyester, cation polyurethane, cation polyether.With positive electricity on the macromolecular chain such as polyester, urethane, polyethers be made up of quaternary ammonium cation type polyvalent alcohol, so it has certain characteristic such as water logging lubricant nature, electric conductivity, iontophoretic injection, can be used on preparation and the production of the materials such as polymer battery, ion separation membrane, ion exchange resin, at industry fields such as the energy, chemical industry, weaving, leather, health and papermaking, there is widespread use.Some documents are listed, such as: CN03122339.7 at this; CN201210125277.8; Polymericandimmobilizedcrowncompoundmaterialsforionsepar ation, Tetrahedron, 53 (1997) 1343-1360; Click-ligationofcoumarintopolyetherpolyolsforpolyurethan efoams, Polym.Int., 62 (2013) 783-790; Detectionofuraniumwithawirelesssensingmethodbyusingsalop henasreceptorandmagneticnanoparticlesassignal-amplifying tags, J.Radioanal.Nucl.Chem., 298 (2013) 1393-1399 etc., can spy on out some overviews of ion polyvalent alcohol or functionalization polyvalent alcohol.
Salen or Salophen type Schiff's base is the chelating Schiff's base that two identical aldehyde molecules and two amine molecule condensations generate, and has N
2o
2four part division centers, easy and metal ion forms planar metal title complex.Described Salen or Salophen metal complexes shows its superiority in fields such as catalyzed oxidation, catalytic hydrolysis, Heck coupling, catalyzed polymerization, ion blotting and photoelectric materials.But Salen or the Salophen metal complexes of high molecular has again the features such as unique easily separated, easy recovery, easily purifying in actual applications, the method of Salen or Salophen metal complexes high molecular there is following several mode: (1) organic polymer covalent linkage is immobilized, (2) inorganic polymer covalent linkage is immobilized, (3) organic polymer coordinate bond is immobilized, (4) self-polymerization of Salen or Salophen metal complexes, (5) other material investment fashion.Some documents are listed, such as Polymer-supportedSchiffbasecomplexesinoxidationreactions, Coord.Chem.Rev., 253 (2009) 1926-1946 at this; Metal-salophen-basedreceptorsforanions, Chem.Soc.Rev., 39 (2010) 3863-3874; SchiffBaseComplexesinMacromolecules, J.Inorg..Organometal.Poly.andMater., 17 (2007) 55-89; RecentAdvancesinAsymmetricC-CandC-NheteroatomBondForming ReactionsusingPolymer-BoundCatalysts, Adv.Synth.Catal., 345 (2003) 869-929 etc., discuss the progress of Salen or Salophen metal complexes high molecular.
But in existing published documents and materials, do not find the report simultaneously introducing quaternary ammonium cation and Salen or Salophen function base in polyol molecule structure.Based on this, the present inventor uses molecular design theory, utilize the plant-scale advantage of this seminar achievement in research 5-chloromethyl salicylaldehyde, with 5-chloromethyl salicylaldehyde for main raw material, the polyvalent alcohol containing quaternary ammonium cation and Salen or Salophen function base of seriation has been prepared in design, for the functional high molecule material such as polymer dielectric, ion guide mould material, water suction antibacterial fiber, anion-cation exchange resin, immobilized metal catalytic material preparing unique construction has established raw material basis.
Summary of the invention
The invention provides a kind of polyvalent alcohol containing quaternary ammonium cation and Salen or Salophen function base, there is structure shown in general formula (A) or general formula (B):
R in its formula of (A) or general formula (B)
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl,
be selected from C
1~ C
18alkylene or
in one, X is selected from C
2~ C
10alkylene,
or the one in aromatic nucleus, m is selected from the one in 1,2 or 3; Wherein said aromatic nucleus refers to the one in phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus, and described n is selected from the positive integer of 1 ~ 20;
The preparation method containing the polyvalent alcohol of quaternary ammonium cation and Salen or Salophen function base provided by the invention, realizes according to following preparation process:
The preparation of the quaternary ammonium salt of step one containing salicylic aldehyde
The oxyamine and the 5-chloromethyl poplar aldehyde that take structure shown in general formula (IA) or general formula (IB) respectively dissolve in a solvent, obtained described general formula (IA) or general formula (IB) hydroxylamine solutions and 5-chloromethyl salicylaldehyde solution, under room temperature, 5-chloromethyl salicylaldehyde solution is added in general formula (IA) or general formula (IB) hydroxylamine solutions, stirring reaction is after 2 ~ 6 hours, heat up 60 ~ 85 DEG C and continue stirring reaction 2 ~ 6 hours, reaction mass temperature is down to room temperature, standing separation, obtained general formula (IIA) or the shown structure of general formula (IIB) contain the quaternary ammonium salt of salicylic aldehyde, shown in seeing that reaction formula is 1.:
Wherein reaction formula 1. in R
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl,
be selected from C
1~ C
18alkylene or
in one, m is selected from the one in 1,2 or 3; Wherein said n is selected from the positive integer of 1 ~ 20;
The molar weight ratio of described general formula (IA) or the shown oxyamine of general formula (IB) and 5-chloromethyl salicylaldehyde is 1: 0.8 ~ 1.5;
Described solvent refers to acetone, butanone, 1,4-dioxane, tetrahydrofuran (THF), glycol dimethyl ether, ethylene glycol diethyl ether, toluene, dimethylbenzene, chlorobenzene, ethyl acetate, methyl acetate, butylacetate, chloroform, tetracol phenixin, 1,2-ethylene dichloride, methylcyclohexane, N, dinethylformamide, N, one or more in N-N,N-DIMETHYLACETAMIDE, methyl-sulphoxide or acetonitrile, described solvent load is 2 ~ 10 times of general formula (IA) or general formula (IB) and 5-chloromethyl salicylaldehyde quality summation;
Step 2 contains the polyvalent alcohol preparation of quaternary ammonium cation or Salen or salophen function base
Take quaternary ammonium salt containing salicylic aldehyde of the obtained general formula (IIA) of step one or general formula (IIB) respectively and organic two ammoniums are dissolved in dehydrated alcohol, control temperature of reaction at 25 ~ 85 DEG C, 6 ~ 24 hours reaction times, terminate reaction, revolve and steam the most of ethanol of removing, add organic solvent revolving to steam in remaining concentrated solution, cooling stratification, isolate lower floor's material, vacuum-drying, the polyvalent alcohol containing quaternary ammonium cation and Salen or salophen function base of obtained general formula (A) or the shown structure of general formula (B), shown in seeing that reaction formula is 2.:
Wherein said organic two ammoniums refer to has general formula H
2n-X-NH
2chemical structure; Wherein said X is selected from C
2~ C
10alkylene,
or the one in aromatic nucleus; Wherein said aromatic nucleus refers to the one in phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus, and described n is selected from the positive integer of 1 ~ 20;
Described reaction formula 2. in R
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl;
be selected from C
1~ C
18alkylene or
in one, m is selected from the one in 1,2 or 3; Wherein said n is selected from the positive integer of 1 ~ 20;
The consumption of described dehydrated alcohol is 5 ~ 10 times of quaternary ammonium salt containing salicylic aldehyde of general formula (IIA) or general formula (IIB) and organic two ammonium quality summations;
Described organic solvent refers to acetone, butanone, 1,4-dioxane, tetrahydrofuran (THF), ethyl acetate, butylacetate, chloroform, tetracol phenixin, 1, one or more in 2-ethylene dichloride or acetonitrile, the consumption of described organic solvent is 2 ~ 10 times of general formula (IIA) or general formula (IIB) and organic two ammonium quality summations.
Specific embodiment
By embodiment below, polyvalent alcohol containing quaternary ammonium cation and Salen or salophen function base of general formula provided by the invention (A) or general formula (B) and preparation method are further illustrated, its object is to understand content of the present invention better.Therefore, general formula (A) unlisted in embodiment or the shown structure of general formula (B) contain polyvalent alcohol and the preparation method of quaternary ammonium cation and Salen or salophen function base, should not be considered as limiting the scope of the invention.
Embodiment 1 contains the preparation of the polyvalent alcohol (1A) of quaternary ammonium cation and Salen function base
The preparation of step 1N, N-dimethyl-N-hydroxy-N-(3-aldehyde radical-4-hydroxybenzyl) ammonium chloride
In the four-hole boiling flask that agitator is housed, take 5-chloromethyl salicylaldehyde 34 grams and be dissolved in 80 milliliters of ethyl acetate, letting nitrogen in and deoxidizing, after 30 minutes, takes N, and N-dimethylethanolamine 20 grams is dissolved in 80 milliliters of ethyl acetate.Under room temperature, 5-chloromethyl salicylaldehyde solution is joined N, in the ethyl acetate solution of N-dimethylethanolamine, stir lower reaction after 4 hours, reaction mass temperature is brought up to 60 ~ 65 DEG C, stirring reaction 2 hours, is down to 5 ~ 10 DEG C by reaction product system temperature again, leaves standstill and separates lower floor, obtained light yellow crystal shape material, after ethyl alcohol recrystallization, obtaining light yellow crystal shape material 47.6 grams, is namely N, N-dimethyl N-hydroxyethyl N-(3-aldehyde radical-4-hydroxybenzyl) ammonium chloride, there is strong water absorbability, yield 93.2%, mp:171 ~ 172 DEG C; Ultimate analysis: C
12h
18clNO
3measured value (calculated value) C54.38 (55.49), H7.01 (6.99), N5.31 (5.39), C113.55 (13.65).IR analysis of spectra (KBr, cm
-1): 3343,3037,2937,2823,2721,1686,1557,1138,1032.H
1-NMR(D
2O，δ)：3.31(s，6H)，3.47～3.78(m，4H)，4.35(s，2H)，5.05(s，1H)，5.41(m，1H)，7.05～7.36(m，3H)，10.37(s，1H)。
Step 2 contains the preparation of the polyvalent alcohol (1A) of quaternary ammonium cation and Salen function base
Taking 5.8 grams of quadrols is dissolved in 100 milliliters of dehydrated alcohols, add the N that step one is obtained, N-dimethyl N-hydroxyethyl N-(3-aldehyde radical-4-hydroxybenzyl) ammonium chloride 47.6 grams, controlling temperature of reaction is 60 ~ 65 DEG C, constantly steam partially azeotropic thing, stirring reaction totally 20 hours, concentrated after terminating reaction, separate out light yellow crystal shape material after cooling after concentrated; Use dehydrated alcohol recrystallization, 50 DEG C of vacuum-dryings, obtained 50.7 grammeter looks contain the polyvalent alcohol (1A) of quaternary ammonium cation and Salen function base, yield 93.6%, fusing point 106 ~ 109 DEG C; Ultimate analysis: C
26h
40cl
2n
4o
4measured value (calculated value) C57.48 (57.45), H7.08 (7.42), N10.61 (10.31), Cl12.63 (13.04).IR analysis of spectra (KBr, cm-1): 3441,3305,3033,2928,2827,1603,1548,1446,1413,1106.H
1-NMR(D
2O，δ)：3.30(s，12H)，3.47～3.78(m，8H)，3.91(s，4H)，4.35(t，4H)，5.05(s，2H)，5.41(m，2H)，7.05～7.36(m，6H)，8.71(s，2H)。
Embodiment 2 contains the preparation of the polyvalent alcohol (2A) of quaternary ammonium cation and Salophen function base
According to method and the operation steps of embodiment 1, changed by the quadrol in embodiment 1 step 2 as O-Phenylene Diamine, the polyvalent alcohol (2A) containing quaternary ammonium cation and Salophen function base of obtained orange, is shown below:
Embodiment 3 contains the preparation of the polyvalent alcohol (3A) of quaternary ammonium cation and Salophen function base
According to method and the operation steps of embodiment 1, by the N in embodiment 1 step one, N-dimethylethanolamine changes as N methyldiethanol amine, quadrol in step 2 changes as O-Phenylene Diamine, the polyvalent alcohol (3A) containing quaternary ammonium cation and Salophen function base of obtained orange, is shown below:
Embodiment 4 contains the preparation of the polyvalent alcohol (4A) of quaternary ammonium cation and Salophen function base
According to method and the operation steps of embodiment 1, by the N in embodiment 1 step one, N-dimethylethanolamine changes as end dimethylamino triethylene Glycol, quadrol in step 2 changes as O-Phenylene Diamine, the polyvalent alcohol (4A) containing quaternary ammonium cation and Salophen function base of obtained orange, is shown below:
Embodiment 5 contains the preparation of the polyvalent alcohol (1B) of quaternary ammonium cation and Salen function base
According to method and the operation steps of embodiment 1, by the N in embodiment 1 step one, N-dimethylethanolamine changes the oxyamine (1b) for structure shown in formula (1b), it is 1 that quadrol in step 2 changes, 6-hexanediamine, the obtained flaxen polyvalent alcohol (1B) containing quaternary ammonium cation and Salen function base, is shown below:
Wherein the structural formula (1d) of oxyamine (1d) is:
Embodiment 6 contains the preparation of the polyvalent alcohol (2B) of quaternary ammonium cation and Salophen function base
According to method and the operation steps of embodiment 1, by the N in embodiment 1 step one, N-dimethylethanolamine changes the oxyamine for structure shown in formula (1d), quadrol in step 2 changes as O-Phenylene Diamine, the obtained bisque polyvalent alcohol (2B) containing quaternary ammonium cation and Salophen function base, is shown below:
Wherein the structural formula (1d) of oxyamine (1d) is:
Embodiment 7 contains the preparation of the polyvalent alcohol (3B) of quaternary ammonium cation and Salen function base
According to method and the operation steps of embodiment 1, by the N in embodiment 1 step one, it is the oxyamine shown in formula (1d) structure that N-dimethylethanolamine changes, it is the diamines shown in formula (3b) structure that quadrol in step 2 changes, the obtained flaxen polyvalent alcohol (3B) containing quaternary ammonium cation and Salen function base, is shown below:
Wherein the structural formula (1d) of oxyamine (1d) is:
(3b) diamine structures formula is:
Embodiment 8 contains the polyvalent alcohol physical property of quaternary ammonium cation and Salen or Salophen function base
In order to understand the performance and application of the polyvalent alcohol that the invention provides containing quaternary ammonium cation and Salen or Salophen function base further, table 1 lists the physical property containing quaternary ammonium cation and Salen or Salophen function polylol in embodiment 1 ~ 7, for the organic functions macromolecular material such as polymer dielectric, ion guide mould material, water suction antibacterial fiber, anion-cation exchange resin, immobilized metal catalytic material preparing unique construction provides reference.
Table 1 contains the physical property of quaternary ammonium cation and Salen or Salophen function polylol
Claims (2)
1. contain the polyvalent alcohol of quaternary ammonium cation and Salen or Salophen function base, it is characterized in that there is structure shown in general formula (A) or general formula (B):
R in its formula of (A) or general formula (B)
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl,
be selected from C
1~ C
18alkylene or
in one, X is selected from C
2~ C
10alkylene,
or the one in aromatic nucleus, m is selected from the one in 1,2 or 3; Wherein said aromatic nucleus refers to the one in phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus, and described n is selected from the positive integer of 1 ~ 20.
2., according to the preparation method of the polyvalent alcohol containing quaternary ammonium cation and Salen or Salophen function base according to claim 1, it is characterized in that realizing according to following preparation process:
The preparation of the quaternary ammonium salt of step one containing salicylic aldehyde
The oxyamine and the 5-chloromethyl poplar aldehyde that take structure shown in general formula (IA) or general formula (IB) respectively dissolve in a solvent, obtained described general formula (IA) or general formula (IB) hydroxylamine solutions and 5-chloromethyl salicylaldehyde solution, under room temperature, 5-chloromethyl salicylaldehyde solution is added in general formula (IA) or general formula (IB) hydroxylamine solutions, stirring reaction is after 2 ~ 6 hours, heat up 60 ~ 85 DEG C and continue stirring reaction 2 ~ 6 hours, reaction mass temperature is down to room temperature, standing separation, obtained general formula (IIA) or the shown structure of general formula (IIB) contain the quaternary ammonium salt of salicylic aldehyde, shown in seeing that reaction formula is 1.:
Wherein reaction formula 1. in R
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl;
be selected from C
1~ C
18alkylene or
in one, m is selected from the one in 1,2 or 3; Wherein said n is selected from the positive integer of 1 ~ 20;
The molar weight ratio of described general formula (IA) or the shown oxyamine of general formula (IB) and 5-chloromethyl salicylaldehyde is 1: 0.8 ~ 1.5;
Described solvent refers to acetone, butanone, 1,4-dioxane, tetrahydrofuran (THF), glycol dimethyl ether, ethylene glycol diethyl ether, toluene, dimethylbenzene, chlorobenzene, ethyl acetate, methyl acetate, butylacetate, chloroform, tetracol phenixin, 1,2-ethylene dichloride, methylcyclohexane, N, dinethylformamide, N, one or more in N-N,N-DIMETHYLACETAMIDE, methyl-sulphoxide or acetonitrile, the consumption of described solvent is 2 ~ 10 times of general formula (IA) or general formula (IB) and 5-chloromethyl salicylaldehyde quality summation;
Step 2 contains the polyvalent alcohol preparation of quaternary ammonium cation or Salen or salophen function base
Take quaternary ammonium salt containing salicylic aldehyde of the obtained general formula (IIA) of step one or general formula (IIB) respectively and organic two ammoniums are dissolved in dehydrated alcohol, control temperature of reaction at 25 ~ 85 DEG C, 6 ~ 24 hours reaction times, terminate reaction, revolve and steam the most of ethanol of removing, add organic solvent revolving to steam in remaining concentrated solution, cooling stratification, isolate lower floor's material, vacuum-drying, the polyvalent alcohol containing quaternary ammonium cation and Salen or salophen function base of obtained general formula (A) or the shown structure of general formula (B), shown in seeing that reaction formula is 2.:
Wherein said organic two ammoniums refer to has general formula H
2n-X-NH
2chemical structure; Wherein said X is selected from C
2~ C
10alkylene,
or the one in aromatic nucleus; Wherein said aromatic nucleus refers to the one in phenyl ring, pyridine ring, thiphene ring or naphthalene nucleus, and described n is selected from the positive integer of 1 ~ 20;
Described reaction formula 2. in R
1and R
2do not choose any or be selected from C respectively
1~ C
18one in alkyl,
be selected from C
1~ C
18alkylene or
in one, m is selected from the one in 1,2 or 3; Wherein said n is selected from the positive integer of 1 ~ 20;
The consumption of described dehydrated alcohol is 5 ~ 10 times of quaternary ammonium salt containing salicylic aldehyde of general formula (IIA) or general formula (IIB) and organic two ammonium quality summations;
Described organic solvent refers to acetone, butanone, 1,4-dioxane, tetrahydrofuran (THF), ethyl acetate, butylacetate, chloroform, tetracol phenixin, 1, one or more in 2-ethylene dichloride or acetonitrile, the consumption of described organic solvent is 2 ~ 10 times of general formula (IIA) or general formula (IIB) and organic two ammonium quality summations.
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| CN106012638A (en) * | 2016-05-23 | 2016-10-12 | 昆明理工大学 | Process for bleaching membrane-shaped M ([H4] salen) catalytic paper pulp |
| CN106012638B (en) * | 2016-05-23 | 2017-11-10 | 昆明理工大学 | Membranaceous M ([H4] salen) it is catalyzed the technique of association with pulp bleaching |
| CN109320680A (en) * | 2018-10-12 | 2019-02-12 | 淮海工学院 | A kind of multifunctional polyurethane prepolymer and preparation method thereof |
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