CN102503909A - Compound containing tertiary amine derivatives, preparation method and application thereof - Google Patents
Compound containing tertiary amine derivatives, preparation method and application thereof Download PDFInfo
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- CN102503909A CN102503909A CN2011103707627A CN201110370762A CN102503909A CN 102503909 A CN102503909 A CN 102503909A CN 2011103707627 A CN2011103707627 A CN 2011103707627A CN 201110370762 A CN201110370762 A CN 201110370762A CN 102503909 A CN102503909 A CN 102503909A
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Abstract
The invention relates to a compound containing tertiary amine derivatives and a preparation method. The derivatives can be used as the formula components of a catalyst and a binder for synthesizing polyurethane. The invention provides a method for synthesizing the compound containing the tertiary amine derivatives. The method comprises the following steps: mixing ethylene carbonate or urea with NH2XNR2 at a mass ratio of 1: 2; performing a constant temperature backflow reaction at 100-140 DEG C and under the condition of introducing N2 as protective gas; and separating and purifying the obtained product, thereby obtaining the compound containing the tertiary amine derivatives. When the compound is taken as the catalyst for synthesizing the polyurethane, the catalytic activity is higher. The compound is higher in boiling point, lower in toxicity and wider in application prospect.
Description
Technical field
The invention belongs to the fine chemicals field, relate to a kind of tertiary amine urea derivatives compounds that contains.
Background technology
Before 1958, prepolymer method is all adopted in urethane foam production, promptly so-called two step method.After this, because triethylene diamine and stannous octoate are the appearance of two types of catalyzer of representative, the single stage method foaming is able to rapid popularization.
Catalyst of polyurethane is mainly amine and organo-metallic class, and these two types of catalyzer all belong to the retardance catalyzer.These catalyzer can also be controlled the physical and mechanical properties and the technical data of the speed of relative movement of parallel reactor, the flowability that influences reaction mixture, finished product except can accelerated reaction.Wherein amine belongs to the nucleophilicity catalyzer, and it is main often it being regarded as with the catalysis foamable reaction in the industry.The organo-metallic class belongs to the Electron Affinities catalyzer, and it is main often it being regarded as with the catalysis gel reaction in the industry.Because amines catalyst structurally variable property is big, wide in variety, can influence foaming, gel, curing and the trimerization reaction of urethane, performance is very excellent.The aminated compounds of useful as catalysts is more than organo-metallic platform species simultaneously, so amines catalyst is the catalyzer that people are most interested in always.
Tertiary amine catalyst commonly used has: triethylenediamine, two-(dimethylaminoethyl) ether, N-alkyl morpholine etc.Triethylene diamine has another name called triethylenediamine, triethylenediamine, is succeeded in developing and commercialization by U.S. air Products Co., Ltd the earliest.As the polyurethane foam catalyzer, it is used for various goods such as soft bubble, semihard steep, hard bubble, elastomerics.Be to use the widest, the maximum tertiary amine catalyst of consumption in the polyurethane industrial.But that these article exist is inflammable, be corrosive, be shortcoming such as solid-state under the normal temperature.Other tertiary amine catalyst ubiquity smell is big, etching apparatus or application surface is narrow, catalytic activity is low shortcoming.As: N-methylmorpholine, triethylamine etc. are replaced with regard to overpowering odor is arranged owing to volatilizing on a small quantity gradually, and N, N-dimethyl cyclohexyl amine are mainly used in catalysis and generate rigid urethane foam, and the dimethylethanolamine catalytic activity is far below triethylenediamine.
Summary of the invention
Technical problem to be solved by this invention is some problems that exist to the amines catalyst that is used for synthesis of polyurethane at present, and one type of catalytic activity height and good stability, the amines catalyst little to equipment corrosion are provided.
Technical scheme provided by the invention is: contain tertiary amine urea derivatives compounds, its structural formula does
In the formula: X is C
2~ C
3Alkyl chain, R is C
1~ C
4Alkyl chain or two R on the same N atom be connected to become a C
4Linear alkyl chain and form five yuan of pyrrole rings with this N atom.
The present invention also provides the above-mentioned preparation method who contains tertiary amine urea derivatives compounds.
The preparation method one: with NSC 11801 and NH
2XNR
2Press the proportioning of amount of substance 1:2 and mix, 100 ℃ ~ 140 ℃ with the reaction of nitrogen protection refluxed, can make the present invention relates to contain tertiary amine urea derivatives compounds.The chemical equation of this method is following:
The preparation method two: with urea and NH
2XNR
2Press the proportioning of amount of substance 1:2 and mix, if urea is at NH
2XNR
2In can't dissolve, can in above-mentioned mixed system, add pure water with quality such as urea as solubility promoter.100 ℃ ~ 140 ℃ with nitrogen protection refluxed reaction, can make the present invention relates to contain tertiary amine urea derivatives compounds.Draw the NH of generation in the reaction process several times
3Can effectively improve reaction conversion ratio.The chemical equation of this method is following:
Compound of the present invention can be used as the catalyzer of generation urethane foam and the recipe ingredient of tackiness agent.
As the urethane foam catalyzer, its dosage is 0.4% ~ 2.0% of a raw material heavy amount.
The urea derivatives compounds normal temperature that the present invention relates to is colourless or light yellow transparent liquid down; Do not contain solid substance; Can be to not making production of polyurethane equipment deleterious impact, catalyzer of also having avoided being solid-state under some normal temperature such as triethylenediamine need be mixed with solution and add the problem of going in the reaction system to; This urea derivatives compounds boiling point is very high in addition, is difficult to volatilization, and the interpolation that has solved because of amines catalyst causes urethane foam or the excessive problem of tackiness agent smell.Through a large amount of research and comparison, a prevailing paradigm about urethane amines catalyst foaming catalytic activity height is at present: N atoms in space steric hindrance is more little, and its alkalescence is strong more, thereby catalytic activity is high more.Through choosing suitable reaction raw materials, can regulate the activity of atom of tertiary amine N in the urea derivatives class of the present invention, thereby play the effect of control urethane synthesis process.
Embodiment
The present invention is with NSC 11801 or urea and NH
2XNR
2Press the proportioning of amount of substance 1:2 and mix, determine whether to add appropriate solvent according to the intermiscibility of two kinds of reactants, 100 ℃ ~ 140 ℃ oil baths with feed N
2As constant temperature back flow reaction 24 hours under the condition of protection gas, the product that obtains promptly makes the purified tertiary amine urea derivatives compounds that contains through separation and purification.
Embodiment 1
In 100mL single port flask, add 2.2 gram vinyl carbonates, slowly Dropwise 5 .8 restrains N, N-diethyl ethylenediamine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 120 ℃ of stirring and refluxing reactions.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.Adopt the HPLC-MS coupling technique to analyze to aforesaid liquid; Under the ESI-pattern, detect mass-to-charge ratio and be 258 peak, mass-to-charge ratio and be 257 molecular ion peak and mass-to-charge ratio and be 158 main fragment ion peak, analyze in conjunction with the reactant of this reaction and possible product and relatively can confirm to contain in the resultant [(C
2H
5)
2NCH
2CH
2NH]
2CO.
Embodiment 2
With 4.2 gram α, α '-dimethylol propionic acid is dissolved in 86 gram polyoxypropylene diols and transferring in the round-bottomed flask of 250mL, slowly drips 29 gram tolylene diisocyanates again, in 80 ℃ of following stirring reactions 24 hours, processes performed polymer.
[(C2H5) 2NCH2CH2NH] 2CO of preparation among the embodiment 1 is taken by weighing 4.2 grams is dissolved in the 220 gram pure water, stir and to add above-mentioned performed polymer down, and continue to stir 4 hours white emulsion.Under agitation in emulsion, add 22 gram ROHM as thickening material, add 60 gram pure water again, stir and to make tackiness agent W in two hours.This tackiness agent glue-line snappiness is good, can be used for bonding between porous plastics.
Embodiment 3
In 100mL single port flask, add 1.5 gram ureas, slowly Dropwise 5 .7 restrains N-(2-amino-ethyl) tetramethyleneimine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 140 ℃ of stirring and refluxing reactions, and extracts the ammonia that reaction produces out with vacuum pump respectively after 2 hours, after 4 hours, after 8 hours, after 18 hours, after 20 hours, and in time charge into nitrogen in the reaction beginning.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained colourless transparent viscous liquid.The productive rate that reacts under this condition is 88.3%.Adopt the HPLC-MS coupling technique to analyze to aforesaid liquid; Under the ESI-pattern, detect mass-to-charge ratio and be 254 peak, mass-to-charge ratio and be 253 molecular ion peak and mass-to-charge ratio and be 156 main fragment ion peak, analyze the product that relatively can confirm to contain in the resultant following structure in conjunction with the reactant and the possible product of this reaction:
Embodiment 4
In 100mL single port flask, add 1.5 gram ureas, slowly Dropwise 5 .7 restrains N-(2-amino-ethyl) tetramethyleneimine again.Flask is placed oil bath pan, connect spherical condensation tube, oil bath temperature is elevated to 140 ℃ of stirring and refluxing reactions.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained jonquilleous transparent viscous liquid.A wide and flat assorted peak is arranged near the chemical shift of Wasserstoffatoms on the hydrogen nuclear magnetic resonance spectrogram secondary amine of this batch product; Two [N-(2-amino-ethyl) pyrroles] ureas that show generation are by partially oxidation; Product is glassy yellow can explain that also product is easily by airborne dioxygen oxidation under the situation of not using inertia protection gas.
Embodiment 5
In 100mL single port flask, add 1.5 gram ureas, slowly drip 8.1 gram N again, N-di-n-butyl quadrol.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 100 ℃ of stirring and refluxing reactions, and extracts the ammonia that reaction produces out with vacuum pump respectively after 2 hours, after 4 hours, after 8 hours, after 18 hours, after 20 hours, and in time charge into nitrogen in the reaction beginning.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.The productive rate that reacts under this condition is 79.3%.Adopt the HPLC-MS coupling technique to analyze to aforesaid liquid; Under the ESI-pattern, detect mass-to-charge ratio and be 350 peak, mass-to-charge ratio and be 349 molecular ion peak and mass-to-charge ratio and be 204 main fragment ion peak, analyze in conjunction with the reactant of this reaction and possible product and relatively can confirm to contain in the resultant [(CH
3CH
2CH
2CH
2)
2NCH
2CH
2NH]
2CO.
Embodiment 6
In 100mL single port flask, add 1.5 gram urea and 2mL water, slowly Dropwise 5 .1 restrains the 3-dimethylaminopropylamine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 100 ℃ of stirring and refluxing reactions, and extracts the ammonia that reaction produces out with vacuum pump respectively after 2 hours, after 4 hours, after 8 hours, after 18 hours, after 20 hours, and in time charge into nitrogen in the reaction beginning.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.The productive rate that reacts under this condition is 83.5%.
Embodiment 7
In 100mL single port flask, add 1.5 gram urea and 5mL YLENE, slowly Dropwise 5 .1 restrains the 3-dimethylaminopropylamine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 140 ℃ of stirring and refluxing reactions, and extracts the ammonia that reaction produces out with vacuum pump respectively after 2 hours, after 4 hours, after 8 hours, after 18 hours, after 20 hours, and in time charge into nitrogen in the reaction beginning.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.The productive rate that reacts under this condition is 86.9%.
Embodiment 8
In 100mL single port flask, add 1.5 gram ureas, slowly Dropwise 5 .1 restrains the 3-dimethylaminopropylamine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 120 ℃ of stirring and refluxing reactions, and extracts the ammonia that reaction produces out with vacuum pump respectively after 2 hours, after 4 hours, after 8 hours, after 18 hours, after 20 hours, and in time charge into nitrogen in the reaction beginning.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.The productive rate that reacts under this condition is 92.6%.
Embodiment 9
In 100mL single port flask, add 1.5 gram ureas, slowly Dropwise 5 .1 restrains the 3-dimethylaminopropylamine again.Flask is placed oil bath pan, connect spherical condensation tube and Y-junction, extract intrasystem air out, and charge into nitrogen as protection gas with vacuum pump.Oil bath temperature is elevated to 120 ℃ of stirring and refluxing reactions.Stopped reaction after 24 hours is treated after the product cooling product rotary evaporation 1 hour under 90 ℃ of conditions that vacuumize is obtained almost colourless transparent viscous liquid.The productive rate that reacts under this condition is 80.2%.Resultant liquid to embodiment 6 ~ 9 adopts the HPLC-MS coupling technique to analyze; Under the ESI-pattern, detect mass-to-charge ratio and be 230 peak, mass-to-charge ratio and be 229 molecular ion peak and mass-to-charge ratio and be 144 main fragment ion peak, analyze in conjunction with the reactant of this reaction and possible product and relatively can confirm to contain in the resultant [(CH
3)
2NCH
2CH
2CH
2NH]
2CO.The resultant proton nmr spectra data of embodiment 6 as shown in table 1 have also confirmed above-mentioned judgement, and the proton nmr spectra of embodiment 7 ~ 9 is almost completely the same with embodiment 6 splitting on the branch situation of chemical shift, peak, and are just slightly different on the ratio of peak area.
The proton nmr spectra data of table 1 embodiment 6 resultants
| Chemical shift | Split the branch situation | Peak area | The Wasserstoffatoms number | Corresponding Wasserstoffatoms position |
| 5.824 | m | 2.16 | 2 | —N H— |
| 3.202 | s | 4.79 | 4 | —C H 2NH— |
| 2.333 | t | 4.09 | 4 | —C H 2N(CH 3) 2 |
| 2.202 | q | 16.36 | 12 | —N(C H 3) 2 |
| 1.639 | s | 5.19 | 4 | —CH 2C H 2CH 2— |
Embodiment 10
Two [N-(2-amino-ethyl) pyrroles] ureas of synthetic among the embodiment 3 as as catalyzer, are tested the catalytic performance of its this catalyzer that accounts for raw material total mass mark 0.4% in the reaction of polyether glycol 4110 and polymethylene multi-phenenyl isocyanate.Concrete proportioning raw materials is seen table 2 numbering 1 with the foaming parameter, and the material temperature control is at 31 ~ 32 ℃ during reaction.
Embodiment 11
Two [N-(2-amino-ethyl) pyrroles] ureas of synthetic among the embodiment 3 as as catalyzer, are tested the catalytic performance of its this catalyzer that accounts for raw material total mass mark 0.6% in the reaction of polyether glycol 4110 and polymethylene multi-phenenyl isocyanate.Concrete proportioning raw materials is seen table 2 numbering 2 with the foaming parameter, and the material temperature control is at 31 ~ 32 ℃ during reaction.
Two [N-(2-amino-ethyl) pyrroles] urea catalytic performances (hard bubbling) of table 2 different concns
Embodiment 12
Two [N-(2-amino-ethyl) pyrroles] ureas of synthetic among the embodiment 3 as as catalyzer, are tested the catalytic performance of its this catalyzer that accounts for raw material total mass mark 1.0% in the reaction of polyether glycol 4110 and polymethylene multi-phenenyl isocyanate.Concrete proportioning raw materials is seen table 2 numbering 3 with the foaming parameter, and the material temperature control is at 31 ~ 32 ℃ during reaction.
Embodiment 13
Two [N-(2-amino-ethyl) pyrroles] ureas of synthetic among the embodiment 3 as as catalyzer, are tested the catalytic performance of its this catalyzer that accounts for raw material total mass mark 1.5% in the reaction of polyether glycol 4110 and polymethylene multi-phenenyl isocyanate.Concrete proportioning raw materials is seen table 2 numbering 4 with the foaming parameter, and the material temperature control is at 31 ~ 32 ℃ during reaction.
Embodiment 14
Two [N-(2-amino-ethyl) pyrroles] ureas of synthetic among the embodiment 3 as as catalyzer, are tested the catalytic performance of its this catalyzer that accounts for raw material total mass mark 2.0% in the reaction of polyether glycol 4110 and polymethylene multi-phenenyl isocyanate.Concrete proportioning raw materials is seen table 2 numbering 5 with the foaming parameter, and the material temperature control is at 31 ~ 32 ℃ during reaction.
Claims (4)
1. contain tertiary amine urea derivatives compounds, it is characterized in that having following structural formula:
In the formula: X is C
2~ C
3Alkyl chain, R is C
1~ C
4Alkyl chain or two R on the same N atom be connected to become a C
4Linear alkyl chain and form five yuan of pyrrole rings with this N atom.
2. the described preparation method who contains tertiary amine urea derivatives class of claim 1 is characterized in that, with NSC 11801 or urea and NH
2XNR
2Press the proportioning of amount of substance 1:2 and mix, at 100 ℃ ~ 140 ℃ and feeding N
2As constant temperature back flow reaction under the condition of protection gas, the product that obtains promptly makes through separation and purification and contains tertiary amine urea derivatives compounds.
3. the described tertiary amine urea derivatives compounds that contains of claim 1 is characterized in that as the urethane foam catalyzer its dosage is 0.4% ~ 2.0% of a raw material total mass.
4. the described recipe ingredient that contains tertiary amine urea derivatives compounds as tackiness agent of claim 1.
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Cited By (6)
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| DE102014215382A1 (en) * | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Nitrogen containing compounds suitable for use in the production of polyurethanes |
| DE102014215384A1 (en) * | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Nitrogen containing compounds suitable for use in the production of polyurethanes |
| WO2016020201A1 (en) * | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Nitrogen-containing compounds suitable for use in the production of polyurethanes |
| WO2016020200A1 (en) * | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Nitrogen-containing compounds suitable for use in the production of polyurethanes |
| CN109705305A (en) * | 2018-12-11 | 2019-05-03 | 万华化学集团股份有限公司 | Contain how unsaturated group isocyanates biuret and its preparation and application |
| CN109942463A (en) * | 2019-04-25 | 2019-06-28 | 湖北和昌新材料科技股份有限公司 | A kind of synthetic method of bis- [3- (dimethylamino) propyl] ureas of 1,3- |
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Cited By (10)
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Application publication date: 20120620 |