CN108047428A - A kind of low viscosity biuret polyisocyanate and its preparation method and application - Google Patents
A kind of low viscosity biuret polyisocyanate and its preparation method and application Download PDFInfo
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- CN108047428A CN108047428A CN201711186891.4A CN201711186891A CN108047428A CN 108047428 A CN108047428 A CN 108047428A CN 201711186891 A CN201711186891 A CN 201711186891A CN 108047428 A CN108047428 A CN 108047428A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/62—Y being a nitrogen atom, e.g. biuret
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a kind of low viscosity biuret polyisocyanate and preparation method thereof, it is 0.01 0.80 that the low viscosity biuret polyisocyanate, which includes uretdion and biuret groups and the molar ratio of the uretdion and biuret groups,.Its preparation method obtains oligomeric isocyanates of the part containing uretdion groups, then the reaction was continued in reaction system addition catalyst and water, obtains biuret polyisocyanate to be first catalyzed the dimerization reaction of diisocyanate using phosphine compound.Biuret polyisocyanate viscosity prepared by this method is low, and colourity is less than 20Hazen, significantly improves the conversion ratio of diisocyanate raw material.
Description
Technical field
The present invention relates to a kind of low viscosity biuret polyisocyanate and preparation method thereof, the low viscosity biuret gathers
Isocyanates can be used for polyurethane coating curing agent.
Background technology
Polyurethane coating is with the excellent performance such as wide, the good, strong adhesive force of flexibility of its construction temperature scope and former in automobile
The fields such as factory's paint, car refinishing paint, plastic paint, industrial paint, woodcare paint, leather dope have been widely used.Polyurethane coating
Mainly there are HDI, IPDI, TDI and XDI etc. with diisocyanate industrialization product, be divided into aliphatic isocyanates and aromatic series is different
Cyanate.Aliphatic isocyanates class curing agent yellowing resistance is good, and the isocyanate curing agent based on HDI is main currently on the market
For HDI trimer and HDI biurets both products, wherein flexibility and adhesive force based on HDI biuret films are especially tall and erect
More.
In recent years, the discharge capacity for reducing coating volatile organic compounds has become development trend, high solid coating
It is an important development direction for reducing coating volatile organic compounds discharge capacity, polyisocyanate and polyalcohol can be reduced
Viscosity, to prepare high solid bicomponent polyurethane coating.
Biuret polyisocyanate can generate by polyisocyanates and water, amine or in situ the reagent reacting of water and prepare,
But biuret viscosity prepared by common process is very high, it is necessary to be diluted use.Viscosity during 25 DEG C of HDI biurets is more than
8000cP, when use, are usually diluted with organic solvent, such as dimethylbenzene, ethylene glycol ether acetate, propylene glycol monomethyl ether acetic acid
Ester, ethyl acetate, isopropyl acetate, n-propyl acetate, butyl acetate, isobutyl acetate etc., this is obviously unfavorable for reducing organic
The discharge of compound.
Publication CN106084182A prepares biuret using water with polyisocyanates reaction, adds in during the reaction
N heterocyclic carbene metal complex compounds can inhibit biuret structure and decompose generation free monomer, and the HDI biuret products of preparation are steady
It is qualitative good, but the viscosity of product is very high to be contained admittedly, it is necessary to be diluted to 75% using esters, ketone and aromatic hydrocarbon equal solvent
Amount, during use the volatilization of organic solvent be unfavorable for the healthy and environmentally friendly of human body.
Bayer patents US3976622 prepares low by adjusting the reaction molar ratio of diisocyanate and biuretized reagent
Viscosity biuret polyisocyanate is, it is necessary to control the molar ratio of diisocyanate and the biuretized reagent of single functionality to be at least
11:1.The essence of this method is to control the conversion ratio of diisocyanate, in diisocyanate and the biuretized reagent of single functionality
Molar ratio be at least 11:Under conditions of 1, there is substantial amounts of diisocyanate monomer to have neither part nor lot in reaction, it is necessary to be separated and returned
With processing, additional energy consumption is necessarily caused.
Asahi house journals US4388245 discloses the work that high-temperature heating method prepares low viscosity biuret polyisocyanate
Skill, the thermal sensitivity based on biuret structure, diisocyanate and high viscosity biuret are with mass ratio 1:2 are blended in 100-200 DEG C
Lower heating, the molecular weight distribution of high viscosity biuret are moved to the direction for being conducive to generate oligomer, isolate unreacted two
To get to the biuret product of low viscosity after isocyanate-monomer.But high viscosity biuret polyisocyanate is in high temperature item
It is synthesized under part, then by high-temperature heating it is made to resolve into low viscosity biuret, this process is obviously very uneconomical, and high temperature adds
Low viscosity biuret polyisocyanate product color number after heat is higher.
Bayer patents US4837359 reports diisocyanate and preparation contracting is reacted at a temperature of higher than 250 DEG C with diamines
Two urea polyisocyanate, this method can prepare the relatively low biuret polyisocyanate of viscosity, and product color number is relatively low.It is but big
The gaseous state diamines of flow is difficult to realize in the actual production process, and the reactivity of diamines and isocyanates is very high, very
Difficulty controls the reaction from technique.
During existing common process prepares low viscosity biuret polyisocyanate, all there are it is certain the defects of, lead to
The relatively low product of viscosity can excessively be prepared significantly by crossing control diisocyanate, but this method is related to largely having neither part nor lot in instead
Separation and reuse problem, the energy consumption for answering diisocyanate monomer are very high；By high-temperature heating method prepare low viscous biuret gather it is different
Cyanate can cause final products color number higher.
The content of the invention
It is an object of the invention to make up the deficiencies in the prior art, a kind of system of low viscosity biuret polyisocyanate is provided
Preparation Method.The biuret polyisocyanate viscosity obtained by the method is low, and colourity is less than 20Hazen, significantly improves simultaneously
The conversion ratio of diisocyanate raw material, low energy consumption.
It is another object of the present invention to provide a kind of low viscosity biuret polyisocyanate, range of viscosities is
1500-5000cP (25 DEG C), can be used for the curing agent of polyurethane coating.
To achieve the above objectives, the present invention adopts the following technical scheme that：
A kind of low viscosity biuret polyisocyanate includes uretdion and biuret groups and the uretdion and contracting two
The molar ratio of urea groups is 0.01-0.80, preferably 0.02-0.60.Its viscosity is 1500-5000cP (25 DEG C).
A kind of preparation method of low viscosity biuret polyisocyanate, including first phosphine compound being used to be catalyzed diisocyanate
The dimerization reaction of ester, then carboxylic acid catalyst is added in intermediate product, water is passed through after heating, and the reaction was continued, obtain biuret gather it is different
Cyanate.
As a kind of specific scheme, method of the invention comprises the steps of：
(1) under nitrogen protection, diisocyanate is added in reaction vessel, is heated to 20-130 DEG C, stirring condition
It is lower to add in a certain amount of catalyst, carry out dimerization reaction；
(2) a certain amount of carboxylic acid is added in after when reaction progress 0.5-6 is small, 80-220 DEG C is warming up to, starts to be slowly added to water
Carry out it is biuretized reaction 0.5-7 it is small when (the addition time i.e. reaction time in the stage of water), obtain biuret reaction liquid；
(3) the biuret reaction liquid that step (2) obtains enters demonomerization in separator, and the biuret for obtaining low viscosity gathers
Isocyanate products.
In the method for the present invention, uretdion and biuret groups, uretdion and contracting two are contained in biuret polyisocyanate
The molar ratio of urea groups is 0.01-0.80, preferably 0.02-0.60.
In the method for the present invention, in the dimerization reaction stage, the conversion ratio of diisocyanate monomer is 3-30%, preferably 5-25%.
The temperature in diisocyanate dimerization reaction stage is 20-130 DEG C, preferably 40-110 DEG C；When reaction time is 0.5-6 small, preferably
When 1-5 is small.The conversion ratio of the stage of reaction diisocyanate monomer is controlled in the scope, and the viscosity of final products is low,
Comprehensive performance is optimal.
In the method for the present invention, the dimerization reaction of diisocyanate carries out in the presence of phosphine catalyst, and the phosphine is urged
Agent is selected from amino substitution phosphine, trialkyl phosphine, cycloalkyl phosphine, preferably amino substitution phosphine, such as three (dimethylamino) phosphines, three (two
Ethylamino) phosphine, most preferably three (dimethylamino) phosphines；Based on diisocyanate monomer Mass Calculation, the dosage of phosphine catalyst is
0.02-4wt%, preferably 0.05-3wt%.
In the method for the present invention, the reaction of oligomeric isocyanates and water carries out under carboxylic acid catalysis, and the carboxylic acid is preferred
One or more in formic acid, acetic acid, propionic acid, pivalic acid, ethanedioic acid and malonic acid；Based on diisocyanate monomer quality meter
It calculates, the dosage of carboxylic acid catalyst is 0.05-5wt%, preferably 0.08-4wt%.Inventor is had found by studying reaction mechanism, is somebody's turn to do
The carboxylic acid compound that the stage of reaction adds in can not only terminate the dimerization reaction of diisocyanate monomer, but also can be catalyzed isocyanates
With the reaction of water, the uretdion groups of generation will not decompose in the pyroreaction stage.
In the method for the present invention, the molar ratio of the diisocyanate monomer and water is 4:1-19:1, preferably 6:1-18:1；
Biuretized reaction temperature is 80-220 DEG C, preferably 100-200 DEG C；When reaction time is 0.5-7 small, when preferably 0.8-6 is small.
In the method for the present invention, the diisocyanate be aliphatic diisocyanate and/or alicyclic diisocyanate,
It is preferred that hexamethylene diisocyanate, 1,4- cyclohexane diisocyanates, 4,4 '-dicyclohexyl methyl hydride diisocyanate and different Buddhist
The one or more of your ketone diisocyanate, more preferable isophorone diisocyanate.
In the method for the present invention, the conversion ratio of entire reaction process diisocyanate monomer is 32-80%, preferably 35-70%.
In the method for the present invention, the separator is thin film evaporator, and the separation temperature of thin film evaporator is controlled in 95-
220 DEG C, separation absolute pressure control is in 1-500Pa.
In the method for the present invention, the thin film evaporator scrapes membrane system for roller type knifing system membrane evaporator or scraper-type
System thin film evaporator.
The low viscosity biuret polyisocyanate of the present invention can be used to prepare double-component polyurethane coating as curing agent.
The positive effect of the present invention is：Conventional biuret polyisocyanate product viscosity is very high, and when use is usually used
Organic solvent is diluted, such as dimethylbenzene, ethylene glycol ether acetate, propylene glycol methyl ether acetate, ethyl acetate, isopropyl acetate
Ester, n-propyl acetate, butyl acetate, isobutyl acetate etc., the volatilization of organic solvent are unfavorable for the healthy and environmentally friendly of human body.At present
The conversion ratio of technique diisocyanate monomer is than relatively low, it is necessary to separate and a large amount of unreacted diisocyanate list of Treatment for Reuse
Body causes very high energy consumption.The present invention is before water and isocyanates reaction prepare biuret polyisocyanate, first using phosphine
The dimerization reaction of class compound for catalysis diisocyanate obtains oligomeric isocyanates of the part containing uretdion groups, containing urea two
The oligomeric isocyanates of ketone groups can reduce the viscosity of biuret polyisocyanate, improve water and the isocyanates stage of reaction two
The conversion ratio of isocyanates, the biuret polyisocyanate viscosity of preparation is low, and colourity is less than 20Hazen.With the method for the present invention
The biuret polyisocyanate of preparation is particularly suitable for the curing agent that down stream customer is directly used as in coatings industry, need not be with organic
Solvent is diluted.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail, but therefore the present invention is not subject to
Any restrictions.
The color number of biuret polyisocyanate is tested using BYK LCS IV color instrument, is tested using Hazen colour codes.
It is carried out using gel chromatography (5 μm of chromatographic column MZ-Gel SDplus10E3A, 35 DEG C, mobile phase tetrahydrofuran, 1.0mL/min)
Isocyanates raw material quantitative, as the monitoring means for judging reaction conversion ratio (being calculated based on isocyanate).Viscosity uses
Brookfield viscosimeters test (model RVDV-II+P, 25 DEG C).
The molar ratio of uretdion and biuret groups is adopted in gained biuret polyisocyanate in embodiment and comparative example
It is represented with U/B, test method uses13C-NMR nuclear magnetic resonance methods use instrument as Bruker400MHz instruments, sample concentration
For 50% (CDCl3Solution), test condition 100MHz, slack time：4sec, min2000 scanning, with δ=77.0ppm
CDCl3As displacement reference.
In the case of not doing specified otherwise, before reaction into addition catalyst and entire reaction process, reaction system one
Under the straight protection in drying nitrogen.
Embodiment 1
1) 2223g (10mol) isophorone diisocyanate is added in four-hole boiling flask, is warming up to 40 DEG C, stirring condition
It is lower to add in three (dimethylamino) phosphines of 1.1g, and start clock reaction；
2) after when reaction 1 is small, conversion ratio as defined in arrival adds the 4wt%'s based on isophorone diisocyanate amount
Pivalic acid is warming up to 110 DEG C, is slowly added to 12.9g water, be stirred to react 2 it is small when；
3) the biuret reaction liquid that step (2) obtains passes through the isolated low viscosity of roller type knifing system membrane evaporator
Biuret polyisocyanate product, separation temperature are 170 DEG C, and separation absolute pressure is 400Pa.
Embodiment 2-4 process conditions are same as Example 1, the difference is that only three (dimethylamino) phosphines addition and
The reaction time in dimerization reaction stage, specifying information are shown in Table 1.
Comparative example 1
1) 2223g (10mol) isophorone diisocyanate is added in four-hole boiling flask, addition is different based on isophorone two
The pivalic acid of the 4wt% of cyanate amount is warming up to 110 DEG C, is slowly added to 15.8g water, be stirred to react 2 it is small when；
2) the biuret reaction liquid that step (1) obtains passes through the isolated low viscosity of roller type knifing system membrane evaporator
Biuret polyisocyanate product, separation temperature are 170 DEG C, and separation absolute pressure is 400Pa.
The specifying information of 1 embodiment 1-4 of table and comparative example 1
Embodiment 5
1) 1680g (10mol) hexamethylene diisocyanate is added in four-hole boiling flask, is warming up to 70 DEG C, stirring condition
Lower addition 16.8g tri- (dimethylamino) phosphine, and start clock reaction；
2) after when reaction 4 is small, conversion ratio as defined in arrival, the propionic acid of the 2wt% of addition hexamethylene diisocyanate amount,
Be warming up to 190 DEG C, be slowly added to 36g water, be stirred to react 6 it is small when；
3) the biuret reaction liquid that step (2) obtains passes through the isolated low viscosity of scraper-type knifing system membrane evaporator
Biuret polyisocyanate product, separation temperature are 100 DEG C, and separation absolute pressure is 100Pa.
Embodiment 6-8 process conditions are same as Example 5, the difference is that only the addition of propionic acid and the addition of water
Amount, specifying information are shown in Table 2.
Comparative example 2 is similar to Example 5, the difference is that the addition of water, specifying information are shown in Table 2.
The specifying information of 2 embodiment 5-8 of table and comparative example 2
The result shows that：The dimerization reaction of diisocyanate is first catalyzed using phosphine compound, by controlling the addition of water,
The biuret polyisocyanate product of low viscosity can be prepared, colourity is less than 20Hazen.
Claims (11)
1. a kind of low viscosity biuret polyisocyanate, which is characterized in that include uretdion and biuret groups and the urea two
The molar ratio of ketone group and biuret groups is 0.01-0.80, preferably 0.02-0.60.
2. the preparation method of low viscosity biuret polyisocyanate according to claim 1, includes the following steps：Two is different
Dimerization reaction first occurs for cyanate, obtains oligomeric isocyanates of the part containing uretdion groups, is then added in reaction system
Catalyst and water carry out biuretized reaction, generate biuret polyisocyanate.
3. preparation method according to claim 2, which is characterized in that dimerization reaction stage, diisocyanate monomer turn
Rate is 3-30%, preferably 5-25%.
4. the preparation method according to Claims 2 or 3, which is characterized in that entire reaction process diisocyanate monomer
Conversion ratio is 32-80%, preferably 35-70%.
5. according to the preparation method any one of claim 2-4, which is characterized in that the dimerization reaction of diisocyanate exists
It is carried out in the presence of phosphine catalyst, the phosphine catalyst is selected from amino substitution phosphine, trialkyl phosphine, preferably cycloalkyl phosphine, ammonia
Base substitutes phosphine, such as three (dimethylamino) phosphines, three (lignocaine) phosphines, more preferable three (dimethylamino) phosphine；Based on diisocyanate
Ester monomer Mass Calculation, the dosage of phosphine catalyst is 0.02-4wt%, preferably 0.05-3wt%.
6. according to the preparation method any one of claim 2-5, which is characterized in that the diisocyanate dimerization reaction stage
Temperature be 20-130 DEG C, preferably 40-110 DEG C；When reaction time is 0.5-6 small, when preferably 1-5 is small.
7. according to the preparation method any one of claim 2-6, which is characterized in that the biuretized reaction is urged
Agent is carboxylic acid, preferably the one or more in formic acid, acetic acid, propionic acid, pivalic acid, ethanedioic acid and malonic acid；Based on two isocyanides
Acid ester monomer Mass Calculation, the dosage of catalyst is 0.05-5wt%, preferably 0.08-4wt%.
8. according to the preparation method any one of claim 2-7, which is characterized in that diisocyanate monomer and water rub
You are than being 4:1-19:1, preferably 6:1-18:1.
9. according to the preparation method any one of claim 2-8, which is characterized in that the reaction temperature of biuretized reaction
For 80-220 DEG C, preferably 100-200 DEG C；When reaction time is 0.5-7 small, when preferably 0.8-6 is small.
10. according to the preparation method described in claim 2-9, which is characterized in that the diisocyanate is different for aliphatic two
Cyanate and/or alicyclic diisocyanate, preferably hexamethylene diisocyanate, Isosorbide-5-Nitrae-cyclohexane diisocyanate, 4,4 '-
The one or more of dicyclohexyl methyl hydride diisocyanate and isophorone diisocyanate, more preferable isophorone diisocyanate
Ester.
11. any one of low viscosity biuret polyisocyanate according to claim 1 or claim 2-10 preparation side
The low viscosity biuret polyisocyanate that method obtains is used to prepare double-component polyurethane coating as curing agent.
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| CN111040101A (en) * | 2019-12-23 | 2020-04-21 | 万华化学集团股份有限公司 | Polyisocyanate having stable color number and containing uretdione group and preparation method thereof |
| CN111217972A (en) * | 2020-01-13 | 2020-06-02 | 万华化学集团股份有限公司 | Preparation method of biuret polyisocyanate with storage stability |
| WO2020133067A1 (en) * | 2018-12-26 | 2020-07-02 | 万华化学集团股份有限公司 | Method for preparing polyisocyanate containing uretdione group |
| CN114507332A (en) * | 2020-11-16 | 2022-05-17 | 万华化学（宁波）有限公司 | Polyisocyanate containing biuret structure and preparation method thereof |
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| CN111217972B (en) * | 2020-01-13 | 2022-02-15 | 万华化学集团股份有限公司 | Preparation method of biuret polyisocyanate with storage stability |
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| CN114507332B (en) * | 2020-11-16 | 2024-02-27 | 万华化学（宁波）有限公司 | Polyisocyanate containing biuret structure and preparation method thereof |
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