CN107236108A - The preparation method of aqueous polyurethane acrylate - Google Patents
The preparation method of aqueous polyurethane acrylate Download PDFInfo
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- CN107236108A CN107236108A CN201710580293.9A CN201710580293A CN107236108A CN 107236108 A CN107236108 A CN 107236108A CN 201710580293 A CN201710580293 A CN 201710580293A CN 107236108 A CN107236108 A CN 107236108A
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
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- C—CHEMISTRY; METALLURGY
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- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3278—Hydroxyamines containing at least three hydroxy groups
- C08G18/3281—Hydroxyamines containing at least three hydroxy groups containing three hydroxy groups
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy groups
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- 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
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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Abstract
The invention discloses a kind of aqueous polyurethane acrylate preparation method, it is first by diisocyanate and the carboxylic acid containing two hydroxyls, reaction obtains holding the polyurethane prepolymer of isocyano, then three-functionality-degree polyol prepolymer is added dropwise, and reaction obtains holding isocyano polyurethane prepolymer；Then pentaerythritol triacrylate is added dropwise, reaction obtains the polyurethane acrylate prepolymer of acrylate ended；Then the reactant aqueous solution for adding tertiary amine obtains polyfunctionality photocuring aqueous polyurethane acrylate.The present invention is screened by many experiments to be obtained optimal raw material and constitutes and match, and preferably goes out by many experiments optimal synthesis technique.The aqueous polyurethane acrylate prepared has the advantages that sudden strain of a muscle is dry, solid content is high, photo-curing rate is fast, gloss of film degree is high, water-tolerant and hardness are high.
Description
Technical field
The present invention relates to a kind of coating, and in particular to a kind of preparation method of aqueous polyurethane acrylate, belongs to high score
Sub- field of material technology.
Background technology
Photocuring (UV) technology is a kind of brand-new green coating technology (the 5E features researched and developed in the world since the seventies
Industrial technology, i.e. Efficient efficiently, Enabling wide adaptabilities, Economical economy, EnergySaving energy-conservation and
EnvironmentalFriendly is environment-friendly), and the resin for being used for UV technologies also has the title of environmental friendly material.Aqueous UV
Resin is the key component in aqueous UV products, is the binder resin in formula, determines the basic performance of product after this solidification.It is right
It is aqueous than traditional oiliness UV resins (viscosity is adjusted by diluent of the polyfunctional group reactive diluent with certain toxicity)
The water that UV resins only need addition appropriate can complete to adjust viscous work and workmen is not injured completely, with environmental protection
Cry gradually increases, aqueous product will progressively occuping market leading position.
Aqueous UV resins can be substantially divided into by the species of matrix resin：Urethane acrylate, unsaturated polyester (UP) propylene
The major class of acid esters, epoxy acrylate and acrylated acrylics etc. four, wherein urethane acrylate (PUA) system
Basic performance plasticity is very strong, can realize different performance requirements by adjusting raw material type and material rate, therefore,
PUA is a current most widely used class.Self-emulsifying type occupies a most important seat in PUA, traces it to its cause and essentially consists in certainly
Without adding outer emulsifying agent in emulsifying system, the water resistance of system can pass through the species, content, nertralizer of added ion
The factor such as species and degree of ionization is controlled, and finally gives the preferable product of combination property.
It is not provided simultaneously with a variety of outstanding properties such as higher solids content, water resistance and superior mechanical performance also in the prior art
Resin.
The content of the invention
Goal of the invention：The purpose of the present invention is that in view of the shortcomings of the prior art, by many experiments, there is provided a kind of feature of environmental protection
It is good, it is provided simultaneously with the aqueous polyurethane acrylate of a variety of outstanding properties such as higher solids content, water resistance and superior mechanical performance
Preparation method.
Technical scheme, to realize object above, the technical solution adopted by the present invention is：
A kind of preparation method of aqueous polyurethane acrylate, it comprises the following steps：
(1) under nitrogen protection and mechanical agitation, diisocyanate is placed in equipped with constant pressure funnel and thermometer
In four-hole boiling flask, the carboxylic acid containing two hydroxyls is added portionwise in 40~70 DEG C of temperature ranges, be warming up to 60~80 DEG C reaction 1~
3h, obtains holding the polyurethane prepolymer of isocyano；
(2) 40~60 DEG C are cooled to, the three-functionality-degree polyol prepolymer that molecular weight is 1000g/mol is added dropwise, during dropwise addition
Between 0.5~1.5h, be then to slowly warm up to 60~80 DEG C, continue to be incubated 1~3h, obtain holding isocyano polyurethane prepolymer；
(3) and then it is cooled to 40~60 DEG C, adds polymerization inhibitor, pentaerythritol triacrylate, time for adding 1 is then added dropwise
~2h, is to slowly warm up to 70~90 DEG C, continues to be incubated 1~3h, obtains the polyurethane acrylate prepolymer of acrylate ended；
(4) less than 50 DEG C are cooled to, the aqueous solution of tertiary amine is slowly added into reaction system, 1~2h is stirred, obtains many
Degree of functionality photocuring aqueous polyurethane acrylate.The degree of ionization for controlling carboxyl is 40~80%, and solid content is up to 45%
Left and right.
Preferably, in the preparation method of above-described aqueous polyurethane acrylate, step (1), two isocyanides
Acid esters is IPDI, toluene di-isocyanate(TDI), hexamethylene diisocyanate, the isocyanide of dicyclohexyl methyl hydride two
One of acid esters, methyl diphenylene diisocyanate or their any combination.
Preferably, in the preparation method of above-described aqueous polyurethane acrylate, step (1), containing two
The carboxylic acid of hydroxyl is one of dihydromethyl propionic acid, tartaric acid or their any combination.
Preferably, in the preparation method of above-described aqueous polyurethane acrylate, step (2), trifunctional
The polyol prepolymer of degree is one of polycaprolactone polyol, PEPA, PPG or their any combination.
Preferably, the preparation method of above-described aqueous polyurethane acrylate, and step (in (3), polymerization inhibitor
For one of MEHQ, hydroquinones, phenol piperazine or their any combination.
Preferably, the preparation method of above-described aqueous polyurethane acrylate, (in (4), tertiary amine is step
One of triethanolamine, triethylamine or their any combination.
Preferably, the preparation method of above-described aqueous polyurethane acrylate, the quality of diisocyanate
The quality for the polyol prepolymer that number is 15~50 parts, the mass fraction of carboxylic acid containing two hydroxyls is 5~15, three-functionality-degree
Number is that the mass fraction of 25~60, polymerization inhibitor is that the mass fraction of 1~5, pentaerythritol triacrylate is 15~35, tertiary amine
Mass fraction be 1~10.
By entering to raw material composition in above preferred scheme and consumption, the reaction temperature of each step synthesis technique and reaction time
A series of screening experiments of row, as a result prove to reach when raw material concrete composition and consumption, synthesis technique reaction temperature and reaction time
Level product performance reaches most preferably described in embodiment 2.
Beneficial effect：Compared to the prior art, the present invention has the following advantages：
The present invention obtains optimal raw material by many experiments screening and constitutes and match, and is preferably gone out most by many experiments
Good synthesis technique.Whole preparation technology is reasonable in design, and the aqueous polyurethane acrylate prepared is provided simultaneously with compared with Gao Gu
A variety of outstanding properties such as content (up to 45%), water resistance and superior mechanical performance.And with dodge dry, photo-curing rate it is fast,
The advantages of gloss of film degree is high.
Minimum 3 terminal double bonds can be freely designed in the present invention by different material ratio and most 9 ends are double
The resin product of key, effectively double bond is more contained by single molecular resin, it is possible to achieve quick-drying and hardness of paint film is high, glossiness is good.
Be conducive to the solid content of raising system in spherical molecular structure, solid content highest is realized to 45% or so.When in main body
When core uses polyesters or polycaprolactone as skeleton, because ester bond hydrophobicity is good, it is possible to achieve dodge the spies such as dry and water-tolerant
Levy.Many performances can be utilized effectively in high-grade woodcare paint finish paint above, there is good market prospects.
Embodiment
A kind of preparation method of the aqueous polyurethane acrylate of embodiment 1, it comprises the following steps：
(1) under nitrogen protection and mechanical agitation, the IPDI of 30 mass parts is placed directly within and is equipped with
In the four-hole boiling flask of constant pressure funnel and thermometer, the dihydroxy first of 10 mass parts is added portionwise in 40~50 DEG C of temperature ranges
Base propionic acid, is warming up to 70~75 DEG C of reaction 1.5h, obtains holding the polyurethane prepolymer of isocyano；
(2) 40~45 DEG C are cooled to, the three-functionality-degree polycaprolactone polyol prepolymer that molecular weight is 1000g/mol is added dropwise
30 mass parts, time for adding 0.5h is to slowly warm up to 75~80 DEG C, continues to be incubated 3h, obtains holding isocyano polyurethane prepolymer
Thing；
(3) 40~45 DEG C are cooled to, is added after polymerization inhibitor, the pentaerythritol triacrylate that mass parts are 27, drop is added dropwise
1h between added-time, is to slowly warm up to 80~85 DEG C, continues to be incubated 2h, and the polyurethane acrylate prepolymer for obtaining acrylate ended gathers
Body；
(4) less than 50 DEG C are cooled to, by the slow reaction system in addition of the triethylamine aqueous solution of 3 mass parts, 1h is stirred, obtains
To polyfunctionality photocuring aqueous polyurethane acrylate, solid content 46.5% is controlled.
A kind of preparation method of the aqueous polyurethane acrylate of embodiment 2, it comprises the following steps：
(1) under nitrogen protection and mechanical agitation, the dicyclohexyl methyl hydride diisocyanate of 25 mass parts is placed directly within
In four-hole boiling flask equipped with constant pressure funnel and thermometer, 7.5 mass parts are added portionwise in 50~65 DEG C of temperature ranges
Tartaric acid, is warming up to 70~75 DEG C of reaction 2h, obtains holding the polyurethane prepolymer of isocyano；
(2) 40~45 DEG C are cooled to, the matter of three-functionality-degree polyester polyol prepolymers 50 that molecular weight is 1000g/mol is added dropwise
Part is measured, time for adding 1.5h is to slowly warm up to 75~80 DEG C, continues to be incubated 2h, obtains holding isocyano polyurethane prepolymer；
(3) 50~55 DEG C are cooled to, is added after polymerization inhibitor, the pentaerythritol triacrylate of 15 mass parts is added dropwise, is added dropwise
Time 1h, is to slowly warm up to 80~85 DEG C, continues to be incubated 3h, obtains the polyurethane acrylate prepolymer of acrylate ended；
(4) less than 50 DEG C are cooled to, by the slow reaction system in addition of the triethanolamine aqueous solution of 2.5 mass parts, is stirred
2h, obtains polyfunctionality photocuring aqueous polyurethane acrylate, controls solid content 45.7% or so.
A kind of preparation method of the aqueous polyurethane acrylate of embodiment 3, it comprises the following steps：
(1) under nitrogen protection and mechanical agitation, the hexa-methylene methane diisocyanate of 36 mass parts is placed directly within
In four-hole boiling flask equipped with constant pressure funnel and thermometer, the wine of 10 mass parts is added portionwise in 50~65 DEG C of temperature ranges
Stone acid, is warming up to 75~80 DEG C of reaction 3h, obtains holding the polyurethane prepolymer of isocyano；
(2) 40~45 DEG C are cooled to, the matter of three-functionality-degree polyether polyol prepolymer 25 that molecular weight is 1000g/mol is added dropwise
Part is measured, time for adding 1h is to slowly warm up to 75~80 DEG C, continues to be incubated 2h, obtains holding isocyano polyurethane prepolymer；
(3) 50~55 DEG C are cooled to, is added after polymerization inhibitor, the pentaerythritol triacrylate of 23 mass parts is added dropwise, is added dropwise
Time 1h, is to slowly warm up to 85~90 DEG C, continues to be incubated 2.5h, and the polyurethane acrylate prepolymer for obtaining acrylate ended gathers
Body；
(4) less than 50 DEG C are cooled to, by the triethylamine aqueous solution of 6 mass parts in addition reaction system, 1.5h is stirred, obtains
Polyfunctionality photocuring aqueous polyurethane acrylate, controls solid content 45.9% or so.
The performance test of embodiment 4
1st, the watersoluble polyurethane acrylic acid coating prepared to above example 1 to embodiment 3 carries out performance test, surveys
Test result is as shown in table 1 below：
The performance test results of table 1
Note：Curing rate is with 80mW/cm directly in UV curing in table2Light intensity solidification test obtain.
More than test result indicates that, the watersoluble polyurethane acrylic acid coating for preparing of the present invention has good environmental protection
Property, and with excellent adhesive force, excellent hardness and impact resistance, and with good water resistance, and can keep
More than 45% solid content, achieves extraordinary technological progress.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (7)
1. a kind of preparation method of aqueous polyurethane acrylate, it is characterised in that it comprises the following steps：
(1) under nitrogen protection and mechanical agitation, diisocyanate is placed in four mouthfuls equipped with constant pressure funnel and thermometer
In flask, the carboxylic acid containing two hydroxyls is added portionwise in 40~70 DEG C of temperature ranges, 60~80 DEG C of 1~3h of reaction are warming up to,
Obtain holding the polyurethane prepolymer of isocyano；
(2) 40~60 DEG C are cooled to, the three-functionality-degree polyol prepolymer that molecular weight is 1000g/mol, time for adding 0.5 is added dropwise
~1.5h, is then to slowly warm up to 60~80 DEG C, continues to be incubated 1~3h, obtains holding isocyano polyurethane prepolymer；
(3) and then it is cooled to 40~60 DEG C, adds polymerization inhibitor, is then added dropwise pentaerythritol triacrylate, time for adding 1~
2h, is to slowly warm up to 70~90 DEG C, continues to be incubated 1~3h, obtains the polyurethane acrylate prepolymer of acrylate ended；
(4) less than 50 DEG C are cooled to, the aqueous solution of tertiary amine is slowly added into reaction system, 1~2h is stirred, obtains multifunctional
Spend photocuring aqueous polyurethane acrylate.
2. the preparation method of aqueous polyurethane acrylate according to claim 1, it is characterised in that in step (1), two
Isocyanates is IPDI, toluene di-isocyanate(TDI), hexamethylene diisocyanate, dicyclohexyl methyl hydride two
One of isocyanates, methyl diphenylene diisocyanate or their any combination.
3. the preparation method of aqueous polyurethane acrylate according to claim 1, it is characterised in that in step (1), contain
The carboxylic acid of two hydroxyls is one of dihydromethyl propionic acid, tartaric acid or their any combination.
4. the preparation method of aqueous polyurethane acrylate according to claim 1, it is characterised in that in step (2), three
The polyol prepolymer of degree of functionality is one of polycaprolactone polyol, PEPA, PPG or theirs is any
Combination.
5. the preparation method of aqueous polyurethane acrylate according to claim 1, it is characterised in that in step (3), resistance
Poly- agent is one of MEHQ, hydroquinones, phenol piperazine or their any combination.
6. the preparation method of aqueous polyurethane acrylate according to claim 1, it is characterised in that in step (4), uncle
Amine is one of triethanolamine, triethylamine or their any combination.
7. the preparation method of the aqueous polyurethane acrylate according to any one of claim 1 to 6, it is characterised in that two
The mass fraction of isocyanates is 15~50 parts, the mass fraction of carboxylic acid containing two hydroxyls is the polynary of 5~15, three-functionality-degree
The mass fraction of alcohol prepolymer is that the mass fraction of 25~60, polymerization inhibitor is the mass parts of 1~5, pentaerythritol triacrylate
Number is that the mass fraction of 15~35, tertiary amine is 1~10.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116606563A (en) * | 2023-07-21 | 2023-08-18 | 江西美吉新材料科技有限公司 | Novel environment-friendly thermal plastic-absorbing UV ink and preparation method and application thereof |
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