CN110606929A - Epoxy modified waterborne polyurethane emulsion convenient to store and transport, preparation method and storage method - Google Patents
Epoxy modified waterborne polyurethane emulsion convenient to store and transport, preparation method and storage method Download PDFInfo
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- CN110606929A CN110606929A CN201910879564.XA CN201910879564A CN110606929A CN 110606929 A CN110606929 A CN 110606929A CN 201910879564 A CN201910879564 A CN 201910879564A CN 110606929 A CN110606929 A CN 110606929A
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/30—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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4045—Mixtures of compounds of group C08G18/58 with other macromolecular compounds
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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
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
- C08G18/58—Epoxy resins
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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
- C08G18/65—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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- Chemical & Material Sciences (AREA)
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Abstract
The invention provides an epoxy modified waterborne polyurethane emulsion convenient to store and transport, a preparation method and a storage method, and belongs to the field of waterborne polyurethane synthesis. Solves the problems of short storage time and difficult transportation of the existing waterborne polyurethane emulsion. The method comprises the steps of firstly, removing water from polymer diol at 100-120 ℃ in vacuum, raising the temperature of a system to 130-150 ℃ under the protection of nitrogen, adding diisocyanate, an antioxidant, a catalyst, micromolecule diol, a hydrophilic chain extender and epoxy resin, and melting and stirring for 15-70min to obtain a solid prepolymer; the solid prepolymer can be crushed and granulated, and is convenient to store and transport. When the aqueous polyurethane emulsion is used, the prepolymer is thrown into a dispersion reaction kettle, the reaction temperature is controlled to be 50-90 ℃, and then deionized water and a neutralizing agent are added to obtain the aqueous polyurethane emulsion. The method of the invention does not need to add any inert solvent in the reaction process, has short reaction time, and the obtained waterborne polyurethane has higher molecular weight and excellent mechanical property.
Description
Technical Field
The invention belongs to the technical field of waterborne polyurethane synthesis, and particularly relates to an epoxy modified waterborne polyurethane emulsion convenient to store and transport, a preparation method and a storage method.
Background
Polyurethane is widely applied to the fields of adhesives, coatings, paper making and the like, but oil polyurethane can cause harm to human bodies and pollute the environment due to the use of inert solvents, and aqueous polyurethane emulsion is a polyurethane material which takes water as a dispersion medium, cannot pollute the environment, and has the characteristics of no toxicity, no odor, no combustion, no explosion and safety. However, the storage period of the aqueous polyurethane emulsion is only 6 months, and the short storage period greatly affects the application of the aqueous polyurethane. In addition, the waterborne polyurethane is difficult to transport in winter, especially in northern areas, and the application of the waterborne polyurethane is greatly limited.
The epoxy resin has the advantages of high modulus, chemical corrosion resistance and the like, the structure of the epoxy resin contains active epoxy groups, the reaction is easy to occur, and the introduction of the epoxy resin can greatly improve the mechanics, the tolerance and the like of polyurethane.
Disclosure of Invention
The invention aims to solve the problems of short storage time and inconvenient transportation of the existing waterborne polyurethane emulsion during application, and provides an epoxy modified waterborne polyurethane emulsion which is convenient to store and transport, a preparation method and a storage method thereof.
The invention firstly provides an epoxy modified waterborne polyurethane emulsion convenient for storage and transportation, which comprises the following components:
the method comprises the following steps: raising the temperature of the reaction kettle to 100-120 ℃, adding polymer dihydric alcohol, stirring under reduced pressure, dehydrating for 30-120 min, and removing water vapor in the dihydric alcohol;
step two: under the protection of nitrogen, raising the temperature of the reaction system in the step one to 130-150 ℃, adding diisocyanate, an antioxidant, a catalyst, micromolecular dihydric alcohol, a hydrophilic chain extender and epoxy resin, and melting and stirring for 15-70min to obtain a solid prepolymer;
step three: and (3) adding the solid prepolymer obtained in the step two into a dispersion reaction kettle, controlling the reaction temperature at 50-90 ℃, and then adding deionized water and a neutralizing agent to react for 50-60min to obtain the waterborne polyurethane emulsion.
Preferably, the polymer diol of the first step is one or two selected from polyether diol or polyester diol.
Preferably, the polyether diol is selected from one or more of polytetrahydrofuran diol, polypropylene oxide diol or polyethylene oxide diol, and the molecular weight of the polyether diol is 1000-5000 Da.
Preferably, the polyester diol is selected from one or more of poly neopentyl glycol adipate diol, poly hexanediol adipate diol, poly 1, 4-butanediol adipate diol, poly ethylene glycol adipate diol, poly propylene glycol adipate diol or poly caprolactone diol, and the molecular weight range of the polyester diol is 1000-5000 Da.
Preferably, the diisocyanate is selected from one or more of 4, 4-diphenylmethane diisocyanate, toluene diisocyanate, benzylidene diisocyanate, 1, 5-naphthalene diisocyanate, p-phenylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and hydrogenated 4, 4-diphenylmethane diisocyanate.
Preferably, the hydrophilic chain extender is one of dimethylolpropionic acid or dimethylolbutyric acid.
Preferably, the epoxy resin is bisphenol A type epoxy resin and is selected from one of E-51, E-44, E-35 and E-20.
Preferably, the weight ratio of the diisocyanate, the polymer diol, the epoxy resin, the antioxidant, the catalyst, the small molecule diol and the hydrophilic chain extender is (15-50): (140-220): (5-15): (0.1-0.4): (0.01-0.05): (1.2-2.5): (1.5-3.5).
The invention also provides the aqueous polyurethane emulsion obtained by the preparation method.
The invention also provides a storage method of the waterborne polyurethane emulsion, which comprises the following steps:
and (3) crushing and granulating the solid prepolymer in the step two, storing, and adding deionized water and a neutralizing agent for reaction when in use to obtain the waterborne polyurethane emulsion.
The invention has the advantages of
1) The invention provides a preparation method of epoxy modified waterborne polyurethane emulsion convenient for storage and transportation, the preparation process comprises the steps of firstly preparing solid polyurethane prepolymer, wherein the prepolymer is convenient for storage and transportation, and then adding a neutralizer into the prepolymer to prepare the polyurethane emulsion when in use, thereby solving the technical bottleneck that the waterborne polyurethane emulsion is difficult to store and transport.
2) The invention introduces the epoxy resin by utilizing the oxazole structure formed by the epoxy group of the epoxy resin and the-NCO at high temperature, the modified polyurethane obtained by the method can further improve the resistance, the high adhesion and the high strength resistance, and the obtained modified resin integrates the advantages of the epoxy group and the high strength resistance, thereby having great application potential in the fields of adhesives, coatings and the like.
3) The preparation process does not need to add any inert solvent in the reaction process, the reaction time is short, and the obtained waterborne polyurethane has higher molecular weight and excellent mechanical property.
Detailed Description
The invention firstly provides an epoxy modified waterborne polyurethane emulsion convenient for storage and transportation, which comprises the following components:
the method comprises the following steps: raising the temperature of the reaction kettle to 100-120 ℃, adding polymer dihydric alcohol, stirring under reduced pressure, dehydrating for 30-120 min, and removing water vapor in the dihydric alcohol;
step two: under the protection of nitrogen, raising the temperature of the reaction system in the step one to 130-150 ℃, preferably 140 ℃, adding diisocyanate, an antioxidant, a catalyst, micromolecule dihydric alcohol, a hydrophilic chain extender and epoxy resin, and melting and stirring for 15-70min, preferably 50-60min to obtain a solid prepolymer;
step three: and (3) adding the solid prepolymer obtained in the step two into a dispersion reaction kettle, controlling the reaction temperature to be 50-90 ℃, preferably 50-60 ℃, and then adding deionized water and a neutralizing agent to react for 50-60min to obtain the waterborne polyurethane emulsion.
According to the invention, the polymer diol of the first step is selected from one or two of polyether diol or polyester diol, the polyether diol is preferably selected from one or more of polytetrahydrofuran diol, polypropylene oxide diol or polyethylene oxide diol, and the molecular weight of the polyether diol is 1000-5000 Da; the polyester diol is selected from one or more of poly neopentyl glycol adipate diol, poly hexanediol adipate diol, poly 1, 4-butanediol adipate diol, poly ethylene glycol adipate diol, poly propylene glycol adipate diol or poly caprolactone diol, and the molecular weight range of the polyester diol is 1000-5000 Da.
According to the present invention, the diisocyanate is preferably selected from one or more of 4, 4-diphenylmethane diisocyanate, toluene diisocyanate, xylylene diisocyanate, 1, 5-naphthalene diisocyanate, p-phenylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and hydrogenated 4, 4-diphenylmethane diisocyanate.
According to the invention, the antioxidant is preferably selected from one of the antioxidants 1076, 1010, 264 from basf.
According to the invention, the catalyst is preferably one of dibutyltin dilaurate or stannous octoate.
According to the invention, the hydrophilic chain extender is preferably one of dimethylolpropionic acid or dimethylolbutyric acid.
According to the invention, the small molecule diol is preferably butanediol.
According to the invention, the epoxy resin is preferably bisphenol A epoxy resin and is selected from one of E-51, E-44, E-35 and E-20.
According to the invention, the neutralizing agent is preferably one of ammonia, diethanolamine, triethanolamine and triethylamine.
According to the invention, the weight ratio of the diisocyanate, the polymer diol, the epoxy resin, the antioxidant, the catalyst, the small molecule diol, the hydrophilic chain extender and the neutralizing agent is preferably (15-50): (140-220): (5-15): (0.1-0.4): (0.01-0.05): (1.2-2.5): (1.5-3.5): (4-8), more preferably (20-40): (150-200): (7.8-13.6): (0.15-0.2): 0.02: (1.3-1.8): (2.7-2.9): (5-6.5).
The invention also provides the aqueous polyurethane emulsion obtained by the preparation method.
The invention also provides a storage method of the waterborne polyurethane emulsion, which comprises the following steps:
and (3) crushing and granulating the solid prepolymer in the step two, storing, and adding deionized water and a neutralizing agent for reaction when in use to obtain the waterborne polyurethane emulsion.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are only for illustrating the present invention and are not intended to limit the scope of the present invention.
Example 1
The first step is as follows: raising the temperature of the reaction kettle to 120 ℃, adding 190g of poly adipic acid-1, 4-butanediol ester diol (Mn ═ 2000), stirring under reduced pressure, and dehydrating for 60 min;
the second step is that: raising the temperature of the reaction kettle to 140 ℃ under the protection of nitrogen, adding 35g of isophorone diisocyanate, 9g of epoxy resin E-44, 0.2g of antioxidant 1010, 0.02g of dibutyltin dilaurate, 1.8g of butanediol and 2.7g of dimethylolpropionic acid, melting, and stirring for 60min to obtain a prepolymer;
the third step: taking the prepolymer out of the kettle at 140 ℃ and forming a solid at room temperature;
the fourth step: and adding the prepolymer into a second dispersion reaction kettle, controlling the reaction temperature at 50 ℃, adding 300g of deionized water and 6g of triethylamine, and reacting for 60min to obtain the product.
The waterborne polyurethane obtained in example 1 is marked as PU-1, and the performance test results are shown in Table 1.
Example 2
The first step is as follows: raising the temperature of the reaction kettle to 120 ℃, adding 200g of poly neopentyl glycol adipate diol (Mn is 2000), stirring under reduced pressure, and dehydrating for 60 min;
the second step is that: under the protection of nitrogen, raising the temperature of the reaction kettle to 130 ℃, adding 40g of 4, 4-diphenylmethane diisocyanate, 13.6g of epoxy resin E-44, 0.2g of antioxidant 1076, 0.02g of dibutyltin dilaurate, 1.8g of butanediol and 2.9g of dimethylolpropionic acid, melting, and stirring for 60min to obtain a prepolymer;
the third step: taking the prepolymer out of the kettle at 130 ℃ and forming a solid at room temperature;
the fourth step: and adding the prepolymer into a second dispersion reaction kettle, controlling the reaction temperature at 50 ℃, adding 310g of deionized water and 6.5g of triethanolamine, and reacting for 60min to obtain a product.
The waterborne polyurethane obtained in example 2 is labeled as PU-2, and the performance test results are shown in Table 1.
Example 3
The first step is as follows: raising the temperature of the reaction kettle to 120 ℃, adding 200g of polyoxyethylene glycol (Mn is 3000), stirring under reduced pressure, and dehydrating for 60 min;
the second step is that: under the protection of nitrogen, raising the temperature of the reaction kettle to 140 ℃, adding 20g of toluene diisocyanate, 7.8g of epoxy resin E-51, 0.2g of antioxidant 264, 0.02g of dibutyltin dilaurate, 1.5g of butanediol and 2.9g of dimethylolpropionic acid, melting, and stirring for 50min to obtain a prepolymer;
the third step: taking the prepolymer out of the kettle at 140 ℃ and forming a solid at room temperature;
the fourth step: and adding the prepolymer into a second dispersion reaction kettle, controlling the reaction temperature at 60 ℃, adding 310g of deionized water and 6g of triethanolamine, and reacting for 50min to obtain a product.
The waterborne polyurethane obtained in example 3 is labeled as PU-3, and the performance test results are shown in Table 1.
Example 4
The first step is as follows: raising the temperature of the reaction kettle to 120 ℃, adding 150g of polytetrahydrofuran diol (Mn ═ 2000), stirring under reduced pressure, and dehydrating for 60 min;
the second step is that: under the protection of nitrogen, raising the temperature of the reaction kettle to 140 ℃, adding 20g of hexamethylene diisocyanate, 11.4g of epoxy resin E-35, 0.15g of antioxidant 1010, 0.02g of dibutyltin dilaurate, 1.3g of butanediol and 2.9g of dimethylolpropionic acid, melting, and stirring for 50min to obtain a prepolymer;
the third step: taking the prepolymer out of the kettle at 140 ℃ and forming a solid at room temperature;
the fourth step: and adding the prepolymer into a second dispersion reaction kettle, controlling the reaction temperature at 60 ℃, adding 270g of deionized water and 5g of triethanolamine, and reacting for 60min to obtain a product.
The waterborne polyurethane obtained in example 4 is labeled as PU-4, and the performance test results are shown in Table 1.
TABLE 1 Performance test results of dried coating films of aqueous polyurethane dispersions
Claims (10)
1. An epoxy modified waterborne polyurethane emulsion convenient for storage and transportation is characterized by comprising:
the method comprises the following steps: raising the temperature of the reaction kettle to 100-120 ℃, adding polymer dihydric alcohol, stirring under reduced pressure, dehydrating for 30-120 min, and removing water vapor in the dihydric alcohol;
step two: under the protection of nitrogen, raising the temperature of the reaction system in the step one to 130-150 ℃, adding diisocyanate, an antioxidant, a catalyst, micromolecular dihydric alcohol, a hydrophilic chain extender and epoxy resin, and melting and stirring for 15-70min to obtain a solid prepolymer;
step three: and (3) adding the solid prepolymer obtained in the step two into a dispersion reaction kettle, controlling the reaction temperature at 50-90 ℃, and then adding deionized water and a neutralizing agent to react for 50-60min to obtain the waterborne polyurethane emulsion.
2. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation of claim 1, wherein the polymer diol of the first step is one or two selected from polyether diol and polyester diol.
3. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation as claimed in claim 2, wherein the polyether diol is selected from polytetrahydrofuran diol, polyoxypropylene diol or polyoxyethylene diol, and has a molecular weight of 1000-5000 Da.
4. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation as claimed in claim 2, wherein the polyester diol is selected from one or more of poly neopentyl glycol adipate diol, poly hexanediol adipate diol, poly 1, 4-butylene glycol adipate diol, poly ethylene glycol adipate diol, poly propylene glycol adipate diol or poly caprolactone diol, and has a molecular weight range of 1000-.
5. The epoxy modified waterborne polyurethane emulsion capable of being stored and transported conveniently as claimed in claim 1, wherein the diisocyanate is selected from one or more of 4, 4-diphenylmethane diisocyanate, toluene diisocyanate, benzylidene diisocyanate, 1, 5-naphthalene diisocyanate, p-phenylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and hydrogenated 4, 4-diphenylmethane diisocyanate.
6. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation of claim 1, wherein the hydrophilic chain extender is one of dimethylolpropionic acid or dimethylolbutyric acid.
7. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation of claim 1, wherein the epoxy resin is bisphenol a epoxy resin selected from one of E-51, E-44, E-35 and E-20.
8. The epoxy modified waterborne polyurethane emulsion convenient for storage and transportation of claim 1, wherein the weight ratio of the diisocyanate, the polymer diol, the epoxy resin, the antioxidant, the catalyst, the small molecule diol and the hydrophilic chain extender is (15-50): (140-220): (5-15): (0.1-0.4): (0.01-0.05): (1.2-2.5): (1.5-3.5).
9. An aqueous polyurethane emulsion obtained by the production method according to any one of claims 1 to 8.
10. A method for storing the aqueous polyurethane emulsion according to claim 9, comprising:
and (3) crushing and granulating the solid prepolymer in the step two, storing, and adding deionized water and a neutralizing agent for reaction when in use to obtain the waterborne polyurethane emulsion.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116903813A (en) * | 2023-09-12 | 2023-10-20 | 吉林中科优锐科技有限公司 | Preparation method of storage-stable PPDI polyurethane prepolymer |
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