CN105418871A - Preparation method of fluorine-containing soybean-oil-based waterborne polyurethane - Google Patents
Preparation method of fluorine-containing soybean-oil-based waterborne polyurethane Download PDFInfo
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- CN105418871A CN105418871A CN201510770438.2A CN201510770438A CN105418871A CN 105418871 A CN105418871 A CN 105418871A CN 201510770438 A CN201510770438 A CN 201510770438A CN 105418871 A CN105418871 A CN 105418871A
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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
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
- C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3817—Hydroxylated esters of higher fatty acids
Abstract
The invention belongs to the technical field of preparation of waterborne polyurethane, and discloses a preparation method of fluorine-containing soybean-oil-based waterborne polyurethane. The preparation method specifically includes the steps that epoxidized soybean oil is subjected to a ring-opening reaction through trifluoroacetic acid to obtain fluorine-containing soybean-oil-based polyhydric alcohol, then fluorine-containing soybean-oil-based polyhydric alcohol is reacted with diisocyanate and hydrophilic monomers to generate fluorine-containing soybean-oil-based polyurethane prepolymers, triethylamine is added to be neutralized with carboxyl, deionized water is added for emulsification, then ethylenediamine is added for chain extension, and fluorine-containing soybean-oil-based waterborne polyurethane is obtained. According to the preparation method, an existing technology is improved, namely, soybean oil polyhydric alcohol which is a renewable resource is used for replacing a petroleum product, and the preparation method of fluorine-containing soybean-oil-based waterborne polyurethane is environmentally friendly.
Description
Technical field
The invention belongs to the preparing technical field of aqueous polyurethane, be specifically related to a kind of preparation method of fluorine-containing soybean oil based aqueous polyurethane.
Background technology
Urethane is the family macromolecule containing carbamate feature unit in main chain.This macromolecular material is widely used in tamanori, coating, low speed tire, packing ring, the industrial circles such as car pad.Be used to manufacture various foam and plastic sponge at daily life field urethane.Different according to dispersion agent, urethane is divided into oiliness urethane and aqueous polyurethane.Oiliness urethane contaminate environment, toxicity is large, cost is high.Aqueous polyurethane is dispersion agent with water, greatly reduces organic solvent, reduces cost and murder by poisoning.Urethane is obtained by vulcabond and polyol reaction usually, and polyvalent alcohol derives from oil mostly.In the face of the growing tension of oil supply, find replaceable polyvalent alcohol resource and seem particularly important.
The nucleus of fluorine atom is strong to the constraint effect of out-shell electron, and polarizable rate is low, therefore the specific inductivity of fluorocarbon and polarization factor all less.Corresponding this kind of structure, fluorocarbon has high-temperature stability and unreactiveness.Fluorine-containing polyurethane resin coating is a kind of coating of tool excellent properties of ambient temperature curable, there is the character such as low-refraction, low-k, and the low surface energy of fluoropolymer and low-friction coefficient make it again to have outstanding hydrophobic and oil repellent and anti-adhesion properties.
Summary of the invention
The object of this invention is to provide a kind of preparation method of fluorine-containing soybean oil based aqueous polyurethane.
For achieving the above object, the present invention by the following technical solutions:
A preparation method for fluorine-containing soybean oil based aqueous polyurethane, comprises the following steps:
(1) in reaction flask, add trifluoroacetic acid and sodium carbonate, stirring at room temperature, after being diluted by epoxy soybean oil normal hexane, be added drop-wise to reaction flask, continue to stir;
(2) be warming up to 60 ~ 70 DEG C, stir 1 ~ 2h;
(3) normal hexane and unreacted trifluoroacetic acid are reclaimed in air distillation, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) in reaction flask, add fluorine-containing soybean oil base polyol, dimethylol propionic acid, N-Methyl pyrrolidone, stirring at room temperature, add vulcabond, after room temperature reaction 20 ~ 30min, be warming up to 70 ~ 90 DEG C, insulation 2 ~ 3h, be cooled to 40 ~ 50 DEG C, add acetone diluted, be cooled to room temperature, add triethylamine, add deionized water emulsification again, add quadrol afterwards and stir 4 ~ 6h, reduced pressure at room temperature takes off acetone, obtains fluorine-containing soybean oil based aqueous polyurethane.
Further, the described epoxy soybean oil average per molecule of step (1) contains 2.1 ~ 2.5 epoxy group(ing).
Further, in step (1), the mol ratio of trifluoroacetic acid and sodium carbonate is 100:0.5 ~ 1, and the mol ratio of epoxy soybean oil and trifluoroacetic acid is 1:2.2 ~ 3.
Further, in step (1), mass ratio 1:1 ~ 2 of epoxy soybean oil and normal hexane.
Further, in step (1), be added drop-wise to reaction flask after being diluted by epoxy soybean oil normal hexane, dropwise in 1 ~ 2h, continue stirring at room temperature 1 ~ 2h.
Further, in step (3), at 80 ~ 90 DEG C: normal hexane and unreacted trifluoroacetic acid are reclaimed in air distillation, residual normal hexane and trifluoroacetic acid are sloughed in decompression.
Further, in step (4), the mol ratio of vulcabond, fluorine-containing soybean oil base polyol, dimethylol propionic acid, quadrol is 100:50 ~ 55:25 ~ 30:15 ~ 25.
Further, in step (4), the mass ratio of acetone and system non-volatile matter is 0.5 ~ 0.8:1, and the mass ratio of deionized water and system non-volatile matter is 2.5 ~ 3.5:1.
Further, in step (4), the mol ratio of triethylamine and dimethylol propionic acid is 9 ~ 10:10.
Further, in step (4), the mass ratio of N-Methyl pyrrolidone and dimethylol propionic acid is 1:1.
Further, step (4) described vulcabond is at least one in tolylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, diphenylmethanediisocyanate, dicyclohexyl methane diisocyanate and lysinediisocyanate.
The present invention has following beneficial effect:
1 the present invention uses trifluoroacetic acid to carry out ring-opening reaction to epoxy soybean oil and obtains fluorine-containing soybean oil base polyol; soybean oil is a kind of renewable resources; can petroleum replacing product, and normal hexane can recycle and reuse, and therefore the present invention is the preparation method being conducive to conservation of resources.
2 the present invention use normal hexane to dilute epoxy soybean oil, and are slowly added drop-wise to by the epoxy soybean oil that normal hexane dilutes in the trifluoroacetic acid constantly stirred, and avoid trifluoroacetic acid catalysis epoxy soybean oil to be polymerized.
3 the present invention utilize fluorine-containing soybean oil base polyol and vulcabond, hydrophilic monomer to react and generate fluorine-containing soybean oil based base polyurethane prepolymer for use as, add triethylamine and carboxyl neutralizes, add deionized water emulsification, add quadrol chain extension again, obtained fluorine-containing soybean oil based aqueous polyurethane, provides a kind of preparation method of novel fluorine-containing soybean oil based aqueous polyurethane.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further:
embodiment 1
According to the fluorine-containing soybean oil based aqueous polyurethane of following steps:
(1) in the there-necked flask that mechanical stirring, reflux condensing tube and constant pressure funnel are housed, 342g(3mol is added) trifluoroacetic acid and 3.18g(0.03mol) sodium carbonate, by 900g(1mol) average per molecule contain 2.2 epoxy group(ing) epoxy soybean oil 900g normal hexane dilution after join in constant pressure funnel, slowly reaction flask is added drop-wise under violent mechanical stirring, dropwise in 2h, continue stirring at room temperature 2h;
(2) be warming up to 70 DEG C, stir 1h;
Normal hexane and unreacted trifluoroacetic acid are reclaimed in (3) 80 DEG C of air distillations, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) mechanical stirring is being housed, reflux condensing tube, 575g(0.5mol is added in the four-hole boiling flask of thermometer) fluorine-containing soybean oil base polyol, 33.5g(0.25mol) dimethylol propionic acid, 33.5gN-methylpyrrolidone, stirring at room temperature, slowly add 174g(1mol) tolylene diisocyanate, after room temperature reaction 20min, slowly be warming up to 80 DEG C, insulation 2h, be cooled to 50 DEG C, add 350g acetone diluted viscosity reduction, be cooled to room temperature, add 25g(0.25mol) triethylamine, stir 10min, add the emulsification of 2000mL deionized water rapid stirring again, stir 10min, add 12g(0.2mol afterwards) quadrol, continue to stir 4h, reduced pressure at room temperature takes off acetone, obtain fluorine-containing soybean oil based aqueous polyurethane.
embodiment 2
According to the fluorine-containing soybean oil based aqueous polyurethane of following steps:
(1) in the there-necked flask that mechanical stirring, reflux condensing tube and constant pressure funnel are housed, 342g(3mol is added) trifluoroacetic acid and 1.59g(0.015mol) sodium carbonate, by 900g(1mol) average per molecule contain 2.5 epoxy group(ing) epoxy soybean oil 1800g normal hexane dilution after join in constant pressure funnel, slowly reaction flask is added drop-wise under violent mechanical stirring, dropwise in 1h, continue stirring at room temperature 1h;
(2) be warming up to 60 DEG C, stir 2h;
Normal hexane and unreacted trifluoroacetic acid are reclaimed in (3) 90 DEG C of air distillations, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) mechanical stirring is being housed, reflux condensing tube, 593g(0.5mol is added in the four-hole boiling flask of thermometer) fluorine-containing soybean oil base polyol, 33.5g(0.25mol) dimethylol propionic acid, 33.5gN-methylpyrrolidone, stirring at room temperature, slowly add 222g(1mol) isophorone diisocyanate, after room temperature reaction 20min, slowly be warming up to 90 DEG C, insulation 3h, be cooled to 40 DEG C, add 350g acetone diluted viscosity reduction, be cooled to room temperature, add 25g(0.25mol) triethylamine, stir 10min, add the emulsification of 2000mL deionized water rapid stirring again, stir 10min, add 15g(0.25mol afterwards) quadrol, continue to stir 6h, reduced pressure at room temperature takes off acetone, obtain fluorine-containing soybean oil based aqueous polyurethane.
embodiment 3
According to the fluorine-containing soybean oil based aqueous polyurethane of following steps:
(1) in the there-necked flask that mechanical stirring, reflux condensing tube and constant pressure funnel are housed, 251g(2.2mol is added) trifluoroacetic acid and 1.87g(0.0176mol) sodium carbonate, by 900g(1mol) average per molecule contain 2.1 epoxy group(ing) epoxy soybean oil 1200g normal hexane dilution after join in constant pressure funnel, slowly reaction flask is added drop-wise under violent mechanical stirring, dropwise in 1.5h, continue stirring at room temperature 1.5h;
(2) be warming up to 65 DEG C, stir 1.5h;
Normal hexane and unreacted trifluoroacetic acid are reclaimed in (3) 85 DEG C of air distillations, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) mechanical stirring is being housed, reflux condensing tube, 627g(0.55mol is added in the four-hole boiling flask of thermometer) fluorine-containing soybean oil base polyol, 40.2g(0.30mol) dimethylol propionic acid, 40.2gN-methylpyrrolidone, stirring at room temperature, slowly add 168g(1mol) hexamethylene diisocyanate, after room temperature reaction 30min, slowly be warming up to 70 DEG C, insulation 3h, be cooled to 50 DEG C, add the acetone diluted viscosity reduction that quality is reaction system non-volatile matter 0.5 times, be cooled to room temperature, add 27.3g(0.27mol) triethylamine, stir 10min, add the deionized water rapid stirring emulsification that quality is reaction system non-volatile matter 3.5 times again, stir 10min, add 9g(0.15mol afterwards) quadrol, continue to stir 6h, reduced pressure at room temperature takes off acetone, obtain fluorine-containing soybean oil based aqueous polyurethane.
embodiment 4
According to the fluorine-containing soybean oil based aqueous polyurethane of following steps:
(1) in the there-necked flask that mechanical stirring, reflux condensing tube and constant pressure funnel are housed, 285g(2.5mol is added) trifluoroacetic acid and 2.65g(0.025mol) sodium carbonate, by 900g(1mol) average per molecule contain 2.5 epoxy group(ing) epoxy soybean oil 1500g normal hexane dilution after join in constant pressure funnel, slowly reaction flask is added drop-wise under violent mechanical stirring, dropwise in 2h, continue stirring at room temperature 1h;
(2) be warming up to 60 DEG C, stir 2h;
Normal hexane and unreacted trifluoroacetic acid are reclaimed in (3) 90 DEG C of air distillations, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) mechanical stirring is being housed, reflux condensing tube, 652g(0.55mol is added in the four-hole boiling flask of thermometer) fluorine-containing soybean oil base polyol, 40.2g(0.30mol) dimethylol propionic acid, 40.2gN-methylpyrrolidone, stirring at room temperature, slowly add 262g(1mol) dicyclohexyl methane diisocyanate, after room temperature reaction 25min, slowly be warming up to 80 DEG C, insulation 2.5h, be cooled to 45 DEG C, add the acetone diluted viscosity reduction that quality is reaction system non-volatile matter 0.8 times, be cooled to room temperature, add 28.8g(0.285mol) triethylamine, stir 10min, add the deionized water rapid stirring emulsification that quality is reaction system non-volatile matter 2.5 times again, stir 10min, add 12g(0.20mol afterwards) quadrol, continue to stir 5h, reduced pressure at room temperature takes off acetone, obtain fluorine-containing soybean oil based aqueous polyurethane.
The above; be only the specific embodiment of the present invention, but protection scope of the present invention is not limited thereto, anyly belongs to those skilled in the art in the technical scope that the present invention discloses; the change that can expect easily or replacement, all should be encompassed within protection scope of the present invention.Therefore, protection scope of the present invention should be as the criterion with the protection domain of claim.
Claims (10)
1. a preparation method for fluorine-containing soybean oil based aqueous polyurethane, is characterized in that, comprise the following steps:
(1) in reaction flask, add trifluoroacetic acid and sodium carbonate, stirring at room temperature, after being diluted by epoxy soybean oil normal hexane, be added drop-wise to reaction flask, continue to stir;
(2) be warming up to 60 ~ 70 DEG C, stir 1 ~ 2h;
(3) normal hexane and unreacted trifluoroacetic acid are reclaimed in air distillation, more residual normal hexane and trifluoroacetic acid are sloughed in decompression, obtain fluorine-containing soybean oil base polyol;
(4) in reaction flask, add fluorine-containing soybean oil base polyol, dimethylol propionic acid, N-Methyl pyrrolidone, stirring at room temperature, add vulcabond, after room temperature reaction 20 ~ 30min, be warming up to 70 ~ 90 DEG C, insulation 2 ~ 3h, be cooled to 40 ~ 50 DEG C, add acetone diluted, be cooled to room temperature, add triethylamine, add deionized water emulsification again, add quadrol afterwards and stir 4 ~ 6h, reduced pressure at room temperature takes off acetone, obtains fluorine-containing soybean oil based aqueous polyurethane.
2. preparation method according to claim 1, is characterized in that, the described epoxy soybean oil average per molecule of step (1) contains 2.1 ~ 2.5 epoxy group(ing).
3. preparation method according to claim 1, is characterized in that, in step (1), the mol ratio of trifluoroacetic acid and sodium carbonate is 100:0.5 ~ 1, and the mol ratio of epoxy soybean oil and trifluoroacetic acid is 1:2.2 ~ 3.
4. the preparation method according to claim 1 or 3, is characterized in that, in step (1), and mass ratio 1:1 ~ 2 of epoxy soybean oil and normal hexane.
5. the preparation method according to claim 1 or 3, is characterized in that, in step (1), is added drop-wise to reaction flask, dropwises in 1 ~ 2h, continue stirring at room temperature 1 ~ 2h after being diluted by epoxy soybean oil normal hexane.
6. preparation method according to claim 1, is characterized in that, in step (3), at 80 ~ 90 DEG C: normal hexane and unreacted trifluoroacetic acid are reclaimed in air distillation, and residual normal hexane and trifluoroacetic acid are sloughed in decompression.
7. preparation method according to claim 1, is characterized in that, in step (4), the mol ratio of vulcabond, fluorine-containing soybean oil base polyol, dimethylol propionic acid, quadrol is 100:50 ~ 55:25 ~ 30:15 ~ 25.
8. the preparation method according to claim 1 or 7, is characterized in that, in step (4), the mass ratio of acetone and system non-volatile matter is 0.5 ~ 0.8:1, and the mass ratio of deionized water and system non-volatile matter is 2.5 ~ 3.5:1.
9. the preparation method according to claim 1 or 7, is characterized in that, in step (4), the mol ratio of triethylamine and dimethylol propionic acid is 9 ~ 10:10, and the mass ratio of N-Methyl pyrrolidone and dimethylol propionic acid is 1:1.
10. the preparation method according to claim 1 or 7, it is characterized in that, step (4) described vulcabond is at least one in tolylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, diphenylmethanediisocyanate, dicyclohexyl methane diisocyanate and lysinediisocyanate.
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| CN105418871B (en) | 2018-07-20 |
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