CN105504206A - Synthetic method of castor oil based enclosed type waterborne polyurethane - Google Patents
Synthetic method of castor oil based enclosed type waterborne polyurethane Download PDFInfo
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- CN105504206A CN105504206A CN201510981190.4A CN201510981190A CN105504206A CN 105504206 A CN105504206 A CN 105504206A CN 201510981190 A CN201510981190 A CN 201510981190A CN 105504206 A CN105504206 A CN 105504206A
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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
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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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
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/286—Oximes
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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
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
-
- 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
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- C09D175/08—Polyurethanes from polyethers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of castor oil based enclosed type waterborne polyurethane. The synthetic method comprises steps as follows: castor oil, polyethylene glycol and a hydrophilic chain extender are adopted to react with diisocyanate in a hydrophilic solvent, and a polyurethane prepolymer with a terminal NCO group is obtained; a sealing agent is adopted to be in an end capping reaction with the prepolymer, and an enclosed type polyurethane prepolymer is obtained; finally, after the enclosed type polyurethane prepolymer is in a neutralization reaction with a neutralizer, a product is dispersed in deionized water, and castor oil based enclosed type waterborne polyurethane is obtained. The adopted castor oil is an important renewable resource, and enclosed type waterborne polyurethane synthesized with the castor oil as a raw material has the characteristic of high self-crosslinking; a polyurethane coating prepared from the product has better heat resistance, volume resistivity, tensile strength and breaking elongation.
Description
Technical field
The invention belongs to chemosynthesis technical field, be specifically related to a kind of synthetic method of castor oil-base Waterborne Blocked Polyurethane.
Background technology
Blocked polyurethane is widely used in the industries such as coating, tackiness agent and surface daub on a wall, but, causes the pollution of environment and the waste of resource during synthesis blocked polyurethane mostly with an organic solvent.At present, along with domestic and international to the extensive attention of environment and safety problem, people's environmental consciousness day by day strengthen and security for all countries, environmental regulation determination and day by day strengthen, the application of conventional solvent type polyurethane is more and more restricted, aqueous polyurethane is low with its VOC content, the feature of excellent performance and replace solvent borne polyurethane and will become trend of the times, as the important component part of urethane, blocked polyurethane also has identical trend.
Vegetables oil and lipid acid thereof are one of more important renewable resource, Viscotrol C (C.O.) is the Witepsol W-S 55 of lipid acid, in lipid acid, 90% is ricinolic acid (9-thiazolinyl-12-hydroxy octadecadienoic acid), with hydroxyl in molecule, can be used for replacing polyester or polyether glycol and isocyanate reaction, preparation has the urethane resin of crosslinking structure.C.O. in component, the nonpolar fatty acid chain of long-chain makes film have good hydrophobic interaction, gives the good flexibility of coating and flexible resistance and winter hardiness simultaneously.Unsaturated carbon-carbon double bond in lipid acid, by oxidation cross-linked, forms high-performance self-crosslinking polymer material.C.O. be the Waterborne Blocked Polyurethane of Material synthesis height self-crosslinking, the physicals of Waterborne Blocked Polyurethane can be improved.
Summary of the invention
The object of this invention is to provide a kind of synthetic method of castor oil-base Waterborne Blocked Polyurethane, scientific and reasonable, simple, obtained product has that VOC content is low, the feature of excellent performance.
The synthetic method of castor oil-base Waterborne Blocked Polyurethane of the present invention be use Viscotrol C, polyoxyethylene glycol, hydrophilic chain extender in hydrophilic solvent with di-isocyanate reaction, obtain the polyurethane prepolymer holding NCO base; Re-use encapsulant and above-mentioned prepolymer carries out end capping, obtain blocked polyurethane prepolymer; Eventually pass after carrying out neutralization reaction with neutralizing agent, disperse in deionized water, obtain castor oil-base Waterborne Blocked Polyurethane.
Described polyoxyethylene glycol (PEG) is one or both in PEG1000 or PEG2000.
Described vulcabond is the one in tolylene diisocyanate (TDI-80), '-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI) or 4,4'-dicyclohexyl methane diisocyanate (HMDI).
Described hydrophilic solvent is N methyl-2-pyrrolidone (NMP), and hydrophilic chain extender is dimethylol propionic acid (DMPA), and encapsulant is methyl ethyl ketoxime (MEKO), and neutralizing agent is triethylamine (TEA).
The synthetic method of castor oil-base Waterborne Blocked Polyurethane of the present invention, step is as follows:
(1) Viscotrol C, polyoxyethylene glycol and hydrophilic chain extender are put into the four-hole boiling flask with stirring and heating unit, after 100 DEG C of vacuum hydro-extraction 1h, add hydrophilic solvent and vulcabond ([NCO]/[OH]=1.5), the moisture content of hydrophilic solvent is within 0.05%, reaction is until its NCO content reaches theoretical value under nitrogen protection, obtain the polyurethane prepolymer holding NCO base, wherein NCO content adopts Di-n-Butyl Amine method to measure (ASTMD2572-97);
(2) in the product of previous step, add encapsulant reaction, obtain blocked polyurethane prepolymer;
(3) add in the product of previous step neutralizing agent carry out in and, under agitation add deionized water and carry out dispersion and obtain castor oil-base Waterborne Blocked Polyurethane.
Temperature of reaction described in step (1) is 75-85 DEG C, and the reaction times is 2-3h.
Temperature of reaction described in step (2) is 75-85 DEG C, and the reaction times is 2-3h.
Neutral temperature described in step (3) is 55-65 DEG C, in and the time be 0.5-1h.
The speed of the stirring described in step (3) is 4000-8000r/min.
The solid content of the castor oil-base Waterborne Blocked Polyurethane that the present invention obtains is 20-40%.
The present invention compared with prior art, has following beneficial effect:
1, solvent of the present invention is water, is the aqueous dispersions of blocked polyurethane, has that VOC content is low, the feature of excellent performance.
2, the Viscotrol C that the present invention adopts is a kind of important renewable resource, and the Waterborne Blocked Polyurethane being Material synthesis with it has the feature of height self-crosslinking.
3, the polyurethane coating film thermotolerance, volume specific resistance, tensile strength and the elongation at break that use product of the present invention to obtain are all better.
Embodiment
Below in conjunction with embodiment, the present invention is described further.
Embodiment 1
The Viscotrol C measured, PEG1000 and DMPA are put into stirring and the four-hole boiling flask of heating unit, after 100 DEG C of vacuum hydro-extraction 1h, add the NMP of metering (through super-dry, moisture content is within 0.05%) and TDI-80 ([NCO]/[OH]=1.5) 80 DEG C of reaction 2h under nitrogen protection, until its NCO content reaches theoretical value, obtain urethane (PU) prepolymer that mass concentration is the end NCO base of 50%; Continue the MEKO reaction adding metering, at 80 DEG C, react 2h, obtain blocked polyurethane prepolymer (BPU); Add triethylamine neutralization reaction 0.5h at 60 DEG C after, under the stirring of rotating speed 4000r/min, add deionized water carry out disperseing to obtain the blocked polyurethane aqueous dispersions (BPUD) that solid content is 30%.
Embodiment 2
The Viscotrol C measured, PEG2000 and DMPA are put into stirring and the four-hole boiling flask of heating unit, after 100 DEG C of vacuum hydro-extraction 1h, add the NMP of metering (through super-dry, moisture content is within 0.05%) and heating and melting pure MDI ([NCO]/[OH]=1.5) under nitrogen protection 75 DEG C reaction 3h, until its NCO content reaches theoretical value, obtain urethane (PU) prepolymer that mass concentration is the end NCO base of 60%; Continue the MEKO reaction adding metering, at 75 DEG C, react 3h, obtain blocked polyurethane prepolymer (BPU); Add triethylamine neutralization reaction 1h at 55 DEG C after, under the stirring of rotating speed 8000r/min, add deionized water carry out disperseing to obtain the blocked polyurethane aqueous dispersions (BPUD) that solid content is 20%.
Embodiment 3
The Viscotrol C measured, PEG1000, PEG2000 and DMPA are put into stirring and the four-hole boiling flask of heating unit, after 100 DEG C of vacuum hydro-extraction 1h, add the NMP of metering (through super-dry, moisture content is within 0.05%) and IPDI ([NCO]/[OH]=1.5) 85 DEG C of reaction 2h under nitrogen protection, until its NCO content reaches theoretical value, obtain urethane (PU) prepolymer that mass concentration is the end NCO base of 70%; Continue the MEKO reaction adding metering, at 85 DEG C, react 2h, obtain blocked polyurethane prepolymer (BPU); Add triethylamine neutralization reaction 0.5h at 65 DEG C after, under the stirring of rotating speed 6000r/min, add deionized water carry out disperseing to obtain the blocked polyurethane aqueous dispersions (BPUD) that solid content is 40%.
Claims (9)
1. a synthetic method for castor oil-base Waterborne Blocked Polyurethane, it is characterized in that using Viscotrol C, polyoxyethylene glycol, hydrophilic chain extender in hydrophilic solvent with di-isocyanate reaction, obtain the polyurethane prepolymer holding NCO base; Re-use encapsulant and above-mentioned prepolymer carries out end capping, obtain blocked polyurethane prepolymer; Eventually pass after carrying out neutralization reaction with neutralizing agent, disperse in deionized water, obtain castor oil-base Waterborne Blocked Polyurethane.
2. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 1, is characterized in that described polyoxyethylene glycol is one or both in PEG1000 or PEG2000.
3. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 1, it is characterized in that described vulcabond is the one in tolylene diisocyanate, '-diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate or 4,4'-dicyclohexyl methane diisocyanate.
4. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 1, it is characterized in that described hydrophilic solvent is N methyl-2-pyrrolidone, hydrophilic chain extender is dimethylol propionic acid, and encapsulant is methyl ethyl ketoxime, and neutralizing agent is triethylamine.
5., according to the synthetic method of the arbitrary described castor oil-base Waterborne Blocked Polyurethane of claim 1-4, it is characterized in that step is as follows:
(1) Viscotrol C, polyoxyethylene glycol and hydrophilic chain extender are put into the four-hole boiling flask with stirring and heating unit, after 100 DEG C of vacuum hydro-extraction 1h, add hydrophilic solvent and vulcabond, the moisture content of hydrophilic solvent is within 0.05%, reaction is until its NCO content reaches theoretical value under nitrogen protection, obtain the polyurethane prepolymer holding NCO base, wherein NCO content adopts Di-n-Butyl Amine method to measure;
(2) in the product of previous step, add encapsulant reaction, obtain blocked polyurethane prepolymer;
(3) add in the product of previous step neutralizing agent carry out in and, under agitation add deionized water and carry out dispersion and obtain castor oil-base Waterborne Blocked Polyurethane.
6. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 5, it is characterized in that the temperature of reaction described in step (1) is 75-85 DEG C, the reaction times is 2-3h.
7. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 5, it is characterized in that the temperature of reaction described in step (2) is 75-85 DEG C, the reaction times is 2-3h.
8. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 5, is characterized in that the neutral temperature described in step (3) is 55-65 DEG C, in and the time be 0.5-1h.
9. the synthetic method of castor oil-base Waterborne Blocked Polyurethane according to claim 5, is characterized in that the speed of the stirring described in step (3) is 4000-8000r/min.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510981190.4A CN105504206A (en) | 2015-12-24 | 2015-12-24 | Synthetic method of castor oil based enclosed type waterborne polyurethane |
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| CN201510981190.4A CN105504206A (en) | 2015-12-24 | 2015-12-24 | Synthetic method of castor oil based enclosed type waterborne polyurethane |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105821519A (en) * | 2016-05-18 | 2016-08-03 | 四川大学 | Multi-purpose gelatin fiber preparing method based on closed type waterborne polyurethane in-situ cross linking |
| CN106589291A (en) * | 2016-12-29 | 2017-04-26 | 合众（佛山）化工有限公司 | Castor oil terminated polyurethane water-based ink resin and preparation method thereof |
| CN106750139A (en) * | 2016-11-22 | 2017-05-31 | 中国科学院长春应用化学研究所 | Castor oil modified cation aqueous polyurethane resin and preparation method and the waterborne polyurethane resin adhesive |
| CN107200828A (en) * | 2017-05-16 | 2017-09-26 | 枣阳市同邦达科技有限公司 | It is a kind of for polyurethane of one-component coating and preparation method thereof |
| CN111019079A (en) * | 2019-12-20 | 2020-04-17 | 万华化学集团股份有限公司 | Aqueous dispersion of polyurethane or polyurethane urea and preparation method and application thereof |
| CN112760022A (en) * | 2021-01-19 | 2021-05-07 | 四川科路泰交通科技有限公司 | Polyurethane coating and preparation process thereof |
| WO2021118354A1 (en) * | 2019-12-12 | 2021-06-17 | Stahl International B.V. | Preparation of a coating, adhesive, film or sheet |
| CN115181531A (en) * | 2022-09-13 | 2022-10-14 | 山东一诺威聚氨酯股份有限公司 | Vegetable oil-based TPU hot melt adhesive and preparation method thereof |
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| GB996208A (en) * | 1962-01-31 | 1965-06-23 | Thiokol Chemical Corp | Fabric treating composition and process |
| CN102199255A (en) * | 2011-04-07 | 2011-09-28 | 合肥工业大学 | Thermal deblocking type polyurethane-acrylate emulsion and its preparation method |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105821519A (en) * | 2016-05-18 | 2016-08-03 | 四川大学 | Multi-purpose gelatin fiber preparing method based on closed type waterborne polyurethane in-situ cross linking |
| CN106750139A (en) * | 2016-11-22 | 2017-05-31 | 中国科学院长春应用化学研究所 | Castor oil modified cation aqueous polyurethane resin and preparation method and the waterborne polyurethane resin adhesive |
| CN106589291A (en) * | 2016-12-29 | 2017-04-26 | 合众（佛山）化工有限公司 | Castor oil terminated polyurethane water-based ink resin and preparation method thereof |
| CN107200828A (en) * | 2017-05-16 | 2017-09-26 | 枣阳市同邦达科技有限公司 | It is a kind of for polyurethane of one-component coating and preparation method thereof |
| CN107200828B (en) * | 2017-05-16 | 2020-02-18 | 湖北同邦达科技有限公司 | Polyurethane for single-component coating and preparation method thereof |
| WO2021118354A1 (en) * | 2019-12-12 | 2021-06-17 | Stahl International B.V. | Preparation of a coating, adhesive, film or sheet |
| NL2024438B1 (en) * | 2019-12-12 | 2021-09-01 | Stahl Int B V | Preparation of a coating, adhesive, film or sheet |
| CN111019079A (en) * | 2019-12-20 | 2020-04-17 | 万华化学集团股份有限公司 | Aqueous dispersion of polyurethane or polyurethane urea and preparation method and application thereof |
| CN111019079B (en) * | 2019-12-20 | 2022-02-18 | 万华化学集团股份有限公司 | Aqueous dispersion of polyurethane or polyurethane urea and preparation method and application thereof |
| CN112760022A (en) * | 2021-01-19 | 2021-05-07 | 四川科路泰交通科技有限公司 | Polyurethane coating and preparation process thereof |
| CN115181531A (en) * | 2022-09-13 | 2022-10-14 | 山东一诺威聚氨酯股份有限公司 | Vegetable oil-based TPU hot melt adhesive and preparation method thereof |
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