CN108003779A - A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins - Google Patents
A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins Download PDFInfo
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- CN108003779A CN108003779A CN201711370211.4A CN201711370211A CN108003779A CN 108003779 A CN108003779 A CN 108003779A CN 201711370211 A CN201711370211 A CN 201711370211A CN 108003779 A CN108003779 A CN 108003779A
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- nco
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- saccharide compound
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- C08G18/44—Polycarbonates
-
- 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
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
It is an object of the invention to provide a kind of preparation method that UV solidfication water polyurethanes are modified using bio-based materials saccharide compound.The polyester-type aqueous polyurethane of the present invention contains saccharide polyesters type aqueous polyurethane through the terminal-modified main chain that obtains of saccharide compound, and after the polymer film forming, polymer ends carbohydrate segment is more likely to surface spreading, and polyurethane segment is towards internal layer.So it can assign modified polyurethane film excellent water-wet behavior again while the excellent adhesive force of polyester urethane resin, hardness, solidification rate etc. is ensured.
Description
Technical field
The invention belongs to technical field of polymer materials, and in particular to a kind of bio-based materials are modified the poly- ammonia of UV curable water-bornes
The preparation method of ester resin
Background introduction
The many advantages of traditional UV curing technologies and water paint technology are inherited and developed to UV-Curing Waterborne Resin,
Such as low cost, low viscosity, good coating adaptability, equipment are simple, non-toxic, nonirritant, noninflammability.Since UV cures
The advantages of water-base resin, protrudes, and is developed faster in recent years, its product is by various fields application.
Industrial expansion, huge infringement is brought to environment, in recent years, it is increasingly recognised that our living environments
Importance, economic development while will also ensure that environment is not destroyed.Bio-based materials are made since its is environmentally protective, saves
The characteristics of energy, has obtained extensive concern, and bio-based materials industry development at present is swift and violent, and technology is constantly broken through, no matter from species
And have very big leap in purposes.Saccharide compound has also obtained very big in recent years as one kind in bio-based materials
Development, saccharide compound not only abundance, but also environmental protection, is all applied in every field now.
Saccharide compound is a kind of polyol, and hydrophily is high, and the parent that can improve polymer is combined with polymer
Water-based energy, reduces the viscosity of polymer, improves the gloss effect of polymer.Can be significantly using saccharide compound modified polyurethane
The hydrophilicity of polyurethane film is improved, the characteristics of polyurethane film is easily dirty is solved, reaches anti-fouling effect, its water-wet behavior, additionally it is possible to
Antifog characteristic is brought to polyurethane film.
The content of the invention
It is an object of the invention to provide one kind UV solidfication water polyurethanes are modified using bio-based materials saccharide compound
Preparation method.The polyester-type aqueous polyurethane of the present invention contains saccharide polyesters type through the terminal-modified main chain that obtains of saccharide compound
Aqueous polyurethane, after the polymer film forming, polymer ends carbohydrate segment is more likely to surface spreading, and polyurethane segment direction
Internal layer.It so can again assign and change while the excellent adhesive force of polyester urethane resin, hardness, solidification rate etc. is ensured
The property excellent water-wet behavior of polyurethane coating film.
The technical scheme is that：
A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins, include the following steps：
(1) polyester diol is warming up to 80-100 DEG C, vacuum dehydration processing 30min, obtains dewatered polyester binary
Alcohol and hydroxy silicon oil；
(2) NCO half blocks the synthesis of the prepolymer containing saccharide compound：A certain amount of catalyst and diisocyanate are added
Temperature is risen to 50-55 DEG C in 250ml three-necked flasks a certain amount of polyester diol is added dropwise, react 2-3h, when NCO reaches theoretical
Terminate during value, obtain just aggressiveness.First mer temperature is controlled at 60-65 DEG C again, adds chain extender reaction 2-3h when NCO reaches reason
By be warming up to after value 75-80 DEG C add saccharide compound, polymerization inhibitor, solvent orange 2 A insulation reaction 3 it is small when, NCO reaches theoretical value, instead
It should stop, obtaining isocyanate-terminated prepolymer containing saccharide compound；
(3) NCO half blocks the synthesis of the prepolymer of agent containing active termination：A certain amount of catalyst and diisocyanate are added
Temperature is risen to 50-55 DEG C in 250ml three-necked flasks a certain amount of polyester diol is added dropwise, reaction 2-3h reaches theoretical as NCO
Terminate during value, obtain just aggressiveness.First mer temperature is controlled at 60-65 DEG C again, adds chain extender reaction 2-3h when NCO reaches reason
Reach theoretical value by 60-65 DEG C of agent of addition active termination, polymerization inhibitor, solvent orange 2 A insulation reaction 2h, NCO is cooled to after value, reaction stops
Only, the isocyanate-terminated prepolymer of agent containing active termination is obtained；
(4) preparation of aqueous polyurethane emulsion：A certain amount of catalyst, Branched polyol are added into 250ml three-necked flasks
It is middle that temperature is risen to 75-80 DEG C, the isocyanate-terminated prepolymer containing saccharide compound of different content is added under nitrogen atmosphere
With the isocyanate-terminated prepolymer of agent containing active termination.When reaction 3-4 is small, terminated when-NCO infrared absorption peaks are wholly absent anti-
Should.Reaction temperature is down to 50 DEG C, adds a certain amount of neutralizer, high speed shear 30min, adds deionized water, shearing breast
Change 30min, vacuum rotary steam removes solvent orange 2 A, up to bio-based materials modified aqueous polyurethane emulsion；
Saccharide compound described in step (2) is at least one of sucrose, fructose, maltose；
Chain extender described in step (2) and (3) for dihydromethyl propionic acid (DMPA), in dimethylolpropionic acid (DMBA) extremely
Few one kind；
Catalyst described in step (2), (3) and (4) is at least one of dibutyl tin laurate, stannous octoate；
Diisocyanate described in step (2) and (3) is toluene di-isocyanate(TDI) (TDI), 4,4'- diphenyl methanes two are different
Cyanate (MDI), isophorone diisocyanate (IPDI), two isocyanide of hexamethylene diisocyanate (HDI) dicyclohexyl methyl hydride
At least one of sour cruel (HMDI)；
Active termination agent described in step (3) is hydroxy-ethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA), third
At least one of olefin(e) acid hydroxypropyl acrylate (HPA), hydroxy propyl methacrylate (HPMA), pentaerythritol triacrylate (PETA)；
Polymerization inhibitor described in step (2) and (3) is at least one of hydroquinone, p methoxy phenol；
Polyester diol described in step (2) and (3) is polycarbonate glycol, polycaprolactone diols, adipic acid gather
At least one of ester dihydric alcohol；
Neutralizer described in step (4) is triethylamine；
Solvent orange 2 A described in step (2), (3) and (4) is in acetone, butanone, N,N-dimethylformamide and dimethyl sulfoxide
It is at least one.
The beneficial effects of the invention are as follows：Reacted more than, it is water-based poly- that synthesis obtains water-fast, weather-proof, hydrophilic UV curable
Urethane cold coating resin.The resin can be used for improving the water resistance of coating, weatherability, soil resistance, heat resistance, it is anti-fog properties,
Self-cleaning property, can be widely used for vehicle window, door and window etc. has water-fast, weather-proof, antifouling, antifog, automatically cleaning requirement surface.
Embodiment
Embodiment 1
NCO half blocks the synthesis of the prepolymer containing saccharide compound：By 0.03g dibutyl tin laurates (DTBDL) and
4.58g isophorone diisocyanate (IPDI) adds in 100ml three-necked flasks temperature rising to 65 DEG C, is added dropwise under nitrogen atmosphere
4g polycarbonate glycol, reaction 2h terminate when NCO reaches theoretical value, obtain just aggressiveness.First mer temperature is controlled 70 again
DEG C, add 1.34g dihydromethyl propionic acids (DMPA) reaction 2h be warming up to when NCO reaches theoretical value after 80 DEG C of addition 1.87g sucrose,
When 0.01g p methoxy phenols, 5.0g acetone insulation reaction 3 are small, NCO reaches theoretical value, and reaction stops, and NCO half is blocked containing sugar
Class compound prepolymer；
NCO half blocks the synthesis of the prepolymer of agent containing active termination：By 0.03g dibutyl tin laurates (DTBDL) and
9.16g isophorone diisocyanate (IPDI) adds in 100ml three-necked flasks temperature rising to 60 DEG C, is added dropwise under nitrogen atmosphere
8g polycarbonate glycol, reaction 4 terminate when small when NCO reaches theoretical value, obtain just aggressiveness.First mer temperature is controlled again
At 80 DEG C, addition 2.67g dihydromethyl propionic acids (DMPA) reaction 3 cools to 60 DEG C of additions when small after NCO reaches theoretical value
The agent of 1.34g hydroxyethyl methacrylates (HEMA) active termination, 0.01g p methoxy phenols, 5.0g acetone insulation reaction 3 are small
When, NCO reaches theoretical value, and reaction stops, and NCO half blocks the prepolymer of agent containing active termination；
The preparation of aqueous polyurethane emulsion：By 0.09g dibutyl tin laurates (DTBDL), 0.67g trimethylolpropanes
(TMP) temperature in 250ml three-necked flasks is added with 15g acetone and rises to 65 DEG C, it is pre- containing saccharide compound to add half end-blockings of above NCO
Polymers and NCO half block the prepolymer of agent containing active termination.React 4 it is small when, terminated when-NCO infrared absorption peaks are wholly absent anti-
Should.Reaction temperature is down to 0 DEG C, adds 4g triethylamine neutralizers, high speed shear 30min, adds 120g deionized waters, shearing
40min is emulsified, vacuum rotary steam removes acetone, up to hyperbranched aqueous polyurethane lotion.
Claims (2)
1. a kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins, include the following steps：
(1) polyester diol is warming up to 80-100 DEG C, vacuum dehydration processing 30min, obtain dewatered polyester diol and
Hydroxy silicon oil；
(2) NCO half blocks the synthesis of the prepolymer containing saccharide compound：A certain amount of catalyst and diisocyanate are added
Temperature is risen to 50-55 DEG C in 250ml three-necked flasks a certain amount of polyester diol is added dropwise, react 2-3h, when NCO reaches theoretical
Terminate during value, obtain just aggressiveness.First mer temperature is controlled at 60-65 DEG C again, adds chain extender reaction 2-3h when NCO reaches reason
By be warming up to after value 75-80 DEG C add saccharide compound, polymerization inhibitor, solvent orange 2 A insulation reaction 3 it is small when, NCO reaches theoretical value, instead
It should stop, obtaining isocyanate-terminated prepolymer containing saccharide compound；
(3) NCO half blocks the synthesis of the prepolymer of agent containing active termination：A certain amount of catalyst and diisocyanate are added
Temperature is risen to 50-55 DEG C in 250ml three-necked flasks a certain amount of polyester diol is added dropwise, reaction 2-3h reaches theoretical as NCO
Terminate during value, obtain just aggressiveness.First mer temperature is controlled at 60-65 DEG C again, adds chain extender reaction 2-3h when NCO reaches reason
Reach theoretical value by 60-65 DEG C of agent of addition active termination, polymerization inhibitor, solvent orange 2 A insulation reaction 2h, NCO is cooled to after value, reaction stops
Only, the isocyanate-terminated prepolymer of agent containing active termination is obtained；
(4) preparation of aqueous polyurethane emulsion：A certain amount of catalyst, Branched polyol are added in 250ml three-necked flasks will
Temperature rises to 75-80 DEG C, adds the isocyanate-terminated prepolymer containing saccharide compound of different content and different under nitrogen atmosphere
Cyanate blocks the prepolymer of agent containing active termination.When reaction 3-4 is small, reaction is terminated when-NCO infrared absorption peaks are wholly absent.
Reaction temperature is down to 50 DEG C, adds a certain amount of neutralizer, high speed shear 30min, adds deionized water, emulsification pretreatment
30min, vacuum rotary steam removes solvent orange 2 A, up to bio-based materials modified aqueous polyurethane emulsion.
2. a kind of bio-based materials as claimed in claim 1 are modified the preparation method of UV solidfication water polyurethane resins, it is special
Sign is：
Saccharide compound described in step (2) is at least one of sucrose, fructose, maltose；
Chain extender described in step (2) and (3) is at least one in dihydromethyl propionic acid (DMPA), dimethylolpropionic acid (DMBA)
Kind；
Catalyst described in step (2), (3) and (4) is at least one of dibutyl tin laurate, stannous octoate；
Diisocyanate described in step (2) and (3) is toluene di-isocyanate(TDI) (TDI), 4,4'- diphenylmethane diisocyanates
Ester (MDI), isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI) dicyclohexyl methyl hydride diisocyanate are cruel
At least one of (HMDI)；
Active termination agent described in step (3) is hydroxy-ethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA), acrylic acid
At least one of hydroxypropyl acrylate (HPA), hydroxy propyl methacrylate (HPMA), pentaerythritol triacrylate (PETA)；
Polymerization inhibitor described in step (2) and (3) is at least one of hydroquinone, p methoxy phenol；
Polyester diol described in step (2) and (3) is polycarbonate glycol, polycaprolactone diols, adipate polyester two
At least one of first alcohol；
Neutralizer described in step (4) is triethylamine；
Solvent orange 2 A described in step (2), (3) and (4) be acetone, butanone, N,N-dimethylformamide and dimethyl sulfoxide at least
It is a kind of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711370211.4A CN108003779A (en) | 2017-12-19 | 2017-12-19 | A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711370211.4A CN108003779A (en) | 2017-12-19 | 2017-12-19 | A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins |
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| CN108003779A true CN108003779A (en) | 2018-05-08 |
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| CN201711370211.4A Pending CN108003779A (en) | 2017-12-19 | 2017-12-19 | A kind of bio-based materials are modified the preparation method of UV solidfication water polyurethane resins |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111269380A (en) * | 2018-12-04 | 2020-06-12 | 南通立方新材料科技有限公司 | Photocuring arabinose-based polyurethane acrylate and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845133A (en) * | 2010-04-01 | 2010-09-29 | 陕西科技大学 | Method for preparing natural polyhydroxy compound modified aqueous polyurethane emulsion |
| CN104448211A (en) * | 2014-12-19 | 2015-03-25 | 江南大学 | Method for preparing UV-cured, fluorinated and hyperbranched waterborne polyurethane resin |
-
2017
- 2017-12-19 CN CN201711370211.4A patent/CN108003779A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845133A (en) * | 2010-04-01 | 2010-09-29 | 陕西科技大学 | Method for preparing natural polyhydroxy compound modified aqueous polyurethane emulsion |
| CN104448211A (en) * | 2014-12-19 | 2015-03-25 | 江南大学 | Method for preparing UV-cured, fluorinated and hyperbranched waterborne polyurethane resin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111269380A (en) * | 2018-12-04 | 2020-06-12 | 南通立方新材料科技有限公司 | Photocuring arabinose-based polyurethane acrylate and preparation method thereof |
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Application publication date: 20180508 |