CN105859997A - 3-functionality-degree polycaprolactone urethane acrylate and preparation method and application thereof - Google Patents
3-functionality-degree polycaprolactone urethane acrylate and preparation method and application thereof Download PDFInfo
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- CN105859997A CN105859997A CN201610236456.7A CN201610236456A CN105859997A CN 105859997 A CN105859997 A CN 105859997A CN 201610236456 A CN201610236456 A CN 201610236456A CN 105859997 A CN105859997 A CN 105859997A
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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
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
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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
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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Abstract
The invention discloses low-viscosity 3-functionality-degree polycaprolactone urethane acrylate and a preparation method and application thereof. The preparation method comprises the following step that polycaprolactone triol and isocyanatoethyl prop-2-enoate react to prepare 3-functionality-degree polycaprolactone urethane acrylate. The invention further discloses application of low-viscosity 3-functionality-degree polycaprolactone urethane acrylate to preparation of a UV coating or ink or an adhesive. Polycaprolactone urethane acrylate is prepared from isocyanatoethyl prop-2-enoate, the reaction process is simple and easy to control, gel is not prone to be generated through side reactions, the product viscosity is low, application to construction and UV formula products is benefited, and when polycaprolactone urethane acrylate is used for UV spraying, no solvent or few solvent is added, and the requirement for polycaprolactone urethane acrylate applied to the low-viscosity coating is met. After low-viscosity 3-functionality-degreee polycaprolactone urethane acrylate is cured, the excellent performance of high hardness, wear resistance, scratching resistance, heat resistance, weather fastness and the like is achieved, and low-viscosity 3-functionality-degreee polycaprolactone urethane acrylate can be used as a raw material of the UV coating, the ink and the adhesive.
Description
Technical field
The invention belongs to Material Field, relate to a kind of 3 degree of functionality polycaprolactone polyurethane acrylate and preparation method thereof and answer
With, especially relate to a kind of low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate and its preparation method and application.
Background technology
Along with the strict of solvent is limited by developing rapidly of science and technology with legislations of environmental protection, UV photocuring macromolecular material is more
More it is subject to people's attention.UV photo-curing material has the premium properties such as quick solidifying, energy consumption is low, pollute less, efficiency is high,
Thus it being widely used in the fields such as coating, printing and electronics industry, development in recent years is rapid.Urethane acrylate
(polyurethane acrylate, PUA) is a kind of important Photocurable oligomers, has low stimulation, curing rate fast, high thoroughly
The premium properties such as bright property, stretch-proof, cohesive energy height, are widely used in the fields such as light-curable ink, coating, adhesive, in U.S.
State, Japan, countries in Europe are widely used.In recent years, along with UV-curing technology is in the rise of China, novel light is solid
Formed material as UV coating, ink, binding agent raw material purposes increasingly wider, usage amount is increasing year by year.
Applicant discloses a kind of 3 officials at Chinese patent ZL201310146346.8 (Authorization Notice No. CN 103274967 B)
Energy degree urethane acrylate, is prepared via a method which to obtain: first by 2,2-dihydromethyl propionic acid under catalyst action with ring
Oxidative ethane or propylene oxide reaction and prepared trihydroxy polyether ester, trihydroxy polyether ester again with diisocyanate (selected from HDI,
One in IPDI, HMDI, MDI) and 2-(Acryloyloxy)ethanol or Hydroxypropyl acrylate reaction prepare 3 degree of functionality polyurethane
Acrylate.3 degree of functionality polyurethane third are prepared owing to have employed diisocyanate and 2-(Acryloyloxy)ethanol or Hydroxypropyl acrylate
Olefin(e) acid ester, course of reaction step is many, relatively cumbersome, and production process is wayward, because the existence of side reaction can produce the wind of gel
Danger.
Light-cured resin is the matrix resin of photocureable coating, wide in variety, is widely used.Along with in global range to environmental problem
Pay attention to day by day, light-cured resin will be fast-developing along with the development of photocureable coating.Develop more environmentally-friendly, viscosity
The more excellent light-cured resin of low, combination property is the striving direction of WeiLai Technology personnel.
Summary of the invention
It is a further object of the present invention to provide the preparation method of this low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate.
It is yet another object of the invention to provide the application of this low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate, is prepared via a method which to obtain: by polycaprolactone three
Alcohol (Polycaprolactone triol) and isocyanates ethyl acrylate (2-Isocyanatoethyl Acrylate, is called for short AOI,
No. CAS: 13641-96-8, molecular formula: C6H7NO3, molecular weight: 141.12) reaction prepare 3 degree of functionality polycaprolactones gather
Urethane acrylate.
Reaction scheme is as follows:
Polycaprolactonetriol and isocyanates ethyl acrylate react to obtain 3 degree of functionality polycaprolactone polyurethane acrylate:
R1For:
Preferably, 3 described degree of functionality polycaprolactone polyurethane acrylate are by polycaprolactonetriol and isocyanates acrylic acid
Ethyl ester according to amount ratio 1mol:2.5～3.5mol, at 60 DEG C～95 DEG C reaction and prepare.
It is further preferred that 3 described degree of functionality polycaprolactone polyurethane acrylate are by polycaprolactonetriol and isocyanates
Ethyl acrylate according to amount ratio 1mol:2.9～3mol, catalyst, polymerization inhibitor effect under stir at 80 DEG C～95 DEG C
Insulation reaction 3～6 hours and prepare；Wherein, catalyst is dibutyl tin laurate, and its consumption is polycaprolactonetriol
With isocyanates ethyl acrylate gross mass 100～3000ppm；Polymerization inhibitor can be MEHQ or hydroquinone,
Its consumption is the 100～5000ppm of polycaprolactonetriol and isocyanates ethyl acrylate gross mass.
Present invention reaction is the reaction of the isocyano in isocyanates ethyl acrylate and the hydroxyl of polycaprolactonetriol, belongs to known
Synthesis of polyurethane (polyurethanes) reaction.
The preparation method of 3 degree of functionality polycaprolactone polyurethane acrylate of the present invention, including: polycaprolactonetriol is with different
The reaction of cyanate ethyl acrylate prepares 3 degree of functionality polycaprolactone polyurethane acrylate (i.e. formula (I) compound).
Described polycaprolactonetriol is 1mol:2.5～3.5mol with the amount ratio of isocyanates ethyl acrylate, reaction temperature
It it is 60 DEG C～95 DEG C.
Preferably, polycaprolactonetriol and isocyanates ethyl acrylate are according to amount ratio 1mol:2.9～3mol, in catalysis
Agent, polymerization inhibitor effect under in 80 DEG C～95 DEG C stirring insulation reaction 3～6 hours prepare 3 degree of functionality polycaprolactone polyurethanes third
Olefin(e) acid ester；Wherein, catalyst is dibutyl tin laurate, and its consumption is polycaprolactonetriol and isocyanates ethyl acrylate
The 100～3000ppm of gross mass；Polymerization inhibitor can be MEHQ or hydroquinone, and its consumption is polycaprolactonetriol
With isocyanates ethyl acrylate gross mass 100～5000ppm.
Low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate of the present invention is at preparation UV coating, ink or binding agent
In application.
Beneficial effect:
The present invention uses isocyanates ethyl acrylate to prepare polycaprolactone polyurethane acrylate, decreases reactions steps, reaction
Process is simple, easily controllable, is difficult to produce gel because of side reaction, and polycaprolactone polyurethane acrylate product viscosity is low, more
Be conducive to construction and the application of UV formulation product, be not added with for UV spraying or few solubilizer, meet and be applied to low-viscosity dope
Requirement；Low viscosity 3 degree of functionality UV light-solidifying poly caprolactone urethane acrylate solidification after, have hardness high, wear-resisting,
The premium properties such as scratch resistance, heat-resisting, weatherability, it is possible to the raw material as UV coating, ink, binding agent is applied.
Detailed description of the invention
Embodiment 1
Polycaprolactonetriol (Bai Situo CAPA3050, molecular weight 540) 270 grams is put in 1000mL four-hole boiling flask,
Isocyanates ethyl acrylate 211.5 grams (1.5mol), catalyst dibutyltin dilaurylate 0.3 gram, polymerization inhibitor para hydroxybenzene
Methyl ether 1 gram, is to slowly warm up to 80 DEG C～85 DEG C of insulation reaction 3～discharging in 5 hours for 0.5～4 hour, prepares the knot that is shown below
3 degree of functionality polycaprolactone polyurethane acrylate of structure.
Embodiment 2
Polycaprolactonetriol (Bai Situo CAPA3091, molecular weight 900) 450 grams is put in 1000mL four-hole boiling flask,
Isocyanates ethyl acrylate 211.5 grams (1.5mol), catalyst dibutyltin dilaurylate 0.4 gram, polymerization inhibitor para hydroxybenzene
Methyl ether 1.2 grams, is to slowly warm up to 80 DEG C～85 DEG C of insulation reaction 3～discharging in 5 hours for 0.5～4 hour, prepares and is shown below
3 degree of functionality polycaprolactone polyurethane acrylate of structure.
Embodiment 3
The preparation method of embodiment 1-2 to provide in Chinese patent ZL201310146346.8 prepares the 3 poly-ammonia of degree of functionality
The 3 poly-ammonia of degree of functionality that ester acrylate, as a comparison case 1-2, investigation embodiment of the present invention 1-2 and comparative example 1-2 prepare
The viscosity of ester acrylate.
Method of testing: NDJ-1 type is rotating turns viscometer, No. 4 rotors, 60 revs/min.Concrete operation step is with reference to " NDJ-1
Type rotating cylinder viscometer operation instructions ".
The viscosity of table 13 degree of functionality polycaprolactone polyurethane acrylate
| Comparative example 1 | Embodiment 1 | Comparative example 2 | Embodiment 2 | |
| Viscosity | 7200mPa.s@60℃ | 4100mPa.s@60℃ | 7700mPa.s@60℃ | 4400mPa.s@60℃ |
Embodiment 1 product comparison ratio 1 product viscosity declines 3100mPa.s@60 DEG C, and fall is 43.06%.
Embodiment 2 product comparison ratio 2 product viscosity declines 3300mPa.s@60 DEG C, and fall is 42.86%.
Embodiment 4
Raw material
UV resin is 1.: the low viscosity 3 degree of functionality aliphatic poly caprolactone urethane acrylate of embodiment 1 preparation (uses 3
The purpose of degree of functionality aliphatic urethane acrylate is to increase the hardness of film, intensity, the performance such as wear-resisting)；
UV resin is 2.: low viscosity 2 degree of functionality aliphatic urethane acrylate (uses 2 degree of functionality aliphatic polyurethane propylene
The purpose of acid esters is to increase the flexibility of film, anti-riot splits, cold-hot cycle performance), preparation method is as follows:
Polycaprolactone glycol (Bai Situo CAPA2100, molecular weight 1000) 500 grams is put in 1000mL four-hole boiling flask,
Isocyanates ethyl acrylate 141 grams (1mol), catalyst dibutyltin dilaurylate 0.1 gram, polymerization inhibitor para hydroxybenzene first
0.7 gram of ether, is to slowly warm up to 80 DEG C～85 DEG C of insulation reaction 3～discharging in 5 hours for 0.5～4 hour, prepares the knot that is shown below
2 degree of functionality polycaprolactone polyurethane acrylate of structure.
R is:
I.e. in polycaprolactone glycol, dihydroxylic alcohols initiator is neopentyl glycol；
A+b=(1000-104)/114=7.8596.
The viscosity using viscosity determining procedure same as in Example 3 to record 2 degree of functionality aliphatic urethane acrylates is
2900mPa.s@60℃。
UV monomer: pentaerythritol triacrylate (PETA, Jiangsu Litian Technology Co., Ltd.)；1,6-HD two
Acrylate (HDDA, profit field, Jiangsu).
Light trigger: 1173, Nanjing Wa Li Chemical Industry Science Co., Ltd.
Auxiliary agent: Tego432, Tego92, Germany's enlightening is high.
Mixed solvent: butyl acetate, toluene, methylisobutylketone mix for 1:1:1 in mass ratio.
Instrument and equipment
LT-1002 type uv cure machine, blue sky Te Deng Development Co., Ltd；QFZ type paint film adhesion analyzer, Tianjin
Ke Lian Material Testing Machine factory；RCA paper tape wear resistant instrument, Shanghai modern environment project institute；Water-bath；Cold cycling
Equipment.
The preparation of coating
Weighing the UV resin of certain mass, be subsequently adding UV monomer, mixed solvent, light trigger, auxiliary agent, stirring is all
Even, it is configured to coating.The proportioning of coating is shown in Table 2.
The proportioning of table 2 coating
The preparation of film and solidification
Select the ABS plastic sheet material of 10cm × 10cm, first at one layer of thermoplastic acrylic resin white primer of its surface spraying,
60 DEG C of baking 3h, then the UV coating prepared according to table 2 at its surface spraying, coating thickness is about 20 μm, on photo solidification machine
Solidification, makes cured film reach surface drying, characterizes by tack method, records hardening time.
Performance test
Hardening time: experiment uses tack method, touches coating surface with finger, if do not felt tacky, i.e. think coating surface
Cured.
Pencil hardness: measure with reference to GB 6739-86 film pencil hardness method.
Adhesive force: measure with reference to GB/T 1720-88 film adhesive algoscopy.Being divided into 7 grades, 1 grade optimal, and 7 grades
Difference.
Wearability: RCA tests, 175g, 500 ± 50 times.
Water boiling resistance: with reference to standard GB/T/T 1733 " paint film resistance to water algoscopy ".
Cold-hot circulates:
(1) scope and explanation: plastic paint is because of moisture and hot ageing or losses of plasticizer, or both hold concurrently it sometimes appear that ftractures becomes
Gesture, uses and is alternately exposed in climate cabinet and household freezer to measure the degree whether paint film ftractures and ftracture.
(2) instrument: 1. damp heat box, 2. household freezer, 3. colour photometer, 4. draws lattice device.
(3) assay method: 1. test piece is put into relative temperature 100%, temperature is 24h in the incubator hot tank of 38 DEG C.Sample
The placement of plate with a vertical 0-30 degree angle, and should require that plate plate is not in contact with each other in process of the test mutually.2. after 24h, immediately
Model is moved to 20h in the household freezer of (-23 ± 1.5) DEG C, is at most not to be exceeded 30S transfer time.3. model is taken out,
Ambient temperatare puts 4h, and 48h is a circulation the most altogether, and period can carry out stage evaluation.Carry out 15 circulations the most altogether, so
Afterwards model outward appearance, color, adhesive force are tested.
(4) result represents: film should be without cracking, variable color, loss of adhesion or other defect.
(5) reference standard: Unite States Standard AAMA 615-02 " advise on plastic material by the industry of high-performance organic coating
Model, performance requirement and test method ".(1)
Result and discussion, the resin impact on film performance
UV resin is the main body of UV coating, and its performance substantially determines the main performance of film after solidification.This experiment is adopted
Form different with 3 degree of functionality aliphatic poly caprolactone urethane acrylates and 2 degree of functionality aliphatic urethane acrylate resins
Formula, various Ingredient Amount are shown in Table 2, and film performance is shown in Table 3.
Table 33 degree of functionality urethane acrylate and the impact on coating property of the 2 degree of functionality urethane acrylate different ratio
List of references: (1) Yu Yingying. the coatings industry method of inspection is complete works of with instrument. Beijing: Chemical Industry Press,
2007:525.
Attached light trigger 1173 illustrates:
Manufacturer: Nanjing Wa Li Chemical Industry Science Co., Ltd
Chemical name: 2-hydroxy-2-methyl-1-phenyl-1-acetone
English name: 2-Hydroxy-2-methyl-1-phenyl-propan-1-one
CAS NO:7473-98-5
Molecular formula: C10H12O
Molecular weight: 164.2
Chemical structural formula:
Technical specification:
Outward appearance: colourless to light yellow transparent liquid
Purity: >=99.0%
Boiling point: 80-81 DEG C (degree Celsius)
Light transmittance: 425nm >=99.0%；500nm >=99.3%
Fugitive constituent :≤0.2%
Ash :≤0.10%
Application:
1173 are applicable to acrylic acid photocuring varnish system, such as the varnish etc. of timber, metal, paper, plastics etc..1173 is special
Recommend needing to stand chronic sun exposure and in the UV-curable coating of color inhibition, owing to 1173 is liquid, be highly susceptible to being blended,
So being suitable for use compounding with other light trigger, it is proposed that addition is 1～4%w/w.
Claims (9)
1. a degree of functionality polycaprolactone polyurethane acrylate, it is characterised in that it is prepared via a method which to obtain: by
Polycaprolactonetriol and isocyanates ethyl acrylate react and prepare 3 degree of functionality polycaprolactone polyurethane acrylate.
3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 1, it is characterised in that 3 described officials
Energy degree polycaprolactone polyurethane acrylate is according to amount ratio 1mol by polycaprolactonetriol and isocyanates ethyl acrylate:
2.5～3.5mol, at 60 DEG C～95 DEG C reaction and prepare.
3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 2, it is characterised in that 3 described officials
Energy degree polycaprolactone polyurethane acrylate is according to amount ratio 1mol by polycaprolactonetriol and isocyanates ethyl acrylate:
2.9～3mol, catalyst, polymerization inhibitor effect under at 80 DEG C～95 DEG C, stir insulation reaction 3～6 hours and prepare.
3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 3, it is characterised in that catalyst is two
Dibutyl tin laurate, its consumption is the 100～3000ppm of polycaprolactonetriol and isocyanates ethyl acrylate gross mass；
Polymerization inhibitor is MEHQ or hydroquinone, and its consumption is polycaprolactonetriol and isocyanates ethyl acrylate gross mass
100～5000ppm.
5. the preparation method of 3 degree of functionality polycaprolactone polyurethane acrylate described in claim 1, it is characterised in that bag
Include: polycaprolactonetriol and isocyanates ethyl acrylate react and prepare 3 degree of functionality polycaprolactone polyurethane acrylate.
The preparation method of 3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 5, it is characterised in that
Described polycaprolactonetriol is 1mol:2.5～3.5mol with the amount ratio of isocyanates ethyl acrylate, and reaction temperature is
60 DEG C～95 DEG C.
The preparation method of 3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 6, it is characterised in that
Polycaprolactonetriol and isocyanates ethyl acrylate are according to amount ratio 1mol:2.9～3mol, at catalyst, the work of polymerization inhibitor
3 degree of functionality polycaprolactone polyurethane acrylate are prepared in 80 DEG C～95 DEG C stirring insulation reaction 3～6 hours under with.
The preparation method of 3 degree of functionality polycaprolactone polyurethane acrylate the most according to claim 7, it is characterised in that
Catalyst is dibutyl tin laurate, its consumption be polycaprolactonetriol with the 100 of isocyanates ethyl acrylate gross mass～
3000ppm；Polymerization inhibitor is MEHQ or hydroquinone, and its consumption is polycaprolactonetriol and isocyanates acrylic acid second
The 100～5000ppm of ester gross mass.
9. the low viscosity 3 degree of functionality polycaprolactone polyurethane acrylate described in claim 1 is at preparation UV coating, ink
Or the application in binding agent.
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