CN102702837B - Emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and preparation method for emulsifying agent - Google Patents
Emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and preparation method for emulsifying agent Download PDFInfo
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- CN102702837B CN102702837B CN2012101976680A CN201210197668A CN102702837B CN 102702837 B CN102702837 B CN 102702837B CN 2012101976680 A CN2012101976680 A CN 2012101976680A CN 201210197668 A CN201210197668 A CN 201210197668A CN 102702837 B CN102702837 B CN 102702837B
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- cured coating
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- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 40
- 238000000576 coating method Methods 0.000 title claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000011248 coating agent Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- 229940096998 ursolic acid Drugs 0.000 claims description 2
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- 239000003973 paint Substances 0.000 abstract description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 abstract 1
- 230000008569 process Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- Y02P20/121—
Landscapes
- Paints Or Removers (AREA)
Abstract
The invention discloses an emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and a preparation method for the emulsifying agent. The method comprises the following steps of: mixing trimethylolpropane, acrylic acid, a solvent, a catalyst and hydroquinone monomethyl ether and reacting, adding ethylene oxide, continuously reacting, and removing the solvent under vacuum to obtain the emulsifying agent for the environment-friendly UV photocureable coating. The prepared emulsifying agent is high in dispersing speed, uniform in dispersing, high dispersing stability and paint film property, and is environment-friendly, and saves energy.
Description
Technical field
The present invention relates to a kind of coating emulsifying agent, relate to more specifically a kind of environment protection water-based UV photo-cured coating emulsifying agent, be used for water-borne coatings emulsion dispersion system, the invention also discloses the preparation method of described emulsifying agent.
Background technology
Raising along with environmental consciousness in world wide and environmentfriendly products requirement, people are more and more higher to performance requriementss such as the decoration of coating, protection against corrosion, heatproof, cold-resistant, stain resistants, and world coatings industry is by the direction develop rapidly of solvent-borne type to high-performance, pollution-free, environment-friendly aqueous coating.
UV-curing technology has obtained the development of advancing by leaps and bounds with its tight knot energy environmental protection, production efficiency high at nearly 20 years.
Water base UV coating makes its application more and more extensive due to the feature performance benefit that combines water-borne coatings and UV-curing technology.Yet in the production UV-curable waterborne coatings, use traditional low molecule emulsifying agent often to cause that polymer emulsion is low to the adhesivity of base material, the side effects such as film poor water resistance, the glossiness that forms is low, face oil impregnate and illumination low molecular weight volatile affect the coating end properties.A large amount of studies show that in recent years, some superpolymer also have extremely strong interfacial activity, and they compare low-molecular-weight surfactant, have that anti-high humidity, emulsifying capacity are strong, the dispersed advantage such as good.The synthetic emulsifying agent with the latex structural similitude of design can effectively solve and improve consistency, stability and the paint film property of emulsifying agent and matrix resin.
At present in the water-borne coatings field, a lot of for the development research of macromolecule reaction type emulsifying agent.Mainly be divided in emulsion polymerization process use and film process in use two classes to use: last class application is by introduce reactive emulsifier in the emulsifier-free emulsion polymerization process, utilize larger molecular weight and polymer to connect hydrophobic binding point on section, macromolecule emulsifier effectively is adsorbed on latex particle, thereby reduces the defective that the surfactivity migration brings; A rear class is the emulsifying agent of introducing in film process with the crosslinkable reaction, makes emulsifying agent and matrix resin crosslinking reaction form three-dimensional arrangement, improves solvent resistance and the mechanical stability of paint film.
In water base UV coating material production, the introducing of last class reactive emulsifier can be influential to reaction conditions and synthetic control, and some side reactions may occur, and affects end properties, and little in the help of coating radiation crosslinking film process; A rear class reactive emulsifier, not obvious to the rapid water emulsifying effectiveness of coating resin main body, and many this type of reactive emulsifiers in use need higher temperature just can carry out crosslinking reaction, and this makes troubles to practical application, also consumes simultaneously the energy.As N hydroxymethyl acrylamide system of hydroxyl and trimeric cyanamide system, self-crosslinking etc.
Summary of the invention
One of purpose of the embodiment of the present invention is to provide a kind of novel aqueous UV curing coating emulsifying agent, can improve the quick emulsification in the paint emulsification technological process and disperse the homogeneous performance, and effect is good.
The present invention adopts following technical scheme:
A kind of environment protection water-based UV photo-cured coating emulsifying agent has following structural formula:
Wherein n is the natural number of 8-18.
Further scheme is: the number-average molecular weight that described environment protection water-based UV photo-cured coating is used emulsifying agent is at 600-1000, and its second-order transition temperature is at-25 ℃ to 80 ℃.
Another purpose of the embodiment of the present invention is to provide the preparation method of a kind of environment protection water-based UV photo-cured coating with emulsifying agent, comprising:
(1) prepare various components according to following part by weight:
(2) other components except oxyethane in above-mentioned various components are mixed and stirred, be warming up to 120 ℃, the insulation back flow reaction is complete, then add oxyethane to continue reaction, after the oxyethane complete reaction, vacuumizing maintenance reaction system vacuum tightness is 0.09-0.1MPa, controls temperature and sloughs solvent at 70-80 ℃, slough cooling discharging after solvent, namely get environment protection water-based UV photo-cured coating emulsifying agent.
Further scheme is: described solvent is a kind of in toluene or dimethylbenzene.
Further scheme is: described catalyzer is a kind of in tosic acid, methanesulfonic, silicon ursolic acid or organotin.
The principal reaction process roughly can be with reference to following reaction formula:
The emulsifying agent of the present invention's preparation, the shortcoming according to existing emulsifying agent adopts rational molecule architecture design, improves for the basis of existing emulsifying agent shortcoming, and makes breakthrough.By introduce a plurality of pairs of keys and hydrophilic radical in the emulsifying agent molecule, make the matrix resin can Quick uniform emulsification, can with monomer generation free radicals copolymerization reaction, be cross-linked to form T-shaped paint film with paint film, thereby improve solvent resistance, stability and the mechanical property of coating.Therefore the emulsifying agent made of the present invention have rate of dispersion fast, be uniformly dispersed, dispersion stabilization is good, energy-conserving and environment-protective and better paint film property.
Embodiment
Below by specific embodiment, technology contents of the present invention is described further, but protection scope of the present invention is not limited by embodiment.
Embodiment 1:
(1) successively put in there-necked flask according to following weight ratio following each component except oxyethane:
(2). adopt progressively intensification, stage feed way, soon in step (1), each component except oxyethane mixes, temperature of reaction is risen to 120 ℃, the insulation back flow reaction, collect with water trap the water that condensation produces, by the amount judgement level of response of water outlet, react the oxyethane that adds calculated amount when aquifer yield reaches theoretical value and continue reaction, to the oxyethane complete reaction, finish reaction.
(3) decompression vacuum pumping, vacuum tightness 0.1MPa sloughs solvent at 80 ℃, cooling environment protection water-based UV photo-cured coating emulsifying agent.
Embodiment 2:
(1) successively put in there-necked flask according to following weight ratio following each component except oxyethane:
(2) adopt progressively intensification, stage feed way, soon in step (1), each component except oxyethane mixes, temperature of reaction is risen to 120 ℃, the insulation back flow reaction, collect with water trap the water that condensation produces, by the amount judgement level of response of water outlet, react the oxyethane that adds calculated amount when aquifer yield reaches theoretical value and continue reaction, to the oxyethane complete reaction, finish reaction.
(3) decompression vacuum pumping, vacuum tightness are 0.09MPa, slough solvent at 70 ℃, cooling environment protection water-based UV photo-cured coating emulsifying agent.
Embodiment 3:
(1) successively put in there-necked flask according to following weight ratio following each component except oxyethane:
(2) adopt progressively intensification, stage feed way, soon in step (1), each component except oxyethane mixes, temperature of reaction is risen to 120 ℃, the insulation back flow reaction, collect with water trap the water that condensation produces, by the amount judgement level of response of water outlet, react the oxyethane that adds calculated amount when aquifer yield reaches theoretical value and continue reaction, to the oxyethane complete reaction, finish reaction.
(3) decompression vacuum pumping, vacuum tightness 0.095MPa sloughs solvent at 75 ℃, cooling environment protection water-based UV photo-cured coating emulsifying agent.
The average behaviour of the product by the present embodiment one to three preparation contrasts as following table with common market product performance:
Claims (3)
1. environment protection water-based UV photo-cured coating is with the preparation method of emulsifying agent, and described environment protection water-based UV photo-cured coating has following structural formula with emulsifying agent:
Wherein n is the natural number of 8-18;
The number-average molecular weight that described environment protection water-based UV photo-cured coating is used emulsifying agent is at 600-1000, and second-order transition temperature is at-25 ℃ to 80 ℃;
It is characterized in that comprising:
(1) prepare various components according to following part by weight:
(2) other components except oxyethane in above-mentioned various components are mixed and stirred, be warming up to 120 ℃, the insulation back flow reaction is complete, then add oxyethane to continue reaction, after the oxyethane complete reaction, vacuumizing maintenance reaction system vacuum tightness is 0.09-0.1MPa, controls temperature and sloughs solvent at 70-80 ℃, slough cooling discharging after solvent, namely get environment protection water-based UV photo-cured coating emulsifying agent.
2. environment protection water-based UV photo-cured coating with the preparation method of emulsifying agent, is characterized in that described solvent is a kind of in toluene or dimethylbenzene according to claim 1.
3. environment protection water-based UV photo-cured coating with the preparation method of emulsifying agent, is characterized in that described catalyzer is a kind of in tosic acid, methanesulfonic, silicon ursolic acid or organotin according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101976680A CN102702837B (en) | 2012-06-15 | 2012-06-15 | Emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and preparation method for emulsifying agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101976680A CN102702837B (en) | 2012-06-15 | 2012-06-15 | Emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and preparation method for emulsifying agent |
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| Publication Number | Publication Date |
|---|---|
| CN102702837A CN102702837A (en) | 2012-10-03 |
| CN102702837B true CN102702837B (en) | 2013-11-06 |
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| CN2012101976680A Active CN102702837B (en) | 2012-06-15 | 2012-06-15 | Emulsifying agent for environment-friendly water-based ultraviolet (UV) photocureable coating and preparation method for emulsifying agent |
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| CN110746587B (en) * | 2019-06-11 | 2022-02-15 | 扬州工业职业技术学院 | Preparation method of macromolecular emulsifier capable of undergoing free radical copolymerization |
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| DE4232013A1 (en) * | 1992-09-24 | 1994-03-31 | Bayer Ag | Polyurethanes containing acryloyl groups, a process for their preparation and their use as binders for coating compositions |
| CN1844229A (en) * | 2006-05-16 | 2006-10-11 | 广东工业大学 | UV curable aqueous resin composition |
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Owner name: ZHONGWU FUNCTION MATERIAL INSTITUTE CO., LTD. Free format text: FORMER OWNER: SICHUAN RESEARCH CENTER OF NEW MATERIALS Effective date: 20140806 |
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Effective date of registration: 20140806 Address after: 518040, Shenzhen, Guangdong, Futian District, Che Kung Temple Tian An Digital City Futian Tian Tian hi tech building A block 402 room Patentee after: SINOMATERIAL FUNCTION MATERIAL INSTITUTE CO.,LTD. Address before: 610000, No. 24, No. 1, south section of No. 1 Ring Road, Sichuan, Chengdu, No. 312 Patentee before: Sichuan Research Center of New Materials |
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Address after: 518040, Shenzhen, Guangdong, Futian District, Che Kung Temple Tian An Digital City Futian Tian Tian hi tech building A block 402 room Patentee after: LENGINE DEFENSE TECHNOLOGY GROUP CO.,LTD. Address before: 518040, Shenzhen, Guangdong, Futian District, Che Kung Temple Tian An Digital City Futian Tian Tian hi tech building A block 402 room Patentee before: SINOMATERIAL FUNCTION MATERIAL INSTITUTE CO.,LTD. |
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Denomination of invention: An environmentally friendly emulsifier for water-based UV curable coatings and its preparation method Effective date of registration: 20210208 Granted publication date: 20131106 Pledgee: Bank of Beijing Limited by Share Ltd. Shenzhen branch Pledgor: LENGINE DEFENSE TECHNOLOGY GROUP Co.,Ltd. Registration number: Y2021980001151 |
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Date of cancellation: 20220805 Granted publication date: 20131106 Pledgee: Bank of Beijing Limited by Share Ltd. Shenzhen branch Pledgor: LENGINE DEFENSE TECHNOLOGY GROUP CO.,LTD. Registration number: Y2021980001151 |