CN102134416B - Fluorine-containing acrylate leveling agent for environment-friendly type water-soluble coating - Google Patents
Fluorine-containing acrylate leveling agent for environment-friendly type water-soluble coating Download PDFInfo
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- CN102134416B CN102134416B CN2011100594792A CN201110059479A CN102134416B CN 102134416 B CN102134416 B CN 102134416B CN 2011100594792 A CN2011100594792 A CN 2011100594792A CN 201110059479 A CN201110059479 A CN 201110059479A CN 102134416 B CN102134416 B CN 102134416B
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- acrylate
- leveling agent
- fluorine
- flow agent
- water
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 11
- 239000011737 fluorine Substances 0.000 title abstract description 11
- 238000000576 coating method Methods 0.000 title abstract description 8
- 239000011248 coating agent Substances 0.000 title abstract description 7
- 239000003973 paint Substances 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- -1 Hexafluorobutyl Chemical group 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical group CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 claims description 3
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 3
- YJKHMSPWWGBKTN-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F YJKHMSPWWGBKTN-UHFFFAOYSA-N 0.000 claims description 3
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical compound CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical group CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002966 varnish Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 239000006115 industrial coating Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000675108 Citrus tangerina Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- AYEFIAVHMUFQPZ-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical class CC(O)CO.OC(=O)C=C AYEFIAVHMUFQPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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Abstract
The invention discloses a fluorine-containing acrylate leveling agent for an environment-friendly type water-soluble coating and a preparation method thereof. The acid value of the leveling agent is 30-60; the number-average molecular weight of the leveling agent is 3500-4500; the weight-average molecular weight of the leveling agent is 5000-10000; and the polydispersity of the leveling agent is 1.7-3.0. The invention aims at providing the fluorine-containing acrylate leveling agent for the environment-friendly type water-soluble coating, which can reduce the surface tension of a coating system, and has the advantages of high leveling speed, strong anti-shrinkage capacity and excellent long-wave leveling.
Description
Technical field
The present invention relates to a kind of water soluble paint fluorinated acrylate flow agent, belong to the coatings additive(s) technical field.
Background technology
Country's reply climate change planning is " 12 " important national ad hoc planning.The solvent-borne type industrial coating is subject to application limitations day by day because of its VOC discharging.And the non-silicon class flow agent that is used at present water-soluble industrial coating exists that surface tension is high, levelling speed slow, nonshrink hole ability and the shortcoming such as the long wave levelling is bad.
Summary of the invention
The object of the present invention is to provide and a kind ofly can reduce that coating system surface tension, levelling speed are fast, nonshrink hole ability strong and the excellent environmentally friendly water soluble paint fluorinated acrylate flow agent of long wave levelling.
Technical solution of the present invention is:
A kind of environmentally friendly water soluble paint fluorinated acrylate flow agent is characterized in that: the acid number of flow agent is 30～60, and surface tension 21-26 number-average molecular weight is 3500～4500, and weight-average molecular weight is 5000～10000, polymolecularity 1.7～3.0.
Described environmentally friendly water soluble paint fluorinated acrylate flow agent, made by the raw material of following weight percent:
Wherein said solvent is Virahol or methyl ether; Fluorinated acrylate monomer is vinylformic acid trifluoro ethyl ester, trifluoroethyl methacrylate, vinylformic acid hexafluoro butyl ester, Hexafluorobutyl mathacrylate, dodecafluorhe-ptylacrylate or dodecafluoroheptyl methacrylate; Acrylate monomer is methyl acrylate, ethyl propenoate, butyl acrylate or acrylic acid-2-ethyl ethyl ester; Initiator is Diisopropyl azodicarboxylate or benzoyl peroxide; The hydroxyl monomer is Propylene glycol monoacrylate, Hydroxyethyl acrylate, Rocryl 410, hydroxyethyl methylacrylate, vinylformic acid hydroxy butyl ester or methacrylic acid hydroxy butyl ester; Containing carboxylic monomer is acrylic or methacrylic acid.
Product work excellent performance of the present invention, production method is easy.
The invention will be further described below in conjunction with drawings and Examples.
Fig. 1 is water-soluble acrylic varnish, water-soluble acrylic ester flow agent and water-soluble fluorine-containing acrylate flow agent surface tension value comparison diagram of the present invention.
Fig. 2 is water-soluble acrylic ester flow agent and water-soluble fluorine-containing acrylate flow agent surface tension value comparison diagram in water-soluble acrylic varnish.
Embodiment
Embodiment 1:
In the four-hole boiling flask with reflux condensing tube, thermometer, agitator and dropping funnel, add 70 gram Virahols and start agitator and stir.When temperature rises to 70-85 ℃, after the equal solvent Virahol refluxes in prolong, begin to drip by 70 gram Virahols, 2.5 gram dodecafluoroheptyl methacrylates, 210 gram butyl acrylates, 27 gram vinylformic acid, 1.74 gram Diisopropyl azodicarboxylates, the mixture of 32 gram Propylene glycol monoacrylates, complete dropping after 2h, then maintain the temperature at 70-85 ℃ and continue to stir 2h; Mend to drip again the mixture 10 minutes of 40 gram Virahols and 0.19 gram Diisopropyl azodicarboxylate, then maintain the temperature at 70-85 ℃ and continue to stir 2h.Insulation transfers to 60 ± 2% with solid content after finishing, and takes out product, the sealed cans packing.
Product performance: outward appearance: little yellow transparent liquid; Admittedly contain: 60 ± 2%; Acid number: 45.76; Surface tension: 21-26; Number-average molecular weight: 3500-4500, weight-average molecular weight: 8000-9000, polymolecularity 1.8-1.9.
Surface tension is when 21-26, and flow agent can effectively reduce the coating system surface tension, paint has the characteristics such as levelling speed is fast, nonshrink hole ability is strong.Number-average molecular weight and weight-average molecular weight, polymolecularity are all in this is interval the time, and the long wave levelling property of paint is excellent.
Embodiment 2:
The consumption of each component is:
Wherein said solvent is Virahol or methyl ether; Fluorinated acrylate monomer is vinylformic acid trifluoro ethyl ester, trifluoroethyl methacrylate, vinylformic acid hexafluoro butyl ester, Hexafluorobutyl mathacrylate, dodecafluorhe-ptylacrylate or dodecafluoroheptyl methacrylate; Acrylate monomer is methyl acrylate, ethyl propenoate, butyl acrylate or acrylic acid-2-ethyl ethyl ester; Initiator is Diisopropyl azodicarboxylate or benzoyl peroxide; The hydroxyl monomer is Propylene glycol monoacrylate, Hydroxyethyl acrylate, Rocryl 410, hydroxyethyl methylacrylate, vinylformic acid hydroxy butyl ester or methacrylic acid hydroxy butyl ester; Containing carboxylic monomer is acrylic or methacrylic acid.
The substep usage ratio of above-mentioned same component is with embodiment 1.All the other are with embodiment 1.
The acid number of gained flow agent is 30～60, and surface tension 21-26 number-average molecular weight is 3500～4500, and weight-average molecular weight is 5000～10000, polymolecularity 1.7～3.0.
Surface tension is when 21-26, and flow agent can effectively reduce the coating system surface tension, paint has the characteristics such as levelling speed is fast, nonshrink hole ability is strong.Number-average molecular weight and weight-average molecular weight, polymolecularity are all in this is interval the time, and the long wave levelling property of paint is excellent.
Illustrate: 1, water soluble paint is with water-soluble fluorinated acrylate flow agent, and the surface tension value of water-soluble pure acrylate flow agent and water-soluble acrylic varnish stoste is seen Fig. 1.
If 2 add respectively water-soluble fluorine-containing acrylate flow agent and water-soluble pure acrylate flow agent 0.1%, 0.3%, 0.5%, 0.8% in water-soluble acrylic varnish, the surface tension downtrending figure of water-soluble acrylic varnish sees Fig. 2.
Above explanation during at 23.592 dyne, can well reduce the surface tension of water-soluble acrylic varnish when the surface tension value of water-soluble fluorine-containing acrylate flow agent.Again because the surface tension value of varnish has reduced, so this varnish has nonshrink hole ability, ground wettability and levelling speed preferably.
3, water-soluble pure acrylate flow agent and water-soluble fluorine-containing acrylate flow agent are added to respectively in paint, require in accordance with regulations to make the paint plate, test following data with tangerine peel instrument and glossometer:
Annotate: the water-soluble pure acrylate flow agent of 1#
2# water-soluble fluorine-containing acrylate flow agent
Between shortwave numerical value Wa0.1-0.3mm, between long wave numerical value We10-30mm, water-soluble fluorine-containing class acrylate flow agent is obviously lower than water-soluble pure acrylate flow agent numerical value, illustrates that water-soluble fluorine-containing class acrylate flow agent shortwave, long wave levelling property are excellent.
Claims (1)
1. environmentally friendly water soluble paint fluorinated acrylate flow agent, it is characterized in that: the raw material by following weight percent is made:
Wherein said solvent is Virahol or methyl ether; Fluorinated acrylate monomer is vinylformic acid trifluoro ethyl ester, trifluoroethyl methacrylate, vinylformic acid hexafluoro butyl ester, Hexafluorobutyl mathacrylate, dodecafluorhe-ptylacrylate or dodecafluoroheptyl methacrylate; Acrylate monomer is methyl acrylate, ethyl propenoate, butyl acrylate or acrylic acid-2-ethyl ethyl ester; Initiator is Diisopropyl azodicarboxylate or benzoyl peroxide; The hydroxyl monomer is Propylene glycol monoacrylate, Hydroxyethyl acrylate, Rocryl 410, hydroxyethyl methylacrylate, vinylformic acid hydroxy butyl ester or methacrylic acid hydroxy butyl ester; Containing carboxylic monomer is acrylic or methacrylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100594792A CN102134416B (en) | 2011-03-11 | 2011-03-11 | Fluorine-containing acrylate leveling agent for environment-friendly type water-soluble coating |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100594792A CN102134416B (en) | 2011-03-11 | 2011-03-11 | Fluorine-containing acrylate leveling agent for environment-friendly type water-soluble coating |
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| CN102134416A CN102134416A (en) | 2011-07-27 |
| CN102134416B true CN102134416B (en) | 2013-05-15 |
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| CN102617783B (en) * | 2012-04-10 | 2014-06-25 | 广东银洋树脂有限公司 | Preparation method and application of water-soluble fluorine-containing acrylic resin |
| CN102643565B (en) * | 2012-05-04 | 2013-04-10 | 浙江润禾有机硅新材料有限公司 | Terminal modified organic silicone coating flatting agent and preparation method thereof |
| CN102786626B (en) * | 2012-07-16 | 2016-03-02 | 六安科瑞达新型材料有限公司 | A kind of preparation method of polyacrylate(s) flow agent actives used for powder coating |
| CN102964513B (en) * | 2012-11-23 | 2014-08-20 | 陕西科技大学 | Preparation method of fluorine-containing water-based self-crosslinking acrylic resin emulsion |
| CN103601839B (en) * | 2013-11-14 | 2016-05-18 | 天恒达电工科技股份有限公司 | Acrylate copolymer levelling agent and preparation method thereof and the application process in wire enamel |
| CN105524208B (en) * | 2015-09-17 | 2017-11-21 | 韶关欧文化学工业有限公司 | A kind of preparation method of fluoro-acrylate copolymer levelling agent |
| CN109901361B (en) * | 2017-12-11 | 2022-12-16 | 固安鼎材科技有限公司 | Photosensitive resin composition |
| CN108707213B (en) * | 2018-05-18 | 2020-05-29 | 杭州师范大学 | Preparation method and application of hyperbranched block high-molecular copolymer |
| CN115260803A (en) * | 2022-08-02 | 2022-11-01 | 百草边大生物科技(青岛)有限公司 | Preparation method of plant modified antibacterial antiviral biological inorganic decorative coating |
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| JPH10158336A (en) * | 1996-12-02 | 1998-06-16 | Kyoeisha Chem Co Ltd | Acrylic copolymer and leveling agent for powder coating material containing the same copolymer as component |
| CN101225262B (en) * | 2008-01-30 | 2011-05-25 | 陈永康 | Fluorocarbon compound modified polyacrylate flow agent for coating ink and production method thereof |
| CN101284960B (en) * | 2008-05-20 | 2011-06-22 | 陈永康 | Loose colour floating dispersants for coating and printing ink and production method thereof |
| CN101591486A (en) * | 2009-06-12 | 2009-12-02 | 陈永康 | Anti-graffiti and fluorinated silicone modified acrylate flow agent of easy cleaning and production method |
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Denomination of invention: Fluorinated acrylic leveling agent for environmentally friendly water-soluble coatings Effective date of registration: 20231129 Granted publication date: 20130515 Pledgee: Agricultural Bank of China Limited Dongzhi County Branch Pledgor: ANHUI XOANONS CHEMICAL Co.,Ltd. Registration number: Y2023980068311 |