CN1294217C - 可溶型含氟涂料树脂及其制备方法 - Google Patents
可溶型含氟涂料树脂及其制备方法 Download PDFInfo
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- CN1294217C CN1294217C CNB2003101093838A CN200310109383A CN1294217C CN 1294217 C CN1294217 C CN 1294217C CN B2003101093838 A CNB2003101093838 A CN B2003101093838A CN 200310109383 A CN200310109383 A CN 200310109383A CN 1294217 C CN1294217 C CN 1294217C
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- vinyl ether
- vinyl
- ester
- alkyl
- vinyl ester
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- 229920005989 resin Polymers 0.000 title claims abstract description 61
- 239000011347 resin Substances 0.000 title claims abstract description 61
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 33
- 239000011737 fluorine Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000003973 paint Substances 0.000 title abstract description 13
- -1 alkyl vinyl ether Chemical compound 0.000 claims abstract description 52
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 41
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 229920001577 copolymer Polymers 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims description 50
- 239000011248 coating agent Substances 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 11
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 9
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims description 8
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical group CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 239000012188 paraffin wax Substances 0.000 claims description 6
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical group OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 claims description 4
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 4
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 4
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 claims description 4
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 4
- OJXVWULQHYTXRF-UHFFFAOYSA-N 3-ethenoxypropan-1-ol Chemical compound OCCCOC=C OJXVWULQHYTXRF-UHFFFAOYSA-N 0.000 claims description 3
- YQMANMTVEHKOHX-UHFFFAOYSA-N 4-ethenoxybutan-2-ol Chemical compound CC(O)CCOC=C YQMANMTVEHKOHX-UHFFFAOYSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- HJVKTYVDOZVQPA-UHFFFAOYSA-N ethenoxycyclopentane Chemical compound C=COC1CCCC1 HJVKTYVDOZVQPA-UHFFFAOYSA-N 0.000 claims description 3
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical group C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 claims description 3
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003999 initiator Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical group 0.000 description 4
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000001792 White test Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000002075 anti-alcohol Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Abstract
Description
烷基乙烯基醚 | 羟烷基乙烯基醚 | 链烷酸乙烯基酯 | 叔碳酸乙烯基酯 | |
实施例2 | 丁基乙烯基醚(38.0)环己基乙烯基醚(63.0) | 羟乙基乙烯基醚(108.0) | 戊酸乙烯基酯(45.0) | Veova-9(92.0) |
实施例3 | 环己基乙烯基醚(132.8) | 羟丁基乙烯基醚(169.7) | 丁酸乙烯基酯(92.5) | Veova-9(32) |
实施例4 | 异丙基乙烯基醚(234.5) | 羟丁基乙烯基醚(125.0) | 己酸乙烯基酯(50.0) | Veova-9(16.0) |
实施例5 | 乙基乙烯基醚(36.0)环己基乙烯基醚(63.0) | 羟丁基乙烯基醚(110.0) | 乙酸乙烯基酯(34.1) | Veova-9(140.0) |
实施例2 | 实施例3 | 实施例4 | 实施例5 | |
含氟量(摩尔%) | 34.85 | 36.01 | 33.15 | 34.29 |
羟基值(mgOH/g) | 93.9 | 98.3 | 88.9 | 73.8 |
粘度(30℃,THF) | 0.49 | 0.42 | 0.32 | 0.30 |
各链段的含量(摩尔%) | ||||
四氟乙烯 | 50.5 | 53.2 | 45.5 | 49.8 |
烷基乙烯基醚 | 14.9 | 14.0 | 34.7 | 16.16 |
羟烷基乙烯基醚 | 19.6 | 20.5 | 15.2 | 15.33 |
链烷酸乙烯基酯 | 5 | 9.2 | 3.6 | 3.8 |
叔碳酸乙烯基酯 | 10 | 3.1 | 1 | 14.9 |
附着力(划格法) | 0级 | 0级 | 0级 | 0级 |
硬度(铅笔硬度) | 3H | 3H | 3H | 3H |
冲击 | 50cm | 50cm | 50cm | 50cm |
弯曲试验 | 1mm无裂缝 | 1mm无裂缝 | 1mm无裂缝 | 1mm无裂缝 |
光泽(60°) | 84 | 87 | 87 | 85 |
耐酸(10%硫酸,常温) | 15天无变化 | 15天无变化 | 15天无变化 | 15天无变化 |
耐碱(10%NaOH,常温) | 15天无变化 | 15天无变化 | 15天无变化 | 15天无变化 |
耐甲苯(常温) | 15天无变化 | 15天无变化 | 15天无变化 | 15天无变化 |
耐丙酮擦拭 | >200次 | >200次 | >200次 | >200次 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2003101093838A CN1294217C (zh) | 2003-12-15 | 2003-12-15 | 可溶型含氟涂料树脂及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2003101093838A CN1294217C (zh) | 2003-12-15 | 2003-12-15 | 可溶型含氟涂料树脂及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN1629230A CN1629230A (zh) | 2005-06-22 |
CN1294217C true CN1294217C (zh) | 2007-01-10 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CNB2003101093838A Expired - Lifetime CN1294217C (zh) | 2003-12-15 | 2003-12-15 | 可溶型含氟涂料树脂及其制备方法 |
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CN (1) | CN1294217C (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101319113B (zh) * | 2008-07-18 | 2010-06-02 | 深圳市广田环保涂料有限公司 | 中温烘烤型氟碳漆及其使用方法 |
CN104829772B (zh) * | 2015-05-18 | 2016-09-14 | 山东森福新材料有限公司 | 一种常温固化含氟涂料树脂及其制备方法 |
JP6927216B2 (ja) * | 2016-07-14 | 2021-08-25 | Agc株式会社 | 含フッ素重合体組成物、フッ素樹脂塗料、塗装物品 |
CN110511628A (zh) * | 2019-08-26 | 2019-11-29 | 佛山科学技术学院 | 一种改性水性feve氟碳涂料及其制备方法 |
CN115011157A (zh) * | 2021-03-05 | 2022-09-06 | Agc株式会社 | 电池组外装涂布剂 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5064920A (en) * | 1989-11-17 | 1991-11-12 | Toagosei Chemical Industry Co., Ltd. | Fluorine-containing copolymer and coating composition containing the copolymer |
JPH06100834A (ja) * | 1992-09-16 | 1994-04-12 | Toagosei Chem Ind Co Ltd | 含フッ素樹脂塗料組成物 |
CN1117979A (zh) * | 1994-06-01 | 1996-03-06 | 埃勒夫阿托化学有限公司 | 羟基化的含氟共聚物和丙烯酸类共聚物的稳定水分散体及其制备方法和作为水性涂料的应用 |
CN1244556A (zh) * | 1999-08-20 | 2000-02-16 | 大连塑料研究所 | 以四氟乙烯为主的共聚物含氟涂料及其制法 |
-
2003
- 2003-12-15 CN CNB2003101093838A patent/CN1294217C/zh not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5064920A (en) * | 1989-11-17 | 1991-11-12 | Toagosei Chemical Industry Co., Ltd. | Fluorine-containing copolymer and coating composition containing the copolymer |
JPH06100834A (ja) * | 1992-09-16 | 1994-04-12 | Toagosei Chem Ind Co Ltd | 含フッ素樹脂塗料組成物 |
CN1117979A (zh) * | 1994-06-01 | 1996-03-06 | 埃勒夫阿托化学有限公司 | 羟基化的含氟共聚物和丙烯酸类共聚物的稳定水分散体及其制备方法和作为水性涂料的应用 |
CN1244556A (zh) * | 1999-08-20 | 2000-02-16 | 大连塑料研究所 | 以四氟乙烯为主的共聚物含氟涂料及其制法 |
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CP02 | Change in the address of a patent holder |
Address after: 200025 8th Floor, 560 Xujiahui Road, Huangpu District, Shanghai Patentee after: SHANGHAI 3F NEW MATERIAL TECHNOLOGY CO.,LTD. Address before: 200437 No. 99, Handan Road, Shanghai Patentee before: SHANGHAI 3F NEW MATERIAL TECHNOLOGY CO.,LTD. |
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CP02 | Change in the address of a patent holder | ||
CP03 | Change of name, title or address |
Address after: Room 801, 560 Xujiahui Road, Huangpu District, Shanghai 200025 Patentee after: Shanghai Huayi sanaifu New Material Co.,Ltd. Address before: 8 / F, 560 Xujiahui Road, Huangpu District, Shanghai 200025 Patentee before: SHANGHAI 3F NEW MATERIAL TECHNOLOGY Co.,Ltd. |
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CP03 | Change of name, title or address | ||
CX01 | Expiry of patent term |
Granted publication date: 20070110 |
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CX01 | Expiry of patent term |