CN104974019B - 一种烯丙基醚类含氟单体及其合成方法和应用 - Google Patents
一种烯丙基醚类含氟单体及其合成方法和应用 Download PDFInfo
- Publication number
- CN104974019B CN104974019B CN201510318763.5A CN201510318763A CN104974019B CN 104974019 B CN104974019 B CN 104974019B CN 201510318763 A CN201510318763 A CN 201510318763A CN 104974019 B CN104974019 B CN 104974019B
- Authority
- CN
- China
- Prior art keywords
- allyl ether
- fluorochemical monomer
- allyl
- phenyl
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 22
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 claims abstract description 22
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000013638 trimer Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 150000007530 organic bases Chemical class 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000000675 fabric finishing Substances 0.000 claims abstract description 7
- 238000009962 finishing (textile) Methods 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 238000009988 textile finishing Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- -1 n-dodecyl Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
- D06M15/353—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510318763.5A CN104974019B (zh) | 2015-06-11 | 2015-06-11 | 一种烯丙基醚类含氟单体及其合成方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510318763.5A CN104974019B (zh) | 2015-06-11 | 2015-06-11 | 一种烯丙基醚类含氟单体及其合成方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104974019A CN104974019A (zh) | 2015-10-14 |
CN104974019B true CN104974019B (zh) | 2016-08-24 |
Family
ID=54271040
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510318763.5A Active CN104974019B (zh) | 2015-06-11 | 2015-06-11 | 一种烯丙基醚类含氟单体及其合成方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104974019B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117486686A (zh) * | 2023-10-30 | 2024-02-02 | 台州氟乐新材料合伙企业(有限合伙) | 六氟丙烯三聚体绿色化学转化制备全氟醚类化合物的方法 |
CN117486687A (zh) * | 2023-10-30 | 2024-02-02 | 台州氟乐新材料合伙企业(有限合伙) | 一种环保的全氟壬烯基醚的制备方法 |
CN117486685A (zh) * | 2023-10-30 | 2024-02-02 | 台州氟乐新材料合伙企业(有限合伙) | 一种高效全氟壬烯基醚的制备方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3522084A (en) * | 1965-02-18 | 1970-07-28 | Us Agriculture | Process for treating fibrous materials with a fluorinated allyl ether |
JPS6051146A (ja) * | 1983-08-30 | 1985-03-22 | Neos Co Ltd | 含フツ素芳香族ジカルボン酸類の製造法 |
JPH05339190A (ja) * | 1992-06-12 | 1993-12-21 | Nitto Denko Corp | 含フツ素フエノ―ルとその製造法 |
US6291704B1 (en) * | 1998-01-20 | 2001-09-18 | Alliedsignal Inc. | Polymerizable halogenated vinyl ethers |
CN101033205A (zh) * | 2006-12-21 | 2007-09-12 | 巨化集团技术中心 | 一种全氟壬(烯)氧基苯磺酸钠的合成方法 |
CN101016376B (zh) * | 2007-01-23 | 2010-10-06 | 浙江工业大学 | 一种聚乙二醇全氟烯基甲基醚的合成方法 |
CN100500737C (zh) * | 2007-01-23 | 2009-06-17 | 浙江工业大学 | 一种聚乙二醇全氟烯基单醚的合成方法 |
JP5546184B2 (ja) * | 2009-09-08 | 2014-07-09 | 株式会社ネオス | 含フッ素ノニオン系界面活性剤 |
WO2011129015A1 (ja) * | 2010-04-16 | 2011-10-20 | 株式会社ネオス | 防汚性付与剤 |
CN102070740B (zh) * | 2010-11-16 | 2012-10-03 | 巨化集团公司 | 一种含氟微乳液的制备方法 |
CN102210995B (zh) * | 2011-04-06 | 2014-01-29 | 浙江工业大学 | 一种聚甘油全氟烯基醚混合物及其制备方法 |
CN103432959B (zh) * | 2013-09-18 | 2015-01-14 | 华中师范大学 | 含六氟丙烯三聚体基的表面活性剂及其制备方法 |
-
2015
- 2015-06-11 CN CN201510318763.5A patent/CN104974019B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN104974019A (zh) | 2015-10-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104974019B (zh) | 一种烯丙基醚类含氟单体及其合成方法和应用 | |
CN101573315B (zh) | 长链聚亚甲基卤调聚物 | |
Chinta et al. | The sex pheromone of the wasp spider Argiope bruennichi | |
JP5032492B2 (ja) | フッ素化ジェミニ界面活性剤 | |
WO2005092997A1 (ja) | 表面処理剤と、含フッ素単量体および含フッ素重合体 | |
EP1976820B1 (en) | Fluorous telomeric compounds and polymers containing same | |
US3457247A (en) | Fluorocarbon compounds and polymers thereof | |
CN104583254B (zh) | 含氟共聚物及其制造方法、拒水剂组合物、物品 | |
CN105330867B (zh) | 一种有机氟硅表面处理剂及其制备方法 | |
CN106674416B (zh) | 一种含氟丙烯酸酯共聚乳液及其合成方法、应用 | |
CN106459103B (zh) | 含氟硅烷化合物 | |
US20130030130A1 (en) | Method for producing block polymer, block polymers, and surface treatment agent | |
CN109082280A (zh) | 一种液晶材料的制备方法 | |
JP2011526905A (ja) | フッ素化エステル | |
CN105859950A (zh) | 一种核壳型含氟含硅长碳链丙烯酸酯拒水拒油剂 | |
CN105983371A (zh) | 一种含氟羧酸甜菜碱型表面活性剂及其制备方法 | |
CN105037149B (zh) | 一种甲基丙烯酸酯类含氟单体及其合成方法和应用 | |
CN105247005B (zh) | 拒水拒油剂组合物、拒水拒油剂组合物的制造方法及物品 | |
US20120255651A1 (en) | Fluoroalkylalkoxylates | |
CN109468840A (zh) | 一种持久型织物防水剂及其制备方法 | |
CN105924573B (zh) | 一种全氟烷基聚烯酸酯防水剂、制备方法及应用 | |
CN101433813B (zh) | 一种全氟丙烯基季铵盐阳离子表面活性剂、合成方法和用途 | |
CN105061668A (zh) | 一种阳离子型含氟乳液及其制备方法 | |
AU2010242860A1 (en) | Alkoxylation of fluorinated alcohols | |
US20120259143A1 (en) | Fluoroalkylalkoxylates |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP02 | Change in the address of a patent holder | ||
CP02 | Change in the address of a patent holder |
Address after: No. 999, Changhong East Street, Deqing County, Huzhou City, Zhejiang Province Moganshan campus, Zhejiang University of Technology Patentee after: Zhejiang University of Technology Address before: 310014, Zhejiang City, No. 18 Chao Wang Road, Zhejiang University of Technology Patentee before: Zhejiang University of Technology |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20201113 Address after: 11th floor, donglecheng international, Shuguang Road, Chengguan Street, Dongming County, Heze City, Shandong Province Patentee after: Heze Jianshu Intelligent Technology Co., Ltd Address before: No. 999, Changhong East Street, Deqing County, Huzhou City, Zhejiang Province Moganshan campus, Zhejiang University of Technology Patentee before: ZHEJIANG University OF TECHNOLOGY |