JPS6322237B2 - - Google Patents
Info
- Publication number
- JPS6322237B2 JPS6322237B2 JP57218143A JP21814382A JPS6322237B2 JP S6322237 B2 JPS6322237 B2 JP S6322237B2 JP 57218143 A JP57218143 A JP 57218143A JP 21814382 A JP21814382 A JP 21814382A JP S6322237 B2 JPS6322237 B2 JP S6322237B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- water
- carbon atoms
- copolymer
- perfluoroalkyl group
- 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.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 15
- 239000005871 repellent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 230000002940 repellent Effects 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 5
- XZUFJUJMSCHNDB-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoropropane-1,2-diol Chemical group OC(F)(F)C(O)(F)C(F)(F)F XZUFJUJMSCHNDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- QUKRIOLKOHUUBM-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C QUKRIOLKOHUUBM-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229950011008 tetrachloroethylene Drugs 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005108 dry cleaning Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- ZLHVSEPPILCZHH-UHFFFAOYSA-N ethenyl 4-tert-butylbenzoate Chemical compound CC(C)(C)C1=CC=C(C(=O)OC=C)C=C1 ZLHVSEPPILCZHH-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- -1 vinyl 3,5-dimethylbenzoate Chemical compound 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical class CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229940022682 acetone Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WUIOPDYOMAXHRZ-UHFFFAOYSA-N ethenyl 4-chlorobenzoate Chemical compound ClC1=CC=C(C(=O)OC=C)C=C1 WUIOPDYOMAXHRZ-UHFFFAOYSA-N 0.000 description 1
- BGVWGPMAGMJLBU-UHFFFAOYSA-N ethenyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC=C)=CC=CC2=C1 BGVWGPMAGMJLBU-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002954 polymerization reaction product Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57218143A JPS59108081A (ja) | 1982-12-13 | 1982-12-13 | 撥水撥油剤 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57218143A JPS59108081A (ja) | 1982-12-13 | 1982-12-13 | 撥水撥油剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59108081A JPS59108081A (ja) | 1984-06-22 |
JPS6322237B2 true JPS6322237B2 (fr) | 1988-05-11 |
Family
ID=16715311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57218143A Granted JPS59108081A (ja) | 1982-12-13 | 1982-12-13 | 撥水撥油剤 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59108081A (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009093567A1 (fr) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | Mélange d'alcools fluoroalkyliques et procédé permettant de le produire |
WO2009093568A1 (fr) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | Mélange de dérivés d'alcool fluoroalkylique-acide carboxylique insaturé, polymère des dérivés et agent hydrofuge et oléofuge contenant le polymère comme ingrédient actif |
WO2009151110A1 (fr) | 2008-06-13 | 2009-12-17 | ユニマテック株式会社 | Polyfluoro-1-alcane et son procédé de fabrication |
EP2228356A1 (fr) | 2006-03-10 | 2010-09-15 | Unimatec Co., Ltd. | Alcool polyfluoroalkylique ou son dérivé de l'acide (méth)acrylique et son procédé de production |
WO2015064360A1 (fr) | 2013-11-01 | 2015-05-07 | ユニマテック株式会社 | Polymère fluoré, et agent de modification de surface le contenant comme matière active |
WO2018084086A1 (fr) | 2016-11-01 | 2018-05-11 | ユニマテック株式会社 | Fluoropolymère et produit antirouille le contenant en tant que matière active |
WO2021161593A1 (fr) | 2020-02-10 | 2021-08-19 | ユニマテック株式会社 | Hydrofuge et oléofuge doux comprenant un polymère contenant du fluor en tant que principe actif |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4728707A (en) * | 1985-03-18 | 1988-03-01 | Daikin Industries Ltd. | Water- and oil-repellent |
JPH05194322A (ja) * | 1992-01-17 | 1993-08-03 | Shin Etsu Chem Co Ltd | 含フッ素アクリル酸エステル |
WO2009034773A1 (fr) | 2007-09-10 | 2009-03-19 | Unimatec Co., Ltd. | Polymère contenant du fluor et modificateur de surface le contenant en tant qu'ingrédient actif |
US8163857B2 (en) | 2008-06-13 | 2012-04-24 | Unimatec Co., Ltd. | Polyfluoroalkadiene mixture and method for producing the same |
-
1982
- 1982-12-13 JP JP57218143A patent/JPS59108081A/ja active Granted
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2228356A1 (fr) | 2006-03-10 | 2010-09-15 | Unimatec Co., Ltd. | Alcool polyfluoroalkylique ou son dérivé de l'acide (méth)acrylique et son procédé de production |
WO2009093567A1 (fr) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | Mélange d'alcools fluoroalkyliques et procédé permettant de le produire |
WO2009093568A1 (fr) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | Mélange de dérivés d'alcool fluoroalkylique-acide carboxylique insaturé, polymère des dérivés et agent hydrofuge et oléofuge contenant le polymère comme ingrédient actif |
WO2009151110A1 (fr) | 2008-06-13 | 2009-12-17 | ユニマテック株式会社 | Polyfluoro-1-alcane et son procédé de fabrication |
WO2015064360A1 (fr) | 2013-11-01 | 2015-05-07 | ユニマテック株式会社 | Polymère fluoré, et agent de modification de surface le contenant comme matière active |
WO2018084086A1 (fr) | 2016-11-01 | 2018-05-11 | ユニマテック株式会社 | Fluoropolymère et produit antirouille le contenant en tant que matière active |
WO2021161593A1 (fr) | 2020-02-10 | 2021-08-19 | ユニマテック株式会社 | Hydrofuge et oléofuge doux comprenant un polymère contenant du fluor en tant que principe actif |
Also Published As
Publication number | Publication date |
---|---|
JPS59108081A (ja) | 1984-06-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1326902B1 (fr) | Polyacrylates fluores degradables amorphes | |
JPS6322237B2 (fr) | ||
JP2004352976A (ja) | 含フッ素重合体を含んでなる表面処理剤 | |
EP0408917A1 (fr) | Copolymère, contenant un ester acrylique ou méthacrylique disposant d'un groupe fluoroalkyle | |
JPH0830100B2 (ja) | 含フツ素共重合体 | |
JPH0157709B2 (fr) | ||
JP3876495B2 (ja) | 撥水撥油剤およびその製造法 | |
JP2003520280A (ja) | 基材に忌避特性を与えるのに有用なフルオロケミカル共重合体およびフルオロケミカル共重合体組成物 | |
JP2770387B2 (ja) | 防汚加工剤 | |
JP2926770B2 (ja) | 新規共重合体 | |
JPH0713118B2 (ja) | 新規共重合体及び撥水撥油剤 | |
JPS5859277A (ja) | 撥水撥油剤 | |
WO2003062347A1 (fr) | Dispersion aqueuse impermeabilisante eau et huile | |
JP2769834B2 (ja) | 撥水撥油防汚加工剤 | |
JPS6342954B2 (fr) | ||
JP3241431B2 (ja) | 溶剤型撥水撥油剤組成物および撥水撥油加工方法 | |
JPH0525914B2 (fr) | ||
KR830007773A (ko) | 고니트릴 공중합체 라텍스 피복물을 위한 유착제의 제조방법 | |
JPH0730307B2 (ja) | 撥水撥油剤 | |
JPS6247466B2 (fr) | ||
JP2503612B2 (ja) | 撥水撥油剤組成物 | |
KR830000046B1 (ko) | 방수 및 방유제의 조성물 | |
JPS6358816B2 (fr) | ||
JPH0465113B2 (fr) | ||
JP5229005B2 (ja) | 含フッ素重合体を含んでなる表面処理剤 |