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 (enExample) | 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 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009093568A1 (ja) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | フルオロアルキルアルコール不飽和カルボン酸誘導体混合物、これらの重合体およびこの重合体を有効成分とする撥水撥油剤 |
| WO2009093567A1 (ja) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | フルオロアルキルアルコール混合物およびその製造法 |
| WO2009151110A1 (ja) | 2008-06-13 | 2009-12-17 | ユニマテック株式会社 | ポリフルオロ-1-アルケンおよびその製造法 |
| EP2228356A1 (en) | 2006-03-10 | 2010-09-15 | Unimatec Co., Ltd. | Polyfluoroalkyl alcohol, or (meth)acrylic acid derivative thereof, and process for producing the same |
| WO2015064360A1 (ja) | 2013-11-01 | 2015-05-07 | ユニマテック株式会社 | 含フッ素重合体およびこれを有効成分とする表面改質剤 |
| WO2018084086A1 (ja) | 2016-11-01 | 2018-05-11 | ユニマテック株式会社 | 含フッ素重合体およびこれを有効成分とする防錆剤 |
| WO2021161593A1 (ja) | 2020-02-10 | 2021-08-19 | ユニマテック株式会社 | 含フッ素重合体を有効成分とする柔軟性撥水撥油剤 |
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 |
| CN101802028B (zh) | 2007-09-10 | 2012-08-29 | 优迈特株式会社 | 含氟聚合物及以其为有效成分的表面改性剂 |
| JP5257449B2 (ja) | 2008-06-13 | 2013-08-07 | ユニマテック株式会社 | ポリフルオロアルカジエン混合物およびその製造法 |
-
1982
- 1982-12-13 JP JP57218143A patent/JPS59108081A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2228356A1 (en) | 2006-03-10 | 2010-09-15 | Unimatec Co., Ltd. | Polyfluoroalkyl alcohol, or (meth)acrylic acid derivative thereof, and process for producing the same |
| WO2009093568A1 (ja) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | フルオロアルキルアルコール不飽和カルボン酸誘導体混合物、これらの重合体およびこの重合体を有効成分とする撥水撥油剤 |
| WO2009093567A1 (ja) | 2008-01-24 | 2009-07-30 | Unimatec Co., Ltd. | フルオロアルキルアルコール混合物およびその製造法 |
| WO2009151110A1 (ja) | 2008-06-13 | 2009-12-17 | ユニマテック株式会社 | ポリフルオロ-1-アルケンおよびその製造法 |
| WO2015064360A1 (ja) | 2013-11-01 | 2015-05-07 | ユニマテック株式会社 | 含フッ素重合体およびこれを有効成分とする表面改質剤 |
| WO2018084086A1 (ja) | 2016-11-01 | 2018-05-11 | ユニマテック株式会社 | 含フッ素重合体およびこれを有効成分とする防錆剤 |
| WO2021161593A1 (ja) | 2020-02-10 | 2021-08-19 | ユニマテック株式会社 | 含フッ素重合体を有効成分とする柔軟性撥水撥油剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59108081A (ja) | 1984-06-22 |
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