JPS59108081A - 撥水撥油剤 - Google Patents
撥水撥油剤Info
- Publication number
- JPS59108081A JPS59108081A JP57218143A JP21814382A JPS59108081A JP S59108081 A JPS59108081 A JP S59108081A JP 57218143 A JP57218143 A JP 57218143A JP 21814382 A JP21814382 A JP 21814382A JP S59108081 A JPS59108081 A JP S59108081A
- Authority
- JP
- Japan
- Prior art keywords
- water
- group
- oil repellent
- 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.)
- Granted
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 230000002940 repellent Effects 0.000 title claims abstract description 17
- 239000005871 repellent Substances 0.000 title claims abstract description 17
- 229920001577 copolymer Polymers 0.000 claims abstract description 36
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 26
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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
- 125000001033 ether group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 abstract description 7
- 238000005108 dry cleaning Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 5
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical compound OC(=O)OC=C FXPHJTKVWZVEGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- 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 14
- 239000007787 solid Substances 0.000 description 14
- 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 8
- 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 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 229950011008 tetrachloroethylene Drugs 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- -1 2-chloroethyl vinyl Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 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 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UCRSPYLHWASUKR-UHFFFAOYSA-N ethenyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OC=C UCRSPYLHWASUKR-UHFFFAOYSA-N 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
- 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 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
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 235000020094 liqueur Nutrition 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002954 polymerization reaction product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011435 rock Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method 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 true JPS59108081A (ja) | 1984-06-22 |
| JPS6322237B2 JPS6322237B2 (OSRAM) | 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 (OSRAM) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62577A (ja) * | 1985-03-18 | 1987-01-06 | Daikin Ind Ltd | 撥水撥油剤 |
| 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 |
| US7566801B2 (en) | 2006-03-10 | 2009-07-28 | Unimatec Co., Ltd | Polyfluoroalkyl alcohol, or (METH)acrylic acid derivative thereof, and process for producing the same |
| US7956225B2 (en) | 2008-06-13 | 2011-06-07 | Unimatec Co., Ltd. | Polyfluoro-1-alkene and method for producing the same |
| US8163857B2 (en) | 2008-06-13 | 2012-04-24 | Unimatec Co., Ltd. | Polyfluoroalkadiene mixture and method for producing the same |
| US8278361B2 (en) | 2008-01-24 | 2012-10-02 | Unimatec Co., Ltd. | Fluoroalkyl alcohol mixture and method for producing the same |
| US8501888B2 (en) | 2007-09-10 | 2013-08-06 | Unimatec Co., Ltd. | Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient |
Families Citing this family (4)
| 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 |
| US20160251468A1 (en) | 2013-11-01 | 2016-09-01 | Unimatec Co., Ltd. | Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient |
| JP6693571B2 (ja) | 2016-11-01 | 2020-05-13 | 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 |
| JP7269430B2 (ja) | 2020-02-10 | 2023-05-08 | 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 |
-
1982
- 1982-12-13 JP JP57218143A patent/JPS59108081A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62577A (ja) * | 1985-03-18 | 1987-01-06 | Daikin Ind Ltd | 撥水撥油剤 |
| 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 |
| US7566801B2 (en) | 2006-03-10 | 2009-07-28 | Unimatec Co., Ltd | Polyfluoroalkyl alcohol, or (METH)acrylic acid derivative thereof, and process for producing the same |
| US8501888B2 (en) | 2007-09-10 | 2013-08-06 | Unimatec Co., Ltd. | Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient |
| US8278361B2 (en) | 2008-01-24 | 2012-10-02 | Unimatec Co., Ltd. | Fluoroalkyl alcohol mixture and method for producing the same |
| US7956225B2 (en) | 2008-06-13 | 2011-06-07 | Unimatec Co., Ltd. | Polyfluoro-1-alkene and method for producing the same |
| US8163857B2 (en) | 2008-06-13 | 2012-04-24 | Unimatec Co., Ltd. | Polyfluoroalkadiene mixture and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6322237B2 (OSRAM) | 1988-05-11 |
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