DE2539393C2 - Kohlenwasserstoff-lösliches, öl- und wasserabweisend machendes thermoplastisches Terpolymerisat und dieses Terpolymerisat enthaltende Kohlenwasserstofflösung - Google Patents
Kohlenwasserstoff-lösliches, öl- und wasserabweisend machendes thermoplastisches Terpolymerisat und dieses Terpolymerisat enthaltende KohlenwasserstofflösungInfo
- Publication number
- DE2539393C2 DE2539393C2 DE2539393A DE2539393A DE2539393C2 DE 2539393 C2 DE2539393 C2 DE 2539393C2 DE 2539393 A DE2539393 A DE 2539393A DE 2539393 A DE2539393 A DE 2539393A DE 2539393 C2 DE2539393 C2 DE 2539393C2
- Authority
- DE
- Germany
- Prior art keywords
- terpolymer
- hydrocarbon
- oil
- acrylate
- water
- 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
- 229920001897 terpolymer Polymers 0.000 title claims description 24
- 239000005871 repellent Substances 0.000 title claims description 6
- 229920001169 thermoplastic Polymers 0.000 title claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 5
- 229930195733 hydrocarbon Natural products 0.000 title description 14
- 150000002430 hydrocarbons Chemical class 0.000 title description 14
- 239000004215 Carbon black (E152) Substances 0.000 title description 12
- 239000000178 monomer Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- -1 fluorine-phosphate acrylate Chemical compound 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000005187 foaming Methods 0.000 description 10
- 229920000126 latex Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KBQPEQMZFVCZKQ-UHFFFAOYSA-N [F].OP(O)(O)=O Chemical group [F].OP(O)(O)=O KBQPEQMZFVCZKQ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 241001233037 catfish Species 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 102100025009 Ras-related GTP-binding protein C Human genes 0.000 description 1
- 101710094757 Ras-related GTP-binding protein C Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000012093 association test Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polymerisation Methods In General (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/502,749 US3950298A (en) | 1974-09-03 | 1974-09-03 | Fluoroaliphatic terpolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2539393A1 DE2539393A1 (de) | 1976-03-11 |
| DE2539393C2 true DE2539393C2 (de) | 1985-02-21 |
Family
ID=23999242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2539393A Expired DE2539393C2 (de) | 1974-09-03 | 1975-09-02 | Kohlenwasserstoff-lösliches, öl- und wasserabweisend machendes thermoplastisches Terpolymerisat und dieses Terpolymerisat enthaltende Kohlenwasserstofflösung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3950298A (enExample) |
| JP (1) | JPS5946248B2 (enExample) |
| CA (1) | CA1055647A (enExample) |
| DE (1) | DE2539393C2 (enExample) |
| FR (1) | FR2283912A1 (enExample) |
| GB (1) | GB1516117A (enExample) |
| NL (1) | NL181996C (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351880A (en) * | 1979-03-01 | 1982-09-28 | Daikin Kogyo Co., Ltd. | Prevention of adhesion of epoxy resins |
| US4386132A (en) * | 1980-03-27 | 1983-05-31 | Minnesota Mining And Manufacturing Company | Fly fishing line |
| US4751263A (en) * | 1981-07-01 | 1988-06-14 | Union Carbide Corporation | Curable molding compositions containing a poly(acrylate) |
| US4374889A (en) * | 1981-12-07 | 1983-02-22 | Minnesota Mining And Manufacturing Company | Oil-repellent microvoid-imaging material |
| US4426476A (en) | 1982-02-03 | 1984-01-17 | Minnesota Mining And Manufacturing Company | Textile treatments |
| US4518649A (en) * | 1984-05-11 | 1985-05-21 | Chicopee | Soil releasing textiles containing fluorochemical soil release agents and method for producing same |
| US4592930A (en) * | 1984-05-11 | 1986-06-03 | The Dow Chemical Company | Perfluorocarbon based polymeric coatings having low critical surface tensions |
| US4554325A (en) * | 1984-05-11 | 1985-11-19 | The Dow Chemical Company | Perfluorocarbon based polymeric coatings having low critical surface tensions |
| US4791167A (en) * | 1988-03-23 | 1988-12-13 | Hoechst Celanese Corporation | Autoxidizable fluorocarbon polymer compositions and methods |
| US4791166A (en) * | 1988-03-23 | 1988-12-13 | Hoechst Celanese Corporation | Fluorocarbon polymer compositions and methods |
| FR2649399B1 (fr) * | 1989-07-06 | 1991-10-18 | Norsolor Sa | Nouveaux copolymeres acryliques et leur application au revetement de materiaux bitumineux |
| US5194541A (en) * | 1989-07-06 | 1993-03-16 | Societe Anonyme Dite Norsolor | Acrylic copolymers and their application to the coating of bituminous materials |
| DE4143390A1 (en) * | 1991-04-26 | 1993-04-01 | Fluorine contg. (co)polymers, useful for water- and oil repellent treatment of substrates | |
| US5354598A (en) * | 1992-04-10 | 1994-10-11 | Minnesota Mining And Manufacturing Company | Article capable of displaying defined images |
| DE4319199A1 (de) * | 1993-06-09 | 1994-12-15 | Roehm Gmbh | Kratzfeste antisoiling- und antigraffity-Beschichtung für Formkörper |
| US5380644A (en) * | 1993-08-10 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Additive for the reduction of mottle in photothermographic and thermographic elements |
| US5612431A (en) * | 1994-09-21 | 1997-03-18 | Minnesota Mining And Manufacturing Company | Leaching of precious metal ore with fluoroaliphatic surfactant |
| US5532121A (en) * | 1995-03-24 | 1996-07-02 | Minnesota Mining And Manufacturing Company | Mottle reducing agent for photothermographic and thermographic elements |
| DE69810810T2 (de) * | 1997-10-21 | 2003-09-11 | Solutia Inc., St. Louis | Schaumarme kohlenwasserstoffölzusammensetzungen |
| US6150024A (en) * | 1997-11-25 | 2000-11-21 | Rexam Release, Inc. | Acrylate release compositions and sheet materials having a release coating formed of the same |
| US7585919B2 (en) * | 2006-09-26 | 2009-09-08 | 3M Innovative Properties Company | Polymer derived from monomers with long-chain aliphatic, poly(oxyalkylene) and substrate-reactive groups |
| CA2686481A1 (en) * | 2007-05-22 | 2008-11-27 | Asahi Glass Company, Limited | Antifouling composition, method for its production and article treated therewith |
| WO2010036465A1 (en) * | 2008-09-26 | 2010-04-01 | 3M Innovative Properties Company | Antimicrobial and antifouling polymeric materials |
| US9290596B2 (en) * | 2010-05-27 | 2016-03-22 | The Chemours Company Fc, Llc | Solvent-based fluoropolymer additives and their use in coating compositions |
| US9029452B2 (en) * | 2010-05-27 | 2015-05-12 | E I Du Pont De Nemours And Company | Fluoropolymer additive for coatings |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2991277A (en) * | 1955-06-10 | 1961-07-04 | Air Reduction | Copolymers of trifluoroethyl vinyl ether and alkyl esters of acrylic of methacrylic acid, and method for preparing same |
| US3256230A (en) * | 1961-05-03 | 1966-06-14 | Du Pont | Polymeric water and oil repellents |
| US3329661A (en) * | 1964-12-01 | 1967-07-04 | Minnesota Mining & Mfg | Compositions and treated articles thereof |
| US3341497A (en) * | 1966-01-21 | 1967-09-12 | Minnesota Mining & Mfg | Organic solvent soluble perfluorocarbon copolymers |
| US3654244A (en) * | 1970-03-16 | 1972-04-04 | Us Agriculture | Polymers for soil-release textile finishes |
| US3625929A (en) * | 1970-07-06 | 1971-12-07 | Calgon Corp | Polyfluoroalkenylalkoxy acrylates and polymers thereof |
-
1974
- 1974-09-03 US US05/502,749 patent/US3950298A/en not_active Expired - Lifetime
-
1975
- 1975-08-25 CA CA234,069A patent/CA1055647A/en not_active Expired
- 1975-09-02 FR FR7526900A patent/FR2283912A1/fr active Granted
- 1975-09-02 GB GB36159/75A patent/GB1516117A/en not_active Expired
- 1975-09-02 JP JP50105670A patent/JPS5946248B2/ja not_active Expired
- 1975-09-02 DE DE2539393A patent/DE2539393C2/de not_active Expired
- 1975-09-03 NL NLAANVRAGE7510392,A patent/NL181996C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US3950298A (en) | 1976-04-13 |
| JPS5150993A (enExample) | 1976-05-06 |
| CA1055647A (en) | 1979-05-29 |
| JPS5946248B2 (ja) | 1984-11-12 |
| FR2283912B1 (enExample) | 1980-07-18 |
| NL7510392A (nl) | 1976-03-05 |
| FR2283912A1 (fr) | 1976-04-02 |
| GB1516117A (en) | 1978-06-28 |
| NL181996B (nl) | 1987-07-16 |
| NL181996C (nl) | 1987-12-16 |
| DE2539393A1 (de) | 1976-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2539393C2 (de) | Kohlenwasserstoff-lösliches, öl- und wasserabweisend machendes thermoplastisches Terpolymerisat und dieses Terpolymerisat enthaltende Kohlenwasserstofflösung | |
| DE2531119C2 (enExample) | ||
| DE4201604A1 (de) | Fluorhaltige copolymerisate und daraus hergestellte waessrige dispersionen | |
| DE3856225T2 (de) | Wasser und Öl abweisende Verbindung mit reinigenden Eigenschaften | |
| DE69612796T2 (de) | Wasser- und ölabweisende Zusammensetzung, Behandlungsverfahren und Copolymer | |
| DE4201603A1 (de) | Mischungen fluorhaltiger copolymerisate | |
| DE1248945B (de) | Verfahren zur Herstellung von fluorhaltigen Blockmischpolymerisaten | |
| DE69531993T2 (de) | Hydrophobierende und ölphobierende schmutzabweisungsmittel | |
| DE1745163B2 (de) | Impraegniermittel zum schmutz- und oelabweisenden impraegnieren von textilien | |
| DE2025696B2 (de) | Verfahren zur Herstellung einer stabilen Latex-Dispersion | |
| CH643280A5 (de) | Wasser- und oelabstossendes mittel fuer textilien mit hoher bestaendigkeit gegen waschen und trockenreinigen. | |
| DE2749386A1 (de) | Dispersionen hydrophiler acrylharze | |
| DE1444114A1 (de) | Latex zum Wasser- und OElabstossendmachen von Fasermaterial | |
| WO2000078865A1 (de) | Bimodale poly(meth)acrylatplastisole und verfahren zu ihrer herstellung | |
| DE2609462C3 (de) | Perfluoralkyläthylacrylat-Copolymere | |
| DE2134978C3 (de) | Wasser- und ölabstoßend machende Zusammensetzungen | |
| DE3787048T2 (de) | Oberflächenmodifiziermittel. | |
| DE1469462A1 (de) | Impraegniermittel | |
| DE2248774A1 (de) | Fluorierte verbindungen mit wasserabweisenden und oelabweisenden eigenschaften | |
| DE2633870C3 (de) | Verwendung von organischen Lösungen oder wäßrigen Dispersionen oleophober und hydrophober Pfropfpollymerer zum Oleophieren ud Hydrophobieren von Substraten | |
| DE3800845A1 (de) | Pfropfcopolymerisate, ein verfahren zu deren herstellung und deren verwendung | |
| DE2140261A1 (de) | Derivate langkettiger fluoralkohole | |
| DE2151035A1 (de) | Polymere mit laengerkettigen fluoralkylseitenketten tragenden acrylestermonomereinheiten | |
| DE1926541A1 (de) | Verfahren zur Herstellung von Perfluoralkylamidoalkyl-und -alkylthioester der Fumarsaeure und anderer aethylenisch ungesaettigter polybasischer Saeuren sowie deren Polymerisate | |
| DE4113893A1 (de) | Waessrige dispersionen mit perfluoralkylgruppen enthaltenden copolymerisaten, verfahren zu ihrer herstellung und ihre verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |