DE2531119C2 - - Google Patents
Info
- Publication number
- DE2531119C2 DE2531119C2 DE2531119A DE2531119A DE2531119C2 DE 2531119 C2 DE2531119 C2 DE 2531119C2 DE 2531119 A DE2531119 A DE 2531119A DE 2531119 A DE2531119 A DE 2531119A DE 2531119 C2 DE2531119 C2 DE 2531119C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylate
- methacrylate
- polyoxyethylene
- tetracopolymer
- weight
- 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
- -1 alkyl methacrylate Chemical compound 0.000 claims description 31
- 229920000950 tetracopolymer Polymers 0.000 claims description 30
- 239000004744 fabric Substances 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000010186 staining Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 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
- 229920000728 polyester Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 210000002268 wool Anatomy 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
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- RTJZWOGSCLVJLD-UHFFFAOYSA-N 2-[1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl(methyl)amino]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RTJZWOGSCLVJLD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KDQOWJBEWQXPDA-UHFFFAOYSA-M [Cl-].FC([N+](C(F)(F)F)(C(F)(F)F)C(C(C(NS(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F Chemical compound [Cl-].FC([N+](C(F)(F)F)(C(F)(F)F)C(C(C(NS(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F KDQOWJBEWQXPDA-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 235000012045 salad Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
- Y10T442/2287—Fluorocarbon containing
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/487,606 US3944527A (en) | 1974-07-11 | 1974-07-11 | Fluoroaliphatic copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2531119A1 DE2531119A1 (de) | 1976-01-29 |
| DE2531119C2 true DE2531119C2 (en, 2012) | 1988-09-22 |
Family
ID=23936428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752531119 Granted DE2531119A1 (de) | 1974-07-11 | 1975-07-10 | Fluoraliphatische copolymere |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3944527A (en, 2012) |
| JP (1) | JPS6025549B2 (en, 2012) |
| BE (1) | BE831217A (en, 2012) |
| CA (1) | CA1064641A (en, 2012) |
| DE (1) | DE2531119A1 (en, 2012) |
| FR (1) | FR2277840A1 (en, 2012) |
| GB (1) | GB1511572A (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS608068B2 (ja) * | 1978-09-28 | 1985-02-28 | ダイキン工業株式会社 | 撥水撥油剤 |
| JPS5815146B2 (ja) * | 1978-10-14 | 1983-03-24 | ダイキン工業株式会社 | 泡消火剤用添加剤 |
| US4401780A (en) * | 1982-02-03 | 1983-08-30 | Minnesota Mining And Manufacturing Company | Textile treatments |
| US4426476A (en) | 1982-02-03 | 1984-01-17 | Minnesota Mining And Manufacturing Company | Textile treatments |
| US4482608A (en) * | 1982-07-26 | 1984-11-13 | Minnesota Mining And Manufacturing Company | Release coating for infrared imageable and thermally imageable films |
| JPS5932471A (ja) * | 1982-08-16 | 1984-02-21 | ダイキン工業株式会社 | 消火用水性組成物 |
| US4518649A (en) * | 1984-05-11 | 1985-05-21 | Chicopee | Soil releasing textiles containing fluorochemical soil release agents and method for producing same |
| US4624889A (en) * | 1984-08-17 | 1986-11-25 | Minnesota Mining And Manufacturing Company | Launderable textile sizing having stain resistance and soil release |
| FR2579211B1 (fr) * | 1985-03-20 | 1987-09-18 | Atochem | Copolymeres fluores et leur application au traitement hydrophobe et oleophobe de substrats divers |
| JPS62158730A (ja) * | 1985-12-30 | 1987-07-14 | Sekisui Plastics Co Ltd | 発泡性熱可塑性樹脂粒子 |
| JPH083630B2 (ja) * | 1986-01-23 | 1996-01-17 | 富士写真フイルム株式会社 | 感光性組成物 |
| JPH0762761B2 (ja) * | 1986-03-28 | 1995-07-05 | 富士写真フイルム株式会社 | 画像形成材料 |
| US4791167A (en) * | 1988-03-23 | 1988-12-13 | Hoechst Celanese Corporation | Autoxidizable fluorocarbon polymer compositions and methods |
| GB9122328D0 (en) * | 1991-10-22 | 1991-12-04 | British Petroleum Co Plc | Novel esters |
| DE69207779T2 (de) | 1991-11-12 | 1996-05-30 | Minnesota Mining & Mfg | Derivate fluoroaliphatischer dimer-säuren und deren verwendung |
| DE4244951C2 (de) * | 1992-12-01 | 1998-08-06 | Minnesota Mining & Mfg | Fasersubstrat mit Wasser-, Öl-, Schmutzabweisungsvermögen und Weichgriffigkeit |
| US5492599A (en) * | 1994-05-18 | 1996-02-20 | Minnesota Mining And Manufacturing Company | Treated substrate having improved release properties |
| US5716685A (en) * | 1996-10-23 | 1998-02-10 | Minnesota Mining And Manufacturing Company | Silicone-containing copolymer and bleed through resistant, ink receptive, and adhesive receptive coatings and coated substrates prepared therefrom |
| US5874144A (en) * | 1996-10-23 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Silicon-free copolymer and bleed-through resistant, ink receptive, and adhesive receptive coatings and coated substrates prepared therefrom |
| JPH11279527A (ja) * | 1997-06-30 | 1999-10-12 | Asahi Glass Co Ltd | 防汚加工剤組成物、その製造方法およびそれを用いた被処理物 |
| US6878440B1 (en) | 1999-07-02 | 2005-04-12 | 3M Innovative Properties Company | Pressure sensitive adhesive sheet and production method thereof |
| US6451717B1 (en) | 1999-12-14 | 2002-09-17 | E. I. Du Pont De Nemours And Company | Highly durable oil/water repellents for textiles |
| US20040091713A1 (en) * | 2000-06-09 | 2004-05-13 | Toshihiro Suwa | Adherable fluorine-containing material sheet, adhesive fluorine-containing material sheet, and adhering method and adhesion structure of fluorine-containing material sheet |
| US6482911B1 (en) | 2001-05-08 | 2002-11-19 | 3M Innovative Properties Company | Fluoroalkyl polymers containing a cationogenic segment |
| US6479605B1 (en) | 2001-05-15 | 2002-11-12 | E. I. Du Pont De Nemours And Company | High-durability, low-yellowing repellent for textiles |
| JP4083399B2 (ja) * | 2001-07-24 | 2008-04-30 | セントラル硝子株式会社 | 含フッ素重合性単量体およびそれを用いた高分子化合物 |
| US7063895B2 (en) * | 2001-08-01 | 2006-06-20 | National Starch And Chemical Investment Holding Corporation | Hydrophobically modified solution polymers and their use in surface protecting formulations |
| US6903173B2 (en) * | 2002-08-02 | 2005-06-07 | 3M Innovative Properties Co. | Fluorinated polymers |
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| CN101679834B (zh) * | 2007-05-22 | 2013-11-27 | 旭硝子株式会社 | 防污加工剂组合物及其制造方法及加工物品 |
| CN101679569A (zh) * | 2007-06-06 | 2010-03-24 | 3M创新有限公司 | 氟化醚组合物以及使用该组合物的方法 |
| WO2009076389A1 (en) * | 2007-12-12 | 2009-06-18 | 3M Innovative Properties Company | Hardcoats comprising perfluoropolyether polymers with poly(alkylene oxide) repeat units |
| WO2010080288A2 (en) * | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Coating composition |
| WO2010080473A1 (en) * | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| CN104968760B (zh) | 2012-11-19 | 2019-02-05 | 3M创新有限公司 | 使含烃地层与氟化离子聚合物接触的方法 |
| CN105263973B (zh) | 2012-11-19 | 2019-06-14 | 3M创新有限公司 | 包含氟化聚合物和非氟化聚合物的组合物及其制备和使用方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282905A (en) * | 1961-05-03 | 1966-11-01 | Du Pont | Fluorine containing esters and polymers thereof |
| US3356628A (en) * | 1964-12-01 | 1967-12-05 | Minnesota Mining & Mfg | Copolymers of perfluoro acrylates and hydroxy alkyl acrylates |
| US3329661A (en) * | 1964-12-01 | 1967-07-04 | Minnesota Mining & Mfg | Compositions and treated articles thereof |
| US3412179A (en) * | 1966-06-27 | 1968-11-19 | Geigy Chem Corp | Polymers of acrylyl perfluorohydroxamates |
| GB1215861A (en) * | 1967-02-09 | 1970-12-16 | Minnesota Mining & Mfg | Cleanable stain-resistant fabrics or fibers and polymers therefor |
| GB1263148A (en) * | 1968-04-03 | 1972-02-09 | Toray Industries | Antistatic copolymers and their use in the treatment of synthetic fibers |
| US3544537A (en) * | 1968-05-31 | 1970-12-01 | Du Pont | Poly(perfluoroalkoxy)polyfluoroalkyl acrylate-type esters and their polymers |
| US3654244A (en) * | 1970-03-16 | 1972-04-04 | Us Agriculture | Polymers for soil-release textile finishes |
| CH549608A (de) * | 1970-08-24 | 1974-05-31 | Ciba Geigy Ag | Verfahren zur herstellung von polymerisationsprodukten und deren verwendung. |
-
1974
- 1974-07-11 US US05/487,606 patent/US3944527A/en not_active Expired - Lifetime
-
1975
- 1975-05-27 CA CA227,864A patent/CA1064641A/en not_active Expired
- 1975-07-10 JP JP50084051A patent/JPS6025549B2/ja not_active Expired
- 1975-07-10 GB GB29113/75A patent/GB1511572A/en not_active Expired
- 1975-07-10 DE DE19752531119 patent/DE2531119A1/de active Granted
- 1975-07-10 BE BE158167A patent/BE831217A/xx not_active IP Right Cessation
- 1975-07-10 FR FR7521702A patent/FR2277840A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2277840A1 (fr) | 1976-02-06 |
| JPS6025549B2 (ja) | 1985-06-19 |
| CA1064641A (en) | 1979-10-16 |
| GB1511572A (en) | 1978-05-24 |
| US3944527A (en) | 1976-03-16 |
| BE831217A (fr) | 1976-01-12 |
| DE2531119A1 (de) | 1976-01-29 |
| JPS5131790A (en, 2012) | 1976-03-18 |
| FR2277840B1 (en, 2012) | 1980-04-30 |
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| 8110 | Request for examination paragraph 44 | ||
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