CA1036435A - Oil and water repellent fibrous materials and their formation - Google Patents
Oil and water repellent fibrous materials and their formationInfo
- Publication number
- CA1036435A CA1036435A CA219,565A CA219565A CA1036435A CA 1036435 A CA1036435 A CA 1036435A CA 219565 A CA219565 A CA 219565A CA 1036435 A CA1036435 A CA 1036435A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- vinyl
- alkyl radical
- mole
- hydrogen
- 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
- 239000005871 repellent Substances 0.000 title claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 11
- 230000002940 repellent Effects 0.000 title description 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000002657 fibrous material Substances 0.000 title 1
- -1 allyl ester Chemical class 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 27
- 239000000835 fiber Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001336 alkenes Chemical class 0.000 claims abstract description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000839 emulsion Substances 0.000 claims description 33
- 239000004606 Fillers/Extenders Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229920001519 homopolymer Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 230000001846 repelling effect Effects 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 12
- 239000000047 product Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002759 woven fabric Substances 0.000 description 5
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical class CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- PUMIBBNWDCWIKR-UHFFFAOYSA-M 1-(octadecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 PUMIBBNWDCWIKR-UHFFFAOYSA-M 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000000937 inactivator Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 239000003799 water insoluble solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- 241000286904 Leptothecata Species 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 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 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2962—Silane, silicone or siloxane in coating
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
- Y10T428/31544—Addition polymer is perhalogenated
-
- 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
- Y10T442/2164—Coating or impregnation specified as water repellent
- Y10T442/2172—Also specified as oil repellent
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742406002 DE2406002C3 (de) | 1974-02-08 | Verfahren zum gleichzeitigen Öl- und Wasserabweisendmachen von Fasermaterialien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1036435A true CA1036435A (en) | 1978-08-15 |
Family
ID=5906914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA219,565A Expired CA1036435A (en) | 1974-02-08 | 1975-02-07 | Oil and water repellent fibrous materials and their formation |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4004059A (en, 2012) |
| JP (1) | JPS50112597A (en, 2012) |
| AR (1) | AR201537A1 (en, 2012) |
| BE (1) | BE825030A (en, 2012) |
| BR (1) | BR7500732A (en, 2012) |
| CA (1) | CA1036435A (en, 2012) |
| CH (2) | CH582270B5 (en, 2012) |
| ES (1) | ES434523A1 (en, 2012) |
| FR (1) | FR2260652B1 (en, 2012) |
| GB (1) | GB1504202A (en, 2012) |
| IT (1) | IT1029462B (en, 2012) |
| NL (1) | NL7501492A (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4265962A (en) * | 1976-12-20 | 1981-05-05 | Burlington Industries, Inc. | Low penetration coating fabric |
| US4324827A (en) * | 1979-01-17 | 1982-04-13 | Hiraoka & Co., Ltd. | Water-proof, fuse-bonding fabric |
| DE3276379D1 (en) * | 1981-08-25 | 1987-06-25 | Teijin Ltd | Dyed polyester fiber composite structure |
| JPS5842682A (ja) * | 1981-09-07 | 1983-03-12 | Shin Etsu Chem Co Ltd | 撥水撥油組成物 |
| US4770927A (en) * | 1983-04-13 | 1988-09-13 | Chemical Fabrics Corporation | Reinforced fluoropolymer composite |
| US4567093A (en) * | 1983-04-25 | 1986-01-28 | Achilles Corporation | Rubber coated fabric |
| JPS60173166A (ja) * | 1984-02-17 | 1985-09-06 | 東レ株式会社 | ポリアミド織物 |
| US4666745A (en) * | 1984-08-23 | 1987-05-19 | Wacker-Chemie Gmbh | Organopolysiloxanes having Si-bonded hydrogen and SiC-bonded epoxy groups and a process for preparing the same |
| DE3431075A1 (de) * | 1984-08-23 | 1986-02-27 | Wacker-Chemie GmbH, 8000 München | Organopolysiloxane mit si-gebundenem wasserstoff und sic-gebundenen epoxygruppen, verfahren zu ihrer herstellung und eine verwendung dieser organopolysiloxane |
| JPS63146976A (ja) * | 1986-12-11 | 1988-06-18 | Daikin Ind Ltd | 撥水撥油剤組成物 |
| DE3737753A1 (de) * | 1987-11-06 | 1989-06-15 | Pfersee Chem Fab | Waessriges ausruestungsmittel und verfahren zur weichen hydrophob/oleophob-behandlung von fasermaterialien |
| JP2796385B2 (ja) * | 1989-12-22 | 1998-09-10 | ミネソタ マイニング アンド マニユフアクチユアリング カンパニー | 撥水撥油処理剤 |
| JPH03193975A (ja) * | 1989-12-22 | 1991-08-23 | Minnesota Mining & Mfg Co <3M> | 撥水撥油処理剤 |
| US5248789A (en) * | 1992-03-26 | 1993-09-28 | Ppg Industries, Inc. | Epoxy silicone |
| US6355081B1 (en) * | 1999-06-01 | 2002-03-12 | Usf Filtration And Separations Group, Inc. | Oleophobic filter materials for filter venting applications |
| EP1264863A1 (de) * | 2001-06-08 | 2002-12-11 | Ciba Spezialitätenchemie Pfersee GmbH | Zusammensetzungen mit Polysiloxanen und weiteren Polymeren |
| US20070190872A1 (en) * | 2006-02-16 | 2007-08-16 | Weber Robert F | Fire retardant silicone textile coating |
| US8025870B2 (en) * | 2009-07-02 | 2011-09-27 | Siltech Corporation | Vinyl ether silicone polymers |
| US9534343B2 (en) | 2012-10-18 | 2017-01-03 | The Chemours Company Fc, Llc | Partially fluorinated copolymer emulsions containing fatty acids and esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635437A (en, 2012) * | 1961-05-03 | |||
| US3385812A (en) * | 1965-06-25 | 1968-05-28 | Du Pont | Finishing composition comprising a fluorochemical and a polyorganosiloxane |
-
1975
- 1975-01-04 JP JP50000006A patent/JPS50112597A/ja active Pending
- 1975-01-30 CH CH107975A patent/CH582270B5/xx not_active IP Right Cessation
- 1975-01-30 CH CH107975D patent/CH107975A4/xx unknown
- 1975-01-31 BE BE152918A patent/BE825030A/xx unknown
- 1975-02-03 AR AR257507A patent/AR201537A1/es active
- 1975-02-04 IT IT48001/75A patent/IT1029462B/it active
- 1975-02-04 US US05/547,078 patent/US4004059A/en not_active Expired - Lifetime
- 1975-02-05 BR BR732/75A patent/BR7500732A/pt unknown
- 1975-02-06 FR FR7503782A patent/FR2260652B1/fr not_active Expired
- 1975-02-07 CA CA219,565A patent/CA1036435A/en not_active Expired
- 1975-02-07 ES ES434523A patent/ES434523A1/es not_active Expired
- 1975-02-07 NL NL7501492A patent/NL7501492A/xx not_active Application Discontinuation
- 1975-02-07 GB GB5356/75A patent/GB1504202A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2260652B1 (en, 2012) | 1977-04-15 |
| ES434523A1 (es) | 1977-03-16 |
| IT1029462B (it) | 1979-03-10 |
| BE825030A (fr) | 1975-05-15 |
| FR2260652A1 (en, 2012) | 1975-09-05 |
| AR201537A1 (es) | 1975-03-21 |
| CH107975A4 (en, 2012) | 1976-05-31 |
| AU7792575A (en) | 1976-08-05 |
| CH582270B5 (en, 2012) | 1976-11-30 |
| BR7500732A (pt) | 1975-11-18 |
| JPS50112597A (en, 2012) | 1975-09-04 |
| US4004059A (en) | 1977-01-18 |
| DE2406002A1 (de) | 1975-08-14 |
| NL7501492A (nl) | 1975-08-12 |
| DE2406002B2 (de) | 1976-09-30 |
| GB1504202A (en) | 1978-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1036435A (en) | Oil and water repellent fibrous materials and their formation | |
| US4331797A (en) | Ester containing silylated polyethers | |
| US3809783A (en) | Siloxane polymers for soil-repellent and soil-release textile finishes | |
| US4504549A (en) | Elastomeric silicone finishes applied to substrates and method of preparing same | |
| CA2028503C (en) | Dispersions of copolymers containing perfluoroalkyl groups | |
| JPH0781081B2 (ja) | 架橋結合可能な組成物、オルガノポリシロキサン化合物の製法、そのエマルジョン又はマイクロエマルジョンの製法及び有機繊維及び織物の処理法 | |
| JPS62577A (ja) | 撥水撥油剤 | |
| US6238745B1 (en) | Water repellent for treating solids | |
| US5496401A (en) | Aqueous emulsion containing an oxidatively crosslinked aminopolysiloxane | |
| DE69104448T2 (de) | Faserbehandlungsmittelzusammensetzung. | |
| US3995085A (en) | Fabrics treated with hybrid tetracopolymers and process | |
| JP2885390B2 (ja) | 繊維処理用組成物 | |
| WO2002068752A2 (en) | Water repellent textile finishes and method of making | |
| EP1735359B1 (en) | Polymeric reaction products from substituted aminosiloxanes | |
| US3716517A (en) | Siloxane polymers for soil-repellent and soil-release textile finishes | |
| CA2048890C (en) | Silicone textile finishes | |
| US3903123A (en) | Fluorine-containing organopolysiloxanes, process for their manufacture, and their use | |
| EP0159568B1 (en) | The use of higher alkyl modified terpolymeric silicones as fiber or textile finishes | |
| JPS6151070B2 (en, 2012) | ||
| US4113947A (en) | Addition products of an n-allylamino-s-triazine and an organopolysiloxane | |
| US10954343B2 (en) | Compositions comprising beta-ketocarbonyl-functional organosilicon compounds | |
| US3949136A (en) | Fluorine-containing organopolysiloxanes, process for their use | |
| JPH08109580A (ja) | 繊維処理用組成物 | |
| EP0089784B1 (en) | Method for durable press finish using formaldehyde-free organosilicon compositions and textiles therefrom | |
| US4463036A (en) | Process for imparting hydrophilicity to fabric |