CA1056992A - Polymere oleophobe et hydrophobe - Google Patents

Polymere oleophobe et hydrophobe

Info

Publication number: CA1056992A
Authority: CA; Canada
Prior art keywords: polymer; monomer; repeat units; polymer chain; water
Prior art date: 1974-09-12
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

Application number

CA235,513A

Other languages

English (en)

Other versions

CA235513S (en

Inventor

Stanley Temple

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1974-09-12

Filing date

1975-09-11

Publication date

1979-06-19

1974-09-12 Priority claimed from US05/505,221 external-priority patent/US4013627A/en

1975-09-11 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1979-06-19 Application granted granted Critical

1979-06-19 Publication of CA1056992A publication Critical patent/CA1056992A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 88
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 57
230000002940 repellent Effects 0.000 title claims abstract description 18
239000005871 repellent Substances 0.000 title claims abstract description 18
239000000178 monomer Substances 0.000 claims abstract description 97
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 29
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims abstract description 26
229920002554 vinyl polymer Polymers 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
238000006116 polymerization reaction Methods 0.000 claims abstract description 17
150000001450 anions Chemical class 0.000 claims abstract description 10
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 10
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
230000003381 solubilizing effect Effects 0.000 claims abstract description 6
125000003010 ionic group Chemical group 0.000 claims abstract description 5
-1 alkyl methacrylate Chemical compound 0.000 claims description 21
239000004753 textile Substances 0.000 claims description 21
239000004744 fabric Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 abstract description 5
125000002348 vinylic group Chemical group 0.000 abstract description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
239000003921 oil Substances 0.000 description 23
239000006185 dispersion Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 19
239000004094 surface-active agent Substances 0.000 description 18
238000000034 method Methods 0.000 description 16
238000012360 testing method Methods 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 10
239000000839 emulsion Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 7
229960005419 nitrogen Drugs 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000012986 chain transfer agent Substances 0.000 description 6
150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
239000000126 substance Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
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238000007792 addition Methods 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
125000005250 alkyl acrylate group Chemical group 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
150000003512 tertiary amines Chemical group 0.000 description 4
WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical class CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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238000004132 cross linking Methods 0.000 description 3
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239000000975 dye Substances 0.000 description 3
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150000002148 esters Chemical class 0.000 description 3
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
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125000001153 fluoro group Chemical group F* 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
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238000002156 mixing Methods 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
239000000758 substrate Substances 0.000 description 3
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JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
241000412626 Penetes Species 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
230000008021 deposition Effects 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
125000003438 dodecyl group Chemical group [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])* 0.000 description 2
DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
238000005108 dry cleaning Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
229920002313 fluoropolymer Polymers 0.000 description 2
239000004811 fluoropolymer Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000003999 initiator Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000009940 knitting Methods 0.000 description 2
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
229920006120 non-fluorinated polymer Polymers 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
238000010926 purge Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
238000009991 scouring Methods 0.000 description 2
238000009941 weaving Methods 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
LIFLRQVHKGGNSG-UHFFFAOYSA-N 2,3-dichlorobuta-1,3-diene Chemical compound ClC(=C)C(Cl)=C LIFLRQVHKGGNSG-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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125000001188 haloalkyl group Chemical group 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
VGUANSONTIBISX-UHFFFAOYSA-N hexadecyl(dimethyl)azanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCN(C)C VGUANSONTIBISX-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
YIADEKZPUNJEJT-UHFFFAOYSA-N n-ethyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCC YIADEKZPUNJEJT-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000004010 onium ions Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000913 palmityl 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])[H] 0.000 description 1
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000010998 test method Methods 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
YFYABWXIJBTAAM-UHFFFAOYSA-M trimethyl(2-phenyltetradecan-2-yl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC(C)([N+](C)(C)C)C1=CC=CC=C1 YFYABWXIJBTAAM-UHFFFAOYSA-M 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004260 weight control 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

CA235,513A 1974-09-12 1975-09-11 Polymere oleophobe et hydrophobe Expired CA1056992A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/505,221 US4013627A (en)	1972-09-20	1974-09-12	Oil and water repellent polymer containing onium groups

Publications (1)

Publication Number	Publication Date
CA1056992A true CA1056992A (fr)	1979-06-19

Family

ID=24009483

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,513A Expired CA1056992A (fr)	1974-09-12	1975-09-11	Polymere oleophobe et hydrophobe

Country Status (7)

Country	Link
JP (1)	JPS599666B2 (fr)
BE (1)	BE833374A (fr)
CA (1)	CA1056992A (fr)
DE (1)	DE2540829C2 (fr)
FR (1)	FR2284619A1 (fr)
GB (1)	GB1530275A (fr)
IT (1)	IT1042172B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS52138630A (en) *	1976-05-14	1977-11-18	Mitsubishi Heavy Ind Ltd	Water activated primary cell device
JPS608068B2 (ja) *	1978-09-28	1985-02-28	ダイキン工業株式会社	撥水撥油剤
US4525423A (en) *	1982-10-13	1985-06-25	Minnesota Mining And Manufacturing Company	Fluorochemical copolymers and ovenable paperboard and textile fibers treated therewith
DE3403880A1 (de) *	1984-02-04	1985-08-08	Hoechst Ag, 6230 Frankfurt	Fluoralkylgruppen enthaltende salze von ss-alkylaminopropionsaeureestern, verfahren zu ihrer synthese und deren verwendung zur herstellung waessriger, fluoralkylgruppenhaltiger polyacrylatdispersionen
JP2660312B2 (ja) *	1992-05-29	1997-10-08	ヘキスト合成株式会社	含フッ素系水性撥水撥油組成物
KR101819978B1 (ko)	2013-06-25	2018-01-19	유니마테크 가부시키가이샤	함불소 공중합체의 수성 분산액

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3637614A (en) *	1969-02-27	1972-01-25	Du Pont	Solvent soluble dry soil resistant fluoropolymers

1975
- 1975-08-29 IT IT2673675A patent/IT1042172B/it active
- 1975-09-10 FR FR7527719A patent/FR2284619A1/fr active Granted
- 1975-09-11 CA CA235,513A patent/CA1056992A/fr not_active Expired
- 1975-09-11 GB GB3738375A patent/GB1530275A/en not_active Expired
- 1975-09-12 DE DE19752540829 patent/DE2540829C2/de not_active Expired
- 1975-09-12 JP JP11012975A patent/JPS599666B2/ja not_active Expired
- 1975-09-12 BE BE160008A patent/BE833374A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE833374A (fr)	1975-12-31
DE2540829A1 (de)	1976-03-25
IT1042172B (it)	1980-01-30
FR2284619B1 (fr)	1979-06-29
GB1530275A (en)	1978-10-25
JPS599666B2 (ja)	1984-03-03
JPS5155500A (ja)	1976-05-15
DE2540829C2 (de)	1985-07-04
FR2284619A1 (fr)	1976-04-09

Publication	Publication Date	Title
US4013627A (en)	1977-03-22	Oil and water repellent polymer containing onium groups
US3645990A (en)	1972-02-29	Fluorinated oil- and water-repellent and dry soil resistant polymers
CA1271892A (fr)	1990-07-17	Copolymeres impermeables a l'huile et a l'eau
CA1192690A (fr)	1985-08-27	Traitement de produits textiles a l'aide d'une composition renfermant un ester et un polymere fluoro-aliphatiques
US3944527A (en)	1976-03-16	Fluoroaliphatic copolymers
US3462296A (en)	1969-08-19	Fluorinated oil- and water-repellent copolymer and process for treating fibrous materials with said copolymer
US3544537A (en)	1970-12-01	Poly(perfluoroalkoxy)polyfluoroalkyl acrylate-type esters and their polymers
EP1399618B1 (fr)	2006-11-29	Materiau d'hydrofugation et d'oleofugation a durabilite elevee et a faible jaunissement destine a des textiles
US3232691A (en)	1966-02-01	Dyeing with copolymeric dyes and crosslinking the latter
US4728707A (en)	1988-03-01	Water- and oil-repellent
US3546187A (en)	1970-12-08	Oil- and water-repellent polymeric compositions
KR20000016701A (ko)	2000-03-25	수분산형 불소계 발수발유제
CA1117707A (fr)	1982-02-09	Matieres textiles a caracteristiques durables de resistance a la souillure et a l'absorption de l'eau, et methode de production connexe
US3995085A (en)	1976-11-30	Fabrics treated with hybrid tetracopolymers and process
JPH04248863A (ja)	1992-09-04	弗素−含有ポリマーの水性分散液
CA1056992A (fr)	1979-06-19	Polymere oleophobe et hydrophobe
JP3744034B2 (ja)	2006-02-08	夾雑物安定性に優れる水分散型撥水撥油剤組成物
JP3744035B2 (ja)	2006-02-08	安定性に優れる水分散型撥水撥油剤組成物
JPH04214469A (ja)	1992-08-05	繊維仕上げのための方法および組成物
US3547856A (en)	1970-12-15	Fluorinated oil and water repellents
US3213053A (en)	1965-10-19	Antistatic composition and treatment of synthetic linear polymer texiles therewith
US3657173A (en)	1972-04-18	Oil and water repellent compositions
JPH07173772A (ja)	1995-07-11	水分散型フッ素系撥水撥油剤およびその製造方法
US3366507A (en)	1968-01-30	Textile coated with antistatic composition
JP2503657B2 (ja)	1996-06-05	撥水撥油剤