NO119050B - - Google Patents
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- NO119050B NO119050B NO163781A NO16378166A NO119050B NO 119050 B NO119050 B NO 119050B NO 163781 A NO163781 A NO 163781A NO 16378166 A NO16378166 A NO 16378166A NO 119050 B NO119050 B NO 119050B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- perfluorooctanoate
- mixture
- acetone
- chloride
- Prior art date
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- 229920000642 polymer Polymers 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000005871 repellent Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- -1 perfluoroheptyl Chemical group 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- HYPABTNNOFXMFZ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OCCOC(=O)C=C HYPABTNNOFXMFZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SNGREZUHAYWORS-UHFFFAOYSA-M 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-M 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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- AQQBRCXWZZAFOK-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(Cl)=O AQQBRCXWZZAFOK-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- QFQXAVRUGZXRHM-UHFFFAOYSA-N hex-1-ene-1,6-diol Chemical compound OCCCCC=CO QFQXAVRUGZXRHM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 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
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical compound CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/4857—Other macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/4838—Halogenated polymers
- C04B41/4842—Fluorine-containing polymers
- C04B41/4846—Perfluoro-compounds
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Polymers & Plastics (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Description
Polymere med oljeavstøtende egenskaper, inneholdende eller bestående av tilbakevendende enheter avledet fra visse
fluorerte umettede forbindelser.
Denne oppfinnelse angår polymere med oljeavstbtende egenskaper inneholdende eller bestående ev tilbakevendende enheter avledet fra visse fluorerte umettede forbindelser, nemlig enheter
hvor R^ er en perfluoralkylgruppe med 3-17 cerbonatomer, R2 er et hydrogenatom eller en methylgruppe, og Y er et radikal av en elifatisk toverdig alkohol.
Eksempler" på radikalet R-^er perfluorbutyl, perfluorpentyl, perfluorhexyl, perfluorheptyl, perfluoroctyl, perfluornonyl og perfluordecyl, og eksempler på radikalet Y er radikaler avledet fra ethylenglycol, propylenglycol, 1,3-propandiol, 1,4-butandiol, 1,5-pentandiol, 1,6-hexendiol, neopentylglycol, 2,2,4-trimethyl-1,3-pentandiol, diethylenglycol, triethylenglycol, tetraethylen-glycol, dipropylenglycol og tripropylenglycol.
Når polymerene også inneholder enheter av andre umettede monomere, kan disse spesielt være avledet frs arylforbindelser, vinylforbindelser og allylforbindelser.
Homopolymerene og sampolymerene ifblge oppfinnelsen har interessante oljeavstbtende egenskaper og anvendes for be-handling av porbse eller ikke-porbse materialer som bnskes be-skyttet mot smuss eller gjort resistente overfor fuktning med vege-tabilske, animalske 'éller mineralske oljer og fett, hydrocarboner og organiske>opplbsningsmidler. Eksempler på sådanne materialer er naturlige og syntetiske tekstilfibre, papir, tre, teglsten, asbest, asbestsement, betong, lær, skinn og lignende.
Homopolymerene ifblge oppfinnelsen fremstilles ved polymerisering av en fluorert, umettet forbindelse av den generelle formel:
hvor R-j^ og Y har de ovenfor angitte betydninger, og R^COO er en acrylsyre- eller methacrylsyrerest. Polymeriseringen kan utfores etter de vanlige metoder, enten i organisk opplbsning eller i vandig emulsjon, i nærvær av konvensjonelle polymerisasjonskata-lysatorer, såsom organiske og uorganiske peroxyder, hydroperoxyder, persyrer, persalter, diazoforbindelser, redoxsystemer og lignende. Polymeriseringen i vandig emulsjon finner sted i nærvær av anion-iske, kationiske og/eller ikke-ioniske overflateektive midler, emulsjonsstabiliserende midler og lignende.
Sampolymerene ifblge oppfinnelsen fremstilles på tilsvarende måte som homopolymerene, idet forbindelser av formel (II) poly-meriseres innbyrdes eller med andre ssmpolymeriserbare umettede monomere, spesielt (a) acrylderivater, såsom acrylsyre- og methacrylsyreestere og forgrenede og uforgrenede alifatiske alko-holer og substituerte eller usubstituerte acrylamider og meth-acrylamider, (b) vinylderivater, såsom vinylacetat, vinylklorid, vinylmethylether, vinylmethylketon, styren og vinyltoluen og (c) allylderivater, såsom diallylf thalet, triallylcyanurat og lign-r ende.
Den vandige opplbsning eller vandige emulsjon som fåes av homopolymerene og sampolymerene, inneholder vanligvis 1-30 vektprosent polymer.
Forbindelsene av formel (II) er nye, fluorerte blandede estere med ethylenisk umettethet, og fremtrer som tette, viskose væsker med hbyt kokepunkt, som er praktisk talt uoppløselige i vann, har liten opplbselighet i mettede alifatiske hydrocarboner og er opplbselige i aceton, ether og aromatiske hydrocarboner. De kan fremstilles ved at et glycolmonoalkenoat av formelen: hvor RjCOO og Y har de ovenfor angitte betydninger, omsettes med et perfluoralkansyrederivat av formelen
hvor Y er en hydroxylgruppe eller et halogenatom og R-^har den ovenfor angitte betydning.
Reaksjonen som finner sted, kan representeres ved ligningen:
hvor symbolene har de ovenfor angitte betydninger.
Glycolmonoalkenoetene som anvendes som utgangsmaterialer, kan fremstilles ved hjelp av de vanlige forestringsmetoder. Som eksempler på sådanne metoder kan nevnes:
1. kondensasjon av en alkensyre med et alkylenoxyd,
2. kondensasjon av et alkensyrehalogenid, med en toverdig alkohol, 3. kondensasjon av et metallsalt av en alkensyre med et halogen-hydrin av en toverdig alkohol,
4 kondensasjon av en alkensyre med en toverdig alkohol, og
5. omforestring av en alkylester av en alkensyre med en toverdig alkohol.
Disse reaksjoner kan utfores med et overskudd av den tover-dige alkohol eller av et funksjonelt dervat av denne
I det nedenstående illustreres fremstillingen av en av forbindelsene av formel II som er anvendbare for fremstilling av polymerene ifblge oppfinnelsen.
A. Ethylenglycolacrylat- perfluorocta- noat
11,6 g (0,1 mol) ethylenglycolmonoacrylat, 7,9 g (0,1 mol) pyridin, 0,5 g hydrokinon og 175 ml vannfri ether anbringes i en 250 ml<*>s kolbe som er utstyrt med rbrer, en dråpetrakt og en til-bakelopskondensator forbindet med et kalsiumkloridrbr. 43,25 g (0,1 mol) perfluoroctanoylklorid tildryppes i lbpet av 30 minutter, idet det påsees et temperaturen ikke overstiger 25°C. Etter endt tilfbrsel av syrekloridet omrbres blandingen i ytterligere 20 minutter ved romtemperatur. Det utfeldte pyridinhydroklorid frafUtreres og vaskes med ether. Ethervaskevæskene slåes sammen og vaskes med fire porsjoner vann a 50 ml. Etheropplbsningen tbr-res deretter over vannfritt magnesiumsulfat og filtreres, hvor-etter etheren avdestilleres i vakuum. Det erholdes 46,7 g ethylenglycolacrylat-perfluoroctanoat, hvilket tilsvarer et utbytte på 91 % ev det teoretiske, beregnet på forbrukt perfluoroctenoyl-klorid.
K.p. 242°C/746 mm Hg; n^<4>'<5>= 1,34718
Analyse:
beregnet: C 30,48 % H 1,38 £ F 55,64 %
funnet: C 30,80 i» H 1,48 % P 55,82 %
Analyse i spektrets
infrerbde område: C=C: 1620 og 1635 cm<-1>
C=0 umettet ester: 1730 cm<-1>
C=0 fluorert ester: 1780 cm""1
I det nedenstående illustreres aom eksempler fremstillingen av et par homopolymere og et per sampolymere ifblge oppfinnelsen.
Eksempel 1
Polymerisering av ethylenglycol- acrylat- perfluoroctanoat
132 g destillert vann, 13 g abeton, 4,4 g trimethyloctadeoyl-ammoniumklorid i opplbsning (50 i» av ammoniumseltet, 13 % vann og 37 % isopropenol), og 0,88 g a,a'-azo-bis-iaobutyramidin-dihydro-klorid anbringes i en 250 ml's kolbe som er utstyrt med en rOrer, en dråpetrakt og en vertikal kondensator aamt et rbr for tilfbrael av nitrogen. Denne blanding oppvarmea til 65°C under kontinuerlig omrbring, og en nitrogenstrbm ledes over den, idet en blanding av 19 g ethylenglycolecrylat-perfluoroctanoat (fremstilt som beskrevet under punkt A ovenfor) og 9 g aceton tildryppes i lopet ev 210 minutter. Produktet som erholdes, er en emulsjon som inneholder 10,6 # ethylenglycolecrylat-perfluoroctenoet-homopolymer.
Eksempel 2
Polymerisering av ethylenglycolmethacrylet- perfluoroctenoet
66 g deatillert vann, 6 g aceton, 2,2 g trimethyloctadecylemmoniumklorid i 50 £-ig vandig opplbsning (se eksempel 1) og 0,44 g a ,oc'-azo-bis-iaobutyremidin-dihydroklorid anbringes i det i eksempel 1 anvendte apparat. Denne blanding oppvarmes til 65°C og omrbres, der ledes over den en svak nitrogenatrbm, og en blanding av 14 g ethylenglycolmethecrylet-perfluoroctenoet (fremstilt som beskrevet under punkt A ovenfor) og 5 g aceton tildryppes i lbpet av 3 timer. Blandingen tillates deretter å stå til evkjbling. Produktet som erholdes, er en emulsjon som inneholder 15 # ethylenglycolmethecry-lat-perfluoroctanoat-homopolymer.
Eksempel 3
Sempolymerisering av 2,2-dimethyl-l,3-prop8ndiol-methecrylat-perfluoroctanoat og N- methylol- acrylamid 60 g destillert vann, 7,4 g aceton, 0,3 g N-methylol-acrylamid, 1 g trimethyloctadecylammoniumklorid i 50 #-ig vandig opplbsning ( ae eksempel 1) og 0,8 g a,o'-azo-bis-isobutyremidin-dihydroklorid anbringes i det i eksempel 1 beskrevne apparat. En nitrogenatrbm ledes over reaktantene mens de omrbrea og oppvarmes til 65°C. En blanding ev 2,32 g 2,2-dimethyl-l,3-propendiol-methecrylet-perfluoroctanoat (fremstilt som beskrevet under punkt A ovenfor) og 4 g aceton tildryppes i lbpet av 1 time. Etter avkjbling erholdes en emulsjon som inneholder 3,4 % ev sampolymeren av 2,2-dimethyl-1,3-propandiol-methacrylat-perfluoroctanoat og N-methylol-acrylamid, av hvilke 3 ^ er avledet fra den fluorerte monomer.
Eksempel 4
Blokkpolymer av 2,2-dimethyl-l,3-propendiol-methecrylat-perfluoroctanoat, 2- ethylhexylacrylat og N- methylol- acrylemld
73,5 ml vann, 2,5 g trimethyloctadecylemmoniumklorid i opp-1bening (50 £ av ammoniumaaltet, 13 % vann og 37 % isopropanol),
0,5 g o,_'-az.o-bi8-isobutyramidin-dihydroklorid og 7,5 g aceton anbringes i en 250 ml'a kolbe som er utstyrt med en rbrer, en
dråpetrakt og en kjoler. En svak nitrogenstrom ledes over reak-sjonsblandingen som oppvarmes til og holdes ved 65°C. En blanding av 2 g 2,2-dimethy1-1,3-propandiol-methacrylat-perfluoroctanoat og 2 g aceton tildryppes derefter i lopet av 1/2 time. 0,066 g N-methylol-acrylamid tilsettes, og derefter tilsettes dråpevis en blanding av 6,6 g 2-ethyIhexy1-acrylat og 3 g aceton i lopet av 1 time. Efter IO minutters reaksjon tillates, emulsjonen å avkjoles. Produktet som erholdes, er en emulsjon av en sampolymer av 2 % 2,2-dimethy1-1,3-propandiol-methacrylat-perfluoroctanoat, 6,6 % 2-ethy1-hexy1-acrylat og 0,066 % N-methylol-acrylamid. Vektforhol-det mellom de tre bestanddeler av blokksampolymeren er 30 : 100 : 1.
Claims (2)
1.Polymere for anvendelse som middel til å gjore overflater oljeavstotende, inneholdende eller bestående av tilbakevendende enheteravledet fra fluorerte ethylenisk umettede forbindelser,karakterisert vedat de inneholder eller består av tilbakevendende enheter av strukturen:
hvor er en perf luoralkylgruppe med 3-17 carbonatomer, er et hydrogenatom eller en methylgruppe, og Y er et radikal av en alifatisktoverdig alkohol.
2. Polymere ifolge krav 1,karakterisert vedat de i tillegg til enheter av strukturen (I) inneholder enheter avledet fra monomere valgt blant acrylforbindelser, vinylforbindelser og allylforbindelser.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28800/65A GB1096392A (en) | 1965-07-07 | 1965-07-07 | Mixed esters of dihydric alcohols with perfluoroalkanoic acid ethylenically unsaturated carboxylic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
NO119050B true NO119050B (no) | 1970-03-16 |
Family
ID=10281383
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO163781A NO119050B (no) | 1965-07-07 | 1966-07-05 |
Country Status (12)
Country | Link |
---|---|
US (1) | US3470124A (no) |
AT (1) | AT262949B (no) |
BE (1) | BE683649A (no) |
CH (1) | CH455730A (no) |
DE (1) | DE1593635A1 (no) |
ES (1) | ES328782A1 (no) |
GB (1) | GB1096392A (no) |
IL (1) | IL26088A (no) |
LU (1) | LU51469A1 (no) |
NL (2) | NL6609240A (no) |
NO (1) | NO119050B (no) |
SE (1) | SE348723B (no) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4557837A (en) * | 1980-09-15 | 1985-12-10 | Minnesota Mining And Manufacturing Company | Simulation and cleanup of oil- and/or gas-producing wells |
US4482608A (en) * | 1982-07-26 | 1984-11-13 | Minnesota Mining And Manufacturing Company | Release coating for infrared imageable and thermally imageable films |
US4578504A (en) * | 1983-06-03 | 1986-03-25 | Minnesota Mining And Manufacturing Company | Acrylate and methacrylate monomers and polymers |
US4801740A (en) * | 1983-06-03 | 1989-01-31 | Minnesota Mining And Manufacturing Company | Acrylate and methacrylate monomers and polymers |
US4673539A (en) * | 1983-06-03 | 1987-06-16 | Minnesota Mining And Manufacturing Company | Process for thermoformed articles |
US4638040A (en) * | 1983-06-03 | 1987-01-20 | Minnesota Mining And Manufacturing Company | Acrylate and methacrylate monomers and polymers |
US4786446A (en) * | 1985-05-17 | 1988-11-22 | Minnesota Mining And Manufacturing Company | Process of forming a hydroxy-substitute polymeric shaped article |
US4921884A (en) * | 1987-02-26 | 1990-05-01 | Minnesota Mining And Manufacturing Company | Hydroxy-substituted polymeric shaped hydrogel article |
US4791166A (en) * | 1988-03-23 | 1988-12-13 | Hoechst Celanese Corporation | Fluorocarbon polymer compositions and methods |
DE3941871A1 (de) * | 1989-12-19 | 1991-06-20 | Basf Ag | Neue fluorkohlenstoff- und oxypropylenalkylethergruppen gebunden enthaltende ester, diese ester enthaltende emulsionen und deren verwendung zur herstellung von zellhaltigen kunststoffen nach dem polyisocyanat-polyadditionsverfahren |
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 |
US5308511A (en) * | 1992-12-04 | 1994-05-03 | Minnesota Mining And Manufacturing Company | Solvent-based water- and oil-repellent treating agent |
DE69330790T2 (de) * | 1993-10-19 | 2002-05-23 | Minnesota Mining And Mfg. Co., Saint Paul | Hochleistungszusammensetzungen mit wasser- und ölabweisenden Eigenschaften |
EP0648890B1 (en) * | 1993-10-19 | 1996-12-11 | Minnesota Mining And Manufacturing Company | High performance oil and water repellent compositions |
DE69424173T2 (de) * | 1994-11-24 | 2000-09-28 | Minnesota Mining & Mfg | Carbodiimide-Verbindungen und dauerhafte wasserabweisende Zusammensetzungen, die diese Verbindungen enthalten |
US5753607A (en) * | 1996-04-01 | 1998-05-19 | Sara Lee Corporation | Cleaning and polishing composition |
US6426025B1 (en) | 1997-05-12 | 2002-07-30 | 3M Innovative Properties Company | Process for extruding fibers |
DK1521786T3 (da) * | 2002-07-16 | 2008-07-28 | Alcon Inc | Materialer til oftalmiske og otorhinolaryngologiske anordninger |
WO2006059349A1 (en) * | 2004-11-30 | 2006-06-08 | Vinod Chintamani Malshe | A novel method for introduction of fluorine in monomers and polymers, and monomers and polymers thereof |
DE102005039536A1 (de) * | 2005-08-18 | 2007-02-22 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
JP4623324B2 (ja) * | 2008-03-18 | 2011-02-02 | 信越化学工業株式会社 | 水酸基を有する単量体、高分子化合物、レジスト材料及びパターン形成方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA726763A (en) * | 1966-01-25 | J. Verbanic Carl | Unsaturated esters of fluorinated glycols | |
US2559750A (en) * | 1949-07-27 | 1951-07-10 | Du Pont | Aqueous colloidal dispersions of polytetrafluoroethylene and the formation of shapedstructures therefrom |
US2642416A (en) * | 1950-05-26 | 1953-06-16 | Minnesota Mining & Mfg | Fluorinated acrylates and polymers |
US2592069A (en) * | 1951-03-05 | 1952-04-08 | Minnesota Mining & Mfg | Fluorocarbon vinyl esters and polymers |
US2855434A (en) * | 1956-01-05 | 1958-10-07 | Pittsburgh Plate Glass Co | Method for preparing unsaturated aromatic compounds |
US3102103A (en) * | 1957-08-09 | 1963-08-27 | Minnesota Mining & Mfg | Perfluoroalkyl acrylate polymers and process of producing a latex thereof |
BE592804A (no) * | 1959-07-11 | |||
US3304278A (en) * | 1966-02-25 | 1967-02-14 | Pennsalt Chemicals Corp | Fluorinated unsaturated organic compounds and polymers thereof |
-
0
- NL NL127481D patent/NL127481C/xx active
-
1965
- 1965-07-07 GB GB28800/65A patent/GB1096392A/en not_active Expired
-
1966
- 1966-07-01 NL NL6609240A patent/NL6609240A/xx unknown
- 1966-07-04 LU LU51469D patent/LU51469A1/xx unknown
- 1966-07-04 IL IL26088A patent/IL26088A/en unknown
- 1966-07-05 NO NO163781A patent/NO119050B/no unknown
- 1966-07-05 BE BE683649D patent/BE683649A/xx unknown
- 1966-07-05 CH CH975766A patent/CH455730A/fr unknown
- 1966-07-05 DE DE19661593635 patent/DE1593635A1/de active Pending
- 1966-07-05 US US562511A patent/US3470124A/en not_active Expired - Lifetime
- 1966-07-06 AT AT647266A patent/AT262949B/de active
- 1966-07-06 SE SE09256/66A patent/SE348723B/xx unknown
- 1966-07-06 ES ES0328782A patent/ES328782A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES328782A1 (es) | 1967-04-16 |
LU51469A1 (no) | 1967-01-04 |
NL127481C (no) | 1900-01-01 |
SE348723B (no) | 1972-09-11 |
NL6609240A (no) | 1967-01-09 |
US3470124A (en) | 1969-09-30 |
DE1593635A1 (de) | 1970-01-29 |
AT262949B (de) | 1968-07-10 |
GB1096392A (en) | 1967-12-29 |
IL26088A (en) | 1970-05-21 |
CH455730A (fr) | 1968-05-15 |
BE683649A (no) | 1967-01-05 |
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