CA2788217C - Non-aqueous composition comprising partially fluorinated methacrylic polymers - Google Patents
Non-aqueous composition comprising partially fluorinated methacrylic polymers Download PDFInfo
- Publication number
- CA2788217C CA2788217C CA2788217A CA2788217A CA2788217C CA 2788217 C CA2788217 C CA 2788217C CA 2788217 A CA2788217 A CA 2788217A CA 2788217 A CA2788217 A CA 2788217A CA 2788217 C CA2788217 C CA 2788217C
- Authority
- CA
- Canada
- Prior art keywords
- fluorinated
- methacrylate
- polymer
- substrate
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims description 24
- 125000005395 methacrylic acid group Chemical group 0.000 title description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 33
- -1 fluorinated hydroxyalkyl methacrylate Chemical compound 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 19
- 239000000758 substrate Substances 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 33
- 239000010985 leather Substances 0.000 claims description 23
- 235000019738 Limestone Nutrition 0.000 claims description 11
- 239000006028 limestone Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 6
- 239000010438 granite Substances 0.000 claims description 6
- 239000004579 marble Substances 0.000 claims description 6
- 239000004575 stone Substances 0.000 claims description 6
- 239000011449 brick Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004567 concrete Substances 0.000 claims description 5
- 239000011440 grout Substances 0.000 claims description 4
- 239000010440 gypsum Substances 0.000 claims description 4
- 229910052602 gypsum Inorganic materials 0.000 claims description 4
- 239000004570 mortar (masonry) Substances 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 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 claims description 3
- 229930014626 natural product Natural products 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 description 43
- 235000019198 oils Nutrition 0.000 description 43
- 238000012360 testing method Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 18
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 14
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 14
- 238000010998 test method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 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 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 7
- 230000002940 repellent Effects 0.000 description 7
- 239000005871 repellent Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000015241 bacon Nutrition 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 235000019519 canola oil Nutrition 0.000 description 2
- 239000000828 canola oil Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 235000019674 grape juice Nutrition 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 235000008960 ketchup Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000870659 Crassula perfoliata var. minor Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004772 Sontara Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 235000015123 black coffee Nutrition 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012864 cross contamination Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical group CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000015071 dressings Nutrition 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 229920001778 nylon Polymers 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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 239000000123 paper Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- 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
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- 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
-
- 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
- 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
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paints Or Removers (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Civil Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Dispersion Chemistry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30373710P | 2010-02-12 | 2010-02-12 | |
| US61/303,737 | 2010-02-12 | ||
| US13/010,960 US8975348B2 (en) | 2010-02-12 | 2011-01-21 | Non-aqueous composition comprising partially fluorinated methacrylic polymers |
| US13/010,960 | 2011-01-21 | ||
| PCT/US2011/024526 WO2011100546A1 (en) | 2010-02-12 | 2011-02-11 | Non-aqueous composition comprising partially fluorinated methacrylic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2788217A1 CA2788217A1 (en) | 2011-08-18 |
| CA2788217C true CA2788217C (en) | 2018-06-05 |
Family
ID=43903846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2788217A Expired - Fee Related CA2788217C (en) | 2010-02-12 | 2011-02-11 | Non-aqueous composition comprising partially fluorinated methacrylic polymers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8975348B2 (enExample) |
| EP (1) | EP2534183B1 (enExample) |
| JP (1) | JP5836284B2 (enExample) |
| KR (1) | KR101731667B1 (enExample) |
| CN (1) | CN102753591B (enExample) |
| AU (1) | AU2011215758B2 (enExample) |
| CA (1) | CA2788217C (enExample) |
| NZ (1) | NZ601162A (enExample) |
| SG (1) | SG183121A1 (enExample) |
| WO (1) | WO2011100546A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5947655B2 (ja) * | 2012-08-02 | 2016-07-06 | 日東電工株式会社 | ポリテトラフルオロエチレン多孔質膜、並びに、それを用いた通気膜および通気部材 |
| US20140154519A1 (en) * | 2012-12-05 | 2014-06-05 | E I Du Pont De Nemours And Company | Non-aqueous composition comprising partially fluorinated methacrylic polymers |
| US9546933B2 (en) * | 2014-07-30 | 2017-01-17 | The Boeing Company | Determining aerosol material compatibility |
| JP6953722B2 (ja) * | 2016-01-18 | 2021-10-27 | ダイキン工業株式会社 | シーリング材組成物 |
| JP6693403B2 (ja) * | 2016-12-15 | 2020-05-13 | 信越化学工業株式会社 | 硬化性樹脂組成物 |
| BE1029387B1 (nl) * | 2021-05-05 | 2022-12-06 | Flooring Ind Ltd Sarl | Werkwijze voor het vervaardigen van panelen; en panelen hiermee bekomen |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459696A (en) * | 1965-06-24 | 1969-08-05 | Du Pont | Water-repellent compositions |
| JPS504800A (enExample) | 1973-05-15 | 1975-01-18 | ||
| US4141755A (en) * | 1974-03-26 | 1979-02-27 | National Patent Development Corporation | Masonry construction member impregnated with a copolymer of hydroxy alkyl acrylate or methacrylate with long chain alkyl acrylate or methacrylate |
| JPS58197374A (ja) | 1982-05-11 | 1983-11-17 | 小松精練株式会社 | 耐久性撥水加工方法 |
| FR2540131B1 (fr) * | 1983-01-28 | 1986-04-04 | Atochem | Compositions et procede pour le traitement oleophobe et hydrophobe des materiaux de construction |
| DE3877261T2 (de) * | 1987-05-25 | 1993-05-19 | Daikin Ind Ltd | Copolymer und diesen enthaltende oel- und wasserabweisende zusammensetzung. |
| JP2503657B2 (ja) * | 1989-06-05 | 1996-06-05 | 大日本インキ化学工業株式会社 | 撥水撥油剤 |
| JP2615252B2 (ja) * | 1990-08-28 | 1997-05-28 | 富士写真フイルム株式会社 | 電子写真式平版印刷用原版 |
| JPH0765033B2 (ja) | 1990-07-20 | 1995-07-12 | 旭硝子株式会社 | 弗素系撥水撥油剤 |
| US5061769A (en) * | 1990-12-17 | 1991-10-29 | Allied-Signal Inc. | Fluoropolymers and fluoropolymer coatings |
| JP3110773B2 (ja) * | 1991-01-28 | 2000-11-20 | 三菱レイヨン株式会社 | 熱硬化被覆組成物 |
| US5177154A (en) * | 1991-04-30 | 1993-01-05 | National Patent Development Corp. | Environmental coating solution |
| JP3148327B2 (ja) | 1992-01-31 | 2001-03-19 | 大日本インキ化学工業株式会社 | パーフルオロアルキル基含有共重合体非水分散液及び撥水撥油剤 |
| JPH06240239A (ja) | 1993-02-17 | 1994-08-30 | Asahi Glass Co Ltd | 撥水撥油剤組成物 |
| US5344903A (en) * | 1993-04-14 | 1994-09-06 | E. I. Du Pont De Nemours And Company | Water- and oil-repellent fluoro(meth)acrylate copolymers |
| JP3279442B2 (ja) * | 1994-09-08 | 2002-04-30 | 花王株式会社 | 撥水剤組成物及び撥水剤物品並びに撥水処理方法 |
| WO1997043481A1 (en) * | 1996-05-16 | 1997-11-20 | Daikin Industries, Ltd. | Soil-resistant finish |
| JPH10147741A (ja) * | 1996-11-15 | 1998-06-02 | Toyota Motor Corp | アクリル樹脂系塗料組成物 |
| JP3624615B2 (ja) * | 1997-02-28 | 2005-03-02 | ユニマテック株式会社 | 新規共重合体およびそれを含有する撥水撥油剤 |
| DE69811293T2 (de) * | 1997-06-20 | 2003-10-23 | Rohm And Haas Co., Philadelphia | Polymerzusammensetzungen |
| US6380336B1 (en) * | 1998-03-24 | 2002-04-30 | Nano-Tex, Llc | Copolymers and oil-and water-repellent compositions containing them |
| DE69929157T2 (de) * | 1998-11-04 | 2006-08-03 | Rohm And Haas Co. | Verwendung von Polymeren für Bauzwecke |
| JP4533476B2 (ja) * | 1999-07-07 | 2010-09-01 | 株式会社シミズ | フッ素樹脂含有カチオン電着塗料および製造方法 |
| US6451717B1 (en) * | 1999-12-14 | 2002-09-17 | E. I. Du Pont De Nemours And Company | Highly durable oil/water repellents for textiles |
| US6479605B1 (en) * | 2001-05-15 | 2002-11-12 | E. I. Du Pont De Nemours And Company | High-durability, low-yellowing repellent for textiles |
| JP3963759B2 (ja) * | 2002-04-01 | 2007-08-22 | 株式会社日本触媒 | 低屈折率組成物及び反射防止膜 |
| DE60331092D1 (de) * | 2002-10-15 | 2010-03-11 | Asahi Glass Co Ltd | Hydro- und oleophobiermittel |
| CN100374474C (zh) | 2003-06-09 | 2008-03-12 | 大金工业株式会社 | 砖石处理剂 |
| WO2005003246A1 (ja) * | 2003-07-08 | 2005-01-13 | Kyoeisha Chemical Co., Ltd. | コーティング剤用表面張力制御剤およびそれを含有するコーティング剤 |
| US7196133B2 (en) * | 2003-07-08 | 2007-03-27 | Kyoeisha Chemical Co., Ltd. | Surface tension control agent for coating material and coating material containing same |
| JP2005054020A (ja) | 2003-08-01 | 2005-03-03 | Yunimatekku Kk | 撥水撥油剤 |
| US7101924B2 (en) * | 2003-08-12 | 2006-09-05 | Hexion Specialty Materials, Inc. | Water-dispersible polyester stabilized, acid-treated, fluoroalkyl compositions |
| TWI226346B (en) | 2003-08-21 | 2005-01-11 | Jintex Corp Ltd | Nano fluorinated water-and oil-repellent and process for producing the same |
| JP2005146102A (ja) | 2003-11-14 | 2005-06-09 | Daikin Ind Ltd | 撥水撥油剤組成物の製造方法 |
| JP4984889B2 (ja) | 2004-03-12 | 2012-07-25 | ダイキン工業株式会社 | 皮革および蛋白質繊維の処理のための重合体および処理剤 |
| CN1938346A (zh) | 2004-04-09 | 2007-03-28 | 大金工业株式会社 | 用于处理砖石的聚合物和处理剂 |
| JP4996875B2 (ja) | 2005-04-28 | 2012-08-08 | 日華化学株式会社 | 撥水剤、撥水加工方法及び撥水性繊維製品 |
| WO2007080055A2 (en) | 2006-01-10 | 2007-07-19 | Clariant International Ltd | Fluorous telomeric compounds and polymers containing same |
| WO2008000681A1 (en) | 2006-06-27 | 2008-01-03 | Clariant International Ltd | Fluorous telomeric compounds and polymers containing same |
| RU2444534C2 (ru) * | 2006-08-25 | 2012-03-10 | Клариант Файненс (Бви) Лимитед | Масло-, водо- и грязеотталкивающие сополимеры перфторалкилэтилметакрилата |
| US20080146758A1 (en) * | 2006-12-14 | 2008-06-19 | Peter Michael Murphy | Low temperature cure repellents |
| US20080202384A1 (en) * | 2007-02-28 | 2008-08-28 | Sheng Peng | Fluoropolymer compositions and method of use |
| EP2141212B1 (en) | 2007-04-27 | 2013-09-18 | Asahi Glass Company, Limited | Water-repellant/oil-repellant composition, method for production thereof, and article |
| CN101668827A (zh) | 2007-04-27 | 2010-03-10 | 旭硝子株式会社 | 斥水斥油剂组合物及其制造方法及物品 |
| EP2166059B1 (en) | 2007-06-12 | 2015-09-02 | Asahi Glass Company, Limited | Water-repellent/oil-repellent composition, method for producing the same, and article |
| CN101687938B (zh) | 2007-07-11 | 2012-07-18 | 旭硝子株式会社 | 斥水斥油剂组合物的制造方法及物品 |
| JP2009035689A (ja) | 2007-08-03 | 2009-02-19 | Asahi Glass Co Ltd | 撥水耐油剤組成物、撥水耐油紙およびその製造方法 |
| JPWO2009041650A1 (ja) | 2007-09-28 | 2011-01-27 | 旭硝子株式会社 | 撥水撥油剤組成物および物品 |
| JP5439743B2 (ja) | 2007-10-11 | 2014-03-12 | ユニマテック株式会社 | 撥水撥油剤 |
| KR101533135B1 (ko) * | 2008-06-02 | 2015-07-01 | 아사히 가라스 가부시키가이샤 | 공중합체, 그 제조 방법 및 발유제 조성물 그리고 그 처리 물품 |
-
2011
- 2011-01-21 US US13/010,960 patent/US8975348B2/en active Active
- 2011-02-11 NZ NZ60116211A patent/NZ601162A/en not_active IP Right Cessation
- 2011-02-11 SG SG2012056503A patent/SG183121A1/en unknown
- 2011-02-11 CN CN201180009144.8A patent/CN102753591B/zh not_active Expired - Fee Related
- 2011-02-11 AU AU2011215758A patent/AU2011215758B2/en not_active Ceased
- 2011-02-11 JP JP2012553034A patent/JP5836284B2/ja not_active Expired - Fee Related
- 2011-02-11 EP EP20110704704 patent/EP2534183B1/en not_active Not-in-force
- 2011-02-11 WO PCT/US2011/024526 patent/WO2011100546A1/en not_active Ceased
- 2011-02-11 CA CA2788217A patent/CA2788217C/en not_active Expired - Fee Related
- 2011-02-11 KR KR1020127023751A patent/KR101731667B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102753591B (zh) | 2016-03-16 |
| CA2788217A1 (en) | 2011-08-18 |
| CN102753591A (zh) | 2012-10-24 |
| WO2011100546A1 (en) | 2011-08-18 |
| KR20130008545A (ko) | 2013-01-22 |
| US8975348B2 (en) | 2015-03-10 |
| KR101731667B1 (ko) | 2017-04-28 |
| JP5836284B2 (ja) | 2015-12-24 |
| JP2013519758A (ja) | 2013-05-30 |
| NZ601162A (en) | 2014-07-25 |
| US20110200829A1 (en) | 2011-08-18 |
| AU2011215758B2 (en) | 2015-07-02 |
| AU2011215758A1 (en) | 2012-07-26 |
| SG183121A1 (en) | 2012-09-27 |
| EP2534183A1 (en) | 2012-12-19 |
| EP2534183B1 (en) | 2014-01-22 |
| HK1177756A1 (zh) | 2013-08-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2788217C (en) | Non-aqueous composition comprising partially fluorinated methacrylic polymers | |
| KR20090051068A (ko) | 플루오르화 아미드를 포함하는 폴리(메트)아크릴아미드 및 폴리(메트)아크릴레이트 | |
| AU2011258284B2 (en) | Fluoropolymer additive for coatings | |
| US20140154420A1 (en) | Partially fluorinated copolymers | |
| CN103261120A (zh) | 氟化共聚物 | |
| CA2794636C (en) | Solvent-based fluoropolymer additives and their use in coating compositions | |
| HK1177756B (en) | Non-aqueous composition comprising partially fluorinated methacrylic polymers | |
| CN103261249B (zh) | 氟化的共聚物涂料共聚物 | |
| US20070066762A1 (en) | Triazole-containing fluorinated polymers | |
| CA2833819A1 (en) | Non-aqueous composition comprising partially fluorinated methacrylic polymers | |
| HK1134510A (en) | Poly(meth)acrylamides and poly(meth)acrylates containing fluorinated amide | |
| HK1188433A (en) | Fluorinated copolymers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160204 |
|
| MKLA | Lapsed |
Effective date: 20210211 |