CA2083768A1 - Protection of non-aqueous systems with biocides - Google Patents
Protection of non-aqueous systems with biocidesInfo
- Publication number
- CA2083768A1 CA2083768A1 CA 2083768 CA2083768A CA2083768A1 CA 2083768 A1 CA2083768 A1 CA 2083768A1 CA 2083768 CA2083768 CA 2083768 CA 2083768 A CA2083768 A CA 2083768A CA 2083768 A1 CA2083768 A1 CA 2083768A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- formula
- paint formulation
- compound
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003139 biocide Substances 0.000 title claims abstract description 20
- 239000012770 industrial material Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 31
- 239000003973 paint Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 238000009472 formulation Methods 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 230000003373 anti-fouling effect Effects 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 8
- 230000003115 biocidal effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 230000003019 stabilising effect Effects 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 abstract description 5
- 244000005700 microbiome Species 0.000 abstract 1
- -1 phosphonium halides Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- RHCFCHADDXGWJE-UHFFFAOYSA-N 1-chloro-3-methylbuta-1,3-diene Chemical compound CC(=C)C=CCl RHCFCHADDXGWJE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 241001523707 Balanidae Species 0.000 description 1
- 241000700670 Bryozoa Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241001521340 Hydroidolina Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 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
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 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
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 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
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920000140 heteropolymer Polymers 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- HDHLIWCXDDZUFH-UHFFFAOYSA-N irgarol 1051 Chemical compound CC(C)(C)NC1=NC(SC)=NC(NC2CC2)=N1 HDHLIWCXDDZUFH-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 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
- 239000012860 organic pigment 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 150000003002 phosphanes Chemical class 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- YCBRTSYWJMECAH-UHFFFAOYSA-N tributyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC YCBRTSYWJMECAH-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/34—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-halogen bonds; Phosphonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Abstract of the disclosure Protection of non-aqueous systems with biocides Non-aqueous and water-insoluble industrial materials are stabilised and protected against attack by harmful micro-organisms by incorporating in the systems to be stabilised phosphonium chlorides of formula 1 (C4Hg)3PCnH2n+1?Cl?(I) wherein n is an integer from 8 to 16.
Description
~ ~7~
Protection of non-aqueous svstems with biocides The present invention relates to a process for stabilising non-aqueous systems against attack by harmful organisms using phosphonium chlorides.
Phosphonium chlorides have microbiological activity. A process for treating water using phosphonium halides as biocides is disclosed, for example, in EP-B-0 066 544. The use of non-hygroscopic phosphonium tetrafluoroborates or phosphonium hexafluorophosphates as biocides for industrial material protection is disclosed in EP-A-0 332 578. Antiseptic detergent compositions containing phosphonium halides are~disclosed in US-A-3 281 365.
There is still a need to protect non-aqueous systems effectively against attack by harmful organisms.
Surprisingly, it has now been found that specific alkyltributylphosphonium chlorides, although in contrast to the corresponding tetrafluoroborates they have hygroscopic properties and are soluble ~o an unlimited degree in water, are admirably suited for protecting non-aqueous systems.
The invention accordingly relates to a process for stabilising non-aqueous and water-insoluble industrial materials against attack by harmful organisms, which comprises incorporating in the system to be stabilised phosphonium chlorides of formula I
[(C4H9)3 PCnH2n+1] Cl (I) wherein n is an in~teger from 8 to 16.
The C"H2n+l radical at the phosphorus atom may be linear or branched and and is typically octyl, nonyl, decyl, dodecyl, tetradecyl, pentadecyl or hexadecyl.
The preparation of the biocides used in the process of this invention is known to the skilled person and is described, for example, in US patent specification 3 281 365. Thus the compounds may be typically prepared by alkylating tertiary phosphines with aLkyl halides:
R3P + Hal-R ~ [R3P-R ] Hal Alternative methods are the alkylation of phosphanes (also secondary and tertiary~ or of elemental phosphorus ~q.v. Houben-Weyl, Methoden der Organischen Chemie, Vol. XII,~L, page 79, Georg Thieme Verlag, Stuttgart, 1963; Houben-Weyl, Methoden der Organischen Chemie, Vol. E,1, page 491 et seq., Georg Thieme Verlag, Stuttgart, 1982.) It is expedient to dissolve the compounds of formula Ij in some cases directly after their synthesis, in an organic solvent or mixture of solvents and to incorporate them in the material to be stabilised. Before incorporation, such solutions may contain compounds of forrnula I in high concentration, e.g. 30-80 %, preferably 40-70, most preferably 45-60 %
by weight of the solution.
If such solutions of biocides of formula I are incorporated, for example, in antifouling paints, then it is best to use a solvent or mixture of solvents which is the same as that also used for the paint system. It is not necessary to remove the respective solvent from the formulation, as it evaporates when the finished coat dries.
Solvents suitable for use in the process of this invention include hydrocarbons such as toluene or xylene. High-boiling mineral oils or products customarily used as paint solvents are also suitable, typically ketones or esters, such as butyl acetate or polyglycols.
Particularly suitable solvents are those in which the compounds of formula I are at le~st 40 %, preferably 50 %, soluble.
The compounds of formula I have a particularly good activity against harmful organisms that attack industrial materials.
Illustrative examples of materials which can be protected by the process of this invention are typically plastics materials, coatings (e.g. paints and varnishes), dyes (dye formulations), rubber and adhesives.
Protection of non-aqueous svstems with biocides The present invention relates to a process for stabilising non-aqueous systems against attack by harmful organisms using phosphonium chlorides.
Phosphonium chlorides have microbiological activity. A process for treating water using phosphonium halides as biocides is disclosed, for example, in EP-B-0 066 544. The use of non-hygroscopic phosphonium tetrafluoroborates or phosphonium hexafluorophosphates as biocides for industrial material protection is disclosed in EP-A-0 332 578. Antiseptic detergent compositions containing phosphonium halides are~disclosed in US-A-3 281 365.
There is still a need to protect non-aqueous systems effectively against attack by harmful organisms.
Surprisingly, it has now been found that specific alkyltributylphosphonium chlorides, although in contrast to the corresponding tetrafluoroborates they have hygroscopic properties and are soluble ~o an unlimited degree in water, are admirably suited for protecting non-aqueous systems.
The invention accordingly relates to a process for stabilising non-aqueous and water-insoluble industrial materials against attack by harmful organisms, which comprises incorporating in the system to be stabilised phosphonium chlorides of formula I
[(C4H9)3 PCnH2n+1] Cl (I) wherein n is an in~teger from 8 to 16.
The C"H2n+l radical at the phosphorus atom may be linear or branched and and is typically octyl, nonyl, decyl, dodecyl, tetradecyl, pentadecyl or hexadecyl.
The preparation of the biocides used in the process of this invention is known to the skilled person and is described, for example, in US patent specification 3 281 365. Thus the compounds may be typically prepared by alkylating tertiary phosphines with aLkyl halides:
R3P + Hal-R ~ [R3P-R ] Hal Alternative methods are the alkylation of phosphanes (also secondary and tertiary~ or of elemental phosphorus ~q.v. Houben-Weyl, Methoden der Organischen Chemie, Vol. XII,~L, page 79, Georg Thieme Verlag, Stuttgart, 1963; Houben-Weyl, Methoden der Organischen Chemie, Vol. E,1, page 491 et seq., Georg Thieme Verlag, Stuttgart, 1982.) It is expedient to dissolve the compounds of formula Ij in some cases directly after their synthesis, in an organic solvent or mixture of solvents and to incorporate them in the material to be stabilised. Before incorporation, such solutions may contain compounds of forrnula I in high concentration, e.g. 30-80 %, preferably 40-70, most preferably 45-60 %
by weight of the solution.
If such solutions of biocides of formula I are incorporated, for example, in antifouling paints, then it is best to use a solvent or mixture of solvents which is the same as that also used for the paint system. It is not necessary to remove the respective solvent from the formulation, as it evaporates when the finished coat dries.
Solvents suitable for use in the process of this invention include hydrocarbons such as toluene or xylene. High-boiling mineral oils or products customarily used as paint solvents are also suitable, typically ketones or esters, such as butyl acetate or polyglycols.
Particularly suitable solvents are those in which the compounds of formula I are at le~st 40 %, preferably 50 %, soluble.
The compounds of formula I have a particularly good activity against harmful organisms that attack industrial materials.
Illustrative examples of materials which can be protected by the process of this invention are typically plastics materials, coatings (e.g. paints and varnishes), dyes (dye formulations), rubber and adhesives.
It is particularly advantageous lo use the biocides of forMula I for protecting plastics materials, p~ints and varnishes, espec~ally those for exterior use, but first and foremost also for protecting antifouling paints.
The paints (paint formulations) to be protected are preferably antifouling paints. These paints contain as binder the customary polymers known to those skilled in the art, typically natural and synthetic resins, homopolymers and copolymers of the monomers vinyl chloride, vinylidene chloride, styrene, vinyl toluene, vinyl esters, vinyl alcohols, acrylic acid and methacrylic acid, as well as their esters, polyester and polyamide resins, and also chlorinated rubber, natural and synthetic rubber, which may be chlorinated or cyclised, also reaction resins such as epoxy resins, polyurethane resins, unsaturated polyesters which may be converted into film-forming products of high molecular weight by adding hardeners.
The binders may be liquid or in the form of solutions. Solid coating compositions can be applied to objects by powder coating techniques. Other conventional basic components are typically tar, modifiers, dyes, inorganic or organic pigments, fillers and hardeners.
The process of this invention is utilised especially wherever objects which it is desired to protect against the growth of fungi arld algae and infestation by balanidae, bryozoa, hydroida, molluscs, protozoa, mussels and bacteria are exposed to water, especially seawater. Such objects are in particular ships' hulls, hydraulic structures, buoys or f1shing nets, and also cooling and pipe systems around or through which water flows. Quite generally the process of this invention makes it possible to protect all materials which can come in contact with water from growth or infestation by the cited organisms.
Accordingly, a preferred process is one wherein the compounds of formula I are used in antifouling paints.
A preferred process is also one wherein the compounds of forrnula I are used in paint formulations for objects which are submerged in water, especially seawater.
The amount of compounds of formula I which is used and added to the industrial materials in the process of this invention will naturally depend sobstantially on the respective utility and can therefore vary over a wide range. Depending on the envisaged end use, the compounds are used in the concentration ranges which are known to those skilled in the art.
Owing to the wide spectrum of use, concentrations of 0.1 to 40 % by weight of cornpound of formola I, based on the substrate to be treated, are suitable. Typical concentrations for treating plastics materials, such as plasdcised PVC sheets, are 0.1 to 10 % by weight, preferably 0.1 to 5 % by weight; 0.1 to 40 % by weight, preferably 0.5 to 40 % by weight, for example 10 to 40 by weight, in paint formulations such as antifouling paints.
A preferred field of use is that for protective coatings, especially for antifouling paints, to which are added, besides conventional basic and modifier components, typically 0.5 to 40 % by weight, preferably 5 to 40 % by weight, based on the total mixture, of at least one compound of formula I.
The compounds of formula I, which are dissolved in organic solvents, can be applied in pure form or together with carriers such as formuladon auxiliaries. They can also be suspended in liquid coating composidons and the like, in which case wetting agents can promote the uniform dispersion of the active compound to form homogeneous dispersions.
Further biocides may also be added.
A further utility of the compounds of formula I is incorporation in plastics materials, including polyvinyl chlorides and their co- and heteropolymers, polyalkylenes, including polyisobutylene, polyacrylates, polystyrenes, copolymers thereof, polyurethanes or polyisocyanates, polyesters, epoxy resins and the like, or in natural or synthetic rubbers.
The process of the invention can be used with advantage for providing plastics materials, including polyamides, polyurethane foams or polyisobutylene, with preservative finishes.
When using plasticisers, it is best to add a solution or dispersion of the biocide in the plasdciser to the plastics material. The antimicrobially treated pLIstics materials can be used for fabricating useful articles of all kinds for which effective protection against the most diverse germs, such as bacteria and fungi, is desired, for example plasticised PVC
sheets, foot-mats, bathroom curtains, seats, swimming pool steps, wall coverings and the like.
The compounds of formula I can also be used for elastomer coatings as well as for silicone elastomers and fluorine-containing polymers. In this connection it is expedient to use preferably high-boiling solvents, which in some cases remain in the finished product.
~g~3~75~3 A particularly advantageolls utility is incorporation in plastics or polymer materials which are used as building materials and are exposed to atmospheric influences, or which are used in the humid and moist sectors. Such materials may typically be rooflng materials or facings of polyvinyl chloride, butyl rubber, chlorinated polyethylene, polyisobutylene, chloroprene and chloroisoprene, ~PDM as well as PVC copolymers with vinyl acetate or ethyl vinyl acetate, polyacrylonitrile-styrene, by themselves or in admixture with fibrous fillers (in some cases also blended with bitumen), or foamed polyvinyl chlorides or polystyrenes as insulating materials against heat and cold.
In practice, biocides are often used in conjunction with other biocides. In the process of this invention too it is possible to use further biocides. Combinations of biocides are also useful in antifouling compositions. Hence the phosphonium chlorides of formula ~, in conjunction with, for example, Cu20, CuSCN, zinc oxide, triorganotin compaunds, such as tributyltin fluoride, triphenyltin chloride or tributyltin-containing polymers, metallic copper or triazines such as 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine, can normally be combined with such compounds which are known to those skilled in the art as being effective against animal or vegetable growth.
It will be furthermore be readily underst()od that these combinations may additionally contain the substances and auxiliaries which are customarily concurrently used in such formulations. These additional substances include anionic, cationic or nonionic surfactants, electrolytes, chelating agents, solubilisers as well as dyes and aromatic substances. These ingredients are used typically to enhance the wetting capacity and hardening stability, to adjust the viscosity, and to enhance cold resistance.
The invention also relates to a process in which at least one further biocide is addded.
A particular advantage of the compounds is that their broad activity spectrum is achieved without the presence of a metal atom. Compared with the use of metal-containing biocides, the use of the biocides in the practice of this invention is ecologically more favourable.
As mentioned at the outset, in contrast to the corresponding tetrafluoroborates ordinarily used in non-aqueous materials, the alkyltributylphosphonium chlorides are hygroscopic.
They can therefore be incorporated without difficulty in aqueous systems. Their 7~13 incorporation in solvent-based paints, antit`ouling paints, coating compositions for surface protection or in polymer articles such as roofing memb~anes, rubber balls and the like, was therefore previously not known. Surprisingly, the process of this invention makes it possible to incorporate the compounds in such non-aqueous organic systems. It isespecially surprising that the, despite their very ~good aqueous solubility, the biocides cannot be dissolved, or can be dissolved only to an insignificant extent, out of these materials.
The following Examples illustrate the invention in more detail. In particular, they demonstrate the good effectiveness of the compounds of formula I in non-aqueous systems. In these Examples, and also throughout the description and in the claims, parts and percentages are by weight, unless othwerwise indicated.
Example 1: Tri-n-butyltetradecylphosphonium chloride is dissolved in xylene to give a 50 % solution, which is used to prepare an antifouling formulation based on vinyl/colophonium (1:1) and 20 % of fillèr in the manner known to those skilled in the art.
The amount of phosphonium compound is computed such that it comprises 22 % by weight in the dry film. The antifouling formulation is applied to microscopic slides conventionally llsed in microscopy. After drying for 3 days, one of these samples is kept for 1 week in artifical seawàter. After this time, this sample and a sample which has not been kepî in water are analysed. Analysis is made by 3IP-NMR spectroscopy. This is done by scratching off the coatings and weighing the scrapings. After the addition oftriphenylphosphine as internal standard, deuterised chloroform is added and the batch is ultrasonicated for 3 hours. After separation of the solids by centrifugation, a 31P-NMR spectrum of the solution is recorded, accumulating 42 000 scans. Correction factors for the peaks are determined by way of a quantitative inverse-gated image. The following analytical values are obtained:
concentration of tributyltetradecylphosphonium chloride in the sample which has not been kept in water: 20 %
concentration of tributyltetradecylphosphonium chloride in the sample which has been kept in water: 22 %
The analysis shows that the phosphonium compound has not leached out after immersion for 1 week in water. A less than the theoretical percentage concentration is found in the sample which has not been immersed in water. The explanation of this finding is that the solvents have not yet volatilised completely prior to immersion in water, thereby resulting in a higher "dilution" results.
A t S1~3 Example 2: Tributyltetradecylphosphonium chloridle is added to a commercially available wood sealing varnish ("Classic" filler-free varnish, ex Decor GmbH, Hamburg) such that the liquid formulation contains 3 % of the compound. The formulation is applied, stored and analysed as described in Example 1. The following analytical values are obtained:
concentration of tributyltetradecylphosphonium chloride in the sample which has not been kept in water: 11 %
concentration of tributyltetradecylphosphonium chloride in the sample which has been kept in water for 1 week: 8 %
Example 3: The antifouling paint formulation of Example 1 is applied to specimen plates to test the growth resistance to seawater organisms. Plates coated with the biocidally-treated paint formulation are free from growth after immersion for 12 and 39 weeks in the North Sea. Plates coated with the same formulation, but without biocide, are completely overgrown even after immersion for 12 weeks.
The paints (paint formulations) to be protected are preferably antifouling paints. These paints contain as binder the customary polymers known to those skilled in the art, typically natural and synthetic resins, homopolymers and copolymers of the monomers vinyl chloride, vinylidene chloride, styrene, vinyl toluene, vinyl esters, vinyl alcohols, acrylic acid and methacrylic acid, as well as their esters, polyester and polyamide resins, and also chlorinated rubber, natural and synthetic rubber, which may be chlorinated or cyclised, also reaction resins such as epoxy resins, polyurethane resins, unsaturated polyesters which may be converted into film-forming products of high molecular weight by adding hardeners.
The binders may be liquid or in the form of solutions. Solid coating compositions can be applied to objects by powder coating techniques. Other conventional basic components are typically tar, modifiers, dyes, inorganic or organic pigments, fillers and hardeners.
The process of this invention is utilised especially wherever objects which it is desired to protect against the growth of fungi arld algae and infestation by balanidae, bryozoa, hydroida, molluscs, protozoa, mussels and bacteria are exposed to water, especially seawater. Such objects are in particular ships' hulls, hydraulic structures, buoys or f1shing nets, and also cooling and pipe systems around or through which water flows. Quite generally the process of this invention makes it possible to protect all materials which can come in contact with water from growth or infestation by the cited organisms.
Accordingly, a preferred process is one wherein the compounds of formula I are used in antifouling paints.
A preferred process is also one wherein the compounds of forrnula I are used in paint formulations for objects which are submerged in water, especially seawater.
The amount of compounds of formula I which is used and added to the industrial materials in the process of this invention will naturally depend sobstantially on the respective utility and can therefore vary over a wide range. Depending on the envisaged end use, the compounds are used in the concentration ranges which are known to those skilled in the art.
Owing to the wide spectrum of use, concentrations of 0.1 to 40 % by weight of cornpound of formola I, based on the substrate to be treated, are suitable. Typical concentrations for treating plastics materials, such as plasdcised PVC sheets, are 0.1 to 10 % by weight, preferably 0.1 to 5 % by weight; 0.1 to 40 % by weight, preferably 0.5 to 40 % by weight, for example 10 to 40 by weight, in paint formulations such as antifouling paints.
A preferred field of use is that for protective coatings, especially for antifouling paints, to which are added, besides conventional basic and modifier components, typically 0.5 to 40 % by weight, preferably 5 to 40 % by weight, based on the total mixture, of at least one compound of formula I.
The compounds of formula I, which are dissolved in organic solvents, can be applied in pure form or together with carriers such as formuladon auxiliaries. They can also be suspended in liquid coating composidons and the like, in which case wetting agents can promote the uniform dispersion of the active compound to form homogeneous dispersions.
Further biocides may also be added.
A further utility of the compounds of formula I is incorporation in plastics materials, including polyvinyl chlorides and their co- and heteropolymers, polyalkylenes, including polyisobutylene, polyacrylates, polystyrenes, copolymers thereof, polyurethanes or polyisocyanates, polyesters, epoxy resins and the like, or in natural or synthetic rubbers.
The process of the invention can be used with advantage for providing plastics materials, including polyamides, polyurethane foams or polyisobutylene, with preservative finishes.
When using plasticisers, it is best to add a solution or dispersion of the biocide in the plasdciser to the plastics material. The antimicrobially treated pLIstics materials can be used for fabricating useful articles of all kinds for which effective protection against the most diverse germs, such as bacteria and fungi, is desired, for example plasticised PVC
sheets, foot-mats, bathroom curtains, seats, swimming pool steps, wall coverings and the like.
The compounds of formula I can also be used for elastomer coatings as well as for silicone elastomers and fluorine-containing polymers. In this connection it is expedient to use preferably high-boiling solvents, which in some cases remain in the finished product.
~g~3~75~3 A particularly advantageolls utility is incorporation in plastics or polymer materials which are used as building materials and are exposed to atmospheric influences, or which are used in the humid and moist sectors. Such materials may typically be rooflng materials or facings of polyvinyl chloride, butyl rubber, chlorinated polyethylene, polyisobutylene, chloroprene and chloroisoprene, ~PDM as well as PVC copolymers with vinyl acetate or ethyl vinyl acetate, polyacrylonitrile-styrene, by themselves or in admixture with fibrous fillers (in some cases also blended with bitumen), or foamed polyvinyl chlorides or polystyrenes as insulating materials against heat and cold.
In practice, biocides are often used in conjunction with other biocides. In the process of this invention too it is possible to use further biocides. Combinations of biocides are also useful in antifouling compositions. Hence the phosphonium chlorides of formula ~, in conjunction with, for example, Cu20, CuSCN, zinc oxide, triorganotin compaunds, such as tributyltin fluoride, triphenyltin chloride or tributyltin-containing polymers, metallic copper or triazines such as 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine, can normally be combined with such compounds which are known to those skilled in the art as being effective against animal or vegetable growth.
It will be furthermore be readily underst()od that these combinations may additionally contain the substances and auxiliaries which are customarily concurrently used in such formulations. These additional substances include anionic, cationic or nonionic surfactants, electrolytes, chelating agents, solubilisers as well as dyes and aromatic substances. These ingredients are used typically to enhance the wetting capacity and hardening stability, to adjust the viscosity, and to enhance cold resistance.
The invention also relates to a process in which at least one further biocide is addded.
A particular advantage of the compounds is that their broad activity spectrum is achieved without the presence of a metal atom. Compared with the use of metal-containing biocides, the use of the biocides in the practice of this invention is ecologically more favourable.
As mentioned at the outset, in contrast to the corresponding tetrafluoroborates ordinarily used in non-aqueous materials, the alkyltributylphosphonium chlorides are hygroscopic.
They can therefore be incorporated without difficulty in aqueous systems. Their 7~13 incorporation in solvent-based paints, antit`ouling paints, coating compositions for surface protection or in polymer articles such as roofing memb~anes, rubber balls and the like, was therefore previously not known. Surprisingly, the process of this invention makes it possible to incorporate the compounds in such non-aqueous organic systems. It isespecially surprising that the, despite their very ~good aqueous solubility, the biocides cannot be dissolved, or can be dissolved only to an insignificant extent, out of these materials.
The following Examples illustrate the invention in more detail. In particular, they demonstrate the good effectiveness of the compounds of formula I in non-aqueous systems. In these Examples, and also throughout the description and in the claims, parts and percentages are by weight, unless othwerwise indicated.
Example 1: Tri-n-butyltetradecylphosphonium chloride is dissolved in xylene to give a 50 % solution, which is used to prepare an antifouling formulation based on vinyl/colophonium (1:1) and 20 % of fillèr in the manner known to those skilled in the art.
The amount of phosphonium compound is computed such that it comprises 22 % by weight in the dry film. The antifouling formulation is applied to microscopic slides conventionally llsed in microscopy. After drying for 3 days, one of these samples is kept for 1 week in artifical seawàter. After this time, this sample and a sample which has not been kepî in water are analysed. Analysis is made by 3IP-NMR spectroscopy. This is done by scratching off the coatings and weighing the scrapings. After the addition oftriphenylphosphine as internal standard, deuterised chloroform is added and the batch is ultrasonicated for 3 hours. After separation of the solids by centrifugation, a 31P-NMR spectrum of the solution is recorded, accumulating 42 000 scans. Correction factors for the peaks are determined by way of a quantitative inverse-gated image. The following analytical values are obtained:
concentration of tributyltetradecylphosphonium chloride in the sample which has not been kept in water: 20 %
concentration of tributyltetradecylphosphonium chloride in the sample which has been kept in water: 22 %
The analysis shows that the phosphonium compound has not leached out after immersion for 1 week in water. A less than the theoretical percentage concentration is found in the sample which has not been immersed in water. The explanation of this finding is that the solvents have not yet volatilised completely prior to immersion in water, thereby resulting in a higher "dilution" results.
A t S1~3 Example 2: Tributyltetradecylphosphonium chloridle is added to a commercially available wood sealing varnish ("Classic" filler-free varnish, ex Decor GmbH, Hamburg) such that the liquid formulation contains 3 % of the compound. The formulation is applied, stored and analysed as described in Example 1. The following analytical values are obtained:
concentration of tributyltetradecylphosphonium chloride in the sample which has not been kept in water: 11 %
concentration of tributyltetradecylphosphonium chloride in the sample which has been kept in water for 1 week: 8 %
Example 3: The antifouling paint formulation of Example 1 is applied to specimen plates to test the growth resistance to seawater organisms. Plates coated with the biocidally-treated paint formulation are free from growth after immersion for 12 and 39 weeks in the North Sea. Plates coated with the same formulation, but without biocide, are completely overgrown even after immersion for 12 weeks.
Claims (14)
- What is claimed is:
l. A process for stabilising non-aqueous and water-insoluble industrial materials against attack by harmful organisms, which comprises incorporating in the system to be stabilised an effective amount of a phosphonium chloride of formula I
(C4H9)3 P CnH2n+1?Cl?(I) wherein n is an integer from 8 to 16. - 2. A process according to claim 1, wherein the compound of formula 1 is used in an amount of 0.1 to 40 % by weight, based on the material to be protected.
- 3. A process according to claim 2, wherein the compound of formula 1 is used in an amount of 0.5 to 40 % by weight, based on the material to be protected.
- 4. A process according to claim 1, which comprises adding a further biocide in addition to a compound of formula 1.
- 5. A process according to claim l, wherein n is an integer from 12 to 14..
- 6. A process according to claim l, wherein the non-aqueous system is a plastics material or a paint formulation.
- 7. A process according to claim 6, wherein the paint formulation is an exterior paint formulation.
- 8. A process according to claim 6, wherein the paint formulation is an antifouling paint formulation.
- 9. A process according to claim 6, wherein the paint formulation is a paint formulation for objects which are submerged in water.
- 10. A process according to claim 8, wherein the compound of formula I is added to the antifouling paint formulation in an amount of 0.5 to 40 % by weight.
- 11. A process according to claim 1, wherein the compound of formula 1, dissolved in an organic solvent, is incorporated in the material to be stabilised.
- 12. A process according to claim 11, wherein the solvent is selected from the group consisting of aromatic hydrocarbons, high-boiling mineral oils, ketones, esters and polyglycols.
- 13. A process according to claim 12, wherein the solvent is toluene or xylene, preferably toluene.
- 14. A process according to claim 11, wherein the compounds of formula I are dissolved in the organic solvent to give a 40-70 % by weight solution.
FD 4.2/WEI/RSU
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3472/91-4 | 1991-11-27 | ||
| CH347291 | 1991-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2083768A1 true CA2083768A1 (en) | 1993-05-28 |
Family
ID=4256705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2083768 Abandoned CA2083768A1 (en) | 1991-11-27 | 1992-11-25 | Protection of non-aqueous systems with biocides |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0544619A1 (en) |
| JP (1) | JPH05271022A (en) |
| CA (1) | CA2083768A1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281365A (en) * | 1963-12-23 | 1966-10-25 | Monsanto Co | Antiseptic detergent compositions |
| SE356307B (en) * | 1966-12-19 | 1973-05-21 | Aminkemi Ab | |
| DE3367719D1 (en) * | 1982-10-06 | 1987-01-08 | Ciba Geigy Ag | Biocidally active mixture |
| EP0235388B1 (en) * | 1985-12-28 | 1989-11-08 | MITSUI TOATSU CHEMICALS, Inc. | Preparation process of heat-resistant polymers |
| DE3737496A1 (en) * | 1987-11-05 | 1989-05-18 | Hoechst Ag | METHOD FOR INCREASING THE ELECTROSTATIC RECHARGEABILITY OF POWDER VARNISHES AND POWDERS AND THEIR USE FOR SURFACE COATING OF FIXED OBJECTS |
| ES2052961T3 (en) * | 1988-03-08 | 1994-07-16 | Ciba Geigy Ag | PHOSPHONE COMPOUNDS WITH BIOCIDAL ACTIVITY. |
-
1992
- 1992-11-18 EP EP92810899A patent/EP0544619A1/en not_active Withdrawn
- 1992-11-25 CA CA 2083768 patent/CA2083768A1/en not_active Abandoned
- 1992-11-27 JP JP34165592A patent/JPH05271022A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05271022A (en) | 1993-10-19 |
| EP0544619A1 (en) | 1993-06-02 |
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