DK165960B - Antimikrobiel phenoxyarsinoploesning, kunstofmateriale indeholdende oploesningen samt fremgangsmaader til fremstilling af den antimikrobielle phenoxyarsinoploesning og kunstofmaterialet - Google Patents
Antimikrobiel phenoxyarsinoploesning, kunstofmateriale indeholdende oploesningen samt fremgangsmaader til fremstilling af den antimikrobielle phenoxyarsinoploesning og kunstofmaterialet Download PDFInfo
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- DK165960B DK165960B DK530384A DK530384A DK165960B DK 165960 B DK165960 B DK 165960B DK 530384 A DK530384 A DK 530384A DK 530384 A DK530384 A DK 530384A DK 165960 B DK165960 B DK 165960B
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- phenoxyarsin
- antimicrobial
- phenoxyarsine
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 14
- VYKJIKQKGQORET-UHFFFAOYSA-N phenoxyarsane Chemical compound [AsH2]OC1=CC=CC=C1 VYKJIKQKGQORET-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 239000012237 artificial material Substances 0.000 title 2
- 239000002904 solvent Substances 0.000 claims abstract description 22
- AVKUWNUBPFREQI-UHFFFAOYSA-N phenoxyarsenic Chemical compound [As]OC1=CC=CC=C1 AVKUWNUBPFREQI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004014 plasticizer Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- VCRZAKVGPJFABU-UHFFFAOYSA-N 10-phenoxarsinin-10-yloxyphenoxarsinine Chemical group C12=CC=CC=C2OC2=CC=CC=C2[As]1O[As]1C2=CC=CC=C2OC2=CC=CC=C21 VCRZAKVGPJFABU-UHFFFAOYSA-N 0.000 claims description 12
- 229920003023 plastic Polymers 0.000 claims description 12
- 239000004033 plastic Substances 0.000 claims description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 9
- 101100188540 Candida albicans (strain SC5314 / ATCC MYA-2876) OBPA gene Proteins 0.000 claims description 7
- 239000004599 antimicrobial Substances 0.000 claims description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229920003002 synthetic resin Polymers 0.000 claims description 6
- 239000000057 synthetic resin Substances 0.000 claims description 6
- 238000010348 incorporation Methods 0.000 claims description 5
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 5
- 239000004800 polyvinyl chloride Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical group OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- YJOMWQQKPKLUBO-UHFFFAOYSA-L lead(2+);phthalate Chemical compound [Pb+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O YJOMWQQKPKLUBO-UHFFFAOYSA-L 0.000 claims 1
- SJOCPYUKFOTDAN-ZSOIEALJSA-N methyl (4z)-4-hydroxyimino-6,6-dimethyl-3-methylsulfanyl-5,7-dihydro-2-benzothiophene-1-carboxylate Chemical compound C1C(C)(C)C\C(=N\O)C=2C1=C(C(=O)OC)SC=2SC SJOCPYUKFOTDAN-ZSOIEALJSA-N 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000012141 concentrate Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- AIMXDOGPMWDCDF-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1CCCCC1 AIMXDOGPMWDCDF-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-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
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- RAPJXFPEGPHCSJ-UHFFFAOYSA-N dihydroxyphosphanyl 2-aminoacetate prop-1-ene Chemical compound CC=C.CC=C.NCC(=O)OP(O)O RAPJXFPEGPHCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08K5/59—Arsenic- or antimony-containing compounds
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0058—Biocides
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
i
DK 165960B
Den foreliggende opfindelse angår antimikrobielle blandinger egnede til inkorporering i kunststoffer, idet der ved virkningsangivelsen "antimikrobiel” især også skal forstås fungistatisk eller fungicid virkning.
5 Det er kendt at beskytte kunstharpiksmaterialer mod antimikrobielle påvirkninger ved, at man i disse materialer inkorporerer antimikrobielle aktivstoffer. Det er især kendt at inkorporere phenoxyarsiner, fx 10,10'-oxybisphenozyarsin, som antimikrobielt middel i disse kunstharpiksmaterialer. Dette udføres sædvanligvis ved, at der ved 10 fremstillingen-af disse kunstharpiksmaterialer, fx ved fremstilling af vinylharpikser såsom polyvinylchlorid, til de anvendte blødgø-ringsmidler sættes en opløsning af phenoxyarsinen. Til dette formål har der været foreslået forskellige opløsningsmidler for phenoxyarsinen, fx phenoler og aliphatiske alkoholer såsom nonylphenol og visse 15 phosphiter og phosphonater såsom tris(dipropylenglycyl)phosphit (USA patentskrift nr. 3.288.674). Disse opløsningsmidler har imidlertid i forskellig henseende til dels væsentlige ulemper, nemlig: dårlig opløsningsevne ved stuetemperatur, - høj viskositet og dermed forbundne vanskeligheder ved forarbejd- 20 ningen, - lugtgener, lave kogepunkter, utilfredsstillende blandbarhed med de i kunststofindustrien sædvanligvis anvendte blødgøringsmidler, 25 - ugunstige toxicologiske egenskaber.
Formålet med den foreliggende opfindelse er at tilvejebringe antimikrobielle blandinger, som er egnede til inkorporering i kunststoffer, hvilke blandinger indeholder en phenoxyarsin som antimikrobielt middel og et opløsningsmiddel for den anvendte phenoxyarsin og ikke 30 har de ulemper, som er betingede af de hidtil anvendte opløsningsmidler.
Dette formål opfyldes ifølge opfindelsen ved anvendelse af et opløsningsmiddel med den almene formel I
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2 føV0*- (CH2>n0H X.
R2 R3 hvor R^, R2 og R3 betegner hydrogen eller lavere alkyl (C^.y), 5 m betegner 0 eller 1, og n betegner 1 eller 2.
Et aspekt af den foreliggende opfindelse angår således en antimikro-biel blanding, som er egnet til inkorporering i kunststoffer, hvilken blanding indeholder en phenoxyarsin som antimikrobielt middel og et 10 opløsningsmiddel, og denne blanding er ejendommelig ved, at opløsningsmidlet ér en forbindelse med den ovenfor angivne formel I.
Foretrukne eksempler på forbindelser med den almene formel I er benzylalkohol, 2-phenylethanol og 2-phenoxyethanol, hvoraf benzyl-alkohol er sarlig foretrukken.
15 Andre eksempler på forbindelser med den almene formel I er sådanne, hvor Rjl, R2 og R3 hver betegner en butylgruppe, dvs. tributylsubsti-tuterede forbindelser med den almene formel I.
Som phenoxyarsiner kommer alle phenoxyarsiner, som sædvanligvis anvendes til at give kunststoffer antimikrobielle egenskaber, i 20 betragtning, fx de i USA patentskrift nr. 3.689.449 og nr. 4.049.822 nævnte. En særlig foretrukken phenoxyarsin er 10,10'-oxybisphenoxyar-sin.
En sådan opløsning, som indeholder en phenoxyarsin, isar den nævnte 10,10'-oxybisphenoxyarsin, og et opløsningsmiddel med den almene
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3 formel I, har sædvanligvis et indhold på ca. 10 - ca. 50 vægtprocent phenoxyarsin, fx et indhold på 20-30 vægtprocent phenoxyarsin.
Et yderligere aspekt af den foreliggende opfindelse angår en sammensætning, som ud over phenoxyarsinen og opløsningsmidlet indeholder 5 yderligere mindst, ét blødgøringsmiddel. Med en sådan sammensætning inkorporeres sædvanligvis phenoxyarsinen og blødgøringsmidlet i kunstharpiksmaterialet. En sådan sammensætning fås fx ved blanding af en 20%'s stamopløsning (20%'s opløsning af phenoxyarsin i et opløsningsmiddel med den almene formel I) med et blødgøringsmiddel, hvor- 10 ved der vindes et produkt, som indeholder ca. 1-2 vægtprocent phenoxyarsin beregnet på grundlag af den samlede masse af blødgøringsmiddel, opløsningsmiddel og phenoxyarsin. Sådanne sammensætninger anvendes i kuns tstof forarbejdningsindustrien til at give folier, gulvbelægninger, vægbeklædninger, brusebads forhæng, bademåtter, 15 dørhåndtag, håndgelændere på trapper, rørbandager, etc. antimikrobi-elle egenskaber. Sådanne sammensætninger kan på sædvanligt maskineri let indarbejdes i de pågældende kunststoffer, idet der også ved fx polyvinylchloridprodukter tåles de sædvanlige forarbejdningstempera-turer på op til ca. 180*C.
20 Som blødgøringsmidler kommer især følgende stoffer i betragtning: estere af polybasiske syrer (såsom phthalsyre, adipinsyre, trimellithsyre og sebacinsyre) med monovalente alkoholer (såsom ethylhexyalkanol, isodecylalkohol og isotridecylalkohol) med en molekylvægt på fra ca. 250 til ca. 500, 25 - polyestere af glycoler (såsom 1,2-propylenglycol og neopentyl- glycol) med dibasiske syrer (såsom adipinsyre og sebacinsyre) med en molekylvægt på fra ca. 600 til ca. 1200, epoxiderede plantefrøolier (såsom sojaepoxid og ricinusolie-epoxid), 30 - phosphorsyreestere (såsom tricresylphosphat og tri-2-ethylhexyl- phosphat).
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4
Som kunstharpikser kommer især vinylharpikser i betragtning, nemlig homopolymerer af vinylchlorid fremstillet ved emulsions -, suspensions- eller massepolymerisation og copolymerer af vinylchlorid med vinylacetat, maleinsyre, vinylidenchlorid, acrylnitril osv. frem-5 stillet ved emulsions- eller suspensionspolymerisation og ved podepolymerisation.
Et foretrukkent kunstharpiksmateriale er polyvinylchlorid.
Et yderligere aspekt af den foreliggende opfindelse angår således et kunstharpiksmateriale, især et polyvinylchloridmateirale, som frem-10 stilles under anvendelse af én af de ovenfor angivne blandinger.
Den foreliggende opfindelse angår endvidere en fremgangsmåde til fremstilling af en antimikrobiel blanding, som er egnet til inkorporering i kunststoffer, hvilken fremgangsmåde er ejendommelig ved, at en phenoxyarsin, især 10,10'-oxybisphenoxyarsin, opløses i et 15 opløsningsmiddel med den ovenfor angivne almene formel I, den vundne opløsning indarbejdes i et blødgøringsmiddel, og den vundne blød-gøringsmiddelblanding anvendes ved fremstillingen af kunstharpiksma-terialet. Sådanne blødgøringsmiddelblandinger kan yderligere indeholde antioxidanter fx sterisk hindrede phenoler såsom 20 2,6-ditert.butyl-p-cresol, aminforbindelser såsom N,N'-dicyclohexyl-p-phenylendiamin og svovl(II)-forbindelser såsom thiodipropionsyredilaurylester. De under anvendelse af sådanne blød-gøringsmiddelblandinger fremstillede kunstharpiksmaterialer kan yderligere indeholde smøremidler såsom metalsæber (fx calciumstearat 25 og zinkstearat) eller voksarter (fx camaubavoks). Sådanne blødgø- ringsmiddelblandinger kan udgøre ca. 1,5% (ved et phenoxyarsinindhold på 2%) eller 3% (ved et phenoxyarsinindhold på 1%) af polyvinyl-chloridblandingerne, beregnet på basis af vinylsystemet.
EKSEMPEL 1 30 I de følgende tabeller er der angivet forskellige koncentrater af 10,10'-oxybisphenoxyarsin (OBPA) med forskellige opløsningsmidler, og den nødvendige minimumstemperatur til opløsning af OBPA er angivet (R.T = stuetemperatur).
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5 TABEL 1
Bestanddel Koncentrater (vægtprocent)
ABC
5 OBPA 20 20 20
Benzylalkohol 80 2-Phenylethanol 80 2-Phenoxye thano1 80 10 Opløsnings temperatur, °C RT 50 150
Koncentraterne A, B og C er frostsikre og kan lagres i egnede beholdere i praktisk talt ubegrænset tid.
EKSEMPEL 2 15 De i tabel 1 anførte koncentrater A, B og C blandes ved stuetemperatur med forskellige blødgøringsmidler, hvorved der fås handelsprodukter med et indhold på 1 eller 2 vægtprocent OBPA. I tabel 2 er de således vundne blandinger angivet.
TABEL 2 20 Bestandele Produkter (vægtprocent)
ABCDEFGHJ KLM
Koncentrat A 5 10 5 10 B 5 10 5 10 25 C 5 10 5 10
Diisodecylphthalat 95 95 95 90 90 90 Eåpxoderet sojaolie 95 95 95 90 90 90 OBPA-Indhold 111222 111222
Claims (12)
1. Antimikrobiel blanding egnet til inkorporering i kunststoffer, hvilken blanding indeholder en phenoxyarsin som antimikrobielt middel og et opløsningsmiddel, kendetegnet ved, at opløsningsmidlet er en forbindelse med den almene formel I DK 165960 B R1 <CH2>n0H R2 i R3 hvor Rj_, R2 og R3 betegner hydrogen eller lavere alkyl (C^_7), 5. betegner 0 eller 1, og n betegner 1 eller 2.
2. Blanding ifølge krav 1, kendetegnet ved, at opløsningsmidlet er benzylalkohol.
3. Blanding ifølge krav 1, 10 kendetegnet ved, at opløsningsmidlet er 2-phenylethanol.
4. Blanding ifølge krav 1, kendetegnet ved, at opløsningsmidlet er 2-phenoxyethanol.
5. Blanding ifølge et hvilket som helst af kravene 1-4, kendetegnet ved, at phenoxyarsinen er 10,10'-oxybis- 15 phenoxyarsin.
6. Blanding ifølge et hvilket som helst af kravene 1-5, kendetegnet ved, at den indeholder mindst 10%, fortrinsvis 20-30% phenoxyarsin.
7. Blanding ifølge et hvilket som helst af kravene 1-6, 20 kendetegnet ved, at den yderligere indeholder et blød-gøringsmiddel. DK 165960 B
8. Kunststofmateriale, kendetegnet ved, at det er fremstillet under anvendelse af en blanding ifølge et hvilket som helst af kravene 1-7.
9. Kunststofmateriale ifølge krav 8, 5 kendetegnet ved, at kunstharpiksen er et polyvinylchlorid.
10. Fremgangsmåde til fremstilling af en blanding ifølge et hvilket som helst af kravene 1-7, kendetegnet ved, at en phenoxyarsin opløses i et opløsningsmiddel med den almene formel I ifølge krav 1, og denne opløsning 10 eventuelt indarbejdes i et blødgøringsmiddel.
10 Blødgøringsmiddelblanding ifølge opfindelsen (2% OBPA) 1,50 Andre blødgøringsmidler 27,90 Antioxidant 0,05 Burgess-ler 8,60
15 Dibasisk blyphthalat 3,50 Dibasisk blystearat 0,60 Smøremiddel 0,30 100,0
20 Ved "blødgøringsmiddelblanding" skal der her forstås et af produkterne A-M i tabel 2. På denne måde får vinylblandingen et indhold på 0,03% eller 300 ppm OBPA. hvilket er tilstrækkeligt til at give antimikrobiel beskyttelsesvirkning.
11. Fremgangsmåde til fremstilling af et kunststofmateriale ifølge krav 8 eller 9, kendetegnet ved, at en phenoxyarsin opløses i et opløsningsmiddel med den almene formel I ifølge krav 1, den vundne op-15 løsning indarbejdes i et blødgøringsmiddel, og dette anvendes ved fremstilling af kunststofmaterialet.
12. Anvendelsen af en forbindelse med den almene formel I ifølge krav 1 som opløsningsmiddel for phenoxyarsin, især for 10,10'-oxybis-phenoxyar s in.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH618483 | 1983-11-17 | ||
| CH618483 | 1983-11-17 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK530384D0 DK530384D0 (da) | 1984-11-07 |
| DK530384A DK530384A (da) | 1985-05-18 |
| DK165960B true DK165960B (da) | 1993-02-22 |
| DK165960C DK165960C (da) | 1993-07-26 |
Family
ID=4305584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK530384A DK165960C (da) | 1983-11-17 | 1984-11-07 | Antimikrobiel phenoxyarsinoploesning, kunstofmateriale indeholdende oploesningen samt fremgangsmaader til fremstilling af den antimikrobielle phenoxyarsinoploesning og kunstofmaterialet |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5488065A (da) |
| EP (1) | EP0144726B2 (da) |
| JP (1) | JPS60116614A (da) |
| AT (1) | ATE43471T1 (da) |
| CA (1) | CA1232706A (da) |
| DE (1) | DE3478387D1 (da) |
| DK (1) | DK165960C (da) |
| NO (1) | NO164574C (da) |
| ZA (1) | ZA848714B (da) |
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| EP0144726B2 (de) * | 1983-11-17 | 1995-05-24 | Akzo Nobel N.V. | Antimikrobielle Mischungen |
| US4663077A (en) * | 1984-06-11 | 1987-05-05 | Morton Thiokol Inc. | Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein |
| US4683080A (en) * | 1984-06-11 | 1987-07-28 | Morton Thiokol, Inc. | Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein |
| US4624679A (en) * | 1985-01-03 | 1986-11-25 | Morton Thiokol, Inc. | Compositions containing antimicorbial agents in combination with stabilizers |
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| CA2037282C (en) * | 1990-04-02 | 1997-01-28 | Nuno M. Rei | Microbicides immobilized in water-soluble thermoplastic polymeric resins and aqueous dispersions of microbicides prepared therefrom |
| US5554373A (en) * | 1993-11-05 | 1996-09-10 | Seabrook; Samuel G. | Compositions containing anti-microbial agents and methods for making and using same |
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| US6627676B1 (en) | 1999-08-27 | 2003-09-30 | Richard George | Antimicrobial biocidic fiber-plastic composite and method of making same |
| US6444737B1 (en) | 2000-04-05 | 2002-09-03 | 3M Innovative Properties Company | Water-dispersed polymer stabilizer |
| CA2463908A1 (en) * | 2001-10-18 | 2003-04-24 | Bristol-Myers Squibb Company | Human glucagon-like-peptide-1 mimics and their use in the treatment of diabetes and related conditions |
| ES2372979T3 (es) | 2003-02-12 | 2012-01-30 | The Procter & Gamble Company | Núcleo absorbente para un artículo absorbente. |
| EP1813236B1 (en) | 2003-02-12 | 2013-07-10 | The Procter & Gamble Company | Absorbent Core for an Absorbent Article |
| US7323044B1 (en) | 2007-01-22 | 2008-01-29 | Troy Corporation | Biocidal compositions |
| PL2478883T3 (pl) | 2007-06-18 | 2017-01-31 | The Procter And Gamble Company | Jednorazowy wyrób chłonny z zasadniczo rozmieszczonym w sposób ciągły chłonnym rozdrobnionym materiałem polimerowym oraz sposób jego wytwarzania |
| MX2009013906A (es) | 2007-06-18 | 2010-01-28 | Procter & Gamble | Articulo absorbente desechable con nucleo absorbente sellado con material polimerico particulado absorbente practicamente distribuido en forma continua. |
| CN102014826A (zh) | 2008-04-29 | 2011-04-13 | 宝洁公司 | 制造具有抗应变芯覆盖件的吸收芯的方法 |
| EP2329803B1 (en) | 2009-12-02 | 2019-06-19 | The Procter & Gamble Company | Apparatus and method for transferring particulate material |
| EP2532329B1 (en) | 2011-06-10 | 2018-09-19 | The Procter and Gamble Company | Method and apparatus for making absorbent structures with absorbent material |
| RU2013156991A (ru) | 2011-06-10 | 2015-07-20 | Дзе Проктер Энд Гэмбл Компани | Абсорбирующая сердцевина для одноразовых абсорбирующих изделий |
| EP2532328B1 (en) | 2011-06-10 | 2014-02-26 | The Procter and Gamble Company | Method and apparatus for making absorbent structures with absorbent material |
| CN106974772B (zh) | 2011-06-10 | 2021-01-12 | 宝洁公司 | 用于吸收制品的吸收结构 |
| DE202012013585U1 (de) | 2011-06-10 | 2018-01-17 | The Procter & Gamble Company | Einwegwindel |
| ES2484695T5 (es) | 2011-06-10 | 2018-02-13 | The Procter & Gamble Company | Pañal desechable que tiene una unión reducida entre el núcleo absorbente y la lámina de respaldo |
| EP3266432B1 (en) | 2011-06-10 | 2019-04-17 | The Procter & Gamble Company | Absorbent structure for absorbent articles |
| DE202013012607U1 (de) | 2012-11-13 | 2017-11-19 | The Procter & Gamble Company | Absorptionsartikel mit Kanälen und Signalen |
| US8979815B2 (en) | 2012-12-10 | 2015-03-17 | The Procter & Gamble Company | Absorbent articles with channels |
| US9216116B2 (en) | 2012-12-10 | 2015-12-22 | The Procter & Gamble Company | Absorbent articles with channels |
| PL2740449T3 (pl) | 2012-12-10 | 2019-07-31 | The Procter & Gamble Company | Artykuł chłonny o wysokiej zawartości materiału chłonnego |
| EP2740450A1 (en) | 2012-12-10 | 2014-06-11 | The Procter & Gamble Company | Absorbent core with high superabsorbent material content |
| PL2740452T3 (pl) | 2012-12-10 | 2022-01-31 | The Procter & Gamble Company | Wyrób chłonny o wysokiej zawartości materiału chłonnego |
| US10639215B2 (en) | 2012-12-10 | 2020-05-05 | The Procter & Gamble Company | Absorbent articles with channels and/or pockets |
| US9216118B2 (en) | 2012-12-10 | 2015-12-22 | The Procter & Gamble Company | Absorbent articles with channels and/or pockets |
| PL3254656T3 (pl) | 2013-06-14 | 2022-01-10 | The Procter & Gamble Company | Wyrób chłonny i wkład chłonny tworzący kanały w stanie mokrym |
| CN105473113B (zh) | 2013-08-27 | 2019-03-08 | 宝洁公司 | 具有通道的吸收制品 |
| US9987176B2 (en) | 2013-08-27 | 2018-06-05 | The Procter & Gamble Company | Absorbent articles with channels |
| US11207220B2 (en) | 2013-09-16 | 2021-12-28 | The Procter & Gamble Company | Absorbent articles with channels and signals |
| EP2851048B1 (en) | 2013-09-19 | 2018-09-05 | The Procter and Gamble Company | Absorbent cores having material free areas |
| US9789009B2 (en) | 2013-12-19 | 2017-10-17 | The Procter & Gamble Company | Absorbent articles having channel-forming areas and wetness indicator |
| EP2905001B1 (en) | 2014-02-11 | 2017-01-04 | The Procter and Gamble Company | Method and apparatus for making an absorbent structure comprising channels |
| EP2949300B1 (en) | 2014-05-27 | 2017-08-02 | The Procter and Gamble Company | Absorbent core with absorbent material pattern |
| US10507144B2 (en) | 2015-03-16 | 2019-12-17 | The Procter & Gamble Company | Absorbent articles with improved strength |
| BR112017024325A2 (pt) | 2015-05-12 | 2018-07-24 | Procter & Gamble | artigo absorvente com um adesivo aprimorado entre o núcleo e a camada inferior |
| JP6743057B2 (ja) | 2015-05-29 | 2020-08-19 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | チャネル及び湿り度インジケータを有する吸収性物品 |
| EP3167859B1 (en) | 2015-11-16 | 2020-05-06 | The Procter and Gamble Company | Absorbent cores having material free areas |
| EP3238676B1 (en) | 2016-04-29 | 2019-01-02 | The Procter and Gamble Company | Absorbent core with profiled distribution of absorbent material |
| EP3238678B1 (en) | 2016-04-29 | 2019-02-27 | The Procter and Gamble Company | Absorbent core with transversal folding lines |
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| US3228830A (en) * | 1962-11-05 | 1966-01-11 | Dow Chemical Co | Biocidally-active phenoxarsine-containing polymeric materials |
| US3288674A (en) * | 1965-03-15 | 1966-11-29 | Scient Chemicals Inc | Phenoxarsine compounds incorporated into resins with phenols |
| USRE29409E (en) * | 1965-03-15 | 1977-09-20 | Ventron Corporation | Phenoxarsine compounds incorporated into resins with phenols |
| GB1085970A (en) * | 1966-09-12 | 1967-10-04 | Scient Chemicals Inc | Vinyl resin compositions |
| US3544610A (en) * | 1969-01-23 | 1970-12-01 | Dow Chemical Co | Phenoxy- and substituted phenoxy-phenoxarsine compounds |
| US3660353A (en) * | 1970-04-01 | 1972-05-02 | Dow Chemical Co | Monomers and polymers of 10-(alkenyl) oxyphenoxarsines |
| US3636024A (en) * | 1970-05-04 | 1972-01-18 | Dow Chemical Co | Halogenated-10 10'-riphenoxarsines |
| US3689449A (en) * | 1971-04-01 | 1972-09-05 | Ventron Corp | Composition for imparting anti-bacterial characteristics to vinyl resins |
| US4049822A (en) * | 1975-08-04 | 1977-09-20 | Ventron Corporation | Microbiocidal compositions comprising a solution of a phenoxarsine compound |
| EP0144726B2 (de) * | 1983-11-17 | 1995-05-24 | Akzo Nobel N.V. | Antimikrobielle Mischungen |
| US4683080A (en) * | 1984-06-11 | 1987-07-28 | Morton Thiokol, Inc. | Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein |
-
1984
- 1984-11-02 EP EP84113170A patent/EP0144726B2/de not_active Expired - Lifetime
- 1984-11-02 DE DE8484113170T patent/DE3478387D1/de not_active Expired
- 1984-11-02 AT AT84113170T patent/ATE43471T1/de not_active IP Right Cessation
- 1984-11-07 DK DK530384A patent/DK165960C/da not_active IP Right Cessation
- 1984-11-07 ZA ZA848714A patent/ZA848714B/xx unknown
- 1984-11-07 CA CA000467210A patent/CA1232706A/en not_active Expired
- 1984-11-15 NO NO844569A patent/NO164574C/no not_active IP Right Cessation
- 1984-11-15 JP JP59241572A patent/JPS60116614A/ja active Granted
-
1986
- 1986-04-28 US US06/859,189 patent/US5488065A/en not_active Expired - Lifetime
-
1996
- 1996-01-25 US US08/591,326 patent/US5629342A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0144726B1 (de) | 1989-05-31 |
| EP0144726A2 (de) | 1985-06-19 |
| DK165960C (da) | 1993-07-26 |
| US5629342A (en) | 1997-05-13 |
| ZA848714B (en) | 1985-07-31 |
| JPS60116614A (ja) | 1985-06-24 |
| EP0144726A3 (en) | 1985-07-10 |
| NO164574B (no) | 1990-07-16 |
| DK530384D0 (da) | 1984-11-07 |
| EP0144726B2 (de) | 1995-05-24 |
| NO844569L (no) | 1985-05-20 |
| US5488065A (en) | 1996-01-30 |
| NO164574C (no) | 1990-10-24 |
| DK530384A (da) | 1985-05-18 |
| DE3478387D1 (en) | 1989-07-06 |
| CA1232706A (en) | 1988-02-16 |
| JPH0553765B2 (da) | 1993-08-10 |
| ATE43471T1 (de) | 1989-06-15 |
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