CA2329023C - Biocide-polyester concentrates and biocidal compositions prepared therefrom - Google Patents
Biocide-polyester concentrates and biocidal compositions prepared therefrom Download PDFInfo
- Publication number
- CA2329023C CA2329023C CA002329023A CA2329023A CA2329023C CA 2329023 C CA2329023 C CA 2329023C CA 002329023 A CA002329023 A CA 002329023A CA 2329023 A CA2329023 A CA 2329023A CA 2329023 C CA2329023 C CA 2329023C
- Authority
- CA
- Canada
- Prior art keywords
- biocide
- polyester
- weight
- acid
- concentrate according
- 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
- 229920000728 polyester Polymers 0.000 title claims abstract description 42
- 239000012141 concentrate Substances 0.000 title claims abstract description 40
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims description 23
- -1 polypropylene Polymers 0.000 claims abstract description 32
- 239000003139 biocide Substances 0.000 claims abstract description 22
- 238000002845 discoloration Methods 0.000 claims abstract description 15
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920000098 polyolefin Polymers 0.000 claims abstract description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 229920000307 polymer substrate Polymers 0.000 claims description 16
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 7
- 229920001634 Copolyester Polymers 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920006324 polyoxymethylene Polymers 0.000 claims description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 claims description 3
- HDHLIWCXDDZUFH-UHFFFAOYSA-N irgarol 1051 Chemical compound CC(C)(C)NC1=NC(SC)=NC(NC2CC2)=N1 HDHLIWCXDDZUFH-UHFFFAOYSA-N 0.000 claims description 3
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229940100890 silver compound Drugs 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- AVKUWNUBPFREQI-UHFFFAOYSA-N phenoxyarsenic Chemical compound [As]OC1=CC=CC=C1 AVKUWNUBPFREQI-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 abstract description 7
- 229920000573 polyethylene Polymers 0.000 abstract description 7
- 239000000843 powder Substances 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 abstract description 6
- 239000004743 Polypropylene Substances 0.000 abstract description 2
- 229920001155 polypropylene Polymers 0.000 abstract description 2
- 238000004383 yellowing Methods 0.000 abstract 1
- 235000008504 concentrate Nutrition 0.000 description 30
- 239000000126 substance Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229940093470 ethylene Drugs 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000004702 low-density polyethylene Substances 0.000 description 3
- 229940099514 low-density polyethylene Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 2
- 229920005629 polypropylene homopolymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 230000000087 stabilizing effect Effects 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
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- QBTHTNCUNBHSHN-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)phenyl]phenol Chemical compound OC1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)O)=CC(C=2C(=CC=CC=2)O)=C1 QBTHTNCUNBHSHN-UHFFFAOYSA-N 0.000 description 1
- ICPXIRMAMWRMAD-UHFFFAOYSA-N 2-[3-[2-[3-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=CC(OCCO)=CC=1C(C)(C)C1=CC=CC(OCCO)=C1 ICPXIRMAMWRMAD-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- PNJNLCNHYSWUPT-UHFFFAOYSA-N 2-methylpentane-1,4-diol Chemical compound CC(O)CC(C)CO PNJNLCNHYSWUPT-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- CDZMWAHBQLPCHD-UHFFFAOYSA-N 3-(4-carboxyphenyl)-1,1,3-trimethyl-2h-indene-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2C(C)(C)CC1(C)C1=CC=C(C(O)=O)C=C1 CDZMWAHBQLPCHD-UHFFFAOYSA-N 0.000 description 1
- UEDISDQWZXBSKK-UHFFFAOYSA-N 3-[4-[1-[4-(3-hydroxypropoxy)phenyl]ethyl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)C1=CC=C(OCCCO)C=C1 UEDISDQWZXBSKK-UHFFFAOYSA-N 0.000 description 1
- RBQLGIKHSXQZTB-UHFFFAOYSA-N 3-methylpentane-2,4-diol Chemical compound CC(O)C(C)C(C)O RBQLGIKHSXQZTB-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- OLZBOWFKDWDPKA-UHFFFAOYSA-N 4-[1-(4-carboxyphenyl)ethyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)C1=CC=C(C(O)=O)C=C1 OLZBOWFKDWDPKA-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 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
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 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
- 150000001880 copper compounds Chemical class 0.000 description 1
- WYHYNUWZLKTEEY-UHFFFAOYSA-N cyclobutane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C1 WYHYNUWZLKTEEY-UHFFFAOYSA-N 0.000 description 1
- LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-M phloretate Chemical compound OC1=CC=C(CCC([O-])=O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-M 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0058—Biocides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
- A01N25/08—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 solids as carriers or diluents
- A01N25/10—Macromolecular 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biodiversity & Conservation Biology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/467,809 US6475505B1 (en) | 1999-12-20 | 1999-12-20 | Biocide-polyester concentrates and biocidal compositions prepared therefrom |
| US09/467,809 | 1999-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2329023A1 CA2329023A1 (en) | 2001-06-20 |
| CA2329023C true CA2329023C (en) | 2008-07-29 |
Family
ID=23857274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002329023A Expired - Fee Related CA2329023C (en) | 1999-12-20 | 2000-12-18 | Biocide-polyester concentrates and biocidal compositions prepared therefrom |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6475505B1 (https=) |
| EP (1) | EP1114583B1 (https=) |
| JP (1) | JP2001172106A (https=) |
| KR (1) | KR100691538B1 (https=) |
| CN (1) | CN1190131C (https=) |
| AT (1) | ATE245348T1 (https=) |
| BR (1) | BR0005939A (https=) |
| CA (1) | CA2329023C (https=) |
| DE (1) | DE60004004T2 (https=) |
| DK (1) | DK1114583T3 (https=) |
| ES (1) | ES2202031T3 (https=) |
| PT (1) | PT1114583E (https=) |
| RU (1) | RU2258723C2 (https=) |
| TW (1) | TWI260969B (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ841900A0 (en) * | 2000-06-28 | 2000-07-20 | Unisearch Limited | Synthesis of cyclic compounds |
| WO2002055301A1 (de) * | 2001-01-10 | 2002-07-18 | Mitsubishi Polyester Film Gmbh | Antimikrobiell ausgerüstete, mehrschichtige polyesterfolie mit matter oberfläche |
| DE10258551A1 (de) * | 2001-12-22 | 2003-07-03 | Phoenix Ag | Klärbeckenmembran |
| US7166671B2 (en) | 2002-12-10 | 2007-01-23 | Cellresin Technologies, Llc | Grafted cyclodextrin |
| US8129450B2 (en) | 2002-12-10 | 2012-03-06 | Cellresin Technologies, Llc | Articles having a polymer grafted cyclodextrin |
| US7385004B2 (en) | 2002-12-10 | 2008-06-10 | Cellresin Technologies, Llc | Enhanced lubrication in polyolefin closure with polyolefin grafted cyclodextrin |
| US20050106192A1 (en) * | 2003-11-13 | 2005-05-19 | Parekh Prabodh P. | Synergistically-effective composition of zinc ricinoleate and one or more substituted monocyclic organic compounds and use thereof for preventing and/or suppressing malodors |
| ATE480592T1 (de) | 2004-05-24 | 2010-09-15 | Cellresin Tech Llc | Amphotere gepfropfte barrierematerialien |
| US20060093572A1 (en) * | 2004-11-03 | 2006-05-04 | Bordoloi Binoy K | Cyanoacrylate monomer formulation containing diiodomethyl-p-tolylsulfone and 2,4,4'-trichloro-2' -hydroxydiphenyl ether |
| CA2638768A1 (en) * | 2006-02-28 | 2007-09-07 | Tyco Healthcare Group Lp | Antimicrobial releasing polymers |
| US20070207189A1 (en) * | 2006-02-28 | 2007-09-06 | Nadya Belcheva | Antimicrobial medical devices |
| DE102006029829A1 (de) * | 2006-06-27 | 2008-01-03 | St. Antoniusheim Ggmbh | Konstruktionswerkstoff, insbesondere zur Herstellung von Bienenwabenrahmen, Bienenwabenmittelwände und/oder Zargen für Bienenbeuten |
| MX2009011902A (es) * | 2007-05-01 | 2010-04-30 | Oplon Bv | Empaquetamiento biocidico para cosmeticos y productos alimenticios. |
| CA2693944C (en) * | 2007-07-20 | 2015-11-17 | Ralf Dujardin | Polymer composite material with biocide functionality |
| US8012554B2 (en) * | 2007-09-12 | 2011-09-06 | Pactiv Corporation | Bags having odor management capabilities |
| US7901780B2 (en) * | 2008-06-25 | 2011-03-08 | Solutia Inc. | Polymer interlayers comprising blends of plasticized poly(vinyl butyral) and poly(cyclohexanedimethylene terephthalate-co-ethylene terephthalate) copolyester |
| US20120152149A1 (en) * | 2009-08-26 | 2012-06-21 | Basf Se | Use of 1,3-diols as biocides |
| AU2012374106B8 (en) * | 2012-03-22 | 2016-11-03 | Irpc Public Company Limited | Boring bivalve resistant polymer composition |
| WO2015044785A2 (en) | 2013-09-27 | 2015-04-02 | Basf Se | Polyolefin compositions for building materials |
| CN109052592A (zh) * | 2018-09-12 | 2018-12-21 | 武汉中新化工有限公司 | 一种聚酯切片生产过程中加药抑制微生物的方法 |
| CN112471145A (zh) * | 2020-12-04 | 2021-03-12 | 王立强 | 一种超高分子固体缓释消毒抑菌剂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567724A (en) * | 1968-10-31 | 1971-03-02 | Goodrich Co B F | Hexahydro-1,3,5-tris-(4-hydroxyaryl)-s-triazines |
| AR204937A1 (es) * | 1973-12-12 | 1976-03-19 | Ciba Geigy Ag | Procedimiento para aprestar y proveer cuero con un acabado antimicrobiano y preparaciones para ilevarlo a cabo |
| SU530047A1 (ru) * | 1974-07-05 | 1976-09-30 | Казанский Филиал Всесоюзного Ордена Трудового Красного Знамени Научно-Исследовательского Института Синтетического Каучука Им. Академика С.В.Лебедева | Полиэфирна композици |
| US4086297A (en) * | 1975-11-28 | 1978-04-25 | Ventron Corporation | Method of making polymeric compositions and compositions therefor |
| SU657041A1 (ru) * | 1976-09-14 | 1979-04-15 | Предприятие П/Я В-2913 | Способ стабилизации гомо-или сополимеров этилена |
| US4629621A (en) * | 1984-07-23 | 1986-12-16 | Zetachron, Inc. | Erodible matrix for sustained release bioactive composition |
| NZ215076A (en) | 1985-03-04 | 1988-09-29 | Thiokol Morton Inc | Non-foamed porous thermoplastic resin and microbiocide masterbatch and method of making same |
| JPS62544A (ja) * | 1985-06-26 | 1987-01-06 | Teisan Seiyaku Kk | ポリエステル系組成物の成型品及びその製造方法 |
| US4686239A (en) | 1986-04-17 | 1987-08-11 | Morton Thiokol, Inc. | Solid biocide dry blend |
| JPH0781233B2 (ja) * | 1988-08-10 | 1995-08-30 | 帝人株式会社 | 防ダニ性詰綿用繊維の製造方法 |
| US5229124A (en) * | 1990-04-02 | 1993-07-20 | Morton International, Inc. | Microbicides immobilized in water soluble thermoplastic resins and aqueous dispersions of microbicides prepared therefrom |
| US5639803A (en) | 1990-10-19 | 1997-06-17 | Olin Corporation | Process for incorporating biocides into a liquid dispersion |
| US5358979A (en) * | 1990-12-13 | 1994-10-25 | Akzo Nobel Nv | Primarily solid concentrate which contains a biocide |
| GB2262468A (en) | 1991-12-19 | 1993-06-23 | Yad Hygiene Products Limited | Moulding polymeric articles having a biocidally active surface |
| US5929132A (en) | 1992-11-19 | 1999-07-27 | Arch Chemicals, Inc. | Process for incorporating biocides into a liquid dispersion |
| US5702754A (en) * | 1995-02-22 | 1997-12-30 | Meadox Medicals, Inc. | Method of providing a substrate with a hydrophilic coating and substrates, particularly medical devices, provided with such coatings |
| JPH08239507A (ja) * | 1995-03-07 | 1996-09-17 | Toppan Printing Co Ltd | 抗菌性樹脂組成物 |
| JP3479150B2 (ja) * | 1995-03-14 | 2003-12-15 | アキレス株式会社 | 抗菌、防黴性インテグラルポリウレタンフォーム |
| JPH0977907A (ja) * | 1995-09-14 | 1997-03-25 | Wataboshi Sangyo Kk | 合成樹脂組成物 |
| GB9600661D0 (en) * | 1996-01-12 | 1996-03-13 | Woolard Trevor | Bactericidal compostions and articles containing them |
| EP0846418B1 (en) * | 1996-05-10 | 2006-08-16 | Toyo Boseki Kabushiki Kaisha | Antimicrobial composition and antimicrobial laminate |
| JPH1013929A (ja) * | 1996-06-20 | 1998-01-16 | Nippon Denki Ido Tsushin Kk | 自動車電話装置 |
| KR100279081B1 (ko) | 1996-11-26 | 2001-01-15 | 조민호 | 방출조절형농약제제 |
| JPH1112107A (ja) * | 1997-06-19 | 1999-01-19 | Suzuki Yushi Kogyo Kk | 水処理用除菌剤および除菌剤入り浴用剤 |
| AUPP060597A0 (en) * | 1997-11-27 | 1998-01-08 | Novapharm Research (Australia) Pty Ltd | Improved biocide and biocidal cloth |
| US5919554A (en) | 1998-01-30 | 1999-07-06 | Microban Products Company | Antimicrobial fiberglass reinforced plastic composite |
| JPH11263705A (ja) * | 1998-03-17 | 1999-09-28 | Nisshin Steel Co Ltd | 抗菌剤及び抗菌性樹脂組成物 |
| JPH11335206A (ja) * | 1998-05-22 | 1999-12-07 | Sanyo Chem Ind Ltd | 耐熱性に優れる樹脂用抗菌剤および抗菌性樹脂組成物 |
| WO2000053413A1 (en) | 1999-03-06 | 2000-09-14 | Icet, Inc. | Antimicrobial plastics |
-
1999
- 1999-12-20 US US09/467,809 patent/US6475505B1/en not_active Expired - Fee Related
-
2000
- 2000-12-12 DE DE60004004T patent/DE60004004T2/de not_active Expired - Lifetime
- 2000-12-12 ES ES00811173T patent/ES2202031T3/es not_active Expired - Lifetime
- 2000-12-12 EP EP00811173A patent/EP1114583B1/en not_active Expired - Lifetime
- 2000-12-12 PT PT00811173T patent/PT1114583E/pt unknown
- 2000-12-12 DK DK00811173T patent/DK1114583T3/da active
- 2000-12-12 AT AT00811173T patent/ATE245348T1/de active
- 2000-12-13 RU RU2000130944/04A patent/RU2258723C2/ru not_active IP Right Cessation
- 2000-12-16 KR KR1020000077395A patent/KR100691538B1/ko not_active Expired - Fee Related
- 2000-12-18 TW TW089127054A patent/TWI260969B/zh active
- 2000-12-18 CA CA002329023A patent/CA2329023C/en not_active Expired - Fee Related
- 2000-12-19 CN CNB001359592A patent/CN1190131C/zh not_active Expired - Fee Related
- 2000-12-19 JP JP2000385240A patent/JP2001172106A/ja active Pending
- 2000-12-20 BR BR0005939-0A patent/BR0005939A/pt not_active Application Discontinuation
-
2002
- 2002-07-22 US US10/199,268 patent/US7041307B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001172106A (ja) | 2001-06-26 |
| BR0005939A (pt) | 2001-11-27 |
| DE60004004T2 (de) | 2004-04-15 |
| KR100691538B1 (ko) | 2007-03-09 |
| ATE245348T1 (de) | 2003-08-15 |
| TWI260969B (en) | 2006-09-01 |
| ES2202031T3 (es) | 2004-04-01 |
| PT1114583E (pt) | 2003-12-31 |
| US20030027890A1 (en) | 2003-02-06 |
| US7041307B2 (en) | 2006-05-09 |
| CN1190131C (zh) | 2005-02-23 |
| DE60004004D1 (de) | 2003-08-28 |
| RU2258723C2 (ru) | 2005-08-20 |
| EP1114583A2 (en) | 2001-07-11 |
| EP1114583A3 (en) | 2001-09-19 |
| CN1300541A (zh) | 2001-06-27 |
| US6475505B1 (en) | 2002-11-05 |
| KR20010070305A (ko) | 2001-07-25 |
| DK1114583T3 (da) | 2003-11-17 |
| EP1114583B1 (en) | 2003-07-23 |
| CA2329023A1 (en) | 2001-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20121218 |