CA2211374C - Discoloration prevention in pyrithione-containing coating compositions - Google Patents
Discoloration prevention in pyrithione-containing coating compositions Download PDFInfo
- Publication number
- CA2211374C CA2211374C CA002211374A CA2211374A CA2211374C CA 2211374 C CA2211374 C CA 2211374C CA 002211374 A CA002211374 A CA 002211374A CA 2211374 A CA2211374 A CA 2211374A CA 2211374 C CA2211374 C CA 2211374C
- Authority
- CA
- Canada
- Prior art keywords
- zinc
- pyrithione
- ppm
- discoloration
- composition
- 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 - Lifetime
Links
- 229960002026 pyrithione Drugs 0.000 title claims abstract description 33
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 title claims abstract 4
- 239000008199 coating composition Substances 0.000 title description 3
- 238000004649 discoloration prevention Methods 0.000 title description 2
- 238000002845 discoloration Methods 0.000 claims abstract description 39
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical class [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000011787 zinc oxide Chemical class 0.000 claims abstract description 18
- 150000003751 zinc Chemical class 0.000 claims abstract description 17
- 150000003752 zinc compounds Chemical class 0.000 claims abstract description 10
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229940007718 zinc hydroxide Drugs 0.000 claims abstract description 10
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims abstract description 10
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 8
- 150000007524 organic acids Chemical class 0.000 claims abstract description 8
- 235000005985 organic acids Nutrition 0.000 claims abstract description 5
- 238000000576 coating method Methods 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- 229940000425 combination drug Drugs 0.000 claims 1
- 229920000136 polysorbate Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 69
- 239000003973 paint Substances 0.000 abstract description 64
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract description 26
- 229910001447 ferric ion Inorganic materials 0.000 abstract description 25
- 230000000845 anti-microbial effect Effects 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000853 adhesive Substances 0.000 abstract description 11
- 230000001070 adhesive effect Effects 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 10
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000565 sealant Substances 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 36
- 229940043810 zinc pyrithione Drugs 0.000 description 23
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 23
- -1 alkaline earth metal salt Chemical class 0.000 description 20
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000004816 latex Substances 0.000 description 9
- 229920000126 latex Polymers 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
- 229910000368 zinc sulfate Inorganic materials 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 4
- 229960001763 zinc sulfate Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000001840 Dandruff Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000005555 metalworking Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- WYSRTEVFLQJJDN-UHFFFAOYSA-N 2-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1Cl WYSRTEVFLQJJDN-UHFFFAOYSA-N 0.000 description 2
- 241000450419 Bouchetia erecta Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 230000003467 diminishing effect Effects 0.000 description 2
- ZHDBTKPXEJDTTQ-UHFFFAOYSA-N dipyrithione Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-] ZHDBTKPXEJDTTQ-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
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- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960003811 pyrithione disulfide Drugs 0.000 description 2
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- 239000002562 thickening agent Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
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- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- DLNPJWYSCKUGHI-UHFFFAOYSA-N 1-hydroxypyridine-2-thione;sodium Chemical compound [Na].ON1C=CC=CC1=S DLNPJWYSCKUGHI-UHFFFAOYSA-N 0.000 description 1
- VOHCMATXIKWIKC-UHFFFAOYSA-N 1-hydroxypyridine-2-thione;zinc Chemical compound [Zn].ON1C=CC=CC1=S VOHCMATXIKWIKC-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
-
- 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
- C09D5/1687—Use of special additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/02—Anti-oxidant compositions; Compositions inhibiting chemical change containing inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Inorganic Chemistry (AREA)
- Paints Or Removers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/383,122 US5562995A (en) | 1995-02-03 | 1995-02-03 | Discoloration prevention in pyrithione-containing coating compositions |
| US08/383,122 | 1995-02-03 | ||
| PCT/US1995/009722 WO1996023850A1 (en) | 1995-02-03 | 1995-08-03 | Discoloration prevention in pyrithione-containing coating compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2211374A1 CA2211374A1 (en) | 1996-08-08 |
| CA2211374C true CA2211374C (en) | 2003-12-30 |
Family
ID=23511816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002211374A Expired - Lifetime CA2211374C (en) | 1995-02-03 | 1995-08-03 | Discoloration prevention in pyrithione-containing coating compositions |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US5562995A (enExample) |
| EP (1) | EP0807152B1 (enExample) |
| JP (1) | JP3839847B2 (enExample) |
| KR (2) | KR100351016B1 (enExample) |
| CN (1) | CN1100108C (enExample) |
| AU (1) | AU3208195A (enExample) |
| CA (1) | CA2211374C (enExample) |
| DE (1) | DE69523948T2 (enExample) |
| DK (1) | DK0807152T3 (enExample) |
| TW (1) | TW321669B (enExample) |
| WO (1) | WO1996023850A1 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5916947A (en) * | 1994-12-02 | 1999-06-29 | Cape Cod Research, Inc. | Zinc oxide photoactive antifoulant material |
| US5939203A (en) * | 1995-02-03 | 1999-08-17 | Arch Chemicals, Inc. | Discoloration prevention in pyrithione-containing coating compositions |
| US6017562A (en) * | 1997-04-28 | 2000-01-25 | Arch Chemicals, Inc. | Non-spherical and non-platelet crystalline forms of pyrithione salts |
| US6242007B1 (en) | 1997-04-28 | 2001-06-05 | Arch Chemicals, Inc. | Non-spherical and non-platelet forms of pyrithione salts and methods of making same |
| US6032891A (en) * | 1998-05-29 | 2000-03-07 | Chang; Liang-Jen | Length counting device for a fishing reel |
| JP2000119111A (ja) * | 1998-10-16 | 2000-04-25 | Somar Corp | 増粘多糖類含有スラリー用防腐剤 |
| AU2008202828B8 (en) * | 1999-06-25 | 2011-08-11 | Arch Chemicals, Inc. | Pyrithione biocides enhanced by silver, copper, or zinc ions |
| US7455851B1 (en) | 1999-06-25 | 2008-11-25 | Arch Chemicals, Inc. | Pyrithione biocides enhanced by silver, copper, or zinc ions |
| US7026308B1 (en) | 1999-06-25 | 2006-04-11 | The Procter & Gamble Company | Topical anti-microbial compositions |
| BR0011858A (pt) * | 1999-06-25 | 2002-07-02 | Arch Chem Inc | Composição antimicrobiana |
| US7674785B2 (en) | 2000-06-22 | 2010-03-09 | The Procter & Gamble Company | Topical anti-microbial compositions |
| DE10040814A1 (de) | 2000-08-21 | 2002-03-07 | Thor Gmbh | Synergistische Biozidzusammensetzung |
| US7767010B2 (en) * | 2002-01-16 | 2010-08-03 | Smt, Inc. | Flame retardant and microbe inhibiting methods and compositions |
| US8715540B2 (en) * | 2002-01-16 | 2014-05-06 | MG3 Technologies Inc. | Aqueous and dry duel-action flame and smoke retardant and microbe inhibiting compositions, and related methods |
| CA2481994C (en) * | 2002-04-22 | 2009-12-08 | The Procter & Gamble Company | Personal care compositions comprising a zinc containing material in an aqueous surfactant composition |
| CN1646124B (zh) * | 2002-04-22 | 2010-05-26 | 宝洁公司 | 具有锌离子载体性能的物质的使用 |
| US8361450B2 (en) | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
| US8361448B2 (en) | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network |
| US9381148B2 (en) | 2003-03-18 | 2016-07-05 | The Procter & Gamble Company | Composition comprising particulate zinc material with a high relative zinc lability |
| US8470305B2 (en) | 2002-06-04 | 2013-06-25 | The Procter & Gamble Company | Shampoo containing a gel network |
| US8349301B2 (en) | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network |
| US9381382B2 (en) | 2002-06-04 | 2016-07-05 | The Procter & Gamble Company | Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network |
| US20050202984A1 (en) * | 2003-03-18 | 2005-09-15 | Schwartz James R. | Composition comprising zinc-containing layered material with a high relative zinc lability |
| US8491877B2 (en) * | 2003-03-18 | 2013-07-23 | The Procter & Gamble Company | Composition comprising zinc-containing layered material with a high relative zinc lability |
| US8367048B2 (en) | 2002-06-04 | 2013-02-05 | The Procter & Gamble Company | Shampoo containing a gel network |
| US8349302B2 (en) | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
| US6893752B2 (en) | 2002-06-28 | 2005-05-17 | United States Gypsum Company | Mold-resistant gypsum panel and method of making same |
| TWI289431B (en) * | 2002-09-30 | 2007-11-11 | Shimano Kk | Fishing reel, fishing information display device, and fishing information display system |
| US20040191331A1 (en) * | 2003-03-18 | 2004-09-30 | The Procter & Gamble Company | Composition comprising particulate zinc materials having a defined crystallite size |
| US20040213751A1 (en) * | 2003-03-18 | 2004-10-28 | Schwartz James Robert | Augmentation of pyrithione activity or a polyvalent metal salt of pyrithione activity by zinc-containing layered material |
| JP2004307483A (ja) * | 2003-04-07 | 2004-11-04 | Rohm & Haas Co | 殺微生物組成物 |
| US7056582B2 (en) * | 2003-04-17 | 2006-06-06 | Usg Interiors, Inc. | Mold resistant acoustical panel |
| JP4684551B2 (ja) | 2003-12-25 | 2011-05-18 | 東レ・ダウコーニング株式会社 | 変色防止又は変色低減方法及び変色防止又は変色低減剤並びに当該変色防止又は変色低減剤を含むジオルガノポリシロキサン組成物 |
| US9723842B2 (en) | 2006-05-26 | 2017-08-08 | Arch Chemicals, Inc. | Isothiazolinone biocides enhanced by zinc ions |
| EP2042489A1 (de) * | 2007-09-26 | 2009-04-01 | Straetmans high TAC GmbH | Beseitigen und Verhindern von Verfärbungen Pyrithion enthaltender Stoffe |
| EP2670239B1 (de) | 2011-02-03 | 2015-08-12 | Sanitized AG | Formulierung zur antimikrobiellen und fungiziden ausrüstung von polymermaterialien, insbesondere von lacken und beschichtungen |
| BR112014007727B1 (pt) | 2011-10-07 | 2019-04-30 | The Procter & Gamble Company | Composição de xampu e seu processo para preparação |
| BR112014019697B1 (pt) * | 2012-02-08 | 2020-12-15 | Janssen Pharmaceutica Nv | Método para prevenir a desativação de catalisadores metálicos em processos de polimerização catalítica |
| WO2013166718A1 (en) * | 2012-05-11 | 2013-11-14 | The Procter & Gamble Company | Personal cleansing compositions comprising zinc pyrithione |
| EP2879496B1 (en) | 2012-07-31 | 2018-08-22 | Arch Chemicals, Inc. | Composition and method for preventing discoloration of pyrithione containing compositions |
| MX2015004435A (es) | 2012-10-12 | 2015-06-24 | Arch Chem Inc | Composiciones biocidas que comprenden quelantes de hierro. |
| WO2014169464A1 (en) | 2013-04-18 | 2014-10-23 | The Procter & Gamble Company | Personal care compositions containing zinc pyrithione and zinc-phosphonate complex |
| WO2014139449A1 (en) | 2013-03-14 | 2014-09-18 | The Procter & Gamble Company | Solid concentrate compositions containing zinc pyrithione |
| CA2901658A1 (en) | 2013-03-14 | 2014-09-18 | The Procter & Gamble Company | Bar soap compositions containing zinc pyrithione and a zinc-pyridine oxide complex |
| EP3071038B1 (en) | 2013-11-19 | 2021-12-15 | Arch Chemicals, Inc. | Enhanced preservative |
| EP2944199B1 (en) | 2014-05-13 | 2016-08-31 | ViskoTeepak Belgium NV | Food casing with fungicidal characteristics |
| CN107613954B (zh) | 2015-03-26 | 2021-10-19 | Isp投资有限公司 | 脱氢乙酸的协同组合物以及减少各种终端组合物中的黄变的方法 |
| CN107846902B (zh) * | 2015-05-05 | 2021-06-01 | 康宁股份有限公司 | 展现协同功效的抗微生物材料 |
| US10945935B2 (en) | 2016-06-27 | 2021-03-16 | The Procter And Gamble Company | Shampoo composition containing a gel network |
| CN109476932B (zh) | 2016-07-19 | 2022-12-02 | 贝洱工艺公司 | 抗微生物涂料组合物及相关方法 |
| US20180098923A1 (en) | 2016-10-10 | 2018-04-12 | The Procter & Gamble Company | Personal care compositions substantially free of sulfated surfactants and containing a gel network |
| EP3801443A1 (en) | 2018-06-05 | 2021-04-14 | The Procter & Gamble Company | Clear cleansing composition |
| MX2021005464A (es) | 2018-12-14 | 2021-06-18 | Procter & Gamble | Composicion de champu que comprende microcapsulas de tipo lamina. |
| US11896689B2 (en) | 2019-06-28 | 2024-02-13 | The Procter & Gamble Company | Method of making a clear personal care comprising microcapsules |
| JP7453395B2 (ja) | 2020-02-14 | 2024-03-19 | ザ プロクター アンド ギャンブル カンパニー | 中に懸濁された審美的設計を有する液体組成物の保管に適合されたボトル |
| CN111748151A (zh) * | 2020-07-16 | 2020-10-09 | 上海威露美生物科技有限公司 | 抗菌防霉抗藻高分子聚合物及其制备方法 |
| US12053130B2 (en) | 2021-02-12 | 2024-08-06 | The Procter & Gamble Company | Container containing a shampoo composition with an aesthetic design formed by bubbles |
| US11633072B2 (en) | 2021-02-12 | 2023-04-25 | The Procter & Gamble Company | Multi-phase shampoo composition with an aesthetic design |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809971A (en) * | 1955-11-22 | 1957-10-15 | Olin Mathieson | Heavy-metal derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same |
| US3159640A (en) * | 1963-04-23 | 1964-12-01 | Olin Mathieson | Process for preparing 2-mercaptopyridine-nu oxide |
| US4161526A (en) * | 1978-07-20 | 1979-07-17 | Sterling Drug Inc. | Zinc salt prevention or removal of discoloration in pyrithione, pyrithione salt and dipyrithione compositions |
| US4482715A (en) * | 1982-02-26 | 1984-11-13 | Olin Corporation | Process for the prevention or reduction of discoloration of sodium or zinc pyrithione |
| US4396766A (en) * | 1982-04-28 | 1983-08-02 | Olin Corporation | Process for producing sodium and zinc pyrithione |
| DE3422510A1 (de) * | 1984-06-16 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ueber o,o'-methylenethergruppen verknuepften phenolresolethern und deren verwendung |
| US4957658A (en) * | 1987-08-31 | 1990-09-18 | Olin Corporation | Process and composition for providing reduced discoloration caused by the presence of pyrithione and ferric ion in water-based paints and paint bases |
| US4818436A (en) * | 1987-08-31 | 1989-04-04 | Olin Corporation | Process and composition for providing reduced discoloration of pyrithiones |
| US4888368A (en) * | 1988-05-12 | 1989-12-19 | Dow Corning Corporation | Method of inhibiting the discoloration of emulsions and discoloration resistant emulsion compositions |
| US4935061A (en) * | 1989-01-17 | 1990-06-19 | Olin Corporation | Process and composition for providing reduced discoloration caused by the presence of pyrithione and ferric ion in water-based paints and paint bases |
| EP0499817B1 (en) * | 1991-01-30 | 1995-05-17 | Dai Nippon Toryo Co., Ltd. | Antifouling coating composition |
| US5137569A (en) * | 1991-10-10 | 1992-08-11 | Olin Corporation | Process for stabilizing zinc pyrithione plus cuprous oxide in paint |
| US5227156A (en) * | 1992-04-14 | 1993-07-13 | Amway Corporation | Use of zinc compounds to stabilize a thiazolinone preservative in an anti-dandruff shampoo |
| US5232493A (en) * | 1992-09-01 | 1993-08-03 | Olin Corporation | Process for stabilizing zinc pyrithione plus cuprous oxide in paint |
| US5246489A (en) * | 1992-09-04 | 1993-09-21 | Olin Corporation | Process for generating copper pyrithione in-situ in a paint formulation |
| KR100317145B1 (ko) * | 1992-12-01 | 2002-12-06 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | 지속성을 갖는 항균제제 |
| US5314719A (en) * | 1993-03-18 | 1994-05-24 | Foster Products Corporation | Fungicidal protective coating for air handling equipment |
| US5298061A (en) * | 1993-05-14 | 1994-03-29 | Olin Corporation | Gel-free paint containing zinc pyrithione, cuprous oxide, and amine treated rosin |
| US5342437A (en) * | 1993-10-15 | 1994-08-30 | Olin Corporation | Gel-free paint containing zinc pyrithione cuprous oxide and carboxylic acid |
| US5518774A (en) * | 1995-06-26 | 1996-05-21 | Olin Corporation | In-can and dry coating antimicrobial |
-
1995
- 1995-02-03 US US08/383,122 patent/US5562995A/en not_active Expired - Lifetime
- 1995-08-03 KR KR1019970705296A patent/KR100351016B1/ko not_active Expired - Lifetime
- 1995-08-03 EP EP95928242A patent/EP0807152B1/en not_active Expired - Lifetime
- 1995-08-03 JP JP52349096A patent/JP3839847B2/ja not_active Expired - Lifetime
- 1995-08-03 WO PCT/US1995/009722 patent/WO1996023850A1/en not_active Ceased
- 1995-08-03 CA CA002211374A patent/CA2211374C/en not_active Expired - Lifetime
- 1995-08-03 KR KR1019970705296A patent/KR19980701899A/ko active Granted
- 1995-08-03 CN CN95197540A patent/CN1100108C/zh not_active Expired - Lifetime
- 1995-08-03 DK DK95928242T patent/DK0807152T3/da active
- 1995-08-03 AU AU32081/95A patent/AU3208195A/en not_active Abandoned
- 1995-08-03 DE DE69523948T patent/DE69523948T2/de not_active Expired - Lifetime
- 1995-08-17 TW TW084108605A patent/TW321669B/zh not_active IP Right Cessation
-
1996
- 1996-06-25 US US08/670,051 patent/US5883154A/en not_active Expired - Lifetime
-
1998
- 1998-12-16 US US09/212,877 patent/US6096122A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5562995A (en) | 1996-10-08 |
| CA2211374A1 (en) | 1996-08-08 |
| CN1100108C (zh) | 2003-01-29 |
| DE69523948T2 (de) | 2002-06-20 |
| TW321669B (enExample) | 1997-12-01 |
| US5883154A (en) | 1999-03-16 |
| KR100351016B1 (ko) | 2003-01-24 |
| EP0807152B1 (en) | 2001-11-14 |
| US6096122A (en) | 2000-08-01 |
| WO1996023850A1 (en) | 1996-08-08 |
| AU3208195A (en) | 1996-08-21 |
| JP3839847B2 (ja) | 2006-11-01 |
| DE69523948D1 (de) | 2001-12-20 |
| KR19987001899A (en) | 1998-06-25 |
| JPH10513211A (ja) | 1998-12-15 |
| KR19980701899A (ko) | 1998-06-25 |
| CN1175274A (zh) | 1998-03-04 |
| EP0807152A1 (en) | 1997-11-19 |
| EP0807152A4 (en) | 1998-11-25 |
| DK0807152T3 (da) | 2002-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20150803 |