JP3839847B2 - ピリチオン含有コーティング組成物の変色防止 - Google Patents
ピリチオン含有コーティング組成物の変色防止 Download PDFInfo
- Publication number
- JP3839847B2 JP3839847B2 JP52349096A JP52349096A JP3839847B2 JP 3839847 B2 JP3839847 B2 JP 3839847B2 JP 52349096 A JP52349096 A JP 52349096A JP 52349096 A JP52349096 A JP 52349096A JP 3839847 B2 JP3839847 B2 JP 3839847B2
- Authority
- JP
- Japan
- 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
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 title claims description 37
- 238000002845 discoloration Methods 0.000 title claims description 36
- 229960002026 pyrithione Drugs 0.000 title claims description 34
- 239000008199 coating composition Substances 0.000 title claims description 15
- 230000002265 prevention Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 54
- 239000003973 paint Substances 0.000 claims description 53
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical class [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 23
- 239000011787 zinc oxide Chemical class 0.000 claims description 15
- -1 organic acid zinc salts Chemical class 0.000 claims description 13
- 150000003751 zinc Chemical class 0.000 claims description 9
- 150000003752 zinc compounds Chemical class 0.000 claims description 9
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 9
- 229940007718 zinc hydroxide Drugs 0.000 claims description 9
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 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 description 2
- 239000011247 coating layer Substances 0.000 claims 6
- 239000010410 layer Substances 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 1
- 229940043810 zinc pyrithione Drugs 0.000 description 21
- 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 21
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 20
- 229910001447 ferric ion Inorganic materials 0.000 description 20
- 230000000845 anti-microbial effect Effects 0.000 description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 239000000565 sealant Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 229920000126 latex Polymers 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
- 239000003755 preservative agent Substances 0.000 description 5
- 230000002335 preservative effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 238000005555 metalworking Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 3
- 229960001763 zinc sulfate Drugs 0.000 description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WYSRTEVFLQJJDN-UHFFFAOYSA-N 2-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1Cl WYSRTEVFLQJJDN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000004599 antimicrobial Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 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
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- FPZVGADNYUTBRL-UHFFFAOYSA-N [S-][S-].[Mg+2] Chemical compound [S-][S-].[Mg+2] FPZVGADNYUTBRL-UHFFFAOYSA-N 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940045110 chitosan Drugs 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- ZHDBTKPXEJDTTQ-UHFFFAOYSA-N dipyrithione Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-] ZHDBTKPXEJDTTQ-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
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- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000314 lubricant 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
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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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 |
|---|---|---|---|
| US383,122 | 1995-02-03 | ||
| US08/383,122 US5562995A (en) | 1995-02-03 | 1995-02-03 | Discoloration prevention in pyrithione-containing coating compositions |
| PCT/US1995/009722 WO1996023850A1 (en) | 1995-02-03 | 1995-08-03 | Discoloration prevention in pyrithione-containing coating compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10513211A JPH10513211A (ja) | 1998-12-15 |
| JP3839847B2 true JP3839847B2 (ja) | 2006-11-01 |
Family
ID=23511816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52349096A Expired - Lifetime JP3839847B2 (ja) | 1995-02-03 | 1995-08-03 | ピリチオン含有コーティング組成物の変色防止 |
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)
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|---|---|---|---|---|
| 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 |
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| 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 |
| CA2211374C (en) | 2003-12-30 |
| 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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