Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

A composition, comprising:

• (a) 1 to 20 wt. %, based on the total weight of (a) and (b), of a transfer agent;
• and
• (b) 80 to 99 wt. %, based on the total weight of (a) and (b), of a barrier material;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• and
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride.

A composition, comprising:

• (a') 1 to 10 wt. %, based on the total weight of (a'), (b'), and (c') of a transfer agent;
• (b') 70 to 98 wt. %, based on the total weight of (a'), (b'), and (c') of a barrier material;
• and
• (c') 1 to 20 wt. %, based on the total weight of (a'), (b'), and (c'), of an active agent;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride;
• and
• wherein said active agent is selected from the group consisting of
• ' . 5-dibromosalicylanilide,
• 3,4',5-trichlorosalicylanilide,
• 3,4',5-tribromosalicylanilide,
• 2,3,3',5-tetrachlorosalicylanilide,
• 3,3,3',5-tetrachlorosalicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide,
• 5-n-octanoyl-3'-trifluoromethyl salicylanilide,
• 3,5-dibromo-4'-trifluoromethyl salicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide
• methyl p-hydroxybenzoic ester,
• ethyl p-hydroxybenzoic ester,
• propyl p-hydroxybenzoic ester,
• butyl p-hydroxybenzoic ester,
• 2',4,4'-trichloro-2-hydroxy-diphenyl ether,
• 2,2'-dihydroxy-5,5'-dibromo-diphenyl ether,
• 3,4,4'-trichlorocarbanilide,
• 3-trifluoromethyl-4,4'-dichlorocarbanilide,
• 3,3,4'-trichlorocarbanilide,
• Phenol
• 2-methyl-phenol,
• 3-methyl-phenol,
• 4-methyl-phenol,
• 4-ethyl-phenol,
• 2,4-dimethyl-phenol,
• 2,5-dimethyl-phenol,
• 3,4-dimethyl-phenol,
• 2,6-dimethyl-phenol,
• 4-n-propyl-phenol,
• 4-n-butyl-phenol,
• 4-n-amyl-phenol,
• 4-tert-amyl-phenol,
• 4-n-hexyl-phenol,
• 4-n-heptyl-phenol,
• 2-methoxy-4-(2-propenyl)-phenol,
• 2-isopropyl-5-methyl-phenol,
• methyl-p-chlorophenol,
• ethyl-p-chlorophenol,
• n-propyl-p-chlorophenol,
• n-butyl-p-chlorophenol,
• n-amyl-p-chlorophenol,
• sec-amyl-p-chlorophenol,
• n-hexyl-p-chlorophenol,
• cyclohexyl-p-chlorophenol,
• n-heptyl-p-chlorophenol,
• n-octyl-p-chlorophenol,
• methyl-o-chlorophenol,
• ethyl-o-chlorophenol,
• n-propyl-o-chlorophenol,
• n-butyl-o-chlorophenol,
• n-amyl-o-chlorophenol,
• tert-amyl-o-chlorophenol,
• n-hexyl-o-chlorophenol,
• n-heptyl-o-chlorophenol,
• o-benzyl-p-chlorophenol,
• o-benzyl-m-methyl-p-chlorophenol,
• o-benzyl-m,m-dimethyl-p-chlorophenol,
• o-phenylethyl-p-chlorophenol,
• o-phenylethyl-m-methyl-p-chlorophenol,
• 3-methyl-p-chlorophenol,
• 3,5-dimethyl-p-chlorophenol,
• 6-ethyl-3-methyl-p-chlorophenol,
• 6-n-propyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-3-methyl-p-chlorophenol,
• 2-ethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-butyl-3-methyl-p-chlorophenol,
• 2-iso-propyl-3,5-dimethyl-p-chlorophenol,
• 6-diethylmethyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol,
• 2-sec-amyl-3,5-dimethyl-p-chlorophenol,
• 2-diethylmethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-octyl-3-methyl-p-chlorophenol,
• methyl-p-bromophenol,
• ethyl-p-bromophenol,
• n-propyl-p-bromophenol,
• n-butyl-p-bromophenol,
• n-amyl-p-bromophenol,
• sec-amyl-p-bromophenol,
• n-hexyl-p-bromophenol,
• cyclohexyl-p-bromophenol,
• tert-amyl-o-bromophenol,
• n-hexyl-o-bromophenol,
• n-propyl-m,m-dimethyl-o-bromophenol,
• 2-phenylphenol,
• 4-chloro-2-methylphenol,
• 4-chloro-3-methylphenol,
• 4-chloro-3,5-dimethylphenol,
• 2,4-dichloro-3,5-dimethylphenol,
• 3,4,5,6-tetrabromo-2-methylphenol,
• 5-methyl-2-pentylphenol,
• 4-isopropyl-3-methylphenol,
• 5-chloro-2-hydroxydiphenylmethane,
• resorcinol
• methyl-resorcinol,
• ethyl-resorcinol,
• n-propyl-resorcinol,
• n-butyl-resorcinol,
• n-amyl-resorcinol,
• n-hexyl-resorcinol,
• n-heptyl-resorcinol,
• n-octyl-resorcinol,
• n-nonyl-resorcinol,
• phenyl-resorcinol,
• benzyl-resorcinol,
• phenylethyl-resorcinol,
• phenylpropyl-resorcinol,
• p-chlorobenzyl-resorcinol,
• 5-chloro-2,4-dihydroxydiphenylmethane,
• 4'-chloro-2,4-dihydroxydiphenylmethane,
• 5-bromo-2,4-dihydroxydiphenylmethane,
• 4'-bromo-2,4-dihydroxydiphenylmethane,
• 2,2'-methylene bis(4-chlorophenol),
• 2,2'-methylene bis(3,4,6-trichlorophenol),
• 2,2'-methylene bis(4-chloro-6-bromophenol),
• bis(2-hydroxy-3,5-dichlorophenyl) sulfide,
• bis(2-hydroxy-5-chlorobenzyl) sulfide,
• benzethonium chloride,
• diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride,
• cetyl pyridinium chloride,
• cetyl pyridinium bromide,
• cetyl pyridinium iodide,
• cetyl pyridinium fluoride,
• dodecyl trimethyl ammonium bromide,
• benzyl dimethyl stearyl ammonium chloride,
• monocyclic oxazolidines,
• bicyclic oxalidines,
• polymeric bicyclic oxalidines,
• 1. 3-dioxanes, oxazolines,
• oxazolidinones,
• 5-amino-1,3-bis(2-ethylhexyl)-5-methyl hexahydropyrimidine,
• 1,6-bis-(p-chlorophenyldiguanidine)hexane,
• 1,6-di-(2-ethylhexyldiguanidine)hexane,
• 1,1'-hexamethylene-bis-{5-(4-fluorophenyl)-diguanidine},
• sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleylaminofluoride, cetyl aminofluoride, ethanolaminohydrofluoride, potassium hexafluorosilicate,
• sodium hexafluorosilicate,
• sodium fluorophosphate,
• ammonium fluorophosphate,
• potassium fluorophosphate,
• magnesium fluorphosphate,
• calcium fluorophosphate,
• sodium fluorozirconate,
• potassium fluorozirconate,
• tin fluorozirconate,
• penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, niddamycin, metronidazole, spiramycin, and tetracycline.

A method of protecting teeth, comprising treating teeth with a composition comprising:

• (a) 1 to 20 wt. %, based on the total weight of (a) and (b), of a transfer agent;
• and
• (b) 80 to 99 wt. %, based on the total weight of (a) and (b), of a barrier material;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• and
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride.

A method of protecting teeth, comprising treating teeth with a composition comprising:

• (a') 1 to 10 wt. %, based on the total weight of (a'), (b'), and (c') of a transfer agent;
• (b') 70 to 98 wt. %, based on the total weight of (a'), (b'), and (c'), of a barrier material;
• and
• (c') 1 to 20 wt. %, based on the total weight of (a'), (b'), and (c'), of an active agent;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride;
• and
• wherein said active agent is selected from the group consisting of
• ' . 5-dibromosalicylanilide,
• 3,4',5-trichlorosalicylanilide,
• 3,4',5-tribromosalicylanilide,
• 2,3,3',5-tetrachlorosalicylanilide,
• 3,3,3',5-tetrachlorosalicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide,
• 5-n-octanoyl-3'-trifluoromethyl salicylanilide,
• 3,5-dibromo-4'-trifluoromethyl salicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide,
• methyl p-hydroxybenzoic ester,
• ethyl p-hydroxybenzoic ester,
• propyl p-hydroxybenzoic ester,
• butyl p-hydroxybenzoic ester,
• ' . 4,4'-trichloro-2-hydroxy-diphenyl ether,
• 2,2'-dihydroxy-5,5'-dibromo-diphenyl ether,
• 3,4,4'-trichlorocarbanilide,
• 3-trifluoromethyl-4,4'-dichlorocarbanilide,
• 3,3,4'-trichlorocarbanilide,
• Phenol
• 2-methyl-phenol,
• 3-methyl-phenol,
• 4-methyl-phenol,
• 4-ethyl-phenol,
• 2,4-dimethyl-phenol,
• 2,5-dimethyl-phenol,
• 3,4-dimethyl-phenol,
• 2,6-dimethyl-phenol,
• 4-n-propyl-phenol,
• 4-n-butyl-phenol,
• 4-n-amyl-phenol,
• 4-tert-amyl-phenol,
• 4-n-hexyl-phenol,
• 4-n-heptyl-phenol,
• 2-methoxy-4-(2-propenyl)-phenol,
• 2-isopropyl-5-methyl-phenol,
• methyl-p-chlorophenol,
• ethyl-p-chlorophenol,
• n-propyl-p-chlorophenol,
• n-butyl-p-chlorophenol,
• n-amyl-p-chlorophenol,
• sec-amyl-p-chlorophenol,
• n-hexyl-p-chlorophenol,
• cyclohexyl-p-chlorophenol,
• n-heptyl-p-chlorophenol,
• n-octyl-p-chlorophenol,
• methyl-o-chlorophenol,
• ethyl-o-chlorophenol,
• n-propyl-o-chlorophenol,
• n-butyl-o-chlorophenol,
• n-amyl-o-chlorophenol,
• tert-amyl-o-chlorophenol,
• n-hexyl-o-chlorophenol,
• n-heptyl-o-chlorophenol,
• o-benzyl-p-chlorophenol,
• o-benzyl-m-methyl-p-chlorophenol,
• o-benzyl-m,m-dimethyl-p-chlorophenol,
• o-phenylethyl-p-chlorophenol,
• o-phenylethyl-m-methyl-p-chlorophenol,
• 3-methyl-p-chlorophenol,
• 3,5-dimethyl-p-chlorophenol,
• 6-ethyl-3-methyl-p-chlorophenol,
• 6-n-propyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-3-methyl-p-chlorophenol,
• 2-ethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-butyl-3-methyl-p-chlorophenol,
• 2-iso-propyl-3,5-dimethyl-p-chlorophenol,
• 6-diethylmethyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol,
• 2-sec-amyl-3,5-dimethyl-p-chlorophenol,
• 2-diethylmethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-octyl-3-methyl-p-chlorophenol,
• methyl-p-bromophenol,
• ethyl-p-bromophenol,
• n-propyl-p-bromophenol,
• n-butyl-p-bromophenol,
• n-amyl-p-bromophenol,
• sec-amyl-p-bromophenol,
• n-hexyl-p-bromophenol,
• cyclohexyl-p-bromophenol,
• tert-amyl-o-bromophenol,
• n-hexyl-o-bromophenol,
• n-propyl-m,m-dimethyl-o-bromophenol,
• 2-phenylphenol,
• 4-chloro-2-methylphenol,
• 4-chloro-3-methylphenol,
• 4-chloro-3,5-dimethylphenol,
• 2,4-dichloro-3,5-dimethylphenol,
• 3,4,5,6-tetrabromo-2-methylphenol,
• 5-methyl-2-pentylphenol,
• 4-isopropyl-3-methylphenol,
• 5-chloro-2-hydroxydiphenylmethane,
• resorcinol
• methyl-resorcinol,
• ethyl-resorcinol,
• n-propyl-resorcinol,
• n-butyl-resorcinol,
• n-amyl-resorcinol,
• n-hexyl-resorcinol,
• n-heptyl-resorcinol,
• n-octyl-resorcinol,
• n-nonyl-resorcinol,
• phenyl-resorcinol,
• benzyl-resorcinol,
• phenylethyl-resorcinol,
• phenylpropyl-resorcinol,
• p-chlorobenzyl-resorcinol,
• 5-chloro-2,4-dihydroxydiphenylmethane,
• 4'-chloro-2,4-dihydroxydiphenylmethane,
• 5-bromo-2,4-dihydroxydiphenylmethane,
• 4'-bromo-2,4-dihydroxydiphenylmethane,
• 2,2'-methylene bis(4-chlorophenol),
• 2,2'-methylene bis(3,4,6-trichlorophenol),
• 2,2'-methylene bis(4-chloro-6-bromophenol),
• bis(2-hydroxy-3,5-dichlorophenyl) sulfide,
• bis(2-hydroxy-5-chlorobenzyl) sulfide,
• benzethonium chloride,
• diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride,
• cetyl pyridinium chloride,
• cetyl pyridinium bromide,
• cetyl pyridinium iodide,
• cetyl pyridinium fluoride,
• dodecyl trimethyl ammonium bromide,
• benzyl dimethyl stearyl ammonium chloride,
• monocyclic oxazolidines,
• bicyclic oxalidines,
• polymeric bicyclic oxalidines,
• 1. 3-dioxanes, oxazolines,
• oxazolidinones,
• 5-amino-1,3-bis(2-ethylhexyl)-5-methyl hexahydropyrimidine,
• 1,6-bis-(p-chlorophenyldiguanidine)hexane,
• 1,6-di-(2-ethylhexyldiguanidine)hexane,
• 1,1'-hexamethylene-bis-{5-(4-fluorophenyl)-diguanidine},
• sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleylaminofluoride, cetyl aminofluoride, ethanolaminohydrofluoride, potassium hexafluorosilicate,
• sodium hexafluorosilicate,
• sodium fluorophosphate,
• ammonium fluorophosphate,
• potassium fluorophosphate,
• magnesium fluorphosphate,
• calcium fluorophosphate,
• sodium fluorozirconate,
• potassium fluorozirconate,
• tin fluorozirconate,
• penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, niddamycin, metronidazole, spiramycin, and tetracycline.

A dental delivery system, comprising a substrate coated with a composition comprising:

• (a) 1 to 20 wt. %, based on the total weight of (a) and (b), of a transfer agent;
• and
• (b) 80 to 99 wt. %, based on the total weight of (a) and (b), of a barrier material;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• and
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride.

A dental delivery system, comprising a substrate coated with a composition comprising:

• (a') 1 to 10 wt. %, based on the total weight of (a'), (b'), and (c') of a transfer agent;
• (b') 70 to 98 wt. %, based on the total weight of (a'), (b'), and (c') of a barrier material;
• and
• (c') 1 to 20 wt. %, based on the total weight of (a'), (b'), and (c'), of an active agent;
• wherein said transfer agent is poly(ethyleneimine) in which 5 to 95 mole % of the nitrogen atoms have been derivatized by reaction with a C.sub.8-20 fatty acid halide and 5 to 95 mole % of the nitrogen atoms have been quaternized with HF;
• wherein said barrier material is selected from the group consisting of beeswax, lanolin, spermaceti, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylenic polymer waxes, polymethylene waxes, polymethylalkylsiloxane, polydimethylsiloxane, poly(perfluoroalkylmethyl siloxane), poly(methyl-3,3,3-trifluoropropyl siloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinylfluoride;
• and
• wherein said active agent is selected from the group consisting of
• 4',5-dibromosalicylanilide,
• 3,4',5-trichlorosalicylanilide,
• 3,4',5-tribromosalicylanilide,
• 2,3,3',5-tetrachlorosalicylanilide,
• 3. 3,3',5-tetrachlorosalicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide,
• 5-n-octanoyl-3'-trifluoromethyl salicylanilide,
• 3,5-dibromo-4'-trifluoromethyl salicylanilide,
• 3,5-dibromo-3'-trifluoromethyl salicylanilide
• methyl p-hydroxybenzoic ester,
• ethyl p-hydroxybenzoic ester,
• propyl p-hydroxybenzoic ester,
• butyl p-hydroxybenzoic ester,
• 2'4,4'-trichloro-2-hydroxy-diphenyl ether,
• 2,2'-dihydroxy-5,5'-dibromo-diphenyl ether,
• 3,4,4'-trichlorocarbanilide,
• 3-trifluoromethyl-4,4'-dichlorocarbanilide,
• 3,3,4'-trichlorocarbanilide,
• Phenol
• 2-methyl-phenol,
• 3-methyl-phenol,
• 4-methyl-phenol,
• 4-ethyl-phenol,
• 2,4-dimethyl-phenol,
• 2,5-dimethyl-phenol,
• 3,4-dimethyl-phenol,
• 2,6-dimethyl-phenol,
• 4-n-propyl-phenol,
• 4-n-butyl-phenol,
• 4-n-amyl-phenol,
• 4-tert-amyl-phenol,
• 4-n-hexyl-phenol,
• 4-n-heptyl-phenol,
• 2-methoxy-4-(2-propenyl)-phenol,
• 2-isopropyl-5-methyl-phenol,
• methyl-p-chlorophenol,
• ethyl-p-chlorophenol,
• n-propyl-p-chlorophenol,
• n-butyl-p-chlorophenol,
• n-amyl-p-chlorophenol,
• sec-amyl-p-chlorophenol,
• n-hexyl-p-chlorophenol,
• cyclohexyl-p-chlorophenol,
• n-heptyl-p-chlorophenol,
• n-octyl-p-chlorophenol,
• methyl-o-chlorophenol,
• ethyl-o-chlorophenol,
• n-propyl-o-chlorophenol,
• n-butyl-o-chlorophenol,
• n-amyl-o-chlorophenol,
• tert-amyl-o-chlorophenol,
• n-hexyl-o-chlorophenol,
• n-heptyl-o-chlorophenol,
• o-benzyl-p-chlorophenol,
• o-benzyl-m-methyl-p-chlorophenol,
• o-benzyl-m,m-dimethyl-p-chlorophenol,
• o-phenylethyl-p-chlorophenol,
• o-phenylethyl-m-methyl-p-chlorophenol,
• 3-methyl-p-chlorophenol,
• 3,5-dimethyl-p-chlorophenol,
• 6-ethyl-3-methyl-p-chlorophenol,
• 6-n-propyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-3-methyl-p-chlorophenol,
• 2-ethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-butyl-3-methyl-p-chlorophenol,
• 2-iso-propyl-3,5-dimethyl-p-chlorophenol,
• 6-diethylmethyl-3-methyl-p-chlorophenol,
• 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol,
• 2-sec-amyl-3,5-dimethyl-p-chlorophenol,
• 2-diethylmethyl-3,5-dimethyl-p-chlorophenol,
• 6-sec-octyl-3-methyl-p-chlorophenol,
• methyl-p-bromophenol,
• ethyl-p-bromophenol,
• n-propyl-p-bromophenol,
• n-butyl-p-bromophenol,
• n-amyl-p-bromophenol,
• sec-amyl-p-bromophenol,
• n-hexyl-p-bromophenol,
• cyclohexyl-p-bromophenol,
• tert-amyl-o-bromophenol,
• n-hexyl-o-bromophenol,
• n-propyl-m,m-dimethyl-o-bromophenol,
• 2-phenylphenol,
• 4-chloro-2-methylphenol,
• 4-chloro-3-methylphenol,
• 4-chloro-3,5-dimethylphenol,
• 2,4-dichloro-3,5-dimethylphenol,
• 3,4,5,6-tetrabromo-2-methylphenol,
• 5-methyl-2-pentylphenol,
• 4-isopropyl-3-methylphenol,
• 5-chloro-2-hydroxydiphenylmethane,
• resorcinol
• methyl-resorcinol,
• ethyl-resorcinol,
• n-propyl-resorcinol,
• n-butyl-resorcinol,
• n-amyl-resorcinol,
• n-hexyl-resorcinol,
• n-heptyl-resorcinol,
• n-octyl-resorcinol,
• n-nonyl-resorcinol,
• phenyl-resorcinol,
• benzyl-resorcinol,
• phenylethyl-resorcinol,
• phenylpropyl-resorcinol,
• p-chlorobenzyl-resorcinol,
• 5-chloro-2,4-dihydroxydiphenylmethane,
• 4'-chloro-2,4-dihydroxydiphenylmethane,
• 5-bromo-2,4-dihydroxydiphenylmethane,
• 4'-bromo-2,4-dihydroxydiphenylmethane,
• 2,2'-methylene bis(4-chlorophenol),
• 2,2'-methylene bis(3,4,6-trichlorophenol),
• 2. 2'-methylene bis(4-chloro-6-bromophenol),
• bis(2-hydroxy-3,5-dichlorophenyl) sulfide,
• bis(2-hydroxy-5-chlorobenzyl) sulfide,
• benzethonium chloride,
• diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride,
• cetyl pyridinium chloride,
• cetyl pyridinium bromide,
• cetyl pyridinium iodide,
• cetyl pyridinium fluoride,
• dodecyl trimethyl ammonium bromide,
• benzyl dimethyl stearyl ammonium chloride,
• monocyclic oxazolidines,
• bicyclic oxalidines,
• polymeric bicyclic oxalidines,
• 1,3-dioxanes, oxazolines,
• oxazolidinones,
• 5-amino-1,3-bis(2-ethylhexyl)-5-methyl hexahydropyrimidine,
• 1,6-bis-(p-chlorophenyldiguanidine)hexane,
• 1,6-di-(2-ethylhexyldiguanidine)hexane,
• 1,1'-hexamethylene-bis-{5-(4-fluorophenyl)-diguanidine},
• sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleylaminofluoride, cetyl aminofluoride, ethanolaminohydrofluoride, potassium hexafluorosilicate,
• sodium hexafluorosilicate,
• sodium fluorophosphate,
• ammonium fluorophosphate,
• potassium fluorophosphate,
• magnesium fluorphosphate,
• calcium fluorophosphate,
• sodium fluorozirconate,
• potassium fluorozirconate,
• tin fluorozirconate,
• penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, niddamycin, metronidazole, spiramycin, and tetracycline.