EP0724622A1 - Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaire - Google Patents
Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaireInfo
- Publication number
- EP0724622A1 EP0724622A1 EP94923277A EP94923277A EP0724622A1 EP 0724622 A1 EP0724622 A1 EP 0724622A1 EP 94923277 A EP94923277 A EP 94923277A EP 94923277 A EP94923277 A EP 94923277A EP 0724622 A1 EP0724622 A1 EP 0724622A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- solution
- present
- polyoxypropylene
- polyoxyethylene
- block copolymer
- 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.)
- Withdrawn
Links
- -1 quaternary ammonium phosphate esters Chemical class 0.000 title claims abstract description 74
- 238000004140 cleaning Methods 0.000 title claims abstract description 41
- 239000004254 Ammonium phosphate Substances 0.000 title 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 title 1
- 235000019289 ammonium phosphates Nutrition 0.000 title 1
- 239000000243 solution Substances 0.000 claims abstract description 81
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 31
- 230000000249 desinfective effect Effects 0.000 claims abstract description 25
- 239000004599 antimicrobial Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 18
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 18
- 239000010452 phosphate Substances 0.000 claims abstract description 18
- 229920001400 block copolymer Polymers 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000012487 rinsing solution Substances 0.000 claims abstract description 11
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 241000289690 Xenarthra Species 0.000 claims abstract description 4
- 239000004094 surface-active agent Substances 0.000 claims description 30
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 24
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 14
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 14
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 14
- 239000004327 boric acid Substances 0.000 claims description 14
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 14
- 229910021538 borax Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 12
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000002738 chelating agent Substances 0.000 claims description 5
- BYMMIQCVDHHYGG-UHFFFAOYSA-N Cl.OP(O)(O)=O Chemical compound Cl.OP(O)(O)=O BYMMIQCVDHHYGG-UHFFFAOYSA-N 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 13
- 241000607715 Serratia marcescens Species 0.000 abstract description 11
- 230000003013 cytotoxicity Effects 0.000 abstract description 3
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 229920001983 poloxamer Polymers 0.000 description 21
- 150000003904 phospholipids Chemical class 0.000 description 14
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 10
- 230000003641 microbiacidal effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
- 241001225321 Aspergillus fumigatus Species 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 4
- 239000006172 buffering agent Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920006317 cationic polymer Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FPWSFGKGWVUHTF-UHFFFAOYSA-N 2-hydroxyethyl 2-methylbut-2-enoate Chemical compound CC=C(C)C(=O)OCCO FPWSFGKGWVUHTF-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical class C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 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
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920002021 Pluronic® F 77 Polymers 0.000 description 1
- 229920002023 Pluronic® F 87 Polymers 0.000 description 1
- 229920002046 Pluronic® L 62 LF Polymers 0.000 description 1
- 229920002048 Pluronic® L 92 Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 1
- 229920002359 Tetronic® Polymers 0.000 description 1
- 239000007997 Tricine buffer Substances 0.000 description 1
- ISRLGZXSKRDKID-JXBDSQKUSA-N [3-bis[3-[dimethyl-[3-[[(9z,12z)-octadeca-9,12-dienoyl]amino]propyl]azaniumyl]-2-hydroxypropoxy]phosphoryloxy-2-hydroxypropyl]-dimethyl-[3-[[(9z,12z)-octadeca-9,12-dienoyl]amino]propyl]azanium;trichloride Chemical compound [Cl-].[Cl-].[Cl-].CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCC[N+](C)(C)CC(O)COP(=O)(OCC(O)C[N+](C)(C)CCCNC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OCC(O)C[N+](C)(C)CCCNC(=O)CCCCCCC\C=C/C\C=C/CCCCC ISRLGZXSKRDKID-JXBDSQKUSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000882 contact lens solution Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- VMDFZGPHEWEXQX-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.C=C.CC=C VMDFZGPHEWEXQX-UHFFFAOYSA-N 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
- A61L12/143—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0078—Compositions for cleaning contact lenses, spectacles or lenses
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/008—Polymeric surface-active agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- the present invention generally relates to a composition for and a method of cleaning and disinfecting contact lenses and more particularly relates to an improved composition for a contact lens cleaning and disinfecting solution containing a non-ionic surfactant and a triquatemary phosphate ester and a method of using the solution.
- It contains a polyoxyethylene/polyoxypropylene block copolymer having a molecular weight between 1900 and 15,500, a microbial growth inhibitor of benzalkonium chloride, purified water and a sufficient amount of at least one essentially neutral, water-soluble compatible salt to provide a solution salt content equivalent to about 0.5% to 1 .8% (w/v) sodium chloride.
- the solution may optionally contain bisodium or trisodium ethylenediamine tetraacetate and a polymeric viscosity-building agent.
- Krezanoski, et al. employed benzalkonium chloride as the anti-microbial agent which when combined with the surfactant of polyoxyethylene/polyoxypropylene block copolymer has been found to be not completely effective in its anti-microbial activities.
- U.S. Patent No. 4,504,405 to Howes discloses a substantially isotonic aqueous solution suitable for the cleaning of soft and gas permeable contact lenses comprising a sterile aqueous solution of 0.01 % to 2.00% of an ophthalmically acceptable non-ionic surface active agent, 0.0012% to 0.003% of a chlorohexidine salt and sufficient amount of non-ionic tonicity adjusting agent.
- the solution taught by Howes may preferably include a non-ionic surface active agent of polyoxyethylene/polyoxypropylene block copolymer.
- Howes does not teach the use of the desirable triquatemary phosphate ester anti-microbial agent.
- U.S. Patent No. 4,908,147 to Tsao, et al. discloses an aqueous self- preserving soft contact lens solution containing between 0.005% to 2.0% by weight of a water-soluble amphoteric surfactant; between 0% to 5% by weight of a substantially non-ionic surfactant which may suitably be a polyoxyethylene/polyoxypropylene block copolymer; between 0% to 5% by weight of a thickener; between 0% to 1 % by weight of a chelating agent; between 0% to 2% by weight of a buffer; between 0% to 2% by weight of a water-soluble salt compatible with ocular tissue, and the remainder water.
- the purpose of Tsao, et al.'s composition is to preserve and clean soft contact lenses by using an effective surfactant and a preservative of the amphoteric compound. It does not provide a single step from storage - to the eye solution.
- a commercial lens care solution is supplied by I.C.N. Corporation under the trade name of Unicare Green ® .
- This commercially available lens care solution contains a polyoxyethylene/polyoxypropylenecopolymer non-ionic surfactant
- F127 having a molecular weight of 12,600 and containing 70% polyoxyethylene and 30% polyoxypropylene and a triquatemary phosphate ester anti-microbial agent.
- the solution has poor cleaning properties.
- the solution also has a poor anti-microbial activity in a six hour log reduction test against 5. marcescens.
- Detailed information about the polyoxyethylene/polyoxypropylene copolymer non-ionic surfactant may be found in a technical pamphlet published by BASF Corporation (Parsippany, N.J.) "Pluronic ® & Tetronic ® Surfactants” (1989).
- a cleaning, disinfecting, and rinsing solution for contact lenses having superior cleaning and anti-microbial properties can be formulated.
- This solution preferably comprises between about 0.1 % to about 1.0% (w/v) of a non-ionic surfactant of polyoxyethylene/polyoxypropylene block copolymer having a molecular weight less than 13,000 daltons, a polyoxypropylene to polyoxyethylene weight ratio between 20/80 and 80/20 and a polyoxypropylene molecular weight range of 2000 to 3000 daltons; between about 0.001 % to about 0.05% (w/v) of a triquaternary phosphate ester; between about 0.1 % to about 0.9% (w/v) of a neutral, water-soluble salt; between about 0.05% to about 0.10% (w/v) of a chelating agent such as disodium edentate; between about 0.1 % to about 0.4% (w/v) of a buffering agent
- HEC hydroxyethylcellulose
- the resulting cleaning and disinfecting solution has superior cleaning capability and greatly improved anti-microbial activity due to what is believed to be a potentiating reaction between the non-ionic surfactant and the triquatemary phosphate ester anti-microbial agent.
- the present invention is also directed to a method of cleaning, disinfecting, and rinsing contact lenses comprising the steps of mixing a non-ionic surfactant of polyoxyethylene/polyoxypropylene block copolymer having a molecular weight range between about 2500 to 13,000 daltons, a polyoxypropylene to polyoxyethylene weight ratio between 20/80 and 80/20 and a polyoxypropylene molecular weight range of 2000 to 3000 daltons; and an anti-microbial agent preferably of triquatemary phosphate ester.
- a contact lens is then contacted with the solution for a sufficient length of time so that the lens is cleaned, disinfected, and rinsed.
- the present invention is directed to a new and improved cleaning, disinfecting, and rinsing solution for contact lenses which exhibits superior cleaning capability and greatly improved anti-microbial activity. More specifically, the unexpected effect of potentiation between the non-ionic surfactant and the anti-microbial agent makes this solution extremely effective in killing S. marcescens (ATCC 14041 ).
- the present invention is further directed to an effective method of cleaning, disinfecting, and rinsing contact lenses in a single step.
- the present invention can be readily employed with all contact lenses such as conventional hard, soft, gas permeable and silicone lenses. However, it is preferably employed with soft contact lenses such as those commonly referred to as hydrogel lenses prepared by monomers such as hydroxyethylmethacrylate, hydroxyethylmethyl methacrylate, vinylpyrrolidone, glyceromethacrylate, methacrylate or acid esters and the like.
- the present invention involves a new and improved solution for cleaning, disinfecting, and rinsing contact lenses comprising an unique combination of a non-ionic surfactant and a triquatemary phosphate ester anti-microbial agent.
- a family of surfactants of non-ionic nature has been employed in the present invention.
- a suitable family of surfactants for the present invention can be obtained commercially from the BASF Corporation under the trade name of Pluronic ® surfactants.
- This family of block copolymers can be generally described as polyoxyethylene/polyox ⁇ propylene condensation polymers terminated in primary hydroxyl groups. They are synthesized by first creating a hydrophobe of desired molecular weight by the controlled addition of propylene oxide to the two hydroxyl groups of propylene glycol.
- ethylene oxide is added to sandwich this hydrophobe between h ⁇ drophile groups where the length of the hydrophile molecules are controlled to constitute between 10% to 80% by weight of the final weight of the molecule.
- This family of surfactants may be represented by the empirical formula
- Oxide Oxide Oxide Oxide Oxide where the surfactants may exist in liquid, paste or solid form depending on the molecular weight and the composition ratio of hydrophile (polyoxyethylene) to hydrophobe (polyoxypropylene).
- surfactants having lower molecular weights were found to be more efficient cleaning agents.
- a molecular weight range between about 2500 to 13,000 daltons is a suitable range for our invention.
- Specific examples of Pluronic ® surfactants are satisfactory: L64, F68, F87, F88, F98, P65, P75, P84, P85, P104, and P105.
- the surfactants of the present invention have a molecular weight of 2500-13,000 daltons, a hydrophobe/hydrophile ratio range of 80/20 to 20/80 and a hydrophobe molecular weight ranging from about 2000-3000 daltons.
- the physical properties of these Pluronic ® surfactants are listed in Table I.
- a suitable concentration range for the Pluronic ® surfactants in order to produce satisfactory cleaning is generally 0.01 to 10% (w/v) and preferably between about 0.1 % to about 1 .0% (w/v).
- the molecular weight of the surfactant should fall in between about 2500 to about 13,000 daltons (preferably 3400 to 6500) and the composition ratio between polyoxypropylene to polyoxyethylene is between about 20/80 to about 80/20 and preferably 40/60 to 60/40.
- composition ratio we mean the ratio of the weight of polyoxypropylene to the weight of polyoxyethylene contained in the surfactant.
- the molecular weight of the polyoxypropylene ranges from 2000 to 3000 daltons, preferably 2330 to 2750 daltons.
- Pluronic ® P65, P75 and P85 all have a composition ratio of 50/50 for polyoxypropylene/polyoxyethylene. There is an equal amount of hydrophile and hydrophobe in these surfactants.
- Another Pluronic ® surfactant P84 employed in the present invention has a polyoxypropylene to polyoxyethylene ratio of 80/20. It is reasonable to believe that other surfactants having a polyoxypropylene to polyoxyethylene appropriate ratio should work equally well in our invention.
- the hydrophobe content is too high, i.e., above 80%, or the molecular weight of the surfactant is above 13,000 daltons, the surfactant becomes too cytotoxic to be used in a lens care solution.
- the hydrophobe concentration is too low, i.e., below 20%, or the molecular weight of the surfactant is below 2500 daltons, the cleaning efficiency of the solution is believed to be reduced. It is also important that the molecular weight of the polyoxypropylene be between about 2000 and about 3000 daltons.
- the preferred and optimal composition of hydrophobe/hydrophile in the surfactant of the present invention is between about 80/20 to about 20/80, and 50/50, respectively.
- Another significant aspect of the present invention is the preferred use of a specific microbicidal agent of a triquatemary phosphate ester of cocoamidopropyl PG dimonium chloride phosphate.
- This triquatemary phosphate ester is commercially available as Phospholipid ® PTC (previously known as Monaquat ® PTC) supplied by Mona Industries.
- Phospholipid ® PTC previously known as Monaquat ® PTC
- This triquatemary phosphate ester has good, broad spectrum in its anti-bacteria properties. Unlike other quaternary ammonium compounds, it also has considerable anti-fungal activity in the concentration range of about 100 to about 300 ppm calculated as active solids.
- the anti-fungal activity of the triquatemary phosphate ester makes it potentially useful when combined with other preservatives such as WSCP (water soluble cationic polymer), etc., to provide full spectrum microbicidal activity with reduced cytotoxicity.
- WSCP water soluble cationic polymer
- Pluronic ® P85 is added, a sufficient improvement in the microbicidal activity is achieved.
- the presently useful water soluble cationic polymers preferably have the following repeating unit
- R 1 # R 4 and R ⁇ are each independently selected from alkylene radicals containing 1 to about 6 carbon atoms
- R 2 , R 3 , R 5 and R 7 are each independently selected from alkyl radicals containing 1 to about 6 carbon atoms
- each A " is independently selected from ophthalmically acceptable anions
- x is the number of repeating units in the polymer and is an integer in the range of about
- WSCP poly [oxyethylene (dimethyliminio) ethylene - (dimethyliminio) ethylene dichloride]
- WSCP disinfecting agents are commercially available from Buckman Laboratories, Inc. and are described in U.S. Patent No. 4,250,269 which is incorporated herein by reference.
- Monaquat ® PTC may be empirically represented by the formula CH 3 0
- R C 5 ⁇ C 17 Alkyl
- Monaquat ® PTC offers excellent substantivity, lubricity and feel to human hair and skin. It is adequately described in U.S. Patent No. 4,209,449 which is incorporated herein by reference.
- Phospholipid ® PTC is a synthetic, vegetable derived multicationic phospholipid complex. It can be obtained from Mona Industries, Inc. of Paterson, New Jersey. Its CTFA description is cocamidopropyl PG-Dimonium chloride phosphate with the formula:
- Another disinfecting agent is the poly quaternary amine Croquat L. Croquat
- Croquat L is a quaternary ammonium substituted polypeptide which is based on a collagen hydrolysate of relatively low molecular weight, includes lauryl trimethyl ammonium chloride groups and has a molecular weight in the range of 500 to about 5000.
- Croquat L is commercially available from Croda, inc.
- the solution should be formulated to contain the same salt concentration as that present in human body fluids.
- a neutral, water-soluble salt of sodium chloride is employed for this purpose.
- Other neutral, water-soluble salts such as potassium chloride may also be suitably used.
- the solution in the present invention also contains a salt of ethylenediamine tetraacetate such as disodium EDTA.
- This salt is useful as a chelating agent and also as an anti-microbial aid.
- Other salts suitable for the present invention are sodium hexametaphosphate, sodium citrate, and other chelating agents.
- buffering agents are used in the present invention to adjust pH value of the solution at a desirable level of 8 or below.
- a preferred level of pH in the present invention is between about 6.9 and about 7.9.
- the buffering agents used are boric acid and sodium borate.
- Other similar acids including, but not limited to, tricine may be suitably used to bring the pH value of the solution to a desired level. It is also believed that the borate buffer facilitates antifungal activity.
- a viscosity-enhancing agent is also employed in the present invention to bring the viscosity of the solution to a desirable value to provide cushioning of the contact lens in the eye and thus improving comfort to the wearer.
- a desirable viscosity-enhancing agent for the present invention is HEC
- hydroxyethyl cellulose (hydroxyethyl cellulose).
- Other polymeric cellulosic material such as hydroxyethyl methyl cellulose or polymeric non-ionic thickeners such as HPMC
- hydroxypropyl methylcellulose HPC(hydroxypropyl cellulose)andPVA(polyvinyl acetate, with buffers other than the boric acid system) may also be suitably used.
- EXAMPLE 1 A cleaning, disinfecting, and rinsing solution for contact lenses is prepared with the following composition.
- HEC 0.50% (w/v) EXAMPLE 2 A new and improved cleaning, disinfecting, and rinsing solution is prepared by the following composition.
- Example 2 This solution is similar to that in Example 1 except the content of EDTA is doubled. As will be shown later in Table II, it has improved microbicidal activity against S. marcescens at 6 hours and against A. fumigatus at 4 hours.
- EXAMPLE 3 A new and improved cleaning, disinfecting, and rinsing solution for contact lenses is formulated by the following composition:
- Phospholipid ® PTC was increased from 0.03% to 0.035%.
- EXAMPLE 4 A cleaning and disinfecting solution for contact lenses is formulated by the composition:
- This example is similar to that in Example 4 except that the content of Phospholipid ® PTC is increased from 0.035% to 0.04%.
- a cleaning, disinfecting, and rinsing solution for contact lenses is formulated by the composition:
- EXAMPLE 6 This example is a commercially available lens care solution supplied by ICN Corporation under the trade name of Unicare Green ® . It has the following composition:
- This commercial product uses Pluronic ® F127 instead of P85 used in the present invention and HPMC (hydroxypropyl methyl cellulose) instead of HEC used in the present invention.
- A. niger was conducted. This standard log reduction test is expressed in the units of log reduction in a number of contaminating organisms. A ten-fold reduction in the number of contaminating organisms is a one-log reduction. For example, reducing a contamination level of 1 ,000,000 organisms to 100,000 organisms is a one-log reduction. Reducing a contamination level of 10,000 organisms to 1 ,000 organisms is also a one-log reduction. It is desired based on worldwide preservation and disinfection criteria that after six hours exposure to the disinfection solution, the bacteria should be reduced by at least three logs and the fungi should be reduced by at least one log. It should be noted that this test is a log reduction from a six-log challenge. Therefore, a requirement for a three-log reduction means that the solution must be able to reduce a challenge of 10 6 organisms to 10 3 organisms in the required time period.
- the results after 6 hours achieved by the present invention is a 4.9 log reduction when compared to a 1 .9 log reduction achieved by the Unicare Green ® product.
- the 3 log difference represents that the disinfecting function of the present invention is 1 ,000 times more effective than the Unicare Green ® solution in the killing of S. marcescens bacteria.
- the use of the non-ionic surfactants of the present invention greatly potentiated the microbicidal activity of the anti-microbial agent used. See Table III below which shows use of the surfactants of the present invention (Entry Nos. 1 -4, 6, 7 and 9) having superior microbicidal activity against S. marcescens than those outside the present invention (Entry Nos. 5 and 8).
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Procédé d'utilisation et composition d'une solution de nettoyage, de désinfection et de rinçage de lentilles de contact contenant un tensio-actif non ionique, un ester de phosphate triquaternaire, de l'édétate de disodium et d'autres additifs. Le tensio-actif non ionique est un copolymère bloc de polyoxypropylène et de polyoxyéthylène qui, quand on le mélange avec l'ester de phosphate triquaternaire, produit un effet potentialisé en ce qui concerne son activité antimicrobienne dans le traitement de S. marcescens. La solution obtenue possède des caractéristiques nettoyantes et antimicrobiennes considérablement améliorées, ainsi qu'une cytotoxicité basse.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8628293A | 1993-07-01 | 1993-07-01 | |
| US86282 | 1993-07-01 | ||
| PCT/US1994/007347 WO1995001414A1 (fr) | 1993-07-01 | 1994-06-29 | Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaire |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0724622A1 true EP0724622A1 (fr) | 1996-08-07 |
Family
ID=22197525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94923277A Withdrawn EP0724622A1 (fr) | 1993-07-01 | 1994-06-29 | Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaire |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0724622A1 (fr) |
| JP (1) | JPH08512145A (fr) |
| AU (1) | AU7319394A (fr) |
| WO (1) | WO1995001414A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8093352B2 (en) | 2008-08-05 | 2012-01-10 | Alcon Research, Ltd. | Polyalkylene oxide polyquaternary ammonium biocides |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995027515A1 (fr) * | 1994-04-11 | 1995-10-19 | Allergan | Conservation aux phospholipides de compositions contenant du peroxyde d'hydrogene |
| ES2162115T3 (es) * | 1995-12-08 | 2001-12-16 | Kao Corp | Composicion germicida. |
| US5746972A (en) * | 1996-11-01 | 1998-05-05 | Allergan | Compositions and methods for disinfecting and cleaning contact lenses |
| JP3883739B2 (ja) * | 1998-05-22 | 2007-02-21 | 株式会社メニコン | コンタクトレンズ用殺菌液 |
| IT1306123B1 (it) * | 1999-04-02 | 2001-05-30 | Technopharma Sa | Soluzione oftalmica viscosizzata con azione detergente sulle lenti acontatto. |
| MY128134A (en) | 2000-09-28 | 2007-01-31 | Novartis Ag | Compositions and methods for cleaning contact lenses |
| JP4255656B2 (ja) | 2001-09-17 | 2009-04-15 | 株式会社メニコン | 眼科用液剤及びコンタクトレンズ用液剤 |
| US6701940B2 (en) | 2001-10-11 | 2004-03-09 | S. C. Johnson & Son, Inc. | Hard surface cleaners containing ethylene oxide/propylene oxide block copolymer surfactants |
| US20050118132A1 (en) * | 2003-12-01 | 2005-06-02 | Erning Xia | Nonionic surfactant containing compositions for cleaning contact lenses |
| US20080275030A1 (en) | 2007-01-19 | 2008-11-06 | Sveinbjorn Gizurarson | Methods and Compositions for the Delivery of a Therapeutic Agent |
| AR066901A1 (es) * | 2007-05-18 | 2009-09-23 | Alcon Mfg Ltd | Composiciones fodfolipidicas para elcuidado de lentes de contacto y conservacion de composiciones farmaceuticas |
| WO2009113161A1 (fr) | 2008-03-12 | 2009-09-17 | 株式会社メニコン | Composition de solution pour des lentilles de contact |
| KR20160123400A (ko) * | 2008-05-28 | 2016-10-25 | 알콘 리서치, 리미티드 | 자기보존 에멀젼 |
| WO2021156623A1 (fr) * | 2020-02-07 | 2021-08-12 | Ocutec Limited | Emballage optimisé pour lentilles de contact |
| WO2022030421A1 (fr) * | 2020-08-03 | 2022-02-10 | 株式会社シード | Solution de lentilles de contact et son utilisation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB724600I5 (fr) * | 1968-04-26 | |||
| US4356100A (en) * | 1979-05-10 | 1982-10-26 | Sherman Laboratories, Inc. | Soft contact lens cold disinfectant solution |
| US4510065A (en) * | 1982-06-01 | 1985-04-09 | Sherman Laboratories, Inc. | Soft contact lens preservative system, prophylactic cleaner and method |
| NL8502002A (nl) * | 1985-07-11 | 1987-02-02 | Icn Pharmaceuticals | Contactlensvloeistof. |
| AU2426688A (en) * | 1987-08-03 | 1989-03-01 | Interface Research Corporation | Microbiocidal cleansing of disinfectant formulations and preparation therof |
| ES2086393T3 (es) * | 1989-01-31 | 1996-07-01 | Ciba Geigy Ag | Composicion desinfectante y de limpieza. |
| US5089053A (en) * | 1989-11-09 | 1992-02-18 | Polymer Technology Corporation | Contact lens cleaning material and method |
| US5252246A (en) * | 1992-01-10 | 1993-10-12 | Allergan, Inc. | Nonirritating nonionic surfactant compositions |
-
1994
- 1994-06-29 EP EP94923277A patent/EP0724622A1/fr not_active Withdrawn
- 1994-06-29 AU AU73193/94A patent/AU7319394A/en not_active Abandoned
- 1994-06-29 JP JP7503625A patent/JPH08512145A/ja active Pending
- 1994-06-29 WO PCT/US1994/007347 patent/WO1995001414A1/fr not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9501414A1 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8093352B2 (en) | 2008-08-05 | 2012-01-10 | Alcon Research, Ltd. | Polyalkylene oxide polyquaternary ammonium biocides |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995001414A1 (fr) | 1995-01-12 |
| AU7319394A (en) | 1995-01-24 |
| JPH08512145A (ja) | 1996-12-17 |
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