WO2018134776A1 - Preservative free shampoo compositions - Google Patents
Preservative free shampoo compositions Download PDFInfo
- Publication number
- WO2018134776A1 WO2018134776A1 PCT/IB2018/050337 IB2018050337W WO2018134776A1 WO 2018134776 A1 WO2018134776 A1 WO 2018134776A1 IB 2018050337 W IB2018050337 W IB 2018050337W WO 2018134776 A1 WO2018134776 A1 WO 2018134776A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- shampoo composition
- composition
- shampoo
- surfactants
- mixtures
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 239000002453 shampoo Substances 0.000 title claims abstract description 69
- 239000003755 preservative agent Substances 0.000 title claims abstract description 36
- 230000002335 preservative effect Effects 0.000 title claims abstract description 33
- 239000004094 surface-active agent Substances 0.000 claims abstract description 27
- 229960000699 terbinafine hydrochloride Drugs 0.000 claims abstract description 26
- 229940043810 zinc pyrithione Drugs 0.000 claims abstract description 23
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000004088 foaming agent Substances 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000002562 thickening agent Substances 0.000 claims abstract description 15
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical group C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims abstract description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- -1 lauramido Chemical group 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940057950 sodium laureth sulfate Drugs 0.000 claims description 4
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 229940073507 cocamidopropyl betaine Drugs 0.000 claims description 3
- 229940098691 coco monoethanolamide Drugs 0.000 claims description 3
- 229920006037 cross link polymer Polymers 0.000 claims description 3
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 3
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 claims description 3
- 229940113124 polysorbate 60 Drugs 0.000 claims description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 3
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims description 3
- MQFYRUGXOJAUQK-UHFFFAOYSA-N 2-[2-[2-(2-octadecanoyloxyethoxy)ethoxy]ethoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCCCCCCCCCCCCC MQFYRUGXOJAUQK-UHFFFAOYSA-N 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 229960003237 betaine Drugs 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 229940031728 cocamidopropylamine oxide Drugs 0.000 claims description 2
- 229940079868 disodium laureth sulfosuccinate Drugs 0.000 claims description 2
- YGAXLGGEEQLLKV-UHFFFAOYSA-L disodium;4-dodecoxy-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOC(=O)CC(C([O-])=O)S([O-])(=O)=O YGAXLGGEEQLLKV-UHFFFAOYSA-L 0.000 claims description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 claims description 2
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 claims description 2
- 229920001206 natural gum Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 claims 2
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000008118 PEG 6000 Substances 0.000 claims 1
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims 1
- 229940043264 dodecyl sulfate Drugs 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 208000001840 Dandruff Diseases 0.000 abstract description 9
- 208000003251 Pruritus Diseases 0.000 abstract description 4
- 206010039792 Seborrhoea Diseases 0.000 abstract description 4
- 230000007803 itching Effects 0.000 abstract description 4
- 210000004761 scalp Anatomy 0.000 abstract description 4
- 208000008742 seborrheic dermatitis Diseases 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical group Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 13
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 7
- 229960002026 pyrithione Drugs 0.000 description 7
- XMAYWYJOQHXEEK-ZEQKJWHPSA-N (2S,4R)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@H]1O[C@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-ZEQKJWHPSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229960002722 terbinafine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
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- QELSKZZBTMNZEB-UHFFFAOYSA-N p-hydroxybenzoic acid propyl ester Natural products CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 3
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- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- KUZLAYSZNFYDFT-PQBRBDCOSA-L [Na+].[Na+].CCCCCCCC\C=C/CCCCCCCC(=O)NCC(C)OC(=O)C(CC([O-])=O)S([O-])(=O)=O Chemical compound [Na+].[Na+].CCCCCCCC\C=C/CCCCCCCC(=O)NCC(C)OC(=O)C(CC([O-])=O)S([O-])(=O)=O KUZLAYSZNFYDFT-PQBRBDCOSA-L 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
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- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- YRUKXDOALJRQDE-UHFFFAOYSA-N barium(2+) 1-oxidopyridine-2-thione Chemical compound [Ba++].[O-]n1ccccc1=S.[O-]n1ccccc1=S YRUKXDOALJRQDE-UHFFFAOYSA-N 0.000 description 1
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- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000004161 brilliant blue FCF Substances 0.000 description 1
- 229940055580 brilliant blue fcf Drugs 0.000 description 1
- DHAZIUXMHRHVMP-UHFFFAOYSA-N butyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCC DHAZIUXMHRHVMP-UHFFFAOYSA-N 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- YSWAWAYOPDDQJN-UHFFFAOYSA-N cadmium(2+);1-oxidopyridine-2-thione Chemical compound [Cd+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S YSWAWAYOPDDQJN-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- QQQMUBLXDAFBRH-UHFFFAOYSA-N dodecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)O QQQMUBLXDAFBRH-UHFFFAOYSA-N 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
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- 239000013022 formulation composition Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 229940100463 hexyl laurate Drugs 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940033357 isopropyl laurate Drugs 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 229940089474 lamisil Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 210000004995 male reproductive system Anatomy 0.000 description 1
- 229940039092 medicated shampoos Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 229940078812 myristyl myristate Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- OXGBCSQEKCRCHN-UHFFFAOYSA-N octadecan-2-ol Chemical compound CCCCCCCCCCCCCCCCC(C)O OXGBCSQEKCRCHN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- BOWVQLFMWHZBEF-KTKRTIGZSA-N oleoyl ethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229940096792 quaternium-15 Drugs 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 201000003875 tinea corporis Diseases 0.000 description 1
- 201000005882 tinea unguium Diseases 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/58—Metal complex; Coordination compounds
Definitions
- the present invention relates to preservative free, aqueous shampoo compositions of terbinafine hydrochloride and zinc pyrithione. Methods of preparing such compositions are also provided.
- Terbinafine a synthetic allylamine is commonly used to treat fungal infection. Terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase to result in destruction of the fungal cell wall.
- Chemically, terbinafine hydrochloride is (E)- N-(6,6-dimethyl-2-hepten-4- ynyl)- N-methyl- 1 -naphthalenemethanamine hydrochloride.
- the empirical formula is C21H26CIN with a molecular weight of 327.90 and the following structural formula:
- Terbinafine hydrochloride is a white to off-white fine crystalline powder. It is freely soluble in methanol and methylene chloride, soluble in ethanol and slightly soluble in water.
- terbinafine hydrochloride such as LAMISIL
- Oral administration of terbinafine hydrochloride may be used in the treatment of onychomycosis.
- Available topical formulations of terbinafine base or terbinafine hydrochloride in the form of cream or gel or ointment are for superficial skin infections such as jock itch (tinea cruris), athlete's foot (tinea pedis), and other types of ringworm (tinea corporis).
- Polyvalent metal salts of pyrifhione are known to be effective antimicrobial agents and are widely used as fungicides and bactericides in products such as antifouling paints and sealants, building products, plastics and goods made therefrom, polyurethane products, textiles, cosmetics, and in anti- dandruff shampoos.
- the polyvalent metal salts of pyrithione are only sparingly soluble in water and include magnesium pyrithione, strontium pyrithione, barium pyrithione, copper pyrithione, zinc pyrithione, zirconium pyrithione, cadmium pyrithione, and bismuth pyrithione.
- the mostly used divalent pyrithione salts are zinc pyrithione and copper pyrithione.
- Zinc pyrithione has been widely used in anti-dandruff shampoo preparation.
- Shampoo is a hair care product, typically in the form of a viscous liquid that is used for cleansing hair.
- Shampoos are a mixture of various types of surfactants which impart different characteristics to the final product.
- a shampoo contains a base surfactant(s) for cleansing, a foaming agent, a conditioning agent, small amounts of chelating agents, viscosity and pH adjusters, preservatives, fragrance, miscellaneous "nutritive" ingredients, and water.
- US5456851 discloses an aqueous shampoo composition that contains ketoconazole, a surfactant, a foaming agent, thickener sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps at room temperature, preservative, butylated hydroxytoluene or butylated hydroxyanisole, and acid, base or buffer sufficient to give the final composition a pH in the range of from about 4 to about 10.
- W09729733 discloses compositions for body and hair cleansing products, in particular shampoos, comprising one or more fungal ergosterol biosynthesis inhibiting antifungals as a first active ingredient and a pyrithione salt as a second active ingredient.
- shampoo ingredients comprise one or more of a surfactant, a foaming agent, a thickener, a preservative, an anti-oxidant, and acid or base or buffer sufficient to give the shampoo a pH in the range of from about 4 to about 10.
- a shampoo is usually a good medium to support microbial growth. Since most surfactants used in the manufacture of shampoos are sold as aqueous solutions or pastes, which are rarely more than 40% (w/w) on the active basis, they will support microbial growth and are frequently preserved with trace levels of formaldehyde by the supplier.
- the foaming agent and conditioning agents also provide a good nitrogen source to the microbes in the aqueous environment of the shampoo and present a challenge to selection of an effective preservative system.
- Parabens are cost-effective and provide protection against micro-organisms for an extended period of time. While there are multiple types of parabens; methyl, propyl and butylparaben are the most frequently used in shampoo products. In recent years, concern has increased as to their role in producing potentially serious health side effects. For example, accelerate skin ageing process, interfere with male reproductive system and endocrine system, play a role in development of breast cancer etc. There remains, therefore, an unmet need for a preservative free, aqueous shampoo composition.
- compositions of terbinafine hydrochloride and zinc pyrithione In an attempt to develop a novel preservative free, aqueous shampoo compositions of terbinafine hydrochloride and zinc pyrithione, the present inventors have surprisingly found that use of one or more solubilizers, one or more surfactants and one or more foaming agents, one or more thickening agents resulted in compositions, which are stable, does not support microbial growth and, therefore is self-preserving without the addition of traditional preservative, and exhibit efficacy comparable to antifungal compositions currently available in the market.
- the compositions of the present invention are also having smooth conditioning effect.
- Such preservative free, aqueous shampoo composition of present invention may be used for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
- the present specification relates to a preservative free, aqueous shampoo composition of terbinafine hydrochloride and zinc pyrithione and its process for preparation.
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to use of preservative free, aqueous shampoo composition for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
- the present specification relates to a preservative free, aqueous shampoo composition of terbinafine hydrochloride and zinc pyrithione and its process for preparation.
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the present specification relates to a preservative free, aqueous shampoo composition
- a preservative free, aqueous shampoo composition comprising:
- the term "preservative free” means that the composition is substantially free of preservatives.
- the composition being substantially free of preservative means that: the composition is free of preservative; or, if the composition contains preservative, the level of preservative is very low.
- the level of preservative, if included by any means is 0.5 % or less, preferably 0.1 % or less, more preferably 0.05 % or less of the composition.
- the composition of the present invention is substantially free of suitable preservatives commonly used in conventional shampoo preparation, e.g. methylparaben, propylparaben, butylparaben, ethylparaben, imidazolidinyl urea, phenoxy ethanol, quaternium 15.
- terbinafine hydrochloride includes terbinafine or any pharmaceutically acceptable salts or esters or derivatives thereof.
- the amount of terbinafine hydrochloride employed in the shampoo composition is in the range of 0.01% to 5% (w/w), 0.1% to 2% (w/w) of total composition, e.g. 1 % (w/w).
- pyrithione includes pyrithione or any pharmaceutically acceptable salts or esters or derivatives thereof, e.g. zinc pyrithione.
- the amount of zinc pyrithione employed in the shampoo composition is in the range of 0.1% to 5% (w/w), 0.1 % to 2% (w/w) of total composition, e.g. 1% (w/w).
- solubilizers refers to component that helps in solubilization of terbinafine hydrochloride.
- Suitable solubilizers include hexylene glycol, propylene glycol, polyethylene glycol or mixtures thereof.
- Preferred solubilizer includes propylene glycol.
- the amount of solubilizers employed in the composition is in the range of 1% to 20% (w/w) of total composition, e.g. 3% (w/w), 5% (w/w).
- Suitable surfactants for use in the shampoos of the present specification may include sodium C 14-16 olefin sulfonates, sodium lauryl sulfate, TEA lauryl sulfate, sodium laureth sulfate (or sodium lauryl ether sulfate), polysorbate 60, polysorbate 80, cocamidopropylamine oxide, lauryl amine oxide, lauramido DEA, cocamidopropyl betaine, lauryl dimethyl betaine, cocodimethyl sulfo-propyl betaine, sodium cocoyl sarcosinate, disodium oleamido MIPA sulfosuccinate, disodium cocamido MIPA sulfosuccinate, disodium laureth sulfosuccinate, cocoamphocarboxy- glycinate, disodium oleamido MEA sulfosuccinate, amine glycinates, amine prop
- a mixture of two or more different surfactants in particular sodium laureth sulfate and sodium cocoyl sarcosinate, or sodium lauryl sulfate, sodium laureth sulfate, TEA lauryl sulfate and cocamidopropyl betaine, may be used in the present shampoos.
- the total amount of surfactants may range from about 30% to about 45% (w/w).
- the term 'MEA' signifies a mono- ethanolamide of formula RCO-NH-CH2CH2-OH
- the term 'DEA' signifies di-ethanol amide of formula RCO- N(CH2CH2-OH)2
- TEA' signifies triethanolammonium
- the term 'MIPA' signifies a mono- isopropanol amide of formula RCO-NH-CH2-CHOH-CH3
- each RCO-group is a fatty acid residue, such as a Ci3-i9alkylcarbonyl or Ci3-i9alkenylcarbonyl group.
- foaming agents refers to a substance that facilitates formation of foam.
- Suitable foaming agents for use in the shampoos of the present specification may be selected from the group of fatty acid mono-and dialkanol-amides comprising cocamide MEA, cocamide DEA, oleamide MEA, oleamide DEA and mixtures thereof.
- the foaming agent may be present in a range from about 1 to about 20 % (w/w), preferably from about 1 to about 15 % (w/w), in particular about 5 to about 15 % (w/w). These ingredients typically also have a thickening effect on the formulation.
- thickening agents refers to a substance that increases the viscosity of the composition.
- suitable thickeners include carboxylic acid polymers like carbomers (e.g. Carbopol.RTM. 954), acrylates/vinyl neodecanoate crosspolymer (e.g. Aculyn 38) natural gums (e.g. guar, xanthum), cellulose derivatives (e.g. carboxy methylcellulose, methyl cellulose), PEG 6,000, PEG 120, cocomonoethanolamide, PEG-150-Distearate, sodium chloride, ammonium chloride, polyvinyl alcohol and mixtures thereof.
- carboxylic acid polymers like carbomers (e.g. Carbopol.RTM. 954), acrylates/vinyl neodecanoate crosspolymer (e.g. Aculyn 38) natural gums (e.g. guar, xanthum), cellulose derivatives (e.g. carboxy methyl
- the thickening agent may be present in a range from about 1 to about 10 % (w/w), preferably from about 1 to about 5 % (w/w), in particular about 2 to about 5 % (w/w).
- the shampoo compositions of the present specification may further comprise a conditioner such as polyquaternium-7, polyquaternium-10 or a similar cationic quaternary polymer, e.g.
- a quaternary silicone polymer a quaternary silicone polymer ; one or more pearlizing agents selected from the group consisting of behenic acid, ethylene glycol monostearate, ethylene glycol distearate, calcium stearate, 1,2- propylene glycol distearate, 1,2-1,3- and 1,4-butylene glycol distearate and mixtures thereof; and/or one or more fragrances and one or more colorants.
- the shampoo compositions of the present specification may further comprise an emollient.
- Suitable emollients include, for example, stearyl alcohol, glyceryl monooleate, glyceryl monoricinoleate, glyceryl monostearate, cetyl alcohol, ispropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, cetyl palmitate, dimethylpolysiloxane, di-n-butyl sebacate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, sesame oil, coconut oil, arachis oil, castor oil, acetylated lanolin alcohol
- the pH of the shampoo compositions of the present specification are conveniently established using dermatologically acceptable acids, bases and buffers.
- the pH can range from about 4 to about 10, but preferably is in the range of about 5 to about 8, in particular from about 6.3 to about 7.5.
- the shampoo compositions of the present specification may include one or more antioxidants.
- the antioxidant may be selected from DL-alpha-tocopherol, butylhydroxy toluene (BHT), butylhydroxy anisole (BHA), ascorbyl palmitate, ascorbic acid, propyl gallate, or mixtures thereof.
- BHT butylhydroxy toluene
- BHA butylhydroxy anisole
- the amount of antioxidant employed in the composition is in the range of 0.01 to about 0.5% (w/w) of total composition, e.g. 0.07% (w/w), or 0.09% (w/w).
- the shampoo compositions of the present specification can be prepared by various formulation and mixing techniques or methods known in the art for preparing shampoo compositions. For example; mixture of surfactants, foaming agents, thickeners are heated to 70-75°C to form the surfactant phase. Terbinafine is dissolved in the solvents and added to the surfactant phase.
- Aqueous phase is prepared by mixing Zinc pyrithione and purified water followed by addition of conditioning agents, preservative and fragrance. The aqueous phase is added to the surfactant phase with continuous stirring.
- the shampoo compositions of present specification may be used for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
- the shampoo compositions of present specification were subjected to accelerated and long term stability studies.
- aqueous phases were prepared by dispersing zinc pyrithione, polyquaternium 10, brilliant blue FCF, fragrance midnight jasmin in water separately.
- Surfactant phase was prepared by taking cetyl alcohol, coco mono ethanol amide, polysorbate 60, cocoamido propyl betaine and sodium lauryl ether sulfate/sodium laryl sulfate into a manufacturing vessel. Heat the bulk to 70-75 ° C under stirring with anchor speed at 10 - 15 RPM. Continue stirring until a uniform liquid dispersion is obtained.
- pH of the bulk dispersion was adjusted within 10% sodium hydroxide solution to get the desired pH (6.3-6.7).
- the self-preservation efficacy of the preservative free shampoo compositions according to the present specification were evaluated through microbiological examination.
- the test shampoo composition was prepared in accordance with Example 2 and was evaluated in a microbial enumeration test by pour plate method and test for specified microorganisms by direct inoculation method as per protocol set forth by USP. The results are shown in the Table 1. According to the observations, the shampoo composition inhibited the growth of all microorganisms tested.
- Table 1 Microbial enumeration test for specified microorganism
- P. aeruginosa Must be absent in 1 g Absent
- the stability of the preservative free shampoo compositions of present specification were evaluated through accelerated stability studies.
- the composition prepared according to the formula and process of Example 2 was subjected to stability study at various temperature and humidity conditions.
- the composition was found to be chemically stable under accelerated conditions.
- Table 2 presents the stability study data.
- Dandruff is a common disease caused by Malassezia species especially Malassezia furfur.
- Anti- dandruff efficacy of the preservative free shampoo compositions according to the present specification were evaluated through time kill kinetics study and compared with the reference products (Nizoral Shampoo and Scalpe Shampoo). The study was performed using the test and the reference product on Malassezia furfur, the test organism.
- the culture media, sabouraud dextrose broth was inoculated with the test organism and the test and reference products were also diluted tol :10. The concentration of test organism in the media and the products was maintained same in all the cases.
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Abstract
The invention relates to a stable, preservative free, aqueous shampoo compositions of terbinafine hydrochloride and zinc pyrithione, the compositions comprising one or more solubilizers, one or more surfactants and one or more foaming agents, one or more thickening agents. Methods of preparing such compositions are also provided. The present invention further relates to use of terbinafine hydrochloride and zinc pyrithione shampoo compositions for the treatment and prevention of itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
Description
PRESERVATIVE FREE SHAMPOO COMPOSITIONS
FIELD OF THE INVENTION
The present invention relates to preservative free, aqueous shampoo compositions of terbinafine hydrochloride and zinc pyrithione. Methods of preparing such compositions are also provided.
BACKGROUND OF THE INVENTION
Terbinafine, a synthetic allylamine is commonly used to treat fungal infection. Terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase to result in destruction of the fungal cell wall. Chemically, terbinafine hydrochloride, is (E)- N-(6,6-dimethyl-2-hepten-4- ynyl)- N-methyl- 1 -naphthalenemethanamine hydrochloride. The empirical formula is C21H26CIN with a molecular weight of 327.90 and the following structural formula:
Terbinafine hydrochloride is a white to off-white fine crystalline powder. It is freely soluble in methanol and methylene chloride, soluble in ethanol and slightly soluble in water.
The prior art discloses oral and topical formulations of terbinafine hydrochloride, such as LAMISIL, which is marketed by Novartis. Oral administration of terbinafine hydrochloride may be used in the treatment of onychomycosis. Available topical formulations of terbinafine base or terbinafine hydrochloride in the form of cream or gel or ointment are for superficial skin infections such as jock itch (tinea cruris), athlete's foot (tinea pedis), and other types of ringworm (tinea corporis).
Polyvalent metal salts of pyrifhione (commonly known as l-hydroxy-2-pyridinethione; 2- pyridinethiol- 1 -oxide; 2-pyridinethione; 2-mercaptopyridine-N-oxide; pyridinethione; and pyridinethione-N-oxide) are known to be effective antimicrobial agents and are widely used as fungicides and bactericides in products such as antifouling paints and sealants, building products, plastics and goods made therefrom, polyurethane products, textiles, cosmetics, and in anti- dandruff shampoos.
The polyvalent metal salts of pyrithione are only sparingly soluble in water and include magnesium pyrithione, strontium pyrithione, barium pyrithione, copper pyrithione, zinc pyrithione, zirconium pyrithione, cadmium pyrithione, and bismuth pyrithione. The mostly used divalent pyrithione salts are zinc pyrithione and copper pyrithione. Zinc pyrithione has been widely used in anti-dandruff shampoo preparation.
Shampoo is a hair care product, typically in the form of a viscous liquid that is used for cleansing hair. Shampoos are a mixture of various types of surfactants which impart different characteristics to the final product. In general, a shampoo contains a base surfactant(s) for cleansing, a foaming agent, a conditioning agent, small amounts of chelating agents, viscosity and pH adjusters, preservatives, fragrance, miscellaneous "nutritive" ingredients, and water.
Prior art shampoos comprising anti-dandruff agents are designed in such a way that an optimum balance is achieved between efficacy and tolerability; the concentration of the active ingredient in the medicated shampoos is such that as many users as possible are effectively treated and as few as possible suffer adverse effects.
US5456851 discloses an aqueous shampoo composition that contains ketoconazole, a surfactant, a foaming agent, thickener sufficient to give the final formulation a viscosity in the range of about 4,000 to about 9,000 cps at room temperature, preservative, butylated hydroxytoluene or butylated hydroxyanisole, and acid, base or buffer sufficient to give the final composition a pH in the range of from about 4 to about 10.
W09729733 discloses compositions for body and hair cleansing products, in particular shampoos, comprising one or more fungal ergosterol biosynthesis inhibiting antifungals as a first active ingredient and a pyrithione salt as a second active ingredient. Also disclosed shampoo ingredients comprise one or more of a surfactant, a foaming agent, a thickener, a preservative, an anti-oxidant, and acid or base or buffer sufficient to give the shampoo a pH in the range of from about 4 to about 10.
Due to the nature of the composition, a shampoo is usually a good medium to support microbial growth. Since most surfactants used in the manufacture of shampoos are sold as aqueous solutions or pastes, which are rarely more than 40% (w/w) on the active basis, they will support microbial growth and are frequently preserved with trace levels of formaldehyde by the supplier. In addition, the foaming agent and conditioning agents also provide a good nitrogen source to the microbes in the aqueous environment of the shampoo and present a challenge to selection of an effective preservative system.
Parabens are cost-effective and provide protection against micro-organisms for an extended period of time. While there are multiple types of parabens; methyl, propyl and butylparaben are the most frequently used in shampoo products. In recent years, concern has increased as to their role in producing potentially serious health side effects. For example, accelerate skin ageing process, interfere with male reproductive system and endocrine system, play a role in development of breast cancer etc. There remains, therefore, an unmet need for a preservative free, aqueous shampoo composition.
In an attempt to develop a novel preservative free, aqueous shampoo compositions of terbinafine hydrochloride and zinc pyrithione, the present inventors have surprisingly found that use of one or more solubilizers, one or more surfactants and one or more foaming agents, one or more thickening agents resulted in compositions, which are stable, does not support microbial growth and, therefore is self-preserving without the addition of traditional preservative, and exhibit efficacy comparable to antifungal compositions currently available in the market. The compositions of the present invention are also having smooth conditioning effect. Such
preservative free, aqueous shampoo composition of present invention may be used for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
SUMMARY OF THE INVENTION
The present specification relates to a preservative free, aqueous shampoo composition of terbinafine hydrochloride and zinc pyrithione and its process for preparation.
In one aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) one or more solubilizers,
(iv) one or more surfactants, and
(v) one or more foaming agents.
In another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) one or more solubilizers,
(iv) one or more surfactants,
(v) one or more foaming agents, and
(vi) one or more thickening agents.
In yet another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) proplylene glycol,
(iv) one or more surfactants, and
(v) one or more foaming agents.
In yet another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) 0.1 % to 5 % (w/w) terbinafine hydrochloride,
(ii) 0.05% to 2 % (w/w) zinc pyrithione,
(iii) 1% to 10% (w/w) one or more solubilizers,
(iv) one or more surfactants,
(v) one or more foaming agents, and
(vi) one or more thickening agents.
In yet another aspect, the present specification relates to use of preservative free, aqueous shampoo composition for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
DESCRIPTION OF THE INVENTION
The present specification relates to a preservative free, aqueous shampoo composition of terbinafine hydrochloride and zinc pyrithione and its process for preparation.
In one aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) one or more solubilizers,
(iv) one or more surfactants, and
(v) one or more foaming agents.
In another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) one or more solubilizers,
(iv) one or more surfactants,
(v) one or more foaming agents, and
(vi) one or more thickening agents.
In yet another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) proplylene glycol,
(iv) one or more surfactants, and
(v) one or more foaming agents.
In yet another aspect, the present specification relates to a preservative free, aqueous shampoo composition comprising:
(i) 0.1 % to 5 % (w/w) terbinafine hydrochloride,
(ii) 0.05% to 2 % (w/w) zinc pyrithione,
(iii) 1% to 10% (w/w) one or more solubilizers,
(iv) one or more surfactants,
(v) one or more foaming agents, and
(vi) one or more thickening agents.
As used herein, the term "preservative free" means that the composition is substantially free of preservatives. In the present invention, "the composition being substantially free of preservative" means that: the composition is free of preservative; or, if the composition contains preservative, the level of preservative is very low. In the present invention, the level of preservative, if included by any means, is 0.5 % or less, preferably 0.1 % or less, more preferably 0.05 % or less of the composition. The composition of the present invention is substantially free of suitable preservatives commonly used in conventional shampoo preparation, e.g. methylparaben,
propylparaben, butylparaben, ethylparaben, imidazolidinyl urea, phenoxy ethanol, quaternium 15.
As used herein, the term "terbinafine hydrochloride" includes terbinafine or any pharmaceutically acceptable salts or esters or derivatives thereof. The amount of terbinafine hydrochloride employed in the shampoo composition is in the range of 0.01% to 5% (w/w), 0.1% to 2% (w/w) of total composition, e.g. 1 % (w/w).
As used herein, the term "pyrithione" includes pyrithione or any pharmaceutically acceptable salts or esters or derivatives thereof, e.g. zinc pyrithione. The amount of zinc pyrithione employed in the shampoo composition is in the range of 0.1% to 5% (w/w), 0.1 % to 2% (w/w) of total composition, e.g. 1% (w/w).
As used herein, the term "solubilizers" refers to component that helps in solubilization of terbinafine hydrochloride. Suitable solubilizers include hexylene glycol, propylene glycol, polyethylene glycol or mixtures thereof. Preferred solubilizer includes propylene glycol. The amount of solubilizers employed in the composition is in the range of 1% to 20% (w/w) of total composition, e.g. 3% (w/w), 5% (w/w).
Suitable surfactants for use in the shampoos of the present specification may include sodium C 14-16 olefin sulfonates, sodium lauryl sulfate, TEA lauryl sulfate, sodium laureth sulfate (or sodium lauryl ether sulfate), polysorbate 60, polysorbate 80, cocamidopropylamine oxide, lauryl amine oxide, lauramido DEA, cocamidopropyl betaine, lauryl dimethyl betaine, cocodimethyl sulfo-propyl betaine, sodium cocoyl sarcosinate, disodium oleamido MIPA sulfosuccinate, disodium cocamido MIPA sulfosuccinate, disodium laureth sulfosuccinate, cocoamphocarboxy- glycinate, disodium oleamido MEA sulfosuccinate, amine glycinates, amine propionates and amine sultaines, and mixtures thereof.
Preferably, a mixture of two or more different surfactants , in particular sodium laureth sulfate and sodium cocoyl sarcosinate, or sodium lauryl sulfate, sodium laureth sulfate, TEA lauryl sulfate and cocamidopropyl betaine, may be used in the present shampoos. In the shampoos
according to the present invention, the total amount of surfactants may range from about 30% to about 45% (w/w).
In the above definitions, and hereinafter, the term 'MEA' signifies a mono- ethanolamide of formula RCO-NH-CH2CH2-OH, the term 'DEA' signifies di-ethanol amide of formula RCO- N(CH2CH2-OH)2, TEA' signifies triethanolammonium ; the term 'MIPA' signifies a mono- isopropanol amide of formula RCO-NH-CH2-CHOH-CH3 ; wherein each RCO-group is a fatty acid residue, such as a Ci3-i9alkylcarbonyl or Ci3-i9alkenylcarbonyl group.
As used herein, the term "foaming agents" refers to a substance that facilitates formation of foam. Suitable foaming agents (foam boosters and stabilizers) for use in the shampoos of the present specification may be selected from the group of fatty acid mono-and dialkanol-amides comprising cocamide MEA, cocamide DEA, oleamide MEA, oleamide DEA and mixtures thereof. The foaming agent may be present in a range from about 1 to about 20 % (w/w), preferably from about 1 to about 15 % (w/w), in particular about 5 to about 15 % (w/w). These ingredients typically also have a thickening effect on the formulation.
As used herein, the term "thickening agents" refers to a substance that increases the viscosity of the composition. Suitable thickeners include carboxylic acid polymers like carbomers (e.g. Carbopol.RTM. 954), acrylates/vinyl neodecanoate crosspolymer (e.g. Aculyn 38) natural gums (e.g. guar, xanthum), cellulose derivatives (e.g. carboxy methylcellulose, methyl cellulose), PEG 6,000, PEG 120, cocomonoethanolamide, PEG-150-Distearate, sodium chloride, ammonium chloride, polyvinyl alcohol and mixtures thereof.
Since shampoo users expect a shampoo to be slightly viscous, one or more thickeners are often included in the formulation which gives it a viscosity in the range of 5,000 to 55,000 cps at room temperature. Other suitable thickeners are the foaming agents mentioned hereinabove, preferably cocamide MEA. The thickening agent may be present in a range from about 1 to about 10 % (w/w), preferably from about 1 to about 5 % (w/w), in particular about 2 to about 5 % (w/w).
The shampoo compositions of the present specification may further comprise a conditioner such as polyquaternium-7, polyquaternium-10 or a similar cationic quaternary polymer, e.g. a quaternary silicone polymer ; one or more pearlizing agents selected from the group consisting of behenic acid, ethylene glycol monostearate, ethylene glycol distearate, calcium stearate, 1,2- propylene glycol distearate, 1,2-1,3- and 1,4-butylene glycol distearate and mixtures thereof; and/or one or more fragrances and one or more colorants.
The shampoo compositions of the present specification may further comprise an emollient. Suitable emollients include, for example, stearyl alcohol, glyceryl monooleate, glyceryl monoricinoleate, glyceryl monostearate, cetyl alcohol, ispropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, cetyl palmitate, dimethylpolysiloxane, di-n-butyl sebacate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, sesame oil, coconut oil, arachis oil, castor oil, acetylated lanolin alcohols, petroleum, mineral oil, butyl myristate, isostearic acid, palmitic acid, isopropyl linoieate, lauryl lactate, myristyl lactate, decyl oleate, myristyl myristate, and mixture thereof.
The pH of the shampoo compositions of the present specification are conveniently established using dermatologically acceptable acids, bases and buffers. The pH can range from about 4 to about 10, but preferably is in the range of about 5 to about 8, in particular from about 6.3 to about 7.5.
The shampoo compositions of the present specification may include one or more antioxidants. The antioxidant may be selected from DL-alpha-tocopherol, butylhydroxy toluene (BHT), butylhydroxy anisole (BHA), ascorbyl palmitate, ascorbic acid, propyl gallate, or mixtures thereof. The amount of antioxidant employed in the composition is in the range of 0.01 to about 0.5% (w/w) of total composition, e.g. 0.07% (w/w), or 0.09% (w/w).
The shampoo compositions of the present specification can be prepared by various formulation and mixing techniques or methods known in the art for preparing shampoo compositions. For example; mixture of surfactants, foaming agents, thickeners are heated to 70-75°C to form the
surfactant phase. Terbinafine is dissolved in the solvents and added to the surfactant phase. Aqueous phase is prepared by mixing Zinc pyrithione and purified water followed by addition of conditioning agents, preservative and fragrance. The aqueous phase is added to the surfactant phase with continuous stirring.
The shampoo compositions of present specification may be used for treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea.
The shampoo compositions of present specification were subjected to accelerated and long term stability studies.
The specification will now be described in greater detail by reference to the following non- limiting examples.
EXAMPLES
Process:
1. Terbinafine hydrochloride was dissolved in a mixture of propylene glycol/hexylene glycol and butylated hydroxytoluene.
2. Multiple aqueous phases were prepared by dispersing zinc pyrithione, polyquaternium 10, brilliant blue FCF, fragrance midnight jasmin in water separately.
3. Surfactant phase was prepared by taking cetyl alcohol, coco mono ethanol amide, polysorbate 60, cocoamido propyl betaine and sodium lauryl ether sulfate/sodium laryl
sulfate into a manufacturing vessel. Heat the bulk to 70-75 ° C under stirring with anchor speed at 10 - 15 RPM. Continue stirring until a uniform liquid dispersion is obtained.
4. Terbinafine hydrochloride and different aqueous phases were added sequentially to the surfactant phase prepared in Step 3 with constant stirring.
5. Acrylates/vinyl neodecanoate crosspolymer/carboxy methyl cellulose was added into manufacturing vessel manually under stirring at 15± 5 RPM and mix for 15± 5 Minutes.
6. pH of the bulk dispersion was adjusted within 10% sodium hydroxide solution to get the desired pH (6.3-6.7).
Microbial Enumeration Test:
The self-preservation efficacy of the preservative free shampoo compositions according to the present specification were evaluated through microbiological examination. The test shampoo composition was prepared in accordance with Example 2 and was evaluated in a microbial enumeration test by pour plate method and test for specified microorganisms by direct inoculation method as per protocol set forth by USP. The results are shown in the Table 1. According to the observations, the shampoo composition inhibited the growth of all microorganisms tested.
Table 1 : Microbial enumeration test for specified microorganism
Test Parameter Limit Observation
Total Aerobic Microbial
Not more than 100 CFU / g < 100 CFU/g Count (TAMC)
Total Combined Yeast and
Not more than 10 CFU / g < 10 CFU/g
Moulds Count (TYMC)
P. aeruginosa Must be absent in 1 g Absent
S. aureus Must be absent in 1 g Absent
Stability study
The stability of the preservative free shampoo compositions of present specification were evaluated through accelerated stability studies. The composition prepared according to the formula and process of Example 2, was subjected to stability study at various temperature and humidity conditions. The composition was found to be chemically stable under accelerated conditions. Table 2 presents the stability study data.
Table 2: Stability data for Example2 formulation composition
Time Kill kinetics study
Dandruff is a common disease caused by Malassezia species especially Malassezia furfur. Anti- dandruff efficacy of the preservative free shampoo compositions according to the present specification were evaluated through time kill kinetics study and compared with the reference products (Nizoral Shampoo and Scalpe Shampoo). The study was performed using the test and the reference product on Malassezia furfur, the test organism. The culture media, sabouraud dextrose broth was inoculated with the test organism and the test and reference products were also diluted tol :10. The concentration of test organism in the media and the products was maintained same in all the cases. Sampling was done at different time points from the culture flasks and incubated at 35°C±2°C on the sabouraud dextrose agar media via filter paper for 48 h
to 72 h. The filter paper was observed for the presence or absence of growth. The number of CFUs on the filter paper was determined only if the count was <100 CFU. >100 CFU was depicted as "Growth" (G) and absence of CFUs on the filter paper was represented as "No growth" (NG). The test shampoo products exhibited time kill kinetics similar to the reference products at 1 :10 dilution.
Table 2: Time kill kinetics results
Test/ CFU
Reference
Products Dilution 2 5 8 10 30 60 120 180 240 300 24 hr min min min min min min min min min min
Test
1 :10 NG NG NG NG NG NG NG NG NG NG NG
Terbinafinel %
& ZPTO 1 %
Sclape
Shampoo
1 :10 NG NG NG NG NG NG NG NG NG NG NG
(Ketoconazole
2% & ZPTO
1 %)
Nizoral
Shampoo
1 :10 NG NG NG NG NG NG NG NG NG NG NG
(Ketoconazole
1 %)
Claims
1. A preservative free, aqueous shampoo composition comprising:
(i) terbinafine hydrochloride,
(ii) zinc pyrithione,
(iii) one or more solubilizers,
(iv) one or more surfactants, and
(v) one or more foaming agents.
2. The shampoo composition as claimed in claim 1 , wherein the solubilizers are selected from one or more of he xylene glycol, propylene glycol, polyethylene glycol or mixtures thereof.
3. The shampoo composition as claimed in claim 2, wherein the solubilizer is propylene glycol.
4. The shampoo composition as claimed in claim 1, wherein the surfactants are selected from one or more of sodium lauryl sulfate, triethanolamide lauryl sulfate, sodium laureth sulfate, polysorbate 60, cocamidopropylamine oxide, lauryl amine oxide, lauramido diethanol amide, cocamidopropyl betaine, lauryl dimethyl betaine, cocodimethyl sulfo-propyl betaine, sodium cocoyl sarcosinate, disodium oleamido monoisopropanol amide sulfosuccinate, disodium cocamido mono-isopropanol amide sulfosuccinate, disodium laureth sulfosuccinate, cocoamphocarboxy-glycinate, disodium oleamido monoethanolamide sulfosuccinate, amine glycinates, amine propionates and amine sultaines, or mixtures thereof.
5. The shampoo composition as claimed in claim 1, wherein the foaming agents are selected from one or more of cocamide monoethanolamide, cocamide diethanolamide, oleamide monoethanolamide, oleamide diethanolamide or mixtures thereof.
6. The shampoo composition as claimed in claim 1, wherein the composition further comprises thickening agents selected from one or more of carbomers, acrylates/vinyl neodecanoate crosspolymer, natural gums, cellulose derivatives, PEG 6000, PEG 120, cocomonoethanolamide,
PEG-150-Distearate, sodium chloride, ammonium chloride, polyvinyl alcohol or mixtures thereof.
7. The shampoo composition as claimed in claim 1 , wherein the composition further comprises a conditioner.
8. The shampoo composition as claimed in claim 1, wherein pH of the composition is in the range of about 5-8.
9. The shampoo composition as claimed in claim 1, comprising:
(i) 0.1 % to 5 % (w/w) terbinafine hydrochloride,
(ii) 0.05% to 2 % (w/w) zinc pyrithione,
(iii) 1% to 10% (w/w) one or more solubilizers,
(iv) one or more surfactants, and
(v) one or more foaming agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EA201991712A EA201991712A1 (en) | 2017-01-19 | 2018-01-19 | COMPOSITIONS OF CERTAINLY FREE SHAMPOOS |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201741002114 | 2017-01-19 | ||
| IN201741002114 | 2017-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2018134776A1 true WO2018134776A1 (en) | 2018-07-26 |
Family
ID=62908408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2018/050337 WO2018134776A1 (en) | 2017-01-19 | 2018-01-19 | Preservative free shampoo compositions |
Country Status (2)
| Country | Link |
|---|---|
| EA (1) | EA201991712A1 (en) |
| WO (1) | WO2018134776A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997029733A1 (en) * | 1996-02-16 | 1997-08-21 | Janssen Pharmaceutica N.V. | Compositions containing an antifungal and a sulfur compound |
| WO2013093823A2 (en) * | 2011-12-20 | 2013-06-27 | Vyome Biosciences Pvt Ltd | Topical oil composition for the treatment of fungal infections |
| WO2014167554A2 (en) * | 2013-04-12 | 2014-10-16 | Vyome Biosciences Pvt. Ltd. | Composition and formulation of antimicrobial agents, processes thereof and methods for treating microbial infections |
-
2018
- 2018-01-19 WO PCT/IB2018/050337 patent/WO2018134776A1/en active Application Filing
- 2018-01-19 EA EA201991712A patent/EA201991712A1/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997029733A1 (en) * | 1996-02-16 | 1997-08-21 | Janssen Pharmaceutica N.V. | Compositions containing an antifungal and a sulfur compound |
| WO2013093823A2 (en) * | 2011-12-20 | 2013-06-27 | Vyome Biosciences Pvt Ltd | Topical oil composition for the treatment of fungal infections |
| WO2014167554A2 (en) * | 2013-04-12 | 2014-10-16 | Vyome Biosciences Pvt. Ltd. | Composition and formulation of antimicrobial agents, processes thereof and methods for treating microbial infections |
Also Published As
| Publication number | Publication date |
|---|---|
| EA201991712A1 (en) | 2020-01-14 |
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