JP4852231B2 - 1,2−アルカンジオールの相乗的混合物 - Google Patents
1,2−アルカンジオールの相乗的混合物 Download PDFInfo
- Publication number
- JP4852231B2 JP4852231B2 JP2003568970A JP2003568970A JP4852231B2 JP 4852231 B2 JP4852231 B2 JP 4852231B2 JP 2003568970 A JP2003568970 A JP 2003568970A JP 2003568970 A JP2003568970 A JP 2003568970A JP 4852231 B2 JP4852231 B2 JP 4852231B2
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- JP
- Japan
- Prior art keywords
- mixture
- polyethylene glycol
- acid
- diol
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000036559 skin health Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940102544 sodium laureth-13 carboxylate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- 229940075560 sodium lauryl sulfoacetate Drugs 0.000 description 1
- 229940048109 sodium methyl cocoyl taurate Drugs 0.000 description 1
- BCISDMIQYBCHAT-UHFFFAOYSA-M sodium;2-(dodecanoylamino)ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCC(=O)NCCS([O-])(=O)=O BCISDMIQYBCHAT-UHFFFAOYSA-M 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- UAJTZZNRJCKXJN-UHFFFAOYSA-M sodium;2-dodecoxy-2-oxoethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)CS([O-])(=O)=O UAJTZZNRJCKXJN-UHFFFAOYSA-M 0.000 description 1
- WOMWZQPEGPZTPN-UHFFFAOYSA-N sodium;undec-10-enamide Chemical compound [Na].[Na].NC(=O)CCCCCCCCC=C WOMWZQPEGPZTPN-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 229940098760 steareth-2 Drugs 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960002871 tenoxicam Drugs 0.000 description 1
- LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 210000004906 toe nail Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class 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
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- 239000001841 zingiber officinale Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- 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
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
-
- 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
- A61K2800/59—Mixtures
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
−毒性学的に許容でき、
−皮膚により良好に許容され、
−安定であり(特に通常の化粧品および/もしくは医薬調製物中で)、
−実質的にかつ好ましくは完全に無臭であり、そして
−安価に調製することができ(すなわち、標準の方法を使用してそして/もしくは標準の前駆体から出発して)
なければならないことを考慮しなければならない。
1.最強の個々の作用を有する、5〜10C原子の範囲内の鎖長をもつ直鎖1,2−アルカンジオールの決定、
2.5〜10C原子の範囲内の鎖長を有する他の直鎖1,2−アルカンジオールそれぞれとの、最強の個々の作用をもつ1,2−アルカンジオールの組み合わせ、
3.最強の抗菌作用をもつ第2項に従う組み合わせの決定、
において、すべての考えられる組み合わせ物から特に適した組み合わせ物を選択することができる。
(a)体臭を引き起こす微生物の美容的処理のために、
(b)アクネを引き起こす微生物の美容的処理のために、
(c)真菌症を引き起こす微生物の美容的処理のために、そして
(d)無生物質(inanimate material)上もしくはその中の微生物の処理のために
使用することもできる。本発明に従う混合物は多数のグラム−陽性菌、グラム−陰性菌、カビおよび酵母菌に対してそれらの相乗作用をもたらす。大腸菌(Escherichia coli)および緑膿菌(Pseudomonas aeruginosa)のようなグラム−陰性菌に対し、鵞口瘡カンジダ(Candida albicans)のような酵母菌に対し、そして黒色アスペルギルス(Aspergillus niger)のような真菌に対して特に優れた作用がある。これに関しては、抑制が非常に困難なカビの黒色アスペルギルスに対する本発明に従う1,2−ジオール混合物の非常に優れた作用は、出願者自身の研究により5〜10C原子の範囲内の鎖長を有する個別の1,2−ジオールが使用される時にそれらのCFU値を0の値に減少させることができないことが示されたので、特に有利であると見なされる。
例えば不飽和脂肪酸のような、体内で生産され、汗中に含まれる物質のバクテリアによる分解の結果として、身体の快適性に重大な影響を有することができる不快な臭いをもつ分解産物が多少弱い臭いを有する前駆体から形成される。化粧品においては、身体の汗の形成を抑制する製品(いわゆる制汗剤)もしくは臭い形成の原因であるヒトの皮膚のバクテリアの生長を妨げる物質(消臭剤)を使用して体臭の原因である物質の形成を妨げる。表皮ブドウ球菌、コリネバクテリウム・キセロシスおよび表皮ブレビバクテリウムのようなバクテリアの種は概括的に腋下および足臭もしくは体臭の形成に決定的な原因である。従って、化粧品産業において、様々な体臭(腋下および足臭を含む)を引き起こす微生物の処理のための新規物質の必要がいまだ存在する。
(a)それらの鎖長が(i)異なり、かつ(ii)それぞれが5〜10C原子の範囲内にある、2種、3種もしくは4種以上の直鎖1,2−アルカンジオールの混合物および
(b)前記混合物と相溶性の賦形剤、
を含んで成る対応する抗菌組成物、並びに更に
(c)抗菌活性化合物として、それらの鎖長が(i)異なり、かつ(ii)それぞれが5〜10C原子の範囲内にある、2種、3種もしくは4種以上の直鎖1,2−アルカンジオールの混合物、
および
(a)前記混合物と相溶性の賦形剤、および更に場合によっては、
(b)直鎖1,2−アルカンジオールを含まない更なる抗菌活性化合物
を含んで成る抗菌組成物、に関する。
−セラミド、ここでセラミドは角質層の保水能を明らかに改善するN−アシルスフィンゴシン(スフィンゴシンの脂肪酸アミド)もしくはこれらの脂質の合成類似体(いわゆる疑似−セラミド)であると理解される、
−リン脂質、例えば大豆レシチン、卵レシチンおよびセファリン、
−ワセリン、パラフィンおよびシリコーン油、後者はとりわけジアルキル−およびアルキルアリール−シロキサン、例えばジメチルポリシロキサンおよびメチルフェニルポリシロキサン並びにそれらのアルコキシル化および第四級化誘導体を含む、
が含まれる。
−水もしくは水溶液、
−脂肪油、脂肪、ワックス並びに他の天然および合成脂肪物質、好ましくは低C数を有するアルコール、例えばイソプロパノール、プロピレングリコールもしくはグリセロールとの脂肪酸のエステル、または低C数を有するアルカン酸ともしくは脂肪酸との脂肪アルコールのエステル、
−低C数を有するアルコール、ジオールもしくはポリオール並びにそれらのエーテル、好ましくは、エタノール、イソプロパノール、プロピレングリコール、グリセロール、エチレングリコール、エチレングリコールモノエチルもしくはモノブチルエーテル、プロピレングリコールモノメチル、モノエチルもしくはモノブチルエーテル、ジエチレングリコールモノメチルもしくはモノエチルエーテルおよび類似製品、
であることができる。とりわけ前記の溶媒の混合物が使用される。アルコール性溶媒の場合には水が更なる成分であることができる。
・アニオン界面活性剤、
・カチオン界面活性剤、
・両性界面活性剤および
・非イオン性界面活性剤。
A.アニオン界面活性剤
有利に使用することができるアニオン界面活性剤は下記である、
アシルアミノ酸(およびそれらの塩)、例えば、
−アシルグルタミン酸塩、例えば、ナトリウムアシルグルタメート、ジ−TEA−パルミトイルアスパルテートおよびナトリウムカプリル/カプリングルタメート、
−アシルペプチド、例えば、パルミトイル−加水分解乳汁タンパク質、ナトリウムココイル−加水分解大豆タンパク質およびナトリウム/カリウムココイル−加水分解コラーゲン、
−サルコシネート、例えば、ミリストイルサルコシン、TEA−ラウロイルサルコシネート、ナトリウムラウロイルサルコシネートおよびナトリウムココイルサルコシネート、
−タウリン酸塩、例えば、ナトリウムラウロイルタウレートおよびナトリウムメチルココイルタウレート、
−アシルラクチレート、ラウロイルラクチレート、カプロイルラクチレート、
−アラニネート、
カルボン酸および誘導体、例えば、
−例えば、ラウリン酸、ステアリン酸アルミニウム、マグネシウムアルカノラートおよびウンデシレン酸亜鉛、
−エステルカルボン酸、例えば、カルシウムステアロイルラクチラート、ラウレス−6シトレートおよびナトリウムPEG−4ラウラミドカルボキシレート、
−エーテル−カルボン酸、例えば、ナトリウムラウレス−13カルボキシレートおよびナトリウムPEG−6ココアミドカルボキシレート、
リン酸エステルおよび塩、例えば、DEA−オレス−10ホスフェートおよびジラウレス−4ホスフェート、
スルホン酸および塩、例えば、
−アシルイセチオネート、例えば、ナトリウム/アンモニウムココイルイセチオネート、
−アルキルアリールスルホネート、
−アルキルスルホネート、例えば、ナトリウムココナツモノグリセリドスルフェート、ナトリウムC12−14オレフィン−スルホネート、ナトリウムラウリルスルホアセテートおよびマグネシウムPEG−3ココアミドスルフェート、
−スルホスクシネート、例えば、ジオクチルナトリウムスルホスクシネート、二ナトリウムラウレス−スルホスクシネート、二ナトリウムラウリルスルホスクシネートおよび二ナトリウムウンデシレンアミドMEA−スルホスクシネート、並びに
硫酸エステル、例えば、
−アルキルエーテルスルフェート、例えばナトリウム、アンモニウム、マグネシウム、MIRA、TIPAラウレススルフェート、ナトリウムミレススルフェートおよびナトリウムC12−13パレススルフェート、
−アルキルスルフェート、例えば、ナトリウム、アンモニウムおよびTEAラウリルスルフェート。
B.カチオン界面活性剤
有利に使用することができるカチオン界面活性剤は下記である。
−アルキルアミン、
−アルキルイミダゾール、
−エトキシル化アミンおよび
−第四級界面活性剤、
RNH2CH2CH2COO−(pH=7において)
RNHCH2CH2COO−B+(pH=12において)B+=任意のカチオン、例えばNa+
−第四級エステル。
C.両性界面活性剤
有利に使用することができる両性界面活性剤は下記である。
−アシル/ジアルキルエチレンジアミン、例えば、ナトリウムアシルアンホアセテート、二ナトリウムアシルアンホジプロピオネート、二ナトリウムアルキルアンホジアセテオート、ナトリウムアシルアンホヒドロキシ−プロピルスルホネート、二ナトリウムアシルアンホジアセテートおよびナトリウムアシルアンホプロピオネート、
−N−アルキルアミノ酸、例えば、アミノプロピルアルキルグルタミド、アルキルアミノプロピオン酸、ナトリウムアルキルイミドジプロピオネートおよびラウロアンホカルボキシグリシネート。
D.非イオン性界面活性剤
有利に使用することができる非イオン性界面活性剤は下記である。
−アルコール、
−アルカノールアミド、例えば、ココアミドMEA/DEA/MIPA、
−酸化アミン、例えば、ココアミドプロピルアミンオキシド、
−酸化エチレン、グリセロール、ソルビタンもしくは他のアルコールとのカルボン酸のエステル化により形成されるエステル、
−エーテル、例えば、エトキシル化/プロポキシル化アルコール、エトキシル化/プロポキシル化エステル、エトキシル化/プロポキシル化グリセロールエステル、エトキシル化/プロポキシル化コレステロール、エトキシル化/プロポキシル化トリグリセリドエステル、エトキシル化/プロポキシル化ラノリン、エトキシル化/プロポキシル化ポリシロキサン、プロポキシル化POEエーテルおよび、ラウリルグルコシド、デシルグリコシドおよびココグリコシドのようなアルキルポリグリコシド、
−蔗糖エステルおよびエーテル、
−ポリグリセロールエステル、ジグリセロールエステル、モノグリセロールエステル、
−メチルグルコースエステル、ヒドロキシ酸のエステル。
−鉱油、鉱物ワックス、
−脂肪油、脂肪、ワックス並びに他の天然および合成脂肪物質、好ましくは低C数を有するアルコール(例えばイソプロパノール、プロピレングリコールもしくはグリセロール)との脂肪酸のエステル、または低C数を有するアルカン酸もしくは脂肪酸との脂肪アルコールのエステル、
−安息香酸アルキル、
−シリコーン油(例えばジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン)およびそれらの混合形態
から選択することができる。
−脂肪アルコールエトキシラート、
−エトキシル化羊毛ワックスアルコール、
−一般式 R−O−(−CH2−CH2−O−)n−R’のポリエチレングリコールエーテル、
−一般式 R−COO−(−CH2−CH2−O−)n−Hの脂肪酸エトキシラート、
−一般式 R−COO−(−CH2−CH2−O−)2−R’のエーテル化脂肪酸エトキシラート、
−一般式 R−COO−(−CH2−CH2−O−)n−C(O)−R’のエステル化脂肪酸エトキシラート、
−ポリエチレングリコールグリセロール脂肪酸エステル、
−エトキシル化ソルビタンエステル、
−コレステロールエトキシラート、
−エトキシル化トリグリセリド、
−一般式 R−COO−(−CH2−CH2−O−)n−OOH(nは5〜30の数を表す)のアルキルエーテルカルボン酸、
−ポリオキシエチレンソルビトール脂肪酸エステル、
−一般式 R−O−(−CH2−CH2−O−)n−SO3−Hのアルキルエーテルスルフェート、
−一般式 R−O−(−CH2−CH(CH3)−O−)n−Hの脂肪アルコールプロポキシラート、
−一般式 R−O−(−CH2−CH(CH3)−O−)n−R’のポリプロピレングリコールエーテル、
−プロポキシル化羊毛ワックスアルコール、
−一般式 R−COO−(−CH2−CH(CH3)−O−)n−R’のエステル化脂肪酸プロポキシラート、
−一般式 R−COO−(−CH2−CH(CH3)−O−)n−C(O)−R’のエステル化脂肪酸プロポキシラート、
−一般式 R−COO−(−CH2−CH(CH3)−O−)n−Hの脂肪酸プロポキシラート、
−プロピレングリコールグリセロール脂肪酸エステル、
−プロポキシル化ソルビタンエステル、
−コレステロールプロポキシラート、
−プロポキシル化トリグリセリド、
−一般式 R−O−(−CH2−CH(CH3)−O−)n−CH2−COOHのアルキルエーテルカルボン酸、
−一般式 R−O−(−CH2−CH(CH3)−O−)n−SO3−Hのアルキルエーテルスルフェートおよびこれらのスルフェートがそれに基づく酸、
−一般式 R−O−Xn−Ym−Hの脂肪アルコールエトキシラート/プロポキシラート、
−一般式 R−O−Xn−Ym−R’のポリプロピレングリコールエーテル、
−一般式 R−COO−Xn−Ym−R’のエステル化脂肪酸プロポキシラート、
−一般式R−COO−Xn−Ym−Hの脂肪酸エトキシラート/プロポキシラート、
を含んで成る群から選択することができる。
ポリエチレングリコール(13)ステアリルエーテル(ステアレス−13)、
ポリエチレングリコール(14)ステアリルエーテル(ステアレス−14)、
ポリエチレングリコール(15)ステアリルエーテル(ステアレス−15)、
ポリエチレングリコール(16)ステアリルエーテル(ステアレス−16)、
ポリエチレングリコール(17)ステアリルエーテル(ステアレス−17)、
ポリエチレングリコール(18)ステアリルエーテル(ステアレス−18)、
ポリエチレングリコール(19)ステアリルエーテル(ステアレス−19)、
ポリエチレングリコール(20)ステアリルエーテル(ステアレス−20)、
ポリエチレングリコール(12)イソステアリルエーテル(イソステアレス−12)、
ポリエチレングリコール(13)イソステアリルエーテル(イソステアレス−13)、
ポリエチレングリコール(14)イソステアリルエーテル(イソステアレス−14)、
ポリエチレングリコール(15)イソステアリルエーテル(イソステアレス−15)、
ポリエチレングリコール(16)イソステアリルエーテル(イソステアレス−16)、
ポリエチレングリコール(17)イソステアリルエーテル(イソステアレス−17)、
ポリエチレングリコール(18)イソステアリルエーテル(イソステアレス−18)、
ポリエチレングリコール(19)イソステアリルエーテル(イソステアレス−19)、
ポリエチレングリコール(20)イソステアリルエーテル(イソステアレス−20)、
ポリエチレングリコール(13)セチルエーテル(セテス−13)、
ポリエチレングリコール(14)セチルエーテル(セテス−14)、
ポリエチレングリコール(15)セチルエーテル(セテス−15)、
ポリエチレングリコール(16)セチルエーテル(セテス−16)、
ポリエチレングリコール(17)セチルエーテル(セテス−17)、
ポリエチレングリコール(18)セチルエーテル(セテス−18)、
ポリエチレングリコール(19)セチルエーテル(セテス−19)、
ポリエチレングリコール(20)セチルエーテル(セテス−20)、
ポリエチレングリコール(13)イソセチルエーテル(イソセテス−13)、
ポリエチレングリコール(14)イソセチルエーテル(イソセテス−14)、
ポリエチレングリコール(15)イソセチルエーテル(イソセテス−15)、
ポリエチレングリコール(16)イソセチルエーテル(イソセテス−16)、
ポリエチレングリコール(17)イソセチルエーテル(イソセテス−17)、
ポリエチレングリコール(18)イソセチルエーテル(イソセテス−18)、
ポリエチレングリコール(19)イソセチルエーテル(イソセテス−19)、
ポリエチレングリコール(20)イソセチルエーテル(イソセテス−20)、
ポリエチレングリコール(12)オレイルエーテル(オレス−12)、
ポリエチレングリコール(13)オレイルエーテル(オレス−13)、
ポリエチレングリコール(14)オレイルエーテル(オレス−14)、
ポリエチレングリコール(15)オレイルエーテル(オレス−15)、
ポリエチレングリコール(12)ラウリルエーテル(ラウレス−12)、
ポリエチレングリコール(12)イソラウリルエーテル(イソラウレス−12)、
ポリエチレングリコール(13)セチルステアリルエーテル(セテアレス−13)、
ポリエチレングリコール(14)セチルステアリルエーテル(セテアレス−14)、
ポリエチレングリコール(15)セチルステアリルエーテル(セテアレス−15)、
ポリエチレングリコール(16)セチルステアリルエーテル(セテアレス−16)、
ポリエチレングリコール(17)セチルステアリルエーテル(セテアレス−17)、
ポリエチレングリコール(18)セチルステアリルエーテル(セテアレス−18)、
ポリエチレングリコール(19)セチルステアリルエーテル(セテアレス−19)、
ポリエチレングリコール(20)セチルステアリルエーテル(セテアレス−20)。
脂肪酸エトキシラートを下記の群から選択することも更に有利である:
ポリエチレングリコール(20)ステアレート、ポリエチレングリコール(21)ステアレート、ポリエチレングリコール(22)ステアレート、ポリエチレングリコール(23)ステアレート、ポリエチレングリコール(24)ステアレート、ポリエチレングリコール(25)ステアレート、
ポリエチレングリコール(12)イソステアレート、ポリエチレングリコール(13)イソステアレート、ポリエチレングリコール(14)イソステアレート、ポリエチレングリコール(15)イソステアレート、ポリエチレングリコール(16)イソステアレート、ポリエチレングリコール(17)イソステアレート、ポリエチレングリコール(18)イソステアレート、ポリエチレングリコール(19)イソステアレート、ポリエチレングリコール(20)イソステアレート、ポリエチレングリコール(21)イソステアレート、ポリエチレングリコール(22)イソステアレート、ポリエチレングリコール(23)イソステアレート、ポリエチレングリコール(24)イソステアレート、ポリエチレングリコール(25)イソステアレート、
ポリエチレングリコール(12)オレエート、ポリエチレングリコール(13)オレエート、ポリエチレングリコール(14)オレエート、ポリエチレングリコール(15)オレエート、ポリエチレングリコール(16)オレエート、ポリエチレングリコール(17)オレエート、ポリエチレングリコール(18)オレエート、ポリエチレングリコール(19)オレエート、ポリエチレングリコール(20)オレエート。
ナトリウムラウレス−11カルボキシレートはエトキシル化アルキルエーテルカルボン酸もしくはその塩として有利に使用することができる。ナトリウムラウレス1〜4スルフェートはアルキルエーテルスルフェートとして有利に使用することができる。ポリエチレングリコール(30)コレステリルエーテルはエトキシル化コレステロール誘導体として有利に使用することができる。ポリエチレングリコール(25)ソヤステロールもまた有用であることが証明された。ポリエチレングリコール(60)ツキミソウグリセリドはエトキシル化トリグリセリドとして有利に使用することができる。
ポリエチレングリコール(20)ソルビタンモノラウレート、
ポリエチレングリコール(20)ソルビタンモノステアレート、
ポリエチレングリコール(20)ソルビタンモノイソステアレート、
ポリエチレングリコール(20)ソルビタンモノパルミテート、
ポリエチレングリコール(20)ソルビタンモノオレエート、
を含んで成る群から選択することもまた有利である。
欧州薬局方に従って適当な保存性試験を実施した。
試験微生物:
以下の微生物株を適当な保存性の試験に使用した:
A:大腸菌 ATCC 8739
B:緑膿菌 ATCC 9027
C:黄色ブドウ球菌 ATCC 6538
D:鵞口瘡カンジダ ATCC 10231
E:黒色アスペルギルス ATCC 16404
最初の微生物数(CFU/g;”0”値)は様々な試験系列において240,000〜300,000の範囲内にあった。
調製物:
適当な保存性の試験のために(a)考慮された可能な相乗的活性混合物および(b)比較の目的のために、対応する非混合1,2−ジオール、をO/Wエマルション中に取り込んだ。
試験された1,2−ジオールおよび1,2−ジオール混合物の保存性負荷試験の結果は表3に与えられる。驚くべきことには、規定された質量比の1,2−ペンタンジオール、1,2−ヘキサンジオール、1,2−オクタンジオールおよび/もしくは1,2−デカンジオールから成る1,2−ジオール混合物は同一濃度で計量された個々の物質よりもずっと大きい活性を有することが見いだされた。これはとりわけ、28日後に残留した残留微生物数において示された。1,2−ペンタンジオールおよび/もしくは1,2−オクタンジオールとの1,2−ヘキサンジオールの2種および3種混合物はここで特に有効であることが判明した。すべての5種の試験微生物(大腸菌、緑膿菌、黄色ブドウ球菌、鵞口瘡カンジダおよび黒色アスペルギルス)の事例において、選択期間中に好ましい目標の0値までコロニー形成単位(CFU)の濃度を減少させることができた。
予備説明:
保存剤としてのそれらの使用に加えて、本発明に従う1,2−ジオール混合物はまた、例えば体臭の原因である微生物の抑制にも適するという所見は、特に関連する微生物の表皮ブドウ球菌、コリネバクテリウム・キセロシスおよび表皮ブレビバクテリウムが試験された試験系列に回帰する。表皮ブドウ球菌、コリネバクテリウム・キセロシスおよび表皮ブレビバクテリウムのMIC値に加えて、本発明に従う相乗的に活性な混合物の対応する相乗性係数をこれらの試験系列において決定した(表7を参照されたい)。
一般的試験条件:
本発明に従う1,2−ジオールおよびジオール混合物の抗菌作用をDIN 58 940/ICSおよびDIN 58 944/ICSに基づいた寒天希釈法の助けを借りて示した。直径9.0cmのペトリ皿に50℃で液体状で維持された、13.5mlの調製したてのMueller−Hinton寒天(Merck,Ref.1.054437もしくはWilkins−Chalgren寒天ブイヨン、Oxoid,Ref.CM 643、10gの寒天/1リットルを補充)を充填し、それに様々な濃度の希釈試料を10%(V/V)=1.5mlで添加した。試験微生物のマラセジア・フルフル(Malassezia furfur)に対しては、3%Tween80(Merck,Ref.8.22 187)を含有するMueller−Hinton寒天を使用した。
1,2−ヘキサンジオール、1,2−オクタンジオールおよび、オクタンジオール1部に対するヘキサンジオール2部の質量比の2種のジオールの混合物に対するMIC値を説明された一般的試験条件に従って決定した(表7を参照されたい)。
(a)1,2−アルカンジオールの相乗的混合物と(b)更なる保存剤の混合物による適切な保存性の試験を欧州薬局方に従って同様に実施した。試験法は実施例1に詳述されている。
試験微生物:
以下の微生物株を適当な保存性の試験に使用した:
A:大腸菌 ATCC 8739
B:緑膿菌 ATCC 9027
C:黄色ブドウ球菌 ATCC 6538
D:鵞口瘡カンジダ ATCC 10231
E:黒色アスペルギルス ATCC 16404
最初の微生物数(CFU/g;”0”値)は様々な試験系列において280,000〜320,000の範囲にあった。
調製物:
適当な保存性の試験のために(a)本発明に従う1,2−ジオール混合物および(b)更なる保存剤から成る、考慮に入れられた活性化合物の潜在的に相乗性の組み合わせ物を一定量でエマルション中に取り込んだ。比較の目的で、本発明に従う対応する1,2−ジオール混合物および試験された更なる保存剤を同様なO/Wエマルション中に別々に取り入れた。
本発明に従う1,2−アルカンジオールおよび更なる保存剤の相乗的混合物から成る、試験された活性化合物の組み合わせ物に対する保存性負荷試験の結果は、例により系1,2−ヘキサンジオール/1,2−オクタンジオール/EuxylK400に対して表9および10に与えられる。驚くべきことには、1,2−ジオール混合物自体のみならずまた、更なる保存剤との1,2−ジオール混合物の組み合わせ物も、同一濃度で計量された個々の物質と比較して活性の有意な相乗的増強を達成することができることが発見された。前記の例において、これはとりわけ28日後に残留した黒色アスペルギルスの残留微生物数において示される。表9で見ることができるように、産業製品の保存において特に問題となる微生物の黒色アスペルギルスの例において、調製物Cを使用することにより28日間で2,800まで微生物数を減少することができた。他方、1%の用量で試験された調製物B(1,2−ヘキサンジオール+1,2−オクタンジオール:質量比1:1)に従うジオール混合物およびこれも対照の目的の0.1%の濃度で試験された調製物A(Euxyl K400を含有)は黒色アスペルギルスの場合のコロニー形成単位(CFU)数においてこのような有意な減少を示すことができなかった。このように試験系列(表9)は例えば、(a)1,2−ペンタンジオール、1,2−ヘキサンジオール、1,2−オクタンジオールおよび1,2−デカンジオールから成る群の少なくとも2種の異なる成員並びに(b)更なる保存剤、から成る活性化合物の混合物が相乗性の更に改善された作用を有することができることを示す。
Claims (8)
- 鎖長が(i)異なり、かつ(ii)それぞれ5〜10C原子の範囲内にある、2種もしくは3種の直鎖1,2−アルカンジオールの抗菌活性混合物であって、1,2−ヘキサンジオールおよび1,2−オクタンジオールの混合物、並びに1,2−ペンタンジオール、1,2−ヘキサンジオールおよび1,2−オクタンジオールの混合物からなる群より選択される、上記混合物。
- 混合物中の前記ジオールの割合が、それらの抗菌作用が相乗的に増強されるように設定されている、請求項1記載の抗菌活性混合物。
- 混合物中の前記ジオールの割合が、それらの黒色アスペルギルスに対する抗菌作用が相乗的に増強されるように設定されている、請求項1または2記載の抗菌活性混合物。
- 各個々のジオールの割合がジオール混合物の総質量に基づいて1〜99%(w/w)の範囲内にある、請求項1〜3のいずれか1項に記載の抗菌活性混合物。
- 直鎖の1,2−アルカンジオールではない抗菌活性化合物を更に含む、請求項1〜4のいずれか1項に記載の抗菌活性混合物。
- 抗菌的に有効量の、請求項1〜5のいずれか1項に記載の抗菌活性混合物を含んでなる、(a)体臭を引き起こす微生物、
(b)アクネを引き起こす微生物および/もしくは
(c)真菌症を引き起こす微生物、
の処理のための局所投与用化粧料および/もしくは医薬組成物。 - (a)無生物質上もしくはその中の微生物の処理のための、または
(b)腐敗性製品の保存のための、
請求項1〜5のいずれか1項に記載の抗菌活性混合物の使用。 - 抗菌的に有効な医薬の調製のための、請求項1〜5のいずれか1項に記載の抗菌活性混合物の使用。
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PCT/EP2002/011611 WO2003069994A1 (de) | 2002-02-19 | 2002-10-17 | Synergistische mischungen von 1,2-alkandiolen |
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- 2002-02-19 DE DE10206759A patent/DE10206759A1/de not_active Withdrawn
- 2002-10-17 US US10/502,132 patent/US7582681B2/en not_active Expired - Lifetime
- 2002-10-17 ES ES02785229T patent/ES2269781T3/es not_active Expired - Lifetime
- 2002-10-17 JP JP2003568970A patent/JP4852231B2/ja not_active Expired - Lifetime
- 2002-10-17 WO PCT/EP2002/011611 patent/WO2003069994A1/de active IP Right Grant
- 2002-10-17 DE DE50208033T patent/DE50208033D1/de not_active Expired - Lifetime
- 2002-10-17 EP EP06114975A patent/EP1731036A1/de not_active Withdrawn
- 2002-10-17 CN CNB028282116A patent/CN100342785C/zh not_active Expired - Lifetime
- 2002-10-17 EP EP02785229A patent/EP1478231B1/de not_active Expired - Lifetime
- 2002-10-17 AU AU2002350557A patent/AU2002350557A1/en not_active Abandoned
- 2002-10-17 AT AT02785229T patent/ATE337703T1/de not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
---|---|
ATE337703T1 (de) | 2006-09-15 |
US7582681B2 (en) | 2009-09-01 |
EP1731036A1 (de) | 2006-12-13 |
CN100342785C (zh) | 2007-10-17 |
JP2005526036A (ja) | 2005-09-02 |
EP1478231A1 (de) | 2004-11-24 |
WO2003069994A1 (de) | 2003-08-28 |
CN1620248A (zh) | 2005-05-25 |
US20050222276A1 (en) | 2005-10-06 |
ES2269781T3 (es) | 2007-04-01 |
DE50208033D1 (de) | 2006-10-12 |
EP1478231B1 (de) | 2006-08-30 |
DE10206759A1 (de) | 2003-08-28 |
AU2002350557A1 (en) | 2003-09-09 |
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