WO1996005807A1 - Detergent compositions - Google Patents

Detergent compositions Download PDF

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Publication number
WO1996005807A1
WO1996005807A1 PCT/JP1995/001658 JP9501658W WO9605807A1 WO 1996005807 A1 WO1996005807 A1 WO 1996005807A1 JP 9501658 W JP9501658 W JP 9501658W WO 9605807 A1 WO9605807 A1 WO 9605807A1
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Prior art keywords
carbon atoms
group
surface active
detergent composition
chain
Prior art date
Application number
PCT/JP1995/001658
Other languages
French (fr)
Inventor
Takashi Matsuo
Yasuo Suzuki
Kumiko Yamada
Kazuyuki Yahagi
Original Assignee
Kao Corporation
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Publication date
Application filed by Kao Corporation filed Critical Kao Corporation
Priority to EP95928634A priority Critical patent/EP0777466A1/en
Publication of WO1996005807A1 publication Critical patent/WO1996005807A1/en

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    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • This invention relates to a detergent composition, which exhibits a high detergency, good foaming properties, and low irritating properties.
  • This invention particularly relates to a detergent composition, which can be stably formulated with a cationic conditioning agent, and which has markedly high rinsing effects and high conditioning effects when it is used for washing hair.
  • a detergent which also has conditioning effects.
  • many cationic substances have heretofore been known.
  • a cationic substance is formulated with a detergent, which contains an anionic surface active agent as the predominant component, a complex of the cationic substance and the anionic surface active agent is formed undesirably. Therefore, it is difficult to formulate the cationic substance with the detergent, which contains an anionic surface active agent as a predominant component, and the problems occur in that, for example, sufficient conditioning effects cannot be obtained.
  • a detergent containing, as the predominant component, a nonionic surface active agent which has lower irritating properties than an anionic surface active agent and can be easily formulated with a cationic conditioning agent.
  • a detergent containing an alkyl saccharide as a nonionic surface active agent a low-irritating detergent composition, which contains an alkyl saccharide-based nonionic surface active agent and a cationic polymer, has been proposed in, for example, Japanese Patent Publication 6-23085.
  • a detergent composition which contains alkyl saccharide type nonionic surface active agent, a sucrose fatty acid ester, and an anionic surface active agent, or an amphoteric surface active agent, has been proposed in, for example, Japanese Patent Publication 6-23086.
  • the alkyl saccharide type nonionic surface active agent is comparatively expensive. Therefore, attempts have also been made in order to formulate a polyoxyethylene alkyl ether type nonionic surface active agent, which is comparatively cheap, with a detergent.
  • the polyoxyethylene alkyl ether type nonionic surface active agent has poor foaming properties and has been rarely used for hair detergents. Only a shampoo composition, which contains an amide-amine type amphoteric surface active agent or an alkylolamide type nonionic surface active agent as the predominant component and contains a polyoxyethylene type surface active agent as an auxiliary component, has been proposed in, for example, Japanese Patent Application 55-25436.
  • a detergent composition which exhibits a high detergency, good foaming properties, and low irritating properties, can be obtained by employing a specific polyoxyethylene alkyl ether type nonionic surface active agent, a betaine type surface active agent, and a specific nonionic surface active agent in combination with one another in a specific ratio.
  • the present invention is based on such findings.
  • the present invention provides a detergent composition comprising:
  • n a number of 11 to 30;
  • R 2 represents a straight-chain or branched alkyl or alkenyl group having 8 to 18 carbon atoms
  • R 3 represents a straight-chain or branched alkyl or alkenyl group having 6 to 18 carbon atoms
  • R 4 represents an alkylene group having 2 to 4 carbon atoms
  • G represents a residue derived from a reducing sugar having 5 or 6 carbon atoms
  • s represents an integer of 0 to 10.
  • t represents a number of 1 to 10
  • R 9 represents a straight-chain or branched alkyl or alkenyl group having 8 to 16 carbon atoms
  • u and v independently represent an integer of 0 to
  • the weight ratio of component (A) to the total of the components (B) and (C), (A)/[(B) + (C)], falls within the range of 1/1 to 10/1.
  • the detergent composition in accordance with the present invention is suitable for a hair detergent and a body detergent, particularly for a hair detergent and a rinse-in shampoo containing a cationic conditioning agent.
  • R 1 in formula (1) which represents a straight-chain or branched alkyl or alkenyl group having 11 to 15 carbon atoms, includes undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, undecenyl, dodecenyl, tridecenyl, te tradecenyl, and pentadecenyl groups.
  • the number of carbon atoms in R 1 is 11 to 15, and n, representing the number of moles of ethylene oxide added, is 11 to 30.
  • Preferred component (A) includes a polyoxyethlene alkyl ether type nonionic surface active agent represented by formula (1) wherein R 1 is a straight-chain or branched alkyl or alkenyl group having 12 to 14 carbon atoms and n is 15 to 25 for obtaining higher foaming properties.
  • the polyoxyethylene alkyl ether type nonionic surface active agent serving as the component (A) is a predominant component of the detergent composition according to the present invention.
  • the polyoxyethylene alkyl ether type nonionic surface active agent is formulated in a proportion falling within the range of 5 to 50% by weight (hereinbelow unless otherwise specified, all the percentages denote "% by weight"), preferably 10 to 50 % by weight, more preferably 10 to 30%, still preferably 10 to 20%, based on the total weight of the detergent composition. If the proportion of the component (A) is smaller than 5%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (A) is larger than 50%, the viscosity of the detergent composition will become high, and it will unfavorably become difficult to formulate other components.
  • the betaine type surface active agent serving as the component (B) for use in the detergent composition according to the present invention may be of the carbobetaine type, the sulfobetaine type, the imidazolinium betaine type, or the like. Preferred among them is a carbobetaine type amphoteric surface active agent represented by formula (8):
  • R 18 represents a straight-chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms, or R 19 CONH(CH 2 ) z - (wherein R 19 represents a straight- chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms, and z represents an integer of 1 to 5);
  • M represents a hydrogen atom, an alkali metal, or triethanolamine; and
  • y represents an integer of 1 to 5, or
  • R 20 represents a straight-chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms; and M and y are as defined above.
  • a carbobetaine type amphoteric surface active agent represented by formula (8), with a fatty acid amide propyl betaine of formula (8) (wherein R 18 represents a group represented by R 19 CONH ( CH 2 ) 3 - ) being most preferred .
  • the betaine type surface active agent serving as the component (B) is formulated in a proportion falling within the range of 1 to 10%, preferably 1 to 5%, more preferably 1 to 3%, based on the total weight of the detergent composition. If the proportion of the component (B) is smaller than 1%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (B) is larger than 10%, the detergent composition unfavorably has increased irritating properties.
  • the nonionic surface active agent serving as the component (C) for use in the detergent composition of the present invention is one or more compounds selected from an alkyldimethylamine oxide of formula (2), an alkyl saccharide of formula (3), a fatty acid monoglyceride of formula (4), or an alkanolamide of formula (5). These nonionic surface active agents will be described below.
  • R 2 formula (2) preferably represents an alkyl group having 10 to 16 carbon atoms, more preferably a decyl, lauryl or myristyl group.
  • R 3 preferably represents an alkyl group having 10 to 14 carbon atoms, more preferably a decyl, dodecyl, or tetradecyl group.
  • R 4 preferably represents an ethylene and propylene group.
  • the chemical structure of G depends on the raw material to be used, such as a monosaccharide, a disaccharide and a higher saccharide, and glucose, galactose and fructose being preferred.
  • s preferably represents an integer of 0 to 2
  • t preferably represents a number of 1 to 2.
  • R 8 preferably represents a straight-chain or branched alkyl or alkenyl group having 8 to 12 carbon atoms.
  • ester bonding has only to be formed at either of the carbon atoms in the glycerin.
  • the ester groups may be located at either of the carbon atoms in the glycerin.
  • R 9 preferably represents a straight-chain or branched alkyl or alkenyl group having 10 to 14 carbon atoms, with straight-chain group having 11 to 13 carbon atoms being still preferred.
  • u and v independently prefer ably represent an integer of 0 to 3.
  • the alkyldimethylamine oxide of formula (2) and the fatty acid monoglyceride of formula (4) are preferred for obtaining enhanced foaming properties.
  • the fatty acid monoglycer ides of formula (4) such as decanoic acid monoglyceride and lauric acid monoglyceride are still preferred.
  • the nonionic surface active agent serving as the component (C) may be used either individually or in combination of two or more of them, with the combination of two or more of them being still preferred for obtaining enhanced foaming properties.
  • the nonionic surface active agent serving as the component (C) is formulated in a proportion falling within the range of 1 to 10%, preferably 1 to 5%, based on the total weight of the detergent composition. If the proportion of the component (C) is lower than 1%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (C) is larger than 10%, the detergent performance will often be impaired.
  • the proportion of the component (A) should be determined so that the weight ratio of the amount of the component (A) to the total amount of the components (B) and (C), i.e. the weight ratio (A)/[ (B) + (C)], may fall within the range of 1/1 to 10/1. If the weight ratio ( A) /[ (B) + (C) ] falls outside this range, the detergent composition cannot exhibit a high detergency, good foaming properties, and low irritating properties simultaneously. It is preferred for obtaining enhanced forming properties that the weight ratio (A)/[ (B)+(C)] falls within the range of 3/2 to 3/1.
  • a cationic conditioning agent to obtain sufficient conditioning effects.
  • the cationic conditioning agents include cationic surface active agents and cationic polymers, with cationic surface active agents of formulae (6) and (7) being preferred for obtaining enhanced conditioning effects.
  • R 10 represents a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms
  • R 11 represents a hydrogen atom, a methyl group, an ethyl group, or a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms
  • R 12 and R 13 independently represent a hydrogen atom, a methyl group, or an ethyl group
  • X- represents a halogen atom or an organic anionic group.
  • R 14 represents a straight-chain or branched alkyl or alkenyl group having 7 to 35 carbon atoms
  • R 15 , R 16 and R 17 independently represent an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms, or a hydrogen atom
  • L represents -CONJ- (wherein J represents a hydrogen atom or an alkyl or hydroxyalkyl group having 1 to 3 Carbon atoms), -O-, or -COO-
  • R 10 represents a straight-chain alkyl group having 14 to 22 carbon atoms
  • R 11 represents a methyl group or an ethyl group
  • R 12 and R 13 independently represent a methyl group or an ethyl group
  • X represents Cl-, Br-, CH 3 OSO 3 - or C 2 H 5 OSP 3 -.
  • R 14 preferably represents a straight-chain or branched alkyl or alkenyl group having 7 to 21 carbon atoms, in particular 11 to 17 carbon atoms; and R 15 , R 16 and R 17 independently preferably represent a methyl or ethyl group; M preferably represents -CONH-; Y preferably represents a hydrogen atom or a hydroxyl group; and Z preferably represents a hydrogen atom or a hydroxyl group.
  • the proportion of the cationic conditioning agent falls within the range of 0.1 to 10 %, preferably 1 to 10%, based on the total weight of the detergent composition. It is still preferred for obtaining higher conditioning effects that the proportion falls within the range of 3 to 8%, based on the total weight of the detergent composition.
  • anionic surface active agents which are conventionally used in detergents in such a proportion that the advantageous effects of the present invention are not impaired.
  • anionic surface active agents include an alkyl sulfate, an alkyl ether sulfate, an alkyl sulfonate, a sulfosuc- cinate, an ⁇ -sulfo fatty acid ester, an ⁇ -olefin sulfonate, a saturated or unsaturated fatty acid ester, a phosphoric acid monoester type surface active agent, and an acylated amino acid.
  • silicone derivatives may be contained in such a proportion that the advantageous effects of the detergent composition in accordance with the present invention may not be impaired. In such cases, a good slip feeling and a dry feeling can be obtained.
  • the silicone derivatives include a dimethylpolysiloxane, a methylphenylpolysiloxane, a polyether-modif ied silicone, an epoxy-modif ied silicone, an alkoxy-modified silicone, and an amino-modified silicone.
  • the detergent composition in accordance with the present invention if desired, other components than the above-enumerated components, which are ordinarily formulated in cosmetic preparations, pharmaceutical preparations, foods, or the like may be added in such a proportion that the advantageous effects of the detergent composition in accordance with the present invention may not be impaired.
  • Such components include an anti-dandruff agent, a bactericide, an anti-inflammation agent, a medicinal agent, an antiseptic, a humectant, such as propylene glycol, glycerol, diethylene glycol monoethyl ether, sorbitol and panthenol, a coloring agent, such as a dye and a pigment; a conditioning agent, such as perfluoro polyether; a pearling agent, a chitosan derivative, such as hydroxypropyl chitosan, a formulated perfume, and components described in "Encyclopedia of Shampoo Ingredients," Micelle Press, 1985 which is incorporated herein by reference.
  • the detergent composition in accordance with the present invention can be produced by a conventional manner and may take on the form of paste, gel or liquid.
  • test shampoo liquid One gram of a test shampoo liquid was applied to 20 g (length: 15 cm) of hairs of a healthy Japanese female, followed by washing for 1 minute and rinsing. The feeling of the hair after rinsing was evaluated by 20 specialized panel members and evaluated according to the following scale.
  • Foaming properties Into a cylinder was introduced 800 ml of aqueous solution of the shampoo diluted in twenty times amount of water (solution temperature 20 oC)C followed by rotation of a stirring blade equipped within the aqueous solution for 5 minutes. Thereafter, the aqueous solution was allowed to stand for 30 seconds, and the degree of foaming was evaluated according to the following scale. The rotation rate of the stirring blade was 1,000 rpm, and the rotation was reversed every five seconds.
  • Skin irritation A conduct of immersing the hands in each shampoo liquid for five minutes and thereafter drying the hands was repeated 10 times by 20 specialized panel members. The degree of irritation to the skin was evaluated according to the following scale. Excellent: 90% or more of the panel members felt that skin irritation was low.
  • Shampoos having the formulation shown in Tables 4 to 6 were prepared by a conventional procedure. Detergency, foaming properties, skin irritation were evaluated as in Example 1. Also, the softness of the hair after drying and the stability of the detergent were evaluated. Softness of the hair after drying and the stability of the detergent were also evaluated by the method described below. The results obtained are shown in Tables 4 to 6.
  • Softness of hair after drying One gram of the shampoo liquid was applied to 20 g of hair (length: 15 cm) of a healthy Japanese female. The shampoo liquid was caused to foam for one minute. The hair was then rinsed with water, dried with a towel, and dried with a dryer. These operations were carried out by 20 specialized panel members, and the softness of the hair after drying was evaluated according to the following scale. Excellent: Very soft and flexible
  • Stability of detergent After preparation of the shampoo, the shampoo was shaken violently, followed by allowing to stand at 20 oC for one week, and then the state of the liquid was observed with naked eyes and evaluated according to the scale.
  • a shampoo having the f ormula t i on shown below was produced by a conventional procedure.
  • the shampoo thus obtained exhibited good detergency, good foaming properties, and low skin irritation.
  • a rinse-in shampoo having the formulation shown below was produced by a conventional procedure.
  • the shampoo thus obtained exhibited a high detergent performance, good foaming properties, low irritating properties, and high rinsing effects.
  • a liquid body soap having the formulation shown below was prepared by a conventional procedure.
  • the liquid body soap thus obtained exhibited a high detergent performance, good foaming properties, and low irritating properties.
  • the detergent composition in accordance with the present invention exhibits a high detergency, good foaming properties, and low irritating properties and is useful as a hair detergent, a body detergent, or the like.
  • the detergent composition can be easily formulated with a cationic conditioning agent.
  • a hair detergent i.e., a rinse-in shampoo
  • the fingers are allowed to pass smoothly, and after drying of the hair the hair can be done in a soft and natural way and combs are allowed to pass smoothly.

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Abstract

The detergent composition comprises (A) 5 to 50 parts by weight of a polyoxyethylene alkyl ether type nonionic surface active agent, (B) 1 to 10 parts by weight of a betaine type surface active agent, and (C) 1 to 10 parts by weight of one or more nonionic surface active agents, which is selected from an alkyldimethylamine oxide, an alkyl saccharide, a fatty acid monoglyceride, or an alkanolamide, in which the weight ratio of component (A)/[component (B) + component (C)] is of 1/1 to 10/1.

Description

SPECIFICATION DETERGENT COMPOSITIONS
Technical Field
This invention relates to a detergent composition, which exhibits a high detergency, good foaming properties, and low irritating properties. This invention particularly relates to a detergent composition, which can be stably formulated with a cationic conditioning agent, and which has markedly high rinsing effects and high conditioning effects when it is used for washing hair.
Background Art
Most conventional detergents, particularly hair detergents, contain anionic surface active agents as predominant components since such detergents exhibit a high detergency and good foaming properties. However, the anionic surface active agents has high irritating properties. Therefore, when the anionic surface active agents are formulated in hair detergents, the anionic surface active agents are often used in combination with low-irritating surface active agents. There has been a demand for a hair detergent having lower irritating properties.
Also, recently, various attempts have been made in order to obtain a detergent, which also has conditioning effects. As the substances having the conditioning effects, many cationic substances have heretofore been known. However, in cases where a cationic substance is formulated with a detergent, which contains an anionic surface active agent as the predominant component, a complex of the cationic substance and the anionic surface active agent is formed undesirably. Therefore, it is difficult to formulate the cationic substance with the detergent, which contains an anionic surface active agent as a predominant component, and the problems occur in that, for example, sufficient conditioning effects cannot be obtained.
Therefore, attempts have heretofore been made in order to obtain a detergent containing, as the predominant component, a nonionic surface active agent, which has lower irritating properties than an anionic surface active agent and can be easily formulated with a cationic conditioning agent. For example, as a detergent containing an alkyl saccharide as a nonionic surface active agent, a low-irritating detergent composition, which contains an alkyl saccharide-based nonionic surface active agent and a cationic polymer, has been proposed in, for example, Japanese Patent Publication 6-23085. Also, a detergent composition, which contains alkyl saccharide type nonionic surface active agent, a sucrose fatty acid ester, and an anionic surface active agent, or an amphoteric surface active agent, has been proposed in, for example, Japanese Patent Publication 6-23086.
However, the alkyl saccharide type nonionic surface active agent is comparatively expensive. Therefore, attempts have also been made in order to formulate a polyoxyethylene alkyl ether type nonionic surface active agent, which is comparatively cheap, with a detergent. However, in general, the polyoxyethylene alkyl ether type nonionic surface active agent has poor foaming properties and has been rarely used for hair detergents. Only a shampoo composition, which contains an amide-amine type amphoteric surface active agent or an alkylolamide type nonionic surface active agent as the predominant component and contains a polyoxyethylene type surface active agent as an auxiliary component, has been proposed in, for example, Japanese Patent Application 55-25436.
Disclosure of the Invention
It is therefore an object of the present invention to provide a detergent composition, which exhibits a high detergency, good foaming properties, and low irritating properties, and which can be stably formulated with a cationic conditioning agent.
In view of the above circumstances, the inventors eagerly carried out research and found that a detergent composition, which exhibits a high detergency, good foaming properties, and low irritating properties, can be obtained by employing a specific polyoxyethylene alkyl ether type nonionic surface active agent, a betaine type surface active agent, and a specific nonionic surface active agent in combination with one another in a specific ratio. The present invention is based on such findings.
Specifically, the present invention provides a detergent composition comprising:
(A) 5 to 50 % by weight of a polyoxyethylene alkyl ether type nonionic surface active agent represented by formula (1); R1O-(CH2CH2O)n-H (1) wherein R1 represents a straight-chain or branched alkyl or alkenyl group having 11 to 15 carbon atoms; and
n represents a number of 11 to 30;
(B) 1 to 10 % by weight of a betaine type surface active agent; and
(C) 1 to 10 % by weight of one or more nonionic surface active agents selected from the compound represented by formula (2), (3), (4) or (5):
Figure imgf000007_0001
wherein R2 represents a straight-chain or branched alkyl or alkenyl group having 8 to 18 carbon atoms;
R3-(OR4)g-Gt (3)
wherein R3 represents a straight-chain or branched alkyl or alkenyl group having 6 to 18 carbon atoms;
R4 represents an alkylene group having 2 to 4 carbon atoms;
G represents a residue derived from a reducing sugar having 5 or 6 carbon atoms;
s represents an integer of 0 to 10; and
t represents a number of 1 to 10;
Figure imgf000008_0001
wherein only one of R5, R6 and R7 represents an O=CR8 group (wherein R8 represents a straight-chain or branched alkyl or alkenyl group having 6 to 18 carbon atoms), and the two remainders independently represent a hydrogen atom;
Figure imgf000009_0001
wherein R9 represents a straight-chain or branched alkyl or alkenyl group having 8 to 16 carbon atoms; and
u and v independently represent an integer of 0 to
10, at least either one of u and v being 1 or more, in which
the weight ratio of component (A) to the total of the components (B) and (C), (A)/[(B) + (C)], falls within the range of 1/1 to 10/1.
The detergent composition in accordance with the present invention is suitable for a hair detergent and a body detergent, particularly for a hair detergent and a rinse-in shampoo containing a cationic conditioning agent.
Detailed Description of the Invention The polyoxyethylene alkyl ether type nonionic surface active agent serving as the component (A) for use in the detergent composition in accordance with the present invention is represented by formula (1). R1 in formula (1), which represents a straight-chain or branched alkyl or alkenyl group having 11 to 15 carbon atoms, includes undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, undecenyl, dodecenyl, tridecenyl, te tradecenyl, and pentadecenyl groups. In the component (A), the number of carbon atoms in R1 is 11 to 15, and n, representing the number of moles of ethylene oxide added, is 11 to 30. Preferred component (A) includes a polyoxyethlene alkyl ether type nonionic surface active agent represented by formula (1) wherein R1 is a straight-chain or branched alkyl or alkenyl group having 12 to 14 carbon atoms and n is 15 to 25 for obtaining higher foaming properties.
The polyoxyethylene alkyl ether type nonionic surface active agent serving as the component (A) is a predominant component of the detergent composition according to the present invention. The polyoxyethylene alkyl ether type nonionic surface active agent is formulated in a proportion falling within the range of 5 to 50% by weight (hereinbelow unless otherwise specified, all the percentages denote "% by weight"), preferably 10 to 50 % by weight, more preferably 10 to 30%, still preferably 10 to 20%, based on the total weight of the detergent composition. If the proportion of the component (A) is smaller than 5%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (A) is larger than 50%, the viscosity of the detergent composition will become high, and it will unfavorably become difficult to formulate other components.
The betaine type surface active agent serving as the component (B) for use in the detergent composition according to the present invention may be of the carbobetaine type, the sulfobetaine type, the imidazolinium betaine type, or the like. Preferred among them is a carbobetaine type amphoteric surface active agent represented by formula (8):
Figure imgf000011_0001
wherein R18 represents a straight-chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms, or R19CONH(CH2)z- (wherein R19 represents a straight- chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms, and z represents an integer of 1 to 5); M represents a hydrogen atom, an alkali metal, or triethanolamine; and y represents an integer of 1 to 5, or
a sulfobetaine type amphoteric surface active agent represented by formula (9):
Figure imgf000012_0001
wherein R20 represents a straight-chain or branched alkyl or alkenyl group having 8 to 20 carbon atoms; and M and y are as defined above.
More preferred among them is a carbobetaine type amphoteric surface active agent represented by formula (8), with a fatty acid amide propyl betaine of formula (8) (wherein R18 represents a group represented by R19CONH ( CH2 ) 3- ) being most preferred .
The betaine type surface active agent serving as the component (B) is formulated in a proportion falling within the range of 1 to 10%, preferably 1 to 5%, more preferably 1 to 3%, based on the total weight of the detergent composition. If the proportion of the component (B) is smaller than 1%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (B) is larger than 10%, the detergent composition unfavorably has increased irritating properties.
The nonionic surface active agent serving as the component (C) for use in the detergent composition of the present invention, is one or more compounds selected from an alkyldimethylamine oxide of formula (2), an alkyl saccharide of formula (3), a fatty acid monoglyceride of formula (4), or an alkanolamide of formula (5). These nonionic surface active agents will be described below.
In the alkyldimethylamine oxide of formula (2), R2 formula (2) preferably represents an alkyl group having 10 to 16 carbon atoms, more preferably a decyl, lauryl or myristyl group.
In the alkyl saccharide of formula (3), R3 preferably represents an alkyl group having 10 to 14 carbon atoms, more preferably a decyl, dodecyl, or tetradecyl group. R4 preferably represents an ethylene and propylene group. The chemical structure of G depends on the raw material to be used, such as a monosaccharide, a disaccharide and a higher saccharide, and glucose, galactose and fructose being preferred. s preferably represents an integer of 0 to 2, and t preferably represents a number of 1 to 2. The alkyl saccharide represented by formula (3) is still preferably an alkyl polyglycoside, wherein s=0, and G is a residue derived from glucose.
In the fatty acid monoglyceride of formula (4),
R8 preferably represents a straight-chain or branched alkyl or alkenyl group having 8 to 12 carbon atoms. In formula (4), ester bonding has only to be formed at either of the carbon atoms in the glycerin. In formula (4), the ester groups may be located at either of the carbon atoms in the glycerin.
In the alkanolaminde represented formula (5), R9 preferably represents a straight-chain or branched alkyl or alkenyl group having 10 to 14 carbon atoms, with straight-chain group having 11 to 13 carbon atoms being still preferred. u and v independently prefer ably represent an integer of 0 to 3.
Among these nonionic surface active agents, the alkyldimethylamine oxide of formula (2) and the fatty acid monoglyceride of formula (4) are preferred for obtaining enhanced foaming properties. In particular, the fatty acid monoglycer ides of formula (4) such as decanoic acid monoglyceride and lauric acid monoglyceride are still preferred.
The nonionic surface active agent serving as the component (C) may be used either individually or in combination of two or more of them, with the combination of two or more of them being still preferred for obtaining enhanced foaming properties. The nonionic surface active agent serving as the component (C) is formulated in a proportion falling within the range of 1 to 10%, preferably 1 to 5%, based on the total weight of the detergent composition. If the proportion of the component (C) is lower than 1%, a sufficient detergent performance and sufficient foaming properties cannot be obtained. If the proportion of the component (C) is larger than 10%, the detergent performance will often be impaired.
In the detergent composition of the present invention, the proportion of the component (A) should be determined so that the weight ratio of the amount of the component (A) to the total amount of the components (B) and (C), i.e. the weight ratio (A)/[ (B) + (C)], may fall within the range of 1/1 to 10/1. If the weight ratio ( A) /[ (B) + (C) ] falls outside this range, the detergent composition cannot exhibit a high detergency, good foaming properties, and low irritating properties simultaneously. It is preferred for obtaining enhanced forming properties that the weight ratio (A)/[ (B)+(C)] falls within the range of 3/2 to 3/1.
To the detergent composition of the present invention may be added a cationic conditioning agent to obtain sufficient conditioning effects. Examples of the cationic conditioning agents include cationic surface active agents and cationic polymers, with cationic surface active agents of formulae (6) and (7) being preferred for obtaining enhanced conditioning effects.
Figure imgf000016_0001
wherein R10 represents a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms; R11 represents a hydrogen atom, a methyl group, an ethyl group, or a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms; R12 and R13 independently represent a hydrogen atom, a methyl group, or an ethyl group; and X- represents a halogen atom or an organic anionic group.
Figure imgf000017_0001
wherein R14 represents a straight-chain or branched alkyl or alkenyl group having 7 to 35 carbon atoms; R15 , R16 and R17 independently represent an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms, or a hydrogen atom; L represents -CONJ- (wherein J represents a hydrogen atom or an alkyl or hydroxyalkyl group having 1 to 3 Carbon atoms), -O-, or -COO-; Y represents a hydrogen atom, a hydroxyl group, a straight-chain or branched alkyl, alkenyl, or hydroxyalkyl group having 1 to 36 carbon atoms, or a group represented by the formula:
Figure imgf000018_0001
wherein Z represents a hydrogen atom or a hydroxyl group; w represents a number of 2 or 3; x represents an integer of 0 to 5; and X- is as defined above, with the proviso that, in cases where x=1, Z represents a hydrogen atom or a hydroxyl group, and in cases where x=0, 2, 3, 4 or 5, Z represents a hydrogen atom.
In the cationic surface active agent represented by formula (6), it is preferred that R10 represents a straight-chain alkyl group having 14 to 22 carbon atoms, R11 represents a methyl group or an ethyl group, R12 and R13 independently represent a methyl group or an ethyl group, and X represents Cl-, Br-, CH3OSO3- or C2H5OSP3-.
In the cationic surface active agent represented by formula (7), for enhancing foaming properties during washing, R14 preferably represents a straight-chain or branched alkyl or alkenyl group having 7 to 21 carbon atoms, in particular 11 to 17 carbon atoms; and R15, R16 and R17 independently preferably represent a methyl or ethyl group; M preferably represents -CONH-; Y preferably represents a hydrogen atom or a hydroxyl group; and Z preferably represents a hydrogen atom or a hydroxyl group.
It is preferred that the proportion of the cationic conditioning agent falls within the range of 0.1 to 10 %, preferably 1 to 10%, based on the total weight of the detergent composition. It is still preferred for obtaining higher conditioning effects that the proportion falls within the range of 3 to 8%, based on the total weight of the detergent composition.
To the detergent composition of the present invention may be added anionic surface active agents, which are conventionally used in detergents in such a proportion that the advantageous effects of the present invention are not impaired. Examples of anionic surface active agents include an alkyl sulfate, an alkyl ether sulfate, an alkyl sulfonate, a sulfosuc- cinate, an α-sulfo fatty acid ester, an α-olefin sulfonate, a saturated or unsaturated fatty acid ester, a phosphoric acid monoester type surface active agent, and an acylated amino acid.
Also, in the detergent composition in accordance with the present invention, silicone derivatives may be contained in such a proportion that the advantageous effects of the detergent composition in accordance with the present invention may not be impaired. In such cases, a good slip feeling and a dry feeling can be obtained. No limitation is imposed on the kind of the silicone derivative so far as it is conventionally formulated in detergents and cosmetic preparations. Examples of the silicone derivatives include a dimethylpolysiloxane, a methylphenylpolysiloxane, a polyether-modif ied silicone, an epoxy-modif ied silicone, an alkoxy-modified silicone, and an amino-modified silicone.
Further, in the detergent composition in accordance with the present invention, if desired, other components than the above-enumerated components, which are ordinarily formulated in cosmetic preparations, pharmaceutical preparations, foods, or the like may be added in such a proportion that the advantageous effects of the detergent composition in accordance with the present invention may not be impaired. Examples of such components include an anti-dandruff agent, a bactericide, an anti-inflammation agent, a medicinal agent, an antiseptic, a humectant, such as propylene glycol, glycerol, diethylene glycol monoethyl ether, sorbitol and panthenol, a coloring agent, such as a dye and a pigment; a conditioning agent, such as perfluoro polyether; a pearling agent, a chitosan derivative, such as hydroxypropyl chitosan, a formulated perfume, and components described in "Encyclopedia of Shampoo Ingredients," Micelle Press, 1985 which is incorporated herein by reference.
The detergent composition in accordance with the present invention can be produced by a conventional manner and may take on the form of paste, gel or liquid.
Examples
The present invention will hereinbelow be illustrated in further detail by the following nonlimi- tative examples.
Examples 1 to 6 and Comparative Examples 1 to 14
Shampoos having the formulation shown in Tables 1 to 3 below were prepared by a conventional procedure. The detergency, the foaming properties, and the irri tating properties of the shampoos were evaluated. The results obtained are shown in Tables 1 to 3.
(Method of Evaluation)
Detergency: One gram of a test shampoo liquid was applied to 20 g (length: 15 cm) of hairs of a healthy Japanese female, followed by washing for 1 minute and rinsing. The feeling of the hair after rinsing was evaluated by 20 specialized panel members and evaluated according to the following scale.
Excellent: 90% of the panel members evaluated the detergency as good.
Good: From 80% to less than 90% of the panel members evaluated the detergency as good. Fair: From 70% to less than 80% of the panel members evaluated the detergency as good. Poor: Less than 70% of the panel members evaluated the detergency as good.
Foaming properties: Into a cylinder was introduced 800 ml of aqueous solution of the shampoo diluted in twenty times amount of water (solution temperature 20 ºC)C followed by rotation of a stirring blade equipped within the aqueous solution for 5 minutes. Thereafter, the aqueous solution was allowed to stand for 30 seconds, and the degree of foaming was evaluated according to the following scale. The rotation rate of the stirring blade was 1,000 rpm, and the rotation was reversed every five seconds.
Excellent: Markedly abundant foaming was observed.
Good: Abundant foaming was observed.
Fair: Foaming was observed, but insufficient.
Poor: Almost no foaming was observed.
Skin irritation: A conduct of immersing the hands in each shampoo liquid for five minutes and thereafter drying the hands was repeated 10 times by 20 specialized panel members. The degree of irritation to the skin was evaluated according to the following scale. Excellent: 90% or more of the panel members felt that skin irritation was low.
Good: From 80% to less than 90% of the panel
members felt that skin irritation was low. Fair: From 70% to less than 80% of the panel
member felt that the skin irritation was low.
Poor: Less than 70% of the panel members felt that skin irritation was low.
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Examples 7 to 11 and Comparative Examples 15 to 24
Shampoos having the formulation shown in Tables 4 to 6 were prepared by a conventional procedure. Detergency, foaming properties, skin irritation were evaluated as in Example 1. Also, the softness of the hair after drying and the stability of the detergent were evaluated. Softness of the hair after drying and the stability of the detergent were also evaluated by the method described below. The results obtained are shown in Tables 4 to 6.
(Method of Evaluation)
Softness of hair after drying: One gram of the shampoo liquid was applied to 20 g of hair (length: 15 cm) of a healthy Japanese female. The shampoo liquid was caused to foam for one minute. The hair was then rinsed with water, dried with a towel, and dried with a dryer. These operations were carried out by 20 specialized panel members, and the softness of the hair after drying was evaluated according to the following scale. Excellent: Very soft and flexible
Good: Soft
Fair: Slightly insufficient to softness
Poor: Stiffy
Stability of detergent: After preparation of the shampoo, the shampoo was shaken violently, followed by allowing to stand at 20 ºC for one week, and then the state of the liquid was observed with naked eyes and evaluated according to the scale.
Good: Uniformly liquefied.
Fair: Almost uniformly liquefied with a little
precipitates observed.
Poor: A large quantities precipitates were observed.
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Example 12 (Shampoo)
A shampoo having the f ormula t i on shown below was produced by a conventional procedure.
The shampoo thus obtained exhibited good detergency, good foaming properties, and low skin irritation.
Figure imgf000032_0001
1): In formula (3), R3 = C10H21, s = 0, G = the glucose residue, and t = 1.2.
2): JR400 (produced by Union Carbide Co., Ltd.) 3): HEC-SE850 (produced by Shin-Etsu Chemical Co.,
Ltd.)
4): SM-8702C (supplied by Dow Corning Toray Silicone Co., Ltd.)
Example 13 (Rinse-in shampoo)
A rinse-in shampoo having the formulation shown below was produced by a conventional procedure.
The shampoo thus obtained exhibited a high detergent performance, good foaming properties, low irritating properties, and high rinsing effects.
Figure imgf000033_0001
Note: 5): BY22-029 (supplied by Dow Corning Toray Silicone Co., Ltd.)
Example 14 (Body Liquid Soap)
A liquid body soap having the formulation shown below was prepared by a conventional procedure.
The liquid body soap thus obtained exhibited a high detergent performance, good foaming properties, and low irritating properties.
Figure imgf000034_0001
Note: 6): In formula (3), R represents C10H21' s represents 0, G represents the glucose residue, and t represents 1.2. Industrial Applicability
The detergent composition in accordance with the present invention exhibits a high detergency, good foaming properties, and low irritating properties and is useful as a hair detergent, a body detergent, or the like. The detergent composition can be easily formulated with a cationic conditioning agent. In particular, in cases where the detergent composition is used as a hair detergent (i.e., a rinse-in shampoo), during washing and rinsing of the hair the fingers are allowed to pass smoothly, and after drying of the hair the hair can be done in a soft and natural way and combs are allowed to pass smoothly.
Many other variations and modifications of the invention will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The above-described embodiments are, therefore, intended to be merely exemplary, and all such variations and modifications are intended to be included within the scope of the invention as defined in the appended claims.

Claims

1. A detergent composition comprising:
(A) 5 to 50 parts by weight of a polyoxyethylene alkyl ether type nonionic surface active agent represented by formula (1);
R1O-(CH2CH2O)n-H (1) wherein R1 represents a straight-chain or branched alkyl or alkenyl group having 11 to 15 carbon atoms; and
n represents a number of 11 to 30;
(B) 1 to 10 parts by weight of a betaine type surface active agent; and
(C) 1 to 10 parts by weight of one or more nonionic surface active agents selected from the compound represented by formula (2), (3), (4) or (5):
Figure imgf000036_0001
wherein R2 represents a straight-chain or branched alkyl or alkenyl group having 8 to 18 carbon atoms; R3-(OR4)s-Gt (3)
wherein R3 represents a straight-chain or branched alkyl or alkenyl group having 6 to 18 carbon atoms;
R4 represents an alkylene group having 2 to 4 carbon atoms;
G represents a residue derived from a reducing sugar having 5 or 6 carbon atoms;
s represents an integer of 0 to 10; and
t represents a number of 1 to 10;
Figure imgf000037_0001
wherein only one of R5, R6 and R7 represents an O=CR8 group (wherein R8 represents a straight-chain or branched alkyl or alkenyl group having 6 to 18 carbon atoms), and the two remainders independently represent a hydrogen atom;
Figure imgf000038_0001
where in R9 represents a s tra i ght-chain or branched alkyl or alkenyl group having 8 to 16 carbon atoms ; and
u and v independently represent an integer of 0 to
10, at least either one of u and v being 1 or more, in which
the weight ratio of component (A) to the total of the components (B) and (C), (A)/[(B) + (C)], falls within the range of 1/1 to 10/1.
2. The detergent composition according to claim 1, wherein, in formula (1), R1 represents a straight-chain or branched alkyl or alkenyl group having 12 to 14 carbon atoms, and n represents a number of 15 to 25.
3. The detergent composition according to claim 1, wherein the component (B) is a carbobetaine type amphoteric surface active agent.
4. The detergent composition according to claim 1, wherein the component (C) is a nonionic surface active agent represented by formula (2) or (4).
5. The detergent composition according to claim 1, wherein the weight ratio (A)/[ (B) +(C)] falls within the range of 3/2 to 3/1.
6. The detergent composition according to claim 1, further comprising a cationic conditioning agent.
7. The detergent composition according to claim 6, wherein the proportion of the cationic conditioning agent falls within the range of 0.1 to 10% by weight.
8. The detergent composition according to claim 6 or 7, wherein the cationic conditioning agent is a cationic surface active agent represented by formula (6) or (7):
Figure imgf000040_0001
wherein R10 represents a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms; R11 represents a hydrogen atom, a methyl group, an ethyl group, or a straight-chain or branched alkyl or alkenyl group having 8 to 22 carbon atoms;
R12 and R13 independently represent a hydrogen atom, a methyl group, or an ethyl group; and
X represents a halogen atom or an organic anionic group; w
Figure imgf000040_0002
wherein R14 represents a straight-chain or branched alkyl or alkenyl group having 7 to 35 carbon atoms; R15 , R16 and R17 independently represent an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms, or a hydrogen atom;
L represents -CONJ- (wherein J represents a hydrogen atom or an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms), -O-, or -COO-; and
Y represents a hydrogen atom, a hydroxyl group, a straight-chain or branched alkyl, alkenyl or hydroxyalkyl group having 1 to 36 carbon atoms, or
Figure imgf000041_0001
wherein Z represents a hydrogen atom or a hydroxyl group;
w represents a number of 2 or 3;
Z represents an integer of 0 to 5, with the proviso that, in cases where x=1, Z represents a hydrogen atom or a hydroxyl group, and in cases where x = 0, 2, 3, 4 or 5, Z represents a hydrogen atom.
9. The detergent composition according to claiam 8, wherein the cationic conditioning agent is a cationic surface active agent represented by formula (7).
PCT/JP1995/001658 1994-08-24 1995-08-22 Detergent compositions WO1996005807A1 (en)

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