EP0322741A2 - Composition détergente peu irritante - Google Patents

Composition détergente peu irritante Download PDF

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Publication number
EP0322741A2
EP0322741A2 EP88121427A EP88121427A EP0322741A2 EP 0322741 A2 EP0322741 A2 EP 0322741A2 EP 88121427 A EP88121427 A EP 88121427A EP 88121427 A EP88121427 A EP 88121427A EP 0322741 A2 EP0322741 A2 EP 0322741A2
Authority
EP
European Patent Office
Prior art keywords
coom
surfactant
hydrogen atom
group
represented
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.)
Granted
Application number
EP88121427A
Other languages
German (de)
English (en)
Other versions
EP0322741A3 (en
EP0322741B1 (fr
Inventor
Angel Rosell Noguera
Carlos Cornet Planells
Masaki Itahashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP0322741A2 publication Critical patent/EP0322741A2/fr
Publication of EP0322741A3 publication Critical patent/EP0322741A3/en
Application granted granted Critical
Publication of EP0322741B1 publication Critical patent/EP0322741B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group

Definitions

  • This invention relates to a low irritant detergent composition, and more specifically to a detergent composition having low irritation to the skin and eyes as well as good washing and cleaning power and foaming power.
  • Detergents are of course required to have excellent detergency such as washing and cleaning power and foaming power and for those brought into direct contact with the skin and the like such as detergents for people (shampoos, body shampoos, etc.), kitchen detergents, mild detergents for wool, are also required in particular to have low irritation to the skin and eyes and also to have good stability as solutions.
  • anionic surfactants such as linear alkyl benzene sulfonates (LAS), alkyl sulfate esters (AS), polyoxyethylene alkyl ether sulfate ester salts (AES) and a-olefinsulfonates (AOS) are used.
  • LAS linear alkyl benzene sulfonates
  • AS alkyl sulfate esters
  • AES polyoxyethylene alkyl ether sulfate ester salts
  • AOS a-olefinsulfonates
  • Japanese Patent Laid-Open No. 127396/1987 discloses to incorporate a surfactant of the sulfosuccinic acid type as a third essential component.
  • the surfactant of the sulfosuccinic acid type itself is however a relatively low irritant anionic surfactant and as disclosed in Japanese Patent Laid-Open No. 38395/1981 by way of example, is effective in reducing the irritant property of AES when combined with AES.
  • Such a surfactant of the sulfosuccinic acid type is however generally insufficient in foaming power and low-temperature stability, so that it is the current status that the surfactant is used only as an auxiliary active agent for AES.
  • the detergent of Japanese Patent Laid-Open No. 86892/1980 which contains both a surfactant of the sulfosuccinic acid type and a surfactant of the imidazoline type may be mentioned as a relatively close example. It however involves a problem in foaming property.
  • a detergent composition capable of reducing irritation and moreover having satisfactory stability as a solution without impairing its foaming power and washing and cleaning power can be obtained by combining (A) an a-olefinsulfonic acid salt and (B) a particular surfactant of the sulfosuccinic acid ester type with (C) an amphoteric imidazoline surfactant and (D) a nonionic alkanolamide surfactant, leading to completion of the present invention.
  • the present invention therefore provides a low irritant detergent composition
  • a low irritant detergent composition comprising (A) an ⁇ -olefinsulfonic acid salt, (B) a surfactant of the sulfosuccinic acid ester type, represented by the following formula [I]: wherein R means R 1 O( ⁇ CH 2 CH 2 O) ⁇ m , R, being a linear or branched alkyl or alkenyl group having 8-22 carbon atoms and m standing for a number of 1-20 on average, and M denotes a hydrogen atom or a cationic ion capable of forming a water-soluble salt selected from the group consisting of alkali metal ions, ammonium ion and organoammonium ions, (C) an amphoteric imidazoline surfactant and (D) a nonionic alkanolamide surfactant, the weight ratio of (A)/(B) being 1/3-3/1, that of (C) / (A) being 1/10
  • a-olefinsulfonic acid salt (A) used in this invention may be mentioned by way of example a sulfonated a-olefin derivative represented by the following formula [V]: R 10 -SO 3 M" [V] wherein R io means a linear or branched alkenyl or hydroxyl-substituted alkyl group having 8-22 carbon atoms on average and M denotes a hydrogen atom or a cation capable of forming a water-soluble salt selected from the group consisting of alkali metal salts.
  • the preferable average carbon number of R 10 may range especially from 14 to 16 from the standpoint of the foaming property and stability of the composition.
  • the surfactant of the sulfosuccinic acid ester type (B) in this invention it is possible to use a higher alcohol ethoxylate or that derived from a higher fatty acid amide and containing an ethoxy group, which is represented by the formula [I].
  • the number m of polymerized ethoxy groups in the formula [I] may preferably be 2-10 since a greater m value gives less irritation but leads to reduced fundamental properties as a detergent.
  • R,OH not only a primary alcohol but also a secondary alcohol can be used suitably.
  • amphoteric imidazoline surfactant (C) in this invention include the following compounds (amphoteric surfactants of the amideamine type) (1 )-(3).
  • R 2 CO- group in the formula [II] or the RsCHCO- group in the formula [IV] a group derived from lauric acid, oleic acid, coconut oil fatty acid or palm kernel oil fatty acid is preferred.
  • a sodium ion, hydrogen atom or triethanolamine salt ion is most preferred as M .
  • nonionic alkanolamide surfactant (D) in this invention may be mentioned for example a compound represented by the following formula [VI]: wherein R 1 means a linear or branched alkyl or alkenyl group having 7-21 carbon atoms on average and R 12 and R 13 denote individually a hydrogen atom, 2-hydroxyethyl group or 2-hydroxypropyl group.
  • (A) and (B) are used to give an (A)/(B) weight ratio of 1/3-3/1. If (A)/(B) exceeds 3/1, it is impossible to provide a composition having sufficiently low irritation. It is necessary to incorporate a great deal of the component (C) in order to render this composition low irritant, whereby problems arise with respect to detergency and foaming property. Such an unduly large (A)/(B) ratio is therefore not preferred. It (A) / (B) becomes smaller than 1/3, it is impossible to obtain a composition having sufficient stability at low temperatures. Such an unduly small (A)/(B) ratio is hence not preferred either.
  • (C) and (A) are used to give a weight ratio of 1/10-1/1. If the (C)/(A) ratio is smaller than 1/10, it is impossible to obtain a low irritant composition although sufficient washing and cleaning power and foaming power are obtained. On the other hand, any (C)/(A) ratios greater than 1/1 are not preferred because problems arise with respect to the foaming power and stability.
  • (D), (A) and (B) are used to give a (D)/(A) + (B) weight ratio of 1/20-1/2. If the ratio exceeds 1/2, the removal of foams is impaired. If the ratio becomes smaller than 1 / 20 on the other hand, the resulting detergent has poor foaming power and the quality of foams is lowered. Any (D)/(A)+(B) weight ratios outside the above range are hence not preferred.
  • composition of this invention (A), (B), (C) and (D) are used in such amounts that their total weight accounts for 10-40 wt.% of the whole composition. Any total weights smaller than 10 wt.% cannot achieve sufficient foaming power, while any total weights greater than 40 wt.% cannot provide a uniform and stable composition. Total weights outside the above range are hence not preferred.
  • the detergent composition of this invention may additional contain one or more conventional surfactants in a total proportion of 0-10 wt.%.
  • a solubilizing adjuvant such as glycerin, propylene glycol, ethanol or urea, a thickener such as a water-soluble high molecular substance, polyethylene glycol fatty acid ester or sodium chloride, an antiseptic such as paraben, and/or an antioxidant such as BHT for shaping and/or stabilizing purposes.
  • a color, a perfume base, an antidandruff agent, an antiphlogistic, vitamines, a plant extract, and/or a protein or its derivative or decomposition product in a total proportion of 0-5 wt.%.
  • the remainder consists of water, whose proportion ranges from 30 wt.% to 90 wt.%.
  • the detergent composition of this invention can be formed into various preparation forms such as liquid (lotion-like) form, paste-like form and gel-like form as desired. Its pH may be adjusted to 4-10, more preferably, to 5.5-7.5 with an acid or base as needed.
  • compositions of this invention are beneficial, for example, as hair and skin detergents for infants, as kitchen detergents for housewives whose hands are sensitive and susceptible to roughening, as daily shampoos for those washing their hair everyday, and as low-irritant hair-dressing shampoos for those unavoidably exposed as a profession to shampoo for long time.
  • Oily artificial dirt and filth were dispersed evenly in a solvent.
  • a wool muslin blanket was brought into contact with the dispersion, followed by drying to have the oily artificial dirt and filth adhered on the blanket.
  • the blanket was cut into test pieces of 10 cm x 10 cm wide for use in testing.
  • a detergent composition was dissolved in hard water of German hardness 15° d to prepare 1 l of a 3% aqueous solution of the detergent composition.
  • Five deliberately-soiled fabric sheets and the aqueous solution were placed, as they were, in a stainless steel beaker equipped with a targotometer, and were then whirled at 75 rpm, 40 C for 3 minutes by the targotometer. After rinsing the fabric sheets under running water, they were ironed for measurement of their reflectance.
  • each detergent composition was evaluated by comparing it to the washing and cleaning power of a standard detergent of the following formulation:
  • the maximum irritation index is 44.
  • Each detergent composition was stored separately at 5°C, room temperature, 40° C and 50 C for 1 month and its external appearance, pH, viscosity and fragrance were evaluated every week.
  • Liquid detergent compositions of compositions shown in Table 1 were prepared, and their foaming power, washing and cleaning power, stability and eye coat irritation were evaluated. Incidentally, each composition was adjusted to pH 7.0 with a small amount of citric acid.
  • Liquid detergent compositions of formulations shown in Table 2 were separately prepared, and their foaming power, stability, eye coat irritation and dioxane concentrations were evaluated.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
EP88121427A 1987-12-28 1988-12-21 Composition détergente peu irritante Expired - Lifetime EP0322741B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP62332793A JPH0759715B2 (ja) 1987-12-28 1987-12-28 低刺激性洗浄剤組成物
JP332793/87 1987-12-28

Publications (3)

Publication Number Publication Date
EP0322741A2 true EP0322741A2 (fr) 1989-07-05
EP0322741A3 EP0322741A3 (en) 1990-05-02
EP0322741B1 EP0322741B1 (fr) 1994-10-12

Family

ID=18258869

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88121427A Expired - Lifetime EP0322741B1 (fr) 1987-12-28 1988-12-21 Composition détergente peu irritante

Country Status (5)

Country Link
EP (1) EP0322741B1 (fr)
JP (1) JPH0759715B2 (fr)
AT (1) ATE112798T1 (fr)
DE (1) DE3851829T2 (fr)
ES (1) ES2064340T3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112358583A (zh) * 2020-12-07 2021-02-12 广东灵捷制造化工有限公司 一种降低aes刺激性的高分子表面活性剂及其制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0721154B2 (ja) * 1988-10-15 1995-03-08 三洋化成工業株式会社 洗浄剤組成物
JP4717250B2 (ja) * 2001-04-16 2011-07-06 日本メナード化粧品株式会社 洗髪用化粧料

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5368721A (en) * 1976-12-01 1978-06-19 Lion Corp Disubstd. aliphatic carboxylic acid amide amines, and detergents and cosmeticcompositions containing the same
US4181634A (en) * 1977-06-17 1980-01-01 Johnson & Johnson Mild cleansing compositions comprising an alkyleneoxylated bisquaternary ammonium compound and an anionic or amphoteric detergent such as a phosphobetaine
JPS5586893A (en) * 1978-12-22 1980-07-01 Sunstar Hamigaki Detergent composition
DE3125102A1 (de) * 1981-06-26 1983-01-20 Hoechst Ag, 6000 Frankfurt "tensidmischungen aus (alpha)-olefinsulfonanten und anderen tensiden"
JPS60132912A (ja) * 1983-12-21 1985-07-16 Kao Corp シヤンプ−組成物
US4876034A (en) * 1986-11-18 1989-10-24 Kao Corporation Secondary amidoamino acid based detergent composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112358583A (zh) * 2020-12-07 2021-02-12 广东灵捷制造化工有限公司 一种降低aes刺激性的高分子表面活性剂及其制备方法

Also Published As

Publication number Publication date
JPH01175927A (ja) 1989-07-12
JPH0759715B2 (ja) 1995-06-28
EP0322741A3 (en) 1990-05-02
DE3851829D1 (de) 1994-11-17
DE3851829T2 (de) 1995-05-11
EP0322741B1 (fr) 1994-10-12
ES2064340T3 (es) 1995-02-01
ATE112798T1 (de) 1994-10-15

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