CA1088427A - Imidazoline-containing hair shampoo compositions - Google Patents
Imidazoline-containing hair shampoo compositionsInfo
- Publication number
- CA1088427A CA1088427A CA266,311A CA266311A CA1088427A CA 1088427 A CA1088427 A CA 1088427A CA 266311 A CA266311 A CA 266311A CA 1088427 A CA1088427 A CA 1088427A
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- CA
- Canada
- Prior art keywords
- carbon atoms
- surfactant
- equals
- molecular weight
- condensing
- 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.)
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
-
- 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
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
-
- 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
-
- 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
-
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
Abstract
ABSTRACT
Aqueous hair shampoo compositions having low eye irritation potential along with excellent foaming and cleansing characteristics consisting of mixtures of 2-alkyl-substituted imdazoline ampholytic surfactants, polyoxyethylene-polyoxypropylene block copolymer nonionic surfactants and alcohol ether sulfate anionic surfactants.
Aqueous hair shampoo compositions having low eye irritation potential along with excellent foaming and cleansing characteristics consisting of mixtures of 2-alkyl-substituted imdazoline ampholytic surfactants, polyoxyethylene-polyoxypropylene block copolymer nonionic surfactants and alcohol ether sulfate anionic surfactants.
Description
~0~15142'7 : `
Field of the Invention .
m is invention relates to aqueous shampoo ccmpositions comprising mixtures of specified anionic, nonionic and c~mpholytic surfactants and having desirably high levels of cleansing and foaming while at the sclme time exhibiting low levels of eye irritation.
- Background of the Invention It has long been the goal of those engaged in the development and formulation of shampoo products for use on human hair to achieve the best possible balance of the criteria perceived c~d use~ by the cons~mer as measures of product satisfaction.
One of these criteria is the ability of a shampoo to cleanse the hair and scalp to the proper degree, neither lea~iny the hair fibers coated with a perceivable residue of sebum as a result o insuE~icient detergency, nor leavincJ th~m ccmpletely scour~l an~l strawlike as a result of ~oo complete a removal of the natural oil8 Another o the criteria which consumers use as a measure of satisfaction in the evaluation of a shampoo product is its foamincJ
charaateristics. It is desirable that a relatively small quantity of shampoo, when worked into the wet hair, rapidly generate a large volume of dense, creamy and lubrous foam, stable through the shampooing procedure.
~esthetic considerations also are important in the formulation o shampoo products. Not only should a ormulation retain its compositional integrity to obviate any need for shaking before use, but it is also desirable to be able to offer the consumer a product which is water clear and which may be attractively colored for packaging in transparent containers.
Another very important requirement in the develoFment of products such as hair shampoos htended for use near the eyes is that the potential for stinging or irritation as a result of accidental installation during use be minimized. ;~
--1-- ...
~ 384~7 .
While the various types of surfactants which have been employed in the formulation of shampoos exhibit satisfactory ;
properties in one or more of the above areas, no single type has provided a completely satisfactory combination of all properties. It is for this reason that a good deal of effort continues to be devoted to the search for mixtures of surface active agents which will possess all of the attributes desirable ~ -- in an ideal shampoo.
One class of surfactant of particular interest in the formulation of shampoo compositions having reduced eye irritation potential is the ampholytes, from 2-alkyl-substituted lmidazolines. Much effort has gone into the development of mixtures of these imidazoline derivatives with a variety of other surfactants to improve their detergency, foaming properties and ease of Eormulation without affecting their inherent mildness.
See, for example, U.S. Patents 3,1~6,656; 3,341,460; and ~; ;
3,723,360.
Summary of the Invention ;~
In one particular aspect the present invention provides an aqueous shampoo composition exhibiting reduced levels of -~
eye irritation which comprises water in combination with n ampholytic surfactant comprising a 2-alkyl-substituted imidazoline, a nonionic surfactant comprising a polyoxyethylene- ;
polyoxypropylene block copolymer and an anionic surfactant comprising an alcohol ether sulfate, the quantity of said ampholytic surfactant being 6.0 to 15.0% by weight, the ratio of said nonionic surfactant to said anionic surfactant being 0.5:1 to 10:1 and the proportion of the total of said nonionic surfactant and anionic surfactant to said ampholytic surfactant being l:l to 5:1.
Detailed Description of the Invention 1!~'' .'.. "'".
We have discovered that shampoos having a very :low eye jl/ -2-.. :. .
1~18~4~ ~
.
irritation potential along with excellent foaming and cleansing characteristics can be prepared by combining in specified proportions 1) an ampholytic surfactant comprising a 2-alkyl-substituted imidazoline, 2) a nonionic surfactant comprising a polyoxyethylene-polyoxypropylene block copolymer, and 3) an anionic surfactant comprising an alcohol ether sulfate.
. ..: : .
The imidazoline compounds which we have found useful in achieving the above objectives include those having the ~;
following structures~
. ::
/ CH2 ... ~ :
Il I `.' :,' :', R -C N - Rl - OM ~ -R4 R2 - COOM .
C~l .
\
N C1l2 Il I :'' R - C - N - R~ -- O R3 - COOM
:. ,: .' and CH2 . ' R - C N - R~ - OM
. R4 R2 SO3M
ln whlch R ls a hydroearbon group having from 4 to 18 carbon atoms.
.: . - .
Rl, R2 and R3 are selected from the group consisting of a) aliphatic hydrocarbon groups of 1 to 4 carbon atoms, b) hydroxy-substituted aliphatic hydrocarbon groups of 1 to 4 carbon atoms, e) aliphatic hydrocarbon groups having a single ether i 30 linkage and of 2 to 4 carbon atoms, ~1/ -2a-: . .
- ~
-- ~)884Z7 :;
d) hydroxy-substituted aliphatic hydrocarbon groups .-~:
having single ether linkage and of 2 to 4 carbon .,~
atoms, .
e) aliphatic keto groups containing only a single keto : :
linkage and otherwise being hydrocarbon of 2 to 4 ;
carbon atoms, :~ :
f) aliphatic keto groups containing only a single keto linkage and otherwise being hydroxy-substituted hydrocarbon of 2 to 4 carbon atoms . -R4 is selected from the group consisting of a) a hydroxyl group and ;
b) the group -OS03 (CH2CH2O)nR5 in which R~ is a hydrocarbon group containing 8 to 18 carbon :~.
at.oms and n is a whole number from 0 to 4 incluslve, and M is an alkal:L metal. .:.
. ;,, -j : ' : I .
: :
':
.. . .
1~B84Z7 Imidazoline derivatives of this type are well .
known and methods for their preparation are described in :
various U. S. patents issued to Hans S. Mannheimer and are sold by the Miranol Chemical Company under the registered . ~
trademark MIRANOL. :~:
The nonionic surfactants which we use Ln our invention to provide enhanced cleansing abilities without the impartation of eye irritation problems are water soluble block copolymers of polyethylene and polypropylene selected from the group consisting of: ..
(a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight .
o 1,000 - 15,000, ~b) condensation producks of propylene oxide with bases ~ormed by condensing ekhylene oxide with ethylene glycol and having a molecular weight o 1,000 - 10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ,~
ethylenediamine and having a molecular weight of 1,000 - 30,000.
Suractants o this type are described in U.S.
: Patents No. 2,674,619; No. 3,036,118; and No.
Field of the Invention .
m is invention relates to aqueous shampoo ccmpositions comprising mixtures of specified anionic, nonionic and c~mpholytic surfactants and having desirably high levels of cleansing and foaming while at the sclme time exhibiting low levels of eye irritation.
- Background of the Invention It has long been the goal of those engaged in the development and formulation of shampoo products for use on human hair to achieve the best possible balance of the criteria perceived c~d use~ by the cons~mer as measures of product satisfaction.
One of these criteria is the ability of a shampoo to cleanse the hair and scalp to the proper degree, neither lea~iny the hair fibers coated with a perceivable residue of sebum as a result o insuE~icient detergency, nor leavincJ th~m ccmpletely scour~l an~l strawlike as a result of ~oo complete a removal of the natural oil8 Another o the criteria which consumers use as a measure of satisfaction in the evaluation of a shampoo product is its foamincJ
charaateristics. It is desirable that a relatively small quantity of shampoo, when worked into the wet hair, rapidly generate a large volume of dense, creamy and lubrous foam, stable through the shampooing procedure.
~esthetic considerations also are important in the formulation o shampoo products. Not only should a ormulation retain its compositional integrity to obviate any need for shaking before use, but it is also desirable to be able to offer the consumer a product which is water clear and which may be attractively colored for packaging in transparent containers.
Another very important requirement in the develoFment of products such as hair shampoos htended for use near the eyes is that the potential for stinging or irritation as a result of accidental installation during use be minimized. ;~
--1-- ...
~ 384~7 .
While the various types of surfactants which have been employed in the formulation of shampoos exhibit satisfactory ;
properties in one or more of the above areas, no single type has provided a completely satisfactory combination of all properties. It is for this reason that a good deal of effort continues to be devoted to the search for mixtures of surface active agents which will possess all of the attributes desirable ~ -- in an ideal shampoo.
One class of surfactant of particular interest in the formulation of shampoo compositions having reduced eye irritation potential is the ampholytes, from 2-alkyl-substituted lmidazolines. Much effort has gone into the development of mixtures of these imidazoline derivatives with a variety of other surfactants to improve their detergency, foaming properties and ease of Eormulation without affecting their inherent mildness.
See, for example, U.S. Patents 3,1~6,656; 3,341,460; and ~; ;
3,723,360.
Summary of the Invention ;~
In one particular aspect the present invention provides an aqueous shampoo composition exhibiting reduced levels of -~
eye irritation which comprises water in combination with n ampholytic surfactant comprising a 2-alkyl-substituted imidazoline, a nonionic surfactant comprising a polyoxyethylene- ;
polyoxypropylene block copolymer and an anionic surfactant comprising an alcohol ether sulfate, the quantity of said ampholytic surfactant being 6.0 to 15.0% by weight, the ratio of said nonionic surfactant to said anionic surfactant being 0.5:1 to 10:1 and the proportion of the total of said nonionic surfactant and anionic surfactant to said ampholytic surfactant being l:l to 5:1.
Detailed Description of the Invention 1!~'' .'.. "'".
We have discovered that shampoos having a very :low eye jl/ -2-.. :. .
1~18~4~ ~
.
irritation potential along with excellent foaming and cleansing characteristics can be prepared by combining in specified proportions 1) an ampholytic surfactant comprising a 2-alkyl-substituted imidazoline, 2) a nonionic surfactant comprising a polyoxyethylene-polyoxypropylene block copolymer, and 3) an anionic surfactant comprising an alcohol ether sulfate.
. ..: : .
The imidazoline compounds which we have found useful in achieving the above objectives include those having the ~;
following structures~
. ::
/ CH2 ... ~ :
Il I `.' :,' :', R -C N - Rl - OM ~ -R4 R2 - COOM .
C~l .
\
N C1l2 Il I :'' R - C - N - R~ -- O R3 - COOM
:. ,: .' and CH2 . ' R - C N - R~ - OM
. R4 R2 SO3M
ln whlch R ls a hydroearbon group having from 4 to 18 carbon atoms.
.: . - .
Rl, R2 and R3 are selected from the group consisting of a) aliphatic hydrocarbon groups of 1 to 4 carbon atoms, b) hydroxy-substituted aliphatic hydrocarbon groups of 1 to 4 carbon atoms, e) aliphatic hydrocarbon groups having a single ether i 30 linkage and of 2 to 4 carbon atoms, ~1/ -2a-: . .
- ~
-- ~)884Z7 :;
d) hydroxy-substituted aliphatic hydrocarbon groups .-~:
having single ether linkage and of 2 to 4 carbon .,~
atoms, .
e) aliphatic keto groups containing only a single keto : :
linkage and otherwise being hydrocarbon of 2 to 4 ;
carbon atoms, :~ :
f) aliphatic keto groups containing only a single keto linkage and otherwise being hydroxy-substituted hydrocarbon of 2 to 4 carbon atoms . -R4 is selected from the group consisting of a) a hydroxyl group and ;
b) the group -OS03 (CH2CH2O)nR5 in which R~ is a hydrocarbon group containing 8 to 18 carbon :~.
at.oms and n is a whole number from 0 to 4 incluslve, and M is an alkal:L metal. .:.
. ;,, -j : ' : I .
: :
':
.. . .
1~B84Z7 Imidazoline derivatives of this type are well .
known and methods for their preparation are described in :
various U. S. patents issued to Hans S. Mannheimer and are sold by the Miranol Chemical Company under the registered . ~
trademark MIRANOL. :~:
The nonionic surfactants which we use Ln our invention to provide enhanced cleansing abilities without the impartation of eye irritation problems are water soluble block copolymers of polyethylene and polypropylene selected from the group consisting of: ..
(a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight .
o 1,000 - 15,000, ~b) condensation producks of propylene oxide with bases ~ormed by condensing ekhylene oxide with ethylene glycol and having a molecular weight o 1,000 - 10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ,~
ethylenediamine and having a molecular weight of 1,000 - 30,000.
Suractants o this type are described in U.S.
: Patents No. 2,674,619; No. 3,036,118; and No.
2,979,528 and are sold by the BASF Wyandotte : ~
Corp. under the trademarks PLURONIC ~ PLURONIC R ` ; ;
and TETRONIC . .
The anionic surfactants which we use in our .:~
invention to insure the dev~lopment o a rich and copious lather and to promote clarity when the compositions are . -~
formulated at pE~ levels on the acid side are the sulfates ;;
of ethoxylated fatty alcohols having the formula .. :
'" '',:,~
bm:
,` . . .
~ 8427 R - (OCH2CH2)nOSO3M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, preferably 12 to 14, n equals a whole number from 5 to 30 inclusive, preferably 8 to 14, M equals an alkali metal, ammonium or a lower : . .
mono,- di, or trialkanolamlne in which the alkyl groups contain from one to four carbon atoms, preferably sodium . . .
or ammon}um.
As mentioned hereinabove, the 2-alkyl-substituted imidazolines of this invention are well known as detergents for use in the formulation of personal care shampoo products.
While these materials themselves, especially the compound having the structure.
\
¦¦ I ,S~H2CH20Na C l l H 2 3 C -N <
¦ CH2COONa ' OS03 (CH2CH2O)3C13H27 possess an unusually good combination of foaming, cleansing and irritation properties, we have discovered that by limiting the amount of imidazoline used and ~ombining it with at least an equal quantity of a mixture of the nonionic and anionic surfactants described herein, there is produced a composition showing improvement in all three areas, i.e.
foaming, cleansing, and irritation potential.
We have found that useful aqueous shampoo compositions can be based upon solutions of 2-alkyl-30~ substituted imidazoIines containing 6.0 to 15.0% imidazoline by weight. Compositions containing less than -this will be . . .
found to provide sufficient foaming while those containing bm: ~
,' .: ' .
-. ~ , . . .
81!342~ :
more than 15% may cause eye irritation which cannot be effectively reduced by the incorporation of the nonionic- .
anionic detergent mixtures described herein. We prefer to use 8 to 10~ imidazoline.
The nonionic-anionic detergent mixtures, which not only reduce the eye irritation potential of the .
imidazolines but also improve their foaming and cleansing .
properties comprise one or more each of the specified nonionic and anionic detergents described herein in which the weight ratio of the nonionic to anionic components may range . .
from 0.5:1 to 10:1. When it is intended to formulate compositions of this invention at a pH of less than 7.5, it is important that the ratio of nonionic to anionic components not exceed ~:1 to insure that the compositions remain homogeneous, transparent, and non-irritatin~. One o~
the preferred forms of this invention comprises non-. alkaline formulations inaving a pH of 2.0 to 6.0 capable of cle~nsing the ha.ir without signiicantly altering its natural pH balance.
It is necessary that the proportion o~ the total nonionic-anionic detergent mixture to 2-substituted-alkyl-imidazoline be ~t least 1 to 1 to insure signif~cant improvement in shampoo properties. While proportions as high as 5 to 1 may be employed, we prefer to use proportions ranging from 2 to 1 to 3 to 1, to insure low irritation and good lathering at pH levels below 7.5.
Any of the usual additives such as opacifiers, .
perfumes, coloring agents, stabilizers, preservaties, : :
thickeners such as the polyethylene glycol distearates and the like may also be included in the compositions if . :
desired. :
:.
-6~
bm: ~:
4z7 The following specific examples are intended to illustrate more clearly the nature of the invention, but are not intended as a limitation upon the scope of the claims.
Example 1 An aqueous solution was preparecl containing 8.0~ -~
.... ~ .
- of the 2-substituted-alkyl imidazoline sold under the name -~ Miranol~ MHT and having the structure. ~ -- - .: :
:, lo I F ~cH2cH2oNa Cl~H~3 - N CH2COONa .. . ;.
OSO9(CH2CH20)9C~3H27 There was added 10~ by weight of a condensate of ethy lene oxide with a ba~e formed by condensing propylene oxide with propylene glycol sold as Pluronic F-88 (BASF Wyandotte Co.) and 8.0~ by welght of a~ ethoxylated (12 mols) so~ium lauryl ., sulfate sold as Standapol (Henkel Inc.). The composition was thickened by the incorporation of 2.0% polyethylene glycol 6000 distearate.
Evaluation of the shampoo formulation showed it to have very good cleansing and foaming properties with a level of eye irritation potential low enough to enable it to be used on infants.
Example II -::
An aqueous solution was prepared containing 10.0% -of the 2-substituted-alkyl imida~oline sold under the name -~
Miranol~ 2MCAS-modO a~d having the structure ' . :.' .
';:
'" '' '. ' ;i bm:
.::
':
~O~Z7 ~:, .
CHz / \, ', ll ¦ CH2COONa CllH23C I <CH2CH20CH2COONa oso3c,2H2 5 There was added 10% by weight of a condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol sold as Pluronic F-88 (BASF Wyandotte Co.) and 8.0~ by weight of an ethoxylated (12 mols) sodium lauryl sulfate sold as Standapol (Henkel Inc.). The compositlon was thickened by the incorporation of 2.0~ polyethylene glycol 6000 distearate.
Compari~on of the abo~e formulation with thak : described in Example I indicated that while the composition had equivalent cleansing and irritation properties, it was I somewhat less efficien~ in foaming and lathering.
Example,III
.
Ingredient % by Weight ; 20 2-substituted-alkyl-imidazoline ; of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol (Pluronic F-87, BASF
Wyandotte Corp.) 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.) 8.0 Polyethylene glycol 6000 distearate Water To 100.0 bm:
., . ... :
;~
1~J88427 Example IV
Ingredient % by Weight 2-substi~uted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 10.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol ~Pluronic L-64, BASF Wyandotte Corp.~ 14.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)4.0 Polyethylene glycol 6000 distearate 2,0 Water To 100.0 Example V
Ingredient % by Weight 2-substituted-alkyl-imidazoline o~ Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene gylcol (Pluronic F-127, BASF Wyandotte Corp.) 10.0 --:
Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example VI
In~redient ~ by Weight 2-substituted-alkyl-imidazoline of Example II (Miranol 2MCAS-mod., Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol (Pluronic :-F-127, BASF Wyandotte Corp.) 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 :' ~g_ : , bm:
~L0884Z~7 -:
Example VII
Ingredient ~ by Weight ~-2-substituted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensation product of ethylene oxide with a base formed by condensing propylene oxide with ethylenediamine (Tetronic 704, BASF ~yandotte Corp.~ 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example VIII
Ingredient % by Weight 2-substituted-alkyl-imidazoline of Example I (Miranol MEIT, Miranol Chemical Co.) 8. n : Condensation product of ethylene oxide with a base formed by condensing propyLene oxide with ethylenediamine ~Tetronic 707; B~SF ~Iyandotte Corp.) 8.0 -Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example IX
In~redient % by Wei~ht 2-substituted-alkyl-imidazoline of Example I ~Miranol ME~T, Miranol Chemical Co.) 8.0 Condensation product of ethylene oxide with a base formed by condensing propylene oxide with ethylenediamine (Tetronic 707; BASF Wyandotte Corp.) 8.0 -Ethoxylated (12 mols) sodium lauryl i sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 bm:
108~ 7 Example X
Ingredient % by Weight :. :
2-substituted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensation product of propylene oxide with a base formed by condensing `~
ethylene oxide with ethylene glycol (Pluronic 17R~, BASF ~yandotte Corp.) 8.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 '. .- '.
While the compositions of Examples III through X
exhibit variations in relative cleansing and foaming abilities, all are satisfactory or use as hair æhampoo compositions and all exhibit eye irritation properties superior to the 2-substituted-alkyl-imidazolines alone.
Although the present invention has been described ~p; with reference to particular embodiments and examples, it will be apparent to those skilled in the art that variations ;
and modifications can be substituted therefor without departing from the principles and the true spirit of the invention.
,' ~
'~
, ' ~" ', bm: ;
. .
Corp. under the trademarks PLURONIC ~ PLURONIC R ` ; ;
and TETRONIC . .
The anionic surfactants which we use in our .:~
invention to insure the dev~lopment o a rich and copious lather and to promote clarity when the compositions are . -~
formulated at pE~ levels on the acid side are the sulfates ;;
of ethoxylated fatty alcohols having the formula .. :
'" '',:,~
bm:
,` . . .
~ 8427 R - (OCH2CH2)nOSO3M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, preferably 12 to 14, n equals a whole number from 5 to 30 inclusive, preferably 8 to 14, M equals an alkali metal, ammonium or a lower : . .
mono,- di, or trialkanolamlne in which the alkyl groups contain from one to four carbon atoms, preferably sodium . . .
or ammon}um.
As mentioned hereinabove, the 2-alkyl-substituted imidazolines of this invention are well known as detergents for use in the formulation of personal care shampoo products.
While these materials themselves, especially the compound having the structure.
\
¦¦ I ,S~H2CH20Na C l l H 2 3 C -N <
¦ CH2COONa ' OS03 (CH2CH2O)3C13H27 possess an unusually good combination of foaming, cleansing and irritation properties, we have discovered that by limiting the amount of imidazoline used and ~ombining it with at least an equal quantity of a mixture of the nonionic and anionic surfactants described herein, there is produced a composition showing improvement in all three areas, i.e.
foaming, cleansing, and irritation potential.
We have found that useful aqueous shampoo compositions can be based upon solutions of 2-alkyl-30~ substituted imidazoIines containing 6.0 to 15.0% imidazoline by weight. Compositions containing less than -this will be . . .
found to provide sufficient foaming while those containing bm: ~
,' .: ' .
-. ~ , . . .
81!342~ :
more than 15% may cause eye irritation which cannot be effectively reduced by the incorporation of the nonionic- .
anionic detergent mixtures described herein. We prefer to use 8 to 10~ imidazoline.
The nonionic-anionic detergent mixtures, which not only reduce the eye irritation potential of the .
imidazolines but also improve their foaming and cleansing .
properties comprise one or more each of the specified nonionic and anionic detergents described herein in which the weight ratio of the nonionic to anionic components may range . .
from 0.5:1 to 10:1. When it is intended to formulate compositions of this invention at a pH of less than 7.5, it is important that the ratio of nonionic to anionic components not exceed ~:1 to insure that the compositions remain homogeneous, transparent, and non-irritatin~. One o~
the preferred forms of this invention comprises non-. alkaline formulations inaving a pH of 2.0 to 6.0 capable of cle~nsing the ha.ir without signiicantly altering its natural pH balance.
It is necessary that the proportion o~ the total nonionic-anionic detergent mixture to 2-substituted-alkyl-imidazoline be ~t least 1 to 1 to insure signif~cant improvement in shampoo properties. While proportions as high as 5 to 1 may be employed, we prefer to use proportions ranging from 2 to 1 to 3 to 1, to insure low irritation and good lathering at pH levels below 7.5.
Any of the usual additives such as opacifiers, .
perfumes, coloring agents, stabilizers, preservaties, : :
thickeners such as the polyethylene glycol distearates and the like may also be included in the compositions if . :
desired. :
:.
-6~
bm: ~:
4z7 The following specific examples are intended to illustrate more clearly the nature of the invention, but are not intended as a limitation upon the scope of the claims.
Example 1 An aqueous solution was preparecl containing 8.0~ -~
.... ~ .
- of the 2-substituted-alkyl imidazoline sold under the name -~ Miranol~ MHT and having the structure. ~ -- - .: :
:, lo I F ~cH2cH2oNa Cl~H~3 - N CH2COONa .. . ;.
OSO9(CH2CH20)9C~3H27 There was added 10~ by weight of a condensate of ethy lene oxide with a ba~e formed by condensing propylene oxide with propylene glycol sold as Pluronic F-88 (BASF Wyandotte Co.) and 8.0~ by welght of a~ ethoxylated (12 mols) so~ium lauryl ., sulfate sold as Standapol (Henkel Inc.). The composition was thickened by the incorporation of 2.0% polyethylene glycol 6000 distearate.
Evaluation of the shampoo formulation showed it to have very good cleansing and foaming properties with a level of eye irritation potential low enough to enable it to be used on infants.
Example II -::
An aqueous solution was prepared containing 10.0% -of the 2-substituted-alkyl imida~oline sold under the name -~
Miranol~ 2MCAS-modO a~d having the structure ' . :.' .
';:
'" '' '. ' ;i bm:
.::
':
~O~Z7 ~:, .
CHz / \, ', ll ¦ CH2COONa CllH23C I <CH2CH20CH2COONa oso3c,2H2 5 There was added 10% by weight of a condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol sold as Pluronic F-88 (BASF Wyandotte Co.) and 8.0~ by weight of an ethoxylated (12 mols) sodium lauryl sulfate sold as Standapol (Henkel Inc.). The compositlon was thickened by the incorporation of 2.0~ polyethylene glycol 6000 distearate.
Compari~on of the abo~e formulation with thak : described in Example I indicated that while the composition had equivalent cleansing and irritation properties, it was I somewhat less efficien~ in foaming and lathering.
Example,III
.
Ingredient % by Weight ; 20 2-substituted-alkyl-imidazoline ; of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol (Pluronic F-87, BASF
Wyandotte Corp.) 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.) 8.0 Polyethylene glycol 6000 distearate Water To 100.0 bm:
., . ... :
;~
1~J88427 Example IV
Ingredient % by Weight 2-substi~uted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 10.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol ~Pluronic L-64, BASF Wyandotte Corp.~ 14.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)4.0 Polyethylene glycol 6000 distearate 2,0 Water To 100.0 Example V
Ingredient % by Weight 2-substituted-alkyl-imidazoline o~ Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene gylcol (Pluronic F-127, BASF Wyandotte Corp.) 10.0 --:
Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example VI
In~redient ~ by Weight 2-substituted-alkyl-imidazoline of Example II (Miranol 2MCAS-mod., Miranol Chemical Co.) 8.0 Condensate of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol (Pluronic :-F-127, BASF Wyandotte Corp.) 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 :' ~g_ : , bm:
~L0884Z~7 -:
Example VII
Ingredient ~ by Weight ~-2-substituted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensation product of ethylene oxide with a base formed by condensing propylene oxide with ethylenediamine (Tetronic 704, BASF ~yandotte Corp.~ 10.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)8.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example VIII
Ingredient % by Weight 2-substituted-alkyl-imidazoline of Example I (Miranol MEIT, Miranol Chemical Co.) 8. n : Condensation product of ethylene oxide with a base formed by condensing propyLene oxide with ethylenediamine ~Tetronic 707; B~SF ~Iyandotte Corp.) 8.0 -Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 Example IX
In~redient % by Wei~ht 2-substituted-alkyl-imidazoline of Example I ~Miranol ME~T, Miranol Chemical Co.) 8.0 Condensation product of ethylene oxide with a base formed by condensing propylene oxide with ethylenediamine (Tetronic 707; BASF Wyandotte Corp.) 8.0 -Ethoxylated (12 mols) sodium lauryl i sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 bm:
108~ 7 Example X
Ingredient % by Weight :. :
2-substituted-alkyl-imidazoline of Example I (Miranol MHT, Miranol Chemical Co.) 8.0 Condensation product of propylene oxide with a base formed by condensing `~
ethylene oxide with ethylene glycol (Pluronic 17R~, BASF ~yandotte Corp.) 8.0 Ethoxylated (12 mols) sodium lauryl sulfate (Standapol, Henkel Inc.)10.0 Polyethylene glycol 6000 distearate 2.0 Water To 100.0 '. .- '.
While the compositions of Examples III through X
exhibit variations in relative cleansing and foaming abilities, all are satisfactory or use as hair æhampoo compositions and all exhibit eye irritation properties superior to the 2-substituted-alkyl-imidazolines alone.
Although the present invention has been described ~p; with reference to particular embodiments and examples, it will be apparent to those skilled in the art that variations ;
and modifications can be substituted therefor without departing from the principles and the true spirit of the invention.
,' ~
'~
, ' ~" ', bm: ;
. .
Claims (10)
OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An aqueous shampoo composition exhibiting reduced levels of eye irritation which comprises water in combination with an ampholytic surfactant comprising a 2-alkyl-substituted imidazoline, a nonionic surfactant comprising a polyoxyethylene-polyoxypropylene block copolymer and an anionic surfactant comprising an alcohol ether sulfate, the quantity of said ampholytic surfactant being 6.0 to 15.0% by weight, The weight ratio of said nonionic surfactant to said anionic surfactant being 0.5:1 to 10:1 and the proportion of the total of said nonionic surfactant and anionic surfactant to said ampholytic surfactant being 1:1 to 5:1.
2. An aqueous shampoo composition as described in Claim 1 in which said ampholytic surfactant comprises a member of the class consisting of compounds having the structures and in which R is a hydrocarbon group having from 4 to 18 carbon atoms R1, R2 and R3 are selected from the group consisting of a) aliphatic hydrocarbon groups of 1 to 4 carbon atoms, b) hydroxy-substituted aliphatic hydrocarbon groups of 1 to 4 carbon atoms, c) aliphatic hydrocarbon groups having a single ether linkage and of 2 to 4 carbon atoms, d) hydroxy-substituted aliphatic hydrocarbon groups having single ether linkage and of 2 to 4 carbon atoms, e) aliphatic keto groups containing only a single keto linkage and otherwise being hydrocarbon of 2 to 4 carbon atoms, f) aliphatic keto groups containing only a single keto linkage and otherwise being hydroxy-substituted hydrocarbon of 2 to 4 carbon atoms.
R4 is selected from the group consisting of a) a hydroxyl group and b) the group -OSO3(CH2CH2O)nR5 in which R5 is a hydrocarbon group containing 8 to 18 carbon atoms and n is a whole number from 0 to 4 inclusive, and M is an alkali metal or hydrogen.
R4 is selected from the group consisting of a) a hydroxyl group and b) the group -OSO3(CH2CH2O)nR5 in which R5 is a hydrocarbon group containing 8 to 18 carbon atoms and n is a whole number from 0 to 4 inclusive, and M is an alkali metal or hydrogen.
3. An aqueous composition as described in Claim 1 in which said nonionic surfactant is a member of the class consisting of (a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight of 1,000 - 15,000, (b) condensation products of propylene oxide with bases formed by condensing ethylene oxide with ethylene glycol and having a molecular weight of 1,000 - 10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ethylenediamine and having a molecular weight of 1,000 - 30,000.
4. An aqueous shampoo composition as described in Claim 1 in which said anionic surfactant is a member of the class having the formula R - (OCH2CH2)nOSO3M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms.
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms.
5. An aqueous shampoo composition as described in Claim 1 in which said ampholytic surfactant comprises a member of the class consisting of compounds having the structures and in which R is a hydrocarbon group having from 4 to 18 carbon atoms, R1, R2 and R3 are selected from the group consisting of a) aliphatic hydrocarbon groups of 1 to 4 carbon atoms, b) hydroxy-substituted aliphatic hydrocarbon groups of 1 to 4 carbon atoms, c) aliphatic hydrocarbon groups having a single ether linkage and of 2 to 4 carbon atoms, d) hydroxy-substituted aliphatic hydrocarbon groups having single ether linkage and of 2 to 4 carbon atoms, e) aliphatic keto groups containing only a single keto linkage and otherwise being hydrocarbon of 2 to 4 carbon atoms, f) aliphatic keto groups containing only a single keto linkage and otherwise being hydroxy-substituted hydrocarbon of 2 to 4 carbon atoms.
R4 is selected from the group consisting of a) a hydroxyl group and b) the group -OSO3 (CH2CH2O)nR5 in which R5 is a hydrocarbon group containing 8 to 18 carbon atoms and n is a whole number from 0 to 4 inclusive and M is an alkali metal or hydrogen, in which said nonionic surfactant is a member of the class consisting of (a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight of 1,000 -15,000, (b) condensation products of propylene oxide with bases formed by condensing ethylene oxide with ethylene glycol and having a molecular weight of 1,000 -10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ethylene diamine and having a molecular weight of 1,000 -30,000, and in which said anionic surfactant is a member of the class having the formula R - (0CH2CH2)nOSO3M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms.
R4 is selected from the group consisting of a) a hydroxyl group and b) the group -OSO3 (CH2CH2O)nR5 in which R5 is a hydrocarbon group containing 8 to 18 carbon atoms and n is a whole number from 0 to 4 inclusive and M is an alkali metal or hydrogen, in which said nonionic surfactant is a member of the class consisting of (a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight of 1,000 -15,000, (b) condensation products of propylene oxide with bases formed by condensing ethylene oxide with ethylene glycol and having a molecular weight of 1,000 -10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ethylene diamine and having a molecular weight of 1,000 -30,000, and in which said anionic surfactant is a member of the class having the formula R - (0CH2CH2)nOSO3M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms.
6. An aqueous shampoo composition as described in Claim 1 in which said ampholytic surfactant comprises the compound having the structure in which said nonionic surfactant is a member of the class consisting of (a) condensation products of ethylene oxide with bases formed by condensing propylene oxide with propylene glycol, and having a molecular weight of 1,000 -15,000, (b) condensation products of propylene oxide with bases formed by condensing ethylene oxide with ethylene glycol and having a molecular weight of 1,000 -10,000, and (c) condensation products of ethylene oxide with bases formed by condensing propylene oxide with ethylene-diamine and having a molecular weight of l,000 -30,000, and in which said anionic surfactant is a member of the class having the formula R - (OCH2CH2)nOSO3M
where R equals a hydrocarbon radical of 12 to 14 carbon atoms, n equals a whole number from 8 to 14 inclusive, and M equals sodium or ammonium.
where R equals a hydrocarbon radical of 12 to 14 carbon atoms, n equals a whole number from 8 to 14 inclusive, and M equals sodium or ammonium.
7. An aqueous shampoo composition as described in Claim 6 in which the proportion of the total nonionic surfactant and anionic surfactant to ampholytic surfactant is 2:1 to 3:1.
8. An aqueous shampoo composition as described in Claim 6 in which the ratio of said nonionic surfactant to said anionic surfactant does not exceed 4:1, said composition having a pH
not exceeding 7.5.
not exceeding 7.5.
9. An aqueous shampoo composition as described in Claim 1 in which said ampholytic surfactant is the compound having the structure in which the nonionic surfactant is a condensation product of ethylene oxide with a base formed by condensing propylene oxide with propylene glycol and having a molecular weight, of 1,000 to 15,000, in which said anionic surfactant is a member of the class having the formula R - (OCH2CH2)nOSO9M
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 Inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms, in which the proportion of the total of said nonionic surfactant and anionic surfactant to said ampholytic surfactant is 2:1 to 3:1, in which the proportion of said nonionic surfactant to said anionic surfactant does not exceed 4:1, said composition having a pH of 2.0 to 6Ø
where R equals a hydrocarbon radical of 4 to 18 carbon atoms, n equals a whole number from 5 to 30 Inclusive, and M equals an alkali metal, ammonium or a lower mono, di, or tri-alkanolamine in which the alkyl groups contain from one to four carbon atoms, in which the proportion of the total of said nonionic surfactant and anionic surfactant to said ampholytic surfactant is 2:1 to 3:1, in which the proportion of said nonionic surfactant to said anionic surfactant does not exceed 4:1, said composition having a pH of 2.0 to 6Ø
10. An aqueous shampoo composition as described in Claim 9 in which said ampholytic surfactant comprises 8 to 10 percent by weight.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64330575A | 1975-12-22 | 1975-12-22 | |
| US643,305 | 1975-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088427A true CA1088427A (en) | 1980-10-28 |
Family
ID=24580223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA266,311A Expired CA1088427A (en) | 1975-12-22 | 1976-11-23 | Imidazoline-containing hair shampoo compositions |
Country Status (5)
| Country | Link |
|---|---|
| AU (1) | AU509703B2 (en) |
| CA (1) | CA1088427A (en) |
| ES (1) | ES454457A1 (en) |
| FR (1) | FR2336475A1 (en) |
| GB (1) | GB1508929A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5795354A (en) * | 1987-03-25 | 1998-08-18 | Commonwealth Scientific And Industrial Research Organization | Process for dyeing wool and other keratin fibres |
| US5269974A (en) * | 1992-09-01 | 1993-12-14 | The Procter & Gamble Company | Liquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions |
| US5756439A (en) * | 1996-03-18 | 1998-05-26 | Lever Brothers Company, Division Of Conopco, Inc. | Liquid compositions comprising copolymer mildness actives |
| WO2007104173A2 (en) * | 2006-03-10 | 2007-09-20 | Laboswiss Ag | Method for solubilizing, dispersing, and stabilizing materials, products manufactured according to said method, and use thereof |
| SG177603A1 (en) | 2009-08-03 | 2012-02-28 | Innospec Ltd | Composition |
| US8685906B2 (en) | 2009-08-03 | 2014-04-01 | Innospec Limited | Low irritancy cleansing compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH377468A (en) * | 1959-03-04 | 1964-06-30 | Waclav Dr Silberman | Process for the production of a liquid, low-foaming and dry-gloss imparting detergent, in particular for dish washing machines, and the use of this detergent |
| US3118842A (en) * | 1959-07-13 | 1964-01-21 | Marveli Ind | Multi-purpose cleaner-germicide-deodorizer composition |
| US3740421A (en) * | 1966-09-19 | 1973-06-19 | Basf Wyandotte Corp | Polyoxyethylene-polyoxypropylene aqueous gels |
| JPS518644B2 (en) * | 1972-07-19 | 1976-03-18 | ||
| US3928251A (en) * | 1972-12-11 | 1975-12-23 | Procter & Gamble | Mild shampoo compositions |
| CA1027479A (en) * | 1973-11-19 | 1978-03-07 | Frank A. Nowak (Jr.) | Shampoo composition |
-
1976
- 1976-11-23 CA CA266,311A patent/CA1088427A/en not_active Expired
- 1976-11-30 GB GB4993476A patent/GB1508929A/en not_active Expired
- 1976-12-15 AU AU20572/76A patent/AU509703B2/en not_active Expired
- 1976-12-21 FR FR7638494A patent/FR2336475A1/en active Granted
- 1976-12-21 ES ES454457A patent/ES454457A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1508929A (en) | 1978-04-26 |
| AU509703B2 (en) | 1980-05-22 |
| FR2336475B1 (en) | 1980-12-12 |
| FR2336475A1 (en) | 1977-07-22 |
| ES454457A1 (en) | 1978-06-01 |
| AU2057276A (en) | 1978-06-22 |
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