Use of cationic surfactants in cosmetic preparations

Information

  • Patent Grant
  • 8388986
  • Patent Number
    8,388,986
  • Date Filed
    Thursday, August 9, 2001
    24 years ago
  • Date Issued
    Tuesday, March 5, 2013
    12 years ago
Abstract
The invention relates to a new use of cationic surfactants derived from the condensation of fatty acids and esterified dibasic amino acids, according to the following formula:
Description
RELATED APPLICATION DATA

This application is a national phase application under 35 U.S.C. 371 of PCT/EP01/09198, filed Aug. 9, 2001.


FIELD OF THE INVENTION

This invention relates to a novel use of cationic surfactants and preparations according to this novel use.


BACKGROUND OF THE INVENTION

Due to their composition, many cosmetic products are susceptible to act as a culture medium for microorganisms, and this can cause possible alterations to the cosmetic preparation and constitute a possible risk to human heath as well. Thus, a cosmetic composition requires good protection against microbiological contamination.


A well-known substance used for the protection against microorganisms is a cationic surfactant derived from lauric acid and arginine, in particular, the ethyl ester of the lauramide of the arginine monohydrochloride, hereafter named LAE. The chemical structure is described in the following formula:




embedded image


This compound is remarkable for its activity against different microorganisms, such as bacteria, fungi and yeasts and its use is known in food and feed preparations. The compound is well-known to be harmless to animals and humans. The minimum inhibitory concentrations of LAE are shown in the following table 1.











TABLE 1







M.I.C.


Kind
Microorganism
(ppm)

















Gram + Bacteria

Arthrobacter oxydans ATCC 8010

64




Bacillus cereus var mycoide ATCC 11778

32




Bacillus subtilis ATCC 6633

16




Clostridium perfringens ATCC 77454

16




Listeria monocytogenes ATCC 7644

10




Staphylococcus aureus ATCC 6538

32




Micrococcus luteus ATCC 9631

128




Lactobacillus delbrueckii ssp lactis CECT 372

16




Leuconostoc mesenteroides CETC 912

32


Gram − Bacteria

Alcaligenes faecalis ATCC 8750

64




Bordetella bronchiseptica ATCC 4617

128




Citrobacter freundii ATCC 22636

64




Enterobacter aerogenes CECT 689

32




Escherichia coli ATCC 8739

32




Escherichia coli 0157H7

20




Klebsiella pneumoniae var pneumoniae

32



CECT 178





Proteus mirabilis CECT 170

32




Pseudomonas aeruginosa ATCC 9027

64




Salmonella typhimurium ATCC 16028

32




Serratia marcenses CECT 274

32




Mycobacterium phlei ATCC 41423

2


Fungi

Aspergillus niger ATCC 14604

32




Aureobasidium pullulans ATCC 9348

16




Gliocadium virens ATCC 4645

32




Chaetonium globosum ATCC 6205

16




Penicillium chrysogenum CECT 2802

128




Penicillium funiculosum CECT 2914

16


Yeast

Candida albicans ATCC 10231

16




Rhodotorula rubra CECT 1158

16




Saccharomyces cerevisiae ATCC 9763

32














DETAILED DESCRIPTION

It has now been detected that the product LAE and related compounds are particularly suitable to be used in cosmetic preparations.


The use of the invention relates to cationic surfactants derived from the condensation of fatty acids and esterified dibasic amino acids, according to the following formula:




embedded image



where:


X is Br, Cl, or HSO4

R1: is a linear alkyl chain from a saturated fatty acid or hydroxyacid from 8 to 14 atoms of carbon bonded to the α-amino acid group through an amidic bond.


R2: is a linear or branched alkyl chain from 1 to 18 carbon atoms or an aromatic group.


R3: is:




embedded image



and n can be from 0 to 4.


The most preferred compound of the above class of compounds is LAE.


LAE can be used in cosmetic formulations and preparations that are applied in the epidermis, the capillary system, lips, nails, external genital organs, or in the teeth and mouth cavity mucous, in order to clean, perfume, or modify its aspect and/or change corporal smells and/or protect a good physical fitness. At the same time LAE inhibits the growth of microorganisms in the cosmetic formulations and preparations in which they are susceptible to develop, and also from the microorganisms that can be introduced by the practical use of the customer.


The compositions of the invention have a medium which is compatible with the skin, the mucous membranes, and hair. These compositions can have the classical components such as: fatty compounds such as mineral oil, animals oil, vegetal oil, synthesis and silicon oils, and also alcohols, fatty acids and waxes; organic solvents, surface active agents, solubilizers and ionic and non ionic emulsifiers, thickening agents and jellying hydrophilic agents such as carboxyvinylic polymers (e.g. carbomer), acrylic copolymers (e.g. acrylates and alkylacrylates), polyacrylamides, polysaccharides, natural gums (e.g. xanthan gum); thickening agents and jellying lipophilic agents such as modified clays (e.g. bentonite), fatty acid metallic salts, hydrophobic silica and polyethylene; perfumes and essential oils; softening agents; excipients; antioxidants; sequestering agents; opacifiers; filters; colouring compounds which may be either hydrosoluble or liposoluble, and pigments; and hydrophilic or lipophilic active ingredients. These compositions can also contain further preservatives besides the ones used according to the invention.


The proportions of the components mentioned in the previous paragraph are the ones normally used in the mentioned applications. These components have to be applied without changing the preservative system of the invention.


According to the invention the compositions can be in different cosmetic forms suitable for a topic application, such as:

    • a) Monophasic systems:
      • Aqueous or hydroglycolic solution that contain one or more surfactants to be used for the cleaning of the skin, hair and mucous membranes;
      • Aqueous, hydroalcoholic, hydroglycolic or oily solution that can contain other additives to be used in the general care and/or protection for skin and/or mucous membranes;
      • Aqueous, hydroalcoholic, hydroglycolic or oily gel that can contain other additives to be used in general care and/or protection for skin and/or mucous membranes;
      • Solid anhydride products that can contain other additives to be used in the general care and/or protection for skin and/or mucous membranes;
    • b) Biphasic systems:
      • Aqueous, hydroalcoholic, hydroglycolic or oily gel that can contain other additives to be used in general care and/or protection for skin and/or mucous membranes;
      • Solid anhydride products that can contain other additives to be used in the general care and/or protection for skin and/or mucous membranes;
      • Emulsions formed by dispersion of a oil phase in a water phase (O/W) or inverse phase (W/O), to be used in general care and/or protection of the face skin, body, hands and/or mucous; cleaning and/or removal of make-up from the skin, mucous membranes, hair and/or mouth cavity; protection and/or skin care against solar radiation effects; colouring support and pigment to be applied to the skin.
    • c) And combinations of the other systems that form multiphasic systems, suspensions and microemulsions.


The compositions previously mentioned can be used in different forms such as foam, spray, or aerosol compositions and can contain a propulsion agent under pressure.


Thus, the compositions of the invention can have the aspect of a cream, a lotion, a milk, an emulsion, a gel or an oil for the skin, a beauty mask, a salt, a gel, a foam/spray or an oil for bath and shower, or for making up and making-up cleaner for the face and eyes and any other aspect known in the art.


The compositions according to the invention have been prepared according to the techniques well known for a person skilled in the art.


Procedure to Evaluate the Preservative Efficacy for LAE

The method is based on the Antimicrobial Effectiveness Testing USP 24th Edition, 1999 (pp. 1809-1811), in order to demonstrate that the antimicrobial activity of the compound aim of the patent is enough to avoid the microbial growth that could have in the storage and use of the preparation, preventing the adverse effects of the contamination (Real Farmacopea Española, 1st Edición, 1997).


This assay consists of the contamination of the protecting formulations with an inoculum mixture of 108 cfu/mL concentration, for each of the microorganisms, and the determination of the number of viable cells in the time. This inoculum mixture is composed of the following microorganisms:


















Pseudomonas aeruginosa

ATCC 9027




Staphylococcus aureus

ATCC 6538




Candida albicans

ATCC 10231




Aspergillus niger

ATCC 16404




Escherichia coli

ATCC 8739









The cosmetic composition to be analysed is divided into sterile containers with 50 g of product for each flask. Each container is inoculated with 0.5 mL of inoculum (108 cfu/mL). The target concentration is 106 cfu/mL, approximately. All the containers are kept at a temperature between 20-25° C. and are protected from light.


The level of the microbial contamination is checked at 0 hours, 7 days, 14 days and 28 days. The number of colonies is evaluated by dilution in buffer peptone with the appropriate neutraliser agent of the preservative. The culture media used for counting the microorganisms are: Soya triptone (35-37° C., 48 hours) for the determination of bacteria; Sabouraud agar with chloramphenicol for fungi and yeast (25° C., 3-5 days).


According to Antimicrobial Effectiveness Testing USP 24th Edition, 1999 (pp. 1809-1811), an antimicrobial preservative is considered to be effective in topically used products made with aqueous bases or vehicles, non-sterile nasal products and emulsions, including those applied to mucous membranes, if:

    • Not less than 2.0 logarithm reduction from the initial calculated bacteria's count is reached at 14 days and no increase from the 14 days' count at 28 days is detected; and
    • No increase from the initial calculated count of yeast and moulds is observed.


EXAMPLES

Different examples of cosmetic preparations and formulations are provided where the product has been assayed. Theses examples are a part of the preparations and formulations assayed.


Example 1

The composition of the cosmetic formulation in oil-in-water emulsion with non-ionic surfactant, is (in g):



















Polysorbate 60
3.00




Sorbitan stearate
2.00




Cetyl alcohol
1.00




Paraffinum
3.00




Isopropyl mirystate
3.00




Caprylic-caproic triglycerides
3.00




Dimethicone
0.50




Propylene glycol
3.00




Cellulose gum
0.25




Carbomer 940
0.10




Triethanolamine
0.10




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the table 2.













TABLE 2









With





Without LAE
LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
2.1 · 106
1.1 · 106




Fungi
1.6 · 104
1.7 · 104




Yeast
3.7 · 105
5.6 · 105



7 days
Aerobes
2.1 · 106
3.1 · 103




Fungi
7.0 · 102
<9.9 · 101




Yeast
8.2 · 103
9.5 · 102



14 days
Aerobes
6.2 · 106
3.3 · 102




Fungi
5.9 · 102
<9.9 · 101




Yeast
4.8 · 103
4.0 · 102









At 28 days no increase has been detected from the 14 days' count.


Example 2

The composition of an oil-in-water emulsion with an ionic emulsifier, used as cosmetic formulation, is (in g):



















Stearic acid
1.70




Glyceryl stearate S.E.
2.50




Cetyl alcohol
1.50




Paraffinum
3.00




Isopropyl myristate
3.00




Caprylic-caproic triglycerides
3.00




Dimethicone
0.50




Propylene glycol
3.00




Cellulose gum
0.50




Triethanolamine
1.03




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the table 3.













TABLE 3









With





Without LAE
LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
7.4 · 106
2.7 · 106




Fungi
2.0 · 104
1.4 · 104




Yeast
3.6 · 104
3.6 · 104



7 days
Aerobes
5.2 · 106
1.6 · 104




Fungi
8.8 · 102
<9.9 · 101




Yeast
4.7 · 104
1.0 · 102



14 days
Aerobes
1.7 · 107
6.5 · 102




Fungi
7.0 · 102
<9.9 · 101




Yeast
1.0 · 104
1.0 · 102









At 28 days no increase has been detected from the 14 days' count.


Example 3

The general composition for a cosmetic formulation, in water in oil emulsion with non-ionic emulsifiers, is (in g)



















Cetyl Dimethicone copolyol
3.00




Isohexadecane
6.00




Paraffinum
8.00




Isopropyl myristate
6.00




Caprylic-caproic triglycerides
4.00




Glycerin
5.00




Sodium chloride
0.50




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 4.













TABLE 4








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
1.6 · 106
 6.2 · 106




Fungi
2.0 · 104
 1.0 · 104




Yeast
3.8 · 104
 7.0 · 104



7 days
Aerobes
1.1 · 106
 1.8 · 103




Fungi
5.0 · 102
<9.9 · 101




Yeast
9.0 · 102
<9.9 · 101



14 days
Aerobes
8.7 · 106
<9.9 · 101




Fungi
3.0 · 102
<9.9 · 101




Yeast
3.0 · 102
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 4

The composition of a formulation to obtain an aqueous solution with a surfactants' mixture, is (in g):



















Sodium lauryl sulfate (sol. 27%)
14.00




Cocamidopropyl betaine
6.00




Disodium cocoamfoacetate
6.00




Lactic acid
0.25




Sodium chloride
0.50




Aqua
100
c.s.p.










This formulation is applied in bath gels.


This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 5.













TABLE 5








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
3.6 · 106
 3.3 · 106




Fungi
1.6 · 104
 1.9 · 104




Yeast
3.9 · 104
 4.6 · 104



7 days
Aerobes
4.2 · 106
 5.8 · 103




Fungi
2.7 · 103
 2.7 · 102




Yeast
4.5 · 103
<9.9 · 101



14 days
Aerobes
5.5 · 106
<9.9 · 101




Fungi
3.4 · 103
<9.9 · 101




Yeast
5.9 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 5

The composition of a formulation to obtain an aqueous solution with a surfactants' mixture, is (in g):



















Sodium lauryl sulfate (sol. 27%)
14.00




Cocamidopropyl betaine
6.00




Disodium lauryl sulfosuccinate
6.00




Lactic acid
0.25




Sodium chloride
0.50




Aqua
100
c.s.p.










This formulation is applied in bath gels.


This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 6.













TABLE 6








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
8.6 · 106
6.7 · 106




Fungi
1.1 · 104
1.4 · 104




Yeast
3.2 · 104
3.6 · 104



7 days
Aerobes
3.9 · 107
4.8 · 102




Fungi
1.6 · 103
<9.9 · 101




Yeast
3.1 · 103
<9.9 · 101



14 days
Aerobes
3.3 · 106
1.3 · 102




Fungi
8.3 · 103
<9.9 · 101




Yeast
3.9 · 104
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 6

The composition of a formulation to obtain a hydroalcoholic gel, is (in g):



















Hydroxyethyl cellulose
0.40




Carbomer 940
0.40




Glycerin
8.00




Alcohol denat
30.00




PEG 40 hydrogenated castor oil
1.50




Parfum
0.75




Triethanolamine
0.25




Aqua
100
c.s.p.










This formulation is applied in lotions for after-shaving skin care.


This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 7.













TABLE 7








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
1.1 · 106
3.7 · 106




Fungi
8.7 · 104
9.1 · 104




Yeast
3.9 · 104
4.2 · 104



7 days
Aerobes
4.6 · 106
6.9 · 103




Fungi
9.1 · 103
4.1 · 102




Yeast
8.6 · 102
1.6 · 102



14 days
Aerobes
7.3 · 106
<9.9 · 101




Fungi
1.7 · 103
<9.9 · 101




Yeast
1.2 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 7

The composition of a formulation to obtain a facial tonic, is (in g):



















Hydroxyethyl cellulose
0.20




Caprylic-caproic triglycerides
1.00




PEG 40 hydrogenated castor oil
6.00




Lactic acid
1.00




Sodium chloride
0.35




Glycerin
3.00




Chamomilla Recutita extract
3.00




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 8.













TABLE 8








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
6.7 · 106
2.7 · 106




Fungi
4.1 · 104
2.1 · 104




Yeast
3.2 · 104
1.2 · 104



7 days
Aerobes
3.7 · 107
3.6 · 103




Fungi
9.1 · 103
1.3 · 102




Yeast
4.2 · 103
1.1 · 102



14 days
Aerobes
8.7 · 107
5.9 · 102




Fungi
2.1 · 104
<9.9 · 101




Yeast
1.2 · 104
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 8

The composition of a formulation to obtain a mask-up cleaner, is (in g):



















Stearic acid
2.00




Glyceryl stearate S.E
2.50




Cetyl alcohol
1.50




Paraffinum
6.00




Isopropyl myristate
1.50




Caprylic-caproic triglycerides
1.50




Dimethicone
0.50




Propylene glycol
3.00




Triethanolamine
1.20




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 9.













TABLE 9








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
5.5 · 106
4.5 · 106




Fungi
7.9 · 104
7.6 · 104




Yeast
8.4 · 104
7.2 · 104



7 days
Aerobes
6.5 · 106
3.8 · 103




Fungi
8.2 · 102
3.5 · 102




Yeast
8.8 · 102
1.8 · 102



14 days
Aerobes
9.5 · 106
6.7 · 102




Fungi
2.9 · 103
<9.9 · 101




Yeast
1.8 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 9

The composition of a formulation to obtain a fluid oil-in-water emulsion with non-ionic surfactants, is (in g):



















Polysorbate 60
3.00




Sorbitan stearate
2.00




Cetyl alcohol
0.75




Paraffinum
3.00




Isopropyl myristate
2.50




Caprylic-caproic triglycerides
2.00




Dimethicone
0.50




Propylene glycol
3.00




Aqua
100
c.s.p.










This formulation is applied in body oil.


This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 10.













TABLE 10








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
1.5 · 106
4.5 · 106




Fungi
2.6 · 104
7.6 · 104




Yeast
3.2 · 104
7.2 · 104



7 days
Aerobes
4.5 · 106
7.6 · 103




Fungi
7.7 · 103
1.4 · 102




Yeast
8.4 · 103
2.3 · 102



14 days
Aerobes
6.3 · 106
<9.9 · 101




Fungi
1.6 · 104
<9.9 · 101




Yeast
7.9 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 10

The composition of a toothpaste formulation is (in g):



















Calcium carbonate
16.00




Dicalcium phosphate
24.00




Silica
2.00




Petrolatum
10.00




Glycerine
20.00




Sodium fluoride
0.20




Hydroxyethyl cellulose
1.00




Lauroyl sarcosine
2.00




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 11.













TABLE 11








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
6.5 · 106
4.5 · 106




Fungi
9.6 · 104
5.6 · 104




Yeast
4.8 · 104
4.2 · 104



7 days
Aerobes
3.5 · 107
3.3 · 103




Fungi
1.6 · 104
1.6 · 102




Yeast
5.2 · 103
1.2 · 102



14 days
Aerobes
6.5 · 107
8.0 · 102




Fungi
1.7 · 104
<9.9 · 101




Yeast
4.8 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 11

The composition of a formulation to obtain an aqueous solution with surfactants, is (in g):



















Sodium lauryl sulfate (sol. 27%)
12.00




Cocamidopropyl betaine
5.00




Disodium cocoamfoacetate
5.00




Polyquaternium11
1.00




Lactic acid
0.25




Sodium chloride
0.50




Aqua
100
c.s.p.










This formulation is applied in shampoos cosmetic formulations.


This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 12.













TABLE 12








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
3.7 · 106
3.3 · 106




Fungi
7.6 · 104
9.6 · 104




Yeast
3.2 · 104
4.2 · 104



7 days
Aerobes
5.9 · 106
4.8 · 103




Fungi
9.6 · 102
1.1 · 102




Yeast
4.9 · 103
1.2 · 102



14 days
Aerobes
6.3 · 106
7.0 · 102




Fungi
1.1 · 103
<9.9 · 101




Yeast
5.2 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 12

The composition of a formulation to obtain an oil-in-water emulsion with non-ionic surfactants, is (in g):



















Glyceryl stearate + PEG 100 stearate
4.00




Cetyl alcohol + sodium cetyl sulfate
2.00




Caprylic-caproic triglycerides
4.00




Isopropyl mirystate
2.50




Paraffinum
2.00




Dimethicone
0.50




Glycerin
3.00




Wheat (triticum vulgare) germ protein
2.00




Aqua
100
c.s.p.










This formulation is applied in a face cream for skin care.


This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 13.













TABLE 13








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
3.3 · 106
1.1 · 106




Fungi
1.6 · 104
1.7 · 104




Yeast
2.2 · 104
3.2 · 104



7 days
Aerobes
4.3 · 106
3.7 · 104




Fungi
1.9 · 102
8.7 · 102




Yeast
2.5 · 102
9.2 · 102



14 days
Aerobes
4.3 · 106
1.9 · 103




Fungi
1.8 · 102
<9.9 · 101




Yeast
2.9 · 102
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 13

The composition of a formulation to obtain an oil-in-water emulsion with non-ionic surfactants, is (in g):



















Polysorbate 60
3.00




Sorbitan stearate
2.00




Cetyl alcohol
2.50




Paraffinum
2.00




Caprylic-caproic triglycerides
2.00




Ethyl hexyl methoxycinnamate
5.00




Benzophenone 3
1.00




Dimethicone
0.50




Propylene glycol
3.00




Aqua
100
c.s.p.










This formulation is applied in a sun protector cosmetic formulator.


This formulation is completed with 0.20 g of LAE and its capacity of preservation is evaluated against the formulation without LAE. The results are shown in the Table 14.













TABLE 14








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
4.4 · 106
3.1 · 106




Fungi
5.7 · 104
4.9 · 104




Yeast
2.7 · 104
3.8 · 104



7 days
Aerobes
6.3 · 106
8.4 · 103




Fungi
5.1 · 102
2.7 · 102




Yeast
2.3 · 102
4.2 · 102



14 days
Aerobes
7.2 · 106
7.5 · 102




Fungi
5.9 · 102
<9.9 · 101




Yeast
2.8 · 102
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 14

The composition of a formulation to obtain an oil-in-water emulsion with non-ionic surfactants is (in g):



















Cetyl Dimethicone copolyol
3.00




Isohexadecane
4.00




Paraffinum
5.00




Isopropyl myristate
3.00




Caprylic-caproic triglycerides
3.00




Ethyl hexyl methoxycinnamate
5.00




Benzophenone 3
1.00




Glycerin
3.00




Sodium chloride
0.50




Aqua
100
c.s.p.










This formulation is applied in a sun protector cosmetic product.


This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 15.













TABLE 15








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
2.8 · 106
1.4 · 106




Fungi
5.5 · 104
5.3 · 104




Yeast
7.7 · 104
7.9 · 104



7 days
Aerobes
4.4 · 106
9.4 · 102




Fungi
8.6 · 102
6.7 · 102




Yeast
8.3 · 102
4.5 · 102



14 days
Aerobes
7.2 · 106
8.7 · 102




Fungi
5.8 · 102
<9.9 · 101




Yeast
7.9 · 102
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.


Example 15

The composition of a formulation to obtain an emulsion for hands care, is (in g):



















Cetyl alcohol + ceteareth 20
6.00




Isopropyl myristate
2.00




Caprylic-caproic triglycerides
1.00




Dimethicone
1.00




Benzophenone 3
1.00




Glycerin
6.00




Carbomer 940
0.10




Triethanolamine
0.10




Aqua
100
c.s.p.










This formulation is completed with 0.20 g of LAE, and the preservative capacity is evaluated and it is compared with the formulation without LAE. The results are shown in the Table 16.













TABLE 16








Without LAE
With LAE




Microorganism
(cfu/mL)
(cfu/mL)








Initial
Aerobes
4.5 · 106
4.4 · 106




Fungi
6.1 · 104
5.8 · 104




Yeast
8.8 · 104
8.6 · 104



7 days
Aerobes
7.4 · 106
3.3 · 103




Fungi
7.8 · 102
8.7 · 102




Yeast
8.9 · 102
7.2 · 102



14 days
Aerobes
4.4 · 106
<9.9 · 101




Fungi
9.8 · 102
<9.9 · 101




Yeast
1.2 · 103
<9.9 · 101









At 28 days no increase has been detected from the 14 days' count.

Claims
  • 1. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 2. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 3. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 4. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 5. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 6. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of an oil-in-water emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
  • 7. A cosmetic or dermatological composition comprising: (a) a cosmetic or dermatological preparation in the form of a water-in-oil emulsion; and (b) a preservative comprising the cationic surfactant ethyl ester of the lauramide of arginine hydrochloride (LAE), the composition having the following formulation (in g):
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP01/09198 8/9/2001 WO 00 1/16/2004
Publishing Document Publishing Date Country Kind
WO03/013453 2/20/2003 WO A
US Referenced Citations (18)
Number Name Date Kind
3825560 Saito et al. Jul 1974 A
4389489 Preiss et al. Jun 1983 A
5093133 Wisniewski et al. Mar 1992 A
5336515 Murphy et al. Aug 1994 A
5661149 King et al. Aug 1997 A
5681802 Fujiwara et al. Oct 1997 A
5780658 Martinez-Pardo et al. Jul 1998 A
6068867 Nussinovitch et al. May 2000 A
6238654 Tournilhac et al. May 2001 B1
6299915 Nussinovitch et al. Oct 2001 B1
7074447 Bonaventura et al. Jul 2006 B2
7758851 Urgell Beltran et al. Jul 2010 B2
20030049305 Von Rymon Lipinski et al. Mar 2003 A1
20040166082 Urgell-Beltran et al. Aug 2004 A1
20040175350 Urgell Beltran et al. Sep 2004 A1
20040265443 Beltran et al. Dec 2004 A1
20050175747 Seguer Bonaventura et al. Aug 2005 A1
20060003421 Markussen et al. Jan 2006 A1
Foreign Referenced Citations (18)
Number Date Country
0 485 616 May 1992 EP
0 500 332 Aug 1992 EP
0 749 960 Dec 1996 EP
EP0749960 Dec 1996 ES
1 352 420 May 1974 GB
58-039651 Mar 1983 JP
59164704 Sep 1984 JP
03291211 Dec 1991 JP
09188605 Jul 1997 JP
09-255518 Sep 1997 JP
09286712 Nov 1997 JP
10045557 Feb 1998 JP
9407377 Apr 1994 WO
9419026 Sep 1994 WO
9419027 Sep 1994 WO
9621642 Jul 1996 WO
9730964 Aug 1997 WO
0149121 Jul 2001 WO
Non-Patent Literature Citations (17)
Entry
Chemical Abstracts No. 117:114020; New Lipoproteic Surfactants;(1991).
Chemical Abstracts No. 107:79974; Cationic Surfactants with Antimicrobial Activity; (1985).
Chemical Abstracts No. 103:179968; A Comparative Study on Surface-Active and Antimicrobila Properties of Some N.alpha-lauroyl-L-alpha, omega-dibasic amino acid derivatives (1985).
Chemical Abstracts No. 99:122920; N.alpha-acyl-L-alkylaminoguanidinic acids and their salts as surfactants with antimicrobial action (1983).
Chemical Abstracts Service, Columbus, Ohio, US; Garcia Dominguez, J. et al.: “Cationic Surfactants With Antimicrobial Activity” retrieved from STN Database Accession No. 107:79974, XP002196810, Abstract and ES 530 051 A (Consejo Superior De Investigaciones Cientificas, Spain) May 1, 1995.
Chemical Abstracts Service, Columbus, Ohio, US; Garcia Dominguez, J. J. et al.: “N.alpha.-Acyl-L-alkylaminoguanidinic Acids and Their Salts as Surfactants With Antimicrobial Action” retrieved from STN Database Accession No. 99:122920, XP002196912, Abstract and ES 512 643 A (Asociacion De Investigacion De Detergentes, Spain) Feb. 16, 1983.
Infante et al., Surface Active Molecules: Preparation and Properties of Long Chain Nα-Acyl-L-α-Amino-ω-Guanidine Alkyl Acid Derivatives; International Journal of Cosmetic Science 6, 1984, pp. 275-282.
Infante et al., A Comparative Study on Surface Active and Antimicrobial Properties of Some Nα-Lauroyl-Lα, ωDibasic Aminoacids Derivatives; Fette Seifen Anstrichmittel, No. 8, 1985, pp. 309-313.
Garcia Dominguez et al.; Monocapas De Algunos N-α-Acil Aminoacidos Antimicrobianos En Soluciones De NaCl; Anales de Quimica, vol. 82, 1986, pp. 413-418, English Abstract Only.
Infante et al.; The Influence of Steric Configuration of Some Nα-Lauroyl Amino-Acid Derivatives on Their Antimicrobial Activity; Fette Seifen Anstrichmittel, 88, No. 3, 1986, pp. 108-110.
Molinero et al.; Synthesis and Properties of Nα-Lauroyl-L-Argine Dipeptides From Collagen; JAOCS, vol. 65, No. 6, 1988, 4 pages.
Vinardell et al.; Comparative Ocular Test of Lipopeptidic Surfactants; International Journal of Cosmetic Science 12, 1990, pp. 13-20.
Kunieda et al.; Reversed Vesicles From Biocompatible Surfactants, Advanced Materials, No. 4, 1992, pp. 291-293.
Infante et al.; Sintesis Y Propiedades De Tensioactivos Cationicos Derivados De Arginina; Anales de Química, vol. 88, 1992, pp. 542-547, English Abstract Only.
Fördedal et al.; Lipoamino Acid Association in the System Nα-Lauroyl-L-Arginine Methyl Ester-1-Pentanol-Water as Studied by Dielectric Spectroscopy; Colloids and Surfaces A: Physiochemical and Engineering Aspects, 79, 1993, pp. 81-88.
Infante et al., Non-Conventional Surfactants From Amino Acids and Glycolipids: Structure, Preparation and Properties; Colloids and Surfaces A: Physicochemical and Engineering Aspects 123-124, 1997, pp. 49-70.
Moran et al.; Chemical Structure/Property Relationship in Single-Chain Arginine Surfactants; Langmuir 2001, 17, pp. 5071-5075.
Related Publications (1)
Number Date Country
20040175350 A1 Sep 2004 US