CA1147262A - Hydroxyalkylated alkylene diamine in acid beauty aid composition - Google Patents

Hydroxyalkylated alkylene diamine in acid beauty aid composition

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Publication number
CA1147262A
CA1147262A CA000376010A CA376010A CA1147262A CA 1147262 A CA1147262 A CA 1147262A CA 000376010 A CA000376010 A CA 000376010A CA 376010 A CA376010 A CA 376010A CA 1147262 A CA1147262 A CA 1147262A
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Canada
Prior art keywords
health
acid
beauty aid
aid composition
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000376010A
Other languages
French (fr)
Inventor
Irving R. Schmolka
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.)
BASF Corp
Original Assignee
BASF Wyandotte Corp
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Publication date
Application filed by BASF Wyandotte Corp filed Critical BASF Wyandotte Corp
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Abstract

HEALTH AND BEAUTY AID COMPOSITIONS
Abstract of the Disclosure This invention relates to health and beauty aid compositions containing an acid and a neutralizing compound. It has been found that certain totally hydroxy-alkylated alkylene diamines can be used as neutralizing compounds. The compositions are free of detectable nitros-amines.

Description

This invention relates to health and beauty aid compositions. The invention is specifically concerned with compositions which contain an acid and certain totally hydroxyalkylated alkylene diamines.
It is known that many health and beauty aid compositions contain an acid in addition to other ingredients. The acid in such compositions must be neutralized in order to prevent irritation to the skin.
Alkanolamines, such as triethanolamine, diethanolamine, and monoethanolamine, are used commercially to neutralize the acids contained in health and beauty aid compositions.
The problem with using these alkanolamines is that they promote the formation of nitrosamines which are believed to be carcinogenic. Several references are concerned with this topic: M.L. Douglas et al, The Chemistry of Nitrosamine Formation, Inhibition, and Destruction, Journal of the Society of Cosmetic Chemistry (September, 1978) V. 29, p. 581-605; and the Food and Drug /

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, ,, ,~

~1~7'~62 Administration Notice entitled "Industry Called to Act on Nitrosamine Contaminated Cosmetics" published at 44 Federal Register 21365 (April 10, 1g79).

It has been discovered that health and beauty aid compositions can be neutralized by adding certain totally hydroxyalkylated alkylene diamines to formulations which contain an acid. By using such compounds to neutralize the acid, health and beauty aid compositions can be prepared which are free of detectable nitrosamines. These compounds can be added to the formulation without destroying other valuable properties of the composition.
The preferred totally hydroxyalkylated alkylene diamine is N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene-diamine. Although this compound is old and described in U.S. Patent 2,697,118, the patent does not suggest its use in health and beauty aid compositions.

.. ~ . .
For purposes of this invention, a health or beauty aid composition is defined as a composition which, either alone or in combination with other compositions, is applied to the human body. Cosmetic, toiletry, and pharmaceutical preparations are intended to be covered by this defini-tion. Specific examples of these compositions are listed in Kirk-Othmer, EncycloPedia of Chemical Technology (Thira edition, John Wiley and Sons, 1979) Vol. 7, p. 144-146. As this reference shows, there are dozens of various types of ~7~6;~

health and beauty aid compositions. The specific formula-tions for these compositions will depend upon the function of the composition. Several references recite specific formulations for various types of preparations. See, for instance, M. S. Balsam et al, Cosmetics, Science and Technology (Wiley-Interscience, New York, 1972) Volumes 1 and 2.
An essential ingredient of the health and beauty aid preparations of this invention is an acid. For purposes of this invention, an acid is defined as a substance that gives up a proton, or a substance which accepts an electron pair to form a covalent bond. Representative examples of acids which may be used in the compositions of this inven-tion are oleic, linoleic, lauric, myristic, behenic, stearic, palmitic, isostearic, and other similar fatty acids which are nor~ally used in cosmetic and toiletry products.
Also included are dicarboxylic acids such as the C21 acid known as Westvaco diacid, as well as azelaic and sebacic acids. Citric, lactic, and other hydroxy organic acids, such as 12-hydroxystearic acid are included, as well as the sulfuric or phosphoric acid esters of lauryl, myristyl, or similar fatty alcohols, and also sulfated or phosphated ethylene oxide adducts of lauryl and other Eatty alcohols.
Furtner included are organic sulfonic or sulfinic acids such as mono-, di-, and trialkylbenzene or naphthalene sulfonic acid, in which the alkyl groups may vary from one carbon atom (methyl) to 15 carbon atoms (pentadecyl) and can be ~7'~62 branched or straight-chain, as well as alkyl-substituted diphenylether sulfonic acids, such as DOWFAX, and iso--L-olefin sulfonic acids, in which the ~-olefin varies from hexene-1 to octadecene-1 in chain length. Those skilled in the art will understand that the foregoing enumeration is to be considered as illustrative, and not in a limiting sense.
The other essential ingredient in the health and beauty aid compositions of this invention is a totally hydroxyalkylated diamine. Preferably used in this regard is N,N,N',N'-tetrakis(2-hydroxypropyl)ethy~enediamine.
However, other suitable compounds are totally hydroxyoxy-alkylated diamines having from 2 to 6 carbon atoms in the alkylene chain and 2 to 4 carbon atoms in the hydroxyalkyl chain. The N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene-diamine is added in an amount such that the pH of the composition is between 5.5 and 8Ø
In addition to the acid and the totally hydroxy-alkylated diamine, the health and beauty aid compositions of this invention will usually contain one or more active
2~ ingredients. The active ingredients used in accordance with this invention will depend upon the function of the composi-tion. An active ingredient is that ingredient which enables the health or beauty aid preparation to perform its func-tions.
In Example 2 of the Examples which follow, the active ingredient is p-aminobenzoic acid. Without this ingredient, the composition of Example 2 could not function 7~6Z

as a sun screen lotion. In some cases, the active ingredient may be an acid. For instance, in Example 4 of the Examples which follow, the active ingredient is stearic acid. In some cases, the active ingredient may be the salt of an acid and the totally hydroxyalkylated alkylene diamine. This is the case in Examples 10-15 which follow.
A complete listing of active ingredients would be impossible and is unnecessary. Those of ordinary skill in the art are familiar with the types and amounts of active ingredients which are used in preparing health and beauty aid compositions. References such as Cosmetics, Science and Technology, referred to previously, describe specific formulations with various active ingredients. The par-ticular active ingredient is not critical to the present invention.
In addition to an acid, a totally hydroxyalkylated alkylene diamine, and an active ingredient, the compositions of this invention may also contain a carrier such as water, a solvent such as an alcohol, anionic, cationic, and nonionic surfactants, preservatives, perfumes, colorants, and various other ingredients. Nothing further need be said about these-ingredients. Those of skill in the art are familiar with these ingredients. Their use is described in many of the formulations given in Cosmetics, Science and Technology which was referred to previously.
The amount of totally hydroxyalkylated alkylene diamine to be used in the compositions of this invention 7~62 will depend upon the nature and amount of the acid in the composition. However, the amount should be sufficient to raise the pH of the composition to between 5.5 and 8Ø
Given the information in this specification and the Examples which follow, those of ordinary skill in the art will be able to make effective compositions which contain an acid and a totally hydroxyalkylated alkylene diamine. The Examples which follow are intended to illus-trate the practice of this invention, but are not intended to limit its application. The parts given in the Examples are by weight unless otherwise specified. Some of the trade names have been used for the ingredients in the Examples.
technical description of these ingredients is given in the list which follows the Examples.

~7~6~

Example 1 Shampoo QUADROL 8.0 Lauryl Ether Sulfuric Acid Ester 24.0 Water 68.0 100 .0 Example 2 Sun Screen Lotion VE~GU~ 1.5 Water 77.5 QUADROL 5.0 MYVACET 9-40 4.0 Cetyl Alcohol 0.5 Stearic Acid 1.5 Cocoyl Sarcosine5.0 p-Aminobenzoic Acid 5.0 Preservative q.s.
100 .0 ~ ~7Z6Z

Example 3 Hair Dressing CARBOPOL 934 0.5 Water 19.8 QUADROL 0.7 Water 35.0 AMERCHOL L 101 5.0 Isopropyl Lanolate 1.0 ~EG 40 Stearate 3.0 PPG 33 Butyl Ether 15.0 PPG 12 BUTETH 16 5.0 ~ineral Oil 15.0 Preservative q.s Perfume q.s 100 .0 ~7~62 Example 4 Brushless Shave Cream Stearic Acid18.0 Mineral Oil 5.0 Polysorbate 605.0 Sorbitol 5.0 Borax 2.0 QUADROL 1.5 Water 63.5 Preservative q.s Perfume q.s 100.0 ~7~6Z

Example 5 Moisturizing Cream VEEGUM 1 . O
Water 72.5 Glycerine 4.0 QUADROL 1.5 POLYPEPTIDE SF5.0 Lanolin Oil 10.0 Stearic Acid 2.0 Isopropyl Myristate 2.0 Cetyl Alcohol 2.0 Perfume q.s Preservative q.s 100 .0 Example 6 Baby Cream Olive Oil 10.0 Stearic Acid 4.0 Lanolin 3.0 ~lyceryl Stearate12.0 ~Sorbitol 5.0 QUADROL 1.5 Water 64.5 Preservative q.s 100 .0 ~7'~6Z

Example 7 Shampoo QUADROL 3.5 Alpha-Olefin Sulfonate Sodium Salt (35%) 52.0 Oleic Acid 7.0 Lauric Diethanolamide 2.0 ~ater 35.5 100.0 Example 8 Face and Hand Cleaner Lotion VEEGUM 2.5 Water 65.5 QUA~ROL 3.5 Propylene Glycol 5.0 CAPTAN 0.2 Citric Acid 0.3 Stearic Acid 4.0 Cocoyl Sarcosine 6.0 Cetyl Alcohol 1.0 Glyceryl Monostearate 3.0 ~ineral Oil 5.0 Lanolin Oil 4~0 100 .0 7Z6;2 Example 9 Barrier Cream Mineral Spirits 15.0 Mineral Oil 15.~
Water 42.5 PLURO~IC 25R5 6.0 Stearic Acid 7.5 Silicone Fluid (350 centistokes) 2.0 Cetyl Alcohol 2.2 QUADROL 4.8 Propylene Glycol 5.0 Preservative q.s.
100 .0 Example 10 Cream Lotion Shampoo Glyceryl Monostearate 3.0 Carbomer 934 1.0 QUADROL 1.5 Salt of QUADROL and dodecyl benzene sulfonic acid (60%) 33.0 Water 61.5 Perfume q.s Preservative q.s 100 .0 _ 1 ;,~_ ~7'~6~, Example 11 Shampoo Salt of QUADROL and Lauraminodipropionic Acid 6.0 Lauraminopropionic Acid 3.0 QUADROL-neutralized Lauryl Sulfate 6.0 Ethoxylated Lanolin 6.0 Lauric Isopropanolamide 4.0 Water 75.0 100 .0 ~xample 12 Shampoo Salt of QUADROL and Cocyl Sarcosine 10.0 Salt of ~UADROL and Lauryl Ether Sulfuric Acid ~.0 Lauric Isopropanolamide 3.0 Lauric Diethanolamide 3.0 Ethylenediamine Tetracetic Acid 0O65 Ethyl Alcohol 7.0 Methyl Cellulose 0.75 Water 71.6 Preservative q.s.
Perfume q.s.
100.0 ~7Z62 Example 1 3 Shampoo Salt of QUA~ROL and Lauryl Ether (3EO) Sulfuric Acid (60% active) 30.0 Sodium Chloride 2.9 Water 67.0 Sodium Nitrite 0.1 100 .0 Example 14 Shampoo Salt of QUADROL and Lauryl Sulfuric Acid (40% active) 60.0 MONAMID 150 ADD 5.0 AMMONYX LO 1.0 Water 30 . 9 BRONOPOL 0.1 100 .0 ~7~62 Example 15 Cream Lotion Shampoo Salt of QUADROL and Dodecyl Benzene Sulfonic Acid (67% active) 29.6 Glyceryl Monostearate 3.0 Carbomer 934 1.0 QUADROL 3.5 Water 62.8 Sodium Nitrite 0.1 1 0 0 . O

Examples 1-15 illustrate that it is possible to prepare a variety of health and beauty aid compositions which contain an acidic substance which has been neutralized by N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine without adversely affecting the cosmetic properties of the compositions.
Comparative Example The purpose of this Example is to show the effect, relative to nitrosamine formation, of using Q~ADROL instead of triethanolamine. In order to illustrate the effect, two shampoos were prepared. Formulation A contained the following ingredients:

7Z~2 Salt of Triethanolamine and Lauryl Sulfuric Acid (40% Activej 60 Lauramine Oxide 10 Laneth 16 3 Water 75 Formulation B contained the following ingredients:

Salt of QUADROL and Lauryl Sulfuric Acid (40~ Active) 60 Lauramine Oxide 10 Laneth 16 3 Water 27 Formulation A and B were analyzed for nitrosamine content after they had aged for two months~ The results of the analysis showed that formulation A had 151 ppb of nitrosamines with the limit of detection being 20 ppb.
Formulation B had no nitrosamines with the limit of detec-tion being 100 ppb.
This Comparative Example illustrates the bene-ficial effect of using QUADROL instead of triethanolamine relative to nitrosamine formation.
INGREDIENT SPECIFICATIONS
V~EGUi~ is finely divided magnesium aluminum silicate.

~7~62 CAPTAN is CgH8Cl3NO2S , N-trichloromethylmercapto-tetrahydrophthalimide~
QUADROL~ is N,N,N',N'-tetrakis(2-hydroxypropyl)-ethylene diamine and is a trademark of BASF Wyandotte Corporation, Parsippany, N.J.
Laneth 16 is the polyethylene glycol ether of lanolin alcohol with an average ethox-ylation value of 16.
LAURETH -4 is an adduct resulting from the oxyethylation of lauryl alcohol with 4 moles of ethylene oxide.
LAURETH -23 is an adduct resulting from the oxyethylation of lauryl alcohol with 23 moles of ethylene oxide.
MYVACET 9-40 is distilled acetylated mono-glycerides.
Carbomer 934 is a member of a group of water-soluble resins having excellent suspending, thickening and gel-forming properties.
AMERCHOL L 101~ is an emollient comprising a blend of mineral oil and lanolin alcohol ("Amerchol" is a trade-mark of American Cholesteral Products, Inc., Edison, N.J.).
P~G 40 Stearate is the monostearic acid ester of a 40-unit polyoxyethylene glycol.
PPG 33 butyl ether is an adduct of butyl alcohol and 33 units of propylene oxide.
PPG 12 BUTETH 16 is a mixture of 12 moles of propylene oxide and 16 moles of ethylene oxide, condensed with butyl alcohol.

7~62 POLYSORBAT~ 6U is polyoxyethylene (~0) sorbitan monostearate.
POLYPEPTIDE SF is a hydrolyzed animal protein product and is a trademark of Stepan Chemical Co.
PLURONIC 25~5 is a block polymer of the oxy-propylene-oxyethylene-oxypropylene type disclosed in U.S.
Patent No. 3,036,118, having an average molecular weight of 4500 and a proportion of the molecular weight attributable to the oxypropylene hydrophobe cf approximately 50 percent.
MONAMID 150 ADD is a surface-active agent ("Monamid" is a trademark of ~ona Industries, Inc., Paterson, New Jersey).
AMMONYX LO is lauryl dimethyl amine oxide ("Ammonyx" is a trademark of Onyx Chemical Co., Jersey City, New Jersey).
SOLULAN 16 is a 16-mole ethylene oxide adduct of lanolin alconol ("Solulan" is a trademark of American Cholesterol Products, Inc., Edison, N.J.).
BRONOPOL is 2-bromo-2-nitropropane-1,3-diol.

Claims (15)

The embodiments of the invention in which an exclusive privilege or property is claimed are defined as follows:
1. A health or beauty aid composition comprising (a) an acid, and (b) a totally hydroxyalkylated alkylene diamine in an amount such that the pH of the composition is between 5.5 and 8Ø
2. The health or beauty aid composition of claim 1 containing an active ingredient as an additional ingredient.
3. The health or beauty aid composition of claim 1 containing a carrier as an additional ingredient.
4. The health or beauty aid composition of claim 2 containing a carrier as an additional ingredient.
5. The health or beauty aid composition of claim 1, wherein the totally hydroxyalkylated alkylene diamine is N,N,N',N'-tetrakis(2-hydroxypropyl)-ethylene-diamine.
6. An acid-containing health or beauty aid composition comprising a health or beauty aid formulation having incorporated therein, as a neutralizing compound, a totally hydroxyalkylated alkylene diamine in amount such that the pH of the formulation is between 5.5 and 8Ø
7. The health and beauty aid composition of claim 6 wherein the totally hydroxyalkylated alkylene diamine is N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene-diamine.
8. In a health and beauty aid composition comprising an acid and a neutralizing compound, the improve-ment which comprises using a totally hydroxyalkylated alkylene diamine as the neutralizing compound in an amount such that the pH of the composition is between 5.5 and 8Ø
9. The health and beauty aid composition of claim 8 wherein the neutralizing compound is N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine.
10. A process for neutralizing an acid containing health or beauty aid formulation comprising adding a totally hydroxyalkylated alkylene diamine to said formulation in an amount such that the pH of the formulation is between 5.5 and 8Ø
11. The process of claim 10 wherein the totally hydroxyalkylated ethylene diamine is N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine.
12. In a process for preparing a health or beauty aid composition comprising combining an acid and a neutral-izing agent, the improvement which comprises using a totally hydroxyalkylated alkylene diamine as the neutralizing compound in an amount such that the pH of the composition is between 5.5 and 8Ø
13. The process of claim 12 wherein the totally hydroxyalkylated alkylene diamine is N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine.
14. In a process for preparing a health or beauty aid composition comprising combining an acid, a neutralizing compound, a carrier, and an active ingredient, the improve-ment which comprises using a totally hydroxyalkylated alkylene diamine as the neutralizing compound in amount such that the pH of the composition is between 5.5 and 8Ø
15. The process of claim 14 wherein the neutral-izing compound is N,N,N',N'-tetrakis(2-hydroxypropyl)-ethylenediamine.
CA000376010A 1980-12-02 1981-04-23 Hydroxyalkylated alkylene diamine in acid beauty aid composition Expired CA1147262A (en)

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US212,171 1980-12-02

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556509A (en) * 1984-10-09 1985-12-03 Colgate-Palmolive Company Light duty detergents containing an organic diamine diacid salt
US4778825A (en) * 1986-08-29 1988-10-18 The University Of Akron Macrophage stimulation by quadrol
WO2018005261A1 (en) * 2016-06-30 2018-01-04 The Procter & Gamble Company Conditioner composition comprising a chelant
WO2018005256A1 (en) * 2016-06-30 2018-01-04 The Procter & Gamble Company Shampoo compositions comprising a chelant
US11246816B2 (en) 2016-06-30 2022-02-15 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11458085B2 (en) 2016-06-30 2022-10-04 The Procter And Gamble Company Hair care compositions for calcium chelation
US11786447B2 (en) 2016-06-30 2023-10-17 The Procter & Gamble Company Conditioner composition comprising a chelant

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556509A (en) * 1984-10-09 1985-12-03 Colgate-Palmolive Company Light duty detergents containing an organic diamine diacid salt
US4778825A (en) * 1986-08-29 1988-10-18 The University Of Akron Macrophage stimulation by quadrol
WO2018005261A1 (en) * 2016-06-30 2018-01-04 The Procter & Gamble Company Conditioner composition comprising a chelant
WO2018005256A1 (en) * 2016-06-30 2018-01-04 The Procter & Gamble Company Shampoo compositions comprising a chelant
CN109310603A (en) * 2016-06-30 2019-02-05 宝洁公司 Shampoo Compositions comprising chelating agent
US10973744B2 (en) 2016-06-30 2021-04-13 The Procter And Gamble Company Conditioner composition comprising a chelant
US11166894B2 (en) 2016-06-30 2021-11-09 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11246816B2 (en) 2016-06-30 2022-02-15 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11458085B2 (en) 2016-06-30 2022-10-04 The Procter And Gamble Company Hair care compositions for calcium chelation
US11786447B2 (en) 2016-06-30 2023-10-17 The Procter & Gamble Company Conditioner composition comprising a chelant

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