US3846554A - Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation - Google Patents

Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation Download PDF

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Publication number
US3846554A
US3846554A US00315285A US31528572A US3846554A US 3846554 A US3846554 A US 3846554A US 00315285 A US00315285 A US 00315285A US 31528572 A US31528572 A US 31528572A US 3846554 A US3846554 A US 3846554A
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United States
Prior art keywords
detergent
detergent composition
acid
skin
dicarboxylic acid
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Expired - Lifetime
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US00315285A
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English (en)
Inventor
W Rieder
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Milacron Inc
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Milacron Inc
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Filing date
Publication date
Application filed by Milacron Inc filed Critical Milacron Inc
Priority to US00315285A priority Critical patent/US3846554A/en
Priority to CA183,150A priority patent/CA983803A/en
Priority to FR7343031A priority patent/FR2210661B1/fr
Priority to GB5626773A priority patent/GB1445590A/en
Priority to JP48138245A priority patent/JPS5139965B2/ja
Priority to NL7317196A priority patent/NL167990C/xx
Priority to DE19732362268 priority patent/DE2362268C3/de
Application granted granted Critical
Publication of US3846554A publication Critical patent/US3846554A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring

Definitions

  • ABSTRACT Reduction of skin irritation caused by skin irritating detergent or detergent composition is achieved by incorporating in the irritating detergent or detergent composition'an effective amount of a protective agent of the formula where R is the carboxyl free residue of an aromatic, cycloaliphatic or aralkyl di-, trior tetra-carboxylic acid or the carboxyl free residue of the unsaturated polycarboxylic acid product of the polymerization of two to four molecules of a monomeric ethylenically unsaturated C to C fatty acid or the hydrogenated derivative of said unsaturated polycarboxylic acid product;
  • R is hydrogen, hydroxyl, C C -alkyl, or C -C alkyl substituted with hydroxyl or amino;
  • R" and R are hydrogen or C C -a1kyl
  • n 0, 1 or 2;
  • X is oxygen or nitrogen
  • M is H or a cation
  • q is 0 when X is oxygen and q is 1 when X is nitrogen.
  • the present invention relates to protective agents which prevent or reduce skin irritation, particularly to improved detergent compositions which exhibit reduced skin irritation by virtue of the presence of such protective agents, and to methods for preventing or reducing skin irritation resulting from contact with irritating detergent compositions.
  • an object of the present invention to prevent or reduce skin irritation resulting from contact of the skin with chemical compositions, particularly detergent compositions.
  • a protective agent having the formula L N n where R is the carboxyl free residue of an aromatic, cycloaliphatic or aralkyl di-, tri, or tetra-carboxylic acid or the carboxyl free residue of the unsaturated polycarboxylic acid product of the polymerization of two to four molecules of a monomeric ethylenically unsaturated C to C fatty acid or the hydrogenated derivative of said unsaturated polycarboxylic acid product; R is hydrogen, hydroxyl, C -C alkyl or C C -alkyl substituted with hydroxyl or amino;
  • R" and R' are hydrogen or C -C alkyl
  • n 0, l or 2;
  • M is H or a cation
  • X is oxygen or nitrogen
  • q is 0 when X is oxygen and q is 1 when X is nitrogen.
  • the protective agent should be soluble or colloidally dispersible in an aqueous phase, compatible with the detergent or detergent composition and stable in aqueous media.
  • dispersible is meant to define colloidal dispersibility of the protective agent in concentrations in which the protective agent is employed in actual use.
  • a cyclic structure in the protec tive agent can aid in the adsorption of the protective agent onto the keratin layer of the skin and that the protective agent interacts with the protein molecules of the keratin layer.
  • the protective agents are capable of and do interact with different protein molecules of the skin.
  • the irritation of the skin by the action of a detergent or other irritant is believed to be caused by the penetration of the detergent into the skin, causing separation and/or degradation of the protein molecules of the keratin layer, thereby exposing the living cells of the skin to the detergent and, more significantly, exposing these cells to other more irritating compounds associated with the detergent.
  • the damage to the cells caused by the contact is believed to result in irritation, inflammation, and dermatitis.
  • the protective agents employed in the detergent compositions of the present invention are believed to counteract this breakdown by providing additional bridges between the protein molecules of the-keratin layer, which maintain the integrity of the skin surface thereby preventing the penetration of 'the detergent molecules through the keratin layer into the living tissue. It is to be understood, however, that we do not wish to be bound by the foregoing explanation of the activity of the protective agents of the present invention, and that such explanation is only set forth for a better understanding of the present invention.
  • the protective agents should be compatible with the detergent and should be of the type capable of existing in the aqueous phase, i.e., without irreversibly reacting with the water.
  • the protective agents of this invention can be obtained by methods of synthesis known in the art, such as are disclosed in US. Pat. No. 2,889,334 and U.S. Pat. No. 2,987,522, and U.S. Pat. No. 3,251,852, the
  • Such methods may involve the reaction of a polycarboxylic acid with a 1,2-diamino alkane, a lhydroxy-2-amino alkane, a l amino-2-hydroxy alkane, an N-mono-substituted l,2-diamino alkane, 01,8 alkanol amine and an aliphatic a,,B-diamine.
  • the acid halide e.g. acid chloride, maybe used.
  • polycarboxylic acids which may be used in the preparation of the protective agents of this invention there are included phthalic acid, isophthalic acid, terephthalic acid, trimesic acid, l,4-cyclohexane dicarboxylic acid, l,3-cyclohexane dicarboxylic acid, l,2- cyclohexane dicarboxylic acid, l,4-cyclohex 2-ene dicarboxylic acid, l,4-cyclohex--ene dicarboxylic acid, l,4-cyclohex-1-ene dicarboxylic acid, 1,4-cyclohex- 3-ene dicarboxylic acid, 1,3-cyclohex-2-ene dicarboxylic acid, l,3-cyclohex-3-ene dicarboxylic acid, l,3- cyclo-hex-5-ene dicarboxylic acid, l,2,4-cyclohexan
  • the starting materials comprising polymerized unsaturated polycarboxylic acids are obtained by polymerizing two to four molecules of ethylenically unsaturated C to C fatty acid to give products containing two to four carboxyl groups comprising the dimer, trimer, tetramer or mixtures thereof, possibly containing some of the starting fatty acid in unpolymerized form.
  • the starting ethylenically unsaturated acid can be monoor polyunsaturated.
  • Preferred unsaturated polycarboxylic acid products are obtained from linoleic acid.
  • Typical of the commercially available unsaturated polycarboxylic acid products useful in this invention are Empol Dimer Acids marketed by Emery Industries Inc.
  • Literature supplied by Emery Industries Inc. indicates that reactions at the carboxyl group of Empol Dimer Acids aretypical of aliphatic carboxylic acids. Indeed, this has been found to be true.
  • the conversion of the carboxyl group to the other groups mentioned herein is analogous to conversions used to prepare the corresponding derivatives of other carboxylic acids.
  • Examples of l,2-diamino alkanes include ethylene diamine, l,2-butane diamine, 1,2-propane diamine, l,2-pentane diamine and 1,2-hexanediamine.
  • Examples of l-hydroxy-2-amino alkanes include 1- hydroxy-2-amino propane, ethanol amine, l-hydroxy- 2-amino butane, l-hydroxy-Z-amino pentane and lhydroxy-2-amino hexane.
  • Examples of l-amino-Z-hydroxy alkanes include 1- amino-2-hydroxypropane, 1-amino-2-hydroxy butane, 1-amino-2-hydroxy pentane, and 1-amino-2-hydroxy hexane.
  • N-mono substituted 1,2-diamino alkanes examples include N-methyl ethylene diamine, N-ethyl ethylene diamine, N-propyl ethylene diamine, N-butyl ethylene diamine, hydroxy ethyl ethylene diamine, hy-
  • the protective agents of this invention include but i are not limited to oiii-crr orrromoifor CH- H II! II Continued W I1I-CHR [D]( J H2 L ⁇ N 2 14 H2o( OOH2 H20 o-Q-h JJH:
  • [D] is the carboxyl free residue of dimerized linoleic acid and R" is CH2, CH2CH3 or CH2CH2CH3.
  • [D] is the carboxyl free residue of dimarized linoleic acid and R and R are -CHs, OHzCHa or CHzCHzCHa.
  • [T] is the carboxyl free residue of trimerized linoleic acid.
  • R is H, CH3, CH2CH3, CH2CH2OH, or CH2OH2NH2; and M is H, Na, K or the triethanolamine cation.
  • [D] is the carboxyl free residue of dimerized linoleic acid
  • M is H, N a, K or the triethanolamine cation.
  • [T] is the carboxyl free residue of trimerized linoleic acid
  • M is H, Na, K or the triethanolamine cation.
  • the protective agents described herein above can be employed in combination with any detergent that is anionic, cationic, nonionic or amphoteric in nature. It will be apparent, however, that the protective agent should be compatible with the detergent to avoid precipitation of both detergent and agent. The reduction of skin irritation will be observable in all compatible combinations, although the extent of the anti-irritant effect will differ with the various protective agents discussed, as well as with the detergent. Since some of the detergents, particularly nonionic detergents, areby themselves relatively nonirritating, the described protective agent is less useful, although the protective effect of the agent can be established when such detergents, which at normally used concentrations cause little or no skin irritation, are tested at high concentrations and/or longer periods of contact with the skin.
  • the anti-irritation effect of the protective agent is exhibited over a wide range of proportions of agent to detergent (e.g. 0.00521 to 10:1 by weight) as indicated above. However, optimum results are generally obtained when the ratio of detergent to protective agent is in the range of 3:1 to 1:3 by weight.
  • detergent C non-soap anionic detergents with which the described protective agents are suitably employed include alkyl sulfates, alkyl sulfonates, alkyl benzene sulfonates, alkyl phenyl polyoxyalkylene sulfonates, alkyl glyceryl ether sulfonates, alkyl monoglyceride sulfates, alkyl monoglyceride sulfonates, alkyl polyoxyethylene ether sulfates, acyl sarcosinates, acyl esters of isothionates, acyl-N-methyl taurides, dialkyl esters of sulfosuccinic acid, and mixtures thereof.
  • the alkyl or acyl radicals contain from nine to 20 carbon atoms.
  • these detergents are employed in the form of sodium, potassium, ammonium, and alkylolammonium salts, as well as similar water-soluble salts.
  • Specific examples include sodium lauryl sulfate, potassium-N-methyl lauroyl tauride, triethanol ammonium dodecyl sulfonate, potassium polyoxypropylene benzene sulfonate, sodium lauryl sulfonate, dioctyl ester of sodium sulfosuccinic acid, sodium salt of lauryl polyoxyethylene sulfate, and sodium salt of tridecylether polyoxyethylene sulfate.
  • the cationic detergents which can be reduced in their skin irritation by the addition of the protective agents of the present invention include, in particular, quaternary ammonium salts which contain at least one alkyl group having 12 to 20 carbon atoms.
  • quaternary ammonium salts which contain at least one alkyl group having 12 to 20 carbon atoms.
  • the halide ions are the mostcommon anions, the anion can be acetate, phosphate, sulfate, nitrite, or the like.
  • Specific cationic detergents include distearyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, stearyl trimethyl ammonium chloride, coco dimethyl benzyl ammonium chloride, dicoco dimethyl ammonium chloride, cetyl pyridinium chloride, cetyl trimethyl ammonium bromide, stearyl amine salts that are soluble in water such as stearyl amine acetate and stearyl amine hydrochloride, stearyl dimethyl amine hydrochloride, distearyl amine hydrochloride, alkyl phenoxyethyoxyethyl dimethyl ammonium chloride, decylpyridinium bromide, pyridinium chloride derivative of the acetyl amino ethyl esters of lauric acid, lauryl trimethyl ammonium chloride, decyl amine acetate, lauryl dimethyl ethyl ammonium chloride
  • Nonionic detergents include, in particular, the alkylene oxide ethers of phenols, fatty alcohols, and alkyl mercaptans, the alkylene oxide esters of fatty acids, the alkylene oxide ethers of fatty acid amides, the condensation products of ethylene oxide with partial fatty acid esters, and mixtures thereof.
  • the polyoxyalkylene chain in such detergents can contain from five to 30 alkylene oxide units in which each alkylene unit has from two to three carbon atoms.
  • nonionic detergents include nonyl phenol polyoxyethylene ether, tridecyl alcohol polyoxyethylene ether, dodecyl mercaptan polyoxyethylene thioether, the lauric ester of polyethylene glycol, the lauric ester of methoxy polyethylene glycol, the lauric ester of sorbitan polyoxyethylene glycol, the lauric ester of sorbitan polyoxyethylene ether, and mixtures thereof.
  • the protective agents of the present invention are particularly effective in reducing the irritationcaused by such anionic detergents as the alkyl sulfates and sulfonates and the alkyl benzene sulfates and sulfonates, and by such cationic detergents as the described fatty alkyl-containing quaternary ammonium compounds.
  • detergents described hereinabove are employed in their commercial application in combination with builders or other additives, depending on the intended commercial utilityof the detergent.
  • the presence of such additives does not affect the ability of the protective agent to counteract the skin irritation caused by the detergent.
  • the skin irritation is caused by the action of the detergent on the skin in causing the keratin of the skin to break down.
  • the detergent itself may not be extremely irritating, it allows other materials employed in combination with the detergent which are highly irritating to come in contact with the living tissue of the skin, even though in the absence of the detergent such materials are non-irritating in not being able to break down the keratin of the skin.
  • the protective agents of the present invention are, therefore, capable of protecting the skin against skin irritation caused by such additives.
  • Builders employed in commerical detergent formulations are generally alkali salts of weak inorganic acids used alone or in admixtures, such as alkali metal, ammonium or substituted ammonium salts of carbonates, borates, phosphates, polyphosphates, bicarbonates, and silicates.
  • alkali metal, ammonium or substituted ammonium salts of carbonates, borates, phosphates, polyphosphates, bicarbonates, and silicates are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium pyrophosphate, sodium bicarbonate, potassium bicarbonate, potassium carbonate, sodium monoand diorthophosphate, sodium metasilicate, and mixtures thereof.
  • the built detergent compositions of the present invention can, furthermore, contain other adjuvants normally employed in detergent compositions such as perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, fabric softeners, oxygen or chlorine bleaches, suids builds, suds debased on a scale of l to 10, in which the numbers have the meanings given in Table 1 below.
  • the inorganic Grade or builders or the combination of the builders and the ad- Rating Gross Reaction Skin Damage juvants described can constitute up to 80% of the built detergent composition, the remainder of the built de- 1 3353533 5 3? bleedmg; 5331;255: tergent composition being the detergent and the proin most instances ⁇ active agent 10 2 lSfleeveedriencracking; moderate do
  • the detergent compositions of the present invention 3 Severe iracking; Slight to Severe include laundry detergents, kitchen detergents, shammoderate bleeding poos, industrial detergents, and the like.
  • the use of the g g jfi fg i z Mgg protective agent of the present invention does not af- 6 Severe scaling do. fect the effective concentrations of the detergent, and 5 7 p Slight hence concentrations of detergents heretofore em- 3 gif lli and moderate Slight ployed are also applicable in the modified compositions edema of the present invention.
  • the yholy (oxyethylene) ethanoh In general the detergent proteehve, agent, a be apphed to the 5km prlor to and the protective agent are each employed in the data Contact wlth. h "m and agamst illustrated below in a concentration of 15 weight persubseque? F' h period of cent based on the described 100 g concentrate.
  • R is hydrogen, hydroxyl, C C -a1kyl, or C -C alkyl substituted with hydroxyl or amine;
  • R and R are hydrogen or C C -alkyl
  • X is oxygen or nitrogen
  • M is H, or a cation
  • n 0, l or 2;
  • n 1,2, 3, or 4;
  • q is 0 when X is oxygen and q is 1 when X is nitrogen; said detergent composition enhibiting reduced skin irritation relative to the said detergent composition absent the protective agent.
  • R is the carboxyl-free residue of a cycloaliphatic dicarboxylic acid selected from the group consisting of cyclohexane dicarboxylic acids, cyclohexene dicarboxylic acids and cyclohexane diacetic acids, wherein the cyclohexene dicarboxylic acid is 1,4-cyclohex 2-ene dicarboxylic' acid, 1,4-cyclohex-5-ene dicarboxylic acid, 1,4-cyclohex-l-ene dicarboxylic acid, 1,4- cyclohex-3-ene dicarboxylic acid, 1,3-cyclohe-x-2-ene dicarboxylic acid, 1,3-cyclohex-3-ene dicarboxylic acid or l,3-cyclohex-5-ene dicarboxylic acid.
  • a cycloaliphatic dicarboxylic acid selected from the group consisting of cyclohexane dicarboxylic
  • R is the carboxyl-free residue of an aralkyl dicarboxylic acid selected from the group consisting of o-benzene diacetic acid, m-benzene diacetic acid and p-benzene diacetic acid.
  • R is the carboxyl free residue of the unsaturated polycarboxylic acid product obtained by the polymerization of two to four molecules of a monomeric ethylenically unsaturated C to C fatty acid.
  • R is the carboxyl free residue of the hydrogenated derivative of the unsaturated polycarboxylic acid obtained by the polymerization of 2 to 4 molecules of a monomeric ethylenically unsaturated C to C fatty acid.
  • composition of claim 13 wherein the detergent composition contains from 10 to percent by weight of the composition of inorganic water soluble detergent builders.
  • n 2;
  • X is nitrogen.
  • n 0;
  • n 2;
  • X is oxygen
  • n 0;
  • n 2;
  • X is oxygen
  • R" and R are hydrogen
  • n 2;
  • X is nitrogen.
  • R" and R' are hydrogen
  • n 0;
  • n 2;
  • X is nitrogen.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
US00315285A 1972-12-15 1972-12-15 Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation Expired - Lifetime US3846554A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US00315285A US3846554A (en) 1972-12-15 1972-12-15 Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation
CA183,150A CA983803A (en) 1972-12-15 1973-10-11 Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation
FR7343031A FR2210661B1 (enrdf_load_html_response) 1972-12-15 1973-12-03
GB5626773A GB1445590A (en) 1972-12-15 1973-12-05 Detergent compositions exhibiting reduced skin irritation
JP48138245A JPS5139965B2 (enrdf_load_html_response) 1972-12-15 1973-12-13
NL7317196A NL167990C (nl) 1972-12-15 1973-12-14 Werkwijze voor het op op zichzelf bekende wijze bereiden van een preparaat dat ten minste een wasactieve stof en ten minste een huidverzachter bevat.
DE19732362268 DE2362268C3 (de) 1972-12-15 1973-12-14 Detergenszusammensetzungen mit einem Gehalt an hautreizenden Detergentien und einem Schutzmittel

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00315285A US3846554A (en) 1972-12-15 1972-12-15 Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation

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US3846554A true US3846554A (en) 1974-11-05

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JP (1) JPS5139965B2 (enrdf_load_html_response)
CA (1) CA983803A (enrdf_load_html_response)
FR (1) FR2210661B1 (enrdf_load_html_response)
GB (1) GB1445590A (enrdf_load_html_response)
NL (1) NL167990C (enrdf_load_html_response)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070212425A1 (en) * 2006-03-09 2007-09-13 Barna Ivan J Cidal formulations and methods of use

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2889332A (en) * 1957-09-17 1959-06-02 Du Pont Process for production of hydantoins
US2987522A (en) * 1958-03-17 1961-06-06 Petrolite Corp Amidine products
CA639398A (en) * 1962-04-03 The Procter And Gamble Company Of Canada Detergent compositions
US3251852A (en) * 1959-06-15 1966-05-17 Petrolite Corp Amino polymers
US3354175A (en) * 1962-04-12 1967-11-21 Merck Ag E 2-(2', 5'-dialkoxybenzyl)-2-imidazolines and related compounds
GB1196028A (en) * 1967-10-12 1970-06-24 Iwao Kawakami Cosmetic Preparations

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA639398A (en) * 1962-04-03 The Procter And Gamble Company Of Canada Detergent compositions
US2889332A (en) * 1957-09-17 1959-06-02 Du Pont Process for production of hydantoins
US2987522A (en) * 1958-03-17 1961-06-06 Petrolite Corp Amidine products
US3251852A (en) * 1959-06-15 1966-05-17 Petrolite Corp Amino polymers
US3354175A (en) * 1962-04-12 1967-11-21 Merck Ag E 2-(2', 5'-dialkoxybenzyl)-2-imidazolines and related compounds
GB1196028A (en) * 1967-10-12 1970-06-24 Iwao Kawakami Cosmetic Preparations

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Japanese Appls. JA67 012518, R18; 1 3 67; JA 12518, 1/3/67; 29199/69; 42425 JA 7017316. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070212425A1 (en) * 2006-03-09 2007-09-13 Barna Ivan J Cidal formulations and methods of use

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Publication number Publication date
GB1445590A (en) 1976-08-11
JPS5139965B2 (enrdf_load_html_response) 1976-10-30
NL167990C (nl) 1982-02-16
NL167990B (nl) 1981-09-16
NL7317196A (enrdf_load_html_response) 1974-06-18
DE2362268A1 (de) 1974-07-04
JPS4989705A (enrdf_load_html_response) 1974-08-27
FR2210661B1 (enrdf_load_html_response) 1977-06-10
DE2362268B2 (de) 1975-12-11
FR2210661A1 (enrdf_load_html_response) 1974-07-12
CA983803A (en) 1976-02-17

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