US3376229A - Synthetic detergent bar - Google Patents

Synthetic detergent bar Download PDF

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Publication number
US3376229A
US3376229A US417801A US41780164A US3376229A US 3376229 A US3376229 A US 3376229A US 417801 A US417801 A US 417801A US 41780164 A US41780164 A US 41780164A US 3376229 A US3376229 A US 3376229A
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United States
Prior art keywords
isethionate
bar
detergent
acid
water
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 - Lifetime
Application number
US417801A
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English (en)
Inventor
Robert A Haas
Lamberti Vincent
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.)
Lever Brothers Co
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Lever Brothers Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lever Brothers Co filed Critical Lever Brothers Co
Priority to US417801A priority Critical patent/US3376229A/en
Priority to CH1677365A priority patent/CH479695A/de
Priority to ES0320479A priority patent/ES320479A1/es
Priority to BE673468A priority patent/BE673468A/xx
Priority to DEU12261A priority patent/DE1277497B/de
Priority to GB52256/65A priority patent/GB1130705A/en
Priority to SE16052/65A priority patent/SE339969B/xx
Priority to AT1111965A priority patent/AT255008B/de
Priority to LU50034A priority patent/LU50034A1/xx
Priority to FR41845A priority patent/FR1460223A/fr
Priority to NL656516149A priority patent/NL148102B/xx
Application granted granted Critical
Publication of US3376229A publication Critical patent/US3376229A/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
    • 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
    • C11D1/126—Acylisethionates
    • 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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/32—Organic compounds, e.g. vitamins containing sulfur

Definitions

  • This invention relates to a detergent bar having superior use properties and containing an acyl isethionate as the principal detergent component together with supplemental detergent, binder and plasticizer components.
  • a good toilet soap bar should have good lathering properties in hot or cold Water, in hard or soft water, the skin should not be left feeling sticky or itchy, the bar itself should have a good feel and slip, the bar must be mild and nonirritating and the detergency should be good, so that the skin will be cleansed readily in the presence of oil.
  • a detergent bar having these desirable properties is disclosed in United States Patent No. 2,894,912 to Robert C. Geitz.
  • the principal components of a detergent bar com bining the above-mentioned use properties are:
  • Water-soluble alkali metal detergent salts of esters of isethionic acid with mixed fatty acids At least one water-soluble sudsboosting detergent salt From 30% to 70%.
  • Geitz discloses that generally about 2%.% soap is required to prevent cracking in a detergent bar of the above description.
  • the present invention is not limited to use in connection with detergent bars containing at least 2 /2 soap.
  • the foregoing composition may tend to be undesirably soft, especially when more than about 4% to 5% Water is present.
  • Such amounts of water, or even larger amounts of Water Will commonly be present in the detergent mixture as a result of water present in the various ingredients employed therein.
  • the blend may be heated to a temperature above about the boiling point of water in order to reduce the water content to a reasonable value, in the order of 4% to 5%. While theoretically substantially all of the Water could be removed in this manner, to do so is impractical in the commercial preparation of detergent bars.
  • acyl isethionate which is employed can be defined by the following formula:
  • R is a mixture of aliphatic hydrocarbon radicals of fatty acids having from 6 to 18 carbon atoms and an iodine value of less than about 20, and M is an alkali metal cation such as sodium or potassium.
  • the iodine value of the mixed fatty acids is the average value of the mixture and is measured on the mixture.
  • the number of carbon atoms of the acids comprising the R radical is important.
  • acids having a major portion of C and C acids should be employed, and the mixture should contain generally less than about 25% of acids containing from 6 to 10 carbon atoms.
  • the fatty acids should be mostly saturated.
  • the iodine value of the mixture should preferably be less than 20.
  • Such acid mixtures can be made up synthetically but they are conveniently available as the mixed fatty acids derived from coconut oil, palm kernel oil (hydrogenated 0r unhydrogenated), babassu oil, and ouri curi oil.
  • Fatty acids derived from petroleum may also be used, the acids derived from the Koch or Oxo processes or from alpha olefins being typical.
  • the detergent should not contain more than about 30% or 40% of fatty acids having 16 or more carbon atoms, particularly the saturated acids such as palmitic and stearic acids.
  • the amount of acyl isethionate may range from 30% to based on the active detergent, by weight of the nonsoap bar. In order to assure that lime soap curds will not be formed, generally at least 40% and preferably in excess of 48% of the nonsoap bar should be the acyl isethionate. For economic reasons, it will be preferred that the amount of acyl isethionate should not exceed about 53%.
  • Suds-boosting detergents which can be used are the higher aliphatic alcohol sulfates, the alkyl-aryl sulfonates, and the higher aliphatic fatty acid taurides, particularly the fatty acid amides of N-methyl taurine, or a mixture of any two or more of these detergents.
  • the alkyl-aryl sulfonates have the best suds-boosting properties and are preferred.
  • R-SOJOM U SO cation of an organic amine base such as triethanolamine, triisopropanolamine, diethanolamine and monoethanolamine
  • R is hydrogen or a lower alkyl radical of up to five carbon atoms, such as methyl, ethyl, butyl and pentyl.
  • Alkyl-aryl sulfonates are a preferred class of sudsboosters. These may be either the phenyl polypropylene sulfonates in which the polypropylene radical (R in the above general formulae) has a molecular weight corresponding to from about 12 to about 15 carbon atoms or the linear alkyl benzene sulfonates, the latter having a desirable biodegradability.
  • sodium and potassium keryl benzene sulfonates sodium nonyl benzene sulfonate, potassium nonyl toluene sulfonate, sodium dodecyl toluene sulfonate, potassium dodecyl benzene sulfonate and sodium ethyl hexyl benzene sulfonate.
  • Typical alkyl sulfates are sodium lauryl sulfate, sodium palmityl sulfate and triethanolamine myristyl sulfate.
  • Typical fatty acid taurides are sodium palmityl N- methyl tauride, sodium oleyl N-methyl tauride, sodium tauride, sodium oleyl tauride, and sodium coconut oil fatty acids N-methyl tauride.
  • the amount of supplemental suds-boosting synthetic detergent or detergent mixture may range from 2% to 10%. Generally, increasing the amount from 5% to does not lead to appreciably improved sudsing. Therefore, the optimum amounts are between about 2% and about 5%.
  • the aliphatic carboxylic acids which are employed as binder-plasticizers in the free acid form, have a relatively high molecular weight to take advantage of the waxy and lubricant characteristics of such acids.
  • the acids may be saturated or unsaturated and may be straight chain or branched chain, and have from about 12 to about carbon atoms.
  • the unsaturated mixtures should have an iodine value of less than about 20.
  • Synthetic acids, derived from petroleum by the Koch or 0x0 processes or from alpha olefins may
  • the preferred binder-plasticizer is a mixture of the 16 carbon and 18 carbon saturated fatty acids, i.e., palmitic and stearic acids, in a ratio of between about :70 and 70:30 by weight.
  • Commercially available triple pressed stearic acid and its mixtures with palmitic acid are especially preferred binder-plasticizers.
  • a solid polyethylene glycol can be substituted for a part of the acid binder-plasticizer.
  • the polyethylene glycol makes plodding and stamping of the bar easier, and improves the feel of the bar in very cold water.
  • a mixture of 5% polyethylene glycol and 20% triple-pressed stearic acid is satisfactory.
  • these materials are water-soluble, their use tends to make the bar more soluble in water, leading to excessive wasting, and therefore the amount of this material would be kept at a minimum. No more than 20% by weight of the nonsoap bar should be a solid polyethylene glycol.
  • the amount of aliphatic carboxylic acid may be between about 10% and about of the finished bar (by weight). Preferably, however, the bar will contain between about 18% and about 24% by weight of the carboxylic acid.
  • the aliphatic carboxylic acid serves as the principal plasticizer in the nonsoap bars of the invention.
  • Water is used as a supplemental plasticizer. Bars may be made without water. However, to improve plasticity and reduce brittleness so that the bars have little or no tendency to shatter on impact, water should be present. Too much water will make the bar too sticky to process, while if too little is used, the bar will become hard and brittle shortly after being stamped.
  • the amount of water may range up to 9%, preferably from 3.5 to 7%, of the finished bar, depending somewhat upon processing limitations in the available equipment. The amount of water is closely correlated with the plodding conditions.
  • the soaps appropriate for use in detergent bars according to Geitz are the well-known alkali metal salts of fatty acids, i.e., soaps derived from naturally-occurring fats and oils such as coconut oil, palm oil, palm kernel oil, tallow, hydrogenated tallow, hydrogenated lard, hy drogenated white grease, stearic acid, palmitic acid,.hydrogenated palmitic acid, hydrogenated oleic acid, and lauric acid. From 10% to 18% of soap by weight will improve sudsing as well as the bar texture or feel.
  • soaps derived from naturally-occurring fats and oils such as coconut oil, palm oil, palm kernel oil, tallow, hydrogenated tallow, hydrogenated lard, hy drogenated white grease, stearic acid, palmitic acid,.hydrogenated palmitic acid, hydrogenated oleic acid, and lauric acid. From 10% to 18% of soap by weight will improve sudsing as well as the bar texture
  • the total amount of soap added will depend to a certain extent upon the amount of the fatty acid binder. There should be between about 2 /2 to 6 parts by weight of soap for each 10 parts of fatty acid binder. The preferred range stated 'by Geitz is between about 4 and 5 parts of soap for each 10 parts of fatty acid binder.
  • the same class of isethionates which may be employed for the preparation of the principal detergent active ingredient is suitable for the purpose of improving the hardness of the detergent bar.
  • These are specifically the alkali metal salts of isethionic acid.
  • Sodium isethionate is particularly valuable for commercial purposes because it is readily available. Potassium isethionate may also be used.
  • the free isethionate used will most conveniently be the same isethionate which is esterified to form the principal detergent active ingredient, a different isethionate from the above-mentioned class may be used.
  • isethionate esters can be prepared by reacting the free isethionate with a fatty acid chloride, this method being well-established commercially for the preparation of the isethionate esters. Commonly, this process will leave a sufficient amount of free isethionate in the isethionate ester so that when the ester is used in the manufacture of a detergent bar containing approximately isethionate ester, the resulting bar will contain approximately 2.5% free isethionate. This amount will contribute to the desired plodding characteristics.
  • hardness may be increased by decreasing the amount of plasticizer (i.e., the free higher fatty acid) and substituting therefor an inert filler such as sodium chloride.
  • hardness may be increased by decreasing the amount of water present in the detergent bar.
  • Formulation 1 2 3 Fatty acid isethionates 49. 00 49.00 49.00 Mixed polypropylene benzene suifonates.- 2. 03 2. 03 2. 03 Mixed palmitic and stearic acids and fatty acids from fatty acid isethionate 20. 00 20. 00 20. 00 Mixed palmitie and stearic acids added. 10. 50 7. 40 5. 40 Sodium isethionate from fatty acid isethionates l. 90 1. 90 1. 90 Sodium isethionate added 0 3. 00 5. 00 Soap: 80/20 tallow/coco 10. 00 10. 00 10. 00 H5O 4. 75 4. 75 4. 75 Miscellaneous 1. 82 1. 82 1. 82 Hardness:
  • Isethionates may be used as hardening agents for the purpose of improving processing characteristics in conjunction with other hardening agents.
  • a detergent bar was prepared by the following procedure:
  • Formulation 4 5 6 7 Fatty acid isethionates 51.10 61. 10 51. 10 51. 10 Mixed polypropylene benzene sulfonates across 2.03 2.03 2. 03 2. 03 Mixed palmitic and stearic acids and fatty acids from fatty acid isethionate 15. 78 15. 78 15.78 15. 78 Mixed paimitic and stearie acids added 10. 70 5. 70 0. 70 0 Sodium isethionate from fatty acid isethionates 1. 90 1. 90 1.90 Sodium isethionate added. 0 5.00 10.00 15. 00 Soap: 80/20 tailow/coco 8 0 50 5 4. 20 H2 4. 75 4. 75 4. 75 Misceiianeous 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 2. 24 Hardness:
  • Examples 1 and 2 may be repeated substituting about 5% polyethylene glycol having a molecular Weight of 4,000 for a portion of the mixed fatty acids employed therein.
  • potassium isethionate may be substituted for the sodium isethionate. In each case similar results will be obtained.
  • a detergent bar consisting essentially of from 30% to 70% of water-soluble alkali metal detergent salts of esters of isethionic acid with mixed aliphatic fatty acids having from 6 to 18 carbon atoms having an iodine value of less than 20 and containing up to about 25% fatty acids having from 6 to 12 carbon atoms, from 2% to 10% of at least one water-soluble suds-boosting detergent salt selected from the group consisting of alkali metal and organic amine higher aliphatic fatty alcohol sulfates, alkyl aryl sulfonates and higher aliphatic fatty acid ta-urides, from about 1% to about 9% water, from about 2.5% to about 25 of water-soluble higher fatty acid soaps, from about 10% to about 40% of at least one higher fatty acid having about 12 to about 25 carbon atoms as a binder and plasticizer, and from about 4% to about 17% of unesterified water-soluble alkali metal 1
  • salts of isethionic acid said bar having a -pH between about 6 and about 8 when measured as a 10% aqueous solution of the bar composition at 35 C.
  • a detergent bar according to claim 1 containing between about 4% and about 7% of unesterified watersoluble alkali metal salts of isethionic acid.
  • a detergent bar according to claim 1 wherein up to about 20% by weight of the fatty acid is replaced with a solid polyethylene glycol.
  • a detergent bar according to claim 1 containing between about 18% and about 24% of fatty acids having between about 12 and about 25 carbon atoms.
  • a detergent bar according to claim 1 containing between about 3.5 and about 7% water.
  • a detergent bar consisting essentially of from about 48% to about 53% of water-soluble alkali metal detergent salts of esters of isethionic acid with mixed aliphatic fatty acids having from 6 to 18 carbon atoms having an iodine value of less than 20 and containing up to about 25% fatty acids having from 6 to 12 carbon atoms, from 2% to about 5% of an alkyl aryl sulfonate, from about 3.5% to about 7% water, from about 10% to about 18% of a water soluble higher fatty acid soap, from about 18% to about 24% of at least one higher fatty acid having from about 12 to about 25 carbon atoms as a binder and plasticizer, and from about 4% to about 7% of unesterified water-soluble alkali metal salts of isethionic acid, said bar having a pH between about 6 and about 8 when measured as a 10% aqueous solution of the bar composition at 35 C.
  • a detergent bar according to claim 6 containing from about 48% to about 53% of the ester of sodium isethionate and fatty acids derived from coconut oil.
  • a detergent bar according to claim 6 containing from about 4% to about 7% unesterified sodium isethionate.
  • Claim 6, line 6, change "12" to lO-.

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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)
US417801A 1964-12-11 1964-12-11 Synthetic detergent bar Expired - Lifetime US3376229A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US417801A US3376229A (en) 1964-12-11 1964-12-11 Synthetic detergent bar
CH1677365A CH479695A (de) 1964-12-11 1965-12-06 Reinigungsmittelstück
ES0320479A ES320479A1 (es) 1964-12-11 1965-12-07 Un procedimiento para la preparacion de una barra detergente.
BE673468A BE673468A (de) 1964-12-11 1965-12-08
GB52256/65A GB1130705A (en) 1964-12-11 1965-12-09 Synthetic detergent bar
DEU12261A DE1277497B (de) 1964-12-11 1965-12-09 Reinigungsmittelstueck
SE16052/65A SE339969B (de) 1964-12-11 1965-12-10
AT1111965A AT255008B (de) 1964-12-11 1965-12-10 Reinigungsmittelstück
LU50034A LU50034A1 (de) 1964-12-11 1965-12-10
FR41845A FR1460223A (fr) 1964-12-11 1965-12-10 Pain de détergent synthétique
NL656516149A NL148102B (nl) 1964-12-11 1965-12-10 Gevormde wasmiddelen.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US417801A US3376229A (en) 1964-12-11 1964-12-11 Synthetic detergent bar

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US3376229A true US3376229A (en) 1968-04-02

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US417801A Expired - Lifetime US3376229A (en) 1964-12-11 1964-12-11 Synthetic detergent bar

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US (1) US3376229A (de)
AT (1) AT255008B (de)
BE (1) BE673468A (de)
CH (1) CH479695A (de)
DE (1) DE1277497B (de)
ES (1) ES320479A1 (de)
FR (1) FR1460223A (de)
GB (1) GB1130705A (de)
LU (1) LU50034A1 (de)
NL (1) NL148102B (de)
SE (1) SE339969B (de)

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951842A (en) * 1973-04-02 1976-04-20 Lever Brothers Company Synthetic detergent bar with antimushing agent
US3989647A (en) * 1973-04-26 1976-11-02 Lever Brothers Company Quick lathering toilet bars and method of making same
US4046717A (en) * 1972-01-28 1977-09-06 Lever Brothers Company Detergent bars
US4058487A (en) * 1973-11-28 1977-11-15 Lever Brothers Co. Quick lathering toilet bars and method of making same
US4092260A (en) * 1973-11-28 1978-05-30 Lever Bros. Co. Quick lathering toilet bars and method of making same
DE2830827A1 (de) * 1977-07-15 1979-01-25 Colgate Palmolive Co Toilettenseifenzusammensetzung und verfahren zu ihrer herstellung
US4180470A (en) * 1977-03-30 1979-12-25 Lever Brothers Company Method for improved acyl isethionate detergent bars
US4211675A (en) * 1978-01-19 1980-07-08 Lever Brothers Company Detergent bars with improved slip properties
US4231904A (en) * 1978-03-01 1980-11-04 Lever Brothers Company Detergent bars with improved properties
US4234464A (en) * 1979-04-09 1980-11-18 Gaf Corporation Detergent bar composition and binder therefor
US4260507A (en) * 1970-08-18 1981-04-07 Lever Brothers Company Soap-synthetic detergent tablets
US4268424A (en) * 1973-01-15 1981-05-19 Lever Brothers Company Detergent bars containing di-, hydroxy and/or amino-carboxylic acid moisturizers
US4663070A (en) * 1985-01-25 1987-05-05 Lever Brothers Company Process for preparing soap-acyl isethionate toilet bars
US4695395A (en) * 1984-09-25 1987-09-22 Lever Brothers Company Cleaning compositions with skin protection agents
US4707288A (en) * 1984-10-08 1987-11-17 Lever Brothers Company Process for preparing detergent bars
US4808322A (en) * 1988-03-10 1989-02-28 Mclaughlin James H Skin cleansing-cream conditioning bar
US4851147A (en) * 1987-02-26 1989-07-25 Finetex, Inc. Transparent combination soap-synthetic detergent bar
US4941990A (en) * 1988-03-10 1990-07-17 Mclaughlin James H Skin cleansing-cream conditioning bar
EP0287300A3 (en) * 1987-04-13 1990-12-27 Unilever Plc Cleaning compositions
WO1991008278A1 (de) * 1989-11-30 1991-06-13 Henkel Kommanditgesellschaft Auf Aktien Geformte körperreinigungsmittel
WO1991013958A1 (en) * 1990-03-05 1991-09-19 The Procter & Gamble Company Improved personal cleansing stamped synbar
US5096608A (en) * 1985-05-13 1992-03-17 The Procter & Gamble Company Ultra mild skin cleansing composition
US5284598A (en) * 1991-12-04 1994-02-08 Colgate-Palmolive Company Process for making mild, detergent-soap, toilet bars and the bar resulting therefrom
US5482643A (en) * 1993-05-19 1996-01-09 Lever Brothers Company, Division Of Conopco, Inc. Soap bars made with ternary system of fatty isethionate ester, fatty acid, and water
US5496493A (en) * 1994-05-10 1996-03-05 The Procter & Gamble Company Ultra mild personal cleansing bar containing smaller-sized particulate wax
US5646320A (en) * 1993-10-28 1997-07-08 Henkel Corporation Process for making isethionate ester salts
US5763632A (en) * 1993-10-28 1998-06-09 Henkel Corporation Process for making isethionate ester salts
US6251843B1 (en) 1994-03-15 2001-06-26 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Synthetic detergent bar and manufacture thereof
US20050124515A1 (en) * 2002-01-31 2005-06-09 Ospinal Carlos E. Soap bar compositions comprising alpha sulfonated fatty acid alkyl estersand polyhydridic alcohols and process for producing same
US20060002883A1 (en) * 2004-07-01 2006-01-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Mild synthetic detergent toilet bar composition
US20060089279A1 (en) * 2004-10-26 2006-04-27 Brennan Michael A Mild acyl isethionate toilet bar composition
US20060241003A1 (en) * 2002-01-31 2006-10-26 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester and polyhydric alcohol and process for producing the same
US20060258551A1 (en) * 2002-01-31 2006-11-16 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester and polyhydric alcohol and process for producing the same
US20070004611A1 (en) * 2002-01-31 2007-01-04 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester or sulfonated fatty acid and synthetic surfactant and process for producing the same
US20080058237A1 (en) * 2004-10-26 2008-03-06 Unilever Home & Personal Care Usa, Division Of Conopco Mild acyl isethionate toilet bar composition
US20080272339A1 (en) * 2007-05-02 2008-11-06 Conopco, Inc. D/B/A Unilever No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
WO2018104115A1 (en) 2016-12-06 2018-06-14 Unilever Plc Synthetic detergent bars
US12473517B2 (en) 2019-10-30 2025-11-18 Coversan, Llc Method of use for toilet waste material treatment

Families Citing this family (8)

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CA1304270C (en) * 1984-09-25 1992-06-30 Michael Lynn Caswell Cleaning compositions with skin protection agents
WO1992013060A2 (en) * 1991-01-28 1992-08-06 The Procter & Gamble Company Binder systems for bar soaps
WO1995016022A1 (en) * 1991-12-04 1995-06-15 Colgate-Palmolive Company Process for toilet bars and resulting bar
GB9305377D0 (en) * 1993-03-16 1993-05-05 Unilever Plc Synthetic detergent bar and manufacture thereof
US6028042A (en) * 1994-03-15 2000-02-22 Lever Brothers Company Synthetic bar comprising high levels of alkylene oxide as structurant prepared by simple mix process
WO2017011774A1 (en) * 2015-07-15 2017-01-19 Nohbo, LLC Hygiene product tablet and methods of forming same
USD931526S1 (en) 2018-08-03 2021-09-21 Nohbo, LLC Hygiene product pod
US11045397B2 (en) 2019-11-06 2021-06-29 Nohbo, LLC Hygiene product pod and methods of using same

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CA560328A (en) * 1958-07-15 C. Britton Edgar Continuous production of salts of hydroxy aliphatic sulfonic acids
US2894912A (en) * 1954-09-21 1959-07-14 Lever Brothers Ltd Isethionate detergent bar
DE1111617B (de) * 1959-05-30 1961-07-27 Hoechst Ag Verfahren zur Herstellung von Ammonium- oder N-substituierten Ammoniumsalzen von (2)-Hydroxyal-kansulfonsaeuren

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US2894912A (en) * 1954-09-21 1959-07-14 Lever Brothers Ltd Isethionate detergent bar
DE1111617B (de) * 1959-05-30 1961-07-27 Hoechst Ag Verfahren zur Herstellung von Ammonium- oder N-substituierten Ammoniumsalzen von (2)-Hydroxyal-kansulfonsaeuren

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US4260507A (en) * 1970-08-18 1981-04-07 Lever Brothers Company Soap-synthetic detergent tablets
US4046717A (en) * 1972-01-28 1977-09-06 Lever Brothers Company Detergent bars
US4268424A (en) * 1973-01-15 1981-05-19 Lever Brothers Company Detergent bars containing di-, hydroxy and/or amino-carboxylic acid moisturizers
US3951842A (en) * 1973-04-02 1976-04-20 Lever Brothers Company Synthetic detergent bar with antimushing agent
US3989647A (en) * 1973-04-26 1976-11-02 Lever Brothers Company Quick lathering toilet bars and method of making same
US4110239A (en) * 1973-11-28 1978-08-29 Lever Bros. Co. Quick lathering toilet bars and method of making same
US4096082A (en) * 1973-11-28 1978-06-20 Lever Brothers Company Quick lathering toilet bars and method of making same
US4092260A (en) * 1973-11-28 1978-05-30 Lever Bros. Co. Quick lathering toilet bars and method of making same
US4058487A (en) * 1973-11-28 1977-11-15 Lever Brothers Co. Quick lathering toilet bars and method of making same
US4180470A (en) * 1977-03-30 1979-12-25 Lever Brothers Company Method for improved acyl isethionate detergent bars
DE2830827A1 (de) * 1977-07-15 1979-01-25 Colgate Palmolive Co Toilettenseifenzusammensetzung und verfahren zu ihrer herstellung
US4211675A (en) * 1978-01-19 1980-07-08 Lever Brothers Company Detergent bars with improved slip properties
US4231904A (en) * 1978-03-01 1980-11-04 Lever Brothers Company Detergent bars with improved properties
US4234464A (en) * 1979-04-09 1980-11-18 Gaf Corporation Detergent bar composition and binder therefor
US4695395A (en) * 1984-09-25 1987-09-22 Lever Brothers Company Cleaning compositions with skin protection agents
US4707288A (en) * 1984-10-08 1987-11-17 Lever Brothers Company Process for preparing detergent bars
US4663070A (en) * 1985-01-25 1987-05-05 Lever Brothers Company Process for preparing soap-acyl isethionate toilet bars
US5096608A (en) * 1985-05-13 1992-03-17 The Procter & Gamble Company Ultra mild skin cleansing composition
US4851147A (en) * 1987-02-26 1989-07-25 Finetex, Inc. Transparent combination soap-synthetic detergent bar
EP0287300A3 (en) * 1987-04-13 1990-12-27 Unilever Plc Cleaning compositions
US5030376A (en) * 1987-04-13 1991-07-09 Lever Brothers Company, Division Of Conopco, Inc. Delta phase soap and non-soap detergent composition
US4808322A (en) * 1988-03-10 1989-02-28 Mclaughlin James H Skin cleansing-cream conditioning bar
US4941990A (en) * 1988-03-10 1990-07-17 Mclaughlin James H Skin cleansing-cream conditioning bar
WO1991008278A1 (de) * 1989-11-30 1991-06-13 Henkel Kommanditgesellschaft Auf Aktien Geformte körperreinigungsmittel
WO1991013958A1 (en) * 1990-03-05 1991-09-19 The Procter & Gamble Company Improved personal cleansing stamped synbar
US5393449A (en) * 1990-03-05 1995-02-28 The Procter & Gamble Company Personal cleansing stamped synbar containing alkyl glyceryl ether sulfonate and acyl isethionate
US5284598A (en) * 1991-12-04 1994-02-08 Colgate-Palmolive Company Process for making mild, detergent-soap, toilet bars and the bar resulting therefrom
US5482643A (en) * 1993-05-19 1996-01-09 Lever Brothers Company, Division Of Conopco, Inc. Soap bars made with ternary system of fatty isethionate ester, fatty acid, and water
US5646320A (en) * 1993-10-28 1997-07-08 Henkel Corporation Process for making isethionate ester salts
US5763632A (en) * 1993-10-28 1998-06-09 Henkel Corporation Process for making isethionate ester salts
US6251843B1 (en) 1994-03-15 2001-06-26 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Synthetic detergent bar and manufacture thereof
US5496493A (en) * 1994-05-10 1996-03-05 The Procter & Gamble Company Ultra mild personal cleansing bar containing smaller-sized particulate wax
US20060241003A1 (en) * 2002-01-31 2006-10-26 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester and polyhydric alcohol and process for producing the same
US20080058236A1 (en) * 2002-01-31 2008-03-06 Ospinal Carlos E Soap Bar Compositions Comprising Alpha Sulfonated Alkyl Ester or Sulfonated Fatty Acid and Synthetic Surfactant and Process for Producing the Same
US20050124514A1 (en) * 2002-01-31 2005-06-09 Ospinal Carlos E. Soap bar compositions comprising alpha sulfonated alkyl ester and polyhyridic alcohol and process for producing the same
US20070004611A1 (en) * 2002-01-31 2007-01-04 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester or sulfonated fatty acid and synthetic surfactant and process for producing the same
US20060258551A1 (en) * 2002-01-31 2006-11-16 Ospinal Carlos E Soap bar compositions comprising alpha sulfonated alkyl ester and polyhydric alcohol and process for producing the same
US20050124515A1 (en) * 2002-01-31 2005-06-09 Ospinal Carlos E. Soap bar compositions comprising alpha sulfonated fatty acid alkyl estersand polyhydridic alcohols and process for producing same
WO2006002890A1 (en) * 2004-07-01 2006-01-12 Unilever Plc Mild synthetic detergent toilet bar composition
US20060002883A1 (en) * 2004-07-01 2006-01-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Mild synthetic detergent toilet bar composition
US20060089279A1 (en) * 2004-10-26 2006-04-27 Brennan Michael A Mild acyl isethionate toilet bar composition
US20080058237A1 (en) * 2004-10-26 2008-03-06 Unilever Home & Personal Care Usa, Division Of Conopco Mild acyl isethionate toilet bar composition
US7737096B2 (en) 2004-10-26 2010-06-15 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Mild acyl isethionate toilet bar composition
US20080272339A1 (en) * 2007-05-02 2008-11-06 Conopco, Inc. D/B/A Unilever No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
WO2008135316A1 (en) * 2007-05-02 2008-11-13 Unilever Plc No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
US7579311B2 (en) 2007-05-02 2009-08-25 Conopco, Inc. No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
WO2009043716A1 (en) 2007-10-04 2009-04-09 Unilever Plc Mild acyl isethionate toilet bar composition
WO2018104115A1 (en) 2016-12-06 2018-06-14 Unilever Plc Synthetic detergent bars
US11384320B2 (en) 2016-12-06 2022-07-12 Conopco, Inc. Synthetic detergent bars
US12473517B2 (en) 2019-10-30 2025-11-18 Coversan, Llc Method of use for toilet waste material treatment

Also Published As

Publication number Publication date
BE673468A (de) 1966-06-08
NL6516149A (de) 1966-06-13
SE339969B (de) 1971-11-01
GB1130705A (en) 1968-10-16
AT255008B (de) 1967-06-26
LU50034A1 (de) 1966-06-10
ES320479A1 (es) 1966-10-16
FR1460223A (fr) 1966-06-17
CH479695A (de) 1969-10-15
DE1277497B (de) 1968-09-12
NL148102B (nl) 1975-12-15

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