US3474038A - Detergent compositions containing n-(2-hydroxyalkyl)-omega-methyltaurine - Google Patents

Detergent compositions containing n-(2-hydroxyalkyl)-omega-methyltaurine Download PDF

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Publication number
US3474038A
US3474038A US493804A US3474038DA US3474038A US 3474038 A US3474038 A US 3474038A US 493804 A US493804 A US 493804A US 3474038D A US3474038D A US 3474038DA US 3474038 A US3474038 A US 3474038A
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Prior art keywords
detergent
hydroxyalkyl
liquid
organic
methyltaurine
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Expired - Lifetime
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US493804A
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English (en)
Inventor
Ralph Raymond Sepulveda
Frank Vincent Cieri
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Lever Brothers Co
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Lever Brothers Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • 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
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • 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
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea

Definitions

  • This invention relates to certain novel liquid detergent formulations.
  • the salts of certain N-(2-hydroxyalkyl)- N-methyltaurines with water-solubilizing cations exhibit unexpected hydrotroping activity, and may be used for this purpose in detergent formulations.
  • detergent adjuncts may be present, such adjuncts being Well known in the art for modifying variou properties of the detergent formulation but not changing its essential detersive nature.
  • To such a detergent formulation is added from 2% to 35% of a C to C N (2 hydroxyalkyl) N-methyltaurine, the amount thereof relative to said detergent being sufficient to yield a homogeneous mixture.
  • the present invention is of particular applicability to detergent formulations consisting essentially of from 2% to 35% of a surface-active organic detergent, a builder to improve the detergency properties of said detergent and sufficient water to liquefy the formulation, the amount of the detergent being sufiicient normally to yield a formulation having more than one liquid phase. It has been found that the presence of a builder, and especially the inorganic alkaline phosphates, tends to make the organic detergents more difficultly soluble. As in the broad concept of the present invention, an amount of a C to C N-(2-hydroxyalkyl)-N-methyltaurine is present, generally etween 2% and 35% of the formulation, which is sufficient to render the liquid homogeneous. As a rule, when a builder is present, the ratio of N-(2-hydroxyalkyl)-N- methyltaurine to detergent necessary to obtain a homogeneous liquid is greater in the prescence of a builder than in its absence.
  • miscellaneous ingredients may be added to improve the properties of the detergent formulation but which do not change the essential nature thereof. Usually not more than about 10% to 20% of the formulation will be composed of such ingredients; although larger amounts of miscellaneous ingredients may be present especially if the principal active ingredients contain significant amounts of more or less inert impurities. Possible miscellaneous ingredients include, but are not limited to, thickeners, fillers, soil suspending agents, dyes, perfumes, colorants, optical brighteners, germicides, opacifiers, and the like.
  • the second class of useful detergents are the nonionic surface-active compounds.
  • Nonionic detergents are generally prepared by the condensation of ethylene oxide with one or more organic compounds containing an active hydrogen.
  • the commercially important nonionic detergents are generally condensates of ethylene oxide with either hydroxy-containing hydrophobic organic compounds, e.g. polypropylene glycol or fatty alcohols, or amino-containing organic compounds; however, many others have been proposed in the literature.
  • Biodegradable nonionic detergents based on linear fatty alcohols are known and may be used in the present invention.
  • the organic compound may be either alkyl alkenyl, alkylaryl or alkenylaryl and contain other substituent groups, i.e. ether linkages such as in the polyoxypropylene-based compounds.
  • the builders which are contemplated are the generally recognized soluble alkaline phosphates, such as the alkali metal, pyrophosphates and polyphosphates. Tetrasodium pyrophosphate, tetrapotassium pyrophosphate, sodium tripolyphosphate, potassium tripolyphosphates, and the simple sodium or potassium phosphates are the most common of the phosphate builders commercially available.
  • the phosphate builders, when used, are commonly pres ent in a concentration of from 5% to 20%.
  • organic builders may be used. Certain of the organic amides mentioned below, for example, are well known to be effective builders. Nitriloacetic acid salts are another known group of organic builders which may be used in the present invention.
  • organic amides contemplated have the following general formula:
  • R being a long-chain radical containing from about 8 to about 18 carbon atoms and R and R each being selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl. There should be no more than one hydrogen attached to the nitrogen atom.
  • Typical compounds include, but are not limited to, coco diethanol amide, and lauric isopropanol amide.
  • the amides are employed for the purpose of improving the foaming or detergency properties of the formulation.
  • the organic amides, when used, are conventionally present in a concentration between about 2% and about 15%.
  • Example 1 Percent Sodium salt of N (2 hydroxyoctyl) N methyl taurine 24 Sodium lauryl sulfate 6 Water 70
  • Example 2 Sodium salt of N (2 hydroxyoctyl) N methyl taurine 12 Sodium Alfol 14124.1 E.O. sulfate 18
  • compositions of the N-(2- hydroxyalkyl)-Nmethyltaurine (HAMT) plus a second detergent may be used in conjunction with various builders.
  • Liquid detergent compositions illustrating the foregoing are as follows:
  • Example 3 Percent by Weight Ingredients A B 62.5. Description of composition Opaque liquid Clear homoslight organic geneous separation at liquid. surface of liquid.
  • Example 4 Percent by Weight Ingredients A B Cm HAMT l- 8. Polypropylene benzene suli'onate a 2 2. Sodium tripolyphosphate..- 5.. 5. Water 93... 85. Description of composition Orga s Clear homoprecipitate geneous. from liquid.
  • a Mole weight of sulionic acid is 325.
  • Example 6 Ingredients: Percent by wt.
  • Example 7 Sufiicient N-(2-hydroxyalkyl)-N-methyltaurine is added to a mixture of 100 parts of the above liquid laundry detergent and about 5 parts of distearyl dimethyl ammonium chloride to yield a homogeneous liquid. Without N-(Z-hydroxyalkyl)-N-methyltaurine a multi-layer separation occurs.
  • a liquid detergent composition consisting essen tially of:
  • a second organic surface-active material having detergent properties said second detergent material being selected from the group consisting of detergent salts of organic sulfonic and sulfuric acids containing between about 8 and 18 carbon atoms, nonionic condensates of ethylene oxide having detergent properties and cationic organic compounds having detergent properties and containing a quaternary nitrogen atom in the molecule; and
  • the amount of said second organic surface-active detergent material relative to the amount of said Water being sufiicient that a liquid detergent containing more than one phase would result in the absence of said -N-(Z-hydroxyalkyD-N-methyl taurine, and the amount of said N-(Z-hydroxylalkyl)-N-methyl taurine being between about 2% and about 35% by weight of said Water, and suflicient to yield a homogeneous liquid.
  • a liquid detergent composition consisting essentially of:
  • N-(Z-hydroxyalkyl)-N-methyl taurine having from about 6 to about 12 carbon atoms in the alkyl p;
  • At least one second organic surface-active detergent compound selected from the group consisting of detergent salts of organic sulfonic and sulfuric acids, nonionic condensates of ethylene oxide having detergent properties and cationic organic compounds having detergent properties and containing a quaternary nitrogen in the molecule;
  • a liquid-detergent composition consisting essentially of:
  • R is a long chain acyclic aliphatic hydrocarbon radical having from 8 to about 18 carbon atoms, and R and R are each selected from the group consisting of hydrogen, lower alkyl and lower hydroxy alkyl radicals having up to about 5 carbon atoms, there being no more than 1 hydrogen attached to the nitrogen;
  • a detergent composition in accordance with claim 3 containing from about 2% to about 15% of said organic amide.
  • a detergent composition according to claim 3 wherein the weight ratio of said N-(2-hydroxyalkyl-N-methyltaurine to said detergent is between about 90:10 and 50:50.
  • a detergent composition according to claim 3 Where- FOREIGN PATENTS in said N-(2-hydroxya1kyl)-N-methyltaurine contains 1,332,754 6/1963 France from about 6 to about 10 carbon atoms in the alkyl group.

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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)
US493804A 1965-10-07 1965-10-07 Detergent compositions containing n-(2-hydroxyalkyl)-omega-methyltaurine Expired - Lifetime US3474038A (en)

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US49380465A 1965-10-07 1965-10-07

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US3474038A true US3474038A (en) 1969-10-21

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US (1) US3474038A (en])
AT (1) AT270028B (en])
BE (1) BE687983A (en])
CH (1) CH484267A (en])
DE (1) DE1617211A1 (en])
DK (1) DK126127B (en])
ES (1) ES332021A1 (en])
FI (1) FI45207C (en])
FR (1) FR1495993A (en])
GB (1) GB1132146A (en])
LU (1) LU52129A1 (en])
NL (1) NL6614061A (en])
SE (1) SE315063B (en])

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3894077A (en) * 1973-02-27 1975-07-08 Daicel Ltd Antistatic agent for plastics
US4476043A (en) * 1982-05-13 1984-10-09 Henkel Corporation Surfactant product
US4582651A (en) * 1979-12-27 1986-04-15 Nippon Paint Co., Ltd. Process for preparing hydroxyalkylaminosulfonic acids

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1332754A (fr) * 1961-06-13 1963-07-19 Unilever Nv Préparation de composés organiques notamment des n-(2-hydroxyalkyl)-n-méthyltaurines et leurs sels alcalins
US3254028A (en) * 1961-02-06 1966-05-31 Colgate Palmolive Co Liquid detergent composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254028A (en) * 1961-02-06 1966-05-31 Colgate Palmolive Co Liquid detergent composition
FR1332754A (fr) * 1961-06-13 1963-07-19 Unilever Nv Préparation de composés organiques notamment des n-(2-hydroxyalkyl)-n-méthyltaurines et leurs sels alcalins

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3894077A (en) * 1973-02-27 1975-07-08 Daicel Ltd Antistatic agent for plastics
US4582651A (en) * 1979-12-27 1986-04-15 Nippon Paint Co., Ltd. Process for preparing hydroxyalkylaminosulfonic acids
US4476043A (en) * 1982-05-13 1984-10-09 Henkel Corporation Surfactant product

Also Published As

Publication number Publication date
LU52129A1 (en]) 1967-04-07
DK126127B (da) 1973-06-12
BE687983A (en]) 1967-04-07
DE1617211A1 (de) 1971-02-25
NL6614061A (en]) 1967-04-10
ES332021A1 (es) 1967-10-01
FR1495993A (fr) 1967-09-22
FI45207B (en]) 1971-12-31
CH484267A (de) 1970-01-15
FI45207C (fi) 1972-04-10
AT270028B (de) 1969-04-10
SE315063B (en]) 1969-09-22
GB1132146A (en) 1968-10-30

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