US3707511A - Anionic detergent compositions containing foam boosting succinic acid derivatives - Google Patents

Anionic detergent compositions containing foam boosting succinic acid derivatives Download PDF

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Publication number
US3707511A
US3707511A US69482A US3707511DA US3707511A US 3707511 A US3707511 A US 3707511A US 69482 A US69482 A US 69482A US 3707511D A US3707511D A US 3707511DA US 3707511 A US3707511 A US 3707511A
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US
United States
Prior art keywords
hydroxyethyl
detergent
succinic acid
foam
bis
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
US69482A
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English (en)
Inventor
Vincent Lamberti
Henry Lemaire
Arno Cahn
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Lever Brothers Co
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Lever Brothers Co
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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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • 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
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- 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
    • C11D3/26—Organic compounds containing nitrogen
    • 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
    • C11D3/32—Amides; Substituted amides

Definitions

  • This invention is directed to water-soluble nitrogencontaining compounds and to detergent compositions containing said compounds.
  • a principal object of this invention is to provide novel compositions of matter.
  • Another object of the invention is to provide compounds which are suitable for use as detergent-active ingredients, i.e., cleaning agents, in detergent solutions.
  • a further object of the invention is to provide compounds suitable for use as adjuvants, i.e., foam boosters and stabilizers, in detergent formulations.
  • a still further object of the invention is to provide improved detergent formulations.
  • X is an acylic hydrocarbyl group, i.e., an alkyl group or an alkenyl group, of from about 10 to about 16 carbon atoms, preferably 11 to 15 carbon atoms;
  • a and B are selected from the following groups: Z-hydroxyethylamino [NHCH CH OH], N-methyl-2-hydroxyethylamino [N(CH )CH CH OH], 2 hydroxyethylammouiumoxy [O-N H CH CH OH]; and N-methyl-2-hydroxyethylammoniumoxy [O*N+H (CH )CH CH OH]; ammonium oxy [--ON+H and alkali metal oxy groups [O"M+] wherein M is an alkali metal, preferably sodium or potassium, with the proviso that at least one of the groups A or B must be a nitrogen-containing group, preferably a nitrogen-containing organic group of the groups mentioned above.
  • equivalent amount means an amount which is sufficient to react with both carboxyl groups of the succinic acid.
  • Suitable nitrogen-containing reactants include lower alkanolamines, i.e., 1-4 carbon atoms, such as ethanolamine and N-methylethanolamine, and mixtures of these compounds.
  • the aliphatically substituted succinic acid-producing compound e.g., an aliphatically substituted succinic anhydride
  • hydrocarbyl groups are alkenyl or alkyl groups containing from about 10 to about 16 carbon atoms such as decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, decyl, dodecyl, tridecyl, pentadecyl, and the like.
  • Preferred substituent groups on the succinic acid molecule are those containing from about 11 to about 15 carbon atoms.
  • alkenyl, and particularly 2-alkenyl, nitrogen-containing derivatives constitute preferred groups of compounds for use as suds boosters, stabilizers, and detergent actives.
  • the position of the hydrocarbyl substituent is merely relative.
  • the location of the hydrocarbyl substituent is immaterial since the compound is symmetrical.
  • a or B has an ionic linkage, e.g., in the case of an ammonium salt or an alkali metal salt, the compound is not symmetrical. In such case, the
  • hydrocarbyl group can be located on either the alpha or beta carbons with respect to the carboxy group.
  • Specific compounds having good foam boosting and stabilizing properties include N-hydroxyethyl-N'-hydroxyethyl-ammonium-Z-dodecenylsuccinamate; -N,N'-bis (hydroxyethyl)-2-dodecenylsuccinamide; N,N bis(hydroxyethyl)-2-hexadecenylsuccinamide; and the like.
  • the herein described succinic acid derivatives have been found to be effective as foam improving adjuvants, e.g., foam boosters and foam stabilizers. They have utility as a component of organic detergent formulations, particularly formulations containing organic detergents, such as alkylaryl sulfonates.
  • the compounds of this invention can be incorporated into known detergent formulations, generally in such amounts that the weight to weight ratio of detergent to succinic acid derivative is from about :1 to 1:1 and preferably from about 4:1 to about 3:1.
  • detergent refers to organic compounds which clean by a physico-chemical action involving alternation of surface tension rather than by direct solution or chemical reaction.
  • detergent formulation refers to mixtures containing, in addition to a detergent, any of the well known materials conventionally admixed with detergents. Such materials include fillers, builders, bleaching agents, optical brighteners, dyes, perfumes, soil-suspending agents, suds-boosters, and the like.
  • foam boosters and stabilizers have particularly beneficial effects when used in conjunction with alkylaryl sulfonates of both the biodegradable (LAS) and non-biodegradable types, wherein the alkyl chain con tains an average of from about 7 to about 18 carbon atoms.
  • the alkyl group contains an average of from about to about 14 carbon atoms, such as may be obtained from olefins or kerosene.
  • These detergents are made in a known manner by alkylating the aromatic hydrocarbon and thereafter sulfonating and neutralizing the product with an alkali metal or ammonium-containing compound, e.g., a hydroxide.
  • the temperature of the remaining reaction product was then reduced to about C. and an additional 30 grams of distillate were removed under a vacuum of 2.5 millimeters of mercury.
  • the residue was found to be about 57 grams of the crude reaction product (0.148 mole calculated as; the bisamide) having only one infra-red absorption peak in the carbonyl region at about 6.03 microns.
  • N,N-bis-(hydroxyethyl) alkylsuccinamide is prepared from a mixture of alkylsuccinic anhydrides having from 11 to 15 carbon atoms in the alkyl chain by the procedure shown in Example I, above.
  • the alkylsuccinic anhydride is prepared by hydrogenating the corresponding alkenylsuccinic anhydride.
  • N,N'-bis-(hydroxyethyl) dodecyl succinamide is prepared from dodecylsuccinic anhydride following the procedure outlined in Example I.
  • Example V illustrates the detergent properties of representative compounds within the scope of this invention, as compared with a standard detergent, i.e., an alkyl benzene sulfonate derived from tetraand penta-propylene. Detergency was evaluated by means of a Tergo-o-Tometer, as described in the May 1950 issue of the Journal of the American Oil Chemists Society, pages 153-159.
  • the apparatus was immersed in a water bath adjusted to maintain the temperature of the wash solution at 120 P122".
  • the paddle of the apparatus was adjusted to oscillate through an arc of 320 F. at cycles per minute.
  • the detergent was added to the washpot of the machine and then 1,250 milliliters of water having a hardness of parts per million, calculated as CaCO was added.
  • the machine was started and the solution agitated until the detergent was dissolved.
  • the washpot was emptied and refilled with clear rinse water having the same hardness as the wash water at a temperature of 120 F.i2. The cloths were then agitated in the rinse water for 5 minutes. The cloths were then removed, hand squeezed, and ironed dry.
  • Detergent elficiency was evaluated by measuring and comparing the reflectance of the soiled cloth before washing and the reflectance of the cloth after the washing cycle. Detergency units are the differences between these readings. Reflectance was measured with a Hunter Refiectometer equipped with a green filter.
  • EXAMPLE VI This example illustrates the ability of representative compounds to clean dishes in a standard test which measures the number of uniformly soiled dinner plates which can be cleaned under standard conditions with the composition being tested.
  • the dishes are soiled with a blend of 9 parts by weight of emulsifier-free vegetable shortening, 8 parts by weight of bread flour, and a green dye.
  • each plate is soiled with 1 teaspoonful of the soiling material which is spread evenly over each plate.
  • the dishes are then washed by a standard technique in six quarts of water of uniform hardness (120 p.p.m. as CaCO at a temperature of 116 F. containing a measured amount of the cleaning agents being tested. The end point of the test is reached when the foam produced by the test composition no longer covers the surface of the washing solution.
  • Table 3 shows the number of dishes cleaned by a linear alkyl benzene sulfonate (LAS) having from 9 to about 15 carbon atoms and sodium lauryl sulfate, each with and without a representative N,N'-bis (hydroxyethyl)- 2-alkenylsuccinamide additive, as shown in column 2.
  • LAS linear alkyl benzene sulfonate
  • This example illustrates the ability of the herein disclosed alkenyl succinic acid derivatives to function as foam stabilizers as measured by a standard test in which the weight of soil necessary to destroy the foam produced by 9 grams of the detergent materials in six quarts of 120 p.p.m. hardness (calculated as CaCO was measured.
  • a solution containing only detergent and stabilizer was prepared by dissolving these materials in suflicient water to provide a concentration equivalent to 9 grams per six quarts of water of a detergent composition comprising 30% sodium alkylbenzene sulfonate (propylene tetramer type) and 9% of the stabilizer. Therefore, the solution contained 2.7 grams of sulfonate and 0.81 gram of the stabilizer. The control contained only the detergent. Three hundred milliliters of this solution were placed in a beaker and heated to F. The solution was then transferred to a Waring Blendor and agitated at low speed for one minute, at which point the temperature was about 116 F.
  • soil comprising 9 parts by weight of an emulsifier-free vegetable shortening and 8 parts by weight of bread flour was added dropwise from a weighed beaker of the soil.
  • the soiling agent was warmed to the softening point, but not melted, while being added to the solution.
  • the addition of soil was stopped and the beaker of soil reweighed. The difference in weight for two identical tests was determined and the average reported as a measure of the stability of the foam obtained from the active materials employed.
  • a foamable detergent formulation capable of producing an enhanced amount of foam comprising:
  • an anionic organic detergent selected from the group consisting of:
  • foamable detergent formulation defined by claim 2. wherein the foam improving adjuvant compound is a mixed N,N'-bis(hydroxyethyl) C -C 2-alkenyl succinamide.
  • foam improving adjuvant compound is N,N'- bis (hydroxyethyl) -2- dodecenylsuccinamide.
  • foamable detergent formulation defined by claim 2 wherein the foam improving adjuvant compound is N,N'- bis(hydroxyethyl)-2-hexadecenylsuccinamide.
  • foamable detergent formulation defined by claim 2 wherein the foam improving adjuvant compound is the monoethanolamide/monoethanolammonium salt of 2-dodecenylsuccinic acid.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US69482A 1967-06-13 1970-09-03 Anionic detergent compositions containing foam boosting succinic acid derivatives Expired - Lifetime US3707511A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64563667A 1967-06-13 1967-06-13
US6948270A 1970-09-03 1970-09-03

Publications (1)

Publication Number Publication Date
US3707511A true US3707511A (en) 1972-12-26

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Country Status (6)

Country Link
US (1) US3707511A (enrdf_load_stackoverflow)
BE (1) BE716351A (enrdf_load_stackoverflow)
DE (1) DE1768651B2 (enrdf_load_stackoverflow)
FR (1) FR1568623A (enrdf_load_stackoverflow)
GB (1) GB1215498A (enrdf_load_stackoverflow)
NL (1) NL6808278A (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951880A (en) * 1973-02-02 1976-04-20 Witco Chemical Corporation Anti-dusting alpha-olefin sulfonate detergent compositions
DE2853136A1 (de) * 1977-12-09 1979-07-05 Albright & Wilson Waessriges, oberflaechenaktives mittel
US4692271A (en) * 1977-12-09 1987-09-08 Albright & Wilson Ltd. Concentrated aqueous surfactant compositions
EP0241073A2 (en) 1986-03-31 1987-10-14 The Procter & Gamble Company Liquid detergents containing anionic surfactant, succinate builder and fatty acid
US4753754A (en) * 1977-12-09 1988-06-28 Albright & Wilson Limited Concentrated aqueous surfactant compositions
WO1996016930A1 (en) * 1994-12-02 1996-06-06 Imperial Chemical Industries Plc Succinic acid derivatives and their use as surfactants
JP2012197268A (ja) * 2011-03-04 2012-10-18 Toyo Ink Sc Holdings Co Ltd β−ヒドロキシアルキルアミドおよび架橋性組成物
WO2014142116A1 (ja) * 2013-03-12 2014-09-18 花王株式会社 セラミド様機能付与剤

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9317476D0 (en) * 1993-08-23 1993-10-06 Ici Plc Surfactants

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951880A (en) * 1973-02-02 1976-04-20 Witco Chemical Corporation Anti-dusting alpha-olefin sulfonate detergent compositions
DE2853136A1 (de) * 1977-12-09 1979-07-05 Albright & Wilson Waessriges, oberflaechenaktives mittel
US4692271A (en) * 1977-12-09 1987-09-08 Albright & Wilson Ltd. Concentrated aqueous surfactant compositions
US4753754A (en) * 1977-12-09 1988-06-28 Albright & Wilson Limited Concentrated aqueous surfactant compositions
EP0241073A2 (en) 1986-03-31 1987-10-14 The Procter & Gamble Company Liquid detergents containing anionic surfactant, succinate builder and fatty acid
US5798331A (en) * 1994-12-02 1998-08-25 Imperial Chemical Industries Plc Succinic acid derivatives and their use as surfactants
WO1996016930A1 (en) * 1994-12-02 1996-06-06 Imperial Chemical Industries Plc Succinic acid derivatives and their use as surfactants
JP2012197268A (ja) * 2011-03-04 2012-10-18 Toyo Ink Sc Holdings Co Ltd β−ヒドロキシアルキルアミドおよび架橋性組成物
WO2014142116A1 (ja) * 2013-03-12 2014-09-18 花王株式会社 セラミド様機能付与剤
JP2014198708A (ja) * 2013-03-12 2014-10-23 花王株式会社 セラミド様機能付与剤
CN105188655A (zh) * 2013-03-12 2015-12-23 花王株式会社 类神经酰胺功能赋予剂
CN105188655B (zh) * 2013-03-12 2018-05-08 花王株式会社 类神经酰胺功能赋予剂
US10143667B2 (en) 2013-03-12 2018-12-04 Kao Corporation Ceramide-like function imparting agent

Also Published As

Publication number Publication date
FR1568623A (enrdf_load_stackoverflow) 1969-05-23
GB1215498A (en) 1970-12-09
DE1768651C3 (enrdf_load_stackoverflow) 1978-10-26
DE1768651B2 (de) 1978-03-02
DE1768651A1 (de) 1971-10-28
BE716351A (enrdf_load_stackoverflow) 1968-12-10
NL6808278A (enrdf_load_stackoverflow) 1968-12-16

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