US3821115A - Detergent compositions containing salts of 4-hydroxyalkanoic acids - Google Patents

Detergent compositions containing salts of 4-hydroxyalkanoic acids Download PDF

Info

Publication number
US3821115A
US3821115A US00308204A US30820472A US3821115A US 3821115 A US3821115 A US 3821115A US 00308204 A US00308204 A US 00308204A US 30820472 A US30820472 A US 30820472A US 3821115 A US3821115 A US 3821115A
Authority
US
United States
Prior art keywords
detergent
sodium
composition
acid
hydroxyalkanoic
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
US00308204A
Other languages
English (en)
Inventor
V Lamberti
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
Original Assignee
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 US00308204A priority Critical patent/US3821115A/en
Priority to CH1896672A priority patent/CH569787A5/xx
Priority to AT1109872A priority patent/AT322075B/de
Priority to SE7217221A priority patent/SE400309B/xx
Priority to NL7300004A priority patent/NL7300004A/xx
Priority to NO737A priority patent/NO140475C/no
Priority to CA160,369A priority patent/CA985597A/en
Priority to GB33373A priority patent/GB1377716A/en
Application granted granted Critical
Publication of US3821115A publication Critical patent/US3821115A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C11D1/04—Carboxylic acids or salts thereof

Definitions

  • ABSTRACT Low scum-forming detergent compositions are afforded when salts of C to C 4-hydroxyalkanoic acids are employed as the sole detergent active or in combination with another surface active agent.
  • soaps of certain hydroxystearic acids are not particularly adaptable to laundry detergents when used alone.
  • U.S. Pat. No. 3,305,488 discloses that soaps of and 12- hydroxystearic acid are relatively poor detergents.
  • Another object of the present invention is to provide detergent compositions containing soaps which are more readily biodegradable than soaps derived from naturally occurring fatty acids.
  • one mode of the invention is the use of salts of C to C 4hydroxyalkanoic acid alone; another mode and the mostpreferred is the use of a combination of an anionic, nonionic, zwitterionic or ampholytic detergent compound with a salt of C to C 4-hydroxyalkanoic acid.
  • the formulations utilizing.
  • C to C 4-hydroxyalkanoates are especially useful in hot water washing (about 5090C) wherein the self-dispersing properties are most pronounced.
  • the lower chain lengths are more useful at lower temperatures (about
  • the present invention relates to detergent compositions wherein salt of a C to C 4-hydroxyalkanoic acid is used as the sole detergent active-compound or a salt of a C to C 4-hydroxyalkanoic acid is combined with another detergent compound.
  • detergent compositions of the present j invention comprise: I Y
  • the 4-hydroxyalkanoates used in the present invention are preferably the alkali metal salts of the 4- hydroxyalkanoic acids, although the ammonium and substituted ammonium salts such as the mono-, diand tri-ethanolammonium, tetramethyl ammonium, methyl ammonium and morpholinium salts of the aforementioned'acid are also suitable.
  • the salts of mixtures of the C to C C to C C to C18 C to C and C to C 4-hydroxyalkanoic acids are especially suitable for use in this invention. Also included in the above mentioned mixtures are the 4-hydroxyalkanoic acids containing odd numbered carbon chains, for example C C and C When the 4-hydroxyalkanoates are used as the sole detergent active, f they. are preferably present in an 3' 1 amount ranging from about 40 to about 90% or may even comprise 100% of the detergent composition.
  • the amount present will vary from about 5% to about 60% by weight of the detergent composition.
  • the detergent composition will usually comprise from about 5 to about 60%, preferably about to about 30% of such additional detergent compound.
  • the particular type of organic detergent compound additionally employed in the detergent compositions of the present invention is not important. For example, anionic organic soap and non-soap detergent compounds may be used.
  • alkali metal salts of organic sulfuric reaction products having in their molecular structure an alkyl radical'and a radical selected from the group consisting of sulfonic and sulfuric acid ester radicals; sodium or potassium alkyl benzene sulfonates in which the'alkyl group contains from about nine to about carbon atoms and in which the alkyl group is attached to the benzene ring in either the 1 position or the secondary position as well as many other well known to those skilled in the art and as disclosed in US. Pat. No. 3,519,570 incorporated by reference herein.
  • the nonionic detergent compounds that may be employed in the present invention are those that do not ionize in water and include the polyethylene oxide condensates of alkyl phenols containing six-l2 carbons in the alkyl group, the condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine, the condensation products of random secondary alcohols derived from C -C n-paraffins with ethylene oxide and the condensation products of aliphatic (Cg-1g) alcohols with ethylene oxide as more fully described in US. Pat. No. 3,519,570.
  • ampholytic detergent compounds contemplated in the present invention can be broadly described as derivatives of aliphatic secondary and tertiary amines, in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about eight to 18 carbon atomsand one contains an anionic water solubilizing group.
  • Examples of compounds falling within this definition are sodium 3-dodecylaminopropionate and sodium 3- tetradecylaminopropanesulfonate and sodium N-2- hydroxyhexadecyl-N -methyl-taurate.
  • the zwitterionic detergent compounds which can be used can be broadly described as. derivatives of aliphatic quaternary ammonium compounds, sulfonium compounds and phosphonium compounds in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about eight to 18 carbon atoms and one contains an anionic water solubilizing group.
  • Examples of compounds falling within this definition are 3-(N,N-dimethyl-N- hexadecylammonio)propanel -sulfonate, 3-( N,N- dimethyl-N-hexadecylammonio)-2-hydroxypropanelsulfonate, 3-(dodecylmethylsulfonium)propane sulfonate, and 3-(cetyl-methylphosphonium)ethane sulfonate.
  • detergent adjuvants include such components as well-known soil suspending agents, hydrotropes, corrosion inhibitors, dyes, perfumes, fillers such as sodium sulfate, buffers such as sodium silicates and carbonate, optical brighteners, bleaches, such as perborates, percarbonates, organic and inorganic chlorine releasing agents, bleach activators, enzymes, detergent boosters and solvents, suds boosters, suds depressants, lime-soap dispersants, germicides, fungicides, anti-tamishing agents, cationic detergents, fabric softening agents and in the case of liquid compositions, opacifiers and organic solvents.
  • any of the conventional well-known detergent builders phosphate and non-phosphate type
  • the detergent compositions of the present invention may be in any of the usual physical forms for such compositions such as powders, beads, flakes, bars, tablets, noodles, liquids, pastes and the like.
  • the detergent compositions are prepared and utilized in the conventional manner.
  • Table 1 illustrates the superior results obtained when soiled test cloths are washed with a detergent composition employing sodium 4-hydroxystearate as the sole detergent active.
  • the detergent formulation was not only equal or superior to a standard detergent formulation containing an anionic detergent compound but did not form a scum and/or undispersed particles as did the compositions containing sodium Z-hydroxyand sodium l2-hydroxystearate.
  • Table 2 illustrates the results obtained when soiled test cloths are washed with a detergent composition comprising sodium 4-hydroxystearate and an additional detergent active.
  • Table 3 illustrates the results obtained when soiled test cloths are washed at F and F with a detergent composition comprising either sodium 4- hydroxytetradecanoate, sodium 4- hydroxyhexadecanoate or sodium 4- hydroxyoctadecanoate and an additional detergent active namely LAS.
  • Table 4 illustrates the results obtained when soiled test cloths are washed with a detergent composition employing either sodium 4-hydroxytetradecanoate, sodium 4-hydroxyhexadecanoate and sodium 4- hydroxyoctadecanoate as the sole detergent active.
  • the detergent formulations set forth in Tables 1-4 were prepared by blending together the recited components and tested for detergency or cleansing ability in the Terg-O-Tometer Test using 65% Dacron 35% cotton VCD (vacuum cleaner dust) cloth as the test cloth and the washing conditions as noted. The pH of the washing solutions were adjusted,-where necessary, to pH 10 by the addition of caustic thereto.
  • the average detergency units (DU) of the formulations is the final reflectance of the washed cloth minus the initial reflectance of the soiled cloth (the average '5 of two runs), the reflectance being measured with a QQFQBQFA EQHEQQQQ QK Di fcrsnse M ter.
  • LAS is an anionic detergent compound which is sodium linear secondary alkyl (C -C secondary benzene sulfonate
  • Neodol 45-11 is a nonionic detergent compound which is an adduct of a modified Oxo type C -C alcohol with an average of 11 moles of ethylene oxide
  • C C HAMT is an ampholytic detergent compound which is sodium N-2- hydroxy C -C alkyl-N-methyltaurate
  • Sulfobetaine DCH is a zwitterionic detergent compound which is cocodimethylsulfopropyl betaine
  • Sodium Tripolyphosphate is pentasodium tripolyphosphate
  • Sodium Silicate Solids is a water soluble silicate having a SiO 2205 99.
  • the sodium 4-hydroxystearate employed in the compositions of the present invention is a known compound and is prepared by saponification of v-stearolactone which, in turn, may be prepared according to Example of US. Pat. No. 3,054,804.
  • the other 4- hydroxyalkanoates are readily prepared by. saponification of the corresponding methyl esters or lactones of the 4-hydroxyalkanoic acids which are prepared according to a modification of the method of Lardelli et al., Rec. des Trav. Chim. des Pays-Bas, 86, 481 (1967).
  • thod for preparing the homologous 5 hydroxyalkanoic acids is modified by utilizing succinic anhydride in place of glutaric anhydride in the Cason synthetic scheme described on pages 494-495 in the reference.
  • succinic anhydride in place of glutaric anhydride in the Cason synthetic scheme described on pages 494-495 in the reference.
  • the methyl esters of the intermediate 4-oxoalkanoic acids are isolated as solids, reduced with sodium borohydride in methanol/ether to the corresponding hydroxy compounds, which after isolation by acidification and ether extraction, are saponified with alcoholic sodium hydroxide or potassium hydroxide to yield the desired sodium or potassium 4-hydroxyalkanoate.
  • the ammonium and substituted ammonium salts are prepared by neutralization of the desired 4- hydroxyalkanoic acid with a stoichiometric amount of ammonium hydroxide or the desired organic amine or substituted ammonium hydroxide in alcoholic solution followed by evaporation of the solvent.
  • the free 4- hydroxyalkanoic acids are obtained by acidification of an aqueous solution or dispersion of the alkali metal salt of the 4-hydroxyalkanoic acid, extraction of the liberated hydroxy acid with ether and evaporation of the ether layer.
  • Table 1 Component Formulation (7r) 1. Sodium 2-Hydroxystearate 2. Sodium 4-Hydroxystearate 3. Sodium IZ-Hydroxystearate 75 4.- Sodium linear secondary alkyl 18 (Clll
  • methyl 4-oxohexadecanoate is prepared from 4.86g of Mg, 49.8g of dodecyl bromide, l9.6g of CdCl and 30. lg of l3-carbomethoxypr0pionyl chloride. Yield: 27.0g; b.p. ll5ll7C/0.08mm.
  • Methyl 4-oxohexadecanoate 27.0g is saponified by dissolving in 50g of 3A ethyl alcohol and reacting with a solution of 4.2g of sodium hydroxide dissolved in 70g of 3A ethyl alcohol. After standing for two days, the precipated product is filtered, washed with ethanol followed by ether and then air dried. Yield: 26g of sodium 4-oxohexadecanoate.
  • 4-hydroxyhexadecanoic acid 208g is dissolved in 60ml of 3A ethyl alcohol and neutralized with a soluwith 3A ethyl alcohol and dried in a vacuum oven. Yield of sodium 4-hydroxyhexadecanoate, 20.4g analyzing 98.4% active by titration with standard perchloric acid in acetic acid.
  • sodium 4- hydroxytetradecanoate, sodium 4- hydroxyoctadecanoate and sodium 4-elcosan0ate are readily prepared from the appropriate alkyl bromide.
  • potassium hydroxide in place of sodium hydroxide in the final neutralization steps, the corresponding potassium salts are readily obtained.
  • a detergent composition comprising, as components, based on the total weight of said composition, about a. 5 to about of a salt of a C to C 4-hydroxyalkanoic acid and mixtures thereof, the cation of said salt is selected from the group consisting of alkali metal, ammonium and substituted ammonium,
  • a detergent compound selected from the group consisting of anionic, nonionic, zwitterionic, or ampholytic detergent compounds and mixtures thereof, and
  • composition of claim 1 wherein said detergent composition consists essentially of a. 5 to about 90% of said salt of C to C 4-hydroxyalkanoic acid, and
  • composition of claim 1 wherein the 4- hydroxyalkanoic acid is 4-hydroxyhexadecanoic acid.
  • composition of claim 1 wherein the 4- hydroxyalkanoic acid is 4-hydroxyoctadecanoic acid.
  • composition of claim 1 wherein the 4- hydroxyalkanoic acid is 4-hydroxyeicosanic acid.
  • composition of claim 1 wherein said detergent compound is present in an amount ranging from about 5 to about 60%.

Landscapes

  • 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)
US00308204A 1972-01-03 1972-11-20 Detergent compositions containing salts of 4-hydroxyalkanoic acids Expired - Lifetime US3821115A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US00308204A US3821115A (en) 1972-01-03 1972-11-20 Detergent compositions containing salts of 4-hydroxyalkanoic acids
CH1896672A CH569787A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1972-01-03 1972-12-28
AT1109872A AT322075B (de) 1972-01-03 1972-12-28 Wasch- und reinigungsmittelzusammensetzungen
SE7217221A SE400309B (sv) 1972-01-03 1972-12-29 Detergentkomposition innehallande organiskt, detergentaktivt emne
NL7300004A NL7300004A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1972-01-03 1973-01-02
NO737A NO140475C (no) 1972-01-03 1973-01-02 Vaskemiddelblanding.
CA160,369A CA985597A (en) 1972-01-03 1973-01-02 Detergent compositions
GB33373A GB1377716A (en) 1972-01-03 1973-01-03 Detergent compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US21508972A 1972-01-03 1972-01-03
US00308204A US3821115A (en) 1972-01-03 1972-11-20 Detergent compositions containing salts of 4-hydroxyalkanoic acids

Publications (1)

Publication Number Publication Date
US3821115A true US3821115A (en) 1974-06-28

Family

ID=26909687

Family Applications (1)

Application Number Title Priority Date Filing Date
US00308204A Expired - Lifetime US3821115A (en) 1972-01-03 1972-11-20 Detergent compositions containing salts of 4-hydroxyalkanoic acids

Country Status (8)

Country Link
US (1) US3821115A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) AT322075B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA985597A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH569787A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1377716A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL7300004A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO140475C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
SE (1) SE400309B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4179392A (en) * 1970-12-21 1979-12-18 Mobil Oil Corporation Biodegradable hard water detergents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8800763D0 (en) * 1988-01-14 1988-02-17 Unilever Plc Detergent compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4179392A (en) * 1970-12-21 1979-12-18 Mobil Oil Corporation Biodegradable hard water detergents

Also Published As

Publication number Publication date
AT322075B (de) 1975-05-12
NL7300004A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-07-05
NO140475B (no) 1979-05-28
CA985597A (en) 1976-03-16
GB1377716A (en) 1974-12-18
CH569787A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1975-11-28
NO140475C (no) 1979-09-05
SE400309B (sv) 1978-03-20

Similar Documents

Publication Publication Date Title
US3843563A (en) Detergent compositions
AU622396B2 (en) Built detergent compositions containing diethyleneglycoliminodiacetic acid
AU596244B2 (en) Aqueous detergent compositions containing diethyleneglycol monohexyl ether solvent
EP0213729B1 (en) Detergent compositions
EP0054325B1 (en) Detergent composition with reduced soil-redeposition effect
US3341459A (en) Detergent compositions
US3957661A (en) Fabric softening laundry detergent containing organic esters of phosphoric acid
US4021376A (en) Detergent compositions with nonphosphate builders containing two or more carboxyl groups
US3336233A (en) Built detergent compositions containing 3-hydroxyalkyl alkyl sulfoxides
CA1052220A (en) Detergent composition
US4325829A (en) Detergent compositions
JPH06501282A (ja) 液体洗剤組成物
US3821115A (en) Detergent compositions containing salts of 4-hydroxyalkanoic acids
US4198308A (en) Manufacture of free-flowing fabric softening detergent
US4049585A (en) Detergent compositions containing internal vicinal disulfates
US3853779A (en) Low foaming detergent compositions
US3767584A (en) Lime soap dispersants and compositions containing them
EP0042188B1 (en) Detergent composition containing low levels of amine oxides
US4040781A (en) Novel 2-(alkylsulfinyl)ethyl sulfates and compositions employing same
US3729432A (en) Detergent builder composition
CA1100381A (en) Liquid detergent compositions
NO131603B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
US3560391A (en) Detergent compositions containing phosphonio carboxylates
US3915879A (en) Detergent compositions
JPS63273699A (ja) 洗剤組成物