US3915879A - Detergent compositions - Google Patents

Detergent compositions Download PDF

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Publication number
US3915879A
US3915879A US458264A US45826474A US3915879A US 3915879 A US3915879 A US 3915879A US 458264 A US458264 A US 458264A US 45826474 A US45826474 A US 45826474A US 3915879 A US3915879 A US 3915879A
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Prior art keywords
sodium
carbon atoms
detergent
alkyl
detergent compositions
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US458264A
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English (en)
Inventor
Philip John Barnett
Winston Michael Fox
Thomas Mcgee
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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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • 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
    • C11D3/001—Softening 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates

Definitions

  • the present invention relates to detergent compositions adapted for use in fabric washing and which contain chemical compounds which act as detergency builders and fabric softeners.
  • the invention also relates to novel chemical compounds for use in such detergent compositions.
  • Detergent compositions adapted for use in fabric washing, particularly when such washing is to be conducted in domestic fabric washing machines generally comprise as major ingredients detergentactive compounds and detergency builders.
  • the most commonly used detergency builders are the condensed phosphates, particularly sodium tripolyphosphate, but the use of other inorganic and organic materials, such as sodium nitrilotriacetate and sodium ethane-l-hydroxyl,l-diphosphonate, has been proposed.
  • Another important feature of a fabric washing detergent composition is its ability to impart a soft feel to fabric articles.
  • the majority of conventional fabric washing detergent compositions do not alleviate the harshening of fabric articles caused by repeated washes which, in the case of articles of clothing, may make the fabric articles less comfortable to have in contact with the human skin.
  • a detergent composition comprises at least one detergent-active compound and at least one olycarboxylic acid derivative, or a watersoluble or water-dispersible salt thereof, having the general formula:
  • R is a substantially linear primary or secondary alkyl or substantially linear primary or secondary alkenyl chain containing on average from 14 to 20, preferably 16 to 18, carbon atoms
  • n is l to 4, preferably 1 or 2
  • m is 2 to 5, preferably 2 or 3
  • the cyclic ring may be fully or partially saturated. or fully aromatic, (n m) not being greater than 6.
  • the cyclic ring of the olycarboxylic acid derivative is fully aromatic, and the polycarboxylic acid derivative accordingly has the general formula:
  • Polycarboxylic acid derivatives of the invention may be incorporated in a detergent composition either in the form of a partial free acid or as a water-soluble or water-dispersible salt thereof.
  • Alkali-metal, particuarly sodium and potassium, salts are preferred, but other salts such as ammonium or substituted ammonium. c.g. trimethylammonium and triethylammonium. may be used if desired.
  • the polycarboxylic acid derivatives of the invention will normally comprise from about 5 to about by weight of a detergent composition, preferably from about 15 to about 50% by weight.
  • Particularly preferred polycarboxylic acid derivatives of the invention are:
  • R is a substantially linear primary or secondary alkyl chain containing on average from 16 to 18 carbon atoms.
  • the aromatic polycarboxylic acid partial esters may be prepared by reacting appropriate molar amounts of an aromatic polycarboxylic acid, or an anhydride thereof, with a long-chain aliphatic alcohol. In some instances transesterification may be required.
  • the techniques associated with esterification and transesterification are familiar to those skilled in the synthesis of organic chemical compounds. The Examples given below illustrate in detail typical methods suitable for the preparation of the aromatic polycarboxylic acid derivatives of the invention.
  • detergentactive compound or compounds in a detergent composition of the invention is not a critical feature and any of the detergent-active compounds conventionally used in fabric washing detergent compositions may be utilised.
  • Those skilled in the art of formulating detergent compositions will be familiar with these detergentactive compounds and the various amounts and combinations in which they may advantageously be used.
  • the detergent-active compound or compounds may be anionic, nonionic, amphoteric or zwitterionic in character.
  • the detergent-active compound content of the detergent composition of the invention will be from about 1 to about 50%, preferably from about 2 to 35%, and particularly preferably from about 5 to about by weight of the detergent composition.
  • Typical anionic detergent-active compounds are water-soluble or water-dispersible salts of various organic acids.
  • the cations of such salts are generaly alkali-metals, such as sodium and, less preferably, potassium, but other cations, such as ammonium and substituted ammonium, can be used if desired.
  • alkyl benzene sulphonic acids the alkyl chains of which contain from about 8 to about 20 carbon atoms, such as p-dodecyl benzene sulphonic acid and linear alkyl (C -C15) benzene sulphonic acid; the mixtures of sulphonic acids obtained by reacting linear and branched olefins, particularly linear cracked-wax or Ziegler" alpha-olefins, containing from about 8 to about 22 carbon atoms, with sulphur trioxide; alkyl sulphonic acids obtained by reacting alkanes containing from about 8 to about 22 carbon atoms with sulphur dioxide/oxygen or sulphur dioxide/chlorine (followed by hydrolysis in the latter case), or by the addition of bisulphite to olefins, particularly linear cracked-wax or Ziegler alpha-olefins, containing from about 8 to about 22 carbon
  • nonionic detergent-active compounds are: condensates of alkyl-phenols having an alkyl group (derived, for example, from polymerised propylene, diisobutylene, octene, dodecene or nonene) containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with about 5 to 25 moles of ethylene oxide per mole of alkylphenol; condensates containing from about 40% to about polyoxyethylene by weight and having a molecular weight of from about 5,000 to about 1 1,000 resulting from the reaction of ethylene oxide with the reaction product of ethylenediamine and excess propylene oxide; condensates of linear or branched-chain aliphatic alcohols containing from 8 to 18 carbon atoms with ethylene oxide, e.g.
  • R R R N long-chain tertiary amine oxides corresponding to the general formula R R R N 0, wherein R 1 is an alkyl radical containing from about 8 to 18 carbon atoms and R and R 3 are each methyl, ethyl or hydroxy ethyl radicals, such as dimethyldodecylamine oxide, dimethyloctylamine oxide, dimethylhexadecylamine oxide and N-bis (hydroxyethyl) dodecylamine oxide; long-chain tertiary phosphine oxides corresponding to the general formula RRR"P 0, wherein R is an alkyl, alkenyl or monohydroxyalkyl radical containing from 10 to 18 carbon atoms and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms, such as dimethyldodecylphosphine oxide, dimethyl
  • RRS 1 2hydroxypropylmethyltetradecylphosphine oxide, dimethyloleylphosphine oxide and dimethyl-2-hydroxydodecylphosphine oxide; and dialkyl sulphoxides corresponding to the general formula RRS 0, wherein R is an alkyl, alkenyl, betaor gamma-monohydroxyalkyl radical or an alkyl or betaor gamma-monohydroxyalkyl radical containing one or two other oxygen atoms in the chain, the R groups containing from 10 to l8 carbon atoms and wherein R is a methyl, ethyl or alkylol radical, such as dodecyl methyl sulphoxide, tetradecyl methyl sulphoxide, 3-hydroxytridecyl methyl sulphoxide, 2-
  • sodium-3-dodecylaminopropanesulphonate 5 hydroxydodecyl methyl sulphoxide, 3-hydroxy-4- dodecyloxybutyl methyl sulphoxide, 2-hydroxy-3- decyloxypropyl methyl sulphoxide, dodecyl ethyl sulphoxide, Z-hydroxydodecyl ethyl sulphoxide and dodecyl-Z-hydroxyethyl sulphoxide.
  • amphoteric detergent-active compounds are: 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 conatins from about 8 to 18 carbon atoms and one contains an anionic water solubilising group, such as sodium-3-dodecylaminopropionate,
  • Suitable zwitterionic detergent-active compounds are: derivatives of aliphatic quaternary ammonium compounds, sulphonium compounds and phosphonium compounds in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substitutents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilising group, such as 3-(N,N-dimethyl-N-hexadecylammonium) propane-l-sulphonate betaine, 3-(N,N- dimethyl-N-hexadecyl-ammonium)-2-hydroxypropane-l-sulphonate betaine 3-(dodecylmethyl-sulphonium) propane-l-sulphonate betaine, and 3-(cetylmethylphosphonium) ethane sulphonate betaine.
  • anionic water solubilising group such as 3-(N,N-dimethyl-N-hexadecylammonium) propane-
  • a polycarboxylic acid derivative of the invention may be utilised as the sole detergency builder in a (15.1,
  • tergent composition or if desired may be used in combination with one or more known detergency builders.
  • polycarboxylic acid derivative may be used as a partial replacement for sodium tripolyphosphate in an otherwise conventional sodium tripolyphosphate-containing detergent composition.
  • the amount of such other detergency builders will not be more than about 20%, and preferably not more than by weight of the detergent composition.
  • detergency builders are known, and those skilled in the art of formulating fabric-washing detergent compositions will be familair with these materials.
  • detergency builders are sodium tripolyphosphate; sodium orthophosphate; sodium pyrophosphate; sodium trimetaphosphate; sodium ethanel-hydroxy-l, l-diphosphonate; sodium carbonate; sodium silicate; sodium citrate; sodium oxydiacetate; sodium carboxymethyloxysuccinate; sodium nitrilotriacetate; sodium ethylene-diaminetetraacetate; sodium salts of long-chain dicarboxylic acids, for instance straight chain (C to C alkyl or alkenyl succinic acids and malonic acids; sodium slats of alpha-sulo ROH +/EI HOOC phonated long-chain monocarboxylic acids; sodium salts of polycarboxylic acids; i.e.
  • acids derived from the polymerisation or copolymerisation of unsaturated carboxylic acids and unsaturated carboxy acid anhydrides such as maleic acid, acrylic acid, itaconic acid, methacrylic acid, crotonic acid and aconitic acid, and the anhydrides of certain of these acids, and also from the copolymerisation of the above acids and anhydrides with minor amounts of other monomers, such as ethylene, vinyl methyl ether, vinyl chloride, vinyl acetate, methyl methacrylate, methyl acrylate and styrene; and modified starches such as starches oxidised, for example using sodium hypochlorite, in which some anhydroglucose units have been opened to give dicarboxyl units.
  • a detergent composition of the invention may contain any of the'conventional fabric-washing detergent composition ingredients in any of the amountsin which such conventional ingredients are usually employed therein.
  • additional ingredients are lather boosters, such as coconut monoethanolamide and palm kernel monoethanolamide; lather controllers; inorganic salts such as sodium sulphate and magnesium sulphate; oxygen-releasing bleaching agents such as sodium perborate, sodium percarbonate, and peracid bleach precursors such as tetraacetyl ethylene diamine; chlorine-releasing bleaching agents such as trichloroisocyanuric acid and sodium and potassium dichloroisocyanurates; antiredeposition agents, such as sodium carboxymethylcellulose; and, usually present only in minor amounts, perfumes, colourants, fluorescers, corrosion inhibitors, germicides and enzymes.
  • a detergent composition of the invention can be prepared using any of the conventional manufacturing techniques commonly used or proposed for the preparation of detergent compositions, such as slurry-making followed by spray-drying or spray-cooling, and subsequent dry-dosing of sensitive ingredients not suitable for incorporation prior to the drying step.
  • Other conventional techniques such as noodling, granulation, and mixing by fuidisation in a fluidised bed, may be utilised as and when necessary. Such techniques are familiar to those skilled in the art of detergent composition manufacture.
  • a detergent composition of the invention may be prepared in any of the common physical forms associated with detergent compositions, such as powders, flakes, granules, noodles, cakes, bars and, in some cases, liquids.
  • R is a tallow group
  • the alcohol (XV; 1 mole) and the hemimellitic acid (XVI; 4 moles) were refluxed in toluene in the presence of concentrated sulphuric acid, water formed during the reaction being collected in a Dean and Stark apparatus.
  • the mole ratio of alcohol: acid was chosen to give a maximum probability of forming the desired mono-ester; a higher proportion of alcohol would have favoured an increased yield of (Ii-esters, etc.
  • the refluxing was continued until no further moisture was collected in the Dean and Stark apparatus.
  • the toluene was removed using a rotary evaporator, and the ester, and residual unreacted alcohol, were separated from the unreacted acid by methanol extraction using a Soxhlet extractor.
  • the ester (XVII) was crystallised from the methanol.
  • Ditallow pyromellitale (Ex: 4 4O 3U l.
  • a detergent composition compr sing I Tallow trimellitate a. from l50% by weight of an anionic, a nonIonIc, an amphoteric, a zwitterionic organic detergent ac- In the form at sodium salLs. 'tive compound or a mixture thereof, and b. from 5-60% by weight of a polycarboxylic acid de rivative of the following general formula
  • Each composition was used to wash artificially soiled 40 cotton test cloths in a Terg-O-Tometer apparatus, using (COXR 30l-l hard water (CazMg ratio 2:1) at 95C for 30 minutes at a product concentration of 0.6%, followed by a cold rinse. After drying the test cloths were ranked for softness by a panel, and were used in a photometric determination of the detergency produced by each composition. The following results were obtained:
  • composition according to claim 1 wherein n 1, R is a substantially linear primary or secondary alkyl chain with 16-18 carbon atoms, and m 2.
  • composition according to claim 1 wherein X 0, n 2, m 2 and R is a substantially linear primary or secondary alkyl chain with 16-18 carbon atoms.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US458264A 1973-04-10 1974-04-05 Detergent compositions Expired - Lifetime US3915879A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4071476A (en) * 1974-01-28 1978-01-31 Texaco Inc. Detergent builders and composition containing the same
US4863636A (en) * 1988-02-12 1989-09-05 American Cyanamid Company Substituted N-hydroxyphthalimides and their use as detergent additives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4379886A (en) 1980-04-28 1983-04-12 E. I. Du Pont De Nemours And Company Liquid coating composition having a reactive catalyst
DE59610828D1 (de) * 1995-05-18 2004-01-08 Textil Color Ag Sevelen Zusammensetzung zum Waschen und Reinigen von Textilmaterialien

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3692684A (en) * 1969-10-01 1972-09-19 Valter Sven Erwin Hentschel Detergent
US3844982A (en) * 1969-11-24 1974-10-29 Procter & Gamble Built detergent composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3692684A (en) * 1969-10-01 1972-09-19 Valter Sven Erwin Hentschel Detergent
US3844982A (en) * 1969-11-24 1974-10-29 Procter & Gamble Built detergent composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4071476A (en) * 1974-01-28 1978-01-31 Texaco Inc. Detergent builders and composition containing the same
US4863636A (en) * 1988-02-12 1989-09-05 American Cyanamid Company Substituted N-hydroxyphthalimides and their use as detergent additives

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DE2417556A1 (de) 1974-10-31
FR2225512B3 (https=) 1977-02-11
FR2225512A1 (https=) 1974-11-08

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