US3759833A - Detergent compositions - Google Patents

Detergent compositions Download PDF

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Publication number
US3759833A
US3759833A US00213819A US3759833DA US3759833A US 3759833 A US3759833 A US 3759833A US 00213819 A US00213819 A US 00213819A US 3759833D A US3759833D A US 3759833DA US 3759833 A US3759833 A US 3759833A
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US
United States
Prior art keywords
detergent
sodium
alkyl
detergent composition
detergency
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Expired - Lifetime
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US00213819A
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English (en)
Inventor
D Easton
G Rennie
C Storer
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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
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring

Definitions

  • a detergent composition incorporates from 1 to 60% by weight of a water-soluble or water-dispersible salt of a heterocyclic dicarboxylic acid having the general formula:
  • HOOC coon wherein R can be hydrogen or a substituent such as bromine, chlorine, hydroxy, carboxy, C alkyl, amino or alkyl-substituted amino.
  • the salt acts as a detergency builder, and may act also as an inhibitor for the decomposition, caused by heavy-metal catalysis, of any peroxycompounds such as perborates, in the detergent composition.
  • the present invention relates to detergent compositions, and in particular to fabric-washing detergent compositions, incorporting detergency builders.
  • R is a hydrogen atom, a chlorine atom, a bromine atom, a hydroxyl group, an amino group, an alkyl-sub stituted amino group, a carboxyl group, or an alkyl group containing from 1 to 4 carbon atoms.
  • heterocyclic dicarboxylic acid salt a water-soluble or water-dispersible salt of a chemical compound of Formula I is referred to as a heterocyclic dicarboxylic acid salt.
  • heterocyclic dicarboxylic acid salts are known compounds.
  • the invention provides a detergent composition comprising a detergent-active compound and from about 1 to about 60% by weight of a heterocyclic dicarboxylic acid salt.
  • the heterocyclic dicarboxylic acid salt comprises from about 5 to about 60%, and particularly preferably from about 15 to about 55%, by Weight of the detergent composition.
  • R is an alkyl-substituted amino group
  • the preferred groups are N-methyl amino, N-ethyl amino, N,N- dimethyl amino and N,N-diethyl amino groups.
  • R is an alkyl group
  • methyl, ethyl and n-propyl groups are preferred.
  • R is a hydrogen atom, a hydroxyl group, an amino group, an alkyl-substituted amino-group,
  • R is a hydrogen atom or a hydroxyl group.
  • the heterocyclic dicarboxylic acid salt is preferably an alkali-metal salt, particularly a sodium salt, although potassium and lithium salts can be used. If desired, the heterocyclic dicarboxylic acid salt may be an ammonium or substituted ammonium salt.
  • heterocyclic dicarboxylic acid salt of the invention may still be obtained if a detergent composition incorporates the corresponding free heterocyclic dicarboxylic acid, or the heterocyclic dicarboxylic acid in a partially neutralised form, complete neutralisation of the heterocyclic dicarboxylic acid taking place when the detergent composition is dissolved in water.
  • heterocyclic dicarboxylic acid of Formula I above wherein R is a hydrogen atom is pyridine-2,6-dicarboxylic acid, which is known also as dipicolinic acid.
  • a detergent composition of the invention will contain at least one detergent-active compound.
  • the detergent-active content of the detergent composition will be from about 1 to about 50%, preferably from about 5 to 35%, and particularly preferably from about 10 to about 25%, by weight of the composition.
  • the nature of the detergent-active compound or compounds in the detergent composition is not an essential feature of the invention: any of the detergent-active compounds conventionally incorporated in or proposed for use in detergent compositions may be used, and those skilled in the art of formulating detergent compositions will be familiar with these detergent-active compounds and the various amounts and combinations in which they may advanta- Patented Sept. 18, 1973 Typical anionic detergent-active compounds are watersoluble or water-dispersible salts of various organic acids.
  • alkali-metals such as sodium and, less preferably, potassium
  • suitable organic acids are: 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 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),
  • 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 alkyl-phenol; condensates containing from about 40% to about 80% polyoxyethylene by weight and having a molecular weight of from about 5,000 to about 11,000 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.
  • 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 contains from about 8 to 18 carbon atoms and one contains an anionic water solubilising group, such as sodium 3 dodecylaminopropionate, sodium-3-dodecylaminopropanesulphonate and sodium N-Z-hydroxydodecyl-N-methyl-taurate.
  • anionic water solubilising group such as sodium 3 dodecylaminopropionate, sodium-3-dodecylaminopropanesulphonate and sodium N-Z-hydroxydodecyl-N-methyl-taurate.
  • 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 substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilising group, such as 3-(N,N-dimethyl-N-hexadecyl-ammonium) propane-l-sulphonate betaine, 3-(N,N-dimcthyl-N-hexadecyl ammonium)-2-hydroxypropane-l-sulphonate betaine, 3-(dodecylmethyl-sulphoniurn )propane- 1-sulphonate betaine, and 3-(cetylmethylphosphonium)ethane sulphonate betaine.
  • anionic water solubilising group such as 3-(N,N-dimethyl-N-hexadecy
  • the heterocyclic dicarboxylic acid salts of the invention may comprise the whole of the detergency builder content of a detergent composition of the invention. However, if desired, mixtures of one or more of these heterocyclic dicarboxylic acid salts with one or more known detergency builders may be used. As one of the objects of the invention is to provide an effective detergent composition containing either no phosphorus or at most only a low level of phosphorus, it is preferred that any such other detergency builders should not be phosphorus-containing compounds. Usually the total amount of detergency builders in a detergent composition of the invention will be from about 5 to about 70% by weight of the detergent composition.
  • detergency builders are known, and those skilled in the art of formulating fabricwashing detergent compositions will be familiar with these materials.
  • detergency builders are sodium tripolyphosphate; sodium orthophosphate; sodium pyrophosphate; sodium trimetaphosphate; sodium ethanel-hydroxy-1,1-diphosphonate; sodium carbonate; sodium silicate; sodium citrate; sodium oxydiacetate; sodium nitrilotriacetate; sodium ethylene-diaminetetraacetate; sodium salts of long-chain dicarboxylic acids, for instance straight chain (C to C succinic acids and malonic acids; sodium salts of alpha-sulphonated 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 these acids, and also from the copolymerisation of the above acids and anhydrides with minor amounts of other monomers, such as 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 detergent composition ingredients in any of the amounts in 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; chlorinereleasing 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, oolourants, 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 fluidisation 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.
  • Components Parts, percent Sodium dodecyl benzene sulphonate 18 Detergency builder 1 50 Alkaline sodium silicate Sodium sulphate 12 Fluorescers, perfumes, antiredeposition agents,
  • Components Parts, percent Sodium dodecyl benzene sulphonate 16 Detergency builder 1 50 Alkaline sodium silicate 8 Sodium sulphate, fluorescers, perfumes, antiredeposition agents, water, etc. to
  • Example 3 The monohydrate of 4-hydroxy-pyrldine-2,6- dlenrboxylic acid.
  • Example3 19 3 37 Comparative Example 0 13 23 31 These results show that the detergent powder of Example 3 had a greater detergency efiiciency than the conventional detergent powder of Comparative Example C.
  • Example 3 33 39 321 Comparative Example C 30 33 35
  • the results in Table III confirm the superiority of the detergent powder of Example 3 over that of Comparative Example C.
  • EXPERIMENT 3 This was the same as Experiment 1, except that the test cloth used was a commercially-available cottonbased test cloth (EMPA 101) supplied by the Swiss Materials Testing and Experimental Institute, Unterstrasse 11, 9001 Saint Gallen, Switzerland.
  • EMPA 101 commercially-available cottonbased test cloth supplied by the Swiss Materials Testing and Experimental Institute, Unterstrasse 11, 9001 Saint Gallen, Switzerland.
  • EXAMPLE 4 The ability of pyridine-2,6-dicarboxylic acid to act as an inhibitor for the decomposition of peroxy-compounds is illustrated by the following experiment.
  • test soluitons corresponded to 0.5% solutions a detergent composition containing 25% by weight of sodium perborate and various levels (from 0 up to 50% by weight) of pyridine-2,6-dicarboxylic acid.
  • test solution was heated from 20 C. up to C. over a period of one hour, and then maintained at 95 C. for a further 10 minutes. Subsequently, the percentage of sodium perborate lost was determined volumetrically using a potassium iodide titration. The following results were obtained.
  • a detergent composition comprising by weight:
  • a detergent composition according to claim 1, wherein said sodium salt comprises from about 5 to about 60% by weight of said detergent composition.
  • a detergent composition according to claim 2 which additionally comprises from about 1 to about 30% by weight of a peroxy-compound selected from the group consisting of sodium perborate and sodium percarbonate.
  • a detergent composition comprising by weight:
  • a detergent composition comprising by weight: References Cited (a) from about 5 to about 35% of a detcrgent -act1vc Chemical Abstracts VOL 54 p. 2212c.

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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)
US00213819A 1971-01-05 1971-12-29 Detergent compositions Expired - Lifetime US3759833A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB42271 1971-01-05
GB3763971 1971-08-11

Publications (1)

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US3759833A true US3759833A (en) 1973-09-18

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US00213819A Expired - Lifetime US3759833A (en) 1971-01-05 1971-12-29 Detergent compositions

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US (1) US3759833A (enrdf_load_stackoverflow)
JP (1) JPS5115845B1 (enrdf_load_stackoverflow)
AT (1) AT320106B (enrdf_load_stackoverflow)
AU (1) AU460957B2 (enrdf_load_stackoverflow)
BE (1) BE777735A (enrdf_load_stackoverflow)
CA (1) CA935732A (enrdf_load_stackoverflow)
CH (1) CH563451A5 (enrdf_load_stackoverflow)
DE (1) DE2165863B2 (enrdf_load_stackoverflow)
ES (1) ES398553A1 (enrdf_load_stackoverflow)
FR (1) FR2121568B1 (enrdf_load_stackoverflow)
GB (1) GB1342095A (enrdf_load_stackoverflow)
NL (1) NL7200084A (enrdf_load_stackoverflow)
SE (1) SE369198B (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956157A (en) * 1974-07-19 1976-05-11 W. R. Grace & Co. Detergent and bleaching agent comprising sodium perborate and sodium .alpha.β-glucoheptonate
US3966649A (en) * 1972-09-28 1976-06-29 Colgate-Palmolive Company Liquid detergents containing chelidamic acids and salts thereof
AU616558B2 (en) * 1988-09-07 1991-10-31 Unilever Plc Detergent compositions
US5069812A (en) * 1990-12-10 1991-12-03 Lever Brothers Company Bleach/builder precursors
WO1994005763A1 (en) * 1992-09-08 1994-03-17 Unilever N.V. Liquid automatic dishwashing composition
US5300657A (en) * 1992-12-07 1994-04-05 Lever Brothers Company, Division Of Conopco, Inc. Process for preparing chelidonic acid

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5653808U (enrdf_load_stackoverflow) * 1979-10-01 1981-05-12
GB8624050D0 (en) * 1986-10-07 1986-11-12 Unilever Plc Machine dishwashing compositions
CA2044947A1 (en) * 1990-06-22 1991-12-23 Stephen B. Kong Composition and method for fabric encrustation prevention
EP0634476B1 (en) * 1993-07-12 1999-10-13 The Procter & Gamble Company Stable aqueous emulsions of nonionic surfactants with a viscosity controlling agent
ATE190647T1 (de) * 1993-11-11 2000-04-15 Procter & Gamble Hypochloritbleichmittelzusammensetzung
KR102183400B1 (ko) * 2015-06-23 2020-11-26 주식회사 이엔에프테크놀로지 세정액 조성물

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966649A (en) * 1972-09-28 1976-06-29 Colgate-Palmolive Company Liquid detergents containing chelidamic acids and salts thereof
US3956157A (en) * 1974-07-19 1976-05-11 W. R. Grace & Co. Detergent and bleaching agent comprising sodium perborate and sodium .alpha.β-glucoheptonate
AU616558B2 (en) * 1988-09-07 1991-10-31 Unilever Plc Detergent compositions
US5069812A (en) * 1990-12-10 1991-12-03 Lever Brothers Company Bleach/builder precursors
WO1994005763A1 (en) * 1992-09-08 1994-03-17 Unilever N.V. Liquid automatic dishwashing composition
US5300657A (en) * 1992-12-07 1994-04-05 Lever Brothers Company, Division Of Conopco, Inc. Process for preparing chelidonic acid

Also Published As

Publication number Publication date
AU460957B2 (en) 1975-05-08
AU3756172A (en) 1973-07-05
BE777735A (fr) 1972-07-05
JPS5115845B1 (enrdf_load_stackoverflow) 1976-05-20
ES398553A1 (es) 1975-05-16
FR2121568A1 (enrdf_load_stackoverflow) 1972-08-25
CH563451A5 (enrdf_load_stackoverflow) 1975-06-30
GB1342095A (en) 1973-12-25
AT320106B (de) 1975-01-27
DE2165863A1 (de) 1972-07-20
FR2121568B1 (enrdf_load_stackoverflow) 1976-07-23
NL7200084A (enrdf_load_stackoverflow) 1972-07-07
DE2165863C3 (enrdf_load_stackoverflow) 1978-06-22
DE2165863B2 (de) 1977-10-27
CA935732A (en) 1973-10-23
SE369198B (enrdf_load_stackoverflow) 1974-08-12

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