US3663446A - Detergent compositions with thermo controlled foaming capacity - Google Patents

Detergent compositions with thermo controlled foaming capacity Download PDF

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Publication number
US3663446A
US3663446A US706445A US3663446DA US3663446A US 3663446 A US3663446 A US 3663446A US 706445 A US706445 A US 706445A US 3663446D A US3663446D A US 3663446DA US 3663446 A US3663446 A US 3663446A
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US
United States
Prior art keywords
detergent compositions
acids
sodium
temperatures
foam
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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
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US706445A
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English (en)
Inventor
Hans Barth
Wilhelm Griess
Martin Knausenberger
Henner Lange Hans-Udo Menz
Angelos Sagredos
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Lever Brothers Co
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Lever Brothers Co
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Publication date
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating 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
    • C11D3/2075—Carboxylic acids-salts thereof

Definitions

  • thermo-controller is a substance of the general formula in which R represents a carbon ring with, if desired, one or more double bonds, which may also be semicyclic; R and R are carbon chains, at least one of Which, preferably R is branched, and which are saturated or which may contain one or more double bonds, whereas R and R may also be zero.
  • the ring system R may also carry further substituents.
  • Z is a hydrogen atom or a salt-forming element or a salt-forming group.
  • Detergent compositions containing various active detergents, builders bleaching agents and optical brighteners are known. Efforts have been made to provide detergent compositions which are low-foaming at high temperatures, i.e. over about 90 0., but have acceptable foaming characteristics at temperatures of up to about 60 C. Such compositions would be very suitable for use in drum-type washing-machines, as over-foaming at higher temperatures would be avoided. It is known that this object can be attained to some extent if the formation of foam is suppressed by the addition of foam-reducing agents, such as liquid hydrocarbons or hydrocarbons that are solid at room temperature, e.g. parafiins or waxes. A drawback of these additives, however, is that they can adversely affect the detergency of the washing composition.
  • foam-reducing agents such as liquid hydrocarbons or hydrocarbons that are solid at room temperature, e.g. parafiins or waxes.
  • Foam suppression has also been obtained by incorporationg a proportion of soap in the detergent composition.
  • Compositions where soap is employed for this purpose generally contain about l030% by weight of anionic detergent, such as alkyl benzene sulphonate, alkyl sulphate, fatty alcohol sulphate and the like, as well as polyphosphate in about the same up to a fivefold amount.
  • anionic detergent such as alkyl benzene sulphonate, alkyl sulphate, fatty alcohol sulphate and the like
  • polyphosphate in about the same up to a fivefold amount.
  • detergents of this kind may include the alkylene oxide condensation products of alkyl alcohols, of alkylphenol, of polyoxypropylene, of fatty acid amide, and of other organic hydrophobic compounds.
  • Detergent compositions of this type the so-called mixed-active detergent compositions, further usually contain an oxygen-liberating bleaching agent, such as perborate, silicate and small quantities of optical brighteners and soil-suspending agents, such as carboxy methyl cellulose.
  • an oxygen-liberating bleaching agent such as perborate, silicate and small quantities of optical brighteners and soil-suspending agents, such as carboxy methyl cellulose.
  • the two side chains indicated above are preferably in 1,2-position to each other.
  • the number of carbon atoms inchain R may appropriately range from 0 to 1 6, preferably from 0 to 12, and that in chain R from 2 to 21, the total number of carbon atoms in both chains R and R ranging from 5 to 33, preferably from 10 to 20.
  • mixtures are preferred that contain not more than 10% by weight, advantageously less than 5% by weight, of constituents in which R; is zero.
  • Suitable branched compounds are those in which the branching in the carbon chain is not on the carbon atom directly connected to the ring, or if so, those having a cumene-like side chain structure of which the aliphatic chains comprise no further branching.
  • the cyclic compounds according to the above formula or their mixtures may be obtained in a known way by the Friedel-Crafts alkylation of benzene or alkylbenzene with unsaturated fatty acids in the presence of suitable catalysts.
  • the fatty acids used should have 3 to 22 carbon atoms and at least one double bond.
  • Useful catalysts are the Friedel-Crafts catalysts such as aluminium chloride, boron fluoride, etc.
  • the distillate was identified as a mixture of isomeric methyl phenyl stearic acids by analytical measurements made with the aid of gas chromatography, mass spectrometry and U.V.- and I.R.-spectroscopy.
  • the distillate was identified as a mixture of isomeric methyl phenyl undecanoic acids by analytical measurements.
  • methyl phenyl undecanoic acid 250 g. methyl phenyl undecanoic acid were subjected to catalytic hydrogenation in glacial acetic acid in the presence of 1.25 g. PtO in a one-litre autoclave at 180 200 C. and up to about 170 atm. for 13 hours.
  • the hydrogenated product was filtered off from the catalyst, freed of the acetic acid by washing out, and finally distilled under vacuum, whereby the main part of methyl cyclohexyl undecanoic acid (approx. 230 g.) distilled over between l80-192 C.
  • the distillate was established to be a mixture of isomeric methyl cyclohexyl undecanoic acids by analytical measurements.
  • distillate consisted of a mixture of isomeric isopropyl phenyl stearic acids.
  • the products thus obtained may or may not be subjected to total or partial hydrogenation.
  • the cyclic compounds used as detergent components according to the invention not only show the advantage, as was surprisingly found, of having a good foaming capacity at low temperatures and an effective foam suppression at elevated temperatures, but moreover they are excellent detergents, which are at least equal to the soaps usually incorporated in detergent compositions.
  • the foam-suppressing action at elevated temperatures provided by the cyclic substances used according to the invention is so good that in most cases the desired foamsuppressing at elevated temperatures can be achieved by substituting the substances of the invention for only part of the soap portion normally contained in such detergent compositions.
  • the substances according to the invention are therefore preferably introduced into these detergent compositions in such an amount that the soap component is replaced by the cyclic acids or their salts for 20-70%, in particular for about 45-55%.
  • Detergent compositions according to the invention may contain the usual additives, such as optical brighteners or other colorants, perborate stabilizers, perfume, etc.
  • cyclic carboxylic acids and their salts are not restricted to the washing of laundry, but they may also be advantageously applied in any other cleaning process in which it is desired that at elevated temperatures less foam is produced than in the low and medium temperature ranges.
  • compositions consisting essentially of from about to about 30% by weight of alkyl benzene sulphonate, and 1 to about 5 times of said amount of a polyphosphate builder, in which there is incorporated as a foam-controlling agent, a material selected from the group consisting of cyclic acids and sodium salts of such acids, said acids being a mixture of isomers having the formula:
  • RZCOOH wherein R is either a cyclohexyl or a benzene radical; R is an aliphatic hydrocarbon chain having from 0-16 carbon atoms, R; is a branched aliphatic hydrocarbon chain having from 2-21 carbon atoms; the total number of carbon atoms of R and R being from 5-33, wherein said foam-controlling agent is present in an amount effective to cause foam suppression of the detergent composition at high temperatures.
  • compositions according to claim 1 in which there is incorporated as a foam-controlling agent a material selected from the group consisting of cyclic acids and sodium salts of such acids, said acids being a mixture of isomers having the formula:
  • RzCOOH wherein R is either a cyclohexyl or a benzene radical; R and R are aliphatic hydrocarbon chains having a total number of carbon atoms of about between 10 and 20.
  • compositions according to claim 1 in which said cyclic acids are present in an amount not exceeding the amount of alkylbenzenesulphonate detergent, wherein said foam-controlling agent is present in an amount effective to cause fioam suppression of the detergent composition at high temperatures.

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US706445A 1966-09-23 1968-02-19 Detergent compositions with thermo controlled foaming capacity Expired - Lifetime US3663446A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEU0013106 1966-09-23
DEU0013590 1967-02-24

Publications (1)

Publication Number Publication Date
US3663446A true US3663446A (en) 1972-05-16

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ID=26001112

Family Applications (2)

Application Number Title Priority Date Filing Date
US706445A Expired - Lifetime US3663446A (en) 1966-09-23 1968-02-19 Detergent compositions with thermo controlled foaming capacity
US84454A Expired - Lifetime US3706675A (en) 1966-09-23 1970-10-27 Detergent composition with thermo-controlled foaming capacity

Family Applications After (1)

Application Number Title Priority Date Filing Date
US84454A Expired - Lifetime US3706675A (en) 1966-09-23 1970-10-27 Detergent composition with thermo-controlled foaming capacity

Country Status (7)

Country Link
US (2) US3663446A (xx)
BE (1) BE704212A (xx)
FR (1) FR1548455A (xx)
GB (1) GB1205945A (xx)
LU (1) LU54520A1 (xx)
NL (1) NL143987B (xx)
SE (1) SE356069B (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1492938A (en) * 1974-01-11 1977-11-23 Procter & Gamble Ltd Low sudsing detergent compositions

Also Published As

Publication number Publication date
SE356069B (xx) 1973-05-14
NL143987B (nl) 1974-11-15
NL6713026A (xx) 1968-03-25
FR1548455A (xx) 1968-12-06
US3706675A (en) 1972-12-19
DE1617210B2 (de) 1975-02-20
LU54520A1 (xx) 1969-06-24
DE1617210A1 (de) 1970-10-01
GB1205945A (en) 1970-09-23
BE704212A (xx) 1968-03-22

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