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
  • C11D1/88—Ampholytes; Electroneutral compounds
  • C11D1/92—Sulfobetaines ; Sulfitobetaines
• • 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
  • C11D10/00—Compositions of detergents, not provided for by one single preceding group
  • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
• • 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
  • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides

Definitions

• compositions comprising higher fatty acid soaps and the alkylbenzyl di-lower alkylammonio alkane-l sulfonates are described. Desirable results are obtained When the ratio of soap to zwitterionic, by weight, is from 3:1 to 100:1.
• This invention relates to alkylbenzyl di-lower alkyl ammonio alkane sulfonates, and to soap-based detergent compositions containing them.
• Detergent compositions based on conventional watersoluble soaps have many desirable properties, which render them at least highly competitive with detergent compositions based on other organic detergents. However, they have the well known failing that in hard water insoluble soaps are formed, and these tend to flocculate, especially in the conditions of the rinse, to form what is often known as lime scum. This tends to be deposited either on fabrics which have been washed, where in effect it constitutes dirt, or on the vessels in which the washing and rinsing is carried out, for example as deposits. on washing machines, or as bath tub ring.
• the new compounds are alkylbenzyl di-lower alkylammonio alkane-l sulfonates and have the formula:
• R wherein R is a straight or branched chain alkyl group having 8 to 24, preferably 10 to 18 carbon atoms; R is an alkyl group having 1 to 6 carbon atoms; R is an alkyl group having 1 to 6 carbon atoms; and n is an integer of from 1 to 4, preferably 2 or 3.
• the invention also embraces detergent compositions comprising water-soluble soap and a compound as. defined above.
• the zwitterionic compounds are those where R and R are each methyl or ethyl radicals. It is preferred to use those compounds wherein R is straightchained.
• the zwitterionic compounds can be based on alkylbenzene mixtures, such as most commercial detergent alkylates, which contain a mixture of alkyl benzenes of mean chain length within the above ranges.
• the zwitterionic compounds of the invention can be conveniently made.
• One method is to form the alkylbenzyl chloride, e.g., by reaction in acetic acid of an alkylbenzene with formaldehyde and hydrogen chloride in the presence of zinc chloride, and to treat this compound with the appropriate dialkylamine to form the alkylbenzyl dialkylamine.
• the resulting tertiary amine can be reacted for instance with a halo-alkane sulfonate, typically Cl (CH SO Na where n has the meaning defined above, or, for the compounds where n is 3 or 4, with propaneor butane sultone.
• a halo-alkane sulfonate typically Cl (CH SO Na where n has the meaning defined above, or, for the compounds where n is 3 or 4, with propaneor butane sultone.
• Other preparative routes will occur to those skilled in the art and may be selected on grounds of convenience or economic advantage. For instance, it may be preferred to attach the alkane sulfonate group to the amino nitrogen and thereafter attach the alkylbenzyl radical.
• the water-soluble soaps which can be used in the detergent compositions of the invention are the higher fatty acid soaps normally used for washing, for instance the alkali metal, especially sodium or potassium, salts of fatty acids having from 8 to 24, especially 10 to 18 carbon atoms.
• the soaps can be made by direct saponification of natural oils and fats, such as tallow, palm oil, lard, greases, coconut or palm kernel oils and many others, or they can be made by neutralization of fatty acids derived from such oils and fats or from those made synthetically or derived from petroleum and like sources. Soaps from natural oils and fats, or from fatty acids derived from them, will be predominantly straight-chained.
• the synthetic fatty acids or those from petroleum sources can be straightor branch-chained.
• Preferred soaps are those made from mixtures of tallow, grease or palm oils to provide the longer chain, e.g., C fatty acid residues and coconut or palm kernel oil to provide shorter chain, e.g., C
• the zwitterionic compounds of the invention can be present in any proportion relative to soap effective to provide lime soap-dispersing properties, but are normally present in relatively small proportions. Desirable results are obtained when the ratio of soap to zwitterionic, by weight, is from 3 :l to :1, especially from 10:1 to 20: 1.
• the lime soap-dispersing properties of the zwitterionic compounds of the invention can be employed to advantage by adding the compounds to a wash liquor, before or when the soap is added or before the washing process is begun.
• the zwitterionic compounds are incorporated into a soap composition, which can be a solid, granular, in bar form or a liquid. Mixtures of the zwitterionic compounds of the invention can be suitably employed.
• An alkaline builder salt can be included.
• the new compounds are particularly valuable as a component of granular soap products, especially built soap powders intended primarily for washing clothes. Such products can contain, in addition to the soap and zwitterionic compound, water-soluble alkaline builder salts.
• Suitable builder salts include alkali metal silicates, carbonates, phosphates and polyphosphates, borax, organic sequestering agents such as sodium nitrilotriacetate, ethane-l-hydroxy-l, 1- diphosphonates, and the like.
• Bleaching agents such as sodium perborate or percarbonate can be present.
• Minor components such as dyes, perfumes, soil-suspending agents such as carboxymethyl cellulose, enzymes, tarnish inhibitors, dust-suppressing agents, stabilizers for the bleaching agents and/or the enzymes and the like can also be employed.
• EXAMPLE H Scum dispersant effect A 1 /2% solution of soap in soft water was prepared, and arrangements provided so that air could be bubbled through it to form foam, which was carried over by the air current into a vessel containing hard (515 parts per EXAMPLE HI 1.9% solutions of soap in de-ionized water were prepared, containing in addition quantities of 3-(dodecy1 benzyl dimethylammonio) propane-l-sulfonate (C sultaine) and of 3 (nonylbenzyl dimethylammonio) propane-l-sulfonate (C sultaine). Each solution was placed in a water bath to maintain its temperautre at 55 C. and nitrogen was bubbled through at a fixed rate.
• the foam formed was carried over for a set time into a vessel containing hard (515 parts per million as CaCO water, wherein the foam was quenched.
• the water was 4 poured through a weighed 200 mesh BSS sieve, and the fiocculated lime soaps retained determined, after drying, by re-weighing the sieve. Results obtained were:
• Composition B consisted of 95.2 parts of Composipared consisting of:
• a composition B consisted of 95.2 parts of Composition A and 4.8 parts of 3-(dodecylbenzyl dimethylammonio) propane-l-sulfonate, derived from commerical linear dodecylbenzene. Solutions of these compositions of concentration 0.25% by weight, were made up in hard water (256 parts per million hardness as CaCO in a Hoover Mark III washing machine and agitated for 30 seconds at 54 C. The agitator was stopped and after 30 seconds a black perspex plate was dipped into the solution for 5 seconds and withdrawn through any scum present on the surface of the liquid. The plate was examined visually for adherent scum. The solutions of Composition A left visible scum on the black plates, while those of Composition B left no scum.
• a zwitterionic surface active compound having the formula:
• R and R are FOREIGN PATENTS each methyl 01' ethyl. 5 4 19 1 2 0 5 7 N 6.
• R is a straight- 5333 34 gagi g 260 513 N chained alkyl having 12 carbon atoms; R and R are 1:084:739 9/1967 Great Britain 260 501 13 each methyl; and n 15 5 1,087,415 10/1967 Great Britain 260-50113 References Cited LEON ZITVER, Primary Examiner UNITED STATES PATENTS M. W. GLYNN, Assistant Examiner 2,129,264 9/1938 Downing et a1.

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)

Applications Claiming Priority (3)

Publications (1)

Family

ID=27260036

Family Applications (2)

Family Applications After (1)

Country Status (8)

Cited By (5)

Families Citing this family (2)

• 0
  • BE BE756880D patent/BE756880A/xx unknown
• 1969
  • 1969-10-01 GB GB48278/69A patent/GB1274005A/en not_active Expired
• 1970
  • 1970-09-22 US US74496A patent/US3660470A/en not_active Expired - Lifetime
  • 1970-09-29 NL NL7014280A patent/NL7014280A/xx unknown
  • 1970-09-30 DE DE19702048066 patent/DE2048066A1/de active Pending
  • 1970-09-30 AT AT1044572A patent/AT314054B/de not_active IP Right Cessation
  • 1970-09-30 AT AT884970A patent/AT320612B/de not_active IP Right Cessation
  • 1970-09-30 FR FR7035386A patent/FR2062828A5/fr not_active Expired
  • 1970-10-01 CH CH1457370D patent/CH543490A/de not_active IP Right Cessation
• 1972
  • 1972-02-14 US US00226346A patent/US3767584A/en not_active Expired - Lifetime

Also Published As

Similar Documents