US2204433A - Detergent - Google Patents

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Publication number
US2204433A
US2204433A US2204433DA US2204433A US 2204433 A US2204433 A US 2204433A US 2204433D A US2204433D A US 2204433DA US 2204433 A US2204433 A US 2204433A
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US
United States
Prior art keywords
glycerine
product
fatty acid
new
acid
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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
    • 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
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols

Definitions

  • i wetting agents, detergents and the like are a
  • the material that is used in place of glycerine l series of compounds which consist of glycerine, is beta methyl glycerine monochlorhydrin, which "one hydroxy group of which has been replaced by may be derived from isobutylene, which in turn a sulphate group,' and another hydroxy group of may come from petroleum. It is well known that which has been'replaced by a fatty acid radical beta methyl glycerine may be made from isoconnected to the glycerine molecule through an butylene, the product being converted, in the Q0 ester linkage.
  • a new H'SOlM type of compound which is gen- '35 erally similar to the type of compounds men-
  • OOCR indicates a fatty acid tioned above, but which differs somewhat in radical which may be either saturated or units constitution and properties and possesses the saturated, and preferably has between 5 and 21' particular advantage of being mp y and easily carbon atoms in it, and M represents any suitmaterials.
  • menmetaL glycerme is an essential mgtedient'
  • the sulphonate, Glycenne is a relatively expensive raw hydmxy and fatty acid radicals may not always miter 1a] f i a gffig gz gg gii z attach to the beta methyl glycerine' molecule in a m figgfi fi underessuch the same relative positions as those in which they are now shown, but may interchange their 'cumstances" it is ig i' :3 if positions with'one another To indicate this in of glycerine be avo e e pa on men one I W .EiiiEE-ffi 233i;z.ititiifafii iiiiiilli n dric ale 0 su ars, or e e, e su .s
  • the preferred method of making the new type of composition consists in reacting beta. methyl glycerine monochlorhydrin with an'aqueous solution of a suitable sulphite, such as sodium sulphite or ammonium sulphite.
  • a suitable sulphite such as sodium sulphite or ammonium sulphite.
  • the best results have been obtained by heating these latter reactants, with agitation, at 175 C. to 225 C. for a period ranging from 4 to 15 hours.
  • the progress of the reaction is assisted by reducing the pressure so as to remove as much of the water as possible during the later stages of the reaction.
  • the sodium salt of dihydroxy methyl propane sulphonic acid may be formed as describedlabove or by any other method and finally converted into the ultimate product by reaction with a fatty acid halide.
  • the reaction takes place at a somewhat lower temperature, namely, from 75 C. to 125 C.
  • the remaining halogen acid willbe neutralized before any attempt is made to isolate I the final product.
  • Still another way of making the same type'of product is by forming a soluble salt of a halogen hydroxy methyl propane sulphonic acid by partially sulphonating a beta methyl glycerine dichlorhydrin and thereafter reacting the neutralized sulphonate with an alkali salt of a fatty
  • the products made by the methods given are not entirely pure, and usually contain a considerable quantity-of inorganic or organic sulphates or. chlorides formed by the neutralization of excess acid or acid freed in the reactions, but they may be used for many of the purposes for which they are intended in the state in which they are prepared. Further purification maybe effected by crystallization of the impure product from alcohol.
  • cocoanut oil fatty acid chloride was added to 40.5 parts by weight (0.25 mole) of the dry sodium salt of beta methyl glycerine alphasulphonic acid and the mixture heated at 100 C. to 120 C. with agitation for eight hours. At the end of this time the product was neutralized with caustic soda and purified as in the first example.
  • a foam test was made on samples of the material :produced by each of the methods mensoap treating equipment.
  • a wetting test was also conducted by placing a piece of unwashed filter cloth in 100 cc. of a 1% aqueous solution of the new materialin a 250 cc. beaker. The piece of filter cloth was carefully dropped into the liquid so as to lie flatly on the surface of the solution. At the end of 18 seconds the cloth was completelywet and sank to the bottom. Under similar conditions the glycerine product mentioned above sank in about the'same time.
  • the new materials may be used for deterging andwetting and for numerous purposes. They may be formed into beads, bars, flakes, chips, powders, or any other forms in which soap is ordinarily found, by the usual This is important. particularly, the ability of the product to form beads and bars, for by no means all sulphated or sulphonated materials can be prepared in these forms and the forms have, by extensive use in the soap industry, proved themselves to be highly.
  • emulsions may be made by incorporating the new materials in mixtures of oleaginous and aqueousmaterials, with, of course, sufficient agitation and other treatment to disperse one of the phases into the other.
  • a a new composition of matter a chemical compound consisting of beta methyl glycerine, one'hydroxy group of which has been esterified by a long-chain fatty acid and another hydroxy group of which has been replaced by a sulphonate radical.
  • R is an alkyl radical having from 4 to 20 carbon atoms
  • M is a cation of the group consisting of sodium, potassium, calcium, ammonium and trietl'ranolammonium.
  • a process of forming a chemical compound that comprises reacting upon beta. methyl glycerine monochlorhydrin with sodium sulphite and condensing the resultant product with a I long chain fatty acid.
  • a process of forming a new chemical compound that comprises converting beta methyl glycerine monochlorhydrin into a salt of dihydroxy methyl propane sulphonic acid and condensing the-said sulphonic acid salt with a long chain i'atty'acid halide.
  • a process of forming a chemical compound that comprises converting beta methyl glycerine dichlo'rhydrin into 'a. soluble salt of a halogen hydroxy methyl propane sulphonicacid and condensing said sulphonic acid salt with an ,alkali metal salt of a long chain fatty acid.

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)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US2204433D 1938-01-18 Detergent Expired - Lifetime US2204433A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18562238A 1938-01-18 1938-01-18

Publications (1)

Publication Number Publication Date
US2204433A true US2204433A (en) 1940-06-11

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ID=22681758

Family Applications (1)

Application Number Title Priority Date Filing Date
US2204433D Expired - Lifetime US2204433A (en) 1938-01-18 Detergent

Country Status (3)

Country Link
US (1) US2204433A (enrdf_load_stackoverflow)
FR (1) FR837370A (enrdf_load_stackoverflow)
GB (1) GB514053A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2635103A (en) * 1950-03-09 1953-04-14 Drew & Co Inc E F Detergent and method of making the same
US4832876A (en) * 1987-09-14 1989-05-23 Colgate-Palmolive Company Process for the manufacture of higher fatty monoglyceride monosulfate detergents
US4950440A (en) * 1987-09-14 1990-08-21 Colgate-Palmolive Company Process for the manufacture of high fatty acid monoglyceride monosulfate detergents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2427576A (en) * 1945-02-22 1947-09-16 Colgate Palmolive Peet Co Ether sulphonates and their production

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2635103A (en) * 1950-03-09 1953-04-14 Drew & Co Inc E F Detergent and method of making the same
US4832876A (en) * 1987-09-14 1989-05-23 Colgate-Palmolive Company Process for the manufacture of higher fatty monoglyceride monosulfate detergents
US4950440A (en) * 1987-09-14 1990-08-21 Colgate-Palmolive Company Process for the manufacture of high fatty acid monoglyceride monosulfate detergents

Also Published As

Publication number Publication date
FR837370A (enrdf_load_stackoverflow) 1939-02-08
GB514053A (enrdf_load_stackoverflow) 1939-10-30

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