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
  • C11D1/37—Mixtures of compounds all of which are anionic
• • 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
• • 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
  • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols

Definitions

• a detergent composition is formulated that is relatively calcium insensitive and can effectively be used with many builders.
• the detergent composition consists essentially of the water-soluble salts of from 40% to 55% alkene-lsulfonate, from 20% to 40% 2-alkoxy alkane-l-sulfonate with the alkoxy radical containing from one to four carbon atoms, from 10% to 20% of 3- and 4-h'ydroxy alkane-l-s-ulfonate and from 2% to alkene disulfonate all by percentage weight.
• the carbon chain lengths of the above sulfonates are all from 10 to carbon atoms long.
• a preferred built detergent composition consists essentially of the above detergent composition and a builder salt in the ratio of detergent to builder of from 10:] to 1:10.
• This invention relates to novel detergent compositions which offer excellent overall performance characteristics. It also relates to built detergent compositions. The built detergent compositions are useful in light-duty and heavyduty cleaning situations.
• Light-duty applications are those such as the hand washing of dishes and lightly soiled fine fabrics which fabrics cannot as a rule withstand the vigorous treatment of machine laundering. Also, light-duty washing situations are those which generally call for a gentle washing action in cool or lukewarm water. It is well known by those skilled in the art that compositions designed for such uses must have certain performance properties which distinguish them from heavy-duty cleaning compositions. For instance, they must be mild to the skin, possess high sudsing properties, and also possess cleaning power in water solutions having cool or lukewarm temperatures, e.g., below 100 F.
• heavy-duty applications are those cleaning situations in which heavily soiled articles are encountered. Considerations in such cleaning processes inice clude the use of vigorous mechanical action usually in hot water having temperatures below about F. up to about 200 F. Moreover, the problems presented by high soil loads or fabrics such as cotton are unlike those dealt with in light-duty situations. As a result, heavyduty detergent compositions must be specially formulated.
• whiteness maintenance is a term which is used to measure the ability of an aqueous solution of a detergent composition to keep suspended in the solution, soil which has been removed during the washing process.
• Sequestrant builder salts such as sodium tripolyphosphate (STP) are normally included in built detergent compositions partly for the purpose of sequestering hardness ions, especially calcium, that are found in water.
• STP sodium tripolyphosphate
• a water-insoluble hardness ion salt of the detergent is often formed. This water-insoluble salt will be deposited on the laundered fabrics and as a result, will adversely affect the overall cleaning performance of the detergent.
• Recent fears of the effect of ST P and other phosphorous-containing sequestrant builders on the ecology have caused a great amount of research in the area of finding a suitable replacement.
• the novel detergent would be relatively calcium insensitive, i.e. would not form a water-insoluble salt with the calcium found in the water. In this way the detergent could be used in a heavy-duty application without the need of a builder or with builders considered to have weak sequestering properties. Unfortunately, the complex nature of how a detergent ,works has made the search for an effective detergent very difficult.
• Another object is to provide a built detergent composition containing an active detergent ingredient and a builder ingredient which provides excellent performance results when used in a washing solution having a temperature which can be between about 50 F. up to about 200 F.
• Still another object is to provide a less expensive, more efiicient built detergent composition than the best commercially available compositions.
• a still further object of this invention is to formulate a detergent composition that when used in combination with a builder possessing weak sequestering properties results in a built detergent composition that performs efficiently.
• the above detergent composition can form part of a built detergent composition consisting essentially of the detergent above noted and a builder salt in a detergent to builder ratio of from 10:1 to 1: l0.
• the present invention relates to a novel detergent composition.
• the detergent composition consists essentially of the water-soluble salts of from 40% to 55% alkene-1- sulfonate, from 20% to 40% 2-alkoxy alkane-l-sulfonate, from 10% to 20% of 3- and 4-hydroxy alkane-l-sulfonate, and from 2% to 15% alkene disulfonate having the parameters as set out more fully hereinafter.
• the components of the present detergent composition are produced either individually and thereafter combined in the prescribed proportions or are produced concurrently by the process described in commonly assigned concurrently filed herewith copending patent application Ser. No. 188,590, entitled Process for the Preparation of Sulfonated Detergent Composition by Herbert C. Smitherman.
• Preferred percentage ranges by weight for the water-soluble salts of this invention are from 40% to 45% alkene-1- sulfonate, from 30% to 40% 2-alkoxy alkane-l-sulfonate, from 10% to 15% 3- and 4-hydroxy alkane-l-sulfonate, and from 2% to 8% alkene disulfonate.
• the total percentage of the 2-alkoxy and 3- and 4-hydroxy alkane-lsulfonates in this preferred composition is equal to or greater than the percentage of the alkene-l-sulfonate.
• substituted ammonium compounds are mono-, diand triethylammonium, mono-, diand trimethylammonium, and mono-, di-, and triethanolammoniurn. Others will be apparent to those skilled in the art.
• the preponderant proportion of the alkene-I-sulfonates of this invention have the double bond distributed between the terminal carbon atom on which the sulfonate radical is attached and the fifth carbon atom.
• minor amounts of other double-bond positional isomers Such minor amounts of alkene-l-sulfonates having the alkene double bond more internally than the fifth carbon atom, i.e. less than 10% by weight do not materially affect the detergent properties of the composition.
• the starting step for the synthesis is a reaction between a long chain epoxide and sodium bisulfite to produce a 2-hydroxy-1- sulfonate derivative of the particular long chain epoxide.
• This reaction product is condensed with PCl to prepare the aforementioned 2-chlorosulfonic acid derivative which in turn is reacted with sodium carbonate to yield an alphabetaunsaturated compound.
• This method is merely illustrative of one synethesis that can be used. Any other suitable method can be used.
• the other preferred alkene-l-sulfonates wherein the alkene double bond is located between the second and third, third and fourth, and four and fifth carbon atoms can be prepared by the thermal dehydration of hydroxy sulfonates. According to the reaction set out immediately below, the thermal dehydration of the sodium salt of 3- hydroxy-sulfonate results in the preparation of a reaction mixture containing alkene-l-sulfonates having the double bond located between the second-third and third-fourth carbon atoms.
• reaction mixture of alkene-l-sulfonates containing the alkene double bond located between the thirdfourth and fourth-fifth carbon atoms can be prepared by using a 4-hydroxy-sulfonates as the starting material.
• reaction product can be formulated directly into a detergent composition according to the present invention. They can be separated into pure forms, if desired, though not necessary.
• This compound can be prepared by the method described in US. Pat. 3,346,628. As described therein a straight chain alphaolefin is reacted with a sulfur trioxide/dioxane complex to form an acid mix which is subsequently reacted with an alcohol. The resultant compounds are then neutralized and subsequently isolated in the normal manner.
• the material obtained is a mixture of compounds, one of which is the 2-alkoxy alkane-l-sulfonate.
• This compound can be s p rated from the other comp unds by column chromatography.
• the above described method of obtaining the alkoxy compound is merely illustrative of one way of synthesizing the said compound.
• the alcohol used in the above reaction is a lower alcohol, i.e. an alcohol having from 1 to 4 carbon atoms. Examples of such alcohols are methanol, ethanol, n-propanol, isopropanol, n-butanol, and isobutanol.
• the preferred Z-alkoxy alkane-l-sulfonates of this invention are Z-methoxy and 2-ethoxy-a1kane-1- sulfonate wherein the alkane chain contains from to carbon atoms.
• the 3- and 4-hydroxy alkane-l-sulfonate component of the present detergent composition is a mixture of saturated aliphatic compounds. A minor amount of unsaturation can be included in this mixture but preponderantly the compounds are all saturated.
• the 3- and 4-hydroxy alkanel-sulfonates of this invention contain from 10 to 20 carbon atoms, have the sulfonate radical located on a terminal carbon atom, and have the hydroxy radical attached to the third or fourth carbon atom.
• the formula for 3-hydroxy alkane-l-sulfonate is RCH(OH)Cl-I CI-I SO M where R is a C alkyl group and M represents a salt-forming cation as described above with regard to the alkene-l-sulfonate.
• the 4-hydroxy alkane-l-sulfonate is, of course, similar to the immediately above described compound with the hydroxyl group attached to the fourth carbon atom from the sulfonate radical. It has been discovered that the situs of the hydroxyl group in the compounds is an especially important factor.
• the detergency properties of said detergent composition is decreased.
• the detergent composition of this invention can tolerate hyroxy alkane-l-sulfonates wherein the hydroxyl group is attached along the carbon chain at positions other than the 3- and 4-position provided such compounds do not constitute more than 10% of the hydroxy alltane-l-sulfonate component.
• the 3- and 4-hydroxy alkane-l-sulfonates can be prepared by the free radical addition of sodium bisulfite to the corresponding 3- or 4-hydroxy-l-olefin, respectively.
• the hydroxy olefin for use as the starting material in the preceeding free radical addition reaction can be prepared by well known organic-metallic reactions, e.g. involving an aldehyde and a Grignard reagent in which R and R are organic radicals and Y is a halogen.
• organic-metallic reactions e.g. involving an aldehyde and a Grignard reagent in which R and R are organic radicals and Y is a halogen.
• Grignard reagents can be used in the example above as well as other methods for producing the subject compounds.
• the water-soluble salt of alkene disulfonate of this invention has one sulfonate radical attached to the terminal carbon atom.
• the second sulfonate radical is attached to an internal carbon atom that is not more than three carbon atoms removed from the said terminal carbon. Minor amounts of compounds can be included in which the second sulfonate radical is more internally than the fourth carbon, provided they do not exceed 10% by weight of the disulfonate component of the instant composition.
• the carbon chain length of the alkene disulfonate is from 10 to 20. The cation of this compound is the same as above described in connection with the alkene-l-sulfonate.
• the alkene double bond of the disulfonates is preponderantly distributed between the terminal carbon atom and the seventh carbon atom. That is, less than 10% by weight of the alkene disulfonates have the double bond more internally than the seventh carbon atom.
• the alkene disulfonates as just described can be prepared by any of several known methods.
• the novel detergent composition of the present invention is useful per se as an excellent detergent.
• the carbon chain length of the alkene and alkane sulfonates contain from 10 to 20 carbon atoms. It is preferred, however, to have the compounds contain from 14 to 18 carbon atoms in the sulfonated alkene and alkane chains. It is not necessary that each of the compounds contain the same number of carbon atoms. Mixtures of different chain lengths can be used. It is only necessary that the number of carbon atoms in each alkene and alkane sulfonated chain be within the prescribed limits of 10 to 20 or preferably 14 to 18.
• alkene-l-sulfonate from to 55% alkene-l-sulfonate, 20% to 40% 2-alkoxy alkane-l-sulfonate, 10% to 20% 3- and 4-hydroxy alkanel-suifonate, and 2% to 15% alkene disulfonate makes up a very satisfactory detergent composition in the context of the instant invention.
• An alkene-l-sulfonate content greater than 55% results in a detergent having relatively poorer performance as does percentages of 2-alkoxy al kane-l-sulfonate below 20%, 3- and 4-hydroxy alkane-lsulfonate below 10% and alkene disulfonate above 15% and below 2%.
• Detergent compositions containing proportions greater than 40% 2-alkoxy alkane-l-sulfonate or 20% of the hydroxy alkane-l-sulfonates are not materially efiected in terms of detergency thereby. However, for purposes of cost considerations, the alkoxyand hydroxyalkane-l-sulfonate percentages are kept within the prescribed limits of this invention.
• the amounts by weight of the described components are as follows: from 40% to alkene-l-sulfonate;
• the amount of alkene-l-sulfonate is less than or equal to the total percentage of alkoxyand hydroxy-alkane-l-sulfonates in order to obtain eminently satisfactory detergency.
• Mixtures of the above compounds containing carbon chain lengths of 10 to 20 carbon atoms also perform eminently well as do other water-solubilizing salts thereof such as potassium, triethylammonium and triethanolammonium.
• anionic as well as nonionic, zwitterionic or ampholytic surfactants can be used in varying proportions with the detergent system of this invention.
• the detergent compositions of the present invention are especially useful in admixture with other materials to form complete formulations.
• Such complete formulations are prepared commercially in several forms including granular, flake, liquid, and tablet forms. More especially, the detergent compositions of the present invention are combined with water-soluble builder compounds to provide built detergent compositions.
• the weight ratio of builder to the detergent composition of this invention is from 10:1 to 1:10, preferably from 1:2 to 1:5.
• Suitable water-soluble, inorganic alkaline detergency builder salts are alkali metal carbonates, borates, phosphates, polyphosphates, bicarbonates, and silicates. Specific examples of such salts are sodium and potassium tetraborates, perborates, bicarbonates, carbonates, tripolyphosphates, pyrophosphates, orthophosphates and hexametaphosphates.
• Suitable organic alkaline detergency builder salts are: (1) water-soluble aminopolycarboxylates, e.g., sodium and potassium ethylenediaminetetraacetates, nitrilotriacetates and N-(2 hydroxyethyl) nitrilodiacetates; (2) water-soluble salts of phytic acid, e.g., sodium and potassium phytates-see US. Pat.
• watersoluble, polyphosphonates including specifically, sodium, potassium and lithium salts of ethane-l-hydroxy-Ll-diphosphonic acid, sodium, potassium and lithium salts of methylene diphosphonic acid, sodium, potassium and lithium salts of ethylene diphosphonic acid, and sodium, potassium and lithium salts of ethane-1,l,2-triphosphonic acid.
• Other examples include the alkali metal salts of ethane-Z-carboxy-1,1-diphosphonic acid, hydroxymethanediphosphonic acid, carbonyldiphosphonic acid, ethane-1- hydroxy-l,1,2-triphosphonic acid, ethane-2-hydroxy-l, l ,2-
• a detergent builder material comprising a water-soluble salt of a polymeric aliphatic polycarboxylic acid having the following structural relationships as to the position of the carboxylate groups and possessing the following prescribed physical characteristics: (a) a minimum molecular weight of about 350 calculated as to the acid form; (b) an equivalent weight of about 50 to about 80 calculated as to acid form; (c) at least 45 mole percent of the: monomeric species having at least two carboxyl radicals separated from each other by not more than two carbon atoms; (d) the site of attachment of the polymer chain of any carboxyl-containing radical being separated by not more than three carbon atoms along the polymer chain from the site of attachment of the next carboxyl-containing radical.
• compositions of this invention may contain adjuvants, diluents, and additives inclusive of germicidal agents, anti-tarnish agents, antiredeposition agents, bactericidal agents, dyes, and fluorescers without detracting from the advantageous proper ties of the composition.
• the built detergent compositions of Examples IV-VI perform well as a laundering composition exhibiting excellent soil removal and whiteness maintenance.
• the builder compounds found in Examples IV-VI above are illustrative of the many builders that can be used in combination with the detergent compositions of this invention.
• Builder compounds listed above in combination with the detergent compositions of this invention also give a satisfactorily built detergent composition.
• a detergent composition consisting essentially of:
• composition of claim 3 wherein the 2-a1koxy alkane-l-sulfonate has from 14 to 18 carbon atoms in the alkane chain and the alkene-l-sulfonate, 3- and 4-hydroxy alkane-l-sulfonates, and alkene disulfonate all contain from 14 to 18 carbon atoms.
• composition of claim 3 which consists essentially of from 40% to 45% of the alkene-l-sulfonate, from 30% to 40% of the 2-alkoxy alkane-l-sulfonate, from 10% to 15% of the 3- and 4-hydroxy alkane-l-sulfonates, and from 2% to 8% of the alkene disulfonate and wherein the total percentage of the 2-alkoxy and 3- and 4-hydroriy alkane-l-sulfonates is equal to or greater than the percentage of the alkene-l-sulfonate.
• a built detergent composition consisting essentially of the detergent composition of claim 1 and a builder in the weight ratio of detergent composition to builder of from 10:1 to 1:10.
• the built detergent composition of claim 9 wherein the builder is selected from the group consisting of the water-soluble salts of citric acid, benzene pentacarboxylic acid, and benzene hexacarboxylic acid.

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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)

Applications Claiming Priority (1)

Publications (1)

Family

ID=22693811

Family Applications (1)

Country Status (10)

Cited By (3)

• 0
  • BE BE789923D patent/BE789923A/xx unknown
• 1971
  • 1971-10-12 US US00188597A patent/US3729431A/en not_active Expired - Lifetime
• 1972
  • 1972-10-09 DE DE2249359A patent/DE2249359A1/de active Pending
  • 1972-10-10 CA CA153,557A patent/CA977236A/en not_active Expired
  • 1972-10-11 IT IT7230371A patent/IT968864B/it active
  • 1972-10-11 FR FR7236042A patent/FR2156269B1/fr not_active Expired
  • 1972-10-12 AU AU47678/72A patent/AU464670B2/en not_active Expired
  • 1972-10-12 GB GB4712672A patent/GB1367370A/en not_active Expired
  • 1972-10-12 NL NL7213831A patent/NL7213831A/xx not_active Application Discontinuation
  • 1972-10-12 JP JP47102295A patent/JPS4861510A/ja active Pending

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