US3700607A - Detergent compositions containing n-oxide-aminocarboxylates - Google Patents

Detergent compositions containing n-oxide-aminocarboxylates Download PDF

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US3700607A
US3700607A US880977A US3700607DA US3700607A US 3700607 A US3700607 A US 3700607A US 880977 A US880977 A US 880977A US 3700607D A US3700607D A US 3700607DA US 3700607 A US3700607 A US 3700607A
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salt
carbon atoms
softening
sodium
oxide
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Bjorn Sundby
Edward J Kenney
Harold E Wixon
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Colgate Palmolive Co
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Colgate Palmolive Co
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates 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
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D3/001—Softening compositions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Definitions

  • R is an aliphatic hydrocarbon radical of 4 to 20 carbon atoms
  • R is a hydrocarbon radical of 1 to 7 carbon atoms or is R COOX
  • R is a divalent aliphatic or aromatic hydrocarbon radical of 1 to 9 carbon atoms, which may be the same as or different from any other R radical in the compound
  • X is hydrogen,alkali metal, alkaline earth metal, other suitable salt-forming metal, ammonium, alkylamine or alkanolamine, which may be the same as or different from any other X in the formula
  • m is from /3 to 1
  • n is from 1 to 3, both m and n being dependent on the valence(s) of X.
  • compositions comprise an inorganic builder salt, such as sodium tripolyphosphate or potassium pyrophosphate, and also may include other adjuvant materials, such as trisodium nitrilotriacetate, enzymes, anti-rede'position agents, bleaches or bluing agents, germicides, hydrotropes, auxiliary detergents and softening agents, etc.
  • an inorganic builder salt such as sodium tripolyphosphate or potassium pyrophosphate
  • other adjuvant materials such as trisodium nitrilotriacetate, enzymes, anti-rede'position agents, bleaches or bluing agents, germicides, hydrotropes, auxiliary detergents and softening agents, etc.
  • the aminocarboxylate comprises from 3 to 30% of the composition and the inorganic builder is from 10 to 70% thereof.
  • the products made may be in liquid or solid form, and are preferably employed as liquids or powders. They may be utilized as washing-softening agents in laundering or may be employed in pre-soaking or after-soaking of laundry, to improve the softening of the washed material.
  • the aminocarboxylate may be used without inorganic builder salt, in which cases it normally functions primarily as a softening agent and is preferably utilized after completion of washing.
  • This invention relates to compositions and processes for the treatment of textiles, clothing or laundry to clean and soften them and to impart anti-static properties to them.
  • the invented compositions and processes incorporate or utilize N-oxide-amino-carboxylates and are particularly adaptable to treatments of cotton and cotton-containing -materials, although they are useful for application to other natural and synthetic materials, too.
  • N- oxideaaminocarboxylates are exceptionally substantive to fabrics and a sufiicient proportion thereof remains on a fabric so as to make it soft and in many cases, to impart an anti-static effect. This action is especially surprising because the active ingredients themselves are detergents and serve to remove materials from substrates, rather than to deposit them thereon.
  • compositions and methods include their usefulness in hard and soft waters, and at high and low washing temperatures.
  • eflfective detergency, softness and anti-static properties are obtained under such conditions.
  • the compounds are genfoam which is not clogging" in a automatic washing machine.
  • the processes may be used in conjunction with many other treatments of textiles or laundry and'the compositions may be modified to include other detergents and adjuvants, without interfering 'with the desirable activities thereof.
  • built synthetic organic detergent compositions comprise an inorganic builder salt and an oxide of an aminocarboxylate or aminocarboxylic acid of the formula:
  • R is an aliphatic hydrocarbon radical of 4 to 20 carbon atoms
  • R is an aliphatic or aromatic vhydrocarbon radical of 1 to 7 carbon atoms or is R C0OX
  • R is a divalent aliphatic or aromatic hydrocarbon radicalof 1 to 9 carbon atoms, which may 'be the same as or different from any other
  • X is hydrogen, alkali, metal, alkaline earth metal, other suitable salt-forming metal, ammonium, al-kylamine or alkanolamine, which may be the same as or different from any other X in the formula
  • m is from /3 to 1
  • n is from 1 to 3, both m and n being dependent on the valence(s) of X.
  • the aminocarv boxylate comprises from 3 to 30% of the composition and the inorganic builder is from to 70% thereof.
  • Adjuvants may also be included, to contribute their special 1 properties.
  • I built synthetic organic detergent compositions mentioned 'above are employed as washing-softening agents in laundering textiles, clothing or other items, or in pre-soaking or' after-soa'king of such materials, to improve the 'softness oranti-static properties thereof.
  • Such processes also include use, of the aminocarboxylate without the presence I of inorganic builder salt.
  • both Xs and R s are both equal to 1.
  • Xs and R s are both alkali metal, ammonium, mono-, di- 'or tri-alkylamine, or mono-, dior tri-alkanolamine, and m and n are both equal to 1.
  • Xs and R s it is preferred for both Xs and R s to be the same, if more than one should be present.
  • the preferred compounds mentioned are found to be excellent textile softeners in .the compositions of this invention and in the processes thereof, especially for cotton articles washed with them, even after washing in the presence of the strong builders and other adjuvants and after normal rinsing.
  • the most preferred compounds are the salts of N-(Z-hydroxy-higher alkyl)-N-methyl glycineN- oxides and the N-(Z-hydroxy-higher alkyl)-iminodiacetic acidN-oxides, wherein the higher alkyl is of 12 to 16 carbon atoms and is of straight chain structure.
  • the sodium and potassium salts it is preferred to employ the sodium and potassium salts, with the sodium salt being that which is most useful.
  • the iminodiacetic acid compounds and the .N -methyl glycine compounds mentioned the more effective inthese compositions and; processes for the softening of cotton textiles are the N-methyl glycine oxides.
  • compositions and methods within the scope of the present invention utilize other such .compounds within the scope of the invention and the formula previously given.
  • Such other compounds may .possess useful properties as surfaces active agents, wetting agents, emulsifiers, detergents and anti-static agent, although they might not also produce to the same extent the extremely desirable softening activities shown by the most preferred compositions and methods, and could, in some cases, be considered to be ineffective in this respect.
  • N- Z-hydroxyhexadecyl) -N-ethyl glycine-N-oxide tri-
  • the alkyl groups of the N-(Z-hydroxyalkyl) portions of the above compounds, unless otherwise indicated, are the preferred straight chain groups, terminally joined to the nitrogen atom.
  • R branched chain materials may also be used.
  • the various alkyl groups formed from propylene may be employed, such as the propylene tetramer and pentamer, a preferred form of which is a mixture averaging 13 carbon atoms.
  • saturated hydrocarbons are preferred, those which are unsaturated, to the extent of one or two double bonds per radical, may also function as R R usually is a short chain material, preferably unsubstituted, and is most preferably methyl.
  • the product obtained does not have the desirable detersive and softening properties of the compoundsof this invention and is difiicult to manufacture.
  • R is preferably a short chain alkylene, usually of l to 2 carbon atoms, but it has been found that-lon er chain alkylenes. and even divalent hydrocarbyl aromatic compounds make useful products.
  • X while it may be hydrogen, is preferably a salt-forming ion. This is so because the salt is usually more stable and freer flowing and the built detergent compositions of the present invention are usually alkaline.
  • the salt-forming ions those which are monovalent are preferred because of their generally greater water solubility, an important feature in the present compositions and processes. However, even in those cases wherein solubility might be low, the compositions of this invention may be employed in other polar media and may even be useful in aqueous media, usually by including therein a hydrotrope or cosolvent.
  • novel compounds of this invention may be prepared by oxidation of the corresponding amine.
  • the N-(Z-hydroxyalkyl)-aminocarboxylic acid or iminodicarboxylic acid or salt thereof may be treated with an oxidizing agent, such as hydrogen peroxide or ozone, prefer-- ably in aqueous solution, and the Water remaining after the reaction may be removed by any suitable technique, e.g., freeze drying.
  • the reaction will be run in an aqueous solution of a soluble salt of the starting material and will be conducted by slowly admixing the oxidizing agent with the solution of salt at a temperature about .room temperature, with cooling to maintain such temperature or one slightly higher sometimes being desirable because of the exothermic reaction and generation of excess heat. Cooling will be most useful when there is present a high concentration of amine to be oxidized. Normally, the addition of the oxidizing agent will take place within a period of from 30 seconds to one hour, at a temperature of 15 to 50 C.
  • the solution may be held for an additional 30 minutes to 18 hours at a temperature of 40 to 90 C., to decompose excess H but this can also be done with catalysts, such as platinum or palladium, or with reducing agents, such as sodium sulfite.
  • catalysts such as platinum or palladium
  • reducing agents such as sodium sulfite.
  • the proportions of reactants employed are such that the oxidizing agent is initially present in excess. Such excess will usually be from 5% to 100% of the stoichiometric proportion, so as to aid in forcing the reaction and producing a 100% yield of the oxide. Of course, less than the stoichiometric proportion of oxidizing agent may be used, in which cases yields will suffer.
  • the stoichiometric quantity of oxidizing agent it is normally not desirable to use less than 75% of the stoichiometric quantity of oxidizing agent, unless it is desired to make a mixture of theoxide or salt and the unoxidized aminocarboxylic acid or iminodicarboxylic acid or salt.
  • a comparable reaction may be run with the acid, which may be solubilized by suitable solvents, e.g., ketones, such as acetone, methyl ethyl ketone.
  • the salts may be made by subsequent treatment of the acid oxides produced with alkaline material, e.g., NaOH, triethanolamine.
  • alkaline material e.g., NaOH, triethanolamine.
  • the acid forms of the oxide may be produced by acidification of previously manufactured salts.
  • N-(Z-hydroxyalkyl)-substituted aminocarboxylic acid or the corresponding -iminodicarboxylic acid starting materials or salts may be made by reactions similar to those described in our co-pending applications entitled N-(2- Hydroxy-Higher Hydrocarbyl) N Lower Hydrocarbyl- Aminocarboxylates and N-(Z-Hydroxyhydrocarbyl) Iminodicarboxylates, filed on the same day as this application. In brief, such reactions are of the N-substituted aminocarboxylic acid with hydrocarbon-1,2-epoxide.
  • Such reactions are usually conducted at an elevated temperature, often about the boiling point of the reaction mixtures, which may contain some water, and after the reaction has been completed, which may take from minutes to 5 hours, the reaction mix is cooled and water is removed by any suitable technique. Such removal may be by freeze drying, flash vaporization, evaporation or other method. To remove impurities, the product may be extracted with a solvent for these, e.g., acetone. If desired, it may recrystallized from alcohol.
  • a solvent for these e.g., acetone. If desired, it may recrystallized from alcohol.
  • the oxides of aminocarboxylates or oxides of aminocarboxylic acids are built with Water soluble builder salts.
  • the builder salts are usually inorganic and most often are salts of alkali metals but suitable salts of other metals, such as alkaline earth metals, magnesium and aluminum, and non-metals and radicals, e.g., ammonium and organic cations, such as mono-, di-, and tri-alkylamines and alkanolamines wherein the alkyl and alkanol groups are of about 1 to 4 carbon atoms, preferably of 2 carbon atoms, are also useful.
  • the builder salts are preferably phosphates, including orthophosphates, pyrophosphates and tripolyphosphates, but the usual builder silicates, borates, carbonates, or bicarbonates, may be used instead of or in conjunction with the phosphates.
  • the builder salts are usually of alkaline pH in dilute solution and this also often increases the detergency of the built compound. However, in some circumstances it is desirable to maintain a lower pH and at such times more neutral builders, such as the alkali metal salts, both complete and partial, of sequestrants such as nitrilotriacetic acid or ethylene diamine tetraacetic acid may be employed.
  • Examples of the builders that may be used include sodium tripolyphosphate, tetrapotassium pyrophosphate, pentapotassium tripolyphosphate, sodium pyrophosphate, sodium hexametaphosphate, sodium carbonate, potassium carbonate, sodium tetraborate, sodium silicate (Na O/SiO ratios of about 0.5 to 0.3), potassium bicarbonate, potassium sesquicarbonate, sodium sesquicarbonate, trisodium nitrilotriacetate, tetrasodium salt of ethylenediamine tetraacetic acid, and the sodium salt of methylene diphosphonic acid.
  • the suitable corresponding alkaline earth metal, ammonium, lower alkanolamine or lower alkyl amine salts are also employable, either in complete or partial substitution therefor.
  • detergent-softener compositions there may be included for additional effects other detergents and softening compounds.
  • anionic synthetic organic detergents other detersive materials, such as compatible cationic, amphoteric and nonionic surface active agents and detergents may be used, too, in suitable formulations.
  • the anionic compounds include higher alkane sulfonates, higher fatty acid monoglyceride sulfates, linear higher alkyl benzene sulfonates, higher fatty acid soaps, polyoxyethylene sulfates, hydroxyalkane sulfonates, higher al cohol sulfates, salts of lower alcohol esters of sulfofatty acids, aromatic polyethoxyether sulfates, acyl sarcosinates, acyl esters of isethionates, acyl N-methyl taurides and others of the commercially available well-known anionic surface active agents and detergents.
  • the aromatic group will usually be benzene
  • the polyethoxy group will usually be from 3 to 30 ethoxys or other lower alkoxys
  • the lower alkyl will normally be of 1 to 6 carbon atoms
  • the higher alkyl will be of 8 to 22 carbon atoms, preferably from 12 to 18.
  • the salt-forming metals or other suitable radicals are preferably alkali metal, such as potassium and sodium, but alkaline earth metals, e.g., calcium, ammonium, lower alkyl amine, lower alkanolamine, and magnesium may also be employed.
  • anionic detergents include sodium lauryl sulfate; sodium linear tridecyl benzene sulfonate; triethanolamine lauryl sulfate; sodium and potassium coconut oil-tallow soaps; sodium lauryl sulfonate; potassium hexadecyl naphthalene sulfonate; lauryl alcohol ethylene oxide sulfate comprising 4 ethoxy groups per molecule; potassium stearyl glyceryl ether sulfonate; sodium lauroyl sarcosinate; and magnesium N-methyl tauride.
  • anionic surface active agents and to those of skill in the art identification of other members of this class will be obvious.
  • nonionic surface active agents are the condensation products of alkylated phenols with ethylene oxide, alkyl thiophenols with ethylene oxide, higher fatty alcohols with ethylene oxide and polyalkylene glycols or other polyols with lower alkylene oxides.
  • Specific compounds within this class are phenols condensed with from 6 to 30 moles of ethylene oxide; condensation products of polymers of propylene oxide with polymers of ethylene oxide; and ethers from higher fatty alcohols, such as lauryl alcohol, and polyethylene oxide.
  • cationic surface active agents that are usable are N-2-aminoethyl higher alkyl amines; N-2- aminoethyl higher fatty acid amides; quaternary ammonium compounds wherein an alkyl group is of about 12 to 18 carbon atoms and the other groups attached to the nitrogen are alkyls of 1 to 3 carbon atoms.
  • Typical of the preferred quaternary ammonium detergents are ethyl dimethylstearyl ammonium chloride; benzyl dimethylstearyl ammonium chloride; trimethylstearyl ammonium chloride; and trimethylcetyl ammonium bromide. Of course, others of these well-known cationic detergents may be used instead.
  • the quaternary surface active materials also function as softening agents.
  • amphoteric detergents which contain both anionic and cationic groups, include the N-higher alkyl betaines, N-alkyl-beta-aminopropionic acid; and N-alkyl-beta-iminodipropionic acid. It will be noted that these compounds bear a superficial resemblance to the softeners of the present compositions.
  • Other suitable amphoteric detergents include the fatty imidazolines and betaines containing a sulfonic group instead of a carboxylic group.
  • adjuvants may also be employed in the present detergent compositions.
  • these include filler salts; solvents; soil-suspending agents or anti-redeposition agents, such as sodium carboxymethyl cellulose and polyvinyl alcohol; perfumes; dyes; optical brighteners; antioxidants; preservants; hydrotropes, bactericides; anti-tarnish agents; opacifiers; bleaches; bluings; abrasives; enzymes; thickeners; foam-enhancing agents; foam-destructive agents; sequestrants; and various other adjuvants.
  • filler salts such as sodium carboxymethyl cellulose and polyvinyl alcohol
  • perfumes dyes; optical brighteners; antioxidants; preservants; hydrotropes, bactericides; anti-tarnish agents; opacifiers; bleaches; bluings; abrasives; enzymes; thickeners; foam-enhancing agents; foam-destructive agents; sequestrants; and various other adjuvants.
  • Examples of such materials include 2,6-di-tertiary butylphenol (antioxidant); sodium 2-sulfo-4-(2-naphtho-1,2 triaz'ole) stilbene (an optical brightener); lower alkyl aryl sulfonates such as sodium toluene sulfonate, sodium cumene sulfonate and potassium xylene sulfonate (hydrotropes); trichlorocarbanilide and hexachlorophene (bactericides); sodium perborate and potassium dichloroisocyanurate (bleaches); pepsin, keratinase and papain (enzymes); water, ethanol, propylene glycol, isopropanol (solvents); sodium sulfate (anhydrous), Glaubers salt, potassium sulfate, sodium chloride, ammonium sulfate (filler salts); lauric diethanolamide (foam enhancer and thicken
  • the detergent-softener compositions of this invention may be in either a solid or liquid form, including pastes, gels, free-flowing liquids, emulsions, lotions, thick liquids, bars, cakes, tablets, capsules, powders, granules, spraydried beads and other suitable forms. These may be produced by usual formulating and processing techniques. To make solids, it is possible merely to blend the various constituents of the desired composition and mix carefully. The powders resulting may be packaged in paperboard cartons or in water soluble polyvinyl alcohol packets. Alternatively, after mixing, these may be tabletted, milled, plodded and pressed, dried, agglomerated or subjected to other process steps.
  • the constituents are dissolved or suspended in a liquid medium, such as water or other suitable solvent, after which they may be treated to convert them to other suitable forms.
  • a crutcher mix or solution of the N-oxide aminocarboxylate and a is one case, a crutcher mix or solution of the N-oxide aminocarboxylate and a.
  • builder salt either with or without adjuvants, is spraydried in a conventional spray tower to produced particles or beads instead of mechanically blended powder.
  • filler salts, hydrotropes, other detergents and other'ad' juvants may be added after spray drying or, in suitable cases, may be blended in with the crutcher mix and dried with it.
  • the particle sizes be from 6 mesh to, 200 mesh, preferably being from 12 mesh to 100 mesh (US Standard Sieve Series). However, as indicated previously, other physical forms of the product may be employed.
  • Preferred ranges of propor tions of the active compound and builder salt, respectively, are 3 to 30% and 10 to 70% of the composition. If solid product is made, it will normally be most desirable to include from 10 to 20% of the active compound in it, together with 20 to 45% of a builder, such as pentasodium tripolyphosphate. Similarly, when solutions are marketed, they should contain from 5 to 20% of the active compound, 10 to 30% of builder salt, such as tetrapotassium pyrophosphate, and 35 to waterQAt such concentrations and with such materials, the detersive and softening effects are not adversely effected by the builder salt or other synthetic surface active agents or fillers. Rather, detergency is improved by the'builder and anti-static effects may often be noted on the washed textile. 1 1
  • liquid or solid adjuvants may also be employed.
  • This term includes other synthetic detergents, softeners, hydrotropes, solvents, fillers, etc., as well as other more minor additives.
  • an adjuvant may be included in the present composition, depending upon the nature thereof.
  • a supplemental. synthetic detergent, surface active agent or filler salt may be used in comparatively large proportion, e.g., 10 to 25%, whereas a fluorescent dye or perfume will usually be present only to a very minor extent, e.g., 0.1 to 2%.
  • Preferred-ranges for most of the various adjuvants are from 0.5 to 5% of each, with a total adjuvant content of no more than 50% of thecomposition.
  • inorganic filler salt can be used.
  • Such salts including sodium sulfate, potassium sulfate, and sodium; chloride, are often added to aid in improving the physical properties of particulate solid compositions. of this inven-- tion. They may also be present as byproducts of reac-- tion or as fillers in the starting materials. A preferred. concentration thereof in the present products is from 5 to 35%. In cases where some adjuvants may be incom patible upon storage with other constituents of the present; compositions, their effects may be obtained by adding them to the wash water together with the present compositions.
  • the vari-' ous constituents of these compositions may be mixed] together at any suitable stage of manufacture, in some cases even being added during the chemical manufacturing process whereby the present amine oxides are produced.
  • a synthetic detergent or hydro trope might be employed during the reaction of olefin oxide with amino acid to make the precursor of the pres ent compounds.
  • the surface active material can then be carried over with the active ingredient and have its effects utilized in the final product, as well as in the manufacturing procedure.
  • Processing temperatures may be from 20 C. to over 400 C. but are usually from room temperature to ordinary spray drying temperatures, such as 25 C. to 300 C.
  • the present compositions are diluted with about to 100,000 parts of solvent, such as water, per part of the N-oxide aminocarboxylate detergent-softener compound, to make an effective softening solution.
  • solvent such as water
  • the dilution will be with from about 500 to 25,000 parts and most preferably, with about 2,000 to 10,000 parts of water.
  • adjustment will be made for the generally lesser proportion of active material in the liquid preparation but it can be said that usually there will be used from about 100 to 4,000 times as much water as composition.
  • the amount of water employed will be from about 400 to 2,000 times the weight of the solid, whereas in the case of the liquid preparations, the ratio will be from about 200 to 1,000.
  • Textiles washable with the present compositions include those made from cotton, wool, rayon, nylon, polyesters, cellulose acetate, and other natural and synthetic fibers.
  • Human and animal hair, including living hair, may be treated with the N-oxide aminocarboxylates, but usually the compositions for treating living hair will contain little or no alkaline builder salt.
  • the detergent-softener composition is normally added as the active detergent ingredient to an automatic washing machine before beginning of washing. It may provide the entire detergent and softening actions or it may be supplemented by other preparations for such purposes. In either case, by adding before the final rinse, it is possible to have a softened wash Without the necessity for special equipment on the automatic washing machine or the need for the housewife to keep watch over the machine so that she may add softener in the rinse. A similar effect may be obtained by using approximately the same proportions of detergent-softener composition as a pre-soak, before washing. Such presoaking may be combined with an enzyme treatment. If considered desirable under the circumstances, the compositions may be added to the rinse water, although this is not usually necessary to obtain the desired softening effect.
  • the present products have been found to be effective in both hard and soft waters and when washing at either high or low temperatures.
  • they are useful detergentsofteners over a hardness range from soft water, e.g., 0f 0 to 50 p.p.m. hardness, to as much as 300 p.p.m. of hardness, calculated as calcium carbonate.
  • Such hardness may be due to Ca++, Mg' or other hardness ions or mixtures of such ions in the water.
  • the invented compositions are useful at washing temperatures ranging from 20 to 100 C. but most often the temperature of the Wash water is in the range from 30 to 70 C.
  • the builders employed in the present compositions are usually alkaline and therefore the wash water or soak or rinse water containing such compositions will usually be of pH in the range of 8 to 12, with the range from 9 to 11 being preferred. Nevertheless, it is possible to operate at other pHs with useful effect. In fact, a method of this invention for washing and softening textiles may also be followed in the absence of builder salt, in which case it is easy to obtain a lower pH, e.g., 4 to 7. Although it is most highly desirable to employ the N-oxides of N-(Z-hydroxy higher alkyl) aminocarboxylates in conjunction with inorganic builder salt, the present invented method extends to utilizing the active compounds alone or with adjuvants other than the builder salt.
  • soaking, washing and rinsing times employed are those ordinarily followed in treatments of textiles.
  • soaking may be for a period from about 5 minutes to overnight, washing may take about 2 to 25 minutes and rinsing may take about 2 to 10 minutes, in the usual machine washing operation. Nevertheless, other times and other obvious modifications of the preceding conditions may be made within the invention.
  • the above formula is compounded by mixing the various solid ingredients and dissolving in water, at approximately room temperature.
  • the product resulting is a clear one-phase, low viscosity liquid.
  • the N-oxide is made according to the method described in our application entitled N-oxide-Aminocarboxylates, filed together with this application.
  • the other ingredients are commercial products or are present with such products.
  • the softness observed is of a diiferent character from that obtained by rinse-treating textiles with quaternary ammonium halide softening agents.
  • the latter compounds impart a somewhat greasy feel to the textile, which is not noted when the present compounds are employed in the manner described.
  • compositions When the above compositions are used to treat a textile by pre-soaking in water containing 10 times the'above concentration of active softening composition of this invention, after overnight standing and subsequent Washing, rinsing and drying it is noted that the towel is significantly softer than a control towel not so pre-soaked or treated. Similar effects are noted when these compositions, with or without inorganic builder salt, are used to treat the towels in the rinse water, using the same washing machine and a usual washing cycle.
  • a powdered detergent-softening composition is made by blending together, in powder form, 15% of N-(Z-hydroxy higher alkyl)-N-methyl glycine-N-oxide salt, or N-(2-hydroxy higher alkyl) iminodiacetic acid-N-oxide salt with 35% pentasodium tripolyphosphate and sodium sulfate.
  • the composition prepared is tested for detergency at 0.15% concentration.
  • Four different active ingredients are included in these various formulations and the effects thereof are given below.
  • the test employed to measure detergency is identified as the Spangler Soil Detergency Test.
  • composition based on active ingredient derived from epoxide A having shorter carbonchains
  • EXAMPLE 4 The softening effects of powdered detergent compositions of this invention are tested by making up several compositions comprising 2 parts of the amine oxide compound and 6.6 parts of sodiumtripolyphosphate. This free-flowing powder is used to wash one-half of a terrycloth hand towel in three gallons of New Brunswick, NJ. tap water (90 p.p.m. hardness), at 120 F. The washing is carried out, employing 8.6 grams of the composition and using a General Electric automatic washing machine with Minibasket attachment in the machine. In a similar manner, control softener formulations are employed and towels washed therewith are compared to those washed using the experimental compositions. The towels washed are 13 inches by 16 inches and are purchased from J. C. Penney Co.
  • the softness of the towels washed by various compositions is rated on the scale of 1 to 10 with 1 indicating a towel which is not soft and 10 indicating excellent softness. Such ratings are made by comparison with control towels washed in detergents or softening agents of known characteristics. Results of this test are reported in Table 2.
  • the corresponding potassium or ammonium salts are used and when there are used stoichiometrically equivalent proportions of other compounds in these compositions, such as oxides of N-(2- hydroxy-n-butyl)-N-n-propylamine-N-propionic acid, ptassium salt; N-(Z-hydroxy-n-decyl)-N-aminobenzoic acid, ammonium salt.
  • R is an alkyl radical of 4 to 20 carbon atoms, or alkenyl radical of 4 to 20 carbon atoms containing one or two ethylenic double bonds
  • R is alkyl of 1 to 7 carbon atoms or is R COOX
  • R is alkylene or aromatic hydrocarbon radical of 1 to 9 carbon atoms
  • X is hydrogen, alkali metal, alkaline earth metal, ammonium, monoalkylamine, dialkylamine, trialkylamine, monoalkanolamine, dialkanolamine, or trialkanolamine, in which the alkyl and alkanol groups are of 1 to 4 carbon atoms
  • m is from /3 to 1 and n is from 1 to 3, and a water soluble neutral to alkaline inorganic salt builder for the compound, which increases the detergency thereof.
  • a composition according to claim 1 wherein, in the formula of the compound, m and n are both equal to 1, R is an aliphatic hydrocarbon radical of 8 to 14 carbon atoms, R is an aliphatic hydrocarbon radical of 1 to 2 carbon atoms or is R COOX, R is a divalent aliphatic hydrocarbon radical of 1 to 3 carbon atoms, both Xs, if a plurality is present, are the same and both R s, if a plurality is present, are the same, and the builder salt is an alkali metal phosphate, silicate, borate, carbonate or bicarbonate, or alkali metal salt of nitrilotriacetic acid, ethylene diamine tetra acetic acid or methylene diphosphonic acid.
  • composition according to claim 2 which comprises from 2 to 50% of said compound and from 5 to 98% builder salt.
  • composition according to claim 3 wherein said compound is 3 to 30% and the builder salt is from 10 to 70% of the composition.
  • composition according to claim 4 in said compound of which R is a linear alkyl radical of 10 to 14 carbon atoms, R is methylene and X is alkali metal, and in which composition the builder salt is an alkali metal phosphate.
  • composition according to claim 5 which is in particulate solid form and which comprises from 10 to 20% of said compound and from 25 to 45% pentasodium tripolyphosphate.
  • composition according to claim 5 which is in liquid form and which comprises from 5 to 20% of said compound, 10 to 30% tetrapotassium pyrophosphate and from 35 to water.
  • composition according to claim 6 wherein, in said compound, R is of about 14 carbon atoms, terminally joined to the rest of the compound, X is sodium and R is methyl.
  • composition according to claim 7 wherein, in said compound, R is of about 14 carbon atoms, terminally joined to the rest of the compound, X is sodium and R is methyl.
  • composition according to claim 6 wherein, said compound, R is of about 14 carbon atoms, terminally joined to the rest of the compound, X is sodium and R is R COOX.
  • composition according to claim 7 wherein, in said compound R is of about 14 carbon atoms, terminally joined to the rest of the compound, X is sodium and R is R COOX.
  • composition according to claim 3 further containing a compatible anionic, cationic, amphoteric or nonionic detergent.
  • a method of treating textiles which comprises contacting a textile with an aqueous solution of a compound of the formula wherein R is an alkyl radical of 4 to 20 carbon atoms, or alkenyl radical of 420 carbon atoms containing one or two ethylenic double bonds, R is alkyl of l to 7 carbon atoms or is R COOX R is alkylene or aromatic hydrocarbon of 1 to 9 carbon atoms, X is hydrogen, alkali metal, alkaline earth metal, ammonium monoalkylamine, trialkylamine, monoalkanolamine, dialkanolamine, or trialkanolamine, in which the alkyl and alkanol groups are of 1 to 4 carbon atoms, m is from ml and n is from 1 to 3, and a water soluble neutral to alkaline inorganic salt builder for the compound, which increases the detergency thereof.
  • R is an aliphatic hydrocarbon radical of 8 to 14 carbon atoms
  • R is an aliphatic hydrocarbon radical of 1 to 2 carbon atoms or is R COOX
  • R is a divalent aliphatic hydrocarbon radical of 1 to 3 carbon atoms
  • both Xs, if a plurality is present, are the same and both R s, if a plurality is present, are the same
  • the builder salt is an alkali metal phosphate, silicate, borate, carbonate or bicarbonate, or alkali metal salt of nitrilotriacetic acid, ethylene diamine tetra acetic acid or methylene diphosphonic acid.
  • a method according to claim 16 wherein the application of the composition to the textile is in the washing step of an automatic washing machine operation and the textile is of either cotton, wool, rayon or synthetic ber.
  • composition is initially in powder form, comprising 10 to 20% of a compound wherein R is of about 14 carbon atoms, terminally joined to the rest of the compound, and X is sodium and R is methyl, and 20 to of pentasodium tripolyphosphate.
  • composition is initially in a liquid state, comprising from 5 to 20% of compound wherein R is of about 14 carbon atoms and termnally joined to the rest of the compound, X-is sodium and R is methyl, and 10 to 30% of tetrapotassium pyrophosphate.
  • composition further containing a compatible anionic, cationic, amphoteric or nonionic detergent.

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  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US880977A 1969-11-28 1969-11-28 Detergent compositions containing n-oxide-aminocarboxylates Expired - Lifetime US3700607A (en)

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US88090969A 1969-11-28 1969-11-28
US88091569A 1969-11-28 1969-11-28
US88099169A 1969-11-28 1969-11-28
US88099269A 1969-11-28 1969-11-28
US88097769A 1969-11-28 1969-11-28
US88098269A 1969-11-28 1969-11-28
US324314A US3864389A (en) 1969-11-28 1973-01-17 N-(2-Hydroxyhydrocarbyl) Iminodicarboxylates

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US880977A Expired - Lifetime US3700607A (en) 1969-11-28 1969-11-28 Detergent compositions containing n-oxide-aminocarboxylates
US00880991A Expired - Lifetime US3755435A (en) 1969-11-28 1969-11-28 N-(2-hydroxy-higher hydrocarbyl)-n-lower hydrocarbyl-aminocarboxylates
US00880992A Expired - Lifetime US3725473A (en) 1969-11-28 1969-11-28 N-(2-hydroxyhydrocarbonyl) iminodicarboxylates
US00880909A Expired - Lifetime US3728385A (en) 1969-11-28 1969-11-28 N-oxide-iminodicarboxylates
US00880915A Expired - Lifetime US3726797A (en) 1969-11-28 1969-11-28 Detergent compositions and processes incorporating n-(2-hydroxy hydrocarbyl)iminodicarboxylates
US324314A Expired - Lifetime US3864389A (en) 1969-11-28 1973-01-17 N-(2-Hydroxyhydrocarbyl) Iminodicarboxylates

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US00880992A Expired - Lifetime US3725473A (en) 1969-11-28 1969-11-28 N-(2-hydroxyhydrocarbonyl) iminodicarboxylates
US00880909A Expired - Lifetime US3728385A (en) 1969-11-28 1969-11-28 N-oxide-iminodicarboxylates
US00880915A Expired - Lifetime US3726797A (en) 1969-11-28 1969-11-28 Detergent compositions and processes incorporating n-(2-hydroxy hydrocarbyl)iminodicarboxylates
US324314A Expired - Lifetime US3864389A (en) 1969-11-28 1973-01-17 N-(2-Hydroxyhydrocarbyl) Iminodicarboxylates

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US3888798A (en) * 1970-11-16 1975-06-10 Colgate Palmolive Co Liquid detergent composition
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US4129527A (en) * 1974-11-07 1978-12-12 The Clorox Company Liquid abrasive detergent composition and method for preparing same
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
US4359413A (en) * 1981-03-17 1982-11-16 The Procter & Gamble Company Solid detergent compositions containing alpha-amine oxide surfactants
US4397776A (en) * 1981-03-17 1983-08-09 The Procter & Gamble Company Liquid detergent compositions containing alpha-amine oxide surfactants
US7645731B1 (en) 2009-01-08 2010-01-12 Ecolab Inc. Use of aminocarboxylate functionalized catechols for cleaning applications

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US3888797A (en) * 1970-08-04 1975-06-10 Carapus Company Limited Detergent composition
DE2111950A1 (de) * 1971-03-12 1972-11-23 Degussa Verwendung von Salzen bestimmter Hydroxyalkylaminosaeuren als waschaktive Substanzen
FR2327310A1 (fr) * 1972-11-30 1977-05-06 Modokemi Ab Composition detergente liquide
US3929679A (en) * 1973-10-26 1975-12-30 Colgate Palmolive Co Particulate silicate-hydroxyalkyl iminodiacetate built detergent compositions of improved properties
US3953379A (en) * 1973-10-26 1976-04-27 Colgate-Palmolive Company Manufacture of improved aqueous alkali metal silicate-alkali metal hydroxyalkyl iminodiacetate compositions
DE2356322A1 (de) * 1973-11-10 1975-05-15 Henkel & Cie Gmbh Schmiermittel fuer die kaltbearbeitung von aluminium und aluminiumlegierungen
US4055596A (en) * 1974-09-13 1977-10-25 Merck & Co., Inc. 11,12-Seco-prostaglandins
FR2285869A1 (fr) * 1974-09-30 1976-04-23 Anvar Nouveaux acides iminodiacetiques n-substitues, leur procede de preparation et applications de ces composes en tant qu'agents chelatants ou therapeutiques
SE386083B (sv) * 1975-01-15 1976-08-02 Berol Kemi Ab Forfarande for flotation av bly-, uran- och sellsynta jordartsmineral ur malmer
DE2556376C2 (de) * 1975-12-15 1983-07-07 Henkel KGaA, 4000 Düsseldorf Verfahren zum Färben von Polyacrylnitril-Fasermaterial
US4259249A (en) * 1979-06-13 1981-03-31 The Procter & Gamble Company Preparation of hydroxyl zwitterionic compounds
OA06199A (fr) * 1981-05-13 1981-06-30 Berol Kemi Ab Procédé de flottation de minéraux phosphatés et composé destiné à ce procédé.
US4375422A (en) * 1981-11-12 1983-03-01 Lever Brothers Company Homogeneous detergent containing nonionic and surface active iminodipropionate
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JPS58110543A (ja) * 1981-12-25 1983-07-01 Daikin Ind Ltd 含フツ素アミノカルボン酸化合物およびその製法と用途
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US5089614A (en) * 1982-04-12 1992-02-18 The B. F. Goodrich Company Polysubstituted 2-morpholones
DE3544045A1 (de) * 1984-12-24 1986-06-26 Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld Neue n-(2-hydroxyalkyl)-aminosaeuren und ihre derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
DE3712330A1 (de) * 1987-04-11 1988-10-20 Basf Ag 2-hydroxy-3-amino-propionsaeure-n,n-diessigsaeure und ihre derivate, ihre herstellung und verwendung insbesondere als komplexbildner und diese enthaltende wasch- und reinigungsmittel
DE3712329A1 (de) * 1987-04-11 1988-10-20 Basf Ag Verfahren zur herstellung von serin-n,n-diessigsaeure und derivaten, ihre verwendung insbesondere als komplexbildner und diese enthaltende wasch- und reinigungsmittel
US5243072A (en) * 1988-06-13 1993-09-07 Th. Goldschmidt Ag Betaine group-containing polysaccharides with recurring anhydroglucose units, their synthesis and their use in cosmetic preparations
DE3829829A1 (de) * 1988-09-02 1990-03-22 Basf Ag Verfahren zur herstellung des trinatriumsalzes von isoserin-n,n-diessigsaeure
US5254290A (en) * 1991-04-25 1993-10-19 Genevieve Blandiaux Hard surface cleaner
FR2707289B1 (fr) * 1993-07-06 1995-08-11 Chemoxal Sa Procédé de préparation d'un composé hydroxylé d'amine secondaire ou tertiaire.
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US5843029A (en) * 1995-10-16 1998-12-01 Gerber/Baby Care Manual breast pump
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888798A (en) * 1970-11-16 1975-06-10 Colgate Palmolive Co Liquid detergent composition
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US4129527A (en) * 1974-11-07 1978-12-12 The Clorox Company Liquid abrasive detergent composition and method for preparing same
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
US4359413A (en) * 1981-03-17 1982-11-16 The Procter & Gamble Company Solid detergent compositions containing alpha-amine oxide surfactants
US4397776A (en) * 1981-03-17 1983-08-09 The Procter & Gamble Company Liquid detergent compositions containing alpha-amine oxide surfactants
US7645731B1 (en) 2009-01-08 2010-01-12 Ecolab Inc. Use of aminocarboxylate functionalized catechols for cleaning applications

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CH558332A (de) 1975-01-31
CA942458A (en) 1974-02-26
US3725473A (en) 1973-04-03
US3864389A (en) 1975-02-04
CA941557A (en) 1974-02-12
CH569695A5 (pm) 1975-11-28
CA941556A (en) 1974-02-12
BE759533A (fr) 1971-04-30
NL7017496A (pm) 1971-06-02
US3726797A (en) 1973-04-10
FR2099030A5 (pm) 1972-03-10
DE2057355A1 (de) 1971-07-22
US3755435A (en) 1973-08-28
GB1319130A (en) 1973-06-06
US3728385A (en) 1973-04-17

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