Classifications

• • 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 and R are divalent aliphatic or aromatic hydrocarbon radicals of 1 to 9 carbon atoms
• X and Y are either hydrogen or salt-forming elements or radicals.
• R is a saturated radical of 12 to 20 carbon atoms
• R and R are identical alkylene radicals of l to 2 carbon atoms
• X and Y are the same monovalent metals, or lower alkanolamines, e.g., sodium, triethanolamine.
• compositions comprise an inorganic builders salt, such as sodium tripolyphosphate or potassium pyrophosphate, and also may include other adjuvant materials, such as trisodium nitrilotracetate, enzymes, anti-redeposition agents, bleaches or bluing agents, germicides, hydrotropes, auxiliary detergents and softening agents, etc.
• inorganic builders salt such as sodium tripolyphosphate or potassium pyrophosphate
• adjuvant materials such as trisodium nitrilotracetate, enzymes, anti-redeposition agents, bleaches or bluing agents, germicides, hydrotropes, auxiliary detergents and softening agents, etc.
• the iminodicarboxylate comprises from 3 to 30% of the composition and the inorganic builder salt is from 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 iminodicarboxylate can be used without inorganic builder salt, in which case it normally functions primarily as a softening agent and is preferably utilized in the rinse water, after completion of washing, although it may also be used alone in a pre-soaking or washing operations.
• compositions and processes for the treatment of textiles, clothing or laundry to clean and soften such items and to impart anti-static properties to them.
• the invented compositions and processes incorporate or utilize N-(Z-hydroxy hydrocarbyl) iminodicarboxylates or the corresponding carboxylic acids and are particularly suitable for treatment of cotton and cottoncontaining materials, although they are also useful for application to other natural and synthetic products.
• the present invented processes and compositions utilizing the N-(2-hydroxy hydrocarbyl) iminodicarboxylate described herein, allow improved washing of textiles and laundry, with the washed materials being of greater softness and having antistatic properties.
• Such results are obtainable by applying the mentioned compounds, either in built or unbuilt compositions, to the materials to be treated, either before, during or after washing.
• the present iminodicarboxylates are exceptionally substantive to fabrics and a sufficient proportion thereof remains on the fabric so as to make it soft and impart antistatic properties to it. 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.
• the compounds are generally of the controlled foaming type, resulting in a visible foam which is not clogging in an automatic washing machine.
• the processes may be used in conjunction with various 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.
• the present compositions including the N-(2- hydroxyhydrocarbyl) iminodicarboxylates or the corresponding acids, counteract this tendency toward discoloration.
• Nylon is only very slightly yellowed by such contact, with present solutions.
• built synthetic organic detergent compositions comprise an inorganic builder salt and an N-(Z-hydroxyhydrocarbyl) iminodicarobxylate or corresponding acid of the formula:
• R is an aliphatic hydrocarbon radical of 4 to 20 carbon atoms
• R and R are divalent, aliphatic or aromatic hydrocarbon radicals of l to 9 carbon atoms
• X and Y are hydrogen or a salt-forming element or radical.
• R and R may be the same or different and X and Y may be the same or different. If eiher X or Y is an element, it is preferred that it should be an alkali metal, an alkaline earth metal or other suitable salt-forming metal, capable of making the compounds water soluble.
• X or Y is a radical, it is preferred that such be ammonium, alkylamine or alkanolamine, either mono-, di-, or tri-alkylamine or mono-, ditri-alkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of l to 4 carbon atoms, preferably 2 to 3 carbon atoms.
• the compounds are those wherein R is an aliphatic hydrocarbon radical of 12 to 20 carbon atoms, R and R are aliphatic alkylene radicals of 1 to 2 carbon atoms, and X and Y are monovalent salt-forming ions, including alkali metal, ammonium, mono-, diand tri-alkylamine and mono, diand tri-alkanolamine.
• R and R are same and that X and Y are the same.
• X and Y stand for a monovalent portion of any salt-forming ion.
• a divalent ion such as magnesium
• it could be joined to both the carboxylic groups of the present compounds or could be joined to only one of them, with another valence bond either otherwise tied up, as with a different anion, or with it joined to the carboxylic groups of different iminodicarboxylic acids.
• mixed salts may be formed, as may be acid-salt compounds.
• mixtures of different iminodicarboxylates may also be used.
• the hydroxy substituted hydrocarbon radical is a hydroxy substituted higher aliphatic hydrocarbon radical, preferably a hydroxy-higher linear alkyl, and in which the R and R are lower or higher hydrocarbon radicals.
• the compounds so described which may be outside the range of normally used compounds, are considered to be useful in some built detergent-softener compositions and in textile-treating methods, to clean, soften or make anti-static, various textiles contacted therewith.
• the preferred com-positions and methods mentioned above are found to be excellent for softening textiles, especially for cotton articles which are washed with them, even in the presence of various builders, other detergents and adjuvants. They may also be used in normal washing procedures, including rinsing and presoaking operations.
• the most preferred compounds of the compositions and processes are the salts of -N-(2-hydroxyhigher alkyl) iminodilower carboxylic acids, wherein the higher alkyl is of 14 to 22 carbon atoms and is of straight chain structure. Of such compounds, it is preferred to employ the sodium and potassium salts, with the sodium salt being that which is generally considered most useful.
• acetic acid the most preferred is acetic acid, so that the most preferred of these compounds are the N-(Z-hydroxy-higher alkyl)-iminodiacetates.
• the use of these compounds in the present compositions and methods results in a surprisingly effective textile-softening action and detergency, especially with cotton, even when applied to the textile or laundry in the washing operation and even when no additional active synthetic organic detergent materials are present.
• compositions have exceptionally good softening activities on textiles and laundry.
• Other compositions within the scope of the present invention are also useful as surface active agents, wetting agents, emulsifiers and detergents, although they might not produce to the same extent the extremely desirable softening activity shown by the most preferred compositions.
• such compositions may be only moderately effective as softeners, although they will often have the advantage of being very useful because of their other surface active properties, such as detergency, often in both hard and soft 4 waters and at elevated and comparatively low washing temperatures.
• substituents are amino, hydroxy, halogen, e.g., chlorine, bromine, fluorine, and hydroxylower alkyl wherein the alkyl is up to four carbon atoms.
• the number of Such substituents present will usually be small, often no more than four per molecule and usually, less than three. It is generally preferable that the compounds be unsubstituted but many of the substituted compounds are often of utilities similar to those of the compounds literally within the formulas given and therefore, are also contemplated as relevant to this invention.
• mixed salts may be employed, as may be acid salts.
• the hydrocarbyl groups, R include both saturated and relatively slightly unsaturated radicals.
• one or two double bonds per R are acceptable and are within the present invention, although it is preferred to employ alkyl groups as R
• alkyl groups straight chain alkyls, which are terminally joined to the carbon to which the hydroxy group is attached, are highly preferred, and are intended to be described herein, unless otherwise indicated, although those alkyl groups which are not terminally joined also possess utility, as do various alkyl groups of non-linear structures.
• medially joined keryl (alkyl derived from kerosene) may be used for R
• various polymeric radicals such as propylene tetramer and pentamer, a preferred form of which is often such a mixture thereof as to average 13 carbon atoms per group.
• cycloalkyl groups employed, either alone or with linear alkyls, e.g., cyclohexyldecyl.
• R and R are preferably short chain alkylene, usually of 1 to 2 carbon atoms, but longer chain alkylenes and divalent hydrocarbyl radicals containing aromatic moieties are also useful to make detergent and softener products.
• the alkylenes will be present with a carbon content of the alkylene groups, R and R of four or less but in some instances as many as nine carbon atoms may be found in such group to be good for making the novel and useful surface active products.
• aromatic materials it is preferred that they be derivatives of benzene, usually with no more than two substituents on the benzene ring, in addition to joinder of the benzene ring to the rest of the present molecule.
• X and Y while they may be hydrogen, are preferably salt-forming ions.
• the salts made are usually more stable and freer flowing than the acids and because the product is most frequently employed in alkaline solutions, it is therefore preferably in the salt form.
• the salt-forming ions those which are monovalent are generally preferred, usually because of their greater water solubility, which is an important feature in the use of the present compositions in aqueous systems. However, even if water solubility is low, salts of low solubility can be employed as washing agents in other polar media and may be useful in an aqueous medium, especially if solvents or solubilizers are present.
• N-substituted iminodicarboxylates of the present compositions and methods can be prepared by reaction of a hydrocarbon-1,2-epoxide with an iminodicarboxylic acid, usually in the form of a salt.
• the reaction is shown in the following equation:
• the described reaction is normally effected in aqueous solution, wherein the hydrocarbon-1,2-epoxide is added in stoichiometric proportion to a solution of a salt of the iminodicarboxylic acid.
• a hydrotrope or auxiliary solvent such as alcohol, may be employed to assist in solubilizing the epoxide.
• the reaction will ordinarily occur at elevated temperature and to minimize foaming, may be effected under pressure.
• solvent may be removed by any convenient means, e.g., freeze drying, and the product may be recrystallized from a suitable solvent, e.g., alcohol.
• the iminodiacids and their salts are known compounds, as are the hydrocarbon epoxides. Methods for making such compounds from readily available starting materials are also known to those of skill in the art and accordingly, they need not be described here. Further details relevant to the manufacture of the present N-(Z-hydroxy- 6 hydrocarbyl)-N-iminodicarboxylates and the corresponding acids are given in our application for patent entitled N-(Z-Hydroxyhydrocarbyl) Iminodicarboxylates, U.S. application Ser. No. 880,992, filed by us in the U.S. Patent Office on the same date as the present application.
• the reaction may be effected at various temperature, it is normally preferred to initiate it at approximately room temperature, e.g., 15-30 C.
• the iminodiacid reactant is dissolved in an aqueous medium and it is preferred to utilize deionized water for such medium.
• the proportion of water employed may be relatively small, and usually it is preferred to use from 25 to 200% of the total weight of the reactants.
• the epoxide usually as a liquid
• the epoxide is admixed with the dissolved reagent.
• Such admixing may take from ten seconds to one hour and during mixing the temperature of the reaction mixture is held within the mentioned room temperature range.
• the temperature is usually raised to from 50 C. to C., depending upon the materials being reacted.
• the temperature most conveniently employed is the reflux temperature of the reaction mix.
• the reaction mixture is held at such temperature for a period of from about one hour to about 42 hours, after which it is considered that the reaction is complete.
• a One-phase system is found, from which the product may be obtained by precipitating with a suitable lower ketone, e.g., acetone, methyl ethyl ketone, diisopropyl ketone or other ketone having one to four carbon atoms in the alkyl groups thereof.
• a suitable lower ketone e.g., acetone, methyl ethyl ketone, diisopropyl ketone or other ketone having one to four carbon atoms in the alkyl groups thereof.
• Conversion to a solid crystal form may often be effected by treatment with a lower alcohol, such as isopropanol or ethanol, after which purification may be effected by recrystallization from such solvent.
• the iminodicarboxylates obtained by following the above described method for their manufacture are usually white or lightcolored solids, sometimes with a slight yellowish tinge They may be somewhat hygroscopic but are sufficiently free-flowing to be employed, either by themselves or with other materials, such as the present inorganic builder salt, in surface active materials such as detergent-softeners for textiles.
• N-(Z-hydroxyhydrocarbyl) iminodicarboxylates or the corresponding acids are formulated with suitable builder materials.
• the builders are highly preferably in the forms of inorganic Water soluble salts but other builder materials may also be employed, including insoluble inorganics and soluble organic compounds. Materials of these types are well known and have been described in various textbooks on detergency.
• the soluble inorganic salts are most often 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.
• 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 bicarbouates, 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 tripolyphosphates, 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. Of course, mixtures are also useful.
• the water soluble inorganic salt builders and the water soluble or organic builders mentioned above are those which are most frequently employed in the present detergent compositions. However, in addition to the preferred condensed phosphates or in replacement of them, similar dispersing, peptizing, sequestering and alkalizing actions may be obtained from various other compounds, which have been suggested as builders for synthetic detergents.
• Mixed sodium and potassium salts of the condensed phosphates, including the glassy phosphates may be emloyed, as may be mixed salts of silicates or tetraborates.
• Insoluble inorganic builders such as clays, including kaolin, montmorillonite and bentonite can be used for certain applications, as may be synthetic colloidal magnesium and aluminum silicates, silica sols and diatomaceous earths.
• kaolin including kaolin, montmorillonite and bentonite
• Among other suggested builders are sodium zincate, ammonium carbonate, dicyandiamide, sodium fiuosilicate, and guanidine salts, such as guanidine carbonate.
• Various organic builders of known types may be used to obtain special eflects. Some of these are listed hereafter in the recital of various adjuvants that may be employed with the present compositions.
• 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 cations, 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 alcohol 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 ethoxys or other lower alkoxys
• the lower alkyl will normally be of 1 to 6 carbon atoms and 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 s arcosinate; 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 con densation 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-aminoethyl higher alkyl amine; N-2 aminoethyl higher fatty acid amides; quarternary 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 trimethylacetyl 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.
• the 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; preservatives; hydrotropes; bactericides; anti-tarnish agents; opacifiers; bleachers; 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; preservatives; hydrotropes; bactericides; anti-tarnish agents; opacifiers; bleachers; 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-triazole) 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 thickener)
• 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 of the composition are first dissolved or suspended in a liquid medium, such as water or other suitable solvent. They may then be treated in any of various suitable ways to convert them to desired forms.
• a crutcher mix or solution of the iminodicarboxylate and a builder salt, either with or without adjuvants is spray-dried in a conventional spray tower to produce particles or beads instead of mechanically blended powder.
• the filler salts, hydrotropes, other detergents and other adjuvants may be added after spray drying or, in suitable cases, may be blended in with the crutcher mix and dried with it.
• the product is to be a liquid, it is preferred that it be a free flowing liquid, of a viscosity between that of water and a syrup, such as maple syrup. If produced as a powder, it is preferred that the particle sizes be from 6 mesh to 200 mesh, preferably being from 12 to 100 mesh (US. Standard Sieve Series). However, as indicated previously, other physical forms of the composition may be employed.
• Preferred ranges of proportions of the active compound and builder salt, respectively, are 3 to 30% and to 70% of the composition. If a 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 tripolyphosphates. 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 85% water. At such concentrations and with such materials, the detersive effects of the softening composition are not adversely affected by the builder salt or other synthetic surface active agents or fillers. Rather, detergency is improved by the builder and anti-static action may often be noted on the washed textiles.
• 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 the composition.
• 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 invention. They may also be present as byproducts of reaction 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 incompatible 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.
• 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 iminocarboxylates are produced.
• a synthetic detergent or hydrotrope might be employed during the reaction of olefin oxide with iminodicarboxylic acid to make the precursor of the present 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 temperature, such as 25 C. to 300 C.
• the present compositions are diluted with about 10 to 100,000 parts of solvent, such as water, per part of the iminocarboxylate 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 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 p esent 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 iminodicarboxylate, but usually 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 pre-soa'king 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., of 0 to 50 p.p.m. hardness, to as much as 300 ppm. of hardness, calculated as calcium carbonate.
• Such hardness may be due to calcium, magnesium 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 10, with 9' to 10 being preferred. Nevertheless, it is possible to operate at other pHs with useful effect.
• 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 an acid pH, e.g., 4 to 7.
• the present invented method extends to utilizing the active compounds alone or with adjuvants other than the builder salt.
• the amount of inorganic builder salt present may be diminished and even reduced to zero.
• the gentler action of the present composition without builder or with insoluble or non-alkaline builder, may be preferred.
• the useful detergency of the present iminodicarboxylates allows their employment without builder in many such situations.
• the methods of use of such compositions, without builder salt, are the same as those previously described herein.
• 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 minutes, in the usual machine washing operation. Nevertheless, other times and other obvious modifications of the preceding conditions may be used within the invention.
• EXAMPLE 1 Percent N-(Z-hydroxyhexadecyl)-iminodiacetic acid disodium salt 23 Pentasodium tripolyphosphate 77
• N-(Z-hydroxyhexadecyl)-iminodiacetic acid, disodium salt is made reacting 1,2-hexadecane epoxide with iminodiacetic acid, disodium salt, according to the method described in this specification and more specifically, in accordance with the method of our patent application entitled N-(Z-Hydroxyhydrocarbyl) Iminod'icarboxylates, filed on the same day as the present application.
• the built composition described above. is tested for efficacy as a fabric softener and is found, by standard test, to obtain an exceptionally high rating (10+), indicating an excellent softening etfect.
• the test is conducted on cotton materials but softening is also noted on other natural and synthetic organic textiles, e.g., rayon, wool, polyester blends, nylon.
• the test utilizes one-half of a terrycloth towel in three gallons of water, having an approximate hardness of 100 parts per million, as calcium carbonate.
• the water used is at 120 F. and contains 8.6 grams of the composition of this example in the three gallons used.
• the towel is washed in a Mini-basket of a General Electric Company automatic electric washing machine, using the conventional washing and rinsing cycles.
• Washing lasts for approximately 10' minutes and rinsing takes about the same time. After rinsing, the towel is essentially freed of water and is dried, after which softness is rated on a scale of 1 to 10, with 1 indicating a towel that is not soft and 10 indicating excellent softness.
• EXAMPLE 2 Percent N-(Z-hydroxydodecyl)-iminodiacetic acid, disodium salt 15 Sodium tripolyphosphate 35 Sodium sulfate 50
• a detergent powder formula of the above composition is made, in which the particles are in the range of 6 to mesh, US. Standard Sieve Series.
• the composition is made by mechanically blending of solid particles of various ingredients but may also be made by spray drying an aqueous crutcher mix thereof.
• the composition is tested for detergency by the preparation of a 0.15% solution of the product in water, followed by the washing of the three cotton percale swatches, each three inches by six inches.
• the 0.15% concentration corresponds to that normally recommended for use in a home automatic washing machine.
• the cotton percale swatches are first soiled with a mixture of airborne and sebum soils so that the degree of soil removal can be utilized as a measure of detergency.
• the swatches are washed in a Tergotometer evaluating washing machine, using waters of two different hardnesses, at two different temperatures, as indicated in the accompanying table. After washing, the swatches are rinsed and then tested for whiteness, using a color difference meter.
• the time of washing is about 12 minutes and rising is effected in about 10 minutes.
• the swatches are tested for whiteness, using a color difference meter.
• a comparison of readings, using the Rd scale, between the materials before and after washing, is made and the delta Rd is calculated.
• the greater the delta Rd the more efiicient the soil removal and the better is the detergency obtained.
• Linear tridecyl benzene sulfonate, as the sodium salt thereof, is employed as a standard of comparison for detergency in this test.
• the test is also run using N-(Z-hydroxyhexadecyl)-iminodiacetic acid, disodium salt instead of the N-(2-hydroxydodecyl)-iminodiacetic acid, disodium salt.
• compositions tested which are considered to be representative of those made in accordance with this invention, as described above, are useful detergents. They are effective in hard water and in water of medium hardness and are good for both hot and cold water washing. It is seen that they are most effective in ordinary city water of medium hardness, such as New Brunswick, NJ. tap water. They wash better in hot water than in cold water. Similar results are obtained by the use of other iminodicarboxylates wherein the hydroxyalkyl is of 8, 10, 14, 18 or 20 carbon atoms.
• An additional benefit resulting from application of the process of this invention is that the cloths washed, whether cotton or the more static-prone nylon, polyester, or blend of synthetic fibers, are observed to be free of static after several washings.
• the diminution of static charge on the washed materials is apparent after one washing but appears to be increased by repeated washings, apparently indicating that with additional washings, more of the treating iminodicarboxylate is absorbed onto the washed fibers, with consequent decrease in the ability of the fiber to hold an electric charge.
• Dye Poly brilliant blue, RAW
• 1% aqueous solution Water The above composition is made by dissolving the solid materials in the aqueous phase, at room temperature, to
• the liquid composition is tested for utility as a softener in the wash cycle of an automatic washing machine by adding 60 grams of the solution to 17 gallons (a tub-full) of New Brunswick, NJ. tap water at 120 F., together with cup of commercial, low-foaming, built synthetic detergent (Ad).
• Ad commercial, low-foaming, built synthetic detergent
• a terrycloth hand towel is washed in such solution and in other tests, a full load of mixed and soiled wash is used.
• the towel and the wash exhibit notable increases in softness, despite being washed in the presence of a commercial heavy duty synthetic organic detergent. Of course, the wash is also satisfactorily cleaned.
• composition is also useful as a pre-soak for treatment of stubbornly stained items of clothing.
• an enzyme may be papain, lipase or amylase.
• the above liquid preparation may be made by mixing the ingredients at room temperature. It is a clear, single phase, low viscosity product.
• the product is evaluated in an automatic washing machine by adding 60 grams thereof to the rinse cycle, following washing of a single towel or an ordinary wash load in New Brunswick, N.I., tap water, at 120 F.
• the rinse is effected with either warm or cold water, over a period of about 10 minutes.
• the concentration of the liquid composition in the wash water (the tub holds 17 gallons) is about 0.1%. After completion of the rinsing operation and air drying or machine drying of the articles washed and rinsed, it is noted that they are significantly softer than a control on which no softener had been employed.
• composition is used to make a presoak solution, wherein the wash is allowed to soak at room temperature in an aqueous solution of the composition at a concentration of about 1%, for a period of about three hours, before washing in a solution of commercial detergent in an automatic washing machine.
• builder salt is included with the composition, to the extent of 10 to 50%, e.g., tetrapotassium pyrophosphate, sodium carbonate, or when synthetic detergent, e.g., sodium lauryl sulfate, potassium hexadecyl sulfonate or sodium N-lauroyl sarcoside, is present, in proportion from 5 to 25%.
• a supplementary softener e.g., 5% stearyl dimethyl amine oxide
• additional softening is observable.
• the articles washed espe cially those of nylon or polyester, exhibit a diminished tendency to accumulate static charges, with and without the use of the supplementary softener, builder and detergent.
• composition for the treatment of textiles consisting essentially of from 2-30% of a compound of the formula:
• R is alkenyl containing 1 or 2 double bonds or alkyl of 4 to 20 carbon atoms
• R and R are divalent alkylene or phenylene radicals of 1 to 9 carbon atoms
• X and Y are hydrogen or water-solubilizing salt forming elements or radicals selected from the group consisting of alkali metal, alkaline earth metal, ammonium, mono-alkanolamine, di-alkanolamine, tri-alkanolamine, mono-alkylamine, di-al'kylamine and tri-alkylamine in which the alkyl and alkanol group contain from 1 to 4 carbon atoms, the remainder to make up being essentially inorganic or organic salt builder.
• composition according to claim 1 additionally containing from 0.1 to 25% of detergent selected from the group consisting of anionic, cationic, amphoteric and nonionic detergents.
• composition according to claim 1 wherein the builder is an inorganic salt builder.
• composition according to claim 4 wherein R is a linear alkyl radical, terminally joined to the rest of the molecule and R and R are of 1 to 2 carbon atoms.
• composition according to claim 7 wherein the builder salt is an alkali metal phosphate.
• composition according to claim 8 which is in particulate solid form and which comprises from 10 to of said compound and to 45% of sodium tripolyphosphate.
• a composition according to claim 8 which is in liquid form and which comprises from 5 to 20% of said compound, 10 to tetrapotassium pyrophosphate and from to water.
• a method for laundering textiles which comprises washing said textiles with a composition as defined in claim 1 and wherein the washing treatment is at a temperature of 30 to C. and at a concentration of one part of said composition to 500 to 25,000 parts of water and at a pH of 8 to 10.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Materials Engineering (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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• 0
  • BE BE759533D patent/BE759533A/xx unknown
• 1969
  • 1969-11-28 US US00880909A patent/US3728385A/en not_active Expired - Lifetime
  • 1969-11-28 US US00880991A patent/US3755435A/en not_active Expired - Lifetime
  • 1969-11-28 US US00880992A patent/US3725473A/en not_active Expired - Lifetime
  • 1969-11-28 US US880977A patent/US3700607A/en not_active Expired - Lifetime
  • 1969-11-28 US US00880915A patent/US3726797A/en not_active Expired - Lifetime
• 1970
  • 1970-11-03 CA CA097,293A patent/CA942458A/en not_active Expired
  • 1970-11-06 CA CA097,622A patent/CA941557A/en not_active Expired
  • 1970-11-06 CA CA097,621A patent/CA941556A/en not_active Expired
  • 1970-11-11 GB GB5368970A patent/GB1319130A/en not_active Expired
  • 1970-11-21 DE DE19702057355 patent/DE2057355A1/de active Pending
  • 1970-11-24 FR FR7042106A patent/FR2099030A5/fr not_active Expired
  • 1970-11-25 CH CH1264774A patent/CH569695A5/xx not_active IP Right Cessation
  • 1970-11-25 CH CH1742970A patent/CH558332A/xx not_active IP Right Cessation
  • 1970-11-30 NL NL7017496A patent/NL7017496A/xx unknown
• 1973
  • 1973-01-17 US US324314A patent/US3864389A/en not_active Expired - Lifetime

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