US3728385A - N-oxide-iminodicarboxylates - Google Patents

N-oxide-iminodicarboxylates Download PDF

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US3728385A
US3728385A US00880909A US3728385DA US3728385A US 3728385 A US3728385 A US 3728385A US 00880909 A US00880909 A US 00880909A US 3728385D A US3728385D A US 3728385DA US 3728385 A US3728385 A US 3728385A
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compounds
salt
carbon atoms
oxide
acid
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H Wixon
B Sundby
E Kenney
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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

  • N-OXIDE-IMINODICARBOXYLATES [75]- Inventors: Bjorn Sundby, Piscataway; Edward J. Kenney, Bemardsville; Harold E. Wixon, New Brunswick, all of NJ.
  • kaline earth metal other suitable salt-forming rnetah ammonium, alkylamine or alkanolamine, which may be the same as or different from any other X in the formula, with it being understood that in the case of divalent or trivalent Xs it may be joined to a plurality of the shown organic moieties through the carboxylic oxygen(s) thereof.
  • novel compounds are possessed of surface activity and are substantive to fibrous materials, e.g., cotton and wool. They may be used as detergents or components of detergent compositions and serve as softeners for fibrous materials.
  • This invention relates to novel N-oxides of aminocarboxylates or aminocarboxylic acids in which an amino hydrogen is substituted by a 2-hydroxyalkyl group and either an alkyl-group or a hydrocarbyl carboxylate or acid.
  • Such compounds have been found to be useful surface active agents and are substantive to various fibrous materials. Thus, they serve as: emulsifiers for oils, to form oil-in-water emulsions; solubilizing agents for lipophilic materials; wetting agents; detergents; and softeners for textiles.
  • compositions made included additional ingredients which added their functions to those of the detergent constituent.
  • builders or surface active materials improved the detergency of the principal detergent constituent.
  • synergistic combinations of detergents were discovered. Although such combination products are useful and many have been successfully marketed, efforts have been made to improve laundering operations further by compounds which in themselves possess favorable qualities, in addition to their detersive abilities. Thus, attempts have been made to create detergents which clean and at the same time sequester the hardness ions of various types of hard waters. Even when such products were successful, it was often found that further work had to be done to make them into detergents useful to wash well in both hard and soft waters.
  • the present invention is of compounds which have effective detergent action, making them useful in removing dirt or various stains from clothing or other articles to be laundered, while at the same time, in a preferred aspect of the invention, they are sufiiciently substantive to various textiles to cause deposition on the textiles and retention thereon of the detergent or a portion of it, which serves to soften the textile, giving it a feel that is pleasant to the touch.
  • softeners have been used in treating textiles but usually they are deposited on the textile by immersing it in a solution of the softening compound after completion of the washing operation. In cases where such compounds are applied earlier, the softeners must possess sufficient substantivity to allow a part thereof to remain on the textile and have its effects discernible to the user after washing. It is generally observed that detergents oppose the deposition of substantivematerial on textiles and usually only small fraction of the substantive material.
  • the present compounds possess significant detersive properties and in preferred embodiments, are substantive to textiles and impart a soft hand thereto. Additionally, they are generally low foaming materials and may possess anti-static properties, both of which characteristics are often highly desirable in detergent-softeners for textiles.
  • RICH(OH)CHZI%RBCOOX which are effective detergents and which preferably also serve to soften fibrous materials when applied to them, as in aqueous solutions of the compounds.
  • R is an aliphatic hydrocarbon radical of four to 20 carbon atoms
  • R is a hydrocarbon radical of one to four carbon atoms or is R COOX
  • R is a divalent aliphatic or aromatic hydrocarbon radical-of one to nine carbon atoms
  • X is hydrogen, alkali metal alkaline earth metal or suitable salt-forming metal or may be ammonium, alkylamine or alkanolamine, either mono-, dior tri-alkylamine or '-alkanolamine.
  • the alkyl and alkanol groups of the salt-forming amines are of one to four carbon-atoms, preferably two to three carbon atoms. Both R and X may be the same or different from any other R or X in the compounds. or X in the compounds. It should be understood that X signifies a monovalent element or radical or a bond or valence of a divalent or trivalent element or radical. In preferred compounds X is hydrogen, alkali metal or other monovalent ion.
  • R is R COOX
  • the product is an N-oxideiminodicarboxylate of the formula mooox n -cmomcm-ig-mcoox
  • Preferred embodiments of the invention are those amine oxides of the formula previously given wherein R is an aliphatic hydrocarbon radical of eight to l4'carbon atoms, R is an aliphatic hydrocarbon radical of one to two carbon atoms or is R COOX, R is a divalent aliphatic hydrocarbon radical of one to three carbon atoms, X is hydrogen or a monovalent salt forming ion which is either an alkali metal, ammonium, mono-, di
  • the preferred compounds mentioned above are found to be excellent textile softeners, especially for cotton articles washed with them, even in the presence of builders and after normal rinsing.
  • the most preferred compounds are the salts-of N-(Z-hydroXy-higher alkyl)-N-methyl glycine- N-oxides and the N-(Z-hydroxy-higher alkyl)- aminodiacet'ic acid-N-oxides, -N-oxides, wherein the higher alkyl is of 12 to 16 carbon atoms and is of straight 'chain structure.
  • the iminodiacetic acid compounds and the N-methyl glycine compounds mentioned the more effective for the softening of cotton-textiles are the N-methyl glycines.
  • N-butylamine salt N (2- hydroxy 2,2-dimethyl-ethyl)- iminodiacetic acid-N-oxide, mono-n-propanolamine ide, disodium salt; N-(2-hydroxy-n-hexyl)-iminodi-npropionic acid-N-oxide,-monopotassium salt; N-(2- hydroxy-6-ethyl-n-decyl)-iminodi n-butyric acid-N-oxide, di-triethanolaminesalt; N-(2-hydroxydodecyl)- ir ninod'i-p-benzoic acid-N-oxide, magnesium salt; N-(2- I '-hydroxyhexadecyl-) iminoacetic-pr'opionic acid-N-ox- N-( 2-hydroxyoctadecenyl)- 1 magnesium salt; iminobenzoic-toluic acid-N-oxide, di is
  • the compounds not be substituted but the substituted compounds are often of utility similar to those which 'are literally within the formulas given.
  • mixed salts may be employed, as may be acid salts.
  • the salt-forming metal or other radical, if divalent or polyvalent, may be joined to both acid portions of the imino compounds.
  • a single salt-forming ion may be joined to two molecules of the acids of this invention.
  • R should be a short chain material
  • R v is'preferably a short chain 'alkylene,.usually of one to two carbon atoms, but ithas been found that longer chain alkylenes and evendivalent hydrocarbyl-faromatic compounds make useful products.
  • X .while.it may be hydrogen
  • the salt-formingions those which aremonovaleht are preferred,because of their generally greater water solubility, an important feature in the use of the present compounds. However, even though water solubility may be low, other, salts can be employed as. washing agents in other polar media, and
  • e'ven may be useful in an aqueous medium.
  • novel compounds of this invention may -,beprepared by oxidation of the corresponding amine;-
  • the N-( Z-hydroxyalkyl)-arninocarboxylicacidfor -iminodicarboxylic acid or salt thereof maybe treated -with' an oxidizing agent, such as hydrogen peroxide or ozone, preferably in aqueous solution, and the .water remaining after the reaction may be removed by any suitable technique, e-.g., freeze drying.
  • an oxidizing agent such as hydrogen peroxide or ozone
  • reaction will be' run in an aqueous solution of a soluble salt of-the-starting material an'd'will be'cohducted'by slowly admixing the oxidizingjagent 'withthe solutionof saltl at-a temperature about roo'm temperature; with g I cooling to'mairi tain such temperature or one slightlyhigher 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 1 hour, at a temperature of 15 to 50C. The solution may be held for an additional 30 minutes to 18 hours at a temperature of 40 to 90C., to decompose excess H but this can also be done with catalysts, such as platinum or palladium, or
  • 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 percent to 100 percent of the stoichiometric proportion, so as to aid in forcing the reaction and producing a 100 percent yield of the oxide. Of course, less than the stoichiometric proportion of oxidizing agent may be used, in which cases yields will suffer. It is normally not desirable to use less than 75 percent of the stoichiometric quantity of oxidizing agent, unless it is desired to make a mixture of the oxide or salt and the unoxidized aminocarboxylic acid or'iminodicarboxylic acid or salt.
  • the water soluble salt instead of utilizing the water soluble salt, a comparable reaction may berun with the acid, which may be solubilized by suitable solvents, e.g., ketones, such as acetone, methyl ethyl ketone.
  • suitable solvents e.g., ketones, such as acetone, methyl ethyl ketone.
  • the salts may be made by subsequent treatment of theacid oxides produced with alkaline material, e.g., NaOI-I, triethanolamine.
  • alkaline material e.g., NaOI-I, triethanolamine.
  • the acid forms of the oxide may be produced by acidification of previously manufactured salts.
  • N-(2-hydroxyalkyl)-N-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-(Z-I-Iydrox'y-Higher Hydrocarbyl)-N- Lower Hydrocarbyl-Aminocarboxylates and N-(2- Hydroxyhydrocarbyl) lminodicarboxylates, filed on the same day as this application.
  • 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 mixture, 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 be recrystallized from alcohol.
  • a solvent for these e.g., acetone. If desired, it may be recrystallized from alcohol.
  • the starting epoxides and aminocarboxylic acids or salts are well-known compounds and methods for their manufacture are obvious.
  • the present materials are normally employed in aqueous solution and are used either alone or with additives to make detersive solutions or emulsions and to act as wetting agents. They are also used to soften fabrics, especially cotton textiles.
  • the invented compounds usefully wash and soften textiles in the same operation.
  • the effectiveness of the invented materials, especially those most preferred, in softening textiles is very much unexpected, inasmuch as the present compounds help to release other materials which are adherent to the textile fibers.
  • the very softening effect obtained appears to depend upon substantivity of the invented compounds to the fiber. Also, such a substantivity appears to be effective with respect to vegetable and animal fibers, as well as various synthetic fibers. Therefore, the present compounds are highly advantageous for use in detergents and softening agents, and are especially suitable for use in combination detergent-softening compositions.
  • EXAMPLE 1 Fifteen parts of N-(2-hydroxydodecyl)-N-methyl glycine, sodium salt, are dissolved in 85 parts water and 7.0 parts of a 30% hydrogen peroxide solution in water are added slowly thereto. Such addition is dropwise, with both the glycine compound and the hydrogen peroxide being at 40C. After completion of the addition of the hydrogen peroxide'which takes about 5 minutes, the resulting aqueous solution is held at an average temperature of C. for four hours', with the temperature variation being between 70C. and C. during this time. At the end of the four hour period, the solution is tested for the presence of peroxide and a negative result is obtained.
  • the solution is frozen and water is removed from it by a freeze drying operation, at an absolute pressure of 3 millimeters of mercury.
  • the product remaining is a white, hygroscopic powder, identified as N-(2-hydroxydodecyl)-N-methyl glycine-N-oxide, sodium salt.
  • the yield obtained is 15.5 parts, almost the stoichoimetric amount.
  • corresponding oxides are made by utilizing ozone as a source of reactive oxygen. Again, addition is slow and the ozone may be diluted with inert gas so that it comprises from 5 to 50 percent by volume of such gas mixture.
  • ozone other oxygen-releasing compounds may be used, such as the per-compounds, e.g., sodium perborate, peracetic acid, urea hydrogen peroxide, and other known and suitable oxidizing agents useful for the making of amine oxides.
  • Such compounds are generally used in aqueous solution, with the proportion of available oxygen present corresponding 1 to that described in the above example.
  • N-(2-hydroxy-alkyl)-N-substituted carboxylic acids and salts are used in replacement of the specific compound shown in the above example.
  • N-(2-hydroxyhexadecyl)-N-methyl-aminotoluic triisopropylamine salt; and N-(2-hydroxydodecyl)-N-amyl-aminoacetic acid, calcium salt are employed in replacement of the 15 parts of N-(2- hydroxydodecyl)-N-methyl glycine, sodium salt, and corresponding oxidations are effected by following the procedure of Example 1, to make the respective salts.
  • N-(Z-hydroxyhexadecyl)-iminodi'acetic acid, disodium salt the sane using a stoichiometrically of N-(2-hydroxy-n-butyl)- equivalent amount -iminodipropionic acid, potassium salt; N-(2-hydroxy-6- ethyl-n hexadecyl)-iminoditoluic acid, ammonium salt; N-(2-hydroxy-N-decyl-imino-isopropyl-benzoic acid, triethanolamine salt; I or N-(2-hyd'roxyoctadecyl)- imino-acetic-propionicacid, magnesium salt; the corresponding N-'oxides are made.
  • additional water is added or a suitable solverit,le.g., ethanol, n-butanol, isopropanol, is addedafter completion of the reaction, when the M has been destroyed, to improve the fluidity of the product.
  • a suitable solverit le.g., ethanol, n-butanol, isopropanol
  • EXAMPLE 3 Fifty parts of N-(2-hydroxydodecyl)-N-methyl glycine, sodium salt, are dissolved in 150 parts water. 22 parts of a 30 percent squeous solution of hydrogen peroxide are added slowly at room temperature. A
  • salts used are those of potassium, triethanolamine,
  • the hydrogen peroxide may be removed by treatment with sodium sulfite, with just enough sodium sulfite being added to reduce the excess of hydrogen peroxide.
  • sodium sulfite such reducing agent would no'tbeemployed if the presence of sodium sulfate was objectionable in the product.
  • this chemical decomposition of excess hydrogen peroxide appears'to give a solution of improved color, as compared to the light yellow solution sometimes obtained when the peroxide is removed by thermal decomposition, as previously described.
  • the long chain alkyl groups of the hydroxy-alkyl are straight chain and terminally joined to the nitrogen, unless otherwise-indicated.
  • EXAMPLE 4 Although general utilities as surface active'agents, surface tension reducing agents, emulsifiers, detergents or softening agents for textiles have'been noted for the products of Examples l-3, especially useful softening and detersive' actions have been observed for those in Tables 1 and 2, below.
  • the softening effect test is one in which two grams of detergent material, made according to the methods of either Example 1 or Example 2, are blended with 6.6 grams of sodium tripolyphosphate and are used to wash one-half of a terrycloth hand towel, in three gallons of New Brunswick, New Jersey tap water (90 ppm. hardness), at 120F. The washing is carried out, using a General Electric washing machine with a Mini-basket attachment in the machine. In a similar manner, controlled softness formulations are employed and towels washed therewith are compared to those washed, using the experimentalsoftening compounds. The towels employed are of measurement 13 inches by 16 inches, purchased from J. C. Penney Company as 16 inch by 26 inch towels, which are cut in half for the present testing.
  • the softness of the towels washed by the various compositions is rated on the scale of l to 10, with 1 indicating a towel that 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.
  • the Spangler soil detergency tests are run using three cotton percale swatches, each 3 inches by 6 inches, .each soiled with Spangler soil (a mixture of airborne and sebum soils). Washing of the swatches is done in a Tergotometer evaluating washing machine. The washing is done at two hardnesses and two temperatures, as indicated.
  • the washing composition comprises percent of each of the mentioned experimental compounds, 35 percent sodium tripolyphosphate and 50 percent sodium sulfate. The concentration of the washing preparation employed is 0.15 percent,
  • R is alkyl or alkenyl of four to 20 carbon atoms, said alkenyl containing one or two double bonds, R is an alkylene or an aromatic hydrocarbon radical of one to nine carbon atoms and X is hydrogen, alkali metal, alkaline earth metal, ammonium, monoalkylamine, dialkylam ine, trialkylamine, monoalkanolamine, dialkanolamine or trialkanolamine, in which the alkyl and alkanol groups are of one to four carbon atoms.
  • R is a linear alkyl radical of 10 to 14 carbon atoms
  • R is methylene
  • X is alkali metal
  • R is linearalkyl of 14 carbon atoms, terminally joined to the rest of the compound, and X is sodium.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • 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)
US00880909A 1969-11-28 1969-11-28 N-oxide-iminodicarboxylates Expired - Lifetime US3728385A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US88091569A 1969-11-28 1969-11-28
US88097769A 1969-11-28 1969-11-28
US88098269A 1969-11-28 1969-11-28
US88090969A 1969-11-28 1969-11-28
US88099169A 1969-11-28 1969-11-28
US88099269A 1969-11-28 1969-11-28
US324314A US3864389A (en) 1969-11-28 1973-01-17 N-(2-Hydroxyhydrocarbyl) Iminodicarboxylates

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Application Number Title Priority Date Filing Date
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
US880977A Expired - Lifetime US3700607A (en) 1969-11-28 1969-11-28 Detergent compositions containing n-oxide-aminocarboxylates
US00880992A Expired - Lifetime US3725473A (en) 1969-11-28 1969-11-28 N-(2-hydroxyhydrocarbonyl) iminodicarboxylates
US00880991A Expired - Lifetime US3755435A (en) 1969-11-28 1969-11-28 N-(2-hydroxy-higher hydrocarbyl)-n-lower hydrocarbyl-aminocarboxylates
US324314A Expired - Lifetime US3864389A (en) 1969-11-28 1973-01-17 N-(2-Hydroxyhydrocarbyl) Iminodicarboxylates

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

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BE (1) BE759533A (cs)
CA (3) CA942458A (cs)
CH (2) CH569695A5 (cs)
DE (1) DE2057355A1 (cs)
FR (1) FR2099030A5 (cs)
GB (1) GB1319130A (cs)
NL (1) NL7017496A (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843029A (en) * 1995-10-16 1998-12-01 Gerber/Baby Care Manual breast pump

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888797A (en) * 1970-08-04 1975-06-10 Carapus Company Limited Detergent composition
US3888798A (en) * 1970-11-16 1975-06-10 Colgate Palmolive Co Liquid detergent composition
DE2111950A1 (de) * 1971-03-12 1972-11-23 Degussa Verwendung von Salzen bestimmter Hydroxyalkylaminosaeuren als waschaktive Substanzen
FR2208976B1 (cs) * 1972-11-30 1978-02-24 Modokemi Ab
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
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
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
US4129527A (en) * 1974-11-07 1978-12-12 The Clorox Company Liquid abrasive detergent composition and method for preparing same
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
DE2616800A1 (de) * 1976-04-15 1977-11-03 Henkel & Cie Gmbh Kosmetische reinigungsmittel
US4259249A (en) * 1979-06-13 1981-03-31 The Procter & Gamble Company Preparation of hydroxyl zwitterionic compounds
US4397776A (en) * 1981-03-17 1983-08-09 The Procter & Gamble Company Liquid detergent compositions containing alpha-amine oxide surfactants
US4359413A (en) * 1981-03-17 1982-11-16 The Procter & Gamble Company Solid detergent compositions containing alpha-amine oxide surfactants
OA06199A (fr) * 1981-05-13 1981-06-30 Berol Kemi Ab Procédé de flottation de minéraux phosphatés et composé destiné à ce procédé.
US4416792A (en) * 1981-11-12 1983-11-22 Lever Brothers Company Iminodipropionate containing detergent compositions
US4375422A (en) * 1981-11-12 1983-03-01 Lever Brothers Company Homogeneous detergent containing nonionic and surface active iminodipropionate
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
US4914232A (en) * 1982-04-12 1990-04-03 The B. F. Goodrich Company Polysubstituted 2-morpholones, related compounds, processes for their preparation, and U-V light stabilized compositions
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.
US5488130A (en) * 1995-03-31 1996-01-30 The Dow Chemical Company Amino nitrile intermediate for the preparation of 2-hydroxypropyl iminodiacetic acid
US7217069B2 (en) * 2000-02-10 2007-05-15 Eastway Fair Company Limited Hand-held tool with a removable object sensor
US7645731B1 (en) 2009-01-08 2010-01-12 Ecolab Inc. Use of aminocarboxylate functionalized catechols for cleaning applications

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2368604A (en) * 1943-02-08 1945-01-30 Shell Dev Anticorrosive
US2401196A (en) * 1944-06-02 1946-05-28 Commercial Solvents Corp Dicarboxylic salts of polyhydroxy tertiary amines
US2737523A (en) * 1952-10-30 1956-03-06 Upjohn Co N-(3-halo-2-hydroxypropyl)-p-aminobenzoate compounds
US2816920A (en) * 1955-08-11 1957-12-17 Gen Mills Inc Production of zwitterion of detergent amino acids
US2891053A (en) * 1955-12-20 1959-06-16 Bayer Ag Therapeutically valuable calcium salts
FR1146332A (fr) * 1956-03-29 1957-11-08 Produits de nettoyage de la chevelure et sels de diamines bitertiaires entrant dans la composition de ces produits
US3214413A (en) * 1960-05-12 1965-10-26 Metal Recovery Systems Chelating monomers and polymers of amino acids having a vinyl aryl nucleus
US3398097A (en) * 1965-07-30 1968-08-20 Progressive Products Co Cleaning composition, and method of cleaning and sequestering metal ions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Fieser, L. F. et al., Organic Chemistry, 3rd Edtn., pub. by Reinhold Pub. Corp. of N.Y. (1956), QD257F5, pg. 239 & 240 relied on. *
Finak, I. L., Organic Chemistry, Vol. I (1963), pub. by Richard Clay & Co. of Great Britain QD251F56, pg. 317 relied on. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843029A (en) * 1995-10-16 1998-12-01 Gerber/Baby Care Manual breast pump

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GB1319130A (en) 1973-06-06
US3864389A (en) 1975-02-04
NL7017496A (cs) 1971-06-02
BE759533A (fr) 1971-04-30
US3725473A (en) 1973-04-03
CA942458A (en) 1974-02-26
US3726797A (en) 1973-04-10
US3700607A (en) 1972-10-24
DE2057355A1 (de) 1971-07-22
CA941557A (en) 1974-02-12
CA941556A (en) 1974-02-12
US3755435A (en) 1973-08-28
CH558332A (de) 1975-01-31
CH569695A5 (cs) 1975-11-28
FR2099030A5 (cs) 1972-03-10

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