US3849341A - Ester-linked derivatives of carbohydrates as builders for detergent compositions - Google Patents

Ester-linked derivatives of carbohydrates as builders for detergent compositions Download PDF

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Publication number
US3849341A
US3849341A US00222659A US22265972A US3849341A US 3849341 A US3849341 A US 3849341A US 00222659 A US00222659 A US 00222659A US 22265972 A US22265972 A US 22265972A US 3849341 A US3849341 A US 3849341A
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Prior art keywords
starch
detergent
sodium
builder
ester
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Expired - Lifetime
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US00222659A
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English (en)
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V Lamberti
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Lever Brothers Co
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Lever Brothers Co
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Publication date
Priority to GB4516171A priority Critical patent/GB1355998A/en
Priority to DE19712148279 priority patent/DE2148279A1/de
Priority to CH1412871A priority patent/CH565858A5/xx
Priority to CA124,145A priority patent/CA967841A/en
Priority to NL7113475A priority patent/NL7113475A/xx
Priority to US00222659A priority patent/US3849341A/en
Application filed by Lever Brothers Co filed Critical Lever Brothers Co
Priority to DE2304057A priority patent/DE2304057A1/de
Priority to CH127973A priority patent/CH579138A5/xx
Priority to GB455573A priority patent/GB1415797A/en
Priority to NL7301349A priority patent/NL7301349A/xx
Priority to US387835A priority patent/US3910880A/en
Application granted granted Critical
Publication of US3849341A publication Critical patent/US3849341A/en
Anticipated expiration legal-status Critical
Assigned to ALPHATEC SPINE, INC., ALPHATEC HOLDINGS, INC., ALPHATEC INTERNATIONAL LLC, ALPHATEC PACIFIC, INC. reassignment ALPHATEC SPINE, INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: DEERFIELD PRIVATE DESIGN FUND II, L.P., DEERFIELD PRIVATE DESIGN INTERNATIONAL II, L.P., DEERFIELD SPECIAL SITUATIONS FUND, L.P., DEERFIELD SPECIAL SITUATIONS INTERNATIONAL MASTER FUND, L.P.
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/226—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B3/00—Preparation of cellulose esters of organic acids
    • C08B3/12—Preparation of cellulose esters of organic acids of polybasic organic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B3/00—Preparation of cellulose esters of organic acids
    • C08B3/14—Preparation of cellulose esters of organic acids in which the organic acid residue contains substituents, e.g. NH2, Cl
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C08B31/02—Esters
    • C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives thereof

Definitions

  • Eutrophication can be defined as a natural process of enrichment of waters with nutrients, such as phosphorus and nitrogen, at a slow rate. Eutrophication can be detrimental, since it may cause increased algal growth and algal scums which are unaesthetic, odorous, distasteful and often clog filters of water treatment plants.
  • ester-linked carboxylate derivatives of alkyl glycosides, di-, oligoand poly-saccharides as builders in accordance with the present invention not only permit the reduction or replacement of existing phosphate and nitrogen-containing builders in detergent compositions without sacrificing detergency efficiency, but in addition, afford a detergent composition containing a builder which is completely biodegradable.
  • compositions containing builder compounds which can be synthesized from low cost raw materials at reasonable prices and are biodegradable.
  • Still another object of the present invention is to provide new organic compounds which may be utilized as builders in detergent compositions.
  • ester-linked carboxylate derivatives of carbohydrates particularly polysaccharides, such as sucrose, lactose, maltose, cellobiose, rafiinose, starches, cellulose, glycogen, hemi-celluloses, pectins, alginates and gums and carbohydrate derivatives such as alkyl glycosides can serve as effective detergent builders in detergent compositions.
  • the builders employed in accordance 'with the present invention can be generally described as derivatives of alkyl, glycosides, di-, oligoand poly-saccharides having the general formula FormulaI bH-O wherein A is COOM or CH OR; R is hydrogen or a carboxylate ester moiety of the formula M is an alkali metal, ammonium or substituted ammonium cation; X is phenylene, or an alkyleneoxyalkylene moiety or a straight or branched chain alkylene or alkylene group of 2-4 carbon atoms; R is R, an alkyl group containing one to four carbon atoms or an aor fl-fructose moiety having the structure wherein R is as defined above; 12 is an integer of from about 1-10,000 and wherein the average number of carboxylate ester moieties is at least 0.5 per monomeric unit.
  • the aforementioned compounds can be substituted in detergent compositions for existing builders containing phosphorus or nitrogen without impairing the e
  • the builder salts (Formula I) of the invention may be generally described as ester-linked carboxylate derivatives of carbohydrates formed by reacting an alkyl glycoside, a di-, oligoor polysaccharide with a cyclic anhydride and subsequently neutralizing the resulting acid ester with an appropriate base to form the desired esterlinked carboxylate derivative.
  • typical representative members of the aforementioned group of compounds include the maleate, succinate, phthalate, glutarate, adipate, citraconate, itaconate, dilactate and diglycolate ester salts of a di-, oligoor poly-saccharide such as sucrose, hydrolyzed starch, starch, cellulose, glycogen, semicellulose, alginic acid, and of an alkyl glucoside such as methyl or ethyl glucoside.
  • a di-, oligoor poly-saccharide such as sucrose, hydrolyzed starch, starch, cellulose, glycogen, semicellulose, alginic acid, and of an alkyl glucoside such as methyl or ethyl glucoside.
  • the builders used in the invention may be prepared by heating the particular ca bohydrate with a cyclic anhydride in a suitable solvent such as toluene or pyridine and, after solvent removal, purified by washing either with water or dilute mineral acid.
  • anhydride value is controlled by the ratio of the anhydride to starting carbohydrate used.
  • An aqueous solution or slurry of the acid ester is then neutralized to a pH of -8-8.'6 with the desired base: e.g. sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, lithium carbonate, ammonium hydroxide, tetramethylammonium hydroxide, monoethanolamine, diethanolamine, triethanolamine and morpholine to form the corresponding alkali metal, ammonium or substituted ammonium salts.
  • the acid ester may be purified by first dissolving in water and neutralizing to pH 8.0 with an alkali metal bicarbonate or carbonate, evaporating to dryness and then extracting with a lower alcohol (e.g. methanol or ethanol) to separate the desired product.
  • a lower alcohol e.g. methanol or ethanol
  • the anhydroglucose unit depicted bove (Formula I) is linked as in cellobiose and may contain from about 250-2500 cellobiose units per molecule. Accordingly, it should be understood that when the degree of substitution or D.S. value (i.e., number of R groups per monomeric unit) is stated, it is the average number of R groups per anhydroglucose unit that is intended in the cases of cellulose and starch.
  • the repeating unit is even more complex and consists of a 8(1-4) linked anhydro-D-mannuronic acid and anhydro-L-gluuronic acid moiety.
  • the average number of R groups per anhydromonosaccharide unit is intended.
  • the degree of substitution or esterification is deferred to by the average number of ester carboxylate moieties attached per anhydromonosaccharide unit.
  • a degree of substitution of 0.5 indicates that, on the average, for every 100 anhydromonosaccharide units in the molecule, there are 50 ester carboxylate moieties in the complex arrangement described above.
  • the D.S. value refers to the total number of hydroxyl groups substituted by ester carboxylate moieties per molecule.
  • the D.S. value may be as high as 4 in the alkyl glycoside derivatives and as high as 8 in the disaccharide derivatives.
  • the degree of substitution or esterification can be readily determined by those skilled in the art, such as by titrating the acid ester with standard alkali. 7
  • Any carbohydrate, especially polysaccharides, containing hydroxy groups may be used as a starting material for forming the derivatives used in the present invention including such substances as the (C to C alkyl glycosides, exemplified by methyl and ethyl glucopyranosides; disaccharides, exemplified by sucrose, lactose, maltose and cellobiose; trisaccharides such as rafiinose; oligosaccharides, exemplified by those obtainable by enzymatic hydrolysis of corn starch and cellulose, polysaccharides, exemplified by glycogen, starches such as those derived from corn, potato, rice, arrowroot, tapioca, wheat, sago, etc., cellulose, hemicelluloses, polyuronic acids, dextrans, pectins, alginic acid and natural gums such as arabic and acacia as well as any of the aforementioned carbohydrates that may be
  • compositions of the present invention are alkali metal, alkanolammonium (i.e., mono-, diand tri-ethanolammonium), ammonium and mixtures thereof. Those especially preferred are sodium, potassium and triethanolammonium, although any cation which will solubilize the carbohydrate ester salt is suitable for use in the present invention.
  • the builder salts described above can be used singularly, in combination with each other as the sole builder in the detergent composition or in combination with other builders such as sodium nitrilotriacetate, sodium ethylenediaminetetraacetate, sodium tripolyphosphate, sodium and potassium pyrophosphate, sodium carbonate, sodium polyacrylate, oxidized starches, trisodium citrate and trisodium carboxymethyloxysuccinate.
  • the only essential ingredients are the detergent surface ac tive material and the builder salt.
  • the weight percent of the builder present in the detergent composition will range from about 5 to about and preferably from about 20 to about 60% and more preferably 35-50% by weight of the total weight of the composition.
  • the builders used in the instant invention will generally 'be present in a ratio of about 1:10 to about 10:1, and preferably 2:1- 5:1 depending on the end use or whether a heavy-duty or light-duty detergent is desired.
  • the ratio of builder to detergent may be as high as 50:1.
  • ester carboxylate derivatives of the polysaccharides described in the present invention may also be used as antiredeposition agents in detergent compositions.
  • the ester carboxylate polysaccharide derivative is generally present in minor amounts in relation to the total weight of the composition.
  • the polysaccharide derivatives of the invention will gen erally comprise up to 5% (preferably 13%) of the total Weight of the detergent composition.
  • the detergent surface active compounds which can beused in the compositions of this invention include anionic, nonionic, zwitterionic, ampholytic detergent compounds and mixtures thereof. These suitable substances are outlined-at length below.
  • Anionic detergent compositions which can be used in the compositions of this invention include both soap and non soap detergent compounds.
  • suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C -C
  • Particularly useful are the sodium or potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap and tall oil soap.
  • anionic organic non-soap detergent compounds are the water soluble salts, alkali metal salts of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.
  • alkyl is the alkyl portion of higher acyl radicals.
  • Nonionic synthetic detergents may be broadly defined as compounds which do not ionize in water solution.
  • a well-known class of nonionic synthetic detergents is made available on the market under the trade name of -Pluronic. These compounds are formed by condensing ethylene oxide with an hydrophobic base formedby the condensation of propylene oxide with propylene glycol.
  • the hydrophobic portion of the molecule which, of course, exhibits water insolubility has a molecular weight of from about 1,500 to 1,800.
  • the addition of polyoxyethylene radcals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the product is retained up to the point Where polyoxyethylene content is about 50% of the total weight of the condensation product.
  • nonionic synthetic detergents include:
  • the polyethylene oxide condensates of alkylphenols, e.g., the condensation products of alkylphenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to 5 to 25 moles of ethylene oxide per mole of alkylphenols.
  • the alkyl substituent in such compounds may be derived from polymerized propylene, di-isobutylene, octene, dodecene or nonene, for example.
  • R R R N Long chain tertiary amine oxides corresponding to the following general formula, R R R N 0, wherein R is an alkyl radical of from about 8 to 18 carbon atoms and R and R are each methyl, ethyl or hydroxy ethyl radicals.
  • the arrow in the formula is a conventional representation of a semi-polar bond.
  • amine oxides suitable for use in this invention include dimethyldodecylamine oxide, dimethyloctylamine oxide, dimethyldecylamine oxide, dimethyltetradecylamine oxide and dimethylhexadecylamine oxide, N-bis(hydroxyethyl)dodecylamine oxide.
  • dimethyldodecylphosphine oxide dimethyltetradecylphosphine oxide, ethylmethyltetradecylphosphine oxide, cetyldimethylphosphine oxide, dimethylstearylphosphine oxide, cetylethylpropylphosphine oxide, diethyldodecylphosphine oxide, diethyltetradecylphosphine oxide,
  • suitable sulfoxide compounds are:
  • Ampholytic synthetic detergents can be broadly described as derivatives of aliphatic secondary and tertiary amines, in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group. Examples of compounds falling within this definition are sodium-3- dodecylaminopropionate and sodium-3-dodecylaminopropane-sulfonate and sodium N-Z-hydroxydodecyl-N-methyl-taurate.
  • Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quaternary ammonium compounds, sulfonium compounds and phosphonium compounds in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group. Examples of compounds falling within this definition are 3-- (N,N-dimethyl-N-hexadecylammonio)propane l sulfonate.
  • Examples of compounds falling within this definition are 3- N,N-dimethyl-N-hexadecylammonio propane- 1 sulfonate, 3-(N,N-dimethyl-N-hexadecylarnmonio)-2 hydroxypropane-l-sulfonate, 3-(dodecylmethylsulfonium) propane sulfonate, and 3-(cetylmethylphosphonium)ethane sulfonate.
  • optional ingredients may also be added.
  • the optional ingredients are perfumes, colorants, fabric softening agents, fungicides, germicides, enzymes, fluorescent dyes, antiredeposition agents, hydrotropes and in the case of liquid compositions, opacifiers and organic solvents.
  • Other ingredients such as bleaches, i.e., sodium perborate with or without activators, active chlorine compounds, and inorganic salts such as sodium carbonate, sodium bicarbonate, sodium sulfate, sodium chloride and sodium silicate may also be present.
  • the detergent compositions of the present invention can be utilized in washing solutions over a pH range of from about 7-11 and more preferably 8-10.
  • Tables I-VIII further illustrate the present invention.
  • the detergent formulations set forth in the Tables represent detergent compositions containing representative classes of surface active ingredients in combination with builders of the present invention and also standard phosphate and nitrogen-containing builders.
  • the compositions were prepared by blending together the recited components in the proportions indicated, including an anticorrosion agent and buffering agent (sodium silicate) and adjusting the pH where necessary by the addition of sodium hydroxide.
  • the compositions were then tested for detergency or cleaning ability in the Terg-O-Torneter test wherein washing conditions are as indicated and the results reported as detergency units.
  • the average detergency units (DU) of the formulation is the final reflectance value of the washed cloth minus the initial reflectance of the soiled cloth (the average of two runs), the reflectance values being obtained by measurement with a Gardner automatic color difference meter, Model AC-3.
  • Adduct of a modified OXO-type Ctr-C15 alcohol with an average of 11 moles of ethylene oxide i.c., N eodol 45-11 available from Shell Chemical Company.
  • ester-linked carboxylate derivatives of carbohydrates used in the present invention may be eifectively used as builders in detergent compositions containing all classes of synthetic surface active agents, either as the sole detergent building agent or in combination with phosphorus-containing or nitrogen-containing detergent builders.
  • the'D.S. value By increasing or lowering the ratio of succinic anhydride to sucrose the'D.S. value can be correspondingly increased or decreased.
  • a detergent composition comprising:
  • an organic biodegradable detergent builder comprising a water soluble salt of an ester-linked carboxyl derivative of a polysaccharide, selected from the group consisting of starch maleate, starch succinate, starch phthalate, starch glutarate, starch citraconate, starch itaconate, starch diglycolate and starch dilactate wherein the D.S. value ranges from about 0.5-3 and wherein said builder represents from about 20% to about 60% of the total weight of the detergent composition and the weight ratio of builder to surfactant is from about 1:10 to about 50:1.
  • a detergent composition comprising:
  • an organic biodegradable detergent builder comprising a water soluble salt of an ester-linked carboxyl derivative of oligosaccharide selected from.
  • hydrolyzed starch maleate hydrolyzed starch succinate
  • hydrolyzed starch phthalate hydrolyzed starch glutarate
  • hydrolyzed starch citraconate hydrolyzed starch itaconate
  • hydrolyzed starch diglycolate hydrolyzed starch dilactate
  • said builder represents from about 20% to about 60% of the total weight of the detergent composition and the weight ratio of builder to surfactant is from about 1:10 to about 50:1.
  • composition of Claim 2 wherein the detergent is a nonionic surface active agent is a nonionic surface active agent.
  • composition of Claim 1 wherein the biodegradable detergent builder is an ester salt of a starch derived from corn, potato, rice, arrowroot, tapioca, wheat or sago.
  • composition of Claim 2 wherein the biodegradable detergent builder is an ester salt of a hydrolyzed starch derived from corn, potato, rice, arrowroot, tapioca, wheat or sago.
  • composition of Claim 1 wherein the biodegradable detergent builder is a salt of sodium, potassium, lithium, ammonia, monoethanolamine, diethanolamine, triethanolamine or morpholine.
  • a composition of Claim 2 wherein the biodegradable detergent builder is a salt of sodium, potassium, lithium, ammonia, monoethanolamine, diethanolamine, triethanolamine or morpholine.
  • a composition of Claim 1 wherein the biodegradable detergent builder is a starch succinate.
  • a composition of Claim 1 wherein the biodegradable detergent builder is sodium corn starch succinate.
  • a composition of Claim 1 wherein the biodegradable detergent builder is a starch maleate.
  • a composition of Claim 1 wherein the biodegradable detergent builder is a starch phthalate.
  • a composition of Claim 1 wherein the weight ratio of builder to surfactant is from about 1:10 to about :1.
  • a composition of Claim 1 wherein the weight ratio of builder to surfactant is from 2:1 to 5:1.
  • composition of Claim 2 wherein the weight ratio of builder to surfactant is from about 1:10 to about 18.
  • a composition of Claim 2 wherein the wegiht ratio of builder to surfactant is from 2:1 to 5:1.
  • a composition of Claim 1 wherein the biodegradable detergent constitutes 35 to by weight of the total weight of the composition.

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US00222659A 1970-09-30 1972-02-01 Ester-linked derivatives of carbohydrates as builders for detergent compositions Expired - Lifetime US3849341A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB4516171A GB1355998A (en) 1970-09-30 1971-09-28 Builders for detergent compositions
DE19712148279 DE2148279A1 (de) 1970-09-30 1971-09-28 Geruststoffe fur Detergensmittel
CH1412871A CH565858A5 (enrdf_load_stackoverflow) 1970-09-30 1971-09-29
CA124,145A CA967841A (en) 1970-09-30 1971-09-30 Builders for detergent compositions
NL7113475A NL7113475A (enrdf_load_stackoverflow) 1970-09-30 1971-09-30
US00222659A US3849341A (en) 1970-09-30 1972-02-01 Ester-linked derivatives of carbohydrates as builders for detergent compositions
DE2304057A DE2304057A1 (de) 1970-09-30 1973-01-27 Gerueststoffe fuer detergensmittel
CH127973A CH579138A5 (enrdf_load_stackoverflow) 1970-09-30 1973-01-30
GB455573A GB1415797A (en) 1970-09-30 1973-01-30 Detergent compositions
NL7301349A NL7301349A (enrdf_load_stackoverflow) 1970-09-30 1973-01-31
US387835A US3910880A (en) 1970-09-30 1973-08-13 Sulfosuccinate derivatives of carbohydrates

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US7705270A 1970-09-30 1970-09-30
US22264872A 1972-02-01 1972-02-01
US00222659A US3849341A (en) 1970-09-30 1972-02-01 Ester-linked derivatives of carbohydrates as builders for detergent compositions

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US (1) US3849341A (enrdf_load_stackoverflow)
CA (1) CA967841A (enrdf_load_stackoverflow)
CH (2) CH565858A5 (enrdf_load_stackoverflow)
DE (2) DE2148279A1 (enrdf_load_stackoverflow)
GB (2) GB1355998A (enrdf_load_stackoverflow)
NL (2) NL7113475A (enrdf_load_stackoverflow)

Cited By (23)

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Publication number Priority date Publication date Assignee Title
US3919107A (en) * 1973-03-23 1975-11-11 Procter & Gamble Built detergent compositions containing dextrin esters of poly carboxylic acids
US3941771A (en) * 1973-08-22 1976-03-02 Fmc Corporation Dextrin carboxylates and their use as detergent builders
US3989683A (en) * 1973-07-19 1976-11-02 Olin Corporation Method of treating karaya gum
US4021376A (en) * 1972-05-17 1977-05-03 Lever Brothers Company Detergent compositions with nonphosphate builders containing two or more carboxyl groups
US4029590A (en) * 1973-08-22 1977-06-14 Fmc Corporation Dextrin carboxylates and their use as detergent builders
US4087371A (en) * 1971-12-23 1978-05-02 Grillo-Werke Aktiengesellschaft Method of preventing incrustation on heated surfaces, and composition for the practice of the method
US4095991A (en) * 1975-01-31 1978-06-20 Rhone-Poulenc Industries Enhancement of heteropolysaccharide solubility
US4107425A (en) * 1977-02-15 1978-08-15 The United States Of America As Represented By The Secretary Of Agriculture Preparation of 1-α- and 1-β-glucose esters by stereoselective acylation of metalated 2,3,4,6,-tetra-O-benzyl-D-glucopyranose
US4151304A (en) * 1976-11-05 1979-04-24 Lever Brothers Company Method and composition for moisturizing the skin
US5069808A (en) * 1989-04-29 1991-12-03 Kali-Chemie Ag Washing or detergent composition containing lactobionic acid or lactobionic acid salts
US5264422A (en) * 1986-06-30 1993-11-23 Fidia S.P.A. Esters of alginic acid with steroidal alcohols
US5336668A (en) * 1986-06-30 1994-08-09 Fidia, S.P.A. Esters of alginic acid
US5559226A (en) * 1991-04-12 1996-09-24 The Procter & Gamble Company Process for making polyol fatty acid polyesters having oxidative stability
US5576020A (en) * 1991-11-15 1996-11-19 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Adjuvant for pharmaceutical preparations
US5763381A (en) * 1995-09-13 1998-06-09 National Starch And Chemical Investment Holding Corporation Starched-based adjuncts for detergents
US20060046962A1 (en) * 2004-08-25 2006-03-02 Aegis Therapeutics Llc Absorption enhancers for drug administration
US20090163447A1 (en) * 2004-08-25 2009-06-25 Maggio Edward T Compositions for Drug Administration
US20100160378A1 (en) * 2008-12-22 2010-06-24 Aegis Therapeutics Llc Compositions for drug administration
US8895546B2 (en) 2009-03-27 2014-11-25 Hale Biopharma Ventures, Llc Administration of benzodiazepine compositions
US9895444B2 (en) 2004-08-25 2018-02-20 Aegis Therapeutics, Llc Compositions for drug administration
US10046025B2 (en) 2006-06-23 2018-08-14 Aegis Therapeutics, Llc Stabilizing alkylglycoside compositions and methods thereof
US10265402B2 (en) 2004-08-25 2019-04-23 Aegis Therapeutics, Llc Absorption enhancers for drug administration
US11241414B2 (en) 2008-03-28 2022-02-08 Neurelis, Inc. Administration of benzodiazepine compositions

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR76286B (enrdf_load_stackoverflow) * 1981-09-28 1984-08-04 Procter & Gamble
GB8522621D0 (en) * 1985-09-12 1985-10-16 Unilever Plc Detergent powder
IT1213330B (it) * 1986-08-28 1989-12-20 Rol Spa Tensioattivi derivati da idrossiacidi bi- o tri-carbossilici.
DE3706015A1 (de) * 1987-02-25 1988-11-17 Henkel Kgaa Fluessiges reinigungsmittel
US5047168A (en) * 1988-01-21 1991-09-10 Colgate-Palmolive Co. Sugar ethers as bleach stable detergency boosters
US4889651A (en) * 1988-01-21 1989-12-26 Colgate-Palmolive Company Acetylated sugar ethers as bleach activators and detergency boosters
IT1247516B (it) * 1991-04-24 1994-12-17 Auschem Spa Tensioattivi derivati da esteri solfosuccinici
FR2682679B1 (fr) * 1991-10-17 1995-06-16 Seppic Sa Nouveaux derives d'alkylpolyosides, leurs procedes de preparation et applications comme agents de surface.
NO20073834L (no) 2006-07-21 2008-01-22 Akzo Nobel Chemicals Int Bv Sulfonerte podede kopolymerer
BRPI0918871A2 (pt) * 2008-09-19 2019-09-24 Procter & Gamble composição detergente contendo biopolímero modificado para reforço e estabilização de espuma.
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US4021376A (en) * 1972-05-17 1977-05-03 Lever Brothers Company Detergent compositions with nonphosphate builders containing two or more carboxyl groups
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US4095991A (en) * 1975-01-31 1978-06-20 Rhone-Poulenc Industries Enhancement of heteropolysaccharide solubility
US4151304A (en) * 1976-11-05 1979-04-24 Lever Brothers Company Method and composition for moisturizing the skin
US4107425A (en) * 1977-02-15 1978-08-15 The United States Of America As Represented By The Secretary Of Agriculture Preparation of 1-α- and 1-β-glucose esters by stereoselective acylation of metalated 2,3,4,6,-tetra-O-benzyl-D-glucopyranose
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US5576020A (en) * 1991-11-15 1996-11-19 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Adjuvant for pharmaceutical preparations
US5644012A (en) * 1991-11-15 1997-07-01 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Adjuvant for pharmaceutical preparations
US5854368A (en) * 1991-11-15 1998-12-29 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Adjuvant for pharmaceutical preparations
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US8268791B2 (en) 2004-08-25 2012-09-18 Aegis Therapeutics, Llc. Alkylglycoside compositions for drug administration
US20090163447A1 (en) * 2004-08-25 2009-06-25 Maggio Edward T Compositions for Drug Administration
US11173209B2 (en) 2004-08-25 2021-11-16 Aegis Therapeutics, Llc Compositions for drug administration
US20060046962A1 (en) * 2004-08-25 2006-03-02 Aegis Therapeutics Llc Absorption enhancers for drug administration
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US8927497B2 (en) 2004-08-25 2015-01-06 Aegis Therapeutics, Llc. Absorption enhancers for intranasal administration
US10265402B2 (en) 2004-08-25 2019-04-23 Aegis Therapeutics, Llc Absorption enhancers for drug administration
US9642913B2 (en) 2004-08-25 2017-05-09 Aegis Therapeutics, Llc. Pharmaceutical composition including alkyl glycoside and an anti-seizure agent
US9895444B2 (en) 2004-08-25 2018-02-20 Aegis Therapeutics, Llc Compositions for drug administration
US10046025B2 (en) 2006-06-23 2018-08-14 Aegis Therapeutics, Llc Stabilizing alkylglycoside compositions and methods thereof
US9763876B2 (en) 2008-03-28 2017-09-19 Hale Biopharma Ventures, Llc Administration of benzodiazepine compositions
US11241414B2 (en) 2008-03-28 2022-02-08 Neurelis, Inc. Administration of benzodiazepine compositions
US11793786B2 (en) 2008-03-28 2023-10-24 Neurelis, Inc. Administration of benzodiazepine compositions
US12268664B1 (en) 2008-03-28 2025-04-08 Neurelis, Inc. Administration of benzodiazepine compositions
US9283280B2 (en) 2008-12-22 2016-03-15 Aegis Therapeutics, Llc Compositions for drug administration
US8440631B2 (en) 2008-12-22 2013-05-14 Aegis Therapeutics, Llc Compositions for drug administration
US20100160378A1 (en) * 2008-12-22 2010-06-24 Aegis Therapeutics Llc Compositions for drug administration
US8895546B2 (en) 2009-03-27 2014-11-25 Hale Biopharma Ventures, Llc Administration of benzodiazepine compositions
US12324852B2 (en) 2011-06-14 2025-06-10 Neurelis, Inc. Administration of benzodiazepine compositions
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Also Published As

Publication number Publication date
GB1415797A (en) 1975-11-26
CA967841A (en) 1975-05-20
DE2148279A1 (de) 1972-04-06
CH565858A5 (enrdf_load_stackoverflow) 1975-08-29
DE2304057A1 (de) 1973-08-09
CH579138A5 (enrdf_load_stackoverflow) 1976-08-31
NL7301349A (enrdf_load_stackoverflow) 1973-08-03
NL7113475A (enrdf_load_stackoverflow) 1972-04-05
GB1355998A (en) 1974-06-12

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