Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/62—Quaternary ammonium compounds
  • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
  • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
  • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
• • 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
  • C11D1/38—Cationic compounds
  • C11D1/62—Quaternary ammonium compounds

Definitions

• the present invention generally relates to improved multiple hydrophilic/hydrophobic functional quaternary ammonium compounds "multiple functional" surfactants, useful in detergents and personal care, mining, industrial, and catalyst products, in biocidal compositions at higher concentrations, and as emulsifiers.
• Gemini surfactants Conventional surfactants have one hydrophilic group and one hydrophobic group. Dime c surfactants which are commonly called “Gemini” surfactants are those which comprise two hydrophilic functional groups and two hydrophobic functional groups. Gemini surfactants have unique physical properties resulting from constraint of two hydrophilic groups in close proximity and the consequent micellar properties, which has led to an intensive study of Gemini surfactants as detergents, softeners, emulsifiers, phase transfer catalysts, biocides, and as components in skin care lotions, hair conditioning compositions and cosmetics compositions. Their use is also being investigated in ore flotation, oil well drilling and in other industrial applications.
• the present invention generally relates to several new classes of cationic multiple functional surfactants and to compositions containing same The invention also relates to various processes for preparing the multiple functional surfactants of the present invention
• the present invention generally relates to multiple functional surfactants of the formulae l-IV, below, to compositions containing same and to methods for their preparation
• the beneficial features of the multiple functional surfactants of the present invention derive from their multiple functional character, i e , the chemical species of the present invention contain two or more hydrophobic groups and two or more hydrophilic groups in each molecule I.
• R 1 and R 2 are the same or different and are selected from straight or branched chain, substituted or unsubstituted C r C 22 alkyl or alkenyl groups wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage, or mixtures thereof;
• R 3 , R 4 , R 5 ,and R 6 are the same or different and are selected from straight or branched chain, substituted or unsubstituted C r C 22 alkyl or alkenyl groups wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage, or mixtures thereof; and
• A is a spacer selected from the group consisting of :
• each of x, y and z can independently be an integer of 1-20; and n is an integer of from 1-20;
• R 7 , R 8 ,R 9 , R 10 R 11 ? R 12 ,R 13 , and R 14 are the same or different and are selected from straight or branched chain, substituted or unsubstituted C C 22 alkyl or alkenyl groups, wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage, or mixtures thereof; and A is a spacer group as defined above, and wherein x, y and z are each independently an integer of 1-20; and n is an integer of from 1-20; or
• R, 5 and R 20 are different and are selected from straight or branched chain, substituted or unsubstituted C 8 -C 22 alkyl or alkenyl groups wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage, or mixtures thereof;
• R 16 , R 17 , R 18 and R 19 are the same or different and are selected from straight or branched chain, substituted or unsubstituted C r C 22 alkyl or alkenyl groups wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage, or mixtures thereof and n is an integer of from 1-20
• R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , and R 28 are the same or different and are selected from straight or branched chain, substituted or unsubstituted C,-C 22 alkyl or alkenyl groups, wherein said alkyl or alkenyl groups optionally contain at least one ester linkage, at least one amide linkage or mixtures thereof, and where x an y are each independently an integer of from 1-20 and n is an integer from 0-20, wherein in each of I, II, III and IV, Z is an anion
• R 1 : R 2 , R 7 , R 14 , R 15 and R 20 are preferably selected from C 8 -C 18 alkyl groups, optionally containing an ester linkage It is also preferred that x, y and z are 0-5 and that n is 1- 10
• R 21 and R 25 are preferably selected from 2- ethylhexyl nonyl-alkyl, or a C 13 -C 15 mixed alkyl group
• R, and R 2 be selected from 2- ethylhexyl, nonyl-alkyl, a C 13 - C 15 mixed alkyl group, or from the group consisting of dodecylalkyl, hexadecylalkyl, octadecylalkyl, oleylalkyl, cocoalkyl, soyaalkyl, tallowalkyl, or hydrogenated tallowalkyl , that R 3 , R 4 , R 5 and R 6 be
• each of R 7 , R 8 , R 9l R 10 , R proposition R 12 , R 13 and R 14 are independently selected from from methyl, ethyl, propyl, 2-ethylhexyl, nonyl-alkyl, a C 13 - C 15 mixed alkyl group, or from the group consisting of dodecylalkyl, hexadecylalkyl, octadecylalkyl, oleylalkyl, cocoalkyl, soyaalkyl, tallowalkyl, or hydrogenated tallowalky, and that n be an integer of from 1 to 5.
• R 20 be selected from methyl, ethyl, propyl, 2-ethylhexyl, nonyl-alkyl, a C 13 - C 15 mixed alkyl group, or from the group consisting of dodecylalkyl, hexadecylalkyl, octadecylalkyl, oleylalkyl, cocoalkyl, soyaalkyl, tallowalkyl, or hydrogenated tallowalky or other long chain fragment with the proviso that the group of substituents on one N + be not identical to the group of substituents which surround the other N + center and that n is an integer of from 1 to 20
• ester or amide containing multiple functional compounds of the present invention exhibit enhanced biodegradability which is extremely desirable for obvious environmental reasons
• enhanced biodegradability is a desired attribute in fabric softening compositions and in other uses where the content and volume of waste water effluent streams needs to be controlled
• the compounds of the present invention are preferably delivered to the textile to be softened in amounts effective to impart the desired softness and/or anti-static properties to said text ⁇ le(s)
• Said effective amount typically ranges in an amount of from about 0 5 to 3 grams of softening compound(s) per average load of laundry
• the compounds of the present invention can be formulated into liquid softening compositions, solid formulations and/or solid articles
• a liquid formulation the compounds of the present invention are dissolved and/or suspended in water, wherein said formulation optionally also contains other conventional softeners as well as other ingredients and diluents such as detergents, optical b ⁇ ghteners, viscosity aids, soil release agents, fragrance, and the like, in the requisite amounts so to provide an effective amount of the compounds of the present invention to the textile to be treated
• the multiple functional surfactants of the present invention are formed into small flowable particles or beads on a water-soluble carrier such as a solid detergent, which is optionally compounded with builders b ⁇ ghteners fragrance and the like
• the multiple functional surfactants of the present invention can be combined with a distribution agent and applied, or coated on a solid carrier such as a woven, or non-woven fabric or bonded polyester sheet Alternatively, the composition can be inserted into a container designed for insertion into a clothes dryer
• the present invention also relates to various methods for the preparation of multiple functional surfactants
• the multiple functional surfactants of formula I which contain ester spacer groups can be prepared by reacting a diaikylaikanol amine of formula
• n is an integer of from 1-12, to form a reaction mixture, or a diester of same, and thereafter quaternizing the reaction mixture
• the diaikylaikanol amine is preferably prepared by ethoxylating a fatty amine compound of the formula
• the fatty amine compound is selected from the group consisting of dodecylamine, hexadecylamine, octadecylamine, oleylamine, cocoalkylamine, soyaalkylamine, tallowalkylamine, hydrogenatedtallowalkyl amine, dicocoalkylamine, ditallowalkylamine, dihydrogenated tallowalkylamine d ⁇ octadecylam ⁇ ne,and mixtures thereof
• the dicarboxylic acid employed is preferably selected from the group consisting of oxalic, malonic, succinic, glutanc, adipic, maleic, fumanc and mixtures thereof.
• the multiple functional surfactants of formula I which contain an amine-functional spacer group can be prepared in the reaction of an N- alkylamino fatty amine compound
• the multiple functional quaternary ammonium compounds of Formula IV can be prepared by reacting a bis-primary amine alkane (e g , hexamethylenediamine) with two equivalents of aldehyde, e g., 2- ethylhexanal, or other long chain aldehydes such as nonanal or mixed C 13 -C 15 aldehydes (which are commercially available)
• a bis-primary amine alkane e g , hexamethylenediamine
• aldehyde e g., 2- ethylhexanal
• other long chain aldehydes such as nonanal or mixed C 13 -C 15 aldehydes (which are commercially available)
• R is a saturated or unsaturated hydrocarbon group, with aldehyde, e g., 2-ethylhexanal, or longer chain aldehyde such as nonanal or mixed C 13 -C 15 aldehydes (which are commercially available), or an alcohol
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• aldehyde e g., 2-ethylhexanal
• the cationic gemini and related multiple functional hydrophilic/hydrophobic functional compounds of the present invention can be employed alone, or in combination with typical surfactants, including mono-quaternary ammonium compounds
• typical surfactants including mono-quaternary ammonium compounds
• CMC Critical Micelle Concentration
• a composition was prepared comprising 90% Arquad® 12 (available from Akzo Nobel Chemicals Inc , Chicago, IL) and 10% of the compound of example 1 This composition exhibited a 50 fold reduction of CMC values compared to a composition comprising 100% Arquad® 12
• Example 2 Preparation of Multiple Functional Quaternary Ammonium Compound in Reaction of Aldehyde with Alkyl-diamine reaction of 1.6- hexanediamine with mixed C ⁇ /C ⁇ aldehyde, followed by reduction, methylation. and quaternization
• the product was a pale yellow liquid (400 g.)
• Asymmetric dimeric- or higher oligome c surfactant compounds are prepared from Duomeen®, Triameen®, and Tetrameen® compounds available from Akzo Nobel Chemicals Inc., Chicago, IL, using an amine- aldehyde condensation reaction.
• Example 4 Preparation of Multiple Functional Quaternary Ammonium Compound in the reaction of bis(hexamethylene)triamine with mixed C 13 /C 15 aldehyde, followed by reduction, methylation. and quatemization 1.
• the mixed aldehydes were added in portions to melted bis(hexamethylene)triamine; and the exothermic reaction was cooled.
• the reaction mixture was washed with water, then solvent removed by evaporation to yield the bis-imine mono -secondary amine compound, a pale yellow liquid.
• Dimenc - or higher multiple functional surfactant compounds with amide groups in the spacer groups are prepared from Duomeen®, T ⁇ ameen®, and Tetrameen® compounds from Akzo Nobel Chemicals, Inc in the following manner
• R coco-, tallow- or oleylalkyl
• Example 10 Preparation of Multiple Functional Amidoamine Quaternary Ammonium Compounds: Reaction of Duomeen CD with dimethylsuccinate to form bis-Duomeen CD succinate [a bisfsecondary amido-secondary amine) compound]
• Step 1 Reaction of a primary fatty amine compound with formaldehyde will form the hexahydrotriazine intermediate
• Step 2 hexahydrotriazine is reduced to form secondary amine
• Step 3 secondary amine is ethoyxlated to form alcohol amine compound; RNH(Me) + ethylene oxide ⁇ RN(Me)CH 2 CH 2 OH
• Step 4 two equivalents of ethoxylated amine react with dicarboxylic acid to form Gemini tertiary amine;
• Step 5 Gemini tertiary amine quaternized in reaction with methylating agent (methyl chloride or methylsulfate).
• step 2 Ethoxylation of long chain amino compound (see Example 7, step 1 )
• step 3 Reaction of ethoxylated amine compound II with dicarboxylic acid I, (see Example 7, step 2)

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

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• 1999
  • 1999-12-30 JP JP2000591141A patent/JP2003505339A/ja active Pending
  • 1999-12-30 KR KR1020017008425A patent/KR20010101352A/ko not_active Application Discontinuation
  • 1999-12-30 EP EP99967773A patent/EP1147158A1/en not_active Withdrawn
  • 1999-12-30 WO PCT/US1999/031246 patent/WO2000039241A1/en not_active Application Discontinuation
  • 1999-12-30 CA CA002357756A patent/CA2357756A1/en not_active Abandoned
  • 1999-12-30 BR BR9916711-5A patent/BR9916711A/pt not_active Application Discontinuation
  • 1999-12-30 AU AU23995/00A patent/AU771929B2/en not_active Ceased
  • 1999-12-30 CN CNB998159409A patent/CN1227321C/zh not_active Expired - Fee Related
• 2001
  • 2001-06-29 ZA ZA200105408A patent/ZA200105408B/en unknown
• 2002
  • 2002-04-24 HK HK02103069.8A patent/HK1043383A1/zh unknown

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