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
  • C11D3/26—Organic compounds containing nitrogen
  • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
• • 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
  • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
• • 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
  • C11D1/66—Non-ionic compounds
  • C11D1/835—Mixtures of non-ionic with cationic compounds

Definitions

• the present invention relates to di-alkyl substituted imidazoline derivatives where the two alkyl groups are linked through an ester function to the imidazoline core.
• the di-alkyl substituted imidazoline derivatives of the present invention may also be used in compositions such as fabric care compositions and hair conditioning compositions.
• Di-alkyl substituted imidazoline compounds are known in the art. Oftentimes they are used as fabric softening and hair conditioning actives. However, other industrial applications include the use as antistatic and as corrosion inhibitor. Given their lower melting point, the di-alkyl substituted imidazoline derivatives can be stored and shipped without the need to add a dilution solvent, leading to important logistical cost savings. They are also non-corrosive, meaning construction material of lower grade metallurgy can be utilised for manufacturing, storage and shipment equipment. Nevertheless, di-alkyl substituted imidazoline derivatives are not readily biodegradable, which is an undesirable characteristic of this class of compounds.
• EP 345,842 A2 discloses di-alkyl substituted imidazoline derivatives which exhibit improved biodegradability; however, these have since been found to form persistent monoalkyl substituted break-down products. Therefore, only partial biodegradation can be achieved which is environmentally undesirable.
• JP05-105670 and JP06-228870 describe readily biodegradable di-alkyl imidazole derivatives.
• granular fabric softening compositions comprising a di-alkyl substituted imidazole derivative according to the formula of claim 1 offered a fabric softening composition in which the softening active is readily biodegradable, and is in a consumer accepted product form. Also, the fabric softening active can be shipped safely and easily, in the absence of a dilution solvent.
• a first aspect of the present invention is a granular fabric softening composition
• the present invention is to a granular fabric softening composition
• X 2 is a C2-3 alkylene group, more preferably a C2 alkylene group.
• X 2 is an isopropyl group.
• X 3 is a C1-4 alkylene group, more preferably, a CH 2 group.
• R 1 and R 2 are independently a C12-18 alkyl or a C12-18 alkenyl group.
• R 1 and R 2 are independently selected from the group comprising (hydrogenated) tallow fatty acid, palm fatty acid, hydrogenated palm fatty acid, oleic acid, rapeseed fatty acid, hydrogenated rapeseed fatty acid or mixtures thereof.
• These di-alkyl substituted imidazoline derivatives can also be called imidazoline diester compounds.
• the formation of persistent monoalkyl substituted imidazoline species is avoided by having two weak ester bonds, such that an intermediate of the formula I or II will be degraded in the environment to form III.
• the granular fabric softening composition can be used as an additive in a hand or machine rinse or can alternatively be used in a tumble drier application.
• the granular composition can be dispersed in water during or prior to use.
• the di-alkyl substituted imidazoline derivative is preferably present at a level from 70% to 99% by weight of the granular fabric softening composition.
• Fabric softener compositions comprising the di-alkyl substituted imidazoline derivative may optionally comprise other ingredients, preferably selected from the group comprising quaternary ammonium compounds, silicones compound, perfumes, encapsulated perfumes, dispersing agents, stabilizers, pH control agents, colorants, brighteners, dyes, odor control agent, pro-perfumes, cyclodextrin, solvents, soil release polymers, preservatives, antimicrobial agents, chlorine scavengers, anti-shrinkage agents, fabric crisping agents, spotting agents, anti-oxidants, anticorrosion agents, bodying agents, drape and form control agents, smoothness agents, static control agents, wrinkle control agents, sanitization agents, disinfecting agents, germ control agents, mold control agents, mildew control agents, antiviral agents, anti-microbials, drying agents, stain resistance agents, soil release agents, malodor control agents, fabric refreshing agents, chlorine bleach odor control agents, dye fixatives, dye transfer inhibitors, color
• Another aspect of the present invention is a method of synthesizing the di-alkyl substituted imidazoline derivative.
• a preferred synthesis method for making di-alkyl substituted imidazoline derivatives is as follows.
• a hydroxyl substituted polyalkylenediamine of the formula NH 2 -X 1 -NH-X 2 -OH is reacted with a hydroxyl substituted fatty acid of the formula OH-X 3 -COOH.
• the hydroxyl substituted polyalkylenediamine is N-(2-hydroxyethyl)-1,2-ethylenediamine.
• the hydroxyl substituted polyalkylenediamine is N-(2-hydroxyispropyl)-1,2-ethylenediamine.
• the hydroxyl substituted fatty acid is glycolic acid.
• the hydroxyl substituted polyalkylenediamine and the hydroxyl substituted fatty acid are mixed in the molten phase, and the reaction mixture is kept agitated and in the liquid phase.
• the molar ratio of hydroxyl substituted fatty acid to hydroxyl substituted polyalkylenediamine is preferably between 0.8:1 to 1.2:1, more preferably between 0.9:1 to 1:1.
• the reaction vessel is kept under an inert atmosphere, for example, by flushing it with N 2 gas.
• the reaction mixture of the first step is heated to a temperature of from 100°C to 240°C, preferably from 150°C to 210°C, most preferably from 180°C to 200°C.
• the reaction water is then removed from the reactor vessel, preferably by applying a vacuum.
• the resultant reaction mixture will then contain mainly a di-hydroxy substituted imidazoline of the formula; wherein X 1 is a C2-3 alkylene group, X 2 is a C1-6 linear or branched alkylene or alkenylene group, X 3 is a C1-6 linear or branched alkylene or alkenylene group and C is OH and D is OH.
• X 1 is CH2-CH2
• X 2 is CH2-CH2 or CH-(CH3)-CH2
• X 3 is CH2 and C is OH and D is OH.
• the di-hydroxy substituted imidazoline of step 2 is further reacted with an esterifying agent.
• the esterifying agent is preferably selected from the group comprising fatty acids, short chain, C1-4, esters of fatty acids and fatty acid glycerides.
• the molar ratio of esterifying agent to di-hydroxy substituted imidazoline is from 1.2:1 to 2.2:1, preferably from 1.5:1 to 2:1.
• the reaction mixture is heated to a temperature from 100°C to 200°C, preferably from 165°C to 190°C.
• the reaction water is then removed from the reactor vessel, preferably by applying a vacuum.
• the reaction is preferably kept under an inert atmosphere, at a pressure less than 1500 Pa, preferably less than 250 Pa.
• an esterification catalyst is used.
• the esterification catalyst is preferably selected from the group comprising metal alkoxides, metal halides, metal alkyl halides, metal carboxylate salts, metal alkyl alkoxides and mixtures thereof.
• the esterification catalyst is a metal alkoxide, preferably selected from the group comprising Sn(OR)4, Na(OR), K(OR) or Ti(OR)4, wherein R is a C1-6 alkyl group, preferably C2-3.
• the esterification catalyst is a metal halide, preferably selected from the group comprising tin halides or transition metal halides, preferably TiY4 where Y is Cl or Br.
• the esterification catalyst is a metal alkyl halide, preferably a transition metal alkyl halide.
• the esterification catalyst is a metal carboxylate salt, preferably selected from the group comprising tin acetate or zinc acetate.
• the esterification catalyst is a metal alkyl alkoxide, preferably selected from the group comprising transition metal alkyl alkoxides or tin alkyls such as SnT4 where T is independently a C1-8 hydrocarbyl group or a C1-8 hydroxyl group.
• Preferred di-alkyl substituted imidazoline derivatives of the present invention include;
• compositions comprising di-alkyl imidazoline derivatives include; Examples INGREDIENTS I II III IV V VI VII Imidazoline Di Ester a 75% 85% 95% Imidazoline Di Ester b 75% 85% Imidazoline Di Ester c 85% 90%
• Nonionic surfactant d 10% 8% 3% 12% 3% 10% 5%
• Deionized water Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Percentages are expressed as percentage by weight of the composition.
• Imidazoline diester reaction product of N-(2-hydroxyethyl)-1,2-ethylenediamine with glycolic acid, esterified with partially hardened tallow fatty acid.
• Imidazoline diester reaction product of N-(2-hydroxyethyl)-1,2-ethylenediamine with glycolic acid, esterified with fully hardened tallow fatty acid.
• Imidazoline diester reaction product of N-(2-hydroxyisopropyl)-1,2-ethylenediamine with glycolic acid, esterified with partially hardened palm fatty acid.
• Nonionic surfactant C12-14 alkyl, 10 Ethoxylate Anhydrous citric acid
• f Poly ethylene glycol MW 4000
• the above products are produced by spray-chilling a co-melt of the imidazoline compound with the nonionic surfactant.
• the atomized co-melt is agglomerated and perfume (and eventually dye solution, citric acid and other minors) are sprayed on during agglomeration.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Cosmetics (AREA)

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Citations (3)

• 2010
  • 2010-04-13 EP EP10159737A patent/EP2264013A1/fr not_active Withdrawn
  • 2010-05-13 CN CN2010800204719A patent/CN102421758A/zh active Pending
  • 2010-05-13 MX MX2011012132A patent/MX2011012132A/es not_active Application Discontinuation
  • 2010-05-13 BR BRPI1010825A patent/BRPI1010825A2/pt not_active IP Right Cessation
  • 2010-05-13 WO PCT/US2010/034642 patent/WO2010132629A1/fr active Application Filing
  • 2010-05-13 CA CA2757177A patent/CA2757177A1/fr not_active Abandoned

Patent Citations (3)

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