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
  • C11D3/32—Amides; Substituted amides
  • C11D3/323—Amides; Substituted amides urea or 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
  • 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
• • 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
  • C11D3/2003—Alcohols; Phenols
  • C11D3/2065—Polyhydric 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
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/26—Organic compounds containing nitrogen
  • C11D3/32—Amides; Substituted amides

Definitions

• the present invention relates to the stability of quaternary ammonium materials, in particular it relates to maintaining stable quaternary ammonium materials containing at least one ester group in the raw material form or as a solution in a suitable solvent.
• Quaternary ammonium materials both solid or liquid are used extensively in fabric softener compositions.
• Such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of quaternary ammonium softening agent up to 8% by weight in which case the compositions are considered dilute or at levels from 8 to 50% in which case the compositions are considered concentrates.
• a problem associated with quaternary ammonium materials containing at least one ester group is their instability on storage.
• the problem is particularly noticeable in the storage of these materials at variable temperatures over time.
• EP 299 176 discloses soft-finishing agents comprising a di-long chained quaternary ammonium salt containing a single ester group and a decyldimethyl amine.
• US 4 937 008 discloses concentrated fabric softening agents comprising one or more quaternary ammonium salts and a di or tri-valent polyol with 2 to 3 carbon atoms.
• low and high temperature stability of solid or liquid quaternary ammonium compounds containing at least one ester group may be improved by the addition of one or more of a select group of stabilising agents which act to prevent the extent of decomposition of the quaternary ammonium material.
• stabilised compositions comprising quaternary ammonium material represented by the formula: wherein each R 1 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups; X - is any suitable counter-ion.
• T is and n is an integer from 1-5 or is 0 characterised in that they further comprise one or more stabilising agent(s) wherein the one or more stabilising agents are chosen from one or more of the group comprising:
• a second aspect of the present invention there is provided the step of adding at least one stabilising agent during the manufacture of the quaternary ammonium material, preferably following the quaternisation step in the synthesis of the quaternary ammonium material.
• composition as defined is incorporated into a solid and/or liquid rinse conditioner.
• a stabilising agent to reduce the level of discoloration of quaternary ammonium material containing at least one ester group.
• ester group' in the quaternary ammonium material includes an ester group which is a linking group in the molecule.
• References herein to quaternary ammonium material are to those having at least one ester group in their structure.
• the stabilising agent(s) are chosen from one or more of the following group comprising,
• compositions show improved stability at varying temperatures.
• ester-linked quaternary ammonium compounds The quaternary ammonium compounds containing at least one ester group are referred to herein as ester-linked quaternary ammonium compounds.
• the quaternary ammonium compounds contain two or more ester groups.
• the ester group(s) is a linking group between the nitrogen atom and an alkyl group.
• the ester groups(s) are attached to the nitrogen atom via another hydrocarbyl group.
• the invention is most useful for quaternary ammonium compounds containing two ester groups, wherein at least one higher molecular weight group containing at least one ester group and two or three lower molecular weight groups are linked to a common nitrogen atom to produce a cation and wherein the electrically balancing anion is a halide, acetate or lower alkosulphate ion, such as chloride or methosulphate.
• the higher molecular weight substituent on the nitrogen is preferably a higher alkyl group, containing 12 to 28, preferably 12 to 22, eg 12 to 20 carbon atoms, such as coco-alkyl, tallowalkyl, hydrogenated tallowalkyl or substituted higher alkyl, and the lower molecular weight substituents are preferably lower alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, or substituted lower alkyl.
• One or more of the said lower molecular weight substituents may include an aryl moiety or may be replaced by an aryl, such as benzyl, phenyl or other suitable substituents.
• the quaternary ammonium material used in the invention is a compound having two C 12 -C 22 alkyl or alkenyl groups connected to a quaternary ammonium head group via two ester links.
• the invention is useful for quaternary ammonium material comprising a compound having two long chain alkyl or alkenyl chains with an average chain length equal to or greater than C 14 . Even more preferably each chain has an average chain length equal to or greater than C 16 . Most preferably at least 50% of each long chain alkyl or alkenyl group has a chain length of C 18 . It is preferred if the long chain alkyl or alkenyl groups are predominantly linear.
• ester-linked quaternary ammonium material for use in the invention is represented by the formula: wherein each R 1 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups;
• X - is any suitable counterion, i.e. a halide, acetate or lower alkosulphate ion, such as chloride or methosulphate.
• T is and n is an integer from 1-5 or is 0
• each R 1 group is methyl and each n is 2 as such compounds are found to be particularly susceptible to the stability problems referred to above.
• Di (tallowyloxyethyl) dimethyl ammonium chloride available from Hoechst, is especially preferred, also Di(hardened tallowyloxyethyl) dimethyl ammonium chloride, ex Hoechst.
• the quaternary ammonium material is biologically degradable.
• n 1 or 2 and R 2 is C 12 -C 22 , especially C 16 -C 22 e.g. tallow.
• the quaternary ammonium compound used in the present invention is substantially anhydrous, meaning containing less than 10% water in the context of the present invention.
• the quaternary ammonium material may contain optional additional components, as known in the art, in particular, low molecular weight solvents, for instance isopropanol and/or ethanol, and co-actives such as nonionic softeners, for example fatty acid or sorbitan esters.
• low molecular weight solvents for instance isopropanol and/or ethanol
• co-actives such as nonionic softeners, for example fatty acid or sorbitan esters.
• the stabilising agent may be urea or a derivative thereof, a primary or secondary amide or a polyhydric alcohol, or mixtures thereof. Two or more stabilising agents may be used.
• the stabilising agent is added to the composition of the present invention at levels of 0.05 to 10% by weight of the weight of the quaternary ammonium material. However, lower amounts than this are preferred, more preferably 0.1 to 7.5% is added based on the weight of the quaternary ammonium material, especially 0.5 to 6.0% and even more preferably 0.5 to 4%.
• the stabilising agent may be introduced to the quaternary ammonium material at any stage during the manufacture of the quaternary ammonium material or after manufacture i.e. on storage.
• the stabilising agent may be added in any form, as a powder direct to the molten quaternary ammonium material or as a solution in a suitable solvent, for instance iso propanol.
• the addition step can take place during the synthesis of the quaternary ammonium material, preferably following the quaternisation step.
• the addition may take alternatively, or additionally, place during storage of the quaternary ammonium material.
• the stabilising agent is most effectively introduced at any stage following the quaternisation step of the synthesis of the quaternary ammonium material.
• amide to be used in the present invention is acetamide.
• Polyhydric alcohols such as glycerol may be used as stabilising agents.
• Another preferred stabilising agent is urea.
• a combination of glycerol and a quaternary ammonium compound of general formula (A) is particularly preferred, especially wherein both R 1 are CH 3 , n is 2 and R 2 is tallow.
• the stabilised composition is in a liquid, molten or semi-solid form containing less than 10% by weight water.
• a solid rinse conditioner comprising a stabilised composition as defined above, preferably a composition in a granular or powdered form.
• a liquid rinse conditioner comprising a stabilised composition as defined above.
• the reflectance was measured on a datacolor international Spectraflash SF600 plus reflectometer after 3 days storage at 82°C. R540 after 3 days at 82°C DEQ (control) 19.8 DEQ + 3.6% urea 25.1 DEQ + 7.3% urea 27.4 DEQ is di(2-[hardened tallow]oxyl oxyethyl) dimethyl ammonium chloride ex Hoechst. It includes approximately 10% mono ester and minor amounts of unquaternised amine/amine salt as well as approximately 2% fatty acid and 14% isopropanol.

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

Applications Claiming Priority (3)

Publications (2)

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• 1998
  • 1998-05-18 GB GBGB9810655.2A patent/GB9810655D0/en not_active Ceased
• 1999
  • 1999-05-12 AU AU41438/99A patent/AU732651B2/en not_active Ceased
  • 1999-05-12 ES ES99924984T patent/ES2234259T3/es not_active Expired - Lifetime
  • 1999-05-12 HU HU0101910A patent/HUP0101910A3/hu unknown
  • 1999-05-12 CN CNB998061689A patent/CN1192083C/zh not_active Expired - Fee Related
  • 1999-05-12 BR BRPI9910549-7A patent/BR9910549B1/pt not_active IP Right Cessation
  • 1999-05-12 DE DE69923175T patent/DE69923175T2/de not_active Expired - Lifetime
  • 1999-05-12 WO PCT/EP1999/003366 patent/WO1999060081A1/en not_active Ceased
  • 1999-05-12 RO ROA200001089A patent/RO121133B1/ro unknown
  • 1999-05-12 CA CA2325018A patent/CA2325018C/en not_active Expired - Fee Related
  • 1999-05-12 EP EP99924984A patent/EP1080171B1/en not_active Expired - Lifetime
  • 1999-05-12 JP JP2000549690A patent/JP2002515551A/ja not_active Withdrawn
  • 1999-05-12 TR TR2000/03386T patent/TR200003386T2/xx unknown
  • 1999-05-12 CZ CZ20004292A patent/CZ300743B6/cs not_active IP Right Cessation
  • 1999-05-12 RU RU2000131616/04A patent/RU2220190C2/ru not_active IP Right Cessation
  • 1999-05-12 PL PL99344240A patent/PL190329B1/pl not_active IP Right Cessation
  • 1999-05-18 AR ARP990102345A patent/AR016032A1/es active IP Right Grant
• 2000
  • 2000-11-17 ZA ZA200006734A patent/ZA200006734B/en unknown

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