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
  • C11D3/30—Amines; Substituted amines ; Quaternized amines
• • 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
  • C11D3/323—Amides; Substituted amides urea or derivatives thereof

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.
• the problem is particularly noticeable in the storage of these materials at variable temperatures over time, especially at elevated temperatures eg in the region of 40-90°C, such as 50-85°C.
• the amount of discolouration is generally an indication of the level of decomposition occurring over time. This decomposition is of greatest concern when quaternary ammonium material is stored at temperatures above their melting points.
• Instability may also manifest itself by alkyl halide appearance in the sample, indicating decomposition of the quaternary ammonium material. Instability may be referred to as caused by, or indicated by, de-quaternisation of the quaternary ammonium material.
• EP 299 176 discloses soft-finishing agents comprising a di-long chained quaternary ammonium salt containing a single ester group and a decyldimethyl amine.
• EP 499 282 discloses compositions comprising a quaternary ammonium compound and an aliphatic amine.
• EP 332 270 discloses compositions comprising a quaternary ammonium fabric softening agent, an amine and an amphoteric material.
• US 5282983 discloses aqueous fabric softener compositions comprising a softener material obtained by neutralising a di-long chain type tertiary amine compound.
• EP 0547723 (Colgate-Palmolive) discloses free-flowing spraydried particulate fabric softening compositions comprising 45 to 85% by weight of urea.
• low and high temperature stability of the aforementioned solid or liquid quaternary ammonium compounds may be improved by the addition of at least one stabilising agent selected from specific group of compounds which improve the stability of the composition.
• improved stable compositions comprising a quaternary ammonium material of formula where each R 1 group is methyl; and each R 2 group is tallowyl; X - is chloride, T is and n is 2 characterised in that they further comprise one or more stabilising agent(s) chosen from;
• compositions show improved stability at varying temperatures.
• a process of stabilising the aforementioned quaternary ammonium material by the addition of one or more stabilising agents as defined above, at levels as defined above.
• a solid rinse conditioner comprising a composition as defined above.
• liquid rinse conditioner made by dilution of a composition as defined above with water.
• a further aspect of the invention is provided a method of reducing the alkyl halide levels in the aforementioned quaternary ammonium material over time by the addition of a stabilising as defined herein, at levels as defined herein.
• the quaternary ammonium materials of the invention preferably do not contain substantial amounts of non- ester containing material.
• the ester containing quaternary ammonium material is used in the absence of non-ester group quaternary ammonium containing material.
• small amounts eg less than 20% by weight based on the amount of total quaternary ammonium material, preferably less than 10% may be present.
• ester-linked quaternary ammonium material for use in the invention is represented by the formula: wherein each R 1 group is methyl; and wherein each R 2 group is tallowyl; X - is chloride T is and n is 2.
• 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.
• any of the above-mentioned stabilising agents may be used according to the invention.
• 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, more preferably 0.5 to 8.5% and even more preferably 0.75 to 7.5%, eg 1 to 5%.
• R 1 R 2 R 3 substituents include OCOR4 substituents wherein R 4 is a C 12 -C 22 alkyl or alkenyl chain.
• the most preferred stabilising agents are urea and tertiary amines where R 1 and R 2 are C 1 - C 2 alkyl groups and R 3 is a C 2 - C 4 hydroxyalkyl group eg N,N-dimethyl ethanolamine (DMEA).
• R 1 and R 2 are C 1 - C 2 alkyl groups and R 3 is a C 2 - C 4 hydroxyalkyl group eg N,N-dimethyl ethanolamine (DMEA).
• the stabilising agent may be introduced to the quaternary ammonium material at any stage during its manufacture or after manufacture, eg 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 isopropanol.
• the addition of the stabilising agent can take place during the synthesis of the quaternary ammonium material preferably following the quaternisation step.
• the addition may alternatively, or additionally, be made 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.
• composition is in a liquid, molten or semi molten form containing less than 10% by weight of water.
• These compositions may be incorporated into a solid rinse conditioner which is preferably in a powdered or granular form.
• the compositions may also be diluted with water to produce a liquid rinse conditioner.
• 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.
• Alkyl halide is produced by the following decomposition reaction: R 2 Me 2 N + Cl - ⁇ R 2 NMe+ MeCl R 1 Me 3 N + Cl - ⁇ R 1 NMe 2 + MeCl
• R is a C 8 to C 22 hydrocarbyl group, optionally interrupted by functional groups, e.g. ester [O-CO., CO.O], amide, ether, amine, carbonate), optionally branched, optionally unsaturated and R 1 is a C 8 to C 40 hydrocarbyl group similarly defined.
• the chloromethane levels were determined by capillary gas chromatography.
• Formulation MeCl (ppm) after 3 days at 82°C DEQ (control) 283 DEQ plus 3.6% urea 52 DEQ plus 7.3% urea 24 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.
• DMEA was added to the DEQ following storage of the DEQ overnight at 82°C. Chloromethane was determined by gas chromatography after a further day at 82°C. Formulation MeCl (ppm) after storage at 82°C DEQ (control) 80 (1 day) DEQ plus 0.76% DMEA 32 (1 day) DEQ plus 2.28% DMEA 5 (30 minutes) DEQ plus 2.28% DMEA 2 (1 day) DMEA is N,N-dimethylethanol amine (99% ex Aldrich)
• Glycerol was added at a level of 7.5% by weight to a sample of DEQ to produce example 4A.
• a control sample of DEQ which did not contain any glycerol (Comparative example 4B) and example 4A were sealed in separate Gas Chromatograph (GC) vials and were stored at 80.5°C. At the end of the storage period the level of 'total' methyl chloride in each sample was measured. The results are given below.
• the above results demonstrate the ability of the stabilising agent, here glycerol, to reduce the level of MeCl in a quaternary ammonium material on closed, high temperature, storage.
• the level of MeCl measured here is the 'total' level in a sealed system.

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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)

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• 1998
  • 1998-05-18 GB GBGB9810656.0A patent/GB9810656D0/en not_active Ceased
• 1999
  • 1999-05-12 HU HU0101902A patent/HUP0101902A3/hu unknown
  • 1999-05-12 EP EP99929121A patent/EP1080172B1/en not_active Expired - Lifetime
  • 1999-05-12 CA CA2329959A patent/CA2329959C/en not_active Expired - Fee Related
  • 1999-05-12 TR TR2000/03385T patent/TR200003385T2/tr unknown
  • 1999-05-12 AU AU46045/99A patent/AU4604599A/en not_active Abandoned
  • 1999-05-12 WO PCT/EP1999/003367 patent/WO1999060082A1/en active IP Right Grant
  • 1999-05-12 DE DE69925119T patent/DE69925119T2/de not_active Expired - Lifetime
  • 1999-05-12 ES ES99929121T patent/ES2241289T3/es not_active Expired - Lifetime
  • 1999-05-12 CN CN99806166.2A patent/CN1280389C/zh not_active Expired - Fee Related
  • 1999-05-12 BR BRPI9910550-0A patent/BR9910550B1/pt not_active IP Right Cessation
  • 1999-05-18 AR ARP990102346A patent/AR019556A1/es active IP Right Grant

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