EP1294792A1 - Alcools organoleptiquement actifs lies a des polyesters biodegradables - Google Patents

Alcools organoleptiquement actifs lies a des polyesters biodegradables

Info

Publication number
EP1294792A1
EP1294792A1 EP01936407A EP01936407A EP1294792A1 EP 1294792 A1 EP1294792 A1 EP 1294792A1 EP 01936407 A EP01936407 A EP 01936407A EP 01936407 A EP01936407 A EP 01936407A EP 1294792 A1 EP1294792 A1 EP 1294792A1
Authority
EP
European Patent Office
Prior art keywords
alcohol
acid
fragrance
methyl
terminated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01936407A
Other languages
German (de)
English (en)
Inventor
Lars Zander
Thomas Otto Gassenmeier
Sandra Saladin
Wolfgang Denuell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1294792A1 publication Critical patent/EP1294792A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy 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
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3715—Polyesters or polycarbonates
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

  • the invention relates to biodegradable polyesters which release organoleptically active fragrance alcohols, a process for the preparation of these polyesters and their use in cosmetic compositions, plastic, adhesive, lacquer, detergent, fabric softener, detergent, hand dishwashing detergent and dishwasher detergent compositions for automatic dishwashers.
  • the disadvantage of this process is the immediate release of the fragrance from the formulation, which leads to a temporary fragrance effect and thus greatly reduces the storage stability of the formulation.
  • Attempts to encapsulate such substances or to include them in cyclodextrins proved to be unsuccessful or uneconomical due to the high raw material prices.
  • Immobilization by chemical derivatization proved to be more advantageous.
  • WO 95/04809 teaches the slow cleavage of fragrance alcohol esters by means of lipases, which produces a long-lasting fragrance.
  • WO 97/30687 and EP 816322 bind to sulfonates, sulfates and phosphates, with similar effects being achieved. Further possibilities for the targeted slow release of fragrance alcohols are betaine esters, as shown in EP 0799885, ⁇ -tertiary carbon esters in WO 98/07810, ⁇ -keto esters in WO 98/07813 or linear or cyclic acetals.
  • the present invention has for its object to provide new biodegradable classes of substances for the targeted release of fragrance alcohols.
  • the object is achieved according to the invention by chemically linking a fragrance alcohol component to a polyester backbone to form a fragrance alcohol-terminated polyester.
  • the invention relates to a fragrance-alcohol-terminated polyester obtainable by reacting a polyester backbone with an acid number of 10 to 750 (DIN 53402) and a fragrance alcohol.
  • the polyester backbone made of an organic polyester can be obtained by a) polycondensation of hydroxycarboxylic acids, b) esterification of di- or tricarboxylic acids with alcohols having 2, 3 or 4 hydroxyl groups.
  • polyester backbones are preferably made by
  • hydroxycarboxylic acids which have 1, 2 or 3 hydroxyl groups and 1 or 2 carboxylic acid groups and consist of 2 to 36 carbon atoms. Particularly preferred are those which are selected from the group consisting of citric acid, lactic acid, malic acid, tartaric acid, gluconic acid, ricinoleic acids, 4-hydroxypentanoic acid, 3-hydroxybutyric acid or mixtures thereof.
  • the starting substance for the polycondensation can also be the respective lactones, insofar as they exist.
  • di- or tricarboxylic acids containing 2 to 36 carbon atoms are particularly suitable for this.
  • Preferred di- or tricarboxylic acids are those selected from the group consisting of saturated or unsaturated aliphatic carboxylic acids or unsaturated alicyclic carboxylic acids and aromatic carboxylic acids.
  • Carboxylic acids which are selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid, terephthalic acid, isophthalic acid, agaricic acid, citric acid, 1,2 are particularly preferred , 3-propane tricarboxylic acid, hemimellitic acid, trimellitic acid, trimesic acid or mixtures thereof.
  • the diols and polyols suitable for forming the polyester backbones carry 2, 3 or 4 hydroxyl groups.
  • They are preferably selected from the group consisting of saturated and unsaturated aliphatic, saturated and unsaturated alicyclic and aromatic alcohols with 2 to 36 carbon atoms or polyalkylene glycols with an average molecular weight of 106 to 1000.
  • Particularly preferred are alcohols from the group consisting of ethylene glycol, Propylene glycol, butylene glycol, and neopentyl glycol, pentanediol-1,5,3-methylpentanediol-1,5, bisphenol A, 1, 2- or 1, 4-cyclohexanediol, caprolactone diol (reaction product from caprolactone and ethylene glycol), hydroxyalkylated bisphenols, trimethylol propane , Trimethylolethane, pentaerythritol, hexanediol-1, 6, heptanediol-1, 7, octanediol-1, 8, butanediol-1, 4, 2-
  • polyesters which can be used according to the invention have acid numbers (SZ) in the range from 10 to 750 (measured in accordance with DIN 53402), preferably 50 to 400, particularly preferably 150 to 350.
  • the fragrance alcohols are selected from the group consisting of amyl alcohol, 2-hexyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, myristic alcohol, 3-methyl-but-2-en-1-ol, 3-methyl-1 - pentanol, cis-3-hexenol, cis-4-hexenol, 3,5,5-trimethylhexanol, 3,4,5,6,6-pentamethylheptan-2-ol, citronellol, geraniol, oct-1-ene -3-ol, 2,5,7-trimethyl octan-3-ol, 2-cis-3,7-dimethyl-2,6-octadien-1-ol, 6-ethyl-3-methyl-5-octene 1-ol, 3,7-dimethyl-oct-3,6-dienol, 3,7
  • the fragrance alcohol-terminated polyesters according to the invention have the advantage that the fragrance alcohols contained are released by slow hydrolysis of the esters.
  • the compounds according to the invention have good biodegradability.
  • the invention also relates to a process for producing the fragrance alcohol-terminated polyesters according to the invention by esterifying the reaction of fragrance alcohols with polyester backbones with acid numbers from 10 to 750 (DIN 53402) under customary conditions for the formation of an ester.
  • the esterification can be carried out in bulk or in solution
  • any known esterification process can be used to produce the polyester backbones by polycondensation of hydroxycarboxylic acids or by esterification of the di- or tricarboxylic acids with the abovementioned alcohols, as well as the esterification of the backbones containing free carboxylic acid groups with the olfactory alcohols , So far be referred to the knowledge of the expert.
  • the esterification of the polyester backbones can take place completely or partially.
  • Another object of the invention is the use of the compounds according to the invention in cosmetic formulations such as deodorants, shampoos, creams, lotions, soaps, ointments, powders and aerosols, in detergents and cleaning agents, paints, plastics, adhesives, hand dishwashing detergents, dishwashing detergents for automatic dishwashers and fabric softeners ,
  • 0.1 to 10% by weight, preferably up to 5% by weight, of the compound according to the invention are added to such compositions.
  • the polyester thus obtained has an acid number of 687.
  • the reaction mixture obtained is then heated further under reflux with 250 g of citronellol (1.6 mol) on a water separator until a further 36 g of water (2 mol) have separated.
  • the raw product is neutralized and can then be used in formulations.
  • the initially odorless substance mentioned in synthesis example 2 is incorporated into a dishwashing formulation and tested in a commercially available dishwasher. After the end of the rinse, a pleasant scent of geraniol is noticed, which is still noticeable after 60 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des polyesters biodégradables qui libèrent des alcools aromatiques organoleptiquement actifs. Elle concerne également un procédé pour produire de tels polyesters ainsi que leur utilisation dans des compositions cosmétiques, de matières plastiques, colles, peintures, détergents, adoucissants, lessives, produits pour le lavage de la vaisselle à la main et en machine.
EP01936407A 2000-06-09 2001-05-30 Alcools organoleptiquement actifs lies a des polyesters biodegradables Withdrawn EP1294792A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE2000128763 DE10028763A1 (de) 2000-06-09 2000-06-09 Organoleptisch aktive Alkohole gebunden an bioabbaubare Polyester
DE10028763 2000-06-09
PCT/EP2001/006130 WO2001094442A1 (fr) 2000-06-09 2001-05-30 Alcools organoleptiquement actifs lies a des polyesters biodegradables

Publications (1)

Publication Number Publication Date
EP1294792A1 true EP1294792A1 (fr) 2003-03-26

Family

ID=7645348

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01936407A Withdrawn EP1294792A1 (fr) 2000-06-09 2001-05-30 Alcools organoleptiquement actifs lies a des polyesters biodegradables

Country Status (4)

Country Link
EP (1) EP1294792A1 (fr)
AU (1) AU6232101A (fr)
DE (1) DE10028763A1 (fr)
WO (1) WO2001094442A1 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5324612A (en) * 1991-10-03 1994-06-28 Toyo Boseki Kabushiki Kaisha Toner for electrophotography
EP1003469A2 (fr) * 1996-02-21 2000-05-31 Givaudan-Roure (International) S.A. Precurseurs de parfums
JPH11106629A (ja) * 1997-10-03 1999-04-20 Takasago Internatl Corp 香料含有徐放性生分解性樹脂組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0194442A1 *

Also Published As

Publication number Publication date
DE10028763A1 (de) 2001-12-20
WO2001094442A1 (fr) 2001-12-13
AU6232101A (en) 2001-12-17

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