WO2002004587A1 - Process for imparting conditioning and good fragrance perception to both damp and dry fabric - Google Patents
Process for imparting conditioning and good fragrance perception to both damp and dry fabric Download PDFInfo
- Publication number
- WO2002004587A1 WO2002004587A1 PCT/US2001/021334 US0121334W WO0204587A1 WO 2002004587 A1 WO2002004587 A1 WO 2002004587A1 US 0121334 W US0121334 W US 0121334W WO 0204587 A1 WO0204587 A1 WO 0204587A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fragrance
- aroma
- delivery vehicle
- process according
- mixture
- Prior art date
Links
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
- C11D3/50—Perfumes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
-
- 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
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D3/18—Hydrocarbons
Definitions
- Liquid conditioning products for treating substrates contain cationic materials as a key active ingredient.
- Other ingredients such as oils as described in WO 97/44424, may be used in liquid conditioning products together with a cationic active to aid in the deposition of fabric treatment agents. (See also WO98/16538, which is incorporated by reference as if recited in full herein.).
- oils as part of the conditioner, may be delivered during the final rinse.
- Escher uses hydrophobicity, determined as the partition coefficient of the chemical between octanol and water and expressed as log P. Similar to Muller' s disclosure that the higher the log P value, the greater the substantivity. Log P may be measured directly but more conveniently it may be calculated from the structure of the molecule, using one of several commercially available software programs, such as ACD Software, ACD/logP calculator version 4.0, Advanced Chemistry Development, Toronto, Ontario Canada. The calculated value is abbreviated to CLogP.
- Another way to impart good fragrance to a substrate is to have the substantive part of the fragrance composed of an aroma chemical with low perception thresholds.
- a variety of techniques are available to determine the perception threshold. See e.g., Neuener-Jehle and Etzweiler in Art Science and Technology, editors Lampaski and Muller, ch.6, 153-212 (1991).
- a fragrance must be composed of at least 70% aroma chemicals with a CLogP > 3.0 and a boiling point of >250°C at 760 mm Hg.
- Trihn, et al, U.S. Patent No. 5,833,999 uses the same criteria for defining enduring fragrances for hair and skin products.
- the active agents disclosed as conditioners by these patents are predominantly cationic, having at least one of the alkyl chains with a chain length at least equal to 12, preferably greater than 16.
- the level of cationic active used in the conditioner product depends upon whether the product is dilute or concentrated.
- the levels of active in dilute products ranges from l%(wt) to 7%(wt) and in concentrated products from 10%( t) to 20%(wt).
- optimum fragrancing of both damp and dry substrates has been difficult to achieve using the methods summarized above, which rely solely on water insolubility, boiling point, and perception threshold.
- a water insoluble oil when combined with a cationic active, provides excellent fragrance deposition and perception on both damp and dry substrates, such as fabrics or hair, so long as the fragrance composition is constructed according to the present invention.
- one embodiment of the invention is a process for conditioning and fragrancing damp and dry substrates.
- This process includes providing a fragrance delivery vehicle containing a conditioner having a cationic active at a level above 0.5%(wt), a water insoluble oil, and up to 5%(wt) of a fragrance composition, wherein the fragrance composition provides enhanced perception on dry treated substrates and maintains good perception on damp treated substrates when added to the final rinse of a washing process.
- This fragrance delivery vehicle includes a water insoluble oil, a conditioner containing a cationic active, and at least 0.1%(wt) of a fragrance composition consisting of at least 2 %(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg.
- the process according to the present invention includes providing a fragrance delivery vehicle containing a water insoluble oil, a cationic active in a fabric conditioner, and a fragrance composition to provide enhanced fragrancing of both damp and dry substrates, such as a fabric or hair.
- the fragrance delivery vehicle is then contacted with a substrate in an aqueous solution.
- the fragrance delivery vehicle is contacted with the substrate using any conventional method, such as for example by adding it to the rinse cycle of a conventional washing machine in the case of a fabric.
- the fragrance delivery vehicle is contacted with the substrate in an aqueous solution.
- the aqueous solution is water or a solution containing a substantial amount of water that is suitable for fabric or hair washing.
- substrate means hair or a fabric (natural, synthetic, or natural/synthetic blends) that is suitable for conventional washing and drying.
- the fragrance delivery vehicle contains a cationic active above
- the fragrance composition contains at least 2%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP greater than 4.0 and a vapor pressure of less than 0.01 mm Hg, preferably less than 0.008 mm Hg, at 25°C.
- the aroma chemical in the fragrance composition will have a perception threshold below 100 ng per liter at 25°C, preferably, a perception threshold below 50 ng per liter at 25°C, such as for example, a perception threshold below 30 ng per liter at 25°C.
- the CLogP and vapor pressure were calculated using ACD/CLogP calculator version 4.0 and ACD/Boiling Point calculator version 4.0, respectively, from Advanced Chemicals Development ACD/Labs Software (Toronto, Ontario, Canada).
- fabric conditioner means a product that imparts softness, drape, and other similar benefits, such as antistatic properties, color care properties, etc., to fabrics.
- hair conditioner means a product that imparts softness, easier combing, and shine to hair.
- conditioner is used throughout to refer to fabric conditioners, hair conditions, or both, as the context may dictate.
- aroma chemical as used herein means a chemical that is volatile and that is detected by the nose as a smell.
- perception threshold means the lowest quantity of an aroma chemical, in the vapor phase that may be perceived by the nose.
- the cationic active in the conditioning delivery vehicle may be, for example, dialkyldimethyl ammonium chloride, dialkyldimethyl ammonium methyl sulfate, di (hydrogenated tallow) dimethyl ammonium chloride, dihexadecyldiethylammonium chloride, distearyldimethylammonium chloride, dibehenyldimethylammoinium chloride, di(coconut alkyl)dimethyl ammonium chloride, ditallowdimethyl ammonium chloride, ester quaternium compounds, dialkylyloxy dimethyl ammonium chloride, N,N-di(tallowyl-oxy-ethyl)-N N- dimethylammonium chloride, N N-(ditallowoxyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, dialkyl imidazolium methyl sulfate, amido silicones, and mixtures thereof.
- the level of cationic active in a dilute f agrance delivery vehicle of the invention may be 0.5%(wt) - 7.0%(wt), preferably 0.75%(wt) - 6.0%(wt), such as for example, 1.0%(wt) - 5.0%(wt).
- Levels of the cationic active in a concentrated delivery vehicle of the invention may be from 7%(wt) to 20%(wt), preferably 10%(wt) to 15%(wt).
- the water insoluble oils of the fragrance delivery vehicle may be selected from, for example, mineral oils, ester oils, sugar ester oils or oily sugar derivative, natural oils, such as vegetable oils, and mixtures thereof.
- the level of water insoluble oil in a dilute fragrance delivery vehicle of the invention is 0.1%(wt) - 7.0% (wt), preferably 0.3%(wt) - 6.0%( t), such as for example, 0.5%(wt) - 5.0%(wt).
- the level of water insoluble oil is l%(wt) - 25%(wt), preferably 3%(wt)-20%(wt). It is preferred that the water insoluble oil used in the present invention be in liquid form.
- the terms "sugar ester oil,” “sucrose poly ester” (SPE), and “oily sugar derivative” are used interchangeably and are defined in detail in WO 00/7004, which is incorporated by reference as if recited in full herein.
- the ester oils are esters containing straight or branched, saturated or unsaturated carboxylic acids.
- the ester oil or oily sugar derivative is a liquid or soft solid derivative of a cyclic polyol or of a reduced saccharide, said derivative resulting from 35 to 100% of the hydroxyl groups in said polyol or in said saccharide being esterified or etherified.
- the derivative has two or more ester or ether groups independently attached to a C 8 -C 22 alkyl or alkenyl chain.
- oily sugar derivatives of the invention are also referred to herein as "derivative-CP” and “derivative-RS” dependent upon whether the derivative is a product derived from a cyclic polyol or from a reduced saccharide starting material respectively.
- the derivative-CP and derivative-RS contain 35% by weight tri or higher esters, e.g. at least 40%.
- the tetra, penta etc. prefixes only indicate the average degrees of esterification or etherification.
- the compounds exist as a mixture of materials ranging from the monoester to the fully esterified ester. It is the average degree of esterification as determined by weight that is referred to herein.
- the derivative-CP and derivative-RS used do not have substantial crystalline character at 20°C. Instead they are preferably in a liquid or soft solid state, as hereinbelow defined, at 20°C.
- the starting cyclic polyol or reduced saccharide material is esterified or etherified with C 8 -C 22 alkyl or alkenyl chains to the appropriate extent of esterification or etherification so that the derivatives are in the requisite liquid or soft solid state.
- These chains may contain unsaturation, branching or mixed chain lengths.
- the derivative-CP or derivative-RS has 3 or more, preferably
- ester or ether groups for example 3 to 8, e.g. 3 to 5, ester or ether groups or mixtures thereof. It is preferred if two or more of the ester or ether groups of the derivative-CP and derivative-RS are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain.
- the alkyl or alkenyl groups may be branched or linear carbon chains.
- derivative-CP and derivative-RS encompass all ether or ester derivatives of all forms of saccharides, which fall into the above definition.
- preferred saccharides for the derivative-CP and derivative-RS to be derived from are monosaccharides and disaccharides.
- Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is especially preferred.
- An example of a reduced saccharide is sorbitan.
- Examples of disaccharides include maltose, lactose, cellobiose and sucrose. Sucrose is especially preferred.
- the derivative-CP is based on a disaccharide it is preferred if the disaccharide has 3 or more ester or ether groups attached to it. Examples include sucrose tri, tetra and penta esters. Where the cyclic polyol is a reducing sugar it is advantageous if each ring of the derivative-CP has one ether group, preferably at the C- . position. Suitable examples of such compounds include methyl glucose derivatives.
- Suitable derivative-CPs include esters of alkyl(poly)glucosides, in particular alkyl glucoside esters having a degree of polymerization from 1 to 2.
- the HLB of the derivative-CP and derivative-RS is typically between 1 and 3.
- the derivative-CP and derivative-RS may have branched or linear alkyl or alkenyl chains (with varying degrees of brandling), mixed chain lengths and/or unsaturation. Those having unsaturated and/or mixed alkyl chain lengths are preferred.
- One or more of the alkyl or alkenyl chains may contain at least one unsaturated bond.
- predominantly unsaturated fatty chains may be attached to the ester/ether groups, e.g. those attached may be derived from rape oil, cotton seed oil, soybean oil, oleic, tallow, palmitoleic, linoleic, erucic or other sources of unsaturated vegetable fatty acids.
- the alkyl or alkenyl chains of the derivative-CP and derivative-RS are preferably predominantly unsaturated, for example sucrose tetratallowate, sucrose tetrarapeate, sucrose tetraoleate, sucrose tetraesters of soybean oil or cotton seed oil, cellobiose tetraoleate, sucrose trioleate, sucrose triapeate, sucrose pentaoleate, sucrose pentarapeate, sucrose hexaoleate, sucrose hexarapeate, sucrose triesters, pentaesters and hexaesters of soybean oil or cotton seed oil, glucose trioleate, glucose tetraoleate, xylose trioleate, or sucrose tetra-,tri-, penta- or hexa- esters with any mixture of predominantly unsaturated fatty acid chains.
- sucrose tetratallowate sucrose tetrarapeate
- sucrose tetraoleate suc
- derivative-CPs and derivative-RS s may be based on alkyl or alkenyl chains derived from polyunsaturated fatty acid sources, e.g. sucrose tetralinoleate. It is preferred that most, if not all, of the polyunsaturation has been removed by partial hydrogenation if such polyunsaturated fatty acid chains are used.
- Oily sugar derivatives suitable for use in the compositions include sucrose pentalaurate, sucrose tetraoleate, sucrose pentaerucate, sucrose tetraerucate, and sucrose pentaoleate and the like.
- Suitable materials include some of the Ryoto series available from Mitsubishi Kagaku Foods Corporation, such as for example
- the fragrance composition of the present invention may be composed of aroma chemicals selected from one or more of the following classes: alcohols, aldehydes, ketones, esters, acetals, oximes, nitriles, ethers, and essential oils.
- another embodiment of the invention is a process for enhancing the fragrance of a consumer product.
- This process includes incorporating a fragrance improving quantity of the fragrance delivery vehicle of the invention into a consumer product.
- a "fragrance-improving quantity" of the fragrance delivery vehicle corresponds to the amount of the fragrance delivery vehicle required to condition and impart a fragrance to a substrate.
- a fragrance- improving quantity of the fragrance delivery vehicle as used herein means from about 0.5 to about 25%) wt, preferably from about 1% to about 20%(wt), such as for example from about 5% to about 10%(wt) based on the weight of the consumer product.
- a consumer product includes any commercially available product to which the present fragrance delivery vehicles may be added, without significantly altering the underlying function of the consumer product.
- a consumer product includes for example, laundry detergents, laundry and hair conditioners, soaps, shampoos, face, hair, and body creams, fabric softeners, dewrinklers, cleansers, and the like.
- X is:
- Part M 33% The product was assessed for Odor Intensity by a panel of 5 trained panelists.
- the number in the Table indicates the number of panelist selecting the product with the strongest odor:
- Example 2 The panelists then selected each composition by odor intensity as set forth in Example 2:
- Example 5 The effect of CLogP of the fragrance materials on the delivery fragrance materials from a rinse solution in cationic only and cationic plus oil systems was investigated.
- compositions were prepared in demineralized water incorporating the fragrance RCLP2 shown below at 1%.
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
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- Epidemiology (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001270305A AU2001270305A1 (en) | 2000-07-07 | 2001-07-05 | Process for imparting conditioning and good fragrance perception to both damp and dry fabric |
EP01948879A EP1299514A1 (en) | 2000-07-07 | 2001-07-05 | Process for imparting conditioning and good fragrance perception to both damp and dry fabric |
US09/932,511 US20020055452A1 (en) | 2000-07-07 | 2001-08-17 | Process for imparting a fragrance to a product and fragrance and conditioning to a dry fabric |
US10/486,623 US20040220064A1 (en) | 2000-07-07 | 2002-08-12 | Fragrance delivery vehicle |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21657100P | 2000-07-07 | 2000-07-07 | |
US60/216,571 | 2000-07-07 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/932,511 Continuation-In-Part US20020055452A1 (en) | 2000-07-07 | 2001-08-17 | Process for imparting a fragrance to a product and fragrance and conditioning to a dry fabric |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002004587A1 true WO2002004587A1 (en) | 2002-01-17 |
Family
ID=22807590
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/021334 WO2002004587A1 (en) | 2000-07-07 | 2001-07-05 | Process for imparting conditioning and good fragrance perception to both damp and dry fabric |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1299514A1 (en) |
AU (1) | AU2001270305A1 (en) |
WO (1) | WO2002004587A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003016451A1 (en) * | 2001-08-17 | 2003-02-27 | Givaudan Sa | Fragrance delivery vehicle |
WO2007025402A1 (en) * | 2005-08-30 | 2007-03-08 | Givaudan Sa | Compositions and methods to counteract oral malodour |
WO2009146981A1 (en) | 2008-06-05 | 2009-12-10 | Unilever Plc | Improvements relating to fabric conditioners |
US20180362896A1 (en) * | 2017-06-19 | 2018-12-20 | The Procter & Gamble Company | Perfume delivery aggregates |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3790484A (en) * | 1972-01-18 | 1974-02-05 | Blalock E | Fragrance-imparting laundering composition |
EP0469228A1 (en) * | 1990-07-31 | 1992-02-05 | The Procter & Gamble Company | Improved perfume carriage and delivery system for laundry applications |
WO1995022594A1 (en) * | 1994-02-21 | 1995-08-24 | Unilever Plc | Fabric softening composition |
US5652206A (en) * | 1996-02-26 | 1997-07-29 | The Procter & Gamble Company | Fabric softener compositions with improved environmental impact |
EP0829531A1 (en) * | 1996-08-22 | 1998-03-18 | Unilever Plc | Fabric conditioning composition |
WO1999021532A1 (en) * | 1997-10-24 | 1999-05-06 | The Procter & Gamble Company | Cleansing and conditioning article for skin or hair having improved fragrance delivery |
WO1999043777A1 (en) * | 1998-02-27 | 1999-09-02 | Unilever Plc | Fabric conditioning concentrate |
-
2001
- 2001-07-05 AU AU2001270305A patent/AU2001270305A1/en not_active Abandoned
- 2001-07-05 WO PCT/US2001/021334 patent/WO2002004587A1/en not_active Application Discontinuation
- 2001-07-05 EP EP01948879A patent/EP1299514A1/en not_active Withdrawn
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3790484A (en) * | 1972-01-18 | 1974-02-05 | Blalock E | Fragrance-imparting laundering composition |
EP0469228A1 (en) * | 1990-07-31 | 1992-02-05 | The Procter & Gamble Company | Improved perfume carriage and delivery system for laundry applications |
WO1995022594A1 (en) * | 1994-02-21 | 1995-08-24 | Unilever Plc | Fabric softening composition |
US5652206A (en) * | 1996-02-26 | 1997-07-29 | The Procter & Gamble Company | Fabric softener compositions with improved environmental impact |
EP0829531A1 (en) * | 1996-08-22 | 1998-03-18 | Unilever Plc | Fabric conditioning composition |
WO1999021532A1 (en) * | 1997-10-24 | 1999-05-06 | The Procter & Gamble Company | Cleansing and conditioning article for skin or hair having improved fragrance delivery |
WO1999043777A1 (en) * | 1998-02-27 | 1999-09-02 | Unilever Plc | Fabric conditioning concentrate |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003016451A1 (en) * | 2001-08-17 | 2003-02-27 | Givaudan Sa | Fragrance delivery vehicle |
WO2007025402A1 (en) * | 2005-08-30 | 2007-03-08 | Givaudan Sa | Compositions and methods to counteract oral malodour |
WO2009146981A1 (en) | 2008-06-05 | 2009-12-10 | Unilever Plc | Improvements relating to fabric conditioners |
US20180362896A1 (en) * | 2017-06-19 | 2018-12-20 | The Procter & Gamble Company | Perfume delivery aggregates |
EP3418367A1 (en) * | 2017-06-19 | 2018-12-26 | The Procter & Gamble Company | Perfume delivery aggregates |
WO2018236622A1 (en) * | 2017-06-19 | 2018-12-27 | The Procter & Gamble Company | Perfume delivery aggregates |
Also Published As
Publication number | Publication date |
---|---|
EP1299514A1 (en) | 2003-04-09 |
AU2001270305A1 (en) | 2002-01-21 |
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