US20060172917A1 - Fragrance delivery - Google Patents

Fragrance delivery Download PDF

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Publication number
US20060172917A1
US20060172917A1 US10/549,509 US54950905A US2006172917A1 US 20060172917 A1 US20060172917 A1 US 20060172917A1 US 54950905 A US54950905 A US 54950905A US 2006172917 A1 US2006172917 A1 US 2006172917A1
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Prior art keywords
water
fragrance
soluble salt
weight ratio
particulate carrier
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US10/549,509
Inventor
Kumar Vedantam
Tan Yong
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Givaudan SA
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Givaudan SA
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Assigned to GIVAUDAN SA reassignment GIVAUDAN SA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VEDANTAM, VENKATESWARA KUMAR, TAN, TEE YONG
Publication of US20060172917A1 publication Critical patent/US20060172917A1/en
Priority to US12/879,340 priority Critical patent/US8871697B2/en
Abandoned legal-status Critical Current

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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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • 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
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Definitions

  • This invention relates to a means of fragrance delivery in washing products.
  • fragrances such as perfumes to substrates by means of their incorporation into washing products such as laundry detergents.
  • washing products contain surfactants, which form micelles in water, and, as many fragrances are hydrophobic, they tend to migrate to the micelles, rather than deposit on the substrate.
  • the invention therefore provides a method of preparation of a free-flowing solid fragrance-providing composition, consisting essentially of the addition of a fragrance to a particulate carrier material in the presence of a water-soluble salt of an alkali or alkaline earth metal.
  • the invention additionally provides a free-flowing solid fragrance-providing composition, consisting essentially of a particulate carrier on which is deposited a fragrance and a water-soluble salt of an alkali or alkaline earth metal, the composition comprising at least 60% by weight of water-soluble salt and 20% maximum by weight of particulate carrier, and the ratio of water-soluble salt to fragrance being from 20:1 to 1.5:1.
  • compositions of the present invention differ considerably from known compositions, which have high proportions of particulate carrier (usually in excess of 40% by weight) and high perfume loadings (typically from 20-50% by weight of the total composition).
  • the fragrances for use in this invention may be selected from any suitable fragrance known to the art. It is a characteristic of this invention that an unusually broad range of fragrances may be used. Examples include digeranyl succinate, dineryl succinate, geranyl neryl succinate, geranyl phenylacetate, neryl phenylacetate, geranyl laurate, neryl laurate, di(b-citronellyl) maleate, dinonadol maleate, diphenoxyanol maleate, di(3,7-dimethyl-1-octanyl) succinate, di(cyclohexylethyl) maleate, diflralyl succinate, di(phenylethyl) adipate, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl naphthalene, ionone methyl, ionone gamma methyl, methyl cedryl
  • fragrances are generally available in liquid form (as solutions in organic solvent) and this is the form in which they are used in this invention.
  • the carrier material may be any suitable particulate carrier known to the art to be suitable as a carrier material for fragrances.
  • Preferred are fine, porous silicas.
  • Typical silicas are precipitated silicas, or they may be fumed silicas.
  • the silicas should have a particle size 2-15 ⁇ M and a BET surface area of from 140 to 550 M 2 /g.
  • the silicas are capable of adsorbing from 2-3 times their weight in fragrance.
  • Suitable silicas of the correct particle size may be provided in that size, or they may be produced from larger particle size silicas by known techniques, such as milling.
  • Typical commercial products include SIPERNAT (trade mark) 22S, 22LS and 50S (ex Degussa). It is possible to use silica particles of other sizes and hydrophilicity, but these are less preferred.
  • Part of the silica can be replaced by other absorbent particulate materials, such as bentonites and cellulose derivatives (for example carboxymethyl cellulose). Up to 50% by weight can be replaced but preferably the replacement is no higher than 40%, preferably no higher than 30%.
  • the water-soluble salts of alkali or alkaline earth metals may be any such salts known to the art. Typical examples include sodium and potassium chlorides and sodium sulphate, sodium chloride being especially preferred. Preferably, they should make up at least 60% by weight of the total composition.
  • the weight ratio of particulate carrier to water-soluble salt is from 1:2 1 to 1:20, more preferably from 1:5 to 1:20, even more preferably from 1:10 to 1:20 and most preferably from 1:8 to 1:15.
  • the ratio of water-soluble salt to perfume is preferably from 20:1 to 1.5:1, more preferably from 8:1 to 5:1 or from 10:1 to 20:1
  • a typical composition according to this invention will have 80% salt, 10% silica and 10% fragrance. This is in marked contrast to the 50-70% silica and 30-50% fragrance in typical known formulations.
  • the fragrance-providing compositions according to the invention may additionally contain other known ingredients added in art-recognised quantities to perform their known functions.
  • One such particularly useful ingredient is clay, added to give a softening effect.
  • Particularly preferred clays are bentonites.
  • examples of other art-recognised ingredients that can be included are antibacterial agents, fluorescing and whitening agents and malodour counteracting agents.
  • fragrance-providing compositions according to the invention are prepared by thoroughly mixing the dry ingredients (particulate carrier, salt, other ingredients) and then adding the liquid fragrance composition and stirring until a free-flowing dry powder is achieved. Given that the final product is a free-flowing powder, a wide variety of proportions of ingredients may be used, depending upon the individual natures of the ingredients, and the skilled person can easily determine appropriate amounts by simple experimentation in every case.
  • the fragrance-providing compositions of the invention are easily made and storage stable. The process for their manufacture is simple and does not suffer from the high rate of fragrance loss that plagues other encapsulation techniques. In a wash or rinse liquor, the water-soluble salt dissolves readily, unlike many known compositions, and the released fragrance partitions preferably on to the substrate being washed.
  • the invention therefore provides a method of applying a fragrance as hereinabove described to a substrate during washing or rinsing, comprising the adding to the wash or rinse water of a fragrance-providing composition
  • Admixtures A-H of the compositions shown in Table 1 below are prepared by blending fumed silica, CMC and sodium chloride and then adding perfume, and mixing until a free-flowing powder is achieved. 0.5 g of each is added to one litre of water to give a liquor. A towel is soaked in the liquor for ten minutes and squeezed and dried in open air.
  • Olfactive evaluations are carried at regular intervals of time by an expert panel of evaluators.
  • Example 1 is repeated with compositions J-O as shown in the table below.

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  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Confectionery (AREA)
  • Semiconductor Lasers (AREA)
  • Reciprocating, Oscillating Or Vibrating Motors (AREA)

Abstract

A substrate such as a fabric may be provided with a fragrance during washing or rinsing process by the addition to the wash water of a free-flowing solid fragrance-providing composition that comprises a fragrance deposited on a particulate carrier along with a water soluble salt of an alkali metal or an alkaline earth metal.

Description

  • This invention relates to a means of fragrance delivery in washing products.
  • It is desirable to deliver fragrances such as perfumes to substrates by means of their incorporation into washing products such as laundry detergents. However, many washing products contain surfactants, which form micelles in water, and, as many fragrances are hydrophobic, they tend to migrate to the micelles, rather than deposit on the substrate.
  • Several methods of overcoming this problem have been tried. One is to use fragrances that are not attracted more to the micelles than to the substrate. This is possible, but it restricts greatly the range of possible fragrances that can be used.
  • Various methods have relied on using solid carriers for fragrances. Typical examples of such carriers include inorganic particles, usually silica (both precipitated and gel-type). However, the major drawback of these methods has been the water insolubility of the carrier.
  • It has now been found that an inexpensive, convenient method overcomes all these disadvantages and permits the achievement of a fragrance that is delivered to the substrate. The invention therefore provides a method of preparation of a free-flowing solid fragrance-providing composition, consisting essentially of the addition of a fragrance to a particulate carrier material in the presence of a water-soluble salt of an alkali or alkaline earth metal.
  • The invention additionally provides a free-flowing solid fragrance-providing composition, consisting essentially of a particulate carrier on which is deposited a fragrance and a water-soluble salt of an alkali or alkaline earth metal, the composition comprising at least 60% by weight of water-soluble salt and 20% maximum by weight of particulate carrier, and the ratio of water-soluble salt to fragrance being from 20:1 to 1.5:1.
  • The compositions of the present invention differ considerably from known compositions, which have high proportions of particulate carrier (usually in excess of 40% by weight) and high perfume loadings (typically from 20-50% by weight of the total composition).
  • In this description, unless otherwise stated, the use of the singular also includes the plural. For example, “a fragrance” also comprehends the case where more than one fragrance is used.
  • The fragrances for use in this invention may be selected from any suitable fragrance known to the art. It is a characteristic of this invention that an unusually broad range of fragrances may be used. Examples include digeranyl succinate, dineryl succinate, geranyl neryl succinate, geranyl phenylacetate, neryl phenylacetate, geranyl laurate, neryl laurate, di(b-citronellyl) maleate, dinonadol maleate, diphenoxyanol maleate, di(3,7-dimethyl-1-octanyl) succinate, di(cyclohexylethyl) maleate, diflralyl succinate, di(phenylethyl) adipate, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl naphthalene, ionone methyl, ionone gamma methyl, methyl cedrylone, methyl dihydrojasmonate, methyl 1,6,10-trimethyl-2,5,9-cyclododecatrien-1-yl ketone, 7-acetyl-1,1,3,4,4,6-hexamethyl tetralin, 4-acetyl-6-tert-butyl-1,1-dimethyl indane, para-hydroxy-phenyl-butanone, benzophenone, methyl beta-naphthyl ketone, 6-acetyl-1,1,2,3,3,5 hexamethyl indane, 5-acetyl-3-isopropyl-1,1,2,6-tetramethyl indane, 1-dodecanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 7-hydroxy-3,7-dimethyl ocatanal, 10-undecen-1-al, isohexenyl cyclohexyl carboxaldehyde, formyl tricyclodecane, condensation products of hydroxycitronellal and methyl anthranilate, condensation products of hydroxycitronellal and indol, condensation products of phenyl acetaldehyde and indol, 2-methyl-3-(para-tert-butylphenyl)-propionaldehyde, ethyl vanillin, heliotropin, hexyl cinnamic aldehyde, amyl cinnamic aldehyde, 2-methyl-2-(para-iso-propylphenyl)propionaldehyde, coumarin, decalactone gamma, cyclopentadecanolide, 16-hydroxy-9-hexadecenoic acid lactone, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclo-penta-gamma-2-benzopyrane, beta-naphthol methyl ether, ambroxane, dodecahydro-3a,6,6,9a-tetramethyinaphtho[2,1b]furan, cedrol, 5-(2,2,3-trimethylcyclopent-3-enyl)-3-methylpentan-2-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, caryophyllene alcohol, tricyclodecenyl propionate, tricyclodecenyl acetate, benzyl salicylate, cedryl acetate, para-(tert-butyl) cyclohexyl acetate, essential oils, resinoids, and resins from a variety of sources including but not limited to orange oil, lemon oil, patchouli, Peru balsam, Olibanum resinoid, styrax, labdanum resin, nutmeg, cassia oil, benzoin resin, coriander, lavandin, and lavender, phenyl ethyl alcohol, terpineol, linalool, linalyl acetate, geraniol, nerol, 2-(1,1-dimethylethyl)cyclohexanol acetate, benzyl acetate, orange terpenes, eugenol, diethylphthalate, and combinations thereof.
  • These fragrances are generally available in liquid form (as solutions in organic solvent) and this is the form in which they are used in this invention.
  • The carrier material may be any suitable particulate carrier known to the art to be suitable as a carrier material for fragrances. Preferred are fine, porous silicas. Typical silicas are precipitated silicas, or they may be fumed silicas. The silicas should have a particle size 2-15 μM and a BET surface area of from 140 to 550 M2/g. Preferably the silicas are capable of adsorbing from 2-3 times their weight in fragrance. Suitable silicas of the correct particle size may be provided in that size, or they may be produced from larger particle size silicas by known techniques, such as milling. Typical commercial products include SIPERNAT (trade mark) 22S, 22LS and 50S (ex Degussa). It is possible to use silica particles of other sizes and hydrophilicity, but these are less preferred.
  • Part of the silica can be replaced by other absorbent particulate materials, such as bentonites and cellulose derivatives (for example carboxymethyl cellulose). Up to 50% by weight can be replaced but preferably the replacement is no higher than 40%, preferably no higher than 30%.
  • The water-soluble salts of alkali or alkaline earth metals may be any such salts known to the art. Typical examples include sodium and potassium chlorides and sodium sulphate, sodium chloride being especially preferred. Preferably, they should make up at least 60% by weight of the total composition.
  • Preferably the weight ratio of particulate carrier to water-soluble salt is from 1:2 1 to 1:20, more preferably from 1:5 to 1:20, even more preferably from 1:10 to 1:20 and most preferably from 1:8 to 1:15. In addition, the ratio of water-soluble salt to perfume is preferably from 20:1 to 1.5:1, more preferably from 8:1 to 5:1 or from 10:1 to 20:1
  • A typical composition according to this invention will have 80% salt, 10% silica and 10% fragrance. This is in marked contrast to the 50-70% silica and 30-50% fragrance in typical known formulations.
  • In addition to the essential components mentioned hereinabove, the fragrance-providing compositions according to the invention may additionally contain other known ingredients added in art-recognised quantities to perform their known functions. One such particularly useful ingredient is clay, added to give a softening effect. Particularly preferred clays are bentonites. Examples of other art-recognised ingredients that can be included are antibacterial agents, fluorescing and whitening agents and malodour counteracting agents.
  • The fragrance-providing compositions according to the invention are prepared by thoroughly mixing the dry ingredients (particulate carrier, salt, other ingredients) and then adding the liquid fragrance composition and stirring until a free-flowing dry powder is achieved. Given that the final product is a free-flowing powder, a wide variety of proportions of ingredients may be used, depending upon the individual natures of the ingredients, and the skilled person can easily determine appropriate amounts by simple experimentation in every case.
  • The fragrance-providing compositions of the invention are easily made and storage stable. The process for their manufacture is simple and does not suffer from the high rate of fragrance loss that plagues other encapsulation techniques. In a wash or rinse liquor, the water-soluble salt dissolves readily, unlike many known compositions, and the released fragrance partitions preferably on to the substrate being washed. The invention therefore provides a method of applying a fragrance as hereinabove described to a substrate during washing or rinsing, comprising the adding to the wash or rinse water of a fragrance-providing composition
  • The invention is further described with reference to the following non-limiting examples.
    • EXAMPLE 1
  • Admixtures A-H of the compositions shown in Table 1 below are prepared by blending fumed silica, CMC and sodium chloride and then adding perfume, and mixing until a free-flowing powder is achieved. 0.5 g of each is added to one litre of water to give a liquor. A towel is soaked in the liquor for ten minutes and squeezed and dried in open air.
    TABLE 1
    A B C D E F G H
    Sunshine (perfume) 10 20 10 15 10 20 10 15
    AEROSIL ® 200 5 10 5 5
    AEROSIL ® R972 5 10 5 5
    Sodium Chloride 85 70 85 75 80 70 80 75
    BLANOSE ® Refined CMC 5 5 5 5
    Total 100 100 100 100 100 100 100 100

    AEROSIL is a fumed silica (trade mark of Degussa).

    “Blanose” is carboxymethyl cellulose (trade mark of Hercules)
  • Olfactive evaluations are carried at regular intervals of time by an expert panel of evaluators.
  • Performance Rating:
    5
    Figure US20060172917A1-20060803-P00801
    ---------------4--------3---------2----------→1
    Very strong Strong    Fair     Weak      Very Weak
    • Olfactive Evaluation Scores
  • Day 1 Day 3 Day 5 Day 7
    A 5.0 4.6 4.0 3.1
    B 4.8 4.6 4.1 3.0
    C 4.6 4.1 3.6 3.0
    D 4.6 4.2 3.5 2.9
    E 4.8 4.3 3.2 2.8
    F 5.0 4.6 4.3 3.6
    G 4.6 3.9 3.2 2.7
    H 4.8 4.1 3.5 3.1
    • EXAMPLE 2
  • Example 1 is repeated with compositions J-O as shown in the table below.
    J K L M N O
    WaterFall (perfume) 20 30 10 15 10 5
    AEROSIL ® 200 5 10 5 5 4 5
    LAUNDROSIL ® DGA 5 10 5 15 6 5
    Sodium Sulphate 70 50 80 65 80 85
    Total 100 100 100 100 100

    LAUNDROSIL is a detergent-grade bentonite (trade mark of Süd-Chemie AG)
  • The results are as follows:
    • Olfactive Evaluation Scores
  • Day 1 Day 2 Day 5 Day 7
    J 5 4.6 4.4 3.8
    K 5 4.4 4.0 3.8
    L 4.6 4.0 3.4 2.9
    M 4.5 3.9 3.6 3.2
    N 4.7 4.0 3.4 3.0
    O 4.7 3.8 3.0 2.6

Claims (20)

1. A method of preparation of a free-flowing solid fragrance-providing composition, comprising the addition of a fragrance to a particulate carrier material in the presence of a water-soluble salt of an alkali or alkaline earth metal.
2. A method according to claim 1, in which the weight ratio of particulate carrier to water-soluble salt is from 1:1 to 1:20.
3. A method according to claim 1, in which the weight ratio of water-soluble salt to fragrance is from 20:1 to 1.5:1.
4. A method according to claim 1 in which the particulate carrier is fine, porous silica, optionally replaced to a maximum of 50% by weight of other absorbent particulate materials.
5. A free-flowing solid fragrance-providing composition, consisting essentially of a particulate carrier on which is deposited a fragrance and a water-soluble salt of an alkali or alkaline earth metal, the composition comprising at least 60% by weight of water-soluble salt and 20% maximum by weight of particulate carrier, and the ratio of water-soluble salt to fragrance being from 20:1 to 1.5:1.
6. A composition according to claim 1, in which the weight ratio of particulate carrier to water-soluble salt is from 1:2 to 1:20, and the weight ratio of water-soluble salt to fragrance is from 8:1 to 5:1.
7. A composition according to claim 6, in which the weight ratio of particulate carrier to water-soluble salt is from 1:2 to 1:20, and the weight ratio of water-soluble salt to fragrance is from 10:1 to 20:1.
8. A method of providing a fragrance to a substrate during washing or rinsing, comprising the adding to the wash or rinse water of a free-flowing solid fragrance-providing composition according to claim 5.
9. A method according to claim 2, in which the weight ratio of particulate carrier to water-soluble salt is from 1:5 to 1:20.
10. A method according to claim 9, in which the weight ratio of particulate carrier to water-soluble salt is from 1:10 to 1:20.
11. A method according to claim 2, in which the weight ratio of particulate carrier to water-soluble salt is from 1:8 to 1:15.
12. A method according to claim 3, in which the weight ratio of water-soluble salt to fragrance is from 8:1 to 5:1.
13. A method according to claim 12 in which the weight ratio of water-soluble salt to fragrance is from 10:1 to 20:1.
14. A composition according to claim 6, in which the weight ratio of particulate carrier to water-soluble salt is from 1:5 to 1:20, and the weight ratio of water-soluble salt to fragrance is from 8:1 to 5:1.
15. A composition according to claim 14, in which the weight ratio of particulate carrier to water-soluble salt is from 1:10 to 1:20, and the weight ratio of water-soluble salt to fragrance is from 8:1 to 5:1.
16. A composition according to claim 15, in which the weight ratio of particulate carrier to water-soluble salt is from 1:8 to 1:15, and the weight ratio of water-soluble salt to fragrance is from 8:1 to 5:1.
17. A composition according to claim 6, in which the weight ratio of particulate carrier to water-soluble salt is from 1:2 to 1:20, and the weight ratio of water-soluble salt to fragrance is from 10:1 to 20:1.
18. A composition according to claim 7, in which the weight ratio of particulate carrier to water-soluble salt is from 1:5 to 1:20 and the weight ratio of water-soluble salt to fragrance is from 10:1 to 20:1.
19. A composition according to claim 18, in which the weight ratio of particulate carrier to water-soluble salt is from 1:10 to 1:20 and the weight ratio of water-soluble salt to fragrance is from 10:1 to 20:1.
20. A method of providing a fragrance to a substrate during washing or rinsing, comprising the adding to the wash or rinse water of a free-flowing solid fragrance-providing composition according to claim 6.
US10/549,509 2003-03-19 2004-02-26 Fragrance delivery Abandoned US20060172917A1 (en)

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US20080253974A1 (en) * 2005-10-25 2008-10-16 Givaudan S.A. N-Phenyl-N-Pyridinyl-Benzamides and Benzenesulfonamides Having Cooling Properties
US20080277812A1 (en) * 2007-05-08 2008-11-13 Givaudan Sa Wax Encapsulation
US20080300314A1 (en) * 2003-11-21 2008-12-04 Givaudan Sa Cooling Compounds
US20090035364A1 (en) * 2006-03-15 2009-02-05 Galopin Christophe C Para-substituted 2-alkoxyphenol compounds
US20090053388A1 (en) * 2007-08-24 2009-02-26 Thomas Powers Flavor emitting compositions, devices and packaged food products therewith
US20090098066A1 (en) * 2005-08-22 2009-04-16 Galopin Christophe C Substituted bicyclo [2.2.2] oct/5-ene compounds and their use as cooling agents
US20090326144A1 (en) * 2008-06-30 2009-12-31 Kumho Tire Co., Inc. Method for preparing fragrant powder composition for tire
US20100035938A1 (en) * 2005-08-15 2010-02-11 Karen Ann Bell Cooling Compounds
US20100069681A1 (en) * 2006-11-27 2010-03-18 Basf Se Process for preparing 3-alkoxypropan-1-ols
US20100297038A1 (en) * 2008-01-17 2010-11-25 Givaudan S.A. Benzimidazole Derivatives And Their Use As Cooling Agents
US20110003731A1 (en) * 2003-03-19 2011-01-06 Givaudan Sa Fragrance Delivery
US7880011B2 (en) 2007-07-23 2011-02-01 Givandan, S.A. Amide addition reaction
US7959958B2 (en) 2007-06-13 2011-06-14 Givaudan, S.A. Cooling compounds
US8664261B2 (en) 2009-05-05 2014-03-04 Givaudan S.A. Organic compounds having cooling properties
US20170226690A1 (en) * 2016-02-09 2017-08-10 International Flavors & Fragrances Inc. Scent booster compositions

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US8871697B2 (en) 2014-10-28
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US20110003731A1 (en) 2011-01-06
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CO5660301A2 (en) 2006-07-31
GB0306152D0 (en) 2003-04-23

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