WO2020201258A1 - Fragranced composition - Google Patents
Fragranced composition Download PDFInfo
- Publication number
- WO2020201258A1 WO2020201258A1 PCT/EP2020/059064 EP2020059064W WO2020201258A1 WO 2020201258 A1 WO2020201258 A1 WO 2020201258A1 EP 2020059064 W EP2020059064 W EP 2020059064W WO 2020201258 A1 WO2020201258 A1 WO 2020201258A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fragrance
- starch
- washing composition
- fragranced
- composition according
- 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.)
- Ceased
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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
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
-
- 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
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
Definitions
- This disclosure relates to the provision of fragrance in washing compositions, such as laundry detergents.
- compositions are fragranced. Fragrances are not individual substances, but blends of perfume ingredients, sometimes 50 or more of them. They are formulated by trained, experienced perfumers to obtain a desired olfactory note.
- the problem is that washing compositions are alkaline (in water, they generate high pFIs of up to 1 1 ).
- Long storage of a fragranced dry washing composition can have a detrimental effect on some perfume ingredients. This is particularly true of esters, favoured perfume ingredients noted for their fruity/sweet notes.
- the degradation of these ingredients on storage means that, when the composition is used, the desired olfactory effect of the fragrance has been substantially lost.
- fragrances for use in such compositions are formulated with reduced proportions of such ingredients, and even in their complete absence. As these are popular ingredients, the palette of the perfumer is greatly restricted, and therefore so is the possible fragrancing of washing compositions.
- fragrances it is possible to encapsulate fragrances to preserve them in such environments, which is fine if fragrance release is desired to be released by rubbing the washed item, but not so fine if release is desired in the wash.
- a fragranced washing composition comprising a washing composition base and a fragrance, in which the fragrance is present as two separate components, a first component being a liquid component and the second component a particulate starch carrier containing the remainder of the fragrance, the liquid component comprising those fragrance ingredients that are unaffected by the composition of the base and the particulate carrier comprising those fragrance ingredients that are affected by the composition of the base.
- a washing composition typically comprises strongly alkaline materials such as sulphates, aluminosilicates and carbonates, plus powerful surfactants.
- Certain commonly-used perfume materials such as aldehydes, acetates, esters, lactones and epoxides are among the most affected and degraded by the harsh environment of a laundry detergent, and the effect of this environment can fundamentally change the hedonic effect desired by the perfumer.
- the separation of these ingredients from the rest of the perfume formula and their encapsulation allows the full fragrance as formulated to be realised in a wash.
- fragrance ingredients of the fragrance that are aldehydes, acetates, esters, lactones and epoxides are encapsulated in starch prior to their addition to the washing composition.
- aldehydes useful in this disclosure are as follows (the numbers in brackets are the relevant CAS Registry Numbers):
- AdoxalTM (141 -13-9); aldehyde c 1 10 undecylic (1 12-44-7); aldehyde c10 decylic (1 12-31 -2);
- aldehyde d 1 moa (19009-56-4); aldehyde d 1 undecylenic (1 12-45-8); aldehyde c12 mna pur (1 10-41 -8); aldehyde c6 hexylic (66-25-1 ); aldehyde cl hepatic (1 1 1 -71 -7); aldehyde c8 octylic (124-13-0); aldehyde c9 isononylic (5435-64-3); aldehyde c9 nonylic (124-19-6); aldehyde iso c 1 1 (143-14-6); aldehyde c12 lauric (1 12-54-9); alpha amyl cinnamic aldehyde (122-40-7); alpha hexyl cinnamic aldehyde (101 -86-0); alpha methyl cinnamic aldehyde (101 -39-3); benzaldehyde
- geraldehyde (85417-87-4); GeranialTM (141 -27-5); hydratropic aldehyde (93-53-8); hydratropic dimethyl acetal aldehyde (90-87-9); hydroxycitronellal (107-75-5); isobutyric aldehyde (78-84-2); isocyclocitral (1335-66-6); isovalerianic aldehyde (590-86-3); jasmacyclene (5413-60-5); LilialTM (80-54-6); MacealTM (67845-30-1 ); mefranal (55066-49-4); melonal (1 06-72-9); methional (3268-49-
- nonadienal (557-48-2); nonenal-6-cis (2277-19-2); phenyl acetic aldehyde (122-78-1 ); phenyl propionic aldehyde (104-53-0); safranal (1 1 6-26-7); scentenal (86803-90-9); tetrahydro citral (5988- 91 -0); tricyclal (68039-49-6); tridecenal-2-trans (7774-82-5); trifernal (16251 -77-7); TropionalTM (1205-17-0); vernaldehyde (66327-54-6)
- Aldehydes may be present to the extent of up to 30% by weight of the total perfume in the composition.
- Typical and non-limiting acetates and esters useful in this disclosure are as follows:
- AgrumexTM (88-41 -5); allyl caproate (123-68-2); allyl cyclohexyl propionate (2705-87-5); allyl heptanoate (142-19-8); allyl phenoxy acetate (7493-74-5); amyl butyrate (540-18-1 ); amyl phenyl acetate (5137-52-0); amyl salicylate (2050-08-0); anapear (189440-77-5); benzyl acetate (140-1 1 -
- ethoxalate citronellyle (60788-25-2); ethyl 2-decenoate (7367-88-6); ethyl 2-methyl butyrate (7452- 79-1 ); ethyl acetate (141 -78-6); ethyl acetoacetate (141 -97-9); ethyl benzoate (93-89-0); ethyl butyrate (1 05-54-4); ethyl capronate (123-66-0); ethyl caprylate (106-32-1 ); ethyl cinnamate (103- 36-6); ethyl cyclohexyl acetate (5452-75-5); ethyl decadienoate (3025-30-7); ethyl isobutyrate (97- 62-1 ); ethyl isovalerate (1 08-64-5); ethyl linalyl acetate (61931 -80-4); ethyl methyl-2
- hexyl salicylate (6259-76-3); isoamyl acetate (123-92-2); isoamyl butyrate (106-27-4); isoamyl propionate (105-68-0); isobutyl acetate (1 10-19-0); isobutyl benzoate (120-50-3); isobutyl isobutyrate (97-85-8); isobutyl phenyl acetate (102-13-6); isobutyl salicylate (87-19-4); isononyl acetate pure (40379-24-6); isopentyl isovalerate (659-70-1 ); isopropyl 2-methylbutyrate (66576-71 -
- Acetates may be present to the extent of up to 50% by weight of the total perfume in the composition.
- Esters may be present to the extent of up to 90% by weight of the total perfume in the composition.
- Typical and non-limiting lactones useful in this disclosure are as follows:
- epoxide fragrance ingredients include ethyl phenyl glycidate (121 -39-1 ) and ethyl methyl phenyl glycidate (77-83-8). These two are most commonly
- Starch encapsulation of fragrance is a well-known technology that has been used in industry for many years. It involves the emulsification of fragrance and a modified hydrophobic starch in water, and this emulsion is then spray-dried to give fragrance-containing particles.
- Spray drying is a well-established industrial technique, used to produce powder granules for the food, pharmaceutical and chemical industries. This process is preferred for encapsulation over other techniques as it is faster, more economical and efficient.
- a mixture of the material to be encapsulated and a solution of encapsulant material in a solvent is sprayed into a heated chamber in the form of atomized droplets.
- the liquid part of the droplets evaporates rapidly, producing powder granules.
- the morphology of the spray-dried granules can be controlled by controlling various spray drying parameters.
- the choice of encapsulant material is crucial and depends on the particular application. Usually an amphipathic carrier material is chosen as encapsulating material.
- the hydrophobic part of the amphipathic carrier attaches itself to the surface of the material to be encapsulated. Subsequent drying increases the concentration of the encapsulant material on the surface of the core material and forms a solid particle.
- the starch must have no reactivity with the fragrance, be present in a form that is easy to handle, i.e. with low viscosity at high concentration to allow a complete elimination of solvent in any processes requiring a phase of desolvatation, give the maximum protection of the fragrance against external factors, ensure good emulsion stabilization properties and effective redispersion behaviour in order to release the fragrance at the times and the place desired.
- Starches suitable for encapsulating fragrances can be made from, raw starch, pregelatinized starch, modified starch derived from tubers, legumes, cereal and grains, for example corn starch, wheat starch, rice starch, waxy corn starch, oat starch, cassava starch, waxy barley, waxy rice starch, sweet rice starch, amioca, potato starch, tapioca starch, oat starch, cassava starch, and mixtures thereof.
- Modified starches suitable for use as the encapsulating matrix include hydrolyzed starch, acid- thinned starch, starch esters of long chain hydrocarbons, starch acetates, starch octenyl succinates, and mixtures thereof.
- hydrolyzed starch refers to oligosaccharide-type materials that are typically obtained by acid and/or enzymatic hydrolysis of starches, preferably corn starch. Suitable hydrolyzed starches for inclusion in the present invention include maltodextrins and corn syrup solids.
- Starch esters having a degree of substitution in the range of from about 0.01 % to about 10.0% may be used to encapsulate the perfume oils of the present invention.
- the hydrocarbon part of the modifying ester is from a C5 to C16 carbon chain.
- octenylsuccinate (OSAN) substituted waxy corn starches of various types such as 1 ) waxy starch: acid thinned and OSAN substituted, 2) blend of corn syrup solids: waxy starch, OSAN substituted, and dextrinized, 3) waxy starch: OSAN substituted and dextrinized, 4) blend of corn syrup solids or maltodextrins with waxy starch: acid-thinned OSAN substituted, and then cooked and spray dried, 5) waxy starch: acid thinned and OSAN substituted then cooked and spray dried, and 6) the high and low viscosities of the above modifications (based on the level of acid treatment) may be used.
- Modified starches having emulsifying and emulsion stabilizing capacity such as starch octenyl succinates have the ability to entrap the fragrance droplets in the emulsion due to the hydrophobic character of the starch modifying agent.
- the perfume oils remain trapped in the modified starch until dissolve in the wash solution, due to thermodynamic factors i. e., hydrophobic interactions and stabilization of the emulsion because of steric hindrance.
- the starch used is starch sodium octenyl succinate.
- a formulation for the encapsulation of that part of the fragrance to be encapsulated is 45-55% (wt) perfume
- a humectant may be added to prevent the starch from drying out.
- Typical examples include sugar alcohols such as mannitol, sorbitol, xylitol, erythritol and isomalt. This also helps to achieve a uniform dispersion.
- Such a material may be present at a weight proportion of from 4-8% by weight.
- Another possible ingredient is a bulking agent.
- a typical example is a finely-divided silica, such as a fumed silica, a typical material being AerosilTM 200. This is present in a weight proportion of from 0.05-3%.
- the fragrance formulation for use in the washing composition is divided in two parts, one part comprising the ingredients to be incorporated into the particulate starch carrier, and the other added to the washing composition base, the proportions of the two parts of the fragrance being such that a combination of the two would provide the complete fragrance as formulated.
- the particulate carrier is prepared by first blending the fragrance ingredients to be encapsulated and then emulsifying them in water with the starch. The emulsion is then spray-dried by spraying into a heated chamber and collecting the resulting particles.
- the normal techniques and conditions of spray drying of fragrance particles are well known and may be used here.
- the washing composition base which may be a solid or liquid composition, consists of all the usual ingredients of a dry washing composition other than fragrance. These include detergents, surfactants, abrasives, alkalis, enzymes, colouring matters and dyestuffs, optical brighteners, preservatives, anti-bacterial and anti-fungal materials, surface tension modifiers, and the like. They may be used in art-recognised proportions. That part of the fragrance, which is added to the washing composition base, is used in such a proportion that, in combination with the fragrance in the particulate carrier, it delivers the full fragrance formulation in the wash solution.
- the fragranced washing composition is prepared by adding the starch-encapsulated component of the fragrance to the washing composition base and mixing thoroughly. The remaining non- encapsulated component of the fragrance is then added to this mixture with stirring until the result is a dry powder.
- the combined fragrances are typically present to the extent of from 0.05% and 1 .5% by weight of the complete two-component washing composition.
- Washing compositions according to this disclosure have the advantage that, in use in a wash, the full fragrance as formulated by the perfumer is delivered, without any loss of particular fragrance notes as a result of interaction with harsh washing ingredients.
- the disclosure is further described with reference to the following examples, which describe particular embodiments, and which are not intended to be in any way limiting. All parts and percentages, unless otherwise specified, are by weight.
- a fragrance formulation for use in the washing composition was formulated in two parts.
- One part comprised detergent-unstable ingredients to be incorporated into a starch encapsulate formulation (designated as“Fragile”).
- the other part to be added directly to the washing composition base comprised detergent-stable ingredients (designated as“Robust”).
- the proportions of the two parts of the fragrance were such that a combination of the two would provide the complete fragrance as formulated.
- The“fragile” components are shown in Table 1 and the“robust” in Table 2.
- the fragrance content of the starch-encapsulated part was 50% of the weight of the individual particles.
- An encapsulated perfume was prepared as follows, using the following formula.
- An emulsion was prepared as follows:
- the spray droplet size was to be between 0.5 and 2 miti (controlled by dynamic light scattering) - Inlet Temperature: 190 °C
- PD base A powder detergent base (“PD base”) was prepared as follows:
- Sample a PD base dosed with starch-encapsulated“Fragile“ component @ 0.72% by weight - as the encapsulated material contains 50% fragrance, this gives a“Fragile” perfume loading of 0.36%
- Sample b PD sample dosed with unencapsulated“Fragile” component @0.36%
- Sample c PD base dosed with starch-encapsulated“Fragile” component @ 0.72% +“Robust” component @0.04%
- Sample d PD base dosed with unencapsulated“Fragile” component @0.36% +“Robust” component @0.04%
- Sample d is equivalent to the whole fragrance (mixture of“Fragile” and“Robust”
- Sample a:To PD base (99.28% by weight of total mixture) was added starch-encapsulated“Fragile” @ 0.72% and mixed thoroughly to homogenize.
- Sample b To PD base (99.28% by weight) was added unencapsulated“Fragile” @ 0.36% and mixed thoroughly to homogenize.
- Sample c To PD base (99.24% by weight of total mixture) was added starch-encapsulated “Fragile” @ 0.72% +“Robust” @0.04% and mixed thoroughly to homogenize.
- the detergent wash test solution preparation was as follows:
- the unrinsed towel in the bowl was raised from the bowl by tongs for testing by an expert panel. Both were compared for odour strength, using a scale of from 0-5, where 0 is no fragrance detectable, 3 is good and 5 is very strong. In addition, the olfactory qualities were assessed in comparison with the complete fragrance.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX2021010967A MX2021010967A (en) | 2019-04-03 | 2020-03-31 | FRAGRANCE COMPOSITION. |
| PH1/2021/552463A PH12021552463A1 (en) | 2019-04-03 | 2020-03-31 | Fragranced composition |
| SG11202109838U SG11202109838UA (en) | 2019-04-03 | 2020-03-31 | Fragranced composition |
| BR112021018358A BR112021018358A2 (en) | 2019-04-03 | 2020-03-31 | Flavored composition |
| CN202080025435.5A CN113646417A (en) | 2019-04-03 | 2020-03-31 | Perfumed composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1904695.2 | 2019-04-03 | ||
| GBGB1904695.2A GB201904695D0 (en) | 2019-04-03 | 2019-04-03 | Fragranced composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2020201258A1 true WO2020201258A1 (en) | 2020-10-08 |
Family
ID=66443051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2020/059064 Ceased WO2020201258A1 (en) | 2019-04-03 | 2020-03-31 | Fragranced composition |
Country Status (7)
| Country | Link |
|---|---|
| CN (1) | CN113646417A (en) |
| BR (1) | BR112021018358A2 (en) |
| GB (1) | GB201904695D0 (en) |
| MX (1) | MX2021010967A (en) |
| PH (1) | PH12021552463A1 (en) |
| SG (1) | SG11202109838UA (en) |
| WO (1) | WO2020201258A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023111164A1 (en) | 2021-12-15 | 2023-06-22 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2024256539A1 (en) | 2023-06-15 | 2024-12-19 | Givaudan Sa | Improvements in or relating to organic compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115736158A (en) * | 2022-12-30 | 2023-03-07 | 广州百花香料股份有限公司 | Stable emulsified essence and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6458754B1 (en) * | 1998-04-23 | 2002-10-01 | The Procter & Gamble Company | Encapsulated perfume particles and detergent compositions containing said particles |
| WO2004113485A1 (en) * | 2003-06-18 | 2004-12-29 | The Procter & Gamble Company | Blooming soap bars |
| US20100143422A1 (en) * | 2008-12-04 | 2010-06-10 | Lewis Michael Popplewell | Microcapsules Containing Active Ingredients |
| US20130005635A1 (en) * | 2009-06-30 | 2013-01-03 | Giulia Ottavia Bianchetti | Bleaching compositions comprising a perfume delivery system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060003913A1 (en) * | 2004-06-30 | 2006-01-05 | The Procter & Gamble Company | Perfumed liquid laundry detergent compositions with functionalized silicone fabric care agents |
-
2019
- 2019-04-03 GB GBGB1904695.2A patent/GB201904695D0/en not_active Ceased
-
2020
- 2020-03-31 BR BR112021018358A patent/BR112021018358A2/en not_active Application Discontinuation
- 2020-03-31 MX MX2021010967A patent/MX2021010967A/en unknown
- 2020-03-31 CN CN202080025435.5A patent/CN113646417A/en active Pending
- 2020-03-31 PH PH1/2021/552463A patent/PH12021552463A1/en unknown
- 2020-03-31 WO PCT/EP2020/059064 patent/WO2020201258A1/en not_active Ceased
- 2020-03-31 SG SG11202109838U patent/SG11202109838UA/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6458754B1 (en) * | 1998-04-23 | 2002-10-01 | The Procter & Gamble Company | Encapsulated perfume particles and detergent compositions containing said particles |
| WO2004113485A1 (en) * | 2003-06-18 | 2004-12-29 | The Procter & Gamble Company | Blooming soap bars |
| US20100143422A1 (en) * | 2008-12-04 | 2010-06-10 | Lewis Michael Popplewell | Microcapsules Containing Active Ingredients |
| US20130005635A1 (en) * | 2009-06-30 | 2013-01-03 | Giulia Ottavia Bianchetti | Bleaching compositions comprising a perfume delivery system |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 141-13-9, 112-44-7, 112-31-2, 19009-56-4, 112-45-8, 110-41-8, 66-25-1, 111-71-7, 124-13-0, 5435-64-3, 124-19-6, 143-14-6, 112-54-9, 122-40-7, 101-86-0, 101-39-3, 100-52-7, 18127-01-0, 65405-84-7, 5392-40-5, 106-23-0, 122-03-2, 68039-49-6, 103-95-7, 31906-04-4, 25152-84-5, 3913-81-3, 65405-70-1, 39770-05-3, 51513-58-7, 4826-62-4, 41448-29-7, 5462-06-6, 125109-85-5, 93-92-5, 85417-87-4, 141-27-5, 93-53-8, 90-87-9, 107-75-5, 78-84-2, 1335-66-6, 590-86-3, 5413-60-5, 80-54-6, 67845-30-1, 55066-49-4, (106-72-9, 3268-49-3, 62439-41-2, 21834-92-4, 106-26-3, 557-48-2, 2277-19-2, 122-78-1, 104-53-0, 116-26-7, 86803-90-9, 5988-91-0, 68039-49-6, 7774-82-5, 16251-77-7, 1205-17-0, 66327-54-6, 88-41-5, 123-68-2, 2705-87-5, 142-19-8, 7493-74-5, 540-18-1, 5137-52-0, 2050-08-0, 189440-77-5, 140-11-4, 120-51-4, 103-37-7, 103-41-3, 104-57-4, 103-28-6, 103-38-8, 102-16-9, 122-63-4, 118-58-1, 76-49-3, 123-86-4, 109-21-7, 7492-70-8, 138-22-7, 112-14-1, 77- |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023111164A1 (en) | 2021-12-15 | 2023-06-22 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2024256539A1 (en) | 2023-06-15 | 2024-12-19 | Givaudan Sa | Improvements in or relating to organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB201904695D0 (en) | 2019-05-15 |
| BR112021018358A2 (en) | 2021-11-23 |
| CN113646417A (en) | 2021-11-12 |
| PH12021552463A1 (en) | 2022-06-13 |
| MX2021010967A (en) | 2021-10-13 |
| SG11202109838UA (en) | 2021-10-28 |
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