US20100137178A1 - Perfume systems - Google Patents

Perfume systems Download PDF

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Publication number
US20100137178A1
US20100137178A1 US12/628,255 US62825509A US2010137178A1 US 20100137178 A1 US20100137178 A1 US 20100137178A1 US 62825509 A US62825509 A US 62825509A US 2010137178 A1 US2010137178 A1 US 2010137178A1
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US
United States
Prior art keywords
enyl
methyl
methylbut
dimethyl
propan
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.)
Abandoned
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US12/628,255
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English (en)
Inventor
Johan Smets
Hugo Robert Germain Denutte
An Pintens
David Thomas Stanton
Koen Van Aken
Inge Helena Hubert Laureyn
Bram Denolf
Freek Annie Camiel Vrielynck
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Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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.)
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Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US12/628,255 priority Critical patent/US20100137178A1/en
Assigned to THE PROCTER & GAMBLE COMPANY reassignment THE PROCTER & GAMBLE COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DENUTTE, HUGO ROBERT GERMAIN, PINTENS, AN (NMN), Smets, Johan (NMN), DENOLF, BRAM (NMN), LAUREYN, INGE HELENA HUBERT, VAN AKEN, KOEN (NMN), VRIELYNCK, FREEK ANNIE CAMIEL, STANTON, DAVID THOMAS
Publication of US20100137178A1 publication Critical patent/US20100137178A1/en
Priority to US13/616,766 priority patent/US8431520B2/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
    • C11D3/50—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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
    • C07C255/07—Mononitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/225—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/293—Saturated compounds containing keto groups bound to rings to a three- or four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C11B9/0065—Nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products.
  • Consumer products may comprise one or more perfumes and/or perfume delivery systems that can provide a desired scent to such product and/or a situs that is contacted with such a product and/or mask an undesirable odor. While current perfumes and perfume delivery systems provide desirable odors, consumers continue to seek products that have scents that may be longer lasting and that are tailored to their individual desires (see for example USPA 2007/0275866 A1 and U.S. patent application Ser. No. 12/133,866)—unfortunately the pool of perfume raw materials and perfume delivery systems that is available is still too limited to completely meet the perfume community's needs. Thus, perfumers need an ever larger pool of perfume raw materials and perfume delivery systems.
  • perfume raw materials and compositions including the delivery systems, disclosed herein expand the perfume community's options, as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.
  • the present application relates to perfume raw materials, perfume systems and consumer products comprising such perfume raw materials and/or such perfume systems, as well as processes for making and using such perfume raw materials, perfume systems and consumer products.
  • consumer product means baby care, beauty care, fabric & home care, family care, feminine care, health care, snack and/or beverage products or devices generally intended to be used or consumed in the form in which it is sold.
  • Such products include but are not limited to diapers, bibs, wipes; products for and/or methods relating to treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for and/or methods relating to treating fabrics, hard surfaces and any other surfaces in the area of fabric and home care, including: air care including air fresheners and scent delivery systems, car care, dishwashing, fabric conditioning (including softening and/or freshing), laundry detergency, laundry and rinse additive and/or care, hard surface cleaning and/or treatment including floor and toilet bowl cleaners, and other cleaning for consumer or institutional use
  • air care including
  • cleaning and/or treatment composition is a subset of consumer products that includes, unless otherwise indicated, beauty care, fabric & home care products.
  • Such products include, but are not limited to, products for treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for treating fabrics, hard surfaces and any other surfaces in the area of fabric and home care, including: air care including air fresheners and scent delivery systems, car care, dishwashing, fabric conditioning (including softening and/or freshing), laundry detergency, laundry and rinse additive and/or care, hard surface cleaning and/or treatment including floor and toilet bowl cleaners, granular or powder-form all-purpose or “heavy-duty” washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy
  • the term “fabric and/or hard surface cleaning and/or treatment composition” is a subset of cleaning and treatment compositions that includes, unless otherwise indicated, granular or powder-form all-purpose or “heavy-duty” washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy-duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types for household and institutional use; liquid cleaning and disinfecting agents, including antibacterial hand-wash types, cleaning bars, car or carpet shampoos, bathroom cleaners including toilet bowl cleaners; and metal cleaners, fabric conditioning products including softening and/or freshing that may be in liquid, solid and/or dryer sheet form; as well as cleaning auxiliaries such as bleach additives and “stain-stick” or pre-treat types, substrate-laden products such as dryer added sheets, dry and wetted
  • solid includes granular, powder, bar and tablet product forms.
  • fluid includes liquid, gel, paste and gas product forms.
  • situs includes paper products, fabrics, garments, hard surfaces, hair and skin.
  • component or composition levels are in reference to the active portion of that component or composition, and are exclusive of impurities, for example, residual solvents or by-products, which may be present in commercially available sources of such components or compositions.
  • PRMs Suitable Perfume Raw Materials
  • Suitable PRMs include the PRMs listed in Table 1 below and stereoisomers thereof.
  • the PRMs disclosed in Table 1 above may provide one or more of the following benefits at a level that Applicants believe is unexpected in view of PRMs in general: neat product odor; wet fabric odor when applied to a fabric; dry fabric odor when applied to a fabric; reduced leakage from an encapsulate, including an encapsulate such as a perfume microcapsule; increased head space versus neat oil in certain perfume delivery technologies; odor when used in a matrix perfume delivery that is applied to a package; neat product odor when applied to a cleaning and/or treatment composition; fine fragrance composition odor when used in a fine fragrance; dry hair odor when a composition comprising such a PRM is applied to hair; PRM bloom from a solution comprising such a PRM and new PRM character when applied to a situs. Confirmation of such benefits can be obtained by applying standard test methodologies.
  • PRMs and stereoisomers of such PRMs also known as molecules in the examples of the present specification
  • Table 1 The PRMs and stereoisomers of such PRMs (also known as molecules in the examples of the present specification) disclosed in Table 1 above can be made in accordance with the respective teachings found, for example in the examples of the present specification.
  • a PRM having the structure of Table 1 PRM 16, 20, 27, 28, 118, 123 and 140 are disclosed.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in consumer products at levels, based on total consumer product weight of from about 0.0001% to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01% to about 1%.
  • Such PRMs and stereoisomers thereof may be used in combination in the aforementioned consumer product.
  • a consumer product that may comprise one or more PRMs selected from Table 1 PRMs 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 118, 123, 140 and stereoisomers of such PRMs is disclosed.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in cleaning and/or treatment composition at levels, based on total cleaning and treatment products weight of from about 0.0001% to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01% to about 1%.
  • Such PRMs and stereoisomers thereof may be used in combination in the aforementioned cleaning and/treatment compositions.
  • a cleaning and/or treatment composition that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 77, 100, 101, 107, 108, 110, 117, 118, 123, 127, 140 and stereoisomers of such PRMs is disclosed.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in fabric and/or hard surface cleaning and/or treatment compositions at levels, based on total fabric and/or hard surface cleaning and/or treatment composition weight of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%.
  • Such PRMs and stereoisomers thereof may be used in combination in the aforementioned fabric and/or hard surface cleaning and/or treatment compositions.
  • a fabric and/or hard surface cleaning and/or treatment composition that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115,
  • a detergent that may comprise the same level of the PRMs as disclosed for the aforementioned fabric and hard surface cleaning and/or treatment compositions is disclosed.
  • a detergent that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, in highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions, for example highly compacted detergents that may be solids or fluids, at levels, based on total composition weight, of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%.
  • Such PRMs and stereoisomers thereof may be used in combination in the aforementioned highly compacted detergent compositions.
  • Such highly compact detergents typically comprise a higher than normal percentage of active ingredients.
  • a highly compacted detergent that may comprise one or more PRMs selected from Table 1 PRMs and stereoisomers of such PRMs is disclosed.
  • highly compacted a detergent that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95,
  • perfume delivery systems Certain perfume delivery systems, methods of making certain perfume delivery systems and the uses of such perfume delivery systems are disclosed in USPA 2007/0275866 A1. Such perfume delivery systems include:
  • PAD Polymer Assisted Delivery
  • This perfume delivery technology uses polymeric materials to deliver perfume materials.
  • Classical coacervation, water soluble or partly soluble to insoluble charged or neutral polymers, liquid crystals, hot melts, hydrogels, perfumed plastics, microcapsules, nano- and micro-latexes, polymeric film formers, and polymeric absorbents, polymeric adsorbents, etc. are some examples.
  • PAD includes but is not limited to:
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in perfume delivery systems at levels, based on total perfume delivery system weight, of from 0.001% to about 50%, from 0.005% to 30%, from 0.01% to about 10%, from 0.025% to about 5%, or even from 0.025% to about 1%.
  • the perfume delivery systems disclosed herein are suitable for use in consumer products, cleaning and treatment compositions and fabric and hard surface cleaning and/or treatment compositions, detergents, and highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions, for example highly compacted detergents that may be solids or fluids, at levels, based on total consumer product weight, from about 0.001% to about 20%, from about 0.01% to about 10%, from about 0.05% to about 5%, from about 0.1% to about 0.5%.
  • the amount of Table 1 PRMs may be from about 0.1% to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% to about 90%.
  • microcapsules and/or nanocapsules that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108,
  • PRMs 15, 16, 17, 18, 19, 20, 116, 118, 119, 129, 135 and 141 are alcohols.
  • PRMs 28, 29 and 52 are esters.
  • PRMs 34, 73, 74, 75, 76, 77, 91, 101, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 and 161 are nitriles.
  • the amount of total perfume based on total weight of starch encapsulates and starch agglomerates ranges from 0.1% to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% to about 90%.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such starch encapsulates and starch agglomerates. Such PRMs and stereoisomers thereof may be used in combination in such starch encapsulates and starch agglomerates.
  • the amount of total perfume based on total weight of [cyclodextrin-perfume] complexes ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such [cyclodextrin-perfume] complexes. Such PRMs and stereoisomers thereof may be used in combination in such [cyclodextrin-perfume] complexes.
  • the amount of total perfume based on total weight of Polymer Assisted Delivery (PAD) Matrix Systems ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%. In one aspect, the amount of total perfume based on total weight of a hot melt perfume delivery system/perfume loaded plastic Matrix System and ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 10% to about 50%.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Polymer Assisted Delivery (PAD) Matrix Systems, including hot melt perfume delivery system/perfume loaded plastic Matrix Systems.
  • PAD Polymer Assisted Delivery
  • Such PRMs and stereoisomers thereof may be used in combination in such Polymer Assisted Delivery (PAD) Matrix Systems (including hot melt perfume delivery system/perfume loaded plastic Matrix Systems).
  • the amount of total perfume based on total weight of Amine Assisted Delivery (AAD) ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%.
  • the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Amine Assisted Delivery (AAD) systems. Such PRMs and stereoisomers thereof may be used in combination in such Amine Assisted Delivery (AAD) systems.
  • an Amine Assisted Delivery (AAD) system that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109
  • PRMs 15, 16, 17, 18, 19, 20, 116, 118, 119, 129, 135 and 141 are alcohols.
  • PRMs 34, 73, 74, 75, 76, 77, 91, 101, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 and 161 are nitriles.
  • a Pro-Perfume (PP) Amine Reaction Product (ARP) system that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108, 110, 111, 112, 113, 114, 115, 117, 120, 122, 123,
  • PRMs are ketones.
  • the amount of total perfume based on total weight of Pro-Perfume (PP) Amine Reaction Product (ARP) system ranges from 0.1% to about 99%, from about 1% to about 99%, from 5% to about 90%, from 10% to about 75%, from 20% to about 75%, from 25% to about 60%.
  • perfume delivery technologies also known as perfume delivery systems that are disclosed in the present specification may be used in any combination in any type of consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and highly compact detergent.
  • the PRMs disclosed in Table 1 may be used to formulate perfumes. Such perfumes are combinations of PRMs that may comprise a combination of Table 1 PRMs, or one or Table 1 PRMs and one or more additional PRMs. When used in a perfume, the Table 1 PRMs may used, based on total perfume weight, at levels of from about 0.01% to about 50%, from about 0.1% to about 15%, from about 0.1% to about 10% or even from about 0.5% to about 10%. Such perfumes may be used in multiple applications including being applied neat to a situs or used in a consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and/or a highly compact detergent.
  • adjuncts are suitable for use in the instant compositions and may be desirably incorporated in certain embodiments of the invention, for example to assist or enhance performance, for treatment of the substrate to be cleaned, or to modify the aesthetics of the composition as is the case with perfumes, colorants, dyes or the like. It is understood that such adjuncts are in addition to the components that are supplied via Applicants' perfumes and/or perfume systems. The precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the composition and the nature of the operation for which it is to be used.
  • Suitable adjunct materials include, but are not limited to, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic materials, bleach activators, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfume and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments.
  • suitable examples of such other adjuncts and levels of use are found in U.S. Pat. Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B1 that are incorporated by reference.
  • adjunct ingredient is not essential to Applicants' compositions.
  • certain embodiments of Applicants' compositions do not contain one or more of the following adjuncts materials: bleach activators, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay and soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfumes and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments.
  • one or more adjuncts may be present as detailed below:
  • compositions according to the present invention can comprise a surfactant or surfactant system wherein the surfactant can be selected from nonionic and/or anionic and/or cationic surfactants and/or ampholytic and/or zwitterionic and/or semi-polar nonionic surfactants.
  • the surfactant is typically present at a level of from about 0.1%, from about 1%, or even from about 5% by weight of the cleaning compositions to about 99.9%, to about 80%, to about 35%, or even to about 30% by weight of the cleaning compositions.
  • compositions of the present invention can comprise one or more detergent builders or builder systems. When present, the compositions will typically comprise at least about 1% builder, or from about 5% or 10% to about 80%, 50%, or even 30% by weight, of said builder.
  • Builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, alkaline earth and alkali metal carbonates, aluminosilicate builders polycarboxylate compounds.
  • ether hydroxypolycarboxylates copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulphonic acid, and carboxymethyl-oxysuccinic acid
  • the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid
  • polycarboxylates such as mellitic acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.
  • compositions herein may also optionally contain one or more copper, iron and/or manganese chelating agents. If utilized, chelating agents will generally comprise from about 0.1% by weight of the compositions herein to about 15%, or even from about 3.0% to about 15% by weight of the compositions herein.
  • compositions of the present invention may also include one or more dye transfer inhibiting agents.
  • Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof.
  • the dye transfer inhibiting agents are present at levels from about 0.0001%, from about 0.01%, from about 0.05% by weight of the cleaning compositions to about 10%, about 2%, or even about 1% by weight of the cleaning compositions.
  • compositions of the present invention can also contain dispersants.
  • Suitable water-soluble organic materials are the homo- or co-polymeric acids or their salts, in which the polycarboxylic acid may comprise at least two carboxyl radicals separated from each other by not more than two carbon atoms.
  • Enzymes The compositions can comprise one or more detergent enzymes which provide cleaning performance and/or fabric care benefits.
  • suitable enzymes include, but are not limited to, hemicellulases, peroxidases, proteases, cellulases, xylanases, lipases, phospholipases, esterases, cutinases, pectinases, keratanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ -glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase, and amylases, or mixtures thereof.
  • a typical combination is a cocktail of conventional applicable enzymes like protease, lipase, cutinase and/or cellulase in conjunction with amylase.
  • Enzyme Stabilizers Enzymes for use in compositions, for example, detergents can be stabilized by various techniques.
  • the enzymes employed herein can be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished compositions that provide such ions to the enzymes.
  • compositions may include catalytic metal complexes.
  • One type of metal-containing bleach catalyst is a catalyst system comprising a transition metal cation of defined bleach catalytic activity, such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations, an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminum cations, and a sequestrate having defined stability constants for the catalytic and auxiliary metal cations, particularly ethylenediaminetetraacetic acid, ethylenediaminetetra (methyl-enephosphonic acid) and water-soluble salts thereof.
  • a transition metal cation of defined bleach catalytic activity such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations
  • an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminum cations
  • a sequestrate having defined stability constants for the catalytic and
  • compositions herein can be catalyzed by means of a manganese compound.
  • a manganese compound Such compounds and levels of use are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. Pat. No. 5,576,282.
  • Cobalt bleach catalysts useful herein are known, and are described, for example, in U.S. Pat. Nos. 5,597,936 and 5,595,967. Such cobalt catalysts are readily prepared by known procedures, such as taught for example in U.S. Pat. Nos. 5,597,936, and 5,595,967.
  • compositions herein may also suitably include a transition metal complex of a macropolycyclic rigid ligand—abbreviated as “MRL”.
  • MRL macropolycyclic rigid ligand
  • the compositions and cleaning processes herein can be adjusted to provide on the order of at least one part per hundred million of the benefit agent MRL species in the aqueous washing medium, and may provide from about 0.005 ppm to about 25 ppm, from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about 5 ppm, of the MRL in the wash liquor.
  • Suitable transition-metals in the instant transition-metal bleach catalyst include manganese, iron and chromium.
  • Suitable MRL's herein are a special type of ultra-rigid ligand that is cross-bridged such as 5,12-diethyl-1,5,8,12-tetraazabicyclo[6.6.2]hexa-decane.
  • Suitable transition metal MRLs are readily prepared by known procedures, such as taught for example in WO 00/32601, and U.S. Pat. No. 6,225,464.
  • Certain of the consumer products disclosed herein can be used to clean or treat a situs inter alia a surface or fabric.
  • a situs is contacted with an embodiment of Applicants' composition, in neat form or diluted in a liquor, for example, a wash liquor and then the situs may be optionally washed and/or rinsed.
  • a situs is optionally washed and/or rinsed, contacted with a particle according to the present invention or composition comprising said particle and then optionally washed and/or rinsed.
  • washing includes but is not limited to, scrubbing, and mechanical agitation.
  • the fabric may comprise most any fabric capable of being laundered or treated in normal consumer use conditions.
  • Liquors that may comprise the disclosed compositions may have a pH of from about 3 to about 11.5. Such compositions are typically employed at concentrations of from about 500 ppm to about 15,000 ppm in solution.
  • the wash solvent is water
  • the water temperature typically ranges from about 5° C. to about 90° C. and, when the situs comprises a fabric, the water to fabric ratio is typically from about 1:1 to about 30:1.
  • the silica was washed with methyl tert-butyl ether (MTBE; 2*3 mL). The combined organic fractions were mixed with 25 mL of 0.5 M HCl and extracted with MTBE (2*5 mL) and washed with saturated aqueous NaHCO 3 (5 mL) and brine (5 mL). The crude oil was obtained after drying over MgSO 4 , filtration and concentration. Additional flash chromatography was performed to obtain the compound in high purity, with a Biotage PS1: TLC-based method calculated from solvent conditions 80:20-mixture petroleum ether/Ethyl Acetate.
  • Step 2 exemplified for a 24 mmolar scale:
  • the crude oil was obtained after drying over MgSO 4 , filtration and concentration. Then, the crude oil was dissolved again in Et 2 O and kept in the freezer for 16 hours. The white precipitate was filtered of and the filtrate was concentrated. The pure compound was obtained after flash chromatography, performed with a Biotage PS 1: TLC-based method calculated from solvent conditions 9:1-mixture petroleum ether/Ethyl Acetate.
  • the organic layer was extracted with diethyl ether (Et 2 O; 2*15 mL) and washed with aqueous saturated NaHCO 3 (10 mL) and brine (10 mL).
  • the crude oil was obtained after drying over MgSO 4 , filtration and concentration. Then, the crude oil was dissolved again in Et 2 O and kept in the freezer for 16 hours. The white precipitate was filtered of and the filtrate was concentrated at the rotavap.
  • the pure compound was obtained after flash chromatography, performed with a Biotage PS 1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.
  • R 1 Scale time [h] 22 Me 15 mmol 0° C. rt, 72 h 23 Et 10 mmol 0° C. rt, 16 h 24 i-Pr 10 mmol 0° C. rt, 72 h 26 Allyl 20 mmol 0° C. rt, 16 h 25 n-Pr 1 mmol 0° C. rt, 16 h 21 n-Am 1 mmol 0° C. rt, 16 h 27 t-Bu 20 mmol 0° C. rt, 48 h 1 Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.
  • a 2-L flask, dropping funnel, stifling bar and septum were dried in the oven at 80° C. and 20 mbar for 24 h.
  • the glassware was cooled to room temperature under nitrogen atmosphere, before 152 gram of aluminium trichloride (AlCl 3 ; 1.2 equiv) was dissolved in 300 mL of anhydrous benzene.
  • 140 gram of cyclopentylacetyl chloride (1 equiv) were added drop wise and very slowly over a 2 h period to this reaction mixture while the temperature was controlled below 40° C. by the rate of addition of the acid chloride.
  • the reaction start and progress were followed by the gas evolvement.
  • the reaction mixture was continued at 45° C. for 16 h.
  • the reaction mixture was quenched by adding it to a large quantity of crushed ice (1.5 kg). 1 Liter of demineralised water was added, while controlling the temperature with ice. A white suspension was formed.
  • the glassware was washed with 100 mL of methyl tent-butyl ether (MTBE) and the combined organic layers were filtered and extracted with MTBE (2*100 mL). Then the organic layers were washed with aqueous NaHCO 3 solution and brine.
  • the organic fractions were collected, dried over Na 2 SO 4 , filtered and dried in vacuo (70° C. at 15 mbar) to afford a red oil. This oil was mixed with 10 w % of active carbon and stirred at room temperature for 16 h. Then the mixture was filtered over a short Celite path and the glassware and filter were rinsed with 100 mL of ligroin. The organic fractions were combined and dried at the rotavap, affording a yellow oil.
  • MTBE methyl tent-but
  • Biotage 1 chloride rt, 16 h (15 mmol) 9 Cyclopentylacetyl mesitylene 0° C. Biotage 1 chloride rt, 16 h (15 mmol) 1 Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 95:5-mixture petroleum ether/Ethyl Acetate.
  • the organic phase was extracted with aqueous saturated bicarbonate (4*750 mL). Each time, the aqueous phase was washed with toluene (2*100 mL). After this washing, all the organic phases were combined and washed once more with aqueous saturated bicarbonate (750 mL) and with brine (3*250 mL).
  • reaction mixture was quenched in demineralised water with 5 ice cubes in it. A white suspension was formed (exothermic; additional ice cubes were added).
  • the glassware was washed with 25 mL of Et 2 O and the combined organic layers were filtered and extracted with ether (2*20 mL). Then the organic layers were treated with 2*25 mL of aqueous NaHCO 3 solution and this aqueous layer was extracted again with diethyl ether (2*10 mL). Then, the organic fractions were collected, dried over Na 2 SO 4 , filtered and dried in vacuum (low pressure; high temperature resulting in a dark oil formed. The compound was placed in the fridge and solidified after some time. It was tried to purify the ketone via re-crystallisation. First it was dissolved in the minimal amount of Et 2 O. Upon cooling it solidified after a few hours. This procedure was repeated two times resulting in colourless crystals.
  • Compound 52 was synthesized starting from 20 mmol 4,4-dimethyl-3-oxopentanoate.
  • the ⁇ -keto-ester (1 eq.) formed in step 1 was solved in MTBE (0.6 M) and sodium t-butoxide (1.1 eq.) and prenyl bromide (1.5 eq.) were added at room temperature. The resulting mixture was stirred for 16 hours at the same temperature and quenched with an aqueous H 2 SO 4 solution (0.5 M). After extracting the mixture with MTBE, the collected organic layers were dried over MgSO 4 and concentrated under reduced pressure. The resulting oil was purified by column chromatography using a petroleum ether-MTBE mixture (95-5) as eluens. Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.
  • Compound 53 was synthesized starting from 45 mmol 3,3-dimethyl-2-butanone.
  • Compound 63 was synthesized starting from 15 mmol lavandulol.
  • the reaction was quenched with a H 2 SO 4 solution (2M—2 eq.) and stirred at ambient temperature till full hydrolysis of the in situ formed imine was observed.
  • the mixture was then extracted with Et 2 O and washed with a saturated NaHCO 3 aqueous solution.
  • the combined organic phases were dried over MgSO 4 and concentrated under reduced pressure.
  • the resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et 2 O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.
  • the Weinreb amide formed in step 2 was solved in dry THF (0.5 M) and cooled to ⁇ 15° C. A solution of EtMgBr (1 M—1.5 eq.) was added drop wise to the mixture. Complete reaction conversion was observed with GC-MS after 10 minutes stirring at ⁇ 10/ ⁇ 15° C. This reaction mixture was quenched with a saturated aqueous NH 4 Cl solution, extracted with Et 2 O; dried over MgSO 4 and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et 2 O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.
  • Compound 101 was synthesized starting from 100 mmol nitrile [2947-60-6].
  • Compound 125 was synthesized starting from 11 mmol iso-butyronitrile.
  • step 1 The nitrile formed in step 1 was solved in dry THF (0.5 M) and cooled to ⁇ 20° C. A solution of methyllithium (1.3 eq.—1.6 M) was added drop wise. Reaction completion was observed after 10 minutes stifling at ⁇ 20° C. The reaction was quenched with a H 2 SO 4 solution (2M—2 eq.) and stirred at ambient temperature till full hydrolysis of the in situ formed imine was observed (over night ambient temperature). The mixture was then extracted with Et 2 O and washed with a saturated NaHCO 3 aqueous solution. The combined organic phases were dried over MgSO 4 and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether-Et 2 O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.
  • Compound 140 was synthesized starting from 24 mmol acid [6120-95-2].
  • the Weinreb amide formed in step 2 was solved in dry THF (0.5 M) and cooled to ⁇ 15° C. A solution of EtMgBr (1 M—1.5 eq.) was added drop wise to the mixture. Complete reaction conversion was observed with GC-MS after 10 minutes stirring at ⁇ 10/ ⁇ 15° C. This reaction mixture was quenched with a saturated aqueous NH 4 Cl solution, extracted with Et 2 O; dried over MgSO 4 and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether-Et 2 O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.
  • Lupasol WF 50% of Lupasol WF (CAS# 09002-98-6) from BASF, is put at 60° C. in warm water bath for 1 hour before use. Mixing of the two ingredients was done by using the Ultra-Turrax T25 Basic equipment (from IKA) during 5 minutes. When the mixing is finished the sample is put in a warm water bath at 60° C. for ⁇ 12 hours. A homogenous, viscous material is obtained. In the same way as described above different ratios between the components can be used:
  • butyl acrylate-acrylic acid copolymer emulsifier (Colloid C351, 25% solids, pka 4.5-4.7, (Kemira Chemicals, Inc. Kennesaw, Georgia U.S.A.) is dissolved and mixed in 200 grams deionized water. The pH of the solution is adjusted to pH of 4.0 with sodium hydroxide solution. 8 grams of partially methylated methylol melamine resin (Cymel 385, 80% solids, (Cytec Industries West Paterson, N.J., U.S.A.)) is added to the emulsifier solution. 200 grams of perfume oil comprising one or more Table 1 PRMs is added to the previous mixture under mechanical agitation and the temperature is raised to 50° C.
  • perfume oil comprising one or more Table 1 PRMs is added to the previous mixture under mechanical agitation and the temperature is raised to 50° C.
  • the second solution and 4 grams of sodium sulfate salt are added to the emulsion.
  • This second solution contains 10 grams of butyl acrylate-acrylic acid copolymer emulsifier (Colloid C351, 25% solids, pka 4.5-4.7, Kemira), 120 grams of distilled water, sodium hydroxide solution to adjust pH to 4.8, 25 grams of partially methylated methylol melamine resin (Cymel 385, 80% solids, Cytec). This mixture is heated to 70° C. and maintained overnight with continuous stirring to complete the encapsulation process. 23 grams of acetoacetamide (Sigma-Aldrich, Saint Louis, Mo., U.S.A.) is added to the suspension. An average capsule size of 30 um is obtained as analyzed by a Model 780 Accusizer.
  • a mixture comprising 50% of a perfume composition comprising one or more Table 1 PRMs, 40% of carboxyl-terminated Hycar®1300 ⁇ 18 (CAS#0068891-50-9) from Noveon, (put at 60° C. in warm water bath for 1 hour before mixing) and 10% of Lupasol® WF(CAS# 09002-98-6) from BASF (put at 60° C. in warm water bath for 1 hour before mixing).
  • Mixing is achieved by mixing for five minutes using a Ultra-Turrax T25 Basic equipment (from IKA). After mixing, the mixture is put in a warm water bath at 60° C. for ⁇ 12 hours. A homogenous, viscous and sticky material is obtained.
  • Weight % Perfume composition 40 50 60 70 80 Lupasol ® WF 12 10 8 6 4 Hycar ® 48 40 32 24 16 CTBN1300X18 Perfume composition 50 50 50 50 50 50 50 50 50 50 50 50 50 50 50 50 50 50 Lupasol ® WF 2.5 5 7.5 10 12.5 15 17.5 20 Hycar ® CTBN 47.5 45 42.5 40 37.5 35 32.5 30 1300X18
  • Non-limiting examples of product formulations containing PRMs disclosed in the present specification perfume and amines summarized in the following table.
  • Methyl bis(tallow amidoethyl)2-hydroxyethyl ammonium methyl sulfate b Methyl bis(tallow amidoethyl)2-hydroxyethyl ammonium methyl sulfate.
  • c Reaction product of Fatty acid with Methyldiethanolamine in a molar ratio 1.5:1, quaternized with Methylchloride, resulting in a 1:1 molar mixture of N,N-bis(stearoyl-oxy-ethyl) N,N-dimethyl ammonium chloride and N-(stearoyl-oxy-ethyl) N,-hydroxyethyl N,N dimethyl ammonium chloride.
  • d Cationic high amylose maize starch available from National Starch under the trade name CATO ®.
  • e Perfume comprising one or more Table 1 PRMs.
  • f Copolymer of ethylene oxide and terephthalate having the formula described in U.S. Pat. No. 5,574,179 at col.15, lines 1-5, wherein each X is methyl, each n is 40, u is 4, each R1 is essentially 1,4-phenylene moieties, each R2 is essentially ethylene, 1,2-propylene moieties, or mixtures thereof.
  • i KATHON ® CG available from Rohm and Haas Co.
  • PPM is “parts per million.”
  • j Gluteraldehyde k Silicone antifoam agent available from Dow Corning Corp. under the trade name DC2310.
  • l Hydrophobically-modified ethoxylated urethane available from Rohm and Haas under the tradename Aculan 44. *One or more materials comprising an amine moiety as disclosed in the present specification. ⁇ balance
  • HDLs Liquid Laundry Formulations

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US20130012422A1 (en) 2013-01-10
CN102300550B (zh) 2014-04-23
RU2011120488A (ru) 2013-01-10
MX2011005801A (es) 2011-06-20
WO2010065446A3 (fr) 2011-05-26
JP5567029B2 (ja) 2014-08-06
CN102300550A (zh) 2011-12-28
RU2588972C2 (ru) 2016-07-10
CA2744033A1 (fr) 2010-06-10
JP2012510561A (ja) 2012-05-10
EP2362765B1 (fr) 2020-04-08
WO2010065446A2 (fr) 2010-06-10

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