US20120101018A1 - Bis-azo colorants for use as bluing agents - Google Patents

Bis-azo colorants for use as bluing agents Download PDF

Info

Publication number
US20120101018A1
US20120101018A1 US12/910,258 US91025810A US2012101018A1 US 20120101018 A1 US20120101018 A1 US 20120101018A1 US 91025810 A US91025810 A US 91025810A US 2012101018 A1 US2012101018 A1 US 2012101018A1
Authority
US
United States
Prior art keywords
alkyl
bluing agent
laundry care
substituted
care composition
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
Application number
US12/910,258
Other languages
English (en)
Inventor
Gregory Scot Miracle
Robert L. Mahaffey
Xiaoyong Michael Hong
Eduardo Torres
Dominick J. Valenti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
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.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US12/910,258 priority Critical patent/US20120101018A1/en
Assigned to THE PROCTER & GAMBLE COMPANY reassignment THE PROCTER & GAMBLE COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TORRES, EDUARDO (NMN), VALENTI, DOMINICK J., HONG, XIAOYONG MICHAEL, MAHAFFEY, ROBERT L., MIRACLE, GREGORY SCOT
Priority to ARP110103893A priority patent/AR083503A1/es
Priority to BR112013009792A priority patent/BR112013009792A2/pt
Priority to EP11778758.0A priority patent/EP2630226A1/en
Priority to MX2013004463A priority patent/MX357388B/es
Priority to MX2013004461A priority patent/MX357340B/es
Priority to EP11778757.2A priority patent/EP2630225A1/en
Priority to PCT/US2011/057264 priority patent/WO2012054821A1/en
Priority to CN201610101320.5A priority patent/CN105695160B/zh
Priority to CN201180050989.1A priority patent/CN103339245B/zh
Priority to JP2013535118A priority patent/JP5833130B2/ja
Priority to ES11785825T priority patent/ES2699751T3/es
Priority to BR112013009794A priority patent/BR112013009794A2/pt
Priority to MX2013004460A priority patent/MX357342B/es
Priority to PCT/US2011/057270 priority patent/WO2012054823A1/en
Priority to PCT/US2011/057262 priority patent/WO2012054820A1/en
Priority to CN201180050981.5A priority patent/CN103180424B/zh
Priority to CN201180050982XA priority patent/CN103201370A/zh
Priority to CN201180051018.9A priority patent/CN103168097B/zh
Priority to CN201180050993.8A priority patent/CN103180425B/zh
Priority to PCT/US2011/057279 priority patent/WO2012054827A1/en
Priority to EP11779294.5A priority patent/EP2630227B1/en
Priority to BR112013009791-4A priority patent/BR112013009791B1/pt
Priority to PCT/US2011/057290 priority patent/WO2012054835A1/en
Priority to PL11785825T priority patent/PL2630229T3/pl
Priority to BR112013009793A priority patent/BR112013009793A2/pt
Priority to EP11785825.8A priority patent/EP2630229B1/en
Priority to MX2013004462A priority patent/MX357338B/es
Priority to CA2815479A priority patent/CA2815479C/en
Priority to BR112013009798A priority patent/BR112013009798A2/pt
Priority to EP11781907.8A priority patent/EP2630228A1/en
Priority to MX2013004459A priority patent/MX357341B/es
Priority to US13/313,283 priority patent/US9701930B2/en
Priority to US13/313,340 priority patent/US9708573B2/en
Priority to US13/313,310 priority patent/US9708572B2/en
Priority to US13/313,395 priority patent/US9499775B2/en
Priority to US13/313,256 priority patent/US10876079B2/en
Publication of US20120101018A1 publication Critical patent/US20120101018A1/en
Priority to ZA2013/02890A priority patent/ZA201302890B/en
Priority to JP2014249304A priority patent/JP6049679B2/ja
Priority to US14/747,099 priority patent/US20150291918A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/068—Naphthols
    • C09B31/072—Naphthols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile

Definitions

  • This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same.
  • the bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
  • bluing agents As textile substrates age, their color tends to fade or yellow due to exposure to light, air, soil, and natural degradation of the fibers that comprise the substrates. Thus, the purpose of bluing agents is generally to visually brighten these textile substrates and counteract the fading and yellowing of the substrates. Typically, bluing agents may be found in laundry detergents, fabric softeners, or rinse aids and are therefore applied to textile substrates during the laundering process. However, it is important that bluing agents function to brighten treated textile substrates without causing undesirable staining of the textile substrates. Cellulosic substrates, in particular, tend to exhibit a yellow hue after exposure to light, air, and/or soiling. This yellowness is often difficult to reverse by normal laundering procedures.
  • the present invention offers advantages over previous efforts in this area, as this invention takes advantage of compounds having a non-sulfonic acid substituent in the terminal phenyl ring of the bis-azo structure.
  • Sulfonic acid groups are known to promote the deposition and staining of acid dyes on cellulosic fabrics. These groups are also essential for the solubility and compatibility of the dyes in laundry formulations. While it is necessary that bluing agents deposit from wash water, it is undesirable that they stain the fabric by inadvertent contact or by building up over time, i.e. overhueing.
  • the hueing compounds disclosed herein also absorb light at a wavelength appropriate to neutralize the yellowness of cellulosic substrates. These compounds function ideally as bluing agents for cellulosic substrates and may be incorporated into laundry care compositions for use by consumers.
  • This invention relates to laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such laundry care compositions and methods of using the same.
  • the bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
  • alkoxy is intended to include C 1 -C 6 alkoxy and alkoxy derivatives of polyols having repeating units such as butylene oxide, glycidol oxide, ethylene oxide or propylene oxide.
  • alkyl and “alkyl capped” are intended to include C 1 -C 6 alkyl groups.
  • laundry care composition includes, unless otherwise indicated, granular, powder, liquid, gel, paste, unit dose bar form and/or flake type washing agents and/or fabric treatment compositions.
  • fabric treatment composition includes, unless otherwise indicated, fabric softening compositions, fabric enhancing compositions, fabric freshening compositions and combinations there of. Such compositions may be, but need not be rinse added compositions.
  • cellulosic substrates are intended to include any substrate which comprises at least a majority by weight of cellulose.
  • Cellulose may be found in wood, cotton, linen, jute, and hemp.
  • Cellulosic substrates may be in the form of powders, fibers, pulp and articles formed from powders, fibers and pulp.
  • Cellulosic fibers include, without limitation, cotton, rayon (regenerated cellulose), acetate (cellulose acetate), triacetate (cellulose triacetate), and mixtures thereof.
  • Articles formed from cellulosic fibers include textile articles such as fabrics.
  • Articles formed from pulp include paper.
  • test methods disclosed in the Test Methods Section of the present application should be used to determine the respective values of the parameters of Applicants' inventions.
  • 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.
  • the bluing agents employed in the present laundry care compositions may be dyes, pigments, or polymeric colorants comprising a chromophore constituent and a polymeric constituent.
  • the chromophore constituent is characterized in that it absorbs light in the wavelength range of blue, red, violet, purple, or combinations thereof upon exposure to light.
  • the chromophore constituent exhibits an absorbance spectrum maximum from about 520 nanometers to about 640 nanometers in water and/or methanol, and in another aspect, from about 560 nanometers to about 610 nanometers in water and/or methanol.
  • suitable polymeric constituents include polyoxyalkylene chains having multiple repeating units.
  • the polymeric constituents include polyoxyalkylene chains having from 2 to about 30 repeating units, from 2 to about 20 repeating units, from 2 to about 10 repeating units or even from about 3 or 4 to about 6 repeating units.
  • Non-limiting examples of polyoxyalkylene chains include ethylene oxide, propylene oxide, glycidol oxide, butylene oxide and mixtures thereof.
  • the bluing agent employed in the present laundry care compositions may have the following general structure (I):
  • suitable bluing agents may have the following general Structure (II):
  • suitable bluing agents may have the following general Structure (III):
  • said bluing agent may comprise:
  • said bluing agent may comprise a polyoxyalkylene chain having from 2 to about 20 repeating units.
  • said bluing agent may comprise a polyoxyalkylene chain having from 2 to about 10 repeating units.
  • bluing agent may comprise a polyoxyalkylene chain having from about 4 to about 6 repeating units.
  • bluing agent may comprise an alkoxylated bis-azo polymeric colorant.
  • bluing agent's chromophore may exhibit an absorbance spectrum maximum in water of from about 520 nanometers to about 640 nanometers.
  • said bluing agent's chromophore may exhibit an absorbance spectrum maximum in water of from about 560 nanometers to about 610 nanometers.
  • said bluing agent may exhibit an absolute hue angle in the range of 265° to 310°.
  • bluing agent may exhibit an absolute hue angle in the range of 273° to 287°.
  • said bluing agent may have the following structure:
  • R 1 is alkoxy and R 2 is alkyl.
  • suitable bluing agents include, but are not limited to the following structures:
  • the base utilized in the first step of the reaction may be selected from sodium carbonate, sodium acetate, sodium hydroxide, or other cationic salts of these respective bases, and tertiary amines.
  • Acid hydrolysis may be carried out utilizing a strong acid such as hydrochloric acid or sulfuric acid.
  • the bis-azo colorants disclosed herein may be made according to various procedures known in the art and/or in accordance with the examples of the present invention.
  • coupling may be carried out using polyalkyleneoxy substituted aniline compounds derived by known procedures from starting materials such as 4-methyoxy-2-nitrophenol or 4-methyl-2-nitrophenol, both of which are available from VWR International, LLC (West Chester, Pa., USA).
  • any of the bluing agents described in the present specification may be incorporated into laundry care compositions including but not limited to laundry detergents and fabric care compositions.
  • the laundry care compositions including laundry detergents may be in solid or liquid form, including a gel form.
  • Such compositions may comprise one or more of said bluing agents and a laundry care ingredient.
  • the bluing agents may be added to substrates using a variety of application techniques. For instance, for application to cellulose-containing textile substrates, the bluing agent may be included as a component of a laundry detergent. Thus, application to a cellulose-containing textile substrate actually occurs when a consumer adds laundry detergent to a washing machine.
  • the bluing agent may be present in the laundry detergent composition in an amount from about 0.0001% to about 10% by weight of the composition, from about 0.0001% to about 5% by weight of the composition, and even from about 0.0001% to about 1% by weight of the composition.
  • the laundry detergent composition typically comprises a surfactant in an amount sufficient to provide desired cleaning properties.
  • the laundry detergent composition may comprise, based on total laundry detergent composition weight, from about 5% to about 90% of the surfactant, from about 5% to about 70% of the surfactant, or even from about 5% to about 40% of the surfactant.
  • the surfactant may comprise anionic, nonionic, cationic, zwitterionic and/or amphoteric surfactants.
  • the detergent composition comprises anionic surfactant, nonionic surfactant, or mixtures thereof.
  • Fabric care compositions are typically added in the rinse cycle, which is after the detergent solution has been used and replaced with the rinsing solution in typical laundering processes.
  • the fabric care compositions disclosed herein may be comprise a rinse added fabric softening active and a suitable bluing agent as disclosed in the present specification
  • the fabric care composition may comprise, based on total fabric care composition weight, from about 1% to about 90%, or from about 5% to about 50% fabric softening active.
  • the bluing agent may be present in the fabric care composition in an amount from about 0.5 ppb to about 50 ppm, or from about 0.5 ppm to about 30 ppm.
  • a laundry care composition comprising a laundry care ingredient and a bluing agent comprising:
  • said bluing agent comprises a polyoxyalkylene chain having from 2 to about 30 repeating units.
  • said bluing agent comprises a polyoxyalkylene chain having from 2 to about 20 repeating units.
  • said bluing agent comprises a polyoxyalkylene chain having from 2 to about 10 repeating units.
  • bluing agent comprises a polyoxyalkylene chain having from about 4 to about 6 repeating units.
  • bluing agent comprises an alkoxylated bis-azo polymeric colorant.
  • bluing agent's chromophore exhibits an absorbance spectrum maximum in water of from about 520 nanometers to about 640 nanometers.
  • said bluing agent's chromophore exhibits an absorbance spectrum maximum in water of from about 560 nanometers to about 610 nanometers.
  • said bluing agent exhibits an absolute hue angle in the range of 265° to 310°.
  • said bluing agent has the following structure:
  • R 1 is alkoxy and R 2 is alkyl.
  • laundry care ingredients While not essential for the purposes of the present invention, the non-limiting list of laundry care ingredients illustrated hereinafter are suitable for use in the laundry care compositions and may be desirably incorporated in certain aspects 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 ingredients are in addition to the components that were previously listed for any particular aspect. The total amount of such adjuncts may range, once the amount of dye is taken into consideration from about 90% to about 99.99999995% by weight of the laundry care composition.
  • Suitable laundry care ingredients include, but are not limited to, fabric softening actives, polymers, for example cationic polymers, 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.
  • the laundry care ingredients are not essential to Applicants' laundry care compositions.
  • certain aspects of Applicants' compositions do not contain one or more of the following adjuncts materials: fabric softening actives, 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:
  • Suitable anionic surfactants useful herein can comprise any of the conventional anionic surfactant types typically used in liquid detergent products. These include the alkyl benzene sulfonic acids and their salts as well as alkoxylated or non-alkoxylated alkyl sulfate materials.
  • Exemplary anionic surfactants are the alkali metal salts of C 10 -C 16 alkyl benzene sulfonic acids, or C 11 -C 14 alkyl benzene sulfonic acids.
  • the alkyl group is linear and such linear alkyl benzene sulfonates are known as “LAS”.
  • Alkyl benzene sulfonates, and particularly LAS, are well known in the art.
  • Such surfactants and their preparation are described for example in U.S. Pat. Nos. 2,220,099 and 2,477,383.
  • sodium and potassium linear straight chain alkylbenzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 to 14.
  • Sodium C 11 -C 14 e.g., C 12
  • LAS is a specific example of such surfactants.
  • anionic surfactant comprises ethoxylated alkyl sulfate surfactants.
  • Such materials also known as alkyl ether sulfates or alkyl polyethoxylate sulfates, are those which correspond to the formula: R′—O—(C 2 H 4 O) n —SO 3 M wherein R′ is a C 8 -C 20 alkyl group, n is from about 1 to 20, and M is a salt-forming cation.
  • R′ is C 10 -C 18 alkyl, n is from about 1 to 15, and M is sodium, potassium, ammonium, alkylammonium, or alkanolammonium.
  • R′ is a C 12 -C 16 , n is from about 1 to 6 and M is sodium.
  • non-alkoxylated, e.g., non-ethoxylated, alkyl ether sulfate surfactants are those produced by the sulfation of higher C 8 -C 20 fatty alcohols.
  • Conventional primary alkyl sulfate surfactants have the general formula: ROSO 3 -M + wherein R is typically a linear C 8 -C 20 hydrocarbyl group, which may be straight chain or branched chain, and M is a water-solubilizing cation.
  • R is a C 10 -C 15 alkyl
  • M is alkali metal, more specifically R is C 12 -C 14 and M is sodium.
  • anionic surfactants useful herein include: a) C 11 -C 18 alkyl benzene sulfonates (LAS); b) C 10 -C 20 primary, branched-chain and random alkyl sulfates (AS); c) C 10 -C 18 secondary (2,3) alkyl sulfates having formulae (I) and (II): wherein M in formulae (I) and (II) is hydrogen or a cation which provides charge neutrality, and all M units, whether associated with a surfactant or adjunct ingredient, can either be a hydrogen atom or a cation depending upon the form isolated by the artisan or the relative pH of the system wherein the compound is used, with non-limiting examples of suitable cations including sodium, potassium, ammonium, and mixtures thereof, and x is an integer of at least about 7, or at least about 9, and y is an integer of at least 8, or at least about 9; d) C 10 -C 18 alkyl alkyl alkyl al
  • MLAS modified alkylbenzene sulfonate
  • MES methyl ester sulfonate
  • AOS alpha-olefin sulfonate
  • Suitable nonionic surfactants useful herein can comprise any of the conventional nonionic surfactant types typically used in liquid detergent products. These include alkoxylated fatty alcohols and amine oxide surfactants. In one aspect, for use in the liquid detergent products herein are those nonionic surfactants which are normally liquid.
  • Suitable nonionic surfactants for use herein include the alcohol alkoxylate nonionic surfactants.
  • Alcohol alkoxylates are materials which correspond to the general formula: R 1 (C m H 2m O) n OH wherein R 1 is a C 8 -C 16 alkyl group, m is from 2 to 4, and n ranges from about 2 to 12.
  • R 1 is an alkyl group, which may be primary or secondary, that comprises from about 9 to 15 carbon atoms, or from about 10 to 14 carbon atoms.
  • the alkoxylated fatty alcohols will also be ethoxylated materials that contain from about 2 to 12 ethylene oxide moieties per molecule, or from about 3 to 10 ethylene oxide moieties per molecule.
  • alkoxylated fatty alcohol materials useful in the liquid detergent compositions herein will frequently have a hydrophilic-lipophilic balance (HLB) which ranges from about 3 to 17 from about 6 to 15, or from about 8 to 15.
  • HLB hydrophilic-lipophilic balance
  • Alkoxylated fatty alcohol nonionic surfactants have been marketed under the tradenames Neodol and Dobanol by the Shell Chemical Company.
  • Nonionic surfactant useful herein comprises the amine oxide surfactants.
  • Amine oxides are materials which are often referred to in the art as “semi-polar” nonionics.
  • Amine oxides have the formula: R(EO) x (PO) y (BO) z N(O)(CH 2 R) 2 .qH 2 O.
  • R is a relatively long-chain hydrocarbyl moiety which can be saturated or unsaturated, linear or branched, and can contain from 8 to 20, 10 to 16 carbon atoms, or is a C 12 -C 16 primary alkyl.
  • R′ is a short-chain moiety, in one aspect R′ may be selected from hydrogen, methyl and —CH 2 OH.
  • EO is ethyleneoxy
  • PO propyleneneoxy
  • BO butyleneoxy.
  • Amine oxide surfactants are illustrated by C 12-14 alkyldimethyl amine oxide.
  • Non-limiting examples of nonionic surfactants include: a) C 12 -C 18 alkyl ethoxylates, such as, NEODOL® nonionic surfactants from Shell; b) C 6 -C 12 alkyl phenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; c) C 12 -C 18 alcohol and C 6 -C 12 alkyl phenol condensates with ethylene oxide/propylene oxide block polymers such as Pluronic® from BASF; d) C 14 -C 22 mid-chain branched alcohols, BA, as discussed in U.S. Pat. No.
  • the detersive surfactant component may comprise combinations of anionic and nonionic surfactant materials.
  • the weight ratio of anionic to nonionic will typically range from 10:90 to 90:10, more typically from 30:70 to 70:30.
  • Cationic surfactants are well known in the art and non-limiting examples of these include quaternary ammonium surfactants, which can have up to 26 carbon atoms. Additional examples include a) alkoxylate quaternary ammonium (AQA) surfactants as discussed in U.S. Pat. No. 6,136,769; b) dimethyl hydroxyethyl quaternary ammonium as discussed in U.S. Pat. No. 6,004,922; c) polyamine cationic surfactants as discussed in WO 98/35002, WO 98/35003, WO 98/35004, WO 98/35005, and WO 98/35006; d) cationic ester surfactants as discussed in U.S. Pat.
  • AQA alkoxylate quaternary ammonium
  • Non-limiting examples of zwitterionic surfactants include derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds. See U.S. Pat. No. 3,929,678 to Laughlin et al., issued Dec.
  • betaine including alkyl dimethyl betaine and cocodimethyl amidopropyl betaine, C 8 to C 18 (in one aspect C 12 to C 18 ) amine oxides and sulfo and hydroxy betaines, such as N-alkyl-N,N-dimethylammino-1-propane sulfonate where the alkyl group can be C 8 to C 18 , or C 10 to C 14 .
  • Non-limiting examples of ampholytic surfactants include aliphatic derivatives of secondary or tertiary amines, or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic radical can be straight- or branched-chain.
  • One of the aliphatic substituents comprises at least about 8 carbon atoms, typically from about 8 to about 18 carbon atoms, and at least one comprises an anionic water-solubilizing group, e.g. carboxy, sulfonate, sulfate. See U.S. Pat. No. 3,929,678 to Laughlin et al., issued Dec. 30, 1975 at column 19, lines 18-35, for examples of ampholytic surfactants.
  • the laundry care compositions may be in the form of a solid, either in tablet or particulate form, including, but not limited to particles, flakes, sheets, or the like, or the compositions may be in the form of a liquid.
  • the liquid detergent compositions may comprise an aqueous, non-surface active liquid carrier.
  • the amount of the aqueous, non-surface active liquid carrier employed in the compositions herein will be effective to solubilize, suspend or disperse the composition components.
  • the liquid detergent compositions may comprise, based on total liquid detergent composition weight, from about 5% to about 90%, from about 10% to about 70%, or from about 20% to about 70% of the aqueous, non-surface active liquid carrier.
  • aqueous, non-surface active liquid carrier is typically water. Accordingly, the aqueous, non-surface active liquid carrier component will generally be mostly, if not completely, comprised of water. While other types of water-miscible liquids, such alkanols, diols, other polyols, ethers, amines, and the like, have been conventionally been added to liquid detergent compositions as co-solvents or stabilizers, for purposes of the present invention, the utilization of such water-miscible liquids typically is minimized to hold down composition cost. Accordingly, the aqueous liquid carrier component of the liquid detergent products herein will generally comprise water present in concentrations ranging from about 5% to about 90%, or from about 5% to about 70%, by weight of the liquid detergent composition.
  • the cleaning compositions of the present invention may comprise one or more bleaching agents.
  • Suitable bleaching agents other than bleaching catalysts include photobleaches, bleach activators, hydrogen peroxide, sources of hydrogen peroxide, pre-formed 5 peracids and mixtures thereof.
  • the compositions of the present invention may comprise from about 0.1% to about 50% or even from about 0.1% to about 25% bleaching agent by weight of the subject cleaning composition.
  • suitable bleaching agents include:
  • photobleaches for example sulfonated zinc phthalocyanine
  • Suitable preformed peracids include, but are not limited to, compounds selected from the group consisting of percarboxylic acids and salts, percarbonic acids and salts, perimidic acids and salts, peroxymonosulfuric acids and salts, for example, Oxzone®, and mixtures thereof.
  • Suitable percarboxylic acids include hydrophobic and hydrophilic peracids having the formula R—(C ⁇ O)O—O-M wherein R is an alkyl group, optionally branched, having, when the peracid is hydrophobic, from 6 to 14 carbon atoms, or from 8 to 12 carbon atoms and, when the peracid is hydrophilic, less than 6 carbon atoms or even less than 4 carbon atoms; and M is a counterion, for example, sodium, potassium or hydrogen;
  • inorganic perhydrate salts including alkali metal salts such as sodium salts of perborate (usually mono- or tetra-hydrate), percarbonate, persulphate, perphosphate, persilicate salts and mixtures thereof.
  • the inorganic perhydrate salts are selected from the group consisting of sodium salts of perborate, percarbonate and mixtures thereof.
  • inorganic perhydrate salts are typically present in amounts of from 0.05 to 40 wt %, or 1 to 30 wt % of the overall composition and are typically incorporated into such compositions as a crystalline solid that may be coated. Suitable coatings include, inorganic salts such as alkali metal silicate, carbonate or borate salts or mixtures thereof, or organic materials such as water-soluble or dispersible polymers, waxes, oils or fatty soaps; and
  • bleach activators having R—(C ⁇ O)-L wherein R is an alkyl group, optionally branched, having, when the bleach activator is hydrophobic, from 6 to 14 carbon atoms, or from 8 to 12 carbon atoms and, when the bleach activator is hydrophilic, less than 6 carbon atoms or even less than 4 carbon atoms; and L is leaving group.
  • suitable leaving groups are benzoic acid and derivatives thereof—especially benzene sulphonate.
  • Suitable bleach activators include dodecanoyl oxybenzene sulphonate, decanoyl oxybenzene sulphonate, decanoyl oxybenzoic acid or salts thereof, 3,5,5-trimethyl hexanoyloxybenzene sulphonate, tetraacetyl ethylene diamine (TAED) and nonanoyloxybenzene sulphonate (NOBS).
  • TAED tetraacetyl ethylene diamine
  • NOBS nonanoyloxybenzene sulphonate
  • Suitable bleach activators are also disclosed in WO 98/17767. While any suitable bleach activator may be employed, in one aspect of the invention the subject cleaning composition may comprise NOBS, TAED or mixtures thereof.
  • the peracid and/or bleach activator is generally present in the composition in an amount of from about 0.1 to about 60 wt %, from about 0.5 to about 40 wt % or even from about 0.6 to about 10 wt % based on the composition.
  • One or more hydrophobic peracids or precursors thereof may be used in combination with one or more hydrophilic peracid or precursor thereof.
  • the amounts of hydrogen peroxide source and peracid or bleach activator may be selected such that the molar ratio of available oxygen (from the peroxide source) to peracid is from 1:1 to 35:1, or even 2:1 to 10:1.
  • Bleach Boosting Compounds The compositions herein may comprise one or more bleach boosting compounds. Bleach boosting compounds provide increased bleaching effectiveness in lower temperature applications. The bleach boosters act in conjunction with conventional peroxygen bleaching sources to provide increased bleaching effectiveness. This is normally accomplished through in situ formation of an active oxygen transfer agent such as a dioxirane, an oxaziridine, or an oxaziridinium. Alternatively, preformed dioxiranes, oxaziridines and oxaziridiniums may be used.
  • an active oxygen transfer agent such as a dioxirane, an oxaziridine, or an oxaziridinium.
  • preformed dioxiranes, oxaziridines and oxaziridiniums may be used.
  • suitable bleach boosting compounds for use in accordance with the present invention are cationic imines, zwitterionic imines, anionic imines and/or polyionic imines having a net charge of from about +3 to about ⁇ 3, and mixtures thereof.
  • imine bleach boosting compounds of the present invention include those of the general structure:
  • R 1 -R 4 may be a hydrogen or an unsubstituted or substituted radical selected from the group consisting of phenyl, aryl, heterocyclic ring, alkyl and cycloalkyl radicals.
  • Suitable bleach boosting compounds include zwitterionic bleach boosters zwitterionic bleach boosters, which are described in U.S. Pat. Nos. 5,576,282 and 5,718,614.
  • Other bleach boosting compounds include cationic bleach boosters described in U.S. Pat. Nos. 5,360,569; 5,442,066; 5,478,357; 5,370,826; 5,482,515; 5,550,256; and WO 95/13351, WO 95/13352, and WO 95/13353.
  • Peroxygen sources are well-known in the art and the peroxygen source employed in the present invention may comprise any of these well known sources, including peroxygen compounds as well as compounds, which under consumer use conditions, provide an effective amount of peroxygen in situ.
  • the peroxygen source may include a hydrogen peroxide source, the in situ formation of a peracid anion through the reaction of a hydrogen peroxide source and a bleach activator, preformed peracid compounds or mixtures of suitable peroxygen sources.
  • the bleach boosting compounds when present, are typically employed in conjunction with a peroxygen source in the bleaching systems of the present invention.
  • Enzyme Bleaching Enzymatic systems may be used as bleaching agents.
  • the hydrogen peroxide may also be present by adding an enzymatic system (i.e. an enzyme and a substrate therefore) which is capable of generating hydrogen peroxide at the beginning or during the washing and/or rinsing process.
  • an enzymatic system i.e. an enzyme and a substrate therefore
  • Such enzymatic systems are disclosed in EP Patent Application 91202655.6 filed Oct. 9, 1991.
  • compositions and methods may utilize alternative bleach systems such as ozone, chlorine dioxide and the like.
  • Bleaching with ozone may be accomplished by introducing ozone-containing gas having ozone content from about 20 to about 300 g/m 3 into the solution that is to contact the fabrics.
  • the gas:liquid ratio in the solution should be maintained from about 1:2.5 to about 1:6.
  • U.S. Pat. No. 5,346,588 describes a process for the utilization of ozone as an alternative to conventional bleach systems and is herein incorporated by reference.
  • the fabric softening active is a quaternary ammonium compound suitable for softening fabric in a rinse step.
  • the FSA is formed from a reaction product of a fatty acid and an aminoalcohol obtaining mixtures of mono-, di-, and, in one aspect, triester compounds.
  • the FSA comprises one or more softener quaternary ammonium compounds such, but not limited to, as a monoalkyquaternary ammonium compound, a diamido quaternary compound and a diester quaternary ammonium compound, or a combination thereof.
  • the FSA comprises a diester quaternary ammonium (hereinafter “DQA”) compound composition.
  • DQA compounds compositions also encompasses a description of diamido FSAs and FSAs with mixed amido and ester linkages as well as the aforementioned diester linkages, all herein referred to as DQA.
  • DQA (1) suitable as a FSA in the present CFSC includes a compound comprising the formula:
  • each R substituent is either hydrogen, a short chain C 1 -C 6 , for example C 1 -C 3 alkyl or hydroxyalkyl group, e.g., methyl, ethyl, propyl, hydroxyethyl, and the like, poly (C 2-3 alkoxy), for example.
  • Suitable DQA compounds are typically made by reacting alkanolamines such as MDEA (methyldiethanolamine) and TEA (triethanolamine) with fatty acids.
  • alkanolamines such as MDEA (methyldiethanolamine) and TEA (triethanolamine)
  • Some materials that typically result from such reactions include N,N-di(acyl-oxyethyl)-N,N-dimethylammonium chloride or N,N-di(acyl-oxyethyl)-N,N-methylhydroxyethylammonium methylsulfate
  • the acyl group is derived from animal fats, unsaturated, and polyunsaturated, fatty acids, e.g., tallow, hardened tallow, oleic acid, and/or partially hydrogenated fatty acids, derived from vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice
  • the FSA comprises other actives in addition to DQA (1) or DQA.
  • the FSA comprises only DQA (1) or DQA and is free or essentially free of any other quaternary ammonium compounds or other actives.
  • the FSA comprises the precursor amine that is used to produce the DQA.
  • the FSA comprises a compound, identified as DTTMAC comprising the formula:
  • each R 1 is a C 6 -C 22 , or C 14 -C 20 , but no more than one being less than about C 12 and then the other is at least about 16, hydrocarbyl, or substituted hydrocarbyl substituent, for example, C 10 -C 20 alkyl or alkenyl (unsaturated alkyl, including polyunsaturated alkyl, also referred to sometimes as “alkylene”), in one aspect C 12 -C 18 alkyl or alkenyl, and branch or unbranched.
  • the Iodine Value (IV) of the FSA is from about 1 to 70; each R is H or a short chain C 1 -C 6 , or C 1 -C 3 alkyl or hydroxyalkyl group, e.g., methyl, ethyl, propyl, hydroxyethyl, and the like, benzyl, or (R 20 ) 2-4 H where each R 2 is a C 1-6 alkylene group; and A ⁇ is a softener compatible anion, suitable anions include chloride, bromide, methylsulfate, ethylsulfate, sulfate, phosphate, or nitrate; in one aspect the anions are chloride or methyl sulfate.
  • FSAs include dialkydimethylammonium salts and dialkylenedimethylammonium salts such as ditallowedimethylammonium and ditallowedimethylammonium methylsulfate.
  • dialkylenedimethylammonium salts examples include di-hydrogenated tallow dimethyl ammonium chloride and ditallowedimethyl ammonium chloride available from Degussa under the trade names Adogen® 442 and Adogen® 470 respectively.
  • the FSA comprises other actives in addition to DTTMAC.
  • the FSA comprises only compounds of the DTTMAC and is free or essentially free of any other quaternary ammonium compounds or other actives.
  • the FSA comprises an FSA described in U.S. Pat. Pub. No. 2004/0204337 A1, published Oct. 14, 2004 to Corona et al., from paragraphs 30-79.
  • the FSA is one described in U.S. Pat. Pub. No. 2004/0229769 A1, published Nov. 18, 2005, to Smith et al., on paragraphs 26-31; or U.S. Pat. No. 6,494,920, at column 1, line 51 et seq. detailing an “esterquat” or a quaternized fatty acid triethanolamine ester salt.
  • the FSA is chosen from at least one of the following: ditallowoyloxyethyl dimethyl ammonium chloride, dihydrogenated-tallowoyloxyethyl dimethyl ammonium chloride, ditallow dimethyl ammonium chloride, ditallowoyloxyethyl dimethyl ammonium methyl sulfate, dihydrogenated-tallowoyloxyethyl dimethyl ammonium chloride, dihydrogenated-tallowoyloxyethyl dimethyl ammonium chloride, or combinations thereof.
  • the FSA may also include amide containing compound compositions.
  • diamide comprising compounds may include but not limited to methyl-bis(tallowamidoethyl)-2-hydroxyethylammonium methyl sulfate (available from Degussa under the trade names Varisoft 110 and Varisoft 222).
  • An example of an amide-ester containing compound is N-[3-(stearoylamino)propyl]-N-[2-(stearoyloxy)ethoxy)ethyl)]-N-methylamine.
  • a rinse added fabric softening composition further comprising a cationic starch.
  • Cationic starches are disclosed in US 2004/0204337 A1.
  • the rinse added fabric softening composition comprises from about 0.1% to about 7% of cationic starch by weight of the fabric softening composition.
  • the cationic starch is HCP401 from National Starch.
  • 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.
  • the liquid detergent compositions are in the form of an aqueous solution or uniform dispersion or suspension of surfactant, bluing agent, and certain optional other ingredients, some of which may normally be in solid form, that have been combined with the normally liquid components of the composition, such as the liquid alcohol ethoxylate nonionic, the aqueous liquid carrier, and any other normally liquid optional ingredients.
  • a solution, dispersion or suspension will be acceptably phase stable and will typically have a viscosity which ranges from about 100 to 600 cps, or from about 150 to 400 cps. For purposes of this invention, viscosity is measured with a Brookfield LVDV-II+ viscometer apparatus using a #21 spindle.
  • the liquid detergent compositions herein can be prepared by combining the components thereof in any convenient order and by mixing, e.g., agitating, the resulting component combination to form a phase stable liquid detergent composition.
  • a liquid matrix is formed containing at least a major proportion, or even substantially all, of the liquid components, e.g., nonionic surfactant, the non-surface active liquid carriers and other optional liquid components, with the liquid components being thoroughly admixed by imparting shear agitation to this liquid combination.
  • the liquid components e.g., nonionic surfactant, the non-surface active liquid carriers and other optional liquid components
  • shear agitation for example, rapid stirring with a mechanical stirrer may usefully be employed. While shear agitation is maintained, substantially all of any anionic surfactants and the solid form ingredients can be added.
  • Agitation of the mixture is continued, and if necessary, can be increased at this point to form a solution or a uniform dispersion of insoluble solid phase particulates within the liquid phase.
  • particles of any enzyme material to be included e.g., enzyme prills, are incorporated.
  • one or more of the solid components may be added to the agitated mixture as a solution or slurry of particles premixed with a minor portion of one or more of the liquid components.
  • agitation of the mixture is continued for a period of time sufficient to form compositions having the requisite viscosity and phase stability characteristics. Frequently this will involve agitation for a period of from about 30 to 60 minutes.
  • the bluing agent is first combined with one or more liquid components to form a bluing agent premix, and this bluing agent premix is added to a composition formulation containing a substantial portion, for example more than 50% by weight, more specifically, more than 70% by weight, and yet more specifically, more than 90% by weight, of the balance of components of the laundry detergent composition.
  • a composition formulation containing a substantial portion, for example more than 50% by weight, more specifically, more than 70% by weight, and yet more specifically, more than 90% by weight, of the balance of components of the laundry detergent composition.
  • both the bluing agent premix and the enzyme component are added at a final stage of component additions.
  • the bluing agent is encapsulated prior to addition to the detergent composition, the encapsulated bluing agent is suspended in a structured liquid, and the suspension is added to a composition formulation containing a substantial portion of the balance of components of the laundry detergent composition.
  • the detergent compositions may be in a solid form. Suitable solid forms include tablets and particulate forms, for example, granular particles, flakes or sheets. Various techniques for forming detergent compositions in such solid forms are well known in the art and may be used herein.
  • the bluing agent is provided in particulate form, optionally including additional but not all components of the laundry detergent composition.
  • the bluing agent particulate is combined with one or more additional particulates containing a balance of components of the laundry detergent composition.
  • the bluing agent optionally including additional but not all components of the laundry detergent composition, may be provided in an encapsulated form, and the bluing agent encapsulate is combined with particulates containing a substantial balance of components of the laundry detergent composition.
  • compositions of this invention can be used to form aqueous washing solutions for use in the laundering of fabrics.
  • an effective amount of such compositions is added to water, for example in a conventional fabric laundering automatic washing machine, to form such aqueous laundering solutions.
  • the aqueous washing solution so formed is then contacted, typically under agitation, with the fabrics to be laundered therewith.
  • An effective amount of the liquid detergent compositions herein added to water to form aqueous laundering solutions can comprise amounts sufficient to form from about 500 to 7,000 ppm of composition in aqueous washing solution, or from about 1,000 to 3,000 ppm of the detergent compositions herein will be provided in aqueous washing solution.
  • 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' consumer product, 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 an aspect of the consumer product 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.
  • the situs comprises a fabric
  • the water to fabric ratio is typically from about 1:1 to about 30:1.
  • the following bis-azo colorants are prepared as described herein.
  • the UV-visible spectrum of each colorant is determined by dissolving it in a suitable solvent, typically water or methanol, at a concentration that gives an absorbance at the lambda max of less than 1.0 at a path length of 1.0 cm.
  • a Beckman Coulter DU 800 spectrophotometer was used to measure the UV-visible spectrum and determine the lambda max (“ ⁇ max ”) of each sample.
  • the resulting diazonium salt is added to a cooled solution of 6.85 grams of 2-methoxy-5-methylaniline in dilute aqueous hydrochloric acid resulting in a deep orange red product.
  • This product is further diazotized at 0-5° C. by adding 3.58 grams of sodium nitrite with additional hydrochloric acid as necessary to keep the pH at ⁇ 2.
  • the mixture is stirred for 2 hours.
  • the resulting diazonium salt is added to a cooled (0-5° C.) aqueous solution of H-acid in water containing sufficient sodium hydroxide to dissolve the H-acid.
  • the pH of the reaction mixture is kept at 10-12 during the addition of the diazonium salt by adding sodium hydroxide solution as necessary. This resulted in a solution of the deep violet colored product represented as Formula BA4 herein.
  • the product has a ⁇ max of 569 nm in water.
  • the product represented as Formula BA13 herein is prepared in a similar manner to Example 1 except 7.65 grams of 2,5-dimethoxyaniline are substituted for 2-methoxy-5-methylaniline.
  • the product has a ⁇ max of 583 nm in water.
  • the product represented as Formula BA31 herein is prepared in a similar manner to Example 1 except 9.75 grams of N-acetyl-H acid are substituted for H acid.
  • the product has a ⁇ max of 560 nm in water.
  • the product represented as Formula BA58 herein is prepared in a similar manner to Example 1 except 15.75 grams of N-phenyl J acid are substituted for H acid.
  • the product has a ⁇ max of 545 nm in water.
  • the product represented as Formula BA herein is prepared in a similar manner to Example 2 except 15.75 grams of N-phenyl J acid are substituted for H acid.
  • the product has a ⁇ max of 558 nm in water.
  • the product represented as Formula BA5 herein is prepared in a similar manner to Example 1 except 8.85 grams of 3-(2-(2-methoxyethoxy)ethoxy)propylamine are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 577 nm in water.
  • the product represented as Formula BA14 herein is prepared in a similar manner to Example 6 except 7.65 grams of 2,5-dimethoxyaniline are substituted for 2-methoxy-5-methylaniline.
  • the product has a ⁇ max of 608 nm in methanol.
  • the product represented as Formula BA12 herein is prepared in a similar manner to Example 7 except 30.70 grams of Surfonamine® B60 are substituted for 3-(2-(2-methoxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 590 nm in water.
  • the product represented as Formula BA2 herein is prepared in a similar manner to Example 6 except 52.90 grams of Surfonamine® L100 are substituted for 3-(2-(2-methoxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 581 nm in water.
  • the product represented as Formula BAH herein is prepared in a similar manner to Example 8 except 52.90 grams of Surfonamine® L100 are substituted for 3-(2-(2-methoxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 578 nm in water.
  • the pH is kept at 10-12 by the addition of aqueous sodium hydroxide solution. This resulted in a violet colored product represented as Formula BA18 herein.
  • the product has a ⁇ max of 574 nm in methanol.
  • the product represented as Formula BA15 herein is prepared in a similar manner to Example 2 except 27.45 grams of p-polyalkyleneoxyphenylamine are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 574 nm in methanol.
  • the product represented as Formula BA17 herein is prepared in a similar manner to Example 2 except 5.25 grams of diethanolamine are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 581 nm in water.
  • the product represented as Formula BA1 herein is prepared in a similar manner to Example 1 except 35.75 grams of Jeffamine® M715 are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 578 nm in water.
  • the product represented as Formula BA28 herein is prepared in a similar manner to Example 3 except 35.75 grams of Jeffamine® M715 are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 563 nm in water.
  • the product represented as Formula BASS herein is prepared in a similar manner to Example 4 except 35.75 grams of Jeffamine® M715 are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 545 nm in methanol.
  • the product represented as Formula BA34 herein is prepared in a similar manner to Example 3 except 3.65 grams of diethylamine are substituted for 3-(2-(2-hydroxyethoxy)ethoxy)propylamine.
  • the product has a ⁇ max of 560 nm in water.
  • the product represented as Formula BA61 herein is prepared in a similar manner to Example 17 except 15.75 grams of N-phenyl J acid are substituted for N-acetyl H acid.
  • the product has a ⁇ max of 551 nm in methanol.
  • the product represented as Formula BA7 herein is prepared in a similar manner to Example 17 except 15.90 grams of H acid are substituted for N-acetyl H acid.
  • the product has a ⁇ max of 599 nm in methanol.
  • the bis-azo colorants set forth in Table A conform generally to Structure (II) and are prepared according to the methods described herein.
  • the Molar Absorptivity is determined by dissolving a known amount of the compound in a suitable solvent and measuring the absorbance of the solution on an ultraviolet-visible spectrophotometer. The absorptivity is calculated by dividing the absorbance by the molar concentration in moles/liter and the path length which is typically one centimeter.
  • L*, a* and b* values are measured on each fabric (four internal replicates for each wash condition) using a Hunter LabScan XE reflectance spectrophotometer with D65 illumination, 10° observer and UV filter excluded, and difference values calculated against a nil-dye HDL reference.
  • wash solution absorbance vs. ⁇ b* From the plot of wash solution absorbance vs. ⁇ b*, the wash solution absorbance necessary to deliver a ⁇ b* of ⁇ 2.0 on fabric is determined by linear interpolation of the two data points that bracket the target ⁇ b*.
  • the relative hue angle ⁇ R is then calculated as 270+arctan(
  • the absolute hue angle ⁇ A is calculated as 270+arctan(
  • the surface color of an article may be quantified using a series of measurements—L*, a*, and b*—generated by measuring the samples using a spectrophotometer.
  • the equipment used for this test is a Gretag Macbeth Color Eye 7000A spectrophotometer.
  • the software program used is “Color imatch.” “L” is a measure of the amount of white or black in a sample; higher “L” values indicate a lighter colored sample. A measure of the amount of red or green in a sample is determined by “a*” values. A measure of the amount of blue or yellow in a sample is determined by “b*” values; lower (more negative) b* values indicate more blue on a sample.
  • DE* eff (( L* c ⁇ L* s ) 2 +( a* c ⁇ a* s ) 2 +( b* c ⁇ b* s ) 1/2
  • This procedure uses three fabric types to determine the propensity of a dye dissolved in a detergent matrix to stain fabric in a manner similar to a home laundry pre-treat scenario.
  • the three primary fibers examined are cotton, nylon, and spandex (a synthetic polymer having urethane blocks) that comprise the following fabrics:
  • 16 oz cotton interlock knit fabric (270 g/square meter, brightened with Uvitex BNB fluorescent whitening agent, obtained from Test Fabrics. P.O. Box 26, Weston, Pa., 18643), 6.3 oz 90% Cotton/10% Lycra®, Stock # CLF, obtained from Dharma Trading Co., 1604 Fourth St. San Rafael, Calif. 94901, 80% Nylon/20% Spandex, Item #983684GN, obtained from Hancock Fabrics, One Fashion Way, Baldwyn, Miss. 38824.
  • a one inch diameter circle for each of the dyed detergent samples was drawn using a template and labeled with the dye identification on the test fabrics with a non-staining, acrylic ink textile marker (TEXPEN textile marker made by Mark-tex Corp., Englewood, N.J. 07631).
  • TEXPEN textile marker made by Mark-tex Corp., Englewood, N.J. 07631.
  • test fabrics were placed on top of a piece of plastic backed paper counter sheet, or alternatively, a single layer of paper towel over aluminum foil, and stained at the 16 hrs, 1 hr, and 15 min time intervals. Staining was done by placing approximately 0.5 g of the dyed detergent on the fabric allowing it to soak through the fabric with the excess being absorbed by the counter sheet so that the circular test area was saturated with detergent without spreading to adjacent test circles. Due to possible light fading of the dyes, they were placed under a covered area to prevent direct exposure to light while allowing air to pass over the fabrics. The 16 hr stains were applied in the evening while the 1 hr and 15 min swatches were stained the following morning prior to washing.
  • the approximate total amount of detergent applied is calculated by multiplying the total number of stained areas by the amount of detergent delivered for each stain. If this amount exceeds the recommended dosage for the detergent then divide the total detergent by the recommended dosage to determine the number of wash loads to distribute the stained fabrics. If the stained fabrics do not provide the total recommended amount of detergent for a load, then the balance of the detergent is filled with Tide Free (nil-dye) detergent.
  • the pretreated fabrics are washed in a full scale Kenmore top loading washer with 5.5 lbs of terry washcloths used as ballast under median North American conditions of 17 gallons of 90° F./6 grains per gallon of hardness wash water with a rinse of 60° F./6 grains per gallon of hardness water. After the wash is complete the test fabrics are dried with the ballast in a forced heated air drier at the highest temperature setting for 60 minutes, or until completely dry.
  • the circled stain areas were analyzed using a Hunter Colorquest or Labscan XE with D65 lighting, UV filter not included and a 0.5′′ port opening.
  • a nil-dye pre-treat control stain was used as the instrument reference standard for calculating the DE* because the detergent contains brightener.
  • Visual assessment is done under fluorescent lights with a white paper (92 brightness) background under the swatch.
  • the DE*/Visual Scale allows communication of stain intensity in a non-technical manner.
  • Test 1 Determination of Component Parts of Bis-Azo Colorants
  • A, B and C moieties used to construct bluing agents A—N ⁇ N—B—N ⁇ N—C.
  • the molar absorptivity ( ⁇ ) of each example is provided in Table 2.
  • Table 3 provides the deposition and hue angle for Examples 1-19. The data is sorted by variation in Components A, B and C, as determined previously.
  • absolute hue angle describes the actual hue angle of the fabric on the a*, b* plane. This is the angle that a consumer actually sees when looking at the fabric.
  • Relative hue angle is determined against a tracer fabric washed in nil-dye HDL (i.e. same detergent, but without dye), and thus gives the movement within the a*, b* plane relative to the nil-dye control.
  • the bluing agent of the present invention may have an absolute hue angle in the range of 265° to 310°, 265° to 300°, 265° to 295°, 270° to 295°, 270° to 290°, or even in the range of 273° to 287°.
  • Tables 4A and 4B provide examples of liquid detergent formulations which include at least one bluing agent of the present invention.
  • the formulations are shown in Table 4A as Formulations 1a through if and in Table 4B as Formulations 1g through 1l.
  • Liquid Detergent Formulations Comprising the Inventive Bluing Agent 1a 1b 1c 1d 1e 1f 5 Ingredient wt % wt % wt % wt % wt % sodium alkyl ether sulfate 14.4% 14.4% 9.2% 5.4% linear alkylbenzene sulfonic 4.4% 4.4% 12.2% 5.7% 1.3% 22.0% acid alkyl ethoxylate 2.2% 2.2% 8.8% 8.1% 3.4% 18.0% amine oxide 0.7% 0.7% 1.5% citric acid 2.0% 2.0% 3.4% 1.9% 1.0% 1.6% fatty acid 3.0% 3.0% 8.3% 16.0% protease 1.0% 1.0% 0.7% 1.0% 2.5% amylase 0.2% 0.2% 0.2% 0.3% lipase 0.2% borax 1.5% 1.5% 2.4% 2.9% calcium and sodium formate 0.2% 0.2% formic acid 1.1% amine ethoxylate polymers 1.8% 1.8% 2.1% 3.2% sodium polyacrylate 0.2% sodium polyacrylate 0.6% copolymer
  • Table 5 provides examples of granular detergent formulations which include at least one bluing agent of the present invention.
  • the formulations are shown in Table 5 as Formulations 2a through 2e.
  • Formulations 3a-3d Liquid Fabric Care Compositions
  • Table 6 provides examples of liquid fabric care compositions which include at least one bluing agent of the present invention.
  • the compositions are shown in Table 6 as Formulations 3a through 3d.
  • the present invention provides a bluing agent for textile and/or paper substrates comprising at least one chromophore component that comprises a bis-azo colorant and at least one polymeric component.
  • a laundry detergent composition and a rinse added fabric softener containing such a bluing agent is also contemplated herein.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US12/910,258 2010-10-22 2010-10-22 Bis-azo colorants for use as bluing agents Abandoned US20120101018A1 (en)

Priority Applications (40)

Application Number Priority Date Filing Date Title
US12/910,258 US20120101018A1 (en) 2010-10-22 2010-10-22 Bis-azo colorants for use as bluing agents
ARP110103893A AR083503A1 (es) 2010-10-22 2011-10-20 Colorantes bis-azo para usar como colorantes azules
EP11779294.5A EP2630227B1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and rapidly water-soluble brightener
CN201610101320.5A CN105695160B (zh) 2010-10-22 2011-10-21 用作上蓝剂的双偶氮着色剂
EP11781907.8A EP2630228A1 (en) 2010-10-22 2011-10-21 Low built detergent composition comprising bluing agent
MX2013004463A MX357388B (es) 2010-10-22 2011-10-21 Composicion detergente que comprende agente azulado y agente de eliminacion se suciedad arcillosa/antirredeposito.
MX2013004461A MX357340B (es) 2010-10-22 2011-10-21 Composición detergente que comprende un agente colorante azul y un abrillantador que se solubiliza, rápidamente, en agua.
EP11778757.2A EP2630225A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
PCT/US2011/057264 WO2012054821A1 (en) 2010-10-22 2011-10-21 Low built detergent composition comprising bluing agent
PCT/US2011/057279 WO2012054827A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
CN201180050989.1A CN103339245B (zh) 2010-10-22 2011-10-21 包含上蓝剂和快速水溶性增白剂的洗涤剂组合物
JP2013535118A JP5833130B2 (ja) 2010-10-22 2011-10-21 青み付け剤としての使用を目的としたビズアゾ系染料
ES11785825T ES2699751T3 (es) 2010-10-22 2011-10-21 Colorantes diazoicos para usar como agentes de azulado
BR112013009794A BR112013009794A2 (pt) 2010-10-22 2011-10-21 composição detergente que compreende agente de azulamento e agente de remoção/antirredeposição de sujeira argilosa
MX2013004460A MX357342B (es) 2010-10-22 2011-10-21 Composición detergente con bajo contenido de aditivo que comprende un agente colorante azul.
PCT/US2011/057270 WO2012054823A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
PCT/US2011/057262 WO2012054820A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and rapidly water-soluble brightener
CN201180050981.5A CN103180424B (zh) 2010-10-22 2011-10-21 包含上蓝剂和粘土污垢移除/抗再沉积剂的洗涤剂组合物
CN201180050982XA CN103201370A (zh) 2010-10-22 2011-10-21 用作上蓝剂的双偶氮着色剂
CN201180051018.9A CN103168097B (zh) 2010-10-22 2011-10-21 包含上蓝剂和粘土污垢移除/抗再沉积剂的洗涤剂组合物
BR112013009791-4A BR112013009791B1 (pt) 2010-10-22 2011-10-21 Composição para cuidado na lavagem de roupas compreendendo corantes bis-azo para uso como agentes de azulamento
BR112013009792A BR112013009792A2 (pt) 2010-10-22 2011-10-21 composição detergente que compreende agente de azulamento e alvejante rapidamente soluvel em agua
MX2013004459A MX357341B (es) 2010-10-22 2011-10-21 Colorantes bis-azoicos para usarse como agentes de azulado.
CN201180050993.8A CN103180425B (zh) 2010-10-22 2011-10-21 包含上蓝剂的低复配洗涤剂组合物
PCT/US2011/057290 WO2012054835A1 (en) 2010-10-22 2011-10-21 Bis-azo colorants for use as bluing agents
PL11785825T PL2630229T3 (pl) 2010-10-22 2011-10-21 Barwniki diazowe do stosowania jako środki nadające niebieski odcień
BR112013009793A BR112013009793A2 (pt) 2010-10-22 2011-10-21 composição detergente que compreende agente de azulamento e agente de remoçao/antirreposição de sujeira argilosa
EP11785825.8A EP2630229B1 (en) 2010-10-22 2011-10-21 Bis-azo colorants for use as bluing agents
MX2013004462A MX357338B (es) 2010-10-22 2011-10-21 Composición detergente que comprende agente de azulado y agente de eliminación de suciedad arcillosa/antirredepósito.
CA2815479A CA2815479C (en) 2010-10-22 2011-10-21 Modified bis-azo colorants for use as bluing agents
BR112013009798A BR112013009798A2 (pt) 2010-10-22 2011-10-21 composição detergente de baixo teor de builder que compreende agente de azulamento
EP11778758.0A EP2630226A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,256 US10876079B2 (en) 2010-10-22 2011-12-07 Bis-azo colorants for use as bluing agents
US13/313,283 US9701930B2 (en) 2010-10-22 2011-12-07 Low built detergent composition comprising bluing agent
US13/313,340 US9708573B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,310 US9708572B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,395 US9499775B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and rapidly water-soluble brightener
ZA2013/02890A ZA201302890B (en) 2010-10-22 2013-04-22 Bis-azo colorants for use as bluing agents
JP2014249304A JP6049679B2 (ja) 2010-10-22 2014-12-09 青み付け剤としての使用を目的としたビズアゾ系染料
US14/747,099 US20150291918A1 (en) 2010-10-22 2015-06-23 Bis-azo colorants for use as bluing agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/910,258 US20120101018A1 (en) 2010-10-22 2010-10-22 Bis-azo colorants for use as bluing agents

Related Child Applications (6)

Application Number Title Priority Date Filing Date
PCT/US2011/057270 Continuation WO2012054823A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
PCT/US2011/057264 Continuation WO2012054821A1 (en) 2010-10-22 2011-10-21 Low built detergent composition comprising bluing agent
USPCT/US2011/572290 Continuation 2011-10-21
PCT/US2011/057279 Continuation WO2012054827A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
PCT/US2011/057290 Continuation WO2012054835A1 (en) 2010-10-22 2011-10-21 Bis-azo colorants for use as bluing agents
PCT/US2011/057262 Continuation WO2012054820A1 (en) 2010-10-22 2011-10-21 Detergent composition comprising bluing agent and rapidly water-soluble brightener

Publications (1)

Publication Number Publication Date
US20120101018A1 true US20120101018A1 (en) 2012-04-26

Family

ID=44906443

Family Applications (7)

Application Number Title Priority Date Filing Date
US12/910,258 Abandoned US20120101018A1 (en) 2010-10-22 2010-10-22 Bis-azo colorants for use as bluing agents
US13/313,395 Expired - Fee Related US9499775B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and rapidly water-soluble brightener
US13/313,340 Active 2031-03-19 US9708573B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,256 Active 2031-05-11 US10876079B2 (en) 2010-10-22 2011-12-07 Bis-azo colorants for use as bluing agents
US13/313,310 Active US9708572B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,283 Active US9701930B2 (en) 2010-10-22 2011-12-07 Low built detergent composition comprising bluing agent
US14/747,099 Abandoned US20150291918A1 (en) 2010-10-22 2015-06-23 Bis-azo colorants for use as bluing agents

Family Applications After (6)

Application Number Title Priority Date Filing Date
US13/313,395 Expired - Fee Related US9499775B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and rapidly water-soluble brightener
US13/313,340 Active 2031-03-19 US9708573B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,256 Active 2031-05-11 US10876079B2 (en) 2010-10-22 2011-12-07 Bis-azo colorants for use as bluing agents
US13/313,310 Active US9708572B2 (en) 2010-10-22 2011-12-07 Detergent composition comprising bluing agent and clay soil removal / anti-redeposition agent
US13/313,283 Active US9701930B2 (en) 2010-10-22 2011-12-07 Low built detergent composition comprising bluing agent
US14/747,099 Abandoned US20150291918A1 (en) 2010-10-22 2015-06-23 Bis-azo colorants for use as bluing agents

Country Status (12)

Country Link
US (7) US20120101018A1 (zh)
EP (5) EP2630225A1 (zh)
JP (2) JP5833130B2 (zh)
CN (6) CN105695160B (zh)
AR (1) AR083503A1 (zh)
BR (5) BR112013009791B1 (zh)
CA (1) CA2815479C (zh)
ES (1) ES2699751T3 (zh)
MX (5) MX357342B (zh)
PL (1) PL2630229T3 (zh)
WO (5) WO2012054823A1 (zh)
ZA (1) ZA201302890B (zh)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130303429A1 (en) * 2012-05-09 2013-11-14 The Procter & Gamble Company Laundry detergent composition comprising a particle having hueing agent and clay
US20130303428A1 (en) * 2012-05-09 2013-11-14 Milliken & Company Laundry Detergent Composition Comprising A Particle Having Hueing Agent and Clay
US20140005706A1 (en) * 2012-06-30 2014-01-02 Mark Gelfand Carotid Body Ablation Via Directed Energy
US20150291918A1 (en) * 2010-10-22 2015-10-15 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
WO2015187757A1 (en) 2014-06-06 2015-12-10 The Procter & Gamble Company Detergent composition comprising polyalkyleneimine polymers
US9393070B2 (en) 2012-04-24 2016-07-19 Cibiem, Inc. Endovascular catheters and methods for carotid body ablation
US9398930B2 (en) 2012-06-01 2016-07-26 Cibiem, Inc. Percutaneous methods and devices for carotid body ablation
US9402677B2 (en) 2012-06-01 2016-08-02 Cibiem, Inc. Methods and devices for cryogenic carotid body ablation
US20160312158A1 (en) * 2015-04-23 2016-10-27 The Procter & Gamble Company Detergent compositions
US9719056B1 (en) * 2016-01-29 2017-08-01 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
US9951296B2 (en) 2015-03-30 2018-04-24 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9951301B2 (en) 2015-03-30 2018-04-24 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9955946B2 (en) 2014-03-12 2018-05-01 Cibiem, Inc. Carotid body ablation with a transvenous ultrasound imaging and ablation catheter
US9957470B2 (en) 2015-03-30 2018-05-01 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9957466B2 (en) 2015-03-30 2018-05-01 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US10053654B2 (en) 2015-04-02 2018-08-21 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
WO2019075143A1 (en) * 2017-10-12 2019-04-18 The Procter & Gamble Company LEUCO-COLORANTS AS AZURING AGENTS IN LAUNDRY CARE COMPOSITIONS

Families Citing this family (207)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140014137A1 (en) * 2009-09-18 2014-01-16 Ecolab Usa Inc. Treatment of non-trans fats with acidic tetra sodium l-glutamic acid, n, n-diacetic acid (glda)
TR201802775T4 (tr) 2010-03-01 2018-03-21 Procter & Gamble Sübstitüe edilmiş selülozik polimer ve amilaz içeren bileşim.
AU2011317223A1 (en) * 2010-10-19 2013-05-23 Novabay Pharmaceuticals, Inc. Antimicrobial polyether and polyol compounds
EP2540824A1 (en) 2011-06-30 2013-01-02 The Procter & Gamble Company Cleaning compositions comprising amylase variants reference to a sequence listing
EP2551335A1 (en) 2011-07-25 2013-01-30 The Procter & Gamble Company Enzyme stabilized liquid detergent composition
MX342855B (es) 2011-08-15 2016-10-13 Procter & Gamble Composiciones detergentes que contienen compuestos de piridinol-n-oxido.
US20130072416A1 (en) 2011-09-20 2013-03-21 The Procter & Gamble Company High suds detergent compositions comprising isoprenoid-based surfactants
AR088758A1 (es) 2011-09-20 2014-07-02 Procter & Gamble Composiciones detergentes de facil enjuague que comprenden surfactantes basados en isoprenoides
AR090031A1 (es) 2011-09-20 2014-10-15 Procter & Gamble Composiciones detergentes que comprenden sistemas tensioactivos sostenibles que comprenden tensioactivos derivados de isoprenoide
CA2849269A1 (en) 2011-09-20 2013-03-28 The Procter & Gamble Company Detergent compositions comprising specific blend ratios of isoprenoid-based surfactants
AR088442A1 (es) 2011-09-20 2014-06-11 Procter & Gamble Composiciones detergentes que comprenden sistemas surfactantes primarios que comprenden surfactantes con base en isoprenoides altamente ramificados y otros surfactantes
WO2013142486A1 (en) 2012-03-19 2013-09-26 The Procter & Gamble Company Laundry care compositions containing dyes
MX2014015035A (es) * 2012-06-08 2015-11-16 Amcol International Corp Particulas esteticas visualmente contrastantes que aumentan la solubilidad en agua, en particular utiles para la combinacion con composiciones pulverizadas o granuladas.
CN104508103A (zh) 2012-07-26 2015-04-08 宝洁公司 含酶的低ph液体清洁组合物
US10253281B2 (en) 2012-08-20 2019-04-09 Ecolab Usa Inc. Method of washing textile articles
EP2890773B1 (en) 2012-08-31 2020-04-08 The Procter and Gamble Company Laundry detergents and cleaning compositions comprising carboxyl group-containing polymers
MX2015002070A (es) 2012-08-31 2015-05-11 Procter & Gamble Detergentes de lavanderia y composiciones limpiadoras que comprenden polimeros que contienen grupos carboxilo.
CN104540932B (zh) * 2012-08-31 2017-11-17 株式会社日本触媒 含有羧基的聚合物及含有该聚合物的组合物
EP2712915A1 (en) 2012-10-01 2014-04-02 The Procter and Gamble Company Methods of treating a surface and compositions for use therein
US9095787B2 (en) 2012-10-24 2015-08-04 The Procter & Gamble Company Compositions comprising anti-foams
EP2911761A1 (en) 2012-10-24 2015-09-02 The Procter & Gamble Company Anti foam compositions comprising partly phenyl bearing polyorganosilicons
JP2016507427A (ja) 2012-12-06 2016-03-10 ザ プロクター アンド ギャンブルカンパニー 色調染料を含む可溶性パウチ
EP2740785A1 (en) 2012-12-06 2014-06-11 The Procter and Gamble Company Use of composition to reduce weeping and migration through a water soluble film
US10184097B2 (en) * 2013-02-08 2019-01-22 Ecolab Usa Inc. Protective coatings for detersive agents and methods of forming and detecting the same
ES2834373T3 (es) 2013-02-19 2021-06-17 Procter & Gamble Método para lavado de un tejido
EP2767579B1 (en) 2013-02-19 2018-07-18 The Procter and Gamble Company Method of laundering a fabric
EP2767582A1 (en) 2013-02-19 2014-08-20 The Procter and Gamble Company Method of laundering a fabric
CN105073966B (zh) 2013-03-28 2018-03-23 宝洁公司 包含聚醚胺的清洁组合物
US11118031B2 (en) 2013-04-12 2021-09-14 The Procter & Gamble Company Fibrous structures comprising polysaccharide filaments
CA2909450C (en) 2013-04-12 2019-05-21 The Procter & Gamble Company Fibrous structures exhibiting improved whiteness index values
WO2014168776A1 (en) 2013-04-12 2014-10-16 The Procter & Gamble Company Hydroxyl polymer fiber structures comprising ammonium alkylsulfonate salts and methods for making same
EP3699256A1 (en) 2013-05-28 2020-08-26 The Procter & Gamble Company Surface treatment compositions comprising photochromic dyes
US9487738B2 (en) * 2013-10-09 2016-11-08 Ecolab Usa Inc. Solidification matrix comprising a carboxylic acid terpolymer
EP2862920A1 (en) * 2013-10-17 2015-04-22 The Procter and Gamble Company Laundry treatment composition comprising a shading dye and chelant
EP2862919A1 (en) * 2013-10-17 2015-04-22 The Procter and Gamble Company Composition comprising shading dye
EP2862921A1 (en) * 2013-10-17 2015-04-22 The Procter and Gamble Company Liquid laundry composition comprising an alkoxylated polymer and a shading dye
WO2015112341A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Fabric treatment composition
EP2899260A1 (en) 2014-01-22 2015-07-29 Unilever PLC Process to manufacture a liquid detergent formulation
WO2015112340A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Method of treating textile fabrics
WO2015112338A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Method of treating textile fabrics
EP3097173B1 (en) 2014-01-22 2020-12-23 The Procter and Gamble Company Fabric treatment composition
US9556406B2 (en) 2014-02-19 2017-01-31 Milliken & Company Compositions comprising benefit agent and aprotic solvent
EP3107989A1 (en) 2014-02-19 2016-12-28 The Procter & Gamble Company Composition comprising benefit agent and aprotic solvent
WO2015130653A1 (en) 2014-02-25 2015-09-03 The Procter & Gamble Company A process for making renewable surfactant intermediates and surfactants from fats and oils and products thereof
US9994497B2 (en) 2014-02-25 2018-06-12 The Procter & Gamble Company Process for making renewable surfactant intermediates and surfactants from fats and oils and products thereof
EP2924102A1 (en) * 2014-03-24 2015-09-30 The Procter and Gamble Company Laundry unit dose article
US9719052B2 (en) 2014-03-27 2017-08-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US20150275143A1 (en) 2014-03-27 2015-10-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
WO2015171592A1 (en) 2014-05-06 2015-11-12 Milliken & Company Laundry care compositions
EP3143113A4 (en) * 2014-05-12 2018-05-02 The Procter and Gamble Company Method of laundering fabric
WO2016023145A1 (en) * 2014-08-11 2016-02-18 The Procter & Gamble Company Laundry detergent
EP2987848A1 (en) 2014-08-19 2016-02-24 The Procter & Gamble Company Method of laundering a fabric
EP2987849A1 (en) 2014-08-19 2016-02-24 The Procter and Gamble Company Method of Laundering a Fabric
JP6400837B2 (ja) 2014-08-27 2018-10-03 ザ プロクター アンド ギャンブル カンパニー 布地の処理方法
US9809782B2 (en) 2014-08-27 2017-11-07 The Procter & Gamble Company Detergent composition comprising a cationic polymer and anionic/nonionic surfactant mixture
JP6479959B2 (ja) 2014-08-27 2019-03-06 ザ プロクター アンド ギャンブル カンパニー カチオン性ポリマーを含む洗剤組成物
CA2956081C (en) 2014-08-27 2021-03-16 The Procter & Gamble Company Detergent composition comprising a cationic polymer
US9617502B2 (en) 2014-09-15 2017-04-11 The Procter & Gamble Company Detergent compositions containing salts of polyetheramines and polymeric acid
US20160090552A1 (en) 2014-09-25 2016-03-31 The Procter & Gamble Company Detergent compositions containing a polyetheramine and an anionic soil release polymer
EP3197992B1 (en) 2014-09-25 2023-06-28 The Procter & Gamble Company Fabric care compositions containing a polyetheramine
EP3197988B1 (en) 2014-09-25 2018-08-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
JP6571171B2 (ja) * 2014-09-25 2019-09-04 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ スルホン酸基含有ポリマーを含む洗濯洗剤及び洗浄組成物
US9388368B2 (en) 2014-09-26 2016-07-12 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
EP3256563A1 (en) 2014-11-17 2017-12-20 The Procter and Gamble Company Benefit agent delivery compositions
US10052398B2 (en) 2014-12-08 2018-08-21 Kinnos Inc. Additive compositions for pigmented disinfection and methods thereof
KR102457934B1 (ko) * 2015-01-16 2022-10-24 로디아 오퍼레이션스 직물의 그레이화 감소 방법
US9670438B2 (en) 2015-01-29 2017-06-06 Ecolab Usa Inc. Composition and method for the treatment of sunscreen stains in textiles
EP3075826B1 (en) 2015-03-30 2018-01-31 The Procter and Gamble Company Solid free-flowing particulate laundry detergent composition
WO2016160870A1 (en) 2015-03-30 2016-10-06 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
EP3075823A1 (en) 2015-03-30 2016-10-05 The Procter and Gamble Company A spray-dried laundry detergent base particle
WO2016160869A1 (en) 2015-03-30 2016-10-06 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
WO2016160868A1 (en) 2015-03-30 2016-10-06 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US20160289612A1 (en) 2015-04-02 2016-10-06 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US20160289610A1 (en) 2015-04-02 2016-10-06 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
WO2016176296A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of laundering a fabric
CN112143591A (zh) 2015-04-29 2020-12-29 宝洁公司 处理织物的方法
WO2016176280A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of treating a fabric
EP3088506B1 (en) 2015-04-29 2018-05-23 The Procter and Gamble Company Detergent composition
DK3088503T3 (en) 2015-04-29 2018-08-20 Procter & Gamble PROCEDURE FOR TREATING A TEXTILE SUBSTANCE
CN111718806B (zh) 2015-05-04 2022-01-04 美利肯公司 在洗衣护理组合物中作为上蓝剂的隐色三苯甲烷着色剂
EP3303535B1 (en) 2015-05-27 2018-10-03 Unilever PLC Laundry detergent composition
TR201906836T4 (tr) 2015-06-02 2019-05-21 Unilever Nv Çamaşır deterjan bileşimi.
EP3101104B1 (en) * 2015-06-05 2019-04-24 The Procter and Gamble Company Compacted liquid laundry detergent composition
JP6878314B2 (ja) 2015-06-11 2021-05-26 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 表面に組成物を塗布するための装置及び方法
EP3356504B1 (en) 2015-10-01 2019-08-14 Unilever PLC Powder laundry detergent composition
JP6585290B2 (ja) 2015-10-06 2019-10-02 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 可溶性単位用量洗剤パウチを含む可撓性ボックスバッグ
EP3153425B1 (en) 2015-10-06 2018-07-04 The Procter and Gamble Company Flexible box bag comprising detergent powder and a scoop
CN108291180A (zh) 2015-11-26 2018-07-17 宝洁公司 包含蛋白酶和经包封的脂肪酶的液体洗涤剂组合物
US20170218202A1 (en) * 2016-01-29 2017-08-03 Milliken & Company Bis-Azo Colorants For Use As Bluing Agents
CA3011889A1 (en) 2016-02-12 2017-08-17 Kinnos Inc. Colored compositions and methods for use in surface decontamination
CN108603140B (zh) * 2016-02-17 2020-09-08 荷兰联合利华有限公司 增白组合物
EP3417039B1 (en) * 2016-02-17 2019-07-10 Unilever PLC Whitening composition
CN108699490B (zh) * 2016-02-17 2020-06-02 荷兰联合利华有限公司 增白组合物
ES2721224T3 (es) 2016-05-09 2019-07-29 Procter & Gamble Composición detergente que comprende una enzima transformadora de ácido oleico
PL3540036T3 (pl) 2016-05-09 2021-04-19 The Procter & Gamble Company Kompozycja detergentowa zawierająca lipoksygenazę kwasu tłuszczowego
ES2835648T3 (es) 2016-05-09 2021-06-22 Procter & Gamble Composición detergente que comprende una descarboxilasa de ácidos grasos
WO2017198438A1 (en) 2016-05-17 2017-11-23 Unilever Plc Liquid laundry detergent compositions
WO2017198574A1 (en) 2016-05-17 2017-11-23 Unilever Plc Liquid laundry detergent compositions
US10494592B2 (en) * 2016-05-20 2019-12-03 The Procter & Gamble Company Detergent composition comprising anionic/nonionic/cationic surfactant system and encapsulates
US10457900B2 (en) * 2016-05-20 2019-10-29 The Proctor & Gamble Company Detergent composition comprising an alkyl ether sulfate-rich surfactant system and coated encapsulates
CN106349752A (zh) * 2016-08-25 2017-01-25 山西青山化工有限公司 一种均二苯乙烯双三嗪型液体增白剂及其制备方法
BR112019006017A2 (pt) 2016-09-27 2019-06-18 Unilever Nv método de lavagem de roupa
RU2709518C1 (ru) * 2016-10-03 2019-12-18 Дзе Проктер Энд Гэмбл Компани Композиция моющего средства для стирки с низким показателем ph
EP3301153B1 (en) 2016-10-03 2019-09-11 The Procter & Gamble Company Process for preparing a spray-dried laundry detergent particle
US20180094221A1 (en) 2016-10-03 2018-04-05 The Procter & Gamble Company Laundry detergent composition
MX2019003848A (es) 2016-10-03 2019-06-24 Procter & Gamble Composición detergente para lavandería.
ES2757944T3 (es) * 2016-10-03 2020-04-30 Procter & Gamble Composición detergente para lavado de ropa
CN109790490A (zh) * 2016-10-03 2019-05-21 宝洁公司 衣物洗涤剂组合物
EP3301164A1 (en) * 2016-10-03 2018-04-04 The Procter & Gamble Company Low ph laundry detergent composition
PL3301157T3 (pl) 2016-10-03 2020-09-07 The Procter & Gamble Company Kompozycja detergentu piorącego o niskim ph
MX2019003845A (es) * 2016-10-03 2019-06-24 Procter & Gamble Composición detergente para lavandería con un ph bajo.
WO2018072979A1 (en) 2016-10-18 2018-04-26 Unilever Plc Whitening composition
EP3535368A1 (en) * 2016-11-01 2019-09-11 The Procter & Gamble Company Leuco colorants as bluing agents in laundry care compositions
JP6790257B2 (ja) * 2016-11-01 2020-11-25 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 洗濯ケア組成物における青味剤としてのロイコ着色剤、その包装、キット及び方法
US10851329B2 (en) * 2016-11-01 2020-12-01 Milliken & Company Leuco colorants as bluing agents in laundry care compositions
US20180119056A1 (en) 2016-11-03 2018-05-03 Milliken & Company Leuco Triphenylmethane Colorants As Bluing Agents in Laundry Care Compositions
EP3339416A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339413A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339419A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339415A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339420A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339414A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339418A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
EP3339407A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
WO2018118825A1 (en) 2016-12-22 2018-06-28 The Procter & Gamble Company Laundry detergent composition
EP3339417A1 (en) 2016-12-22 2018-06-27 The Procter & Gamble Company Laundry detergent composition
MX2019009275A (es) * 2017-02-06 2019-12-11 Procter & Gamble Hoja de detergente para ropa con patrones gráficos impresos.
EP3649221B8 (en) 2017-07-07 2024-05-29 Unilever IP Holdings B.V. Laundry cleaning composition
WO2019008036A1 (en) 2017-07-07 2019-01-10 Unilever Plc WHITENING COMPOSITION
BR112020010648A2 (pt) 2017-11-30 2021-02-02 Unilever N.V. composição detergente, composição detergente de lavanderia, método para aprimorar limpeza enzimática em água e uso de uma enzima protease
EP3546557B1 (en) 2018-03-28 2020-10-07 The Procter & Gamble Company Catalase inhibition during a laundering process
EP3546554A1 (en) 2018-03-28 2019-10-02 The Procter & Gamble Company Spray-drying process
EP3546559A1 (en) 2018-03-28 2019-10-02 The Procter & Gamble Company Laundry detergent composition
WO2019191171A1 (en) 2018-03-28 2019-10-03 The Procter & Gamble Company Laundry detergent composition
EP3546558A1 (en) 2018-03-28 2019-10-02 The Procter & Gamble Company Laundry detergent composition
CN111742040B (zh) 2018-03-28 2021-10-29 宝洁公司 用于制备喷雾干燥的衣物洗涤剂颗粒的方法
WO2019191173A1 (en) 2018-03-28 2019-10-03 The Procter & Gamble Company Process for preparing a spray-dried laundry detergent particle
CN111971372B (zh) 2018-04-03 2022-03-11 联合利华知识产权控股有限公司 染料颗粒
WO2019219531A1 (en) 2018-05-17 2019-11-21 Unilever Plc Cleaning composition
EP3775122A1 (en) 2018-05-17 2021-02-17 Unilever PLC Cleaning composition comprising rhamnolipid and alkyl ether carboxylate surfactants
CA3207880A1 (en) 2018-06-20 2019-12-26 The Procter & Gamble Company A fabric care or home care product comprising polysaccharide derivatives
EP3594319B1 (en) 2018-07-12 2021-05-05 The Procter & Gamble Company A solid free-flowing particulate laundry detergent composition
BR112021000774A2 (pt) 2018-07-17 2021-04-13 Unilever Ip Holdings B.V. Uso de ramnolipídio em um sistema de tensoativo para detergentes para lavagem manual
CN112543801A (zh) 2018-07-27 2021-03-23 荷兰联合利华有限公司 洗衣洗涤剂
BR112021004507A2 (pt) 2018-09-17 2021-06-08 Unilever Ip Holdings B.V. composição detergente, método de tratamento de um substrato com uma composição detergente e uso de uma enzima lipase bacteriana
BR112021009828A2 (pt) 2018-11-20 2021-08-17 Unilever Ip Holdings B.V. composição detergente líquida, método de tratamento de um substrato de tecido e uso de uma enzima esterol esterase
CN113015781B (zh) 2018-11-20 2022-09-13 联合利华知识产权控股有限公司 洗涤剂组合物
CN113166689A (zh) 2018-11-20 2021-07-23 联合利华知识产权控股有限公司 洗涤剂组合物
CN113056549B (zh) 2018-11-20 2023-03-10 联合利华知识产权控股有限公司 洗涤剂组合物
BR112021009789A2 (pt) 2018-11-20 2021-08-17 Unilever Ip Holdings B.V. composição detergente, método de tratamento de um substrato de tecido e uso de uma enzima esterase
WO2020109227A1 (en) 2018-11-28 2020-06-04 Unilever N.V. Large particles
US20220098520A1 (en) 2019-01-22 2022-03-31 Conopco, Inc., D/B/A Unilever Laundry detergent
CN109881500B (zh) * 2019-03-05 2020-06-19 游晟纺织科技(深圳)有限公司 一种不含荧光增白剂的纺织面料及其制备方法
CN113728083A (zh) 2019-04-29 2021-11-30 宝洁公司 用于制备衣物洗涤剂组合物的方法
EP3750979A1 (en) 2019-06-12 2020-12-16 Unilever N.V. Use of laundry detergent composition
EP3750978A1 (en) 2019-06-12 2020-12-16 Unilever N.V. Laundry detergent composition
EP3754010A1 (en) 2019-06-17 2020-12-23 The Procter & Gamble Company A solid free-flowing particulate laundry detergent composition comprises a detersive surfactant and a linear polyamine salt
US20220372397A1 (en) 2019-06-28 2022-11-24 Conopco, Inc., D/B/A Unilever Detergent composition
CN113891930A (zh) 2019-06-28 2022-01-04 联合利华知识产权控股有限公司 洗涤剂组合物
CN113906124B (zh) 2019-06-28 2024-08-02 联合利华知识产权控股有限公司 洗涤剂组合物
EP3990604B1 (en) 2019-06-28 2022-12-14 Unilever Global IP Limited Detergent composition
WO2020260006A1 (en) 2019-06-28 2020-12-30 Unilever Plc Detergent compositions
EP3990603B1 (en) 2019-06-28 2022-12-07 Unilever Global Ip Limited Detergent composition
BR112022003050A2 (pt) 2019-09-02 2022-05-17 Unilever Ip Holdings B V Composição detergente de lavagem de roupas aquosa e método doméstico para tratar um tecido
EP3798290B1 (en) 2019-09-30 2022-08-17 The Procter & Gamble Company Use of an anionically-modified cellulosic polymer as a dye transfer inhibitor during a textile laundering process
AR120142A1 (es) 2019-10-07 2022-02-02 Unilever Nv Composición detergente
WO2021185956A1 (en) 2020-03-19 2021-09-23 Unilever Ip Holdings B.V. Detergent composition
EP4121502A1 (en) 2020-03-19 2023-01-25 Unilever IP Holdings B.V. Detergent composition
BR112022024537A2 (pt) 2020-06-08 2022-12-27 Unilever Ip Holdings B V Método de aprimoramento da atividade de protease em uma composição detergente e uso de saponina
ES2947859T3 (es) 2020-07-06 2023-08-23 Procter & Gamble Un proceso para fabricar una composición detergente para lavado de ropa en forma de partículas
WO2022023250A1 (en) 2020-07-27 2022-02-03 Unilever Ip Holdings B.V. Use of an enzyme and surfactant for inhibiting microorganisms
CN111849201A (zh) * 2020-07-30 2020-10-30 江苏华彩化学科技有限公司 一种大分子染料及其在超浓缩型高效抑菌洗衣凝珠中的应用
US20230287300A1 (en) 2020-08-28 2023-09-14 Conopco, Inc., D/B/A Unilever Surfactant and detergent composition
WO2022042977A1 (en) 2020-08-28 2022-03-03 Unilever Ip Holdings B.V. Detergent composition
EP4204526B1 (en) 2020-08-28 2024-04-24 Unilever IP Holdings B.V. Surfactant and detergent composition
CN116018396A (zh) 2020-08-28 2023-04-25 联合利华知识产权控股有限公司 洗涤剂组合物
WO2022043042A1 (en) 2020-08-28 2022-03-03 Unilever Ip Holdings B.V. Detergent composition
WO2022077022A1 (en) 2020-10-09 2022-04-14 The Procter & Gamble Company Packaged laundry detergent product
CN116583583A (zh) 2020-12-17 2023-08-11 联合利华知识产权控股有限公司 用途和清洁组合物
US20240002751A1 (en) 2020-12-17 2024-01-04 Conopco, Inc., D/B/A Unilever Cleaning composition
WO2022268657A1 (en) 2021-06-24 2022-12-29 Unilever Ip Holdings B.V. Unit dose cleaning composition
EP4108754A1 (en) 2021-06-25 2022-12-28 The Procter & Gamble Company A process for making a packaged laundry detergent powder
EP4108756A1 (en) 2021-06-25 2022-12-28 The Procter & Gamble Company A laundry detergent powder
EP4112707A1 (en) 2021-06-30 2023-01-04 The Procter & Gamble Company Fabric treatment
EP4123005B1 (en) 2021-07-19 2024-03-06 The Procter & Gamble Company Cleaning composition comprising bacterial spores
CA3228918A1 (en) 2021-08-10 2023-02-16 Nippon Shokubai Co., Ltd. Polyalkylene-oxide-containing compound
EP4399269A1 (en) 2021-09-09 2024-07-17 Milliken & Company Phenolic compositions for malodor reduction
WO2023041694A1 (en) 2021-09-20 2023-03-23 Unilever Ip Holdings B.V. Detergent composition
WO2023067075A1 (en) 2021-10-21 2023-04-27 Unilever Ip Holdings B.V. Detergent compositions
EP4212608A1 (en) 2022-01-14 2023-07-19 The Procter & Gamble Company A method of making a spray-dried laundry detergent particle
WO2023144071A1 (en) 2022-01-28 2023-08-03 Unilever Ip Holdings B.V. Laundry composition
WO2023150903A1 (en) 2022-02-08 2023-08-17 The Procter & Gamble Company A method of laundering fabric
CN118489000A (zh) 2022-02-08 2024-08-13 宝洁公司 洗涤织物的方法
EP4234666A1 (en) 2022-02-24 2023-08-30 The Procter & Gamble Company Water-soluble unit dose article comprising a fibrous non-woven sheet and a surfactant system
EP4234672A1 (en) 2022-02-24 2023-08-30 The Procter & Gamble Company Water-soluble unit dose article comprising a fibrous non-woven sheet and a hueing dye particle
EP4279570A1 (en) 2022-05-19 2023-11-22 The Procter & Gamble Company A process for making a particulate laundry detergent composition
EP4299703A1 (en) 2022-06-27 2024-01-03 The Procter & Gamble Company A solid free-flowing particulate laundry detergent composition
EP4299701A1 (en) 2022-06-27 2024-01-03 The Procter & Gamble Company A solid free-flowing particulate laundry detergent composition
EP4299702A1 (en) 2022-06-27 2024-01-03 The Procter & Gamble Company A solid free-flowing particulate laundry detergent composition
EP4299704A1 (en) 2022-06-27 2024-01-03 The Procter & Gamble Company A method of laundering and drying fabric
EP4342969A1 (en) 2022-09-21 2024-03-27 The Procter & Gamble Company A solid detergent cleaning composition
EP4342970A1 (en) 2022-09-21 2024-03-27 Milliken & Company Coloured fabric hueing dye agent particles
EP4364930A1 (en) 2022-11-01 2024-05-08 The Procter & Gamble Company Sealing jaws and water-soluble unit dose article comprising a fibrous non-woven sheet
EP4364929A1 (en) 2022-11-01 2024-05-08 The Procter & Gamble Company Sealing jaws and water-soluble unit dose article comprising a fibrous non-woven sheet
EP4382592A1 (en) 2022-12-06 2024-06-12 The Procter & Gamble Company Water-soluble unit dose article comprising a fibrous non-woven sheet and a surfactant system
EP4389867A1 (en) 2022-12-23 2024-06-26 The Procter & Gamble Company A process of making a laundry detergent article
EP4389866A1 (en) 2022-12-23 2024-06-26 The Procter & Gamble Company A process of making a water-soluble detergent unit dose article

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725384A (en) * 1969-04-17 1973-04-03 Ciba Geigy Ag Substituted phenyl-azo-phenyl-azo-phenyl compounds
US3762859A (en) * 1971-03-15 1973-10-02 Colgate Palmolive Co Enhancing the apparent whiteness of fabrics by applying an effective amount of an alkali and heat stable water soluble disazo blue dyestuff fabric softening and detergent composition therefor
WO2005040286A1 (en) * 2003-10-27 2005-05-06 Clariant International Ltd Storagestable concentrated aqueous solutions of anionic dis- or tetrazo dyestuffs
WO2010024468A1 (en) * 2008-09-01 2010-03-04 The Procter & Gamble Company Sulfonate group-containing copolymers and manufacturing method thereof

Family Cites Families (100)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2220099A (en) 1934-01-10 1940-11-05 Gen Aniline & Flim Corp Sulphonic acids
US2477383A (en) 1946-12-26 1949-07-26 California Research Corp Sulfonated detergent and its method of preparation
CH426059A (de) 1960-02-15 1966-12-15 Sandoz Ag Verfahren zur Herstellung von Disazoverbindungen
DE1153476B (de) 1960-02-15 1963-08-29 Sandoz Ag Verfahren zur Herstellung von Disazofarbstoffen
US3929678A (en) 1974-08-01 1975-12-30 Procter & Gamble Detergent composition having enhanced particulate soil removal performance
US4228042A (en) 1978-06-26 1980-10-14 The Procter & Gamble Company Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group
US4260529A (en) 1978-06-26 1981-04-07 The Procter & Gamble Company Detergent composition consisting essentially of biodegradable nonionic surfactant and cationic surfactant containing ester or amide
GB2036779B (en) 1978-11-22 1983-03-09 Bayer Ag Polyether disazo dyestuffs
US4239660A (en) 1978-12-13 1980-12-16 The Procter & Gamble Company Detergent composition comprising a hydrolyzable cationic surfactant and specific alkalinity source
DE2948456A1 (de) * 1979-12-01 1981-06-11 Basf Ag, 6700 Ludwigshafen Disazofarbstoffe
DE3049454A1 (de) * 1980-12-30 1982-07-29 Bayer Ag, 5090 Leverkusen Fluessigkristallines material enthaltend disazofarbstoffe
US4400320A (en) 1981-07-13 1983-08-23 Milliken Research Corporation Alkyleneoxy fugitive tints containing a 2-amino, 6-methoxy benzathiazole group and process for preparing such fugitive tints
JPS5813789A (ja) * 1981-07-20 1983-01-26 三菱化学株式会社 ジスアゾ化合物及びセルロース含有繊維類用ジスアゾ染料
GB2105738B (en) * 1981-07-20 1985-05-22 Mitsubishi Chem Ind Reactive disazo dyes
US4565647B1 (en) 1982-04-26 1994-04-05 Procter & Gamble Foaming surfactant compositions
US4483780A (en) 1982-04-26 1984-11-20 The Procter & Gamble Company Detergent compositions containing polyglycoside and polyethoxylate detergent surfactants
US4483779A (en) 1982-04-26 1984-11-20 The Procter & Gamble Company Detergent compositions comprising polyglycoside and polyethoxylate surfactants and anionic fluorescer
JPS5975952A (ja) * 1982-10-25 1984-04-28 Mitsubishi Chem Ind Ltd ジスアゾ化合物及び反応型ジスアゾ染料
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
JPS61151269A (ja) * 1984-12-25 1986-07-09 Mitsubishi Chem Ind Ltd ジスアゾ染料
AU636173B2 (en) 1989-10-30 1993-04-22 Lenzing Aktiengesellschaft Method for the chlorine-free bleaching of pulps
US5332806A (en) * 1990-05-18 1994-07-26 Ciba-Geigy Corporation Disazo dyes which contain 2-hydroxynaphthyl moiety
CA2092558C (en) 1990-09-28 1997-08-19 Bruce Prentiss Murch Detergent containing alkyl sulfate and polyhydroxy fatty acid amide surfactants
HUT64784A (en) 1990-09-28 1994-02-28 Procter & Gamble Detergent preparatives containijng n-(polyhydroxi-alkyl)-fatty acid amides and cleaning agents
EP0631608B1 (en) 1992-03-16 1996-07-17 The Procter & Gamble Company Fluid compositions containing polyhydroxy fatty acid amides
US5188769A (en) 1992-03-26 1993-02-23 The Procter & Gamble Company Process for reducing the levels of fatty acid contaminants in polyhydroxy fatty acid amide surfactants
GB9217358D0 (en) 1992-08-14 1992-09-30 Ici Plc Chemical compounds
EP0592754A1 (en) 1992-10-13 1994-04-20 The Procter & Gamble Company Fluid compositions containing polyhydroxy fatty acid amides
US5360568A (en) 1993-11-12 1994-11-01 Lever Brothers Company, Division Of Conopco, Inc. Imine quaternary salts as bleach catalysts
US5370826A (en) 1993-11-12 1994-12-06 Lever Brothers Company, Division Of Conopco, Inc. Quaternay oxaziridinium salts as bleaching compounds
EP0728183B1 (en) 1993-11-12 1998-03-25 Unilever N.V. Activation of bleach precursors with imine quaternary salts
US5360569A (en) 1993-11-12 1994-11-01 Lever Brothers Company, Division Of Conopco, Inc. Activation of bleach precursors with catalytic imine quaternary salts
WO1995013352A1 (en) 1993-11-12 1995-05-18 Unilever N.V. Imine quaternary salts as bleach catalysts
BR9507260A (pt) * 1994-03-31 1997-09-30 Unilever Nv Composição detergente para lavagem de tecido
US5718614A (en) 1995-08-28 1998-02-17 Electro-Matic Products Company Control apparatus for grinder
US5576282A (en) 1995-09-11 1996-11-19 The Procter & Gamble Company Color-safe bleach boosters, compositions and laundry methods employing same
US6022844A (en) 1996-03-05 2000-02-08 The Procter & Gamble Company Cationic detergent compounds
US5759990A (en) 1996-10-21 1998-06-02 The Procter & Gamble Company Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor
EG22088A (en) 1996-04-16 2002-07-31 Procter & Gamble Alkoxylated sulfates
EG21623A (en) 1996-04-16 2001-12-31 Procter & Gamble Mid-chain branced surfactants
PH11997056158B1 (en) 1996-04-16 2001-10-15 Procter & Gamble Mid-chain branched primary alkyl sulphates as surfactants
MA24137A1 (fr) 1996-04-16 1997-12-31 Procter & Gamble Fabrication d'agents de surface ramifies .
NZ332657A (en) 1996-05-03 2000-10-27 Procter & Gamble Laundry detergent compositions comprising cationic surfactants and modified polyamine soil dispersents
MA25183A1 (fr) 1996-05-17 2001-07-02 Arthur Jacques Kami Christiaan Compositions detergentes
US5700386A (en) 1996-08-08 1997-12-23 The Procter & Gamble Company Process for making soil release polymer granules
CA2268772C (en) 1996-10-18 2008-12-09 The Procter & Gamble Company Detergent compositions comprising an amylolytic enzyme and a cationic surfactant
US6150322A (en) 1998-08-12 2000-11-21 Shell Oil Company Highly branched primary alcohol compositions and biodegradable detergents made therefrom
US6093856A (en) 1996-11-26 2000-07-25 The Procter & Gamble Company Polyoxyalkylene surfactants
DK0958342T3 (da) 1996-12-31 2003-10-27 Procter & Gamble Fortykkede stærkt vandige væskeformige detergentsammensætninger
WO1998035006A1 (en) 1997-02-11 1998-08-13 The Procter & Gamble Company Liquid cleaning composition
GB2321900A (en) 1997-02-11 1998-08-12 Procter & Gamble Cationic surfactants
WO1998035005A1 (en) 1997-02-11 1998-08-13 The Procter & Gamble Company A cleaning composition
WO1998035002A1 (en) 1997-02-11 1998-08-13 The Procter & Gamble Company Cleaning compositions
AR011666A1 (es) 1997-02-11 2000-08-30 Procter & Gamble Composicion o componente solido, detergente que comprende surfactante/s cationicos y su uso para mejorar la distribucion y/o dispersion en agua.
MA24733A1 (fr) 1997-03-07 1999-10-01 Procter & Gamble Compositions de blanchiment contenant un catalyseur metallique de blanchiment et activateurs de blanchiment et/ou acides percarboxyliques organiques
DE69801547T2 (de) 1997-06-11 2002-04-18 Kuraray Co., Ltd Wasserlöslicher Folie
BR9810780A (pt) 1997-07-21 2001-09-18 Procter & Gamble Produtos de limpeza compreendendo tensoativos de alquilarilssulfonato aperfeiçoados, preparados através de olefinas de vinilideno e processos para preparação dos mesmos
ZA986445B (en) 1997-07-21 1999-01-21 Procter & Gamble Processes for making alkylbenzenesulfonate surfactants from alcohols and products thereof
KR100336937B1 (ko) 1997-07-21 2002-05-25 데이비드 엠 모이어 결정성파괴된계면활성제의혼합물을함유하는세제조성물
ES2193540T3 (es) 1997-07-21 2003-11-01 Procter & Gamble Procedimiento mejorados para preparar tensioactivos de aquilbencenosulfonato y productos que contienen dichos tensioactivos.
PH11998001775B1 (en) 1997-07-21 2004-02-11 Procter & Gamble Improved alkyl aryl sulfonate surfactants
CA2297170C (en) 1997-07-21 2003-04-01 The Procter & Gamble Company Improved alkylbenzenesulfonate surfactants
US6482994B2 (en) 1997-08-02 2002-11-19 The Procter & Gamble Company Ether-capped poly(oxyalkylated) alcohol surfactants
KR100447695B1 (ko) 1997-08-08 2004-09-08 더 프록터 앤드 갬블 캄파니 개질된 알킬아릴의 제조방법
US6031023A (en) 1997-12-03 2000-02-29 Milliken & Company Dry erase ink composition
ES2260941T3 (es) 1998-10-20 2006-11-01 THE PROCTER & GAMBLE COMPANY Detergentes para la ropa que comprenden alquilbenceno sulfonatos modificados.
ID28751A (id) 1998-10-20 2001-06-28 Procter & Gamble Detergen pencuci yang mengandung alkilbenzena sulfonat termodifikasi
DE19904513A1 (de) 1999-02-04 2000-08-10 Cognis Deutschland Gmbh Detergensgemische
EP1151077A1 (en) 1999-02-10 2001-11-07 The Procter & Gamble Company Low density particulate solids useful in laundry detergents
CA2325620C (en) * 1999-11-15 2004-05-11 The Procter & Gamble Company Bleach-containing non-aqueous detergent formulated to control dye transfer and sudsing in high efficiency washing machines
ATE337308T1 (de) 1999-12-08 2006-09-15 Procter & Gamble Mit ethern verschlossene poly(oxyalkylierte) alkoholtenside
US6855680B2 (en) 2000-10-27 2005-02-15 The Procter & Gamble Company Stabilized liquid compositions
US6864223B2 (en) 2000-12-27 2005-03-08 Colgate-Palmolive Company Thickened fabric conditioners
ITMI20010884A1 (it) * 2001-04-27 2002-10-27 3V Sigma Spa Composizioni detergenti
CN1397589A (zh) * 2001-07-18 2003-02-19 三菱瓦斯化学株式会社 光学材料生产方法
US20040238791A1 (en) 2001-09-03 2004-12-02 Simon Champ Reinforcement of the effect of optical brighteners by means of polymers
US20030060387A1 (en) * 2001-09-20 2003-03-27 Unilever Home And Personal Care, Usa, Division Of Conopco, Inc. Water-soluble package with fluorescent dye in the film
WO2003097776A1 (en) * 2002-05-16 2003-11-27 The Procter & Gamble Company Fabric conditioning composition comprising agent for enhancing the appearance of the rinse solution
EP1504082A1 (en) 2002-05-16 2005-02-09 The Procter & Gamble Company Rinse-added fabric treatment composition and methods and uses thereof
EP1396536B1 (en) 2002-09-05 2005-10-19 The Procter & Gamble Company Structuring systems for fabric treatment compostions
WO2004048418A2 (en) 2002-11-26 2004-06-10 Hercules Incorporated Soluble, associative carboxymethylcellulose, method of making, and uses thereof
US7022656B2 (en) 2003-03-19 2006-04-04 Monosol, Llc. Water-soluble copolymer film packet
US7135451B2 (en) 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch
GB0314210D0 (en) * 2003-06-18 2003-07-23 Unilever Plc Laundry treatment compositions
BRPI0515042A (pt) * 2004-09-23 2008-07-01 Unilever Nv composição de tratamento para a lavagem de roupas, e, método de tratamento de um têxtil
US20060122093A1 (en) 2004-12-07 2006-06-08 Permejo Fides L R Laundry detergent composition with mixed builder system
CN101072859A (zh) * 2004-12-07 2007-11-14 宝洁公司 含有混合助洗剂体系的衣物洗涤剂组合物
WO2006088953A1 (en) 2005-02-17 2006-08-24 Hercules Incorporated Blocky hydroxyethylcellulose, derivatives thereof, process of making, and uses thereof
PL1754781T3 (pl) * 2005-08-19 2013-09-30 Procter & Gamble Stała kompozycja detergentowa do prania zawierająca anionowy środek powierzchniowo czynny i technologię wspomagania wapniem
ES2960774T3 (es) 2006-01-23 2024-03-06 Procter & Gamble Composiciones que contienen enzima y agente de matizado de tejidos
MY150083A (en) * 2006-02-17 2013-11-29 Unilever Plc Laundry treatment compositions
BRPI0707889B1 (pt) * 2006-02-24 2019-07-09 Unilever N.V. Formulação aquosa de detergente líquido para lavagem de roupas
WO2007111892A2 (en) * 2006-03-22 2007-10-04 The Procter & Gamble Company Liquid treatment composition
JP5405488B2 (ja) * 2008-01-04 2014-02-05 ザ プロクター アンド ギャンブル カンパニー 酵素及び布地色調剤を含む組成物
ATE539141T1 (de) 2008-06-13 2012-01-15 Procter & Gamble Beutel mit mehreren kammern
EP2135933B1 (en) * 2008-06-20 2013-04-03 The Procter and Gamble Company Laundry composition
EP2166078B1 (en) * 2008-09-12 2018-11-21 The Procter & Gamble Company Laundry particle made by extrusion comprising a hueing dye
BR112013009698B1 (pt) * 2010-10-22 2020-04-28 Milliken & Co composto de agentes de azulagem
US20120101018A1 (en) 2010-10-22 2012-04-26 Gregory Scot Miracle Bis-azo colorants for use as bluing agents
US8378083B2 (en) 2010-10-22 2013-02-19 Milliken & Company Bis-azo colorants for use as bluing agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725384A (en) * 1969-04-17 1973-04-03 Ciba Geigy Ag Substituted phenyl-azo-phenyl-azo-phenyl compounds
US3762859A (en) * 1971-03-15 1973-10-02 Colgate Palmolive Co Enhancing the apparent whiteness of fabrics by applying an effective amount of an alkali and heat stable water soluble disazo blue dyestuff fabric softening and detergent composition therefor
WO2005040286A1 (en) * 2003-10-27 2005-05-06 Clariant International Ltd Storagestable concentrated aqueous solutions of anionic dis- or tetrazo dyestuffs
WO2010024468A1 (en) * 2008-09-01 2010-03-04 The Procter & Gamble Company Sulfonate group-containing copolymers and manufacturing method thereof

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10876079B2 (en) 2010-10-22 2020-12-29 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
US20150291918A1 (en) * 2010-10-22 2015-10-15 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
US10219855B2 (en) 2012-04-24 2019-03-05 Cibiem, Inc. Endovascular catheters and methods for carotid body ablation
US9757180B2 (en) 2012-04-24 2017-09-12 Cibiem, Inc. Endovascular catheters and methods for carotid body ablation
US9393070B2 (en) 2012-04-24 2016-07-19 Cibiem, Inc. Endovascular catheters and methods for carotid body ablation
US9540599B2 (en) * 2012-05-09 2017-01-10 Milliken & Company Laundry detergent composition comprising a particle having hueing agent and clay
US20130303428A1 (en) * 2012-05-09 2013-11-14 Milliken & Company Laundry Detergent Composition Comprising A Particle Having Hueing Agent and Clay
US20130303429A1 (en) * 2012-05-09 2013-11-14 The Procter & Gamble Company Laundry detergent composition comprising a particle having hueing agent and clay
US9540600B2 (en) * 2012-05-09 2017-01-10 The Procter & Gamble Company Laundry detergent composition comprising a particle having hueing agent and clay
US9398930B2 (en) 2012-06-01 2016-07-26 Cibiem, Inc. Percutaneous methods and devices for carotid body ablation
US9402677B2 (en) 2012-06-01 2016-08-02 Cibiem, Inc. Methods and devices for cryogenic carotid body ablation
US9808303B2 (en) 2012-06-01 2017-11-07 Cibiem, Inc. Methods and devices for cryogenic carotid body ablation
US9283033B2 (en) * 2012-06-30 2016-03-15 Cibiem, Inc. Carotid body ablation via directed energy
US20140005706A1 (en) * 2012-06-30 2014-01-02 Mark Gelfand Carotid Body Ablation Via Directed Energy
US9955946B2 (en) 2014-03-12 2018-05-01 Cibiem, Inc. Carotid body ablation with a transvenous ultrasound imaging and ablation catheter
WO2015187757A1 (en) 2014-06-06 2015-12-10 The Procter & Gamble Company Detergent composition comprising polyalkyleneimine polymers
US9951296B2 (en) 2015-03-30 2018-04-24 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9951301B2 (en) 2015-03-30 2018-04-24 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9957470B2 (en) 2015-03-30 2018-05-01 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US9957466B2 (en) 2015-03-30 2018-05-01 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US10053654B2 (en) 2015-04-02 2018-08-21 The Procter & Gamble Company Solid free-flowing particulate laundry detergent composition
US20160312158A1 (en) * 2015-04-23 2016-10-27 The Procter & Gamble Company Detergent compositions
US10633617B2 (en) * 2015-04-23 2020-04-28 The Procter & Gamble Company Detergent compositions
US10041024B2 (en) 2016-01-29 2018-08-07 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
WO2017132003A1 (en) * 2016-01-29 2017-08-03 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
US9719056B1 (en) * 2016-01-29 2017-08-01 The Procter & Gamble Company Bis-azo colorants for use as bluing agents
WO2019075143A1 (en) * 2017-10-12 2019-04-18 The Procter & Gamble Company LEUCO-COLORANTS AS AZURING AGENTS IN LAUNDRY CARE COMPOSITIONS
US10876080B2 (en) 2017-10-12 2020-12-29 The Procter & Gamble Company Leuco colorants as bluing agents in laundry care compositions

Also Published As

Publication number Publication date
WO2012054823A8 (en) 2012-05-31
US20150291918A1 (en) 2015-10-15
ZA201302890B (en) 2014-10-29
BR112013009798A2 (pt) 2016-07-26
CN103168097A (zh) 2013-06-19
MX2013004463A (es) 2013-06-07
BR112013009793A2 (pt) 2016-07-26
CA2815479C (en) 2016-09-27
US20120129753A1 (en) 2012-05-24
WO2012054835A1 (en) 2012-04-26
MX2013004461A (es) 2013-06-05
MX357338B (es) 2018-07-04
CN103339245A (zh) 2013-10-02
CN103180425A (zh) 2013-06-26
EP2630227A1 (en) 2013-08-28
JP6049679B2 (ja) 2016-12-21
WO2012054821A1 (en) 2012-04-26
EP2630229A1 (en) 2013-08-28
CN103180425B (zh) 2016-09-21
US10876079B2 (en) 2020-12-29
MX357341B (es) 2018-07-04
CN103339245B (zh) 2015-02-04
BR112013009794A2 (pt) 2016-07-26
US20120122750A1 (en) 2012-05-17
BR112013009792A2 (pt) 2016-07-26
JP2013544916A (ja) 2013-12-19
BR112013009791A2 (pt) 2016-08-09
MX357340B (es) 2018-07-04
CN103180424B (zh) 2015-09-16
MX357388B (es) 2018-07-06
US20120122751A1 (en) 2012-05-17
US9701930B2 (en) 2017-07-11
BR112013009791B1 (pt) 2020-09-29
MX357342B (es) 2018-07-04
ES2699751T3 (es) 2019-02-12
MX2013004459A (es) 2013-06-05
WO2012054820A1 (en) 2012-04-26
AR083503A1 (es) 2013-02-27
US9499775B2 (en) 2016-11-22
MX2013004462A (es) 2013-06-07
JP5833130B2 (ja) 2015-12-16
US9708572B2 (en) 2017-07-18
EP2630225A1 (en) 2013-08-28
EP2630226A1 (en) 2013-08-28
US20120129751A1 (en) 2012-05-24
WO2012054827A1 (en) 2012-04-26
EP2630228A1 (en) 2013-08-28
EP2630229B1 (en) 2018-09-19
WO2012054823A1 (en) 2012-04-26
CN103201370A (zh) 2013-07-10
CN105695160B (zh) 2018-12-18
CN105695160A (zh) 2016-06-22
MX2013004460A (es) 2013-06-05
CA2815479A1 (en) 2012-04-26
CN103168097B (zh) 2016-01-20
PL2630229T3 (pl) 2019-03-29
EP2630227B1 (en) 2016-03-23
JP2015120906A (ja) 2015-07-02
CN103180424A (zh) 2013-06-26
US20120129752A1 (en) 2012-05-24
US9708573B2 (en) 2017-07-18

Similar Documents

Publication Publication Date Title
US20120101018A1 (en) Bis-azo colorants for use as bluing agents
EP2630197B1 (en) Bis-azo colorants for use as bluing agents
US11299635B2 (en) Bis-Azo colorants for use as bluing agents
WO2012054058A1 (en) Bis-azo colorants for use as bluing agents
WO2011011799A2 (en) Thiophene azo dyes and laundry care compositions containing the same
US10435651B2 (en) Thiophene azo dyes and laundry care compositions containing the same
US9556337B2 (en) Thiophene azo dyes and laundry care compositions containing the same
US10041024B2 (en) Bis-azo colorants for use as bluing agents
US11078366B2 (en) Bis-azo colorants for use as bluing agents

Legal Events

Date Code Title Description
AS Assignment

Owner name: THE PROCTER & GAMBLE COMPANY, OHIO

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:MIRACLE, GREGORY SCOT;MAHAFFEY, ROBERT L.;HONG, XIAOYONG MICHAEL;AND OTHERS;SIGNING DATES FROM 20110106 TO 20110124;REEL/FRAME:025721/0074

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION