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WO2023014672A1 - Compositions comprenant des composés de guanidine, leur procédé de préparation et leurs procédés d'utilisation - Google Patents

Compositions comprenant des composés de guanidine, leur procédé de préparation et leurs procédés d'utilisation Download PDF

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Publication number
WO2023014672A1
WO2023014672A1 PCT/US2022/039094 US2022039094W WO2023014672A1 WO 2023014672 A1 WO2023014672 A1 WO 2023014672A1 US 2022039094 W US2022039094 W US 2022039094W WO 2023014672 A1 WO2023014672 A1 WO 2023014672A1
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WIPO (PCT)
Prior art keywords
composition
fabrics
laundry
formula
guanidine
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Ceased
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PCT/US2022/039094
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English (en)
Inventor
Manuel Gamez-Garcia
Yan Zhou
Sounak SARKAR
Karyn B. Visscher
Raymond Bret Clark
Bilal S. Marie
Surya Kamin
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ISP Investments LLC
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ISP Investments LLC
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Publication of WO2023014672A1 publication Critical patent/WO2023014672A1/fr
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    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3272—Urea, guanidine or derivatives thereof

Definitions

  • COMPOSITIONS COMPRISING GUANIDINE COMPOUNDS, PROCESS FOR PREPARING THE SAME AND METHODS OF USE THEREOF FIELD OF THE INVENTION relates generally to a composition comprising guanidine derivatives.
  • the present disclosure further relates to a laundry or cleaning composition comprising the same. BACKGROUND OF THE INVENTION [0002] Domestic and commercial laundry practices often lead to garment color fading and color transfer from one cloth to another. The effect of color transfer is particularly undesirable when white fabrics are involved.
  • EP0754748 teaches a dye transfer inhibiting composition
  • a dye transfer inhibiting composition comprising vinylpyridine copolymers formed from formic acid, acrylic acid, maleic acid, vinylpyrrolidone, and vinyl acetate as a dye transfer inhibitor.
  • Preferred copolymers are based on 4-vinylpyridine with vinylpyrrolidone, acrylic acid and maleic acid.
  • United States Patent No. 5,458,809 describes the use of poly(4-vinylpyridine-N-oxide) along with an effect amount of cleaning surfactant system as a dye transfer inhibiting detergent composition.
  • DE 2814287A describes a detergent composition containing N-vinyl imidazole homo- or copolymer as a discoloration- inhibiting additive in combination with anionic and/or nonionic surfactants and other detergent ingredients.
  • PCT Publication No. 95/03390 describes dye transfer inhibition by complexation with polymers of polyvinylpyrrolidone, polyamine N-oxide containing polymer, and N-vinyl imidazole N-vinylpyrrolidone copolymer.
  • United States Patent No. 5,460,752 describes a dye transfer inhibiting detergent composition comprising poly(4-vinylpyridine-N- oxide).
  • United States Patent No.5,627,151 describes the use of free-radically copolymerized copolymers of 1-vinylpyrrolidone and 1-vinylimidazole with nitrogen-containing ethylenically unsaturated monomers in the form of the free bases or in the form of the salts with organic or inorganic acids or in quaternized form for inhibiting dye transfer during the wash.
  • PCT Publication No. 95/27038 describes the use of poly(4-vinylpyridine-N-oxide), polyvinylpyrrolidone (PVP), polyvinylpyrrolidone-vinyl imidazole copolymer as dye transfer inhibitors in laundry detergent bars. [0007] However, the mechanism of dye transfer is rather more complex in nature.
  • thermodynamic parameters driving each one of these stages is the dye chemical potential associated with the dyeing process at each stage. Dye transfer from colored fabrics to white or other light-colored fabrics during laundry operations occurs thus because of cascading dye transport process driven by sequential decrements in the dye chemical potentials from one stage to the next one.
  • 103497194 teaches a pesticide composition containing a multi-nitrogen bicyclic compound wherein the compound is prepared by reacting guanidine carbonate, urea, and glyoxal.
  • Xinghui Jin et al. (“Synthesis and Properties of Energetic Materials Based on 1,3 ⁇ Diazocyclopentane” European Journal of Organic Chemistry, 2019, Issue 5, 988-994) teach a family of bi-heterocyclic energetic materials based on 1,3 ⁇ diazocyclopentane.
  • the present disclosure provides a composition comprising: (i) about 0.001 wt.% to about 50.0 wt.% of compounds of Formula (I) and Formula (II); or Formula (I) Formula (II) (ii) about 0.001 wt.% to about 50.0 wt.% of a reaction product of guanidine or its salts with glyoxal.
  • the compounds of Formula (I) and Formula (II) are present in an amount of from about 0.001 wt.% to about 20.0 wt.%, based on the total weight of the composition.
  • the compound of Formula (I) is a racemic mixture of the compounds of Formulae (Ia) and (Ib).
  • Formula (Ia) Formula (Ib) [0015]
  • the compounds of Formula (I) and Formula (II) are produced from the reaction of guanidine salt with glyoxal.
  • the guanidine salt is selected from the group consisting of guanidine carbonate, guanidine hydrochloride, guanidine sulfate, guanidine acetate, guanidine nitrate, guanidine phosphate, and guanidine sulfamate.
  • the composition is a nutrition composition, a food composition, a beverage composition, a pharmaceutical composition, a laundry or cleaning composition, a coating composition, a biocide composition, a construction composition, an energy composition, an industrial composition, an oilfield composition, a personal care composition, a household composition, a performance composition, an agricultural composition, a cosmetic composition, a pesticide composition, a veterinary composition, a fuel composition, a lubricant composition, an adhesive composition, a textile composition, an ink composition, a membrane composition, or a disinfectant composition.
  • the composition is a laundry or cleaning composition.
  • the composition prevents dye bleeding and inhibits dye transfer during laundering of articles.
  • the composition exhibits color maintenance or color wash fastness of at least about 50 % for at least 3 wash cycles.
  • the present disclosure provides a laundry or cleaning composition, the composition comprising: (i) about 0.001 wt.% to about 50.0 wt.% of compounds of Formula (I) and Formula (II); or Formula (I) Formula (II) (ii) about 0.001 wt.% to about 50.0 wt.% of a reaction product of guanidine or its salts with glyoxal.
  • the present disclosure provides a process for (i) preventing dye bleeding and (ii) inhibiting dye transfer during laundering of articles, wherein the process comprising contacting the articles with the laundry or cleaning composition of the present disclosure.
  • the article includes a woven or a non- woven article selected from the group consisting of natural fabrics, synthetic fabrics, natural non-woven fabrics, synthetic non-woven fabrics, cotton fabrics, denim, polyacrylic fabrics, polyamide fabrics, polyester fabrics, polyolefin fabrics, rayons, wool, linen, jute, ramie, hemp, sisal, regenerated cellulosic fibers, leather, and combinations thereof.
  • the present disclosure provides a process of laundering and/or maintaining the appearance of an article, the process comprising the steps of: (i) washing or contacting one or more articles with a wash solution comprising the composition of the present disclosure at one or more points during the main wash of laundry or cleaning process; (ii) rinsing the articles with water or a rinse liquor; and (iii) drying the articles, wherein the article includes a woven or a non-woven article selected from the group consisting of natural fabrics, synthetic fabrics, natural non-woven fabrics, synthetic non-woven fabrics, cotton fabrics, denim, polyacrylic fabrics, polyamide fabrics, polyester fabrics, polyolefin fabrics, rayons, wool, linen, jute, ramie, hemp, sisal, regenerated cellulosic fibers, leather, and combinations thereof.
  • the present disclosure provides a process of providing an appearance of reduced wrinkles and/or reduced lint of an article comprising the steps of: (i) washing or contacting one or more articles with a wash solution comprising the composition of the present disclosure at one or more points during the main wash of laundering or cleaning process; (ii) rinsing the articles with water or a rinse liquor; and (iii) drying the articles, wherein the article includes a woven or a non-woven article selected from the group consisting of natural fabrics, synthetic fabrics, natural non-woven fabrics and/or synthetic non-woven fabrics, cotton fabrics, denim, polyacrylic fabrics, polyamide fabrics, polyesters fabrics, polyolefins, rayons, wool, linen, jute, ramie, hemp, sisal, regenerated cellulosic fibers, leather, and combinations thereof.
  • the present disclosure provides a detergent composition
  • a detergent composition comprising: (i) about 0.001 wt.% to about 50.0 wt.% of compounds of Formula (I) and Formula (II); or Formula (I) Formula (II) (ii) about 0.001 wt.% to about 50.0 wt.% of a reaction product of guanidine or its salts with glyoxal; (ii) 0.01 wt.% to 50.0 wt.% of at least one surfactant selected from the group consisting of anionic surfactants, an amphoteric and zwitterionic surfactant, and non-ionic surfactants; and (iii) 0.01 wt.% to 25.0 wt.% of at least one laundry or cleaning additive.
  • inventive concept(s) Before explaining at least one embodiment of the inventive concept(s) in detail by way of exemplary drawings, experimentation, results, and laboratory procedures, it is to be understood that the inventive concept(s) is not limited in its application to the details of construction and the arrangement of the components set forth in the following description or illustrated in the drawings, experimentation and/or results.
  • inventive concept(s) is/are capable of other embodiments or of being practiced or carried out in various ways.
  • the language used herein is intended to be given the broadest possible scope and meaning; and the embodiments are meant to be exemplary - not exhaustive.
  • phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting.
  • the term “at least one” will be understood to include one as well as any quantity more than one, including but not limited to, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc.
  • the term “at least one” may extend up to 100 or 1000 or more, depending on the term to which it is attached; in addition, the quantities of 100/1000 are not to be considered limiting, as higher limits may also produce satisfactory results.
  • the use of the term “at least one of X, Y and Z” will be understood to include X alone, Y alone, and Z alone, as well as any combination of X, Y and Z.
  • the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.
  • the term “or combinations thereof” as used herein refers to all permutations and combinations of the listed items preceding the term.
  • A, B, C, or combinations thereof is intended to include at least one of: A, B, C, AB, AC, BC, or ABC, and if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB.
  • expressly included are combinations that contain repeats of one or more item or term, such as BB, AAA, MB, BBC, AAABCCCC, CBBAAA, CABABB, and so forth.
  • BB BB
  • AAA AAA
  • MB BBC
  • AAABCCCCCC CBBAAA
  • CABABB CABABB
  • the term “article(s)” refers to a textile material such as a cloth or a fabric made from fibrous structures that can include, but are not limited to, fibers/filaments/yarns. These fibrous structures can be staple length fibers or continuous fibers, and can be natural fibers such as cotton, wool, silk, jute and mixtures thereof, or synthetic fibers such as polyacrylonitrile, nylon, polyamide, polyesters, triacetate, polyethylene, propylene, and mixtures thereof, or any combinations of the natural and synthetic fibers.
  • Non-limiting examples of such textile materials can include natural fabrics, synthetic fabrics, natural non- woven fabrics, synthetic non-woven fabrics, cotton fabrics, denim, polyacrylic fabrics, polyamide fabrics, polyester fabrics, polyolefin fabrics, rayons, wool, linen, jute, ramie, hemp, sisal, regenerated cellulosic fibers, leather, and combinations thereof.
  • the term “article(s)” can also encompass further products made from the textile materials. Suitable examples of such products can include, but are not limited to, clothing, garments, towels, other bath linens, bed linens, tablecloths, carpets, curtains, upholstery coverings, sleeping bags, tents, shoes, and car interior (such as car seat covers, car floor mats).
  • laundry process relates to both household laundering and industrial laundering and means the process of cleaning or treating articles with a laundering solution comprising a laundry or cleaning composition of the present disclosure.
  • laundry process in the context of the present disclosure can include, but are not limited to, (i) pre-treating or soaking cycle before main wash, (ii) main -wash cycle, (iii) rinse cycle; (iv) post-wash treating cycle; or (v) drying cycle.
  • the laundry process can, for example, be carried out either using e.g., a household or an industrial washing machine or can be carried out in a container useful for handwashing, for example, a tub, or a bucket, or any other container suitable for hand washing.
  • laundering or “laundry processes’ can be used interchangeably in the present disclosure.
  • laundry products means products used to meet a variety of requirements in laundry processes, such as stain or soil removal, bleaching, fabric conditioning or softening, or disinfectant requirements. Suitable examples of such laundry products can include, but are not limited to, detergents, stain or odor eliminators, fabric softeners or conditioners.
  • the laundry products may also include other various types of laundry aids used to improve laundering results or to accomplish specific functions. Suitable examples of such laundry aids can include, but are not limited to, enzyme pre-soaks, boosters, bleaches, conditioning agents, dry-cleaning fluids, optical brighteners, laundry starch or ironing aids, laundry sizing or finishes, or water softeners.
  • the laundry products according to the present discourse can be present in different physical forms including, but not limiting to, liquid, dry powder, granules, particulate form, gel, paste, aerosol, bar, tablet, pod or spray compositions. Further, the laundry products of the present disclosure can be used for laundering or cleaning or treating variety of articles and can be used for both household laundering and industrial laundering.
  • detergent composition refers to a composition used as a cleansing agent for the removal of soil and dirt from articles to be cleaned.
  • the detergent composition can be in different physical forms such as liquid, gel, dry powder or granular form, a paste, a gel, a bar, a homogenous tablet, a tablet having two or more layers, or a pouch having one or more compartments and can include, but is not limited to, liquid or solid laundry detergents, and fine fabric detergents.
  • amalgamates means a material or a combination of materials that can be used along with the composition of the present disclosure to deliver one or more of the following benefits to the articles that include, but are not limited to, fabric softening, fabric lubrication, fabric relaxation, wrinkle resistance, wrinkle reduction, ease of ironing, abrasion resistance, fabric smoothing, anti-felting, anti-pilling, crispness, appearance enhancement, appearance rejuvenation, anti-shrinkage, in-wear shape retention, fabric elasticity, fabric tensile strength, fabric tear strength, static reduction, water absorbency or repellency, stain repellency, soil, dirt and/or stain removal, refreshing, anti- microbial, odor resistance, and any combinations thereof.
  • adjunct materials can include, but are not limited, pH adjusters, surfactants, emulsifiers, detergents adjuvants, builders, rheology modifiers, thickening agents, antioxidants, radical scavengers, chelants, antifoaming agents, conditioning agents, antistatic agent, antimicrobials or preservatives, dyes or colorants, viscosity control agents, pearlizing and opacifying agents, chlorine scavenger, brighteners, perfumes, and mixtures thereof.
  • color wash fastness refers to maintaining the color of articles when they are exposed to the process and conditions of laundering. Washing clothes is known to change the color and thus the appearance of the articles from their original color.
  • a dye may be reasonably fast to one agent and only moderately fast to another.
  • the present disclosure provides a composition comprising guanidine compounds.
  • the guanidine compounds can include compounds of Formula (I) and Formula (II) having the following structure.
  • Formula (I) Formula (II) [0037]
  • the compound of Forumula (I) can be a racemic mixture of cis- and trans-form of the following structural Formulae (Ia and Ib).
  • Formula (Ia) Formula (Ib) [0038]
  • the compounds of Formula (I) and Formula (II) can be present in an amount of from about 0.001 wt.% to about 50.0 wt.
  • the compounds of Formula (I) and Formula (II) according to the present disclosure are the guanidine compounds obtained from the reaction of guanidine salts with glyoxal.
  • guanidine salts which can be used for the purpose of the present disclosure can include, but are not limited to, guanidine carbonate, guanidine hydrochloride, guanidine sulfate, guanidine acetate, guanidine nitrate, guanidine phosphate, and guanidine sulfamate.
  • the present disclosure provides a process for preparing the compounds of Formula (I) and Formula (II) by reacting a guanidine salt with glyoxal.
  • guanidine salt with glyoxal For the reaction of guanidine salt with glyoxal to start and proceed, it is first necessary to have the guanidine molecules freed from their salt form, and this process may require a high pH ( ⁇ 9.0 – 11.5) in the aqueous solutions, depending on the type of guanidine salt used. Typical products obtained from the reaction between guanidine and glyoxal are shown in Fig.1. [0040]
  • the composition according to the present disclosure can be used in various end-user applications.
  • the composition can be a nutrition composition, a food composition, a beverage composition, a pharmaceutical composition, a laundry or cleaning composition, a coating composition, a biocide composition, a construction composition, an energy composition, an industrial composition, an oilfield composition, a personal care composition, a household composition, a performance composition, an agricultural composition, a cosmetic composition, a pesticide composition, a veterinary composition, a fuel composition, a lubricant composition, an adhesive composition, a textile composition, an ink composition, a membrane composition, or a disinfectant composition.
  • the composition can be a laundry or cleaning composition.
  • the compounds of Formula (I) and Formula (II) work as effective dye transfer inhibitors (DTI) and also as effective dye anti-bleeding agents.
  • the laundry or cleaning composition according to the present disclosure can be used for cleaning or treating articles during laundry processes. Alternatively, the laundry or cleaning composition of the present disclosure can be used outside laundry applications, for example, in compositions to minimize dry transfer on newly manufactured articles including, but not limiting to, clothing, upholstery, and carpeting.
  • the compounds of Formula (I) and Formula (II) according to the present disclosure exert a dual effect, i.e. protecting articles from changing color due to undesirable dye transfer while at the same time protecting colored articles against dye bleeding.
  • the laundry or cleaning composition according to the present disclosure can be a solid composition or a liquid composition.
  • the laundry or cleaning composition can be a solid composition comprising: (i) the compounds of the Formula (I) and Formula (II) of the present disclosure; and (ii) at least one solid carrier.
  • Any suitable adsorbent material can be used as a solid carrier for the purpose of the present composition. Suitable examples of such solid carriers can include, but are not limited to, silica, zeolites, and bentonites.
  • the suitable carrier can be silica.
  • the laundry or cleaning composition can be a liquid composition comprising: (i) the compounds of Formula (I) and Formula (II) of the present disclosure; and (ii) at least one solvent.
  • the solvent can be water.
  • the compounds of Formula (I) and Formula (II) can be present in an amount of from about 0.001 wt.% to about 50.0 wt. %, or from about 0.001 wt.% to 20.0 wt.%, or from about 0.01 wt.% to about 10.0 wt.%, or from about 0.05 wt.% to about 10.0 wt.%, based on the total weight of the laundry or cleaning composition.
  • the laundry or cleaning composition can be used as a laundry product during the laundering of articles.
  • the laundry or cleaning composition can include, but is not limited to, detergents or soaps; fabric softeners or conditioners; pre-wash treatment compositions such as soil or stain removal agents or enzyme pre-soak agents; post-rinse fabric treatment compositions such as fabric finishing agents and sizing agents, starch, ironing aids and the like.
  • suitable examples of such compositions can include, but are not limited to, a unit dose formulation, a dry-cleaning composition, boosters, bleaches, conditioning agents, optical brighteners, or water softeners.
  • the laundry or cleaning composition according to the present discourse can be a liquid composition or a solid composition and can be present in different physical forms including, but not limiting to, a liquid, a dry powder or granular form, a particulate or its encapsulated coated form, a dispersion, a gel, a paste, an aerosol, a bar, a tablet, a pod or a spray. Further, the laundry or cleaning composition according to the present disclosure can be used for laundering or cleaning or treating variety of articles and can be used for both household laundering and industrial laundering. [0045] The laundry or cleaning composition according to the present disclosure can further comprise at least adjunct material. These adjunct materials can be added to provide one or more additional benefits or properties to the articles being treated with the laundry or cleaning composition of the present disclosure.
  • Additional benefits or properties can include, but are not limited to, fabric softening, fabric lubrication, fabric relaxation, durable press, wrinkle resistance, wrinkle reduction, ease of ironing, abrasion resistance, fabric smoothing, anti- felting, anti-pilling, crispness, appearance enhancement, appearance rejuvenation, anti- shrinkage, in-wear shape retention, fabric elasticity, fabric tensile strength, fabric tear strength, static reduction, water absorbency or repellency, stain repellency, soil, dirt and/or stain removal, refreshing, anti-microbial, odor resistance, and any combinations thereof.
  • adjunct materials can include, but are not limited to, solvents, adsorbents, surfactants, pH adjusters, emulsifiers, detergents adjuvants, builders, rheology modifiers, thickening agents, antioxidants, radical scavengers, chelants, foam control agents, conditioning agents, antistatic agents, antimicrobials or preservatives, dyes or colorants, viscosity control agents, pearlizing and opacifying agents, chlorine scavengers, brighteners, fragrance or perfumes, dispersants, filler compounds, hydrotropes or solubilizing agents, functional polymers, stabilizers, soil release polymers, antimicrobials, insect repellents, dust mite repellents, UV absorbers, light management agents, bleaching agents, oxidation catalysts, zeolites, suppressing agents, and mixtures thereof.
  • adjunct materials can be present in an amount of from about 99.999 wt.% to about 50.0 wt.%, or from about 90.0 wt.% to about 50.0 wt.%, or from about 80.0 wt.% to about 50.0 wt.%, or from about 70.0 wt.% to about 50.0 wt.%, based on the total weight of the laundry or cleaning composition.
  • the laundry or cleaning composition can be used along with other commercially available laundry products during the laundering of articles.
  • the laundry or cleaning composition of the present disclosure can be combined or mixed with the commercially available laundry products and can be used during various laundry processes.
  • any commercially available laundry products which are well known to those skilled in the relevant art can suitably be used in the present disclosure.
  • suitable examples of such products for the purpose of the present disclosure can include, but are not limited to, detergents, stain or odor eliminators, fabric softeners, or conditioners.
  • the commercially available laundry products may also include other various types of laundry aids used to improve laundering results or to accomplish specific functions.
  • Suitable examples of such laundry aids can include, but are not limited to, enzyme pre-soaks, pre-wash soil or stain removal agents, boosters, bleaches, conditioning agents, dry- cleaning fluids, optical brighteners, laundry starch or ironing aids, laundry finishing agents and sizing agents or water softeners.
  • the laundry and cleaning composition can be added to the commercial laundry products in an amount that would result in about 50 ppm to about 250 ppm of the compounds of Formula (I) and Formula (II) in a diluted wash liquid.
  • the laundry or cleaning composition can be a detergent composition.
  • the detergent composition according to the present disclosure can comprises: (i) the compounds of Formula (I) and Formula (II) of the present disclosure as a dye transfer inhibitor (DTI) and dye anti-bleeding agent; (ii) at least one surfactant; and (iii) at least one laundry adjunct material.
  • the compounds of Formula (I) and Formula (II) can be present in an amount of from about 0.001 wt.% to about 50.0 wt. %, or from about 0.001 wt.% to about 20.0 wt.% or from about 0.01 wt.% to about 10.0 wt.%, or from about 0.05 wt.% to about 10.0 wt.%, based on the total weight of the detergent composition.
  • a wide range of surfactants can be used in the present detergent composition. These surfactants can be an anionic surfactant, an amphoteric and zwitterionic surfactant, a nonionic surfactant, and any combinations thereof.
  • Anionic surfactants which are suitable for use herein can include the water-soluble salts.
  • the water-soluble salts can be alkali metal and ammonium salts of organic sulfuric reaction products having an alkyl group containing from about 10 to about 20 carbon atoms and a sulfonic acid or sulfuric acid ester group. (Included in the term “alkyl” is the alkyl portion of acyl groups).
  • one or more anionic detergents may be included in the composition, and this is often preferred.
  • the contemplated water soluble anionic detergent surfactants are the alkali metal (such as sodium and potassium) salts of the higher linear alkylbenzenesulfonates (LAS) and the alkali metal salts of sulfated ethoxylated and unethoxylated fatty alcohols, and ethyoxylated alkylphenols.
  • the particular salt will be suitably selected depending upon the particular formulation and the proportions therein.
  • a sodium alkylbenzenesulfonate surfactant is used in the composition of the present invention, it preferably has a linear (straight chain) alkyl radical of average length of about 11 to 13 carbon atoms (LAS).
  • Specific sulfated surfactants which can be used in the compositions of the present invention include sulfated ethoxylated and unethoxylated fatty alcohols, preferably linear (straight chain) primary or secondary monohydric alcohols with C10 -C18, preferably C12 - C16, alkyl groups and, if ethoxylated, on average about 1-15, preferably 3-12 moles of ethylene oxide (EO) per mole of alcohol, and sulfated ethoxylated alkylphenols with C8 -C16 alkyl groups, preferably C8 -C9 alkyl groups, and on average from 4-12 moles of EO per mole of alkyl phenol.
  • EO ethylene oxide
  • anionic surfactants are the sulfated ethoxylated linear alcohols (AES), such as the C12 -C16 alcohols ethoxylated with an average of from about 1 to about 12 moles of ethylene oxide per mole of alcohol.
  • a most preferred sulfated ethoxylated detergent is made by sulfating a C12 -C15 alcohol ethoxylated with 3 moles of ethylene oxide per mole of alcohol.
  • anionic surfactants can include, but are not limited to, (a) the sodium, potassium and ammonium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C8-C18 carbon atoms) such as those produced by reducing the glycerides of tallow or coconut oil; (b) the sodium, potassium and ammonium alkyl polyethoxylate sulfates, particularly those in which the alkyl group contains from about 10 to about 22 carbon atoms, or from about 12 to about 18 carbon atoms, and wherein the polyethoxylate chain contains from 1 to about 15, or from 1 to about 6 ethoxylate moieties; and (c) the sodium and potassium alkylbenzene sulfonates in which the alkyl group contains from about 9 to about 15 carbon atoms, in straight chain or branched chain configuration, e.g., those of the type described in U.S.
  • Suitable examples of nonionic surfactants useful for the detergent composition of the present disclosure can include alkoxylated materials, particularly addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids and fatty amines.
  • the alkoxylated materials can have the general formula: R—Y—(CH 2 CH 2 O) z H where R is a hydrophobic moiety, typically being an alkyl or alkenyl group, the group being linear or branched, primary or secondary, and having from about 8 to about 25 carbon atoms, or from about 10 to about 20 carbon atoms, or from about 10 to about18 carbon atoms.
  • R can also be an aromatic group, such as a phenolic group, substituted by an alkyl or alkenyl group as described above;
  • Y is a linking group, typically being O, CO.O, or CO.N(R1), where R1 is H or a C 1 -C 4 alkyl group; and
  • z represents the average number of ethoxylate (EO) units present, the number being about 8 or more, or about 10 or more, from about 10 to about 30, or from about 12 to about 25, or from about 12 to about 20.
  • suitable nonionic surfactants can include the ethoxylates of mixed natural or synthetic alcohols in the “coco” or “tallow” chain length.
  • the non-ionic surfactants can be condensation products of coconut fatty alcohol with about 15- 20 moles of ethylene oxide and condensation products of tallow fatty alcohol with about 10- 20 moles of ethylene oxide.
  • the ethoxylates of secondary alcohols such as 3-hexadecanol, 2-octadecanol, 4- eicosanol, and 5-eicosanol can also be used.
  • Exemplary ethoxylated secondary alcohols can have formulae C 12 -EO(20); C 14 -EO(20); C 14 -EO(25); and C 16 -EO(30).
  • the secondary alcohols can include TergitolTM 15-S-3(available from The Dow Chemical Company) and those disclosed in PCT/EP2004/003992, which is enclosed herein by reference in its entirety.
  • Polyol-based nonionic surfactants can also be used, examples including sucrose esters (such as sucrose monooleate), alkyl polyglucosides (such as stearyl monoglucoside and stearyl triglucoside), and alkyl polyglycerols.
  • the nonionic surfactants used in the present detergent composition can be reaction products of long-chain alcohols with several moles of ethylene oxide having a weight average molecular weight of about 300 to about 3000 Daltons.
  • One of the nonionic surfactants of the blend is a lower hydrophillic ethoxylate.
  • the lower hydrophillic ethoxylate is linear alcohol ethoxylate where a C9 -C11 and/or C12 -C18 linear alcohol chain is ethoxylated with an average of 1.0 to 5.0 moles of ethylene oxide per chain, or 2.0 to 4.0 moles of ethylene oxide.
  • the nonionic surfactant can also be a higher ethoxylate.
  • the higher ethoxylate is a linear alcohol ethoxylate where a C9 -C11 and/or C12 -C18 linear alcohol chain is ethoxylated with at least 6.0 moles of ethylene oxide per chain, or an average of 6.0 to 20.0 moles of ethylene oxide per chain, or an average of 6.0 moles to 12.0 moles of ethylene oxide per chain.
  • the ratio of lower ethoxylate to higher ethoxylate can be in the range of from about 1:10 to about 10:1, or from about 1:4 to 4:1.
  • the nonionic surfactants can be mixtures of C9 -C11 linear alcohols ethoxylated with an average of 2.5, 6.0 and 8.0 moles of ethylene oxide per chain.
  • the ratio of the 6 mole ethoxylates to 2.5 moles ethoxylates in the blend is preferably in the range of 1.5:1 to 2:1 and for 8 mole ethoxylates is in the range of 2.3:1.
  • Amphoteric surfactants suitable for use in the present laundry or cleaning composition can include those that are broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight or branched chain and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • an anionic water solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Examples of compounds falling within this definition are sodium 3-dodecyl-aminopropionate, sodium 3-dodecylaminopropane sulfonate, sodium lauryl sarcosinate, N-alkyl taurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of U.S. Pat. No.2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of U.S. Pat. No.2,438,091, and the products described in U.S. Pat. No.2,528,378.
  • Zwitterionic surfactants suitable for use according to the present disclosure can include those that are broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight or branched chain, and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Suitable examples of the zwitterionic surfactant can include betaines such as cocoamidopropyl betaine.
  • amphoteric surfactants suitable herein may also include alkyl amphoacetates including lauroamphoacetate and cocoamphoacetate.
  • Alkylamphoacetates can be comprised of monoacetates and diacetates. However, some type of alkylamphoacetates can have impurities and or unintended reaction products.
  • the surfactant can be present in an amount of from about 0.0 wt.% to about 80.0 wt.%, or from about 0.0 wt.% to about 50.0 wt.%, or from about 0.0 wt.% to about 20.0 wt.% of the total detergent composition.
  • the detergent composition can further include one or more laundry adjunct materials that are used in the conventional detergent compositions.
  • Such adjunct materials are well known to those skilled in the art and can include, but are not limited to, builders, ion exchangers, alkalies, anticorrosion materials, antiredeposition materials, optical brighteners, fragrances, dyes, chelating agents, enzymes, whiteners, brighteners, antistatic agents, suds control agents, solvents, hydrotropes, bleaching agents, bleach stabilizers or activators thereof, perfumes, water, buffering agents, soil removal agents, soil release agents, softening agents, opacifiers, inert diluents, graying inhibitors, stabilizers, polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, sunscreens, anti-corrosion agents, drape imparting agents, deodorants, emollients, moisturizers, foam boosters, germicides, lathering agents, skin conditioners, solvents, stabilizers
  • the detergent composition according to the present disclosure may further comprise detergency adjuvants or builders to improve the surface properties of surfactants.
  • Builders can be organic and/or inorganic.
  • the inorganic builders can include, but are not limited to, alkali metal ammonium or alkanolamine polyphosphates; alkali metal pyrophosphates; zeolites; silicates; alkali metal or alkaline earth metal borates, carbonates, bicarbonates or sesquicarbonates; and cogranules of alkali metal (sodium or potassium) silicate hydrates and of alkali metal (sodium or potassium) carbonates.
  • the organic builders can include, but are not limited to, organic phosphates; and polycarboxylic acids and/or their water-soluble salts and water-soluble salts of carboxylic polymers. Suitable examples of such organic builders can include, but are not limited to, polycarboxylate or hydroxypolycarboxylate ethers; polyacetic acids or their salts (nitriloacetic acid, N,N-dicarboxymethyl-2-aminopentanedioic acid, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, ethylenediaminetetraacetates, nitrilotriacetates,); (C5-C20 alkyl)succinic acid salts; polycarboxylic acetal esters; polyaspartic or polyglutamic acid salts; and citric acid, gluconic acid or tartaric acid or their salts.
  • Another embodiment of the present disclosure contemplates employing anti- redeposition agents that prevent soils that have been dislodged from articles from being redeposited such as Carboxy methyl cellulose (CMC), Polyvinyl pyrrolidone, Polyethylene glycol (PEG) and polyvinyl alcohol.
  • CMC Carboxy methyl cellulose
  • PEG Polyethylene glycol
  • the auxiliary cleaning agents can be copolymers of acrylic acid and of maleic anhydride or acrylic acid homopolymers type.
  • the bleaching active agents can be perborates or percarbonates type, which may or may not be combined with acetylated bleaching activators, such as N,N,N′,N′-tetraacetylethylenediamine (TAED), or chlorinated products of the chloroisocyanurates type, or chlorinated products of the alkali metal hypochlorites type.
  • acetylated bleaching activators such as N,N,N′,N′-tetraacetylethylenediamine (TAED), or chlorinated products of the chloroisocyanurates type, or chlorinated products of the alkali metal hypochlorites type.
  • TAED N,N,N′,N′-tetraacetylethylenediamine
  • Either hydrophobic or hydrophilic biocidal active agents can also be used.
  • a biocidal agent is considered “hydrophobic” when its solubility in water at 25°C is less than about 1% by weight, preferably less than about
  • hydrophobic biocidal agents can include, but are not limited to, para-chloro-meta-xylenol or dichloro-meta- xylenol, 4-chloro-m-cresol, resorcinol monoacetate, mono- or poly-alkyl or -aryl phenols, cresols or resorcinols, such as o-phenylphenol, p-tert-butylphenol or 6-n-amyl-m-cresol, alkyl and/or aryl-chloro- or -bromophenols, such as o-benzyl-p-chlorophenol, halogenated diphenyl ethers such as 2′,4,4′-trichloro-2-hydroxy-diphenyl ether (triclosan) and 2,2′-dihydroxy-5,5′- dibromo-diphenyl ether, and chlorophenesin (p-chloro-phenylgly
  • hydrophilic biocidal agents examples include cationic biocides such as quaternary monoammonium salts such as cocoalkylbenzyldimethylammonium, (C12- C14)alkylbenzyldimethylammonium, cocoalkyldichlorobenzyldimethylammonium, tetradecylbenzyldimethylammonium, didecyldimethylammonium or dioctyldimethylammonium chlorides, myristyltrimethylammonium or cetyltrimethylammonium bromides monoquaternary heterocyclic amine salts such as laurylpyridinium, cetylpyridinium or (C12-C14)alkylbenzylimidazolium chlorides, and triphenylphosphonium fatty alkyl salts such as myristyltriphenylphosphonium bromide.
  • quaternary monoammonium salts such as cocoalkylbenzyldimethyl
  • Polymeric biocides can also be used. Suitable examples of polymeric biocides can include, but are not limited to, those derived from the reactions of epichlorohydrin and of dimethylamine or of diethylamine, of epichlorohydrin and of imidazole, of 1,3-dichloro-2- propanol and of dimethylamine, of 1,3-dichloro-2-propanol and of 1,3-bis(dimethylamino)-2- propanol, of ethylene dichloride and of 1,3-bis(dimethylamino)-2-propanol, and of bis(2- chloroethyl) ether and of N,N′-bis(dimethylaminopropyl)-urea or thiourea; biguanidine polymeric hydrochlorides; amphoteric biocides such as derivatives of N-(N′-C8-C18 alkyl-3- aminopropyl)glycine, of N-(N′-(N′′
  • the detergent builders can be present in an amount of upto 50.0 wt.%, based on the total weight of the detergent composition.
  • Optical brighteners or whitening agents mask the appearance of an undesirable color, such as the yellowing of fabric that occurs naturally over time by introducing a complementary color.
  • Optical brighteners attach to articles, absorb invisible ultraviolet light and convert it to visible blue-violet light. The blue light that is emitted interacts with the yellow light emitted by the article, giving an overall appearance of whiteness.
  • Suitale examples of optical brighteners can include, but are not limited to, aminotriazines, coumarins and stilbenes.
  • Hydrotropes or solubilizers assist in maintaining the pouring characteristics of liquid detergents by preventing gel formation or separation into layers in the bottle. They maintain a uniform composition throughout the liquid detergent.
  • Suiable examples of hydrotropes can include, but are not limited to, xylene sulfonate, cumene sulfonate, some glycol ether sulphates and urea.
  • Foam regulators inhibit the formation of suds during the washing cycle.
  • Foam regulators prevent the formation of foam by disrupting the surfactants at the air-water interface of the forming bubble, or cause foam bubbles to collapse by forming hydrophobic bridges across multiple bubbles selected from soaps, siloxanes and paraffins.
  • Other optional laundry adjunct materials can also be added to provide one or more additional benefits or properties to the articles.
  • Additional benefits can include, but are not limited, appearance enhancement, appearance rejuvenation, in-wear shape retention, fabric elasticity, fabric tensile strength, fabric tear strength, fabric softening, fabric lubrication, fabric relaxation, durable press, wrinkle resistance, wrinkle reduction, ease of ironing, fabric smoothing, anti-felting, crispness, anti-shrinkage, fabric elasticity, static reduction, stain removal, stain repellency, refreshing, odor resistance, and any combinations thereof.
  • a complete list of ingredients routinely added to cleaning compositions is found in McCutcheon's 2012 Emulsifiers & Detergents and McCutcheon's Functional Materials directories of detergent ingredients.
  • adjunct materials can be present in an amount of from about 0.1 wt.% to about 30.0 wt.%, or from about 0.5 wt.% to about 10.0 wt.%, or from about 1.0 wt.% to about 5.0 wt.%, based on the total weight of the detergent composition.
  • the detergent composition of the present disclosure can be in the form of a liquid, a dry powder or granular form, a paste, a gel, a bar, a homogenous tablet, a tablet having two or more layers, or a pouch having one or more compartments.
  • the liquid and dry powder form of the detergent composition can exist in concentrated or compact form.
  • the dry granular detergent composition according to the present disclosure can also be in concentrated form or ‘compact form’, means they may have a relatively higher density than conventional granular detergents i.e.
  • the granular detergent compositions according to the present invention will contain a lower amount of "inorganic filler salt", compared to conventional granular detergents; typical filler salts are alkaline earth metal salts of sulphates and chlorides, typically sodium sulphate; "compact" detergents typically comprise not more than 10% filler salt.
  • the liquid detergent composition according to the present disclosure can also be in "compact form", in such case, the liquid detergent compositions according to the present disclosure will contain a lower amount of water, compared to conventional liquid detergents.
  • the laundry or cleaning composition can be a laundry softening composition.
  • the laundry softening composition are intended for use in the rinse cycle of the laundry operation.
  • the laundry softening composition of the present disclosure provides both articles softening as well as dry transfer inhibition and dye fastness benefits.
  • the laundry softening composition according to the present disclosure comprises (i) the composition having the compounds of Formula (I) and Formula (II) as herein above described; and (ii) at least one laundry softening agent. Any conventional softening agents which are well known to those skilled in the related art can suitably be used in the present laundry softening composition.
  • Non-limiting examples of such softening agents can include, but are not limited to, quaternary ammonium compounds such as dihydrogenated tallow dimethyl ammonium chloride, methyl bis-2-hydroxyethyl ammonium methyl sulfate, Methyl bis[ethyl (tallowate)]-2-hydroxyethyl ammonium methyl sulfate and the like.
  • the laundry softening composition according to the present invention can be in liquid form or dry form. In one non-limiting embodiment of the present disclosure, the laundry softening composition is in liquid form.
  • the liquid form of the laundry softening composition can typically comprises (i) from about 3.0 wt.% to about 50.0 wt.% of a laundry softening agent; and (ii) from about 0.03 wt.% to about 25.0 wt.% of the present composition having the compounds of Formula (I) and Formula (II) as a dye transfer inhibitor and dye anti-bleeding agent; and (iii) a liquid carrier.
  • the liquid carrier can preferably be water.
  • the amount of the laundry softening agent in the liquid compositions can typically varies from about 3.0 wt.% to about 50.0 wt.%, or from about 4.0 wt.% to about 30.0 wt.%, by total weight of the laundry softening composition. Further, the amount of the composition having the compounds of Formula (I) and (II) as a dye transfer inhibitor can vary from about 0.1 wt.% to about 15.0 wt.%, based on the total weight of the laundry softening composition. [0082] In another non-limiting embodiment of the present disclosure, the laundry softening composition can be in solid particulate form (dry powder form).
  • Such form of the composition can comprise from about 20.0 wt.% to about 90.0 wt.%, or from about 30.0 wt.% to about 70.0 wt.%, of the laundry softening agent; and (ii) from about 0.1 wt.% to about 80.0 wt.%, or from about 0.3 wt.% to about 50.0 wt.%, or from about 0.5 wt.% to about 25.0 wt.% of the present composition comprising the compounds of Formula (I) and Formula (II) as a dye transfer inhibitor and dye anti-bleeding agent.
  • the present invention also comprises dryer-added laundry softener compositions comprising: (i).
  • the laundry or cleaning composition of the present disclosure works as a very efficient dye transfer inhibitor.
  • the laundry or cleaning composition of the present disclosure can be used as a dye transfer inhibitor and also as a dye anti-bleeding agent during laundering of articles.
  • another aspect of the present disclosure provides a process for laundering or cleaning articles with the present laundry or cleaning composition.
  • the present disclosure provides a process of (i) preventing dye bleeding from colored articles and (ii) inhibiting dye transfer from one article to another co-article or the same article during laundry process involving colored articles.
  • the process can comprise (i) contacting one or more colored article with a laundering solution comprising the laundry or cleaning composition of the present application at one or more points during any of the laundry processes; and (ii) allowing the article to air dry naturally or mechanically tumble-drying them.
  • the laundry processes are well known to person skilled in the relevant art and can include, but are not limited to, (i) pre-treating or soaking cycle before main wash, (ii) main -wash cycle, (iii) rinse cycle; (iv) post-wash treating; and (v) drying cycle.
  • the process can be carried out during main wash laundry process wherein the process comprising: (i) contacting one or more article with a wash solution comprising the laundry or cleansing composition of the present disclosure at one or more points during the main wash of laundering or cleaning process; (ii) rinsing the washed articles with water; and (iii) allowing the washed and rinsed articles to air dry naturally or mechanically tumble-drying them.
  • the present disclosure provides a process of laundering and/or maintaining the appearance of an article, wherein the method comprises (i) contacting one or more article with a solution comprising the laundry or cleansing composition of the present disclosure at one or more points during any of the laundry processes; (ii) rinsing the article with water; and (iii) allowing the washed and rinsed article air dry naturally or mechanically tumble-drying them.
  • the present disclosure provides a process of providing appearance of reduced wrinkles and/or reduced lint of an article, wherein the process comprises: (i) contacting one or more article with a laundry solution comprising the laundry or cleaning composition of the present application at one or more points during any of the laundry processes; (ii) rinsing the article with water; and (iii) allowing the washed and rinsed article to air dry naturally or mechanically tumble-drying them.
  • the articles used in the process of the present disclosure can be a textile material such as a cloth or a fabric made from fibrous structures that can include, but are not limited to, fibers/filaments/yarns.
  • These fibrous structures can be staple length fibers or continuous fibers, and can be natural fibers such as cotton, wool, silk, jute and mixtures thereof, or synthetic fibers such as polyacrylonitrile, nylon, polyamide, polyesters, triacetate, polyethylene, propylene, and mixtures thereof, or any combinations of the natural and synthetic fibers.
  • Non-limiting examples of such textile materials can include natural fabrics, synthetic fabrics, natural non- woven fabrics, synthetic non-woven fabrics, cotton fabrics, denim, polyacrylic fabrics, polyamide fabrics, polyester fabrics, polyolefin fabrics, rayons, wool, linen, jute, ramie, hemp, sisal, regenerated cellulosic fibers, leather, and combinations thereof.
  • article(s) can also encompass further products made from the textile materials. Suitable examples of such products can include, but are not limited to, clothing, garments, towels, other bath linens, bed linens, tablecloths, carpets, curtains, upholstery coverings, sleeping bags, tents, shoes, and car interior (such as car seat covers, car floor mats).
  • the laundry or cleaning composition according to the present disclosure exhibits color maintenance or color wash fastness of at least 50% for at least 3 wash cycles.
  • the laundry or cleaning composition exhibits color maintenance or color wash fastness of about 95% to about 99 % for 3 wash cycles [0090] It has been advantegeously found that the reaction of guanidine salts with glyoxal leads to the formation of guanidine derivatives i.e. the compounds of Formula (I) and Formula (II). These compounds not only form dye complexes in the detergent solution, but also are capable of adsorbing at the interfaces of colored and white fabrics. These derivatives have thus a dual effect, namely, they protect against dye transfer and against dye bleeding.
  • the present approach to color protection is in sharp contrast to what is described in the current state of the art wherein the effective dye transfer inhibition is mainly accomplished when the dissolved dye in the wash liquor is captured by complexation.
  • the laundry or cleaning composition according to the present disclosure rather inhibits the dye transfer at three different connected stages, namely, (i) dye desorption from colored articles into the detergent solution; (ii) dye dissolution into the detergent solution; and (iii) adsorption/diffusion of the dissolved dye from the detergent solution onto white and other light-colored articles.
  • the laundry and cleaning composition of the present disclosure not only form dye-complexes in the detergent solution but also are capable of absorbing and forming complexes with the dye molecules at the article interface.
  • the laundry and cleaning composition of the present disclosure results not only in effective dye transfer inhibition but also results in efficient color protection in the form of dye anti-bleeding from colored articles.
  • the following examples illustrate the presently disclosed and/or claimed inventive concept(s), parts and percentages being by weight, unless otherwise indicated. Each example is provided by way of explanation of the presently disclosed and/or claimed inventive concept(s), not limitation of the presently disclosed and/or claimed inventive concept(s). In fact, it will be apparent to those skilled in the art that various modifications and variations can be made in the presently disclosed and/or claimed inventive concept(s) without departing from the scope or spirit of the invention. For instance, features illustrated or described as part of one embodiment, can be used on another embodiment to yield a still further embodiment.
  • EXAMPLE 2 Synthesis of Compounds of Formula (I) and Formula (II) with Sodium Hydroxide as Neutralization Agent (Liquid Form) [0093] 200g of water and 50g of Guanidine HCl (CAS #50-01-1) were mixed in a 500mL 3 necked round bottom flask equipped with a heating mantle, a mechanical stirrer and a thermocouple to obtain a solution. The solution was heated to 38 °C under continuous stirring at 200 rpm. To this solution, 75.9g solution of Glyoxal (40% solids in water) (CAS #107-22- 2) was added. Afterwards, 11g of sodium hydroxide (CAS# 1310-73-2) was added.
  • the obtained reaction mixture was then stirred for 60 minutes during which the color of the reaction mixture changed from light yellow to amber to burgundy.50g of ammonium persulfate (CAS # 7727-54-0) was then added to the reaction mixture under continuous stirring. The stirring of the reaction mixture was continued for 15 minutes. Afterwards, 30 wt.% of hydrogen peroxide (CAS# 7722-84-1; 75g) was added to the reaction mixture. The resultant reaction mixture thus obtained was heated to 50 °C while stirring for 60 minutes. The burgundy color of the resultant mixture changed to light amber color during this step. The final product was discharged.
  • EXAMPLE 3A Synthesis of Compounds of Formula (I) and Formula (II) (Solid Form using Silica) [0094] 30g of Silica (Sipernat50) was placed in a mixing bowl of an electric kitchen mixer and stirred on the slowest speed. The final product of Example 1 (liquid form) was filtered and neutralized to a pH of 5-6 with Sodium hydroxide. 70g of the filtered and neutralized product solution thus obtained was slowly added to the silica under continuous stirring. The mixing of the silica and the filtered and neutralized product solution was carried out until a free-flowing powder was obtained.
  • EXAMPLE 3C Synthesis of Compounds of Formula (I) and Formula (II) (Precipitated Solid Form) [0096] The filtered and neutralized product solution obtained from the final product of Example 1 was added to excess acetone to induce precipitation of the active ingredients (compounds of Formula (I) and Formula (II). The supernatant liquid from the precipitation process was removed by decantation and the precipitated solid was extracted and dried under vacuum at room temperature to obtain a pale-yellow powder of compounds of Formula (I) and Formula (II) without any silica.
  • EXAMPLE 4 Preparation of prototype laundry detergent composition [0097] 25% active surfactants in detergent formulation containing a 2:1 ratio of anionic: nonionic surfactants commonly used in detergent chassis was prepared by mixing the ingredients listed in Table 1. Once all the components in the Table 1 were thoroughly mixed to yield a clear solution, the pH of the prototype detergent was adjusted to 8.85 by dropwise addition of Aminomethyl propanol (AMP Ultra PC 2000, Angus Chemical Company). This detergent was used in following laundry applications. TABLE 1: Prototype Laundry Detergent Composition EXAMPLE 5: Dye-transfer inhibition performance of solid and liquid compositions of Examples 1, 2, 3A, 3B and 3C; and Dye-transfer inhibition dose response of solid composition vs commercial benchmark.
  • each bin of the Tergotometer contained a total of 7 pieces of fabric (2 donor + 5 acceptors).
  • each bin of the Tergotometer was charged with 2 donor fabrics and 5 separate acceptor fabrics as mentioned above.
  • the laundry liquid prepared by diluting prototype detergent, and hard water with or without dye transfer inhibitors was charged into each designated bin of the Tergotometer. Laundry cycle was carried out for 60 minutes at 50 o C with 75 RPM agitation.

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Abstract

L'invention concerne une composition comprenant des composés de guanidine. L'invention concerne également une composition de blanchisserie ou de nettoyage comprenant les composés de guanidine, la composition empêchant l'exsudation de colorant d'articles colorés et empêchant également le transfert de colorant d'articles colorés à un autre co-article ou au même article pendant le blanchissage.
PCT/US2022/039094 2021-08-04 2022-08-01 Compositions comprenant des composés de guanidine, leur procédé de préparation et leurs procédés d'utilisation Ceased WO2023014672A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6103899A (en) * 1993-04-08 2000-08-15 The Trustees Of Columbia University In The City Of New York Bicyclic aminoimidazoles
US20160176878A1 (en) * 2014-09-29 2016-06-23 U.S. Army Research Laboratory Attn: Rdrl-Loc-I Novel preparation of tetranitroglycoluril

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6103899A (en) * 1993-04-08 2000-08-15 The Trustees Of Columbia University In The City Of New York Bicyclic aminoimidazoles
US20160176878A1 (en) * 2014-09-29 2016-06-23 U.S. Army Research Laboratory Attn: Rdrl-Loc-I Novel preparation of tetranitroglycoluril

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MCCLELLAND ROBERT A., PANICUCCI RICK, RAUTH A. MICHAEL: "Products of reductions of 2-nitroimidazoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 109, no. 14, 1 July 1987 (1987-07-01), pages 4308 - 4314, XP093033744, ISSN: 0002-7863, DOI: 10.1021/ja00248a028 *
R. PANICUCCI ET AL.: "4,5-Dihydro-4,5-dihydroxyimidazoles as products of the reduction of 2-nitroimidazoles, Hplc assay and demaonstration of equilibrium trasfer of glyoxal to guanine", CANADIAN JOURNAL OF CHEMISTRY, NRC RESEARCH PRESS, CA, vol. 67., 1 January 1989 (1989-01-01), CA , pages 2128 - 2135., XP002117469, ISSN: 0008-4042, DOI: 10.1139/v89-331 *

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