WO2015095046A1 - Use of poly alpha-1,3-glucan ethers as viscosity modifiers - Google Patents

Use of poly alpha-1,3-glucan ethers as viscosity modifiers Download PDF

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Publication number
WO2015095046A1
WO2015095046A1 PCT/US2014/070341 US2014070341W WO2015095046A1 WO 2015095046 A1 WO2015095046 A1 WO 2015095046A1 US 2014070341 W US2014070341 W US 2014070341W WO 2015095046 A1 WO2015095046 A1 WO 2015095046A1
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WO
WIPO (PCT)
Prior art keywords
glucan
poly alpha
poly
viscosity
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2014/070341
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English (en)
French (fr)
Inventor
Rahul B. Kasat
Jayme L. Paullin
Andrea M. Perticone
T. Joseph Dennes
Rakesh NAMBIAR
Michael W. Cobb
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Priority to CN201480075648.3A priority Critical patent/CN106255707B/zh
Priority to BR112016013684A priority patent/BR112016013684A2/pt
Priority to AU2014366222A priority patent/AU2014366222B2/en
Priority to MX2016007759A priority patent/MX373205B/es
Priority to CA2932498A priority patent/CA2932498C/en
Priority to EP22190123.4A priority patent/EP4163305B1/en
Priority to JP2016539973A priority patent/JP6598778B2/ja
Priority to US15/103,664 priority patent/US10005850B2/en
Priority to KR1020167018848A priority patent/KR20160099629A/ko
Priority to EP14822009.8A priority patent/EP3083704B1/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO2015095046A1 publication Critical patent/WO2015095046A1/en
Anticipated expiration legal-status Critical
Priority to US16/007,287 priority patent/US10865254B2/en
Priority to US17/118,754 priority patent/US11958916B2/en
Priority to US17/667,707 priority patent/US12091470B2/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • U.S. Patent 7,000,000 disclosed the preparation of a polysaccharide fiber comprising hexose units, wherein at least 50% of the hexose units within the polymer were linked via aipha-1 ,3-glycosidic linkages using an S. salivarius gtfJ enzyme.
  • This enzyme utilizes sucrose as a substrate in a polymerization reaction producing poly alpha-1 ,3-giucan and fructose as end-products (Simpson et aL, 1995).
  • the disclosed polymer formed a liquid crystalline solution when it was dissolved above a critical concentration in a solvent or in a mixture comprising a solvent. From this solution continuous, strong, cotton-like fibers, highly suitable for use in textiles, were spun and used.
  • CMG CMG
  • This ether derivative exhibited anti-tumor properties against sarcoma.
  • Zhang et al. (Intl. PubL No. CN1283633) described the extraction of poly alpha-1 ,3-giucan from the medicinal fungus, Ganoderma lucidum, and its derivafization to CMG.
  • the compound has a degree of substitution of about 0.05 to about 3.0, and
  • At least one organic group is selected from the group consisting of alkyi group, hydroxy alkyl group, and carboxy alkyl group.
  • the compound in this embodiment may contain one type of organic group, or two or more types of organic group. At least one organic group is selected from the group consisting of carboxymethyi, methyl, ethyl, hydroxypropyl, dihydroxypropyi, and hydroxyethyi group, for example.
  • the compound contains one type of organic group, whereas the compound contains two or more types of organic group in a fourth embodiment.
  • the poly alpha-1 ,3-glucan ether compound is crossiinked.
  • the pH of the hydrocol!oid or aqueous solution is between about 2.0 to about 12.0.
  • the invention concerns a method of treating a material.
  • This method comprises contacting a material with an aqueous composition comprising a poly alpha-1 ,3-glucan ether compound as disclosed herein.
  • the poly alpha-1 ,3-glucan ether compound adsorbs to the surface of the material in certain embodiments of this method.
  • Poly alpha-1 , 3-giucan used to produce poly alpha-1 , 3-giucan ether compounds herein is preferably linear/unbranched.
  • poly alpha-1 ,3-glucan has no branch points or less than about 10%, 9%, 8%, 7%, 8%, 5%, 4%, 3%, 2%, or 1 % branch points as a percent of the giycosidic linkages in the polymer.
  • branch points include alpha-1 , 6 branch points, such as those present in mutan polymer.
  • alpha-1.3-g!ycosidic linkage refers to the type of covalent bond that joins alpha-D-glucose molecules to each other through carbons 1 and 3 on adjacent alpha-D-glucose rings. This linkage is illustrated in the poly alpha-1 , 3-giucan structure provided above.
  • alpha-D-glucose will be referred to as "glucose”.
  • An etherification agent herein refers to an agent that can be used to etherify one or more hydroxyl groups of one or more glucose units of poly alpha-1 ,3-giucan with an organic group.
  • An etherification agent thus comprises an organic group.
  • the term "poly alpha-1 ,3-giucan slurry" herein refers io an aqueous mixture comprising the components of a g!ucosyitransferase enzymatic reaction such as poly alpha-1 ,3-glucan, sucrose, one or more glucosyltransferase enzymes, glucose and fructose. This composition is a slurr since the poly alpha ⁇ 1 ,3-giucan is not dissolved therein.
  • adsorption herein refers to the adhesion of a compound (e.g., poly aipha-1 ,3-giucan ether) to the surface of a material.
  • these terms refer to a greater quantity or activity such as a quantity or activity slightly greater than the original quantity or activity, or a quantity or activity in large excess compared to the original quantify or activity, and including all quantities or activities in between.
  • these terms may refer to, for example, a quantity or activity that is at least 1 %, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 125%, 150%, 175%, or 200% (or any integer between 1 % and 200%) more than the quantity or activity for which the increased quantity or activity is being compared.
  • substitution(s) may be one or more hydroxyl, aldehyde, ketone, and/or carboxyl groups.
  • a substituted alkyl group may be a hydroxy alkyl group, dihydroxy alkyl group, or carboxy alkyl group.
  • Non-limiting examples of food products herein include vegetable, meat, and soy patties; reformed seafood; reformed cheese sticks; cream soups;
  • a detergent composition herein can comprise 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-viny!pyrrolidone and N-vinylimidazoie, poiyvinyioxazolidones and po!yviny!imidazoies or mixtures thereof.
  • hyaiuronidases keratinases, lactases, ligninases, peroxidases, phosphatases, polygalacturonases, pulluianases, rhamnoga!actouronases, tannases,
  • the detergent in some embodiments of the present invention, the detergent
  • Enzymes that may be comprised in a detergent composition herein may be stabilized using conventional stabilizing agents, e.g., a polyoi such as propylene glycol or glycerol; a sugar or sugar alcohol; lactic acid; boric acid or a boric acid derivative (e.g., an aromatic borate ester).
  • a polyoi such as propylene glycol or glycerol
  • a sugar or sugar alcohol lactic acid
  • boric acid or a boric acid derivative e.g., an aromatic borate ester
  • a detergent composition formulated as a granulate having a bulk density of at least 800 g/L comprising: fatty alcohol sulfate at about 5-10 wt%, ethoxylated fatty acid monoethanoiamide at about 3-9 wt%; soap as fatty acid at about 0-3 wt%; sodium carbonate at about 5-10 wt%; soluble silicate (e.g., Na 2 0 2Si0 2 ) at about 1 -4 wt%; zeolite (e.g., NaAISi0 4 ) at about 20-40 wt%; sodium sulfate at about 2-8 wt%; sodium perborate at about 12-18 wt%; TAED at about 2-7 wt%; poly alpha-1 ,3-glucan ether (e.g.
  • nonionic surfactant e.g., alcohol ethoxylate
  • Examples of etherification agents for producing propyl poly a!pha-1 ,3-glucan ethers include dipropyl sulfate, dipropyl carbonate, propyl chloride, iodopropane, propyl triflate and propyl f!uorosulfonate.
  • Examples of etherification agents for producing butyl poly alpha-1 ,3-glucan ethers include dibutyi sulfate, dibuty! carbonate, butyl chloride, iodobutane and butyl triflate.
  • Etherification agents suitable for preparing a dibydroxyaikyi poly alpha- 1 ,3-g!ucan ether compound include dihydroxyaikyl halides (e.g., dihydroxyalkyl chloride) such as dihydroxyethyi halide, dihydroxypropyl halide (e.g., 2,3- dihydroxypropyl chloride [i.e., 3-chloro-1 ,2-propanediol]), or dihydroxybutyl halide, for example.
  • dihydroxyaikyl halides e.g., dihydroxyalkyl chloride
  • dihydroxypropyl halide e.g., 2,3- dihydroxypropyl chloride [i.e., 3-chloro-1 ,2-propanediol]
  • 2,3-dihydroxypropyi chloride can be used to prepare dihydroxypropyl poly alpha-1 ,3-glucan, for example.
  • the pH of the solution or mixture containing both a crosslinking agent(s) and a poly alpha-1 ,3-glucan ether compound(s) can be adjusted to be alkali (e.g., pH of 8, 8.5, 9, 9.5, or 10). Modification of pH can be done by any means known in the art, such as with a concentrated aqueous solution of an alkali hydroxide such as sodium hydroxide. Dissolving a crosslinking agent in a solution or mixture containing one or more poly alpha-1 ,3-giucan ether compounds at an alkali pH results in crosslinking of the poly alpha-1 .3-g!ucan ether compound(s).
  • Poly aipha-1 ,3-giucan is added to an aliquot of a substance such as isopropanol or toluene in a 400-mL capacity shaker tube, after which sodium hydroxide (1 -70% solution) is added. This preparation is stirred for up to 48 hours. Then, sodium monochloroacetate is added to provide a reaction, which is then heated to 25-100 °C for up to 14 days. Propylene oxide is then added to the reaction, which is then heated to 25-100 °C for up to 14 days before being neutralized with acid (e.g., acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried. Thus, the glucan ether derivative, sodium carboxymethyl hydroxypropyl poly alpha-1 ,3-giucan, is prepared and isolated.
  • sodium hydroxide (1 -70% solution
  • CMG solutions where the solutions were prepared using CMG with different molecular weights. It is shown that CMG solutions exhibit significant shear thinning behavior. Thus, addition of CMG to a liquid can modify the rheologicai behavior of the liquid.

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PCT/US2014/070341 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers Ceased WO2015095046A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
KR1020167018848A KR20160099629A (ko) 2013-12-16 2014-12-15 점도 조절제로서의 폴리 알파-1,3-글루칸 에테르의 사용
AU2014366222A AU2014366222B2 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
MX2016007759A MX373205B (es) 2013-12-16 2014-12-15 Uso de eteres de poli-alfa-1,3-glucano como modificadores de la viscosidad.
CA2932498A CA2932498C (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
EP22190123.4A EP4163305B1 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
JP2016539973A JP6598778B2 (ja) 2013-12-16 2014-12-15 ポリα−１，３−グルカンエーテル化合物を含む洗濯洗剤又は衣類柔軟剤
US15/103,664 US10005850B2 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
CN201480075648.3A CN106255707B (zh) 2013-12-16 2014-12-15 聚α-1，3-葡聚糖醚类作为粘度调节剂的用途
BR112016013684A BR112016013684A2 (pt) 2013-12-16 2014-12-15 Solução aquosa ou hidrocoloide, método para aumentar a viscosidade de uma composição e método para o tratamento de um material
EP14822009.8A EP3083704B1 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
US16/007,287 US10865254B2 (en) 2013-12-16 2018-06-13 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
US17/118,754 US11958916B2 (en) 2013-12-16 2020-12-11 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
US17/667,707 US12091470B2 (en) 2013-12-16 2022-02-09 Use of poly alpha-1,3-glucan ethers as viscosity modifiers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361916360P 2013-12-16 2013-12-16
US61/916,360 2013-12-16
US201462014271P 2014-06-19 2014-06-19
US62/014,271 2014-06-19

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US15/103,664 A-371-Of-International US10005850B2 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers
US16/007,287 Continuation US10865254B2 (en) 2013-12-16 2018-06-13 Use of poly alpha-1,3-glucan ethers as viscosity modifiers

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WO2015095046A1 true WO2015095046A1 (en) 2015-06-25

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PCT/US2014/070341 Ceased WO2015095046A1 (en) 2013-12-16 2014-12-15 Use of poly alpha-1,3-glucan ethers as viscosity modifiers

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US (4) US10005850B2 (https=)
EP (2) EP3083704B1 (https=)
JP (1) JP6598778B2 (https=)
KR (1) KR20160099629A (https=)
CN (1) CN106255707B (https=)
AU (1) AU2014366222B2 (https=)
BR (1) BR112016013684A2 (https=)
CA (1) CA2932498C (https=)
MX (1) MX373205B (https=)
WO (1) WO2015095046A1 (https=)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015195960A1 (en) * 2014-06-19 2015-12-23 E. I. Du Pont De Nemours And Company Compositions containing one or more poly alpha-1,3-glucan ether compounds
WO2015195777A1 (en) * 2014-06-19 2015-12-23 E. I. Du Pont De Nemours And Company Compositions containing one or more poly alpha-1,3-glucan ether compounds
WO2016106068A1 (en) * 2014-12-22 2016-06-30 E. I. Du Pont De Nemours And Company Polymeric blend containing poly alpha-1,3-glucan
WO2016196021A1 (en) * 2015-06-01 2016-12-08 E I Du Pont De Nemours And Company Structured liquid compositions comprising colloidal dispersions of poly alpha-1,3-glucan
AT518612A1 (de) * 2015-02-06 2017-11-15 Chemiefaser Lenzing Ag Polysaccharid-Suspension, Verfahren zu ihrer Herstellung und ihre Verwendung
US9957334B2 (en) 2013-12-18 2018-05-01 E I Du Pont De Nemours And Company Cationic poly alpha-1,3-glucan ethers
US10005850B2 (en) 2013-12-16 2018-06-26 E I Du Pont De Nemours And Company Use of poly alpha-1,3-glucan ethers as viscosity modifiers
KR20180072709A (ko) * 2015-10-26 2018-06-29 이 아이 듀폰 디 네모아 앤드 캄파니 종이용 다당류 코팅
US10059778B2 (en) 2014-01-06 2018-08-28 E I Du Pont De Nemours And Company Production of poly alpha-1,3-glucan films
US10106626B2 (en) 2014-01-17 2018-10-23 Ei Du Pont De Nemours And Company Production of poly alpha-1,3-glucan formate films
JP2019501044A (ja) * 2015-10-26 2019-01-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 水不溶性α−（１，３→グルカン）組成物
JP2019502032A (ja) * 2015-11-13 2019-01-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物
JP2019502831A (ja) * 2015-11-13 2019-01-31 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物
KR20190018640A (ko) * 2016-06-13 2019-02-25 이 아이 듀폰 디 네모아 앤드 캄파니 세제 조성물
WO2019050750A1 (en) * 2017-09-11 2019-03-14 E. I. Du Pont De Nemours And Company POLY (ALPHA-1,3-GLUCAN) COMPOUNDS
CN109983067A (zh) * 2016-11-16 2019-07-05 纳幕尔杜邦公司 纤维素/多糖复合材料
JP2020041150A (ja) * 2016-12-16 2020-03-19 デュポン・インダストリアル・バイオサイエンシーズ・ユーエスエイ・エルエルシー 両親媒性多糖誘導体及びそれを含む組成物
US10822574B2 (en) 2015-11-13 2020-11-03 Dupont Industrial Biosciences Usa, Llc Glucan fiber compositions for use in laundry care and fabric care
US10895028B2 (en) 2015-12-14 2021-01-19 Dupont Industrial Biosciences Usa, Llc Nonwoven glucan webs
US11351104B2 (en) 2015-02-06 2022-06-07 Nutrition & Biosciences USA 4, Inc. Colloidal dispersions of poly alpha-1,3-glucan based polymers

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