WO2008084093A2 - Particles comprising active compounds - Google Patents
Particles comprising active compounds Download PDFInfo
- Publication number
- WO2008084093A2 WO2008084093A2 PCT/EP2008/050285 EP2008050285W WO2008084093A2 WO 2008084093 A2 WO2008084093 A2 WO 2008084093A2 EP 2008050285 W EP2008050285 W EP 2008050285W WO 2008084093 A2 WO2008084093 A2 WO 2008084093A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- particle
- enzyme
- particles
- modified
- 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
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
- C11D3/16—Organic compounds
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/386—Preparations containing enzymes, e.g. protease or amylase
- C11D3/38672—Granulated or coated enzymes
-
- 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
-
- 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
- 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
- C11D3/37—Polymers
-
- 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
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3776—Heterocyclic compounds, e.g. lactam
Definitions
- One object of the present invention is to provide particles comprising proteins in particular enzymes, with improved storage stability, for liquid compositions such as liquid detergents. It has surprisingly been found that it is possible to improve the storage stability of proteins such as enzymes by preparing polymer matrix particles comprising the enzyme.
- Hydrophilic polymers may include but are not limited to polyvinylpyrrolidone, polyvinylalcohol, polyethyleneglycol, hydroxypropylcellulose, hydroxymethylcellulose, hydroxypropylmethylcellu- lose, gelatin, polyvinylmethylether, polymethyloxazoline, polyethyloxazoline, polyhydroxypropy- loxazoline, carrageenan, polyhydroxypropylmethacrylamide, polymethacrylamide, polydimethy- lacrylamide, polyhydroxypropylmethacrylate, polyhydroxyethylacrylate, hydroxymethylcellulose, hydroxyethylcellulose, polyethyleneglycol, polyaspartamide, polyethyleneoxide (PEO), and polysaccharides.
- PEO polyethyleneoxide
- the modified polymer may be selected from but is not limited to the group consisting of a hydrophobically modified polyvinyl pyrrolidone (PVP), hydrophobically modified polyvinyl alcohol (PVA), hydrophobically modified cellulose derivatives such as carboxymethyl cellulose, methyl cellulose and/or hydroxypropyl cellulose, car- rageenan, gum such as guar gum, gum benzoin, gum tragacanth, gum arabic and/or gum acacia, protein such as casein, gelatin and/or albumin.
- PVP polyvinyl pyrrolidone
- PVA hydrophobically modified polyvinyl alcohol
- cellulose derivatives such as carboxymethyl cellulose, methyl cellulose and/or hydroxypropyl cellulose, car- rageenan
- gum such as guar gum, gum benzoin, gum tragacanth, gum arabic and/or gum acacia
- protein such as casein, gelatin and/or albumin.
- the mole percent of monomer in the copolymer is as follows: about 10 to less than 50 mole percent cationic monomer; and greater than 50 to about 90 mole percent water insoluble, hydrophobic monomer. More specifically, the mole percent of monomers in the copolymer is from about 15 to about 25 mole percent cationic monomer; and from about 70 to about 85 mole percent water insoluble, hydrophobic monomer. Most specifically, the mole per- cent of monomers in the copolymer is from about 20 mole percent cationic monomer; and about 80 mole percent water insoluble, hydrophobic monomer.
- Suitable laccases herein include those of bacterial or fungal origin. Chemically or genetically modified mutants are included. Examples of suitable laccases are those obtainable from a strain of Trametes, e.g., T. villosa or T. versicolor, or from a strain of Coprinus, e.g., C. cinereus, or from a strain of Myceliophthora, e.g., M. thermophila.
- transglutaminases are described in WO 96/06931 (Novo Nordisk
- Poly ethylene glycols PEG.
- PEG waxes are commercially available having different molecular sizes, wherein PEG'S with low molecular sizes also have low melting points.
- suitable PEG'S are PEG 1500, PEG 2000, PEG 3000, PEG 4000, PEG 6000, PEG 8000, PEG 9000 etc. e.g. from BASF (Pluriol E series) or from Clariant or from Ineos.
- Derivatives of Poly ethylene glycols may also be used, polypropylene (e.g. polypropylen glycol Pluriol P series from BASF) or polyethylene or mixtures thereof. Derivatives of polypropylenes and polyethylenes may also be used.
- the particles of the present invention may comprise one, two or more additional coating layers.
- Emulsion process wherein an aqueous liquid enzyme containing solution is emulsified in a water immiscible liquid e.g. paraffinic oil.
- a water immiscible liquid e.g. paraffinic oil.
- various emulsifiers and surfactants are used.
- the water from the droplet can subsequently be removed be distilliation, e.g. azeotropic distillation, or by spray drying the emulsion if the water immiscible liquid is volatile.
- the liquid composition is a liquid detergent composition
- the liquid composition may comprise a surfactant desolubilising electrolyte, said electrolyte being present in a concentration at which said surfactant forms a structure capable of stably suspending the enzyme/polymer particles and sufficient to prevent or inhibit dissolution of the water soluble polymer.
- Other less preferred builders include potassium or lithium analogues of the above sodium salts.
- the proportion of builder is typically from about 5% to about 40% by weight of the liquid detergent composition. Usually 10% to 35%, preferably 15-30%, more preferably 18 to 28%, most preferably 20 to 27%.
- Mixtures of two or more builders are often employed, e.g. sodium tripolyphosphate with sodium silicate and/or sodium carbonate and/or with zeolite; or sodium nitrilotriacetate with sodium citrate.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08701429A EP2129757A2 (en) | 2007-01-11 | 2008-01-11 | Particles comprising active compounds |
| CN200880008046.0A CN101636480B (zh) | 2007-01-11 | 2008-01-11 | 包含活性化合物的颗粒 |
| US12/521,658 US20100323945A1 (en) | 2007-01-11 | 2008-01-11 | Particles Comprising Active Compounds |
| JP2009545185A JP5209643B2 (ja) | 2007-01-11 | 2008-01-11 | 活性化合物を含む粒子 |
| US13/343,161 US9499773B2 (en) | 2007-01-11 | 2012-01-04 | Enzyme particles comprising a vinyl pyrrolidone/vinyl acetate copolymer |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200700039 | 2007-01-11 | ||
| DKPA200700039 | 2007-01-11 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/521,658 A-371-Of-International US20100323945A1 (en) | 2007-01-11 | 2008-01-11 | Particles Comprising Active Compounds |
| US13/343,161 Continuation US9499773B2 (en) | 2007-01-11 | 2012-01-04 | Enzyme particles comprising a vinyl pyrrolidone/vinyl acetate copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2008084093A2 true WO2008084093A2 (en) | 2008-07-17 |
| WO2008084093A3 WO2008084093A3 (en) | 2009-01-08 |
Family
ID=38055380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2008/050285 Ceased WO2008084093A2 (en) | 2007-01-11 | 2008-01-11 | Particles comprising active compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20100323945A1 (enExample) |
| EP (1) | EP2129757A2 (enExample) |
| JP (1) | JP5209643B2 (enExample) |
| CN (1) | CN101636480B (enExample) |
| WO (1) | WO2008084093A2 (enExample) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101724621A (zh) * | 2009-12-17 | 2010-06-09 | 北京凯泰新世纪生物技术有限公司 | 一种微载体固定化脂肪酶及其制备方法 |
| WO2012140421A1 (en) * | 2011-04-15 | 2012-10-18 | Reckitt & Colman (Overseas) Limited | Novel composite |
| WO2012140442A1 (en) * | 2011-04-15 | 2012-10-18 | Revolymer Limited | Particles with hydroxyl vinylic copolymer coating sensitive to ionic strength |
| WO2015177077A1 (en) * | 2014-05-22 | 2015-11-26 | Unilever Plc | Aqueous liquid detergent formulation comprising enzyme particles |
| WO2016023685A1 (en) * | 2014-08-11 | 2016-02-18 | Novozymes A/S | Detergents and compositions with enzymatic polymer particles |
| US20160075976A1 (en) * | 2013-05-03 | 2016-03-17 | Novozymes A/S | Microencapsulation of Detergent Enzymes |
| EP3173467A1 (en) * | 2015-11-26 | 2017-05-31 | The Procter & Gamble Company | Cleaning compositions comprising enzymes |
| EP3243898A2 (en) | 2016-05-09 | 2017-11-15 | The Procter & Gamble Company | Detergent composition comprising an oleic acid-transforming enzyme |
| EP3243896A1 (en) | 2016-05-09 | 2017-11-15 | The Procter and Gamble Company | Detergent composition comprising a fatty acid decarboxylase |
| EP3243897A1 (en) | 2016-05-09 | 2017-11-15 | The Procter & Gamble Company | Detergent composition comprising a fatty acid-transforming enzyme |
| CN109490274A (zh) * | 2019-01-04 | 2019-03-19 | 齐鲁工业大学 | 一种用于研究酶在皮革中单向传质的实验装置及使用方法 |
| EP2350250B2 (en) † | 2008-11-03 | 2022-11-30 | Danisco US Inc. | Delivery system for co-formulated enzyme and substrate |
| EP3511404B1 (de) | 2014-06-30 | 2024-12-18 | Henkel AG & Co. KGaA | Flüssiges reinigungsmittel enthaltend flüssige und feste enzymformulierungen |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2674475A1 (en) * | 2012-06-11 | 2013-12-18 | The Procter & Gamble Company | Detergent composition |
| IN2015KN00664A (enExample) * | 2012-09-24 | 2015-07-17 | Firmenich & Cie | |
| AU2014324916B2 (en) | 2013-09-27 | 2018-06-14 | Rohm And Haas Company | Ionic strength triggered disintegration of films and particulates |
| WO2015048266A1 (en) | 2013-09-27 | 2015-04-02 | Rohm And Haas Chemicals Llc | Water dispersible films for packaging high water containing formulations |
| US20150320033A1 (en) * | 2014-05-12 | 2015-11-12 | Thomas Michael Schultz | Pre-Emergent Seed Coatings and Growth Stimulator Compositions |
| EP3446665B1 (en) | 2014-10-06 | 2021-12-15 | 3M Innovative Properties Company | Ion exchange absorbent systems, apparatuses |
| CN107896481B (zh) * | 2015-05-18 | 2021-07-06 | 齐姆特罗尼克斯公司 | 磁力固定化的杀微生物酶 |
| EP3307427B1 (en) * | 2015-06-09 | 2023-08-16 | Danisco US Inc. | Osmotic burst encapsulates |
| CN108140848B (zh) | 2015-07-15 | 2022-02-01 | 齐姆特罗尼克斯公司 | 自动化生物纳米催化剂生产 |
| US12127557B2 (en) | 2016-08-13 | 2024-10-29 | Zymtronix Catalytic Systems, Inc. | Magnetically immobilized biocidal enzymes and biocidal chemicals |
| CN108148827B (zh) * | 2016-12-02 | 2022-09-23 | 丰益(上海)生物技术研发中心有限公司 | 固定化酶及其制备方法和用途 |
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| GB1390503A (en) | 1971-03-30 | 1975-04-16 | Unilever Ltd | Liquid detergent compositions |
| US3860484A (en) * | 1972-09-28 | 1975-01-14 | Xerox Corp | Enzyme stabilization |
| JPS5113387A (enExample) | 1974-07-24 | 1976-02-02 | Fuji Photo Film Co Ltd | |
| US4411999A (en) * | 1981-09-29 | 1983-10-25 | Denki Kagaku Kogyo Kabushiki Kaisha | Immobilization of enzymes on granular gelatin |
| DK149079C (da) * | 1982-10-06 | 1986-06-23 | Novo Industri As | Fremgangsmaade til fremstilling af et immobiliseret enzympraeparat |
| US4777089A (en) | 1985-05-08 | 1988-10-11 | Lion Corporation | Microcapsule containing hydrous composition |
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| US5093021A (en) * | 1985-08-21 | 1992-03-03 | The Clorox Company | Encapsulated enzyme in dry bleach composition |
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| DK171065B1 (da) * | 1988-08-24 | 1996-05-13 | Allied Colloids Ltd | Flydende enzym-holdig sammensætning og fremgangsmåde til fremstilling af samme |
| JP3162696B2 (ja) | 1989-09-06 | 2001-05-08 | ライオン株式会社 | 水溶性で塩感応性のポリマー |
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| CN1135265C (zh) * | 1996-04-12 | 2004-01-21 | 诺沃奇梅兹有限公司 | 含酶颗粒及其生产方法 |
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| CN1192087C (zh) * | 1998-06-30 | 2005-03-09 | 诺沃奇梅兹有限公司 | 一种新的改进的含酶颗粒 |
| US6268329B1 (en) * | 1998-06-30 | 2001-07-31 | Nouozymes A/S | Enzyme containing granule |
| ES2355123T3 (es) * | 1998-11-13 | 2011-03-23 | Danisco Us Inc. | Gránulo de baja densidad en lecho fluidizado. |
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| DE60026970T2 (de) * | 1999-01-08 | 2006-11-30 | Genencor International, Inc., Palo Alto | Zusammensetzungen mit niedriger dichte und partikeln der diese enthalten |
| EP1224273B1 (en) * | 1999-10-01 | 2007-10-17 | Novozymes A/S | Enzyme granulate |
| US6933141B1 (en) * | 1999-10-01 | 2005-08-23 | Novozymes A/S | Enzyme granulate |
| JP2004512423A (ja) * | 2000-10-27 | 2004-04-22 | ジェネンコア インターナショナル インコーポレーテッド | 置換されたポリビニルアルコール塗膜を有する粒子 |
| US7070854B2 (en) | 2001-03-22 | 2006-07-04 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| GB2374082A (en) * | 2001-04-04 | 2002-10-09 | Procter & Gamble | Particles for a detergent product |
| DE10127526A1 (de) * | 2001-05-31 | 2002-12-12 | Novosom Ag | Verfahren zur Herstellung und Auflösung von Nano- und Mikrokapseln |
| ES2295359T3 (es) * | 2001-06-22 | 2008-04-16 | Genencor International, Inc. | Granulos de alta resistencia al impacto. |
| DE10142124A1 (de) * | 2001-08-30 | 2003-03-27 | Henkel Kgaa | Umhüllte Wirkstoffzubereitung für den Einsatz in teilchenförmigen Wasch- und Reinigungsmitteln |
| AU2003243926A1 (en) * | 2002-07-01 | 2004-01-19 | Novozymes A/S | Stabilization of granules |
| US20040229329A1 (en) * | 2002-12-24 | 2004-11-18 | Becker Nathaniel T. | Mechanically robust plasticized granules |
| WO2005063365A1 (en) | 2003-12-31 | 2005-07-14 | Council Of Scientific And Industrial Research | A process for the preparation of free standing membranes |
| DE102004021384A1 (de) * | 2004-04-30 | 2005-11-24 | Henkel Kgaa | Verfahren zur Herstellung von Granulaten mit verbesserter Lagerstabilität und Abriebfestigkeit |
| US20090163398A1 (en) * | 2005-11-16 | 2009-06-25 | Kao Corporation | Composite particle |
| DE102006018780A1 (de) * | 2006-04-20 | 2007-10-25 | Henkel Kgaa | Granulat eines sensitiven Wasch- oder Reinigungsmittelinhaltsstoffs |
| WO2010003934A1 (en) | 2008-07-07 | 2010-01-14 | Basf Se | Enzyme composition comprising enzyme containing polymer particles |
-
2008
- 2008-01-11 WO PCT/EP2008/050285 patent/WO2008084093A2/en not_active Ceased
- 2008-01-11 CN CN200880008046.0A patent/CN101636480B/zh not_active Expired - Fee Related
- 2008-01-11 EP EP08701429A patent/EP2129757A2/en not_active Ceased
- 2008-01-11 JP JP2009545185A patent/JP5209643B2/ja not_active Expired - Fee Related
- 2008-01-11 US US12/521,658 patent/US20100323945A1/en not_active Abandoned
-
2012
- 2012-01-04 US US13/343,161 patent/US9499773B2/en not_active Expired - Fee Related
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2350250B2 (en) † | 2008-11-03 | 2022-11-30 | Danisco US Inc. | Delivery system for co-formulated enzyme and substrate |
| CN101724621A (zh) * | 2009-12-17 | 2010-06-09 | 北京凯泰新世纪生物技术有限公司 | 一种微载体固定化脂肪酶及其制备方法 |
| WO2012140421A1 (en) * | 2011-04-15 | 2012-10-18 | Reckitt & Colman (Overseas) Limited | Novel composite |
| WO2012140442A1 (en) * | 2011-04-15 | 2012-10-18 | Revolymer Limited | Particles with hydroxyl vinylic copolymer coating sensitive to ionic strength |
| US20140171327A1 (en) * | 2011-04-15 | 2014-06-19 | Revolymer (U.K.) Limited | Novel composite |
| US20160075976A1 (en) * | 2013-05-03 | 2016-03-17 | Novozymes A/S | Microencapsulation of Detergent Enzymes |
| CN106488972B (zh) * | 2014-05-22 | 2020-05-05 | 荷兰联合利华有限公司 | 包含酶颗粒的水性液体洗涤剂制剂 |
| CN106488972A (zh) * | 2014-05-22 | 2017-03-08 | 荷兰联合利华有限公司 | 包含酶颗粒的水性液体洗涤剂制剂 |
| WO2015177077A1 (en) * | 2014-05-22 | 2015-11-26 | Unilever Plc | Aqueous liquid detergent formulation comprising enzyme particles |
| EP3511404B1 (de) | 2014-06-30 | 2024-12-18 | Henkel AG & Co. KGaA | Flüssiges reinigungsmittel enthaltend flüssige und feste enzymformulierungen |
| WO2016023685A1 (en) * | 2014-08-11 | 2016-02-18 | Novozymes A/S | Detergents and compositions with enzymatic polymer particles |
| EP3173467A1 (en) * | 2015-11-26 | 2017-05-31 | The Procter & Gamble Company | Cleaning compositions comprising enzymes |
| WO2017091674A1 (en) * | 2015-11-26 | 2017-06-01 | The Procter & Gamble Company | Liquid detergent compositions comprising protease and encapsulated lipase |
| EP3243898A2 (en) | 2016-05-09 | 2017-11-15 | The Procter & Gamble Company | Detergent composition comprising an oleic acid-transforming enzyme |
| EP3511403A1 (en) | 2016-05-09 | 2019-07-17 | The Procter & Gamble Company | Detergent composition |
| EP3540037A1 (en) | 2016-05-09 | 2019-09-18 | The Procter & Gamble Company | Detergent composition comprising a oleate 10s lipoxygenase |
| EP3540036A1 (en) | 2016-05-09 | 2019-09-18 | The Procter & Gamble Company | Detergent composition comprising a fatty acid lipoxygenase |
| EP3556834A1 (en) | 2016-05-09 | 2019-10-23 | The Procter & Gamble Company | Detergent composition comprising a fatty acid decarboxylase |
| EP3556835A1 (en) | 2016-05-09 | 2019-10-23 | The Procter & Gamble Company | Detergent composition comprising a fatty acid decarboxylase |
| EP3243897A1 (en) | 2016-05-09 | 2017-11-15 | The Procter & Gamble Company | Detergent composition comprising a fatty acid-transforming enzyme |
| EP3243896A1 (en) | 2016-05-09 | 2017-11-15 | The Procter and Gamble Company | Detergent composition comprising a fatty acid decarboxylase |
| CN109490274A (zh) * | 2019-01-04 | 2019-03-19 | 齐鲁工业大学 | 一种用于研究酶在皮革中单向传质的实验装置及使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5209643B2 (ja) | 2013-06-12 |
| WO2008084093A3 (en) | 2009-01-08 |
| CN101636480A (zh) | 2010-01-27 |
| US20120108491A1 (en) | 2012-05-03 |
| EP2129757A2 (en) | 2009-12-09 |
| US20100323945A1 (en) | 2010-12-23 |
| CN101636480B (zh) | 2014-04-09 |
| US9499773B2 (en) | 2016-11-22 |
| JP2010515800A (ja) | 2010-05-13 |
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