WO1998007920A1 - Textilausrüstungsmittel - Google Patents
Textilausrüstungsmittel Download PDFInfo
- Publication number
- WO1998007920A1 WO1998007920A1 PCT/EP1997/004304 EP9704304W WO9807920A1 WO 1998007920 A1 WO1998007920 A1 WO 1998007920A1 EP 9704304 W EP9704304 W EP 9704304W WO 9807920 A1 WO9807920 A1 WO 9807920A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- alkyl
- fatty acid
- radical
- composition according
- Prior art date
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/645—Mixtures of compounds all of which are cationic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
- D06M13/473—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- the invention relates to new agents for finishing textile fabrics based on esterquats and quaternized fatty acid imidazo and their use for softening and yellowing stabilization of fabrics.
- finishing of yarns, fabrics, fabrics up to the finished textiles comprises a complex requirement profile.
- the most important property that finishing agents must have is to give the textiles a pleasant soft feel.
- cationic surfactants are generally used, among which the esterquats are particularly important because of their good ecological compatibility.
- the finishing can take place both in the context of the textile pre- and post-treatment.
- a further requirement then exists to protect textiles against soiling, for which purpose conventional laundry aftertreatment agents are added polymers of the so-called "soil repeilants" type.
- a third important aspect is the stabilization of fabrics against the influence of ozone, which is very easy, especially with blue denim yellowing, but this requirement has so far not been satisfactorily met by the means of the prior art.
- the object of the invention was therefore to provide new means which allow textile fabrics, ie yarns, fabrics and finished textiles, but in particular blue denim fabrics and jeans made therefrom, to be given a pleasant soft feel at the same time and against Equip yellowing Description of the invention
- the invention relates to textile finishing agents containing
- esters quats is generally understood to mean quaternized fatty acid ethanoamine ester salts. These are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the international patent application WO 91/01295 (Henkel) , after which t ⁇ ethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide.
- R CO is an acyl radical having 6 to 22 carbon atoms
- R 2 and R 3 independently of one another are hydrogen or R 1 CO
- R 4 is an alkyl radical having 1 to 4 carbon atoms or a (CH ⁇ CH ⁇ OJqH group, m, n and pm sum for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
- ester quats which can be used in the sense of the invention are products based on Caproic acid, caprylic acid, capric acid, launic acid, mypinic acid, palmitic acid, isosteanic acid, stearic acid, oleic acid, elaidic acid, arachidic acid, behenic acid and erucic acid, and their technical mixtures, which are predominantly obtained, for example, in the pressure cleavage of natural fats and fatty acids or fatty acids such as, for example, tallow or palm fatty acid , 1 1 to 3 1 are used With regard to the application properties of the ester quats, a ratio of 1, 2 1 to 2.2 1, preferably 1, 5 1 to 1, 9 1 has proven to be particularly advantageous.
- the preferred ester quats are technical Mixtures of mono-, di- and T ⁇ -esters with an average degree of esterification of 1.5 to 1.9 and are derived from tallow fatty acid.
- quaternized fatty acid triethanolamm ester salts of the formula (I) have proven to be particularly advantageous, in which R 1 CO stands for the acyl residue of tallow fatty acid, R 2 for R 1 CO, R 3 for hydrogen, R 4 for a methyl group, m, n and p for 0 and X for methyl sulfate
- quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) may also be used as ester quats.
- R 1 CO for an acyl radical having 6 to 22 carbon atoms, preferably for an acyl radical derived from tallow fatty acid
- R 2 for hydrogen or R 1 CO
- R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms
- m and n in total represents 0 or numbers from 1 to 12
- X represents halide, alkyl sulfate or alkyl phosphate
- R 1 CO is an acyl radical having 6 to 22 carbon atoms, preferably an acyl radical derived from the fatty acid mixture containing the tallow fatty acid
- R 2 is hydrogen or R 1 CO
- R 4 , R 6 and R 7 are, independently of one another, alkyl radicals having 1 up to 4 carbon atoms, m and n in total represent 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
- esterquats of the formulas (II) and (III) usually come in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if necessary.
- Quaternized fatty acid imidazolines are also known cationic surfactants which are usually obtained by condensing fatty acids with diamines, preferably ethylenediamines and subsequent quaternization with alkyl halides or dialkyl sulfates.
- Processes for producing the imidazolines and their quaternization products are known, for example, from the publications DE-A1 40 20 271, DE-A1 40 38 983 and DE-A1 41 16 648 (Henkel).
- the imidazolines can also contain proportions of open-chain hydrolysis products. Usually they follow the formula (IV),
- R 8 is an alkyl and / or alkenyl radical having 7 to 21, preferably 11 to 17 carbon atoms
- R 9 is optionally hydroxyl-substituted alkyl radicals having 1 to 4 carbon atoms or a benzyl radical
- R 10 is hydroxy-substituted alkyl radicals having 2 to 4 carbon atoms or a CH2CH2NHCOR 8 radical
- X represents halide or alkyl sulfate.
- products are used which are derived from oleic acid or a fatty acid cut containing predominantly oleic acid.
- Quaternized fatty acid imidazolines which are obtained by condensation of oleic acid with diethylenetriamine or aminoethylethanolamine and subsequent quaternization with dimethyl sulfate or methyl chloride are particularly preferred.
- the weight ratio of the two components (a) and (b) in the textile finishing agents according to the invention can be 90:10 to 10:90, preferably 15:85 to 50:50 and in particular 20:80 to 25:75.
- the agents according to the invention not only give textile fabrics, preferably blue denim fabrics, a pleasant soft feel, but also provide reliable protection against yellowing. Another object of the invention therefore relates to the use of the mixtures as finishing agents for the simultaneous softening and yellowing stabilization of textile fabrics.
- the agents themselves are usually in the form of aqueous solutions or pastes with an active substance content in the range from 5 to 30% by weight. To adjust the viscosity, they can also contain, for example, electrolyte salts.
- the assessment of ozone stabilization was checked using blue denim fabric.
- the evaluation is based on the ozone test according to AATCC 109-1992 using an ozone chamber of the type TriC-03 from Textile Innovators CorpVUSA.
- the results are summarized in Table 1.
- the following surfactants were used:
- Methyl-quaternized fatty acid imidazoline produced from oleic acid of 90 to 100 iodine number and aminoethylethanolamine, in the form of the methyl sulfate salt;
- Methyl-quaternized fatty acid minidazoline prepared from oleic acid of 85 to 90 iodine number and aminoethylethanolamine, in the form of the methyl sulfate salt;
- Methylquaternized fatty acid minidazoline made from tall oil fatty acid and aminoethylethanolamine, in the form of the methyl isulfate acid;
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/242,424 US6402976B1 (en) | 1996-08-16 | 1997-08-07 | Textile finishing agent |
BR9711308A BR9711308A (pt) | 1996-08-16 | 1997-08-07 | Agente de apresto de t-xteis |
DK97937560T DK0918901T3 (da) | 1996-08-16 | 1997-08-07 | Anvendelse af tekstilfærdigbehandlingsmidler |
DE59702736T DE59702736D1 (de) | 1996-08-16 | 1997-08-07 | Verwendung von textilausrüstungsmitteln |
EP97937560A EP0918901B1 (de) | 1996-08-16 | 1997-08-07 | Verwendung von textilausrüstungsmitteln |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19633104.8 | 1996-08-16 | ||
DE19633104A DE19633104C1 (de) | 1996-08-16 | 1996-08-16 | Verwendung von Tensidmischungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998007920A1 true WO1998007920A1 (de) | 1998-02-26 |
Family
ID=7802828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/004304 WO1998007920A1 (de) | 1996-08-16 | 1997-08-07 | Textilausrüstungsmittel |
Country Status (9)
Country | Link |
---|---|
US (1) | US6402976B1 (de) |
EP (1) | EP0918901B1 (de) |
BR (1) | BR9711308A (de) |
DE (2) | DE19633104C1 (de) |
DK (1) | DK0918901T3 (de) |
ES (1) | ES2153683T3 (de) |
PT (1) | PT918901E (de) |
TR (1) | TR199900274T2 (de) |
WO (1) | WO1998007920A1 (de) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022235655A1 (en) | 2021-05-04 | 2022-11-10 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising insoluble alpha-glucan |
WO2023287684A1 (en) | 2021-07-13 | 2023-01-19 | Nutrition & Biosciences USA 4, Inc. | Cationic glucan ester derivatives |
WO2023081346A1 (en) | 2021-11-05 | 2023-05-11 | Nutrition & Biosciences USA 4, Inc. | Glucan derivatives for microbial control |
WO2023114942A1 (en) | 2021-12-16 | 2023-06-22 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising cationic alpha-glucan ethers in aqueous polar organic solvents |
WO2024015769A1 (en) | 2022-07-11 | 2024-01-18 | Nutrition & Biosciences USA 4, Inc. | Amphiphilic glucan ester derivatives |
WO2024081773A1 (en) | 2022-10-14 | 2024-04-18 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising water, cationic alpha-1,6-glucan ether and organic solvent |
WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
WO2025072417A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
WO2025072416A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19829787A1 (de) * | 1998-07-03 | 2000-01-05 | Henkel Kgaa | Avivagemittel |
DE50305183D1 (de) * | 2003-06-24 | 2006-11-09 | Cognis Ip Man Gmbh | Perlglänzende wässrige Zubereitungen |
CN111778711B (zh) * | 2020-06-12 | 2022-12-23 | 鲁泰纺织股份有限公司 | 解决牛仔衬衫氧化黄变的生产工艺 |
Citations (9)
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---|---|---|---|---|
US4149978A (en) * | 1977-07-12 | 1979-04-17 | The Procter & Gamble Company | Textile treatment composition |
EP0239910A2 (de) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biologisch abbaubare Gewebeweichmacher |
DE3904754A1 (de) * | 1988-02-17 | 1989-08-31 | Kao Corp | Konzentrierter weichmacher fuer die verwendung in kleidungsstuecken |
WO1991001295A1 (de) * | 1989-07-17 | 1991-02-07 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von quartären ammoniumverbindungen |
EP0431652A1 (de) * | 1989-09-06 | 1991-06-12 | The Procter & Gamble Company | Weichmachende und antistatische Zusammensetzungen für Textilien |
DE4020271A1 (de) * | 1990-06-26 | 1992-01-02 | Henkel Kgaa | Salze von fettsaeureamiden und fettsaeureimidazolinen |
DE4243862A1 (de) * | 1992-12-23 | 1994-06-30 | Huels Chemische Werke Ag | Verfahren zur Quaternierung von Triethanolaminfettsäureestern und Imidazolinamiden in alkoxylierten Fetten oder Ölen als Reaktionsmedium und die Verwendung der Reaktionsmischungen als Wäscheweichspülerwirkstoffkomponenten |
KR940006256B1 (ko) * | 1992-03-07 | 1994-07-13 | 재단법인 한국화학연구소 | 사차 암모늄염 섬유 유연제의 조성물 |
EP0607772A2 (de) * | 1993-01-16 | 1994-07-27 | Hüls Aktiengesellschaft | Quaternierte Alkylaminalkoxylate als Viskositätsregulatoren für wässrige Dispersionen von stickstoffhaltigen kationenaktiven Wirkstoffkomponenten |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US3915867A (en) | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
US4370272A (en) | 1980-01-14 | 1983-01-25 | Stepan Chemical Company | Alkoxylated quaternary ammonium surfactants |
DE3877422T2 (de) | 1987-05-01 | 1993-05-13 | Procter & Gamble | Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel. |
EP0295739A3 (de) | 1987-06-09 | 1990-01-17 | The Procter & Gamble Company | Verfahren zum Herstellen biologisch abbaubarer Wäschebehandlungszusammensetzungen |
EP0309052B1 (de) | 1987-09-23 | 1992-11-25 | The Procter & Gamble Company | Lineare alkoxylierte Alkohole enthaltende stabile, biologisch abbaubare Wäscheweichspülerzusammensetzungen |
DE3926740C2 (de) * | 1989-08-12 | 1997-05-15 | Witco Surfactants Gmbh | Wässrige Weichspülmittel und deren Verwendung |
DE4038983A1 (de) | 1990-12-06 | 1992-06-11 | Henkel Kgaa | Verfahren zur herstellung duennfluessiger imidazoliniumtenside durch quaternierung von 1-hydroxyethyl-2-alkylimidazolinen |
US5591186A (en) | 1991-05-22 | 1997-01-07 | Wurster; Helmut | Self-cutting trocar |
DE4116648A1 (de) | 1991-05-22 | 1992-11-26 | Helmut Dipl Ing Wurster | Selbstschneidender trokar |
GB9122486D0 (en) * | 1991-10-23 | 1991-12-04 | Cussons Int Ltd | Fabric softener composition |
EP0640121B2 (de) * | 1992-05-12 | 2003-08-27 | The Procter & Gamble Company | Konzentrierte flüssige gewebeweichmacherzusammensetzungen mit biologisch abbaubaren gewebeweichmachern |
KR0143542B1 (ko) | 1992-06-15 | 1998-08-17 | 요미야마 아끼라 | 반도체 장치 및 그 제조 방법 |
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US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
-
1996
- 1996-08-16 DE DE19633104A patent/DE19633104C1/de not_active Expired - Fee Related
-
1997
- 1997-08-07 US US09/242,424 patent/US6402976B1/en not_active Expired - Fee Related
- 1997-08-07 WO PCT/EP1997/004304 patent/WO1998007920A1/de active IP Right Grant
- 1997-08-07 DE DE59702736T patent/DE59702736D1/de not_active Expired - Fee Related
- 1997-08-07 ES ES97937560T patent/ES2153683T3/es not_active Expired - Lifetime
- 1997-08-07 TR TR1999/00274T patent/TR199900274T2/xx unknown
- 1997-08-07 DK DK97937560T patent/DK0918901T3/da active
- 1997-08-07 BR BR9711308A patent/BR9711308A/pt not_active IP Right Cessation
- 1997-08-07 PT PT97937560T patent/PT918901E/pt unknown
- 1997-08-07 EP EP97937560A patent/EP0918901B1/de not_active Expired - Lifetime
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US4149978A (en) * | 1977-07-12 | 1979-04-17 | The Procter & Gamble Company | Textile treatment composition |
EP0239910A2 (de) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biologisch abbaubare Gewebeweichmacher |
DE3904754A1 (de) * | 1988-02-17 | 1989-08-31 | Kao Corp | Konzentrierter weichmacher fuer die verwendung in kleidungsstuecken |
WO1991001295A1 (de) * | 1989-07-17 | 1991-02-07 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von quartären ammoniumverbindungen |
EP0431652A1 (de) * | 1989-09-06 | 1991-06-12 | The Procter & Gamble Company | Weichmachende und antistatische Zusammensetzungen für Textilien |
DE4020271A1 (de) * | 1990-06-26 | 1992-01-02 | Henkel Kgaa | Salze von fettsaeureamiden und fettsaeureimidazolinen |
KR940006256B1 (ko) * | 1992-03-07 | 1994-07-13 | 재단법인 한국화학연구소 | 사차 암모늄염 섬유 유연제의 조성물 |
DE4243862A1 (de) * | 1992-12-23 | 1994-06-30 | Huels Chemische Werke Ag | Verfahren zur Quaternierung von Triethanolaminfettsäureestern und Imidazolinamiden in alkoxylierten Fetten oder Ölen als Reaktionsmedium und die Verwendung der Reaktionsmischungen als Wäscheweichspülerwirkstoffkomponenten |
EP0607772A2 (de) * | 1993-01-16 | 1994-07-27 | Hüls Aktiengesellschaft | Quaternierte Alkylaminalkoxylate als Viskositätsregulatoren für wässrige Dispersionen von stickstoffhaltigen kationenaktiven Wirkstoffkomponenten |
Non-Patent Citations (1)
Title |
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DATABASE WPI Section Ch Week 9617, Derwent World Patents Index; Class D25, AN 96-169634, XP002047797 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022235655A1 (en) | 2021-05-04 | 2022-11-10 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising insoluble alpha-glucan |
WO2023287684A1 (en) | 2021-07-13 | 2023-01-19 | Nutrition & Biosciences USA 4, Inc. | Cationic glucan ester derivatives |
WO2023081346A1 (en) | 2021-11-05 | 2023-05-11 | Nutrition & Biosciences USA 4, Inc. | Glucan derivatives for microbial control |
WO2023081341A1 (en) | 2021-11-05 | 2023-05-11 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising one cationic alpha- 1,6-glucan derivative and one alpha- 1,3-glucan |
WO2023114942A1 (en) | 2021-12-16 | 2023-06-22 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising cationic alpha-glucan ethers in aqueous polar organic solvents |
WO2024015769A1 (en) | 2022-07-11 | 2024-01-18 | Nutrition & Biosciences USA 4, Inc. | Amphiphilic glucan ester derivatives |
WO2024081773A1 (en) | 2022-10-14 | 2024-04-18 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising water, cationic alpha-1,6-glucan ether and organic solvent |
WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
WO2025072417A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
WO2025072416A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
Also Published As
Publication number | Publication date |
---|---|
ES2153683T3 (es) | 2001-03-01 |
EP0918901B1 (de) | 2000-12-06 |
TR199900274T2 (xx) | 1999-05-21 |
DE19633104C1 (de) | 1997-10-16 |
DE59702736D1 (de) | 2001-01-11 |
US6402976B1 (en) | 2002-06-11 |
BR9711308A (pt) | 1999-08-17 |
PT918901E (pt) | 2001-04-30 |
EP0918901A1 (de) | 1999-06-02 |
DK0918901T3 (da) | 2001-03-05 |
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