EP0374609A2 - Adoussicant hydrophile pour matériaux fibreux et son application - Google Patents
Adoussicant hydrophile pour matériaux fibreux et son application Download PDFInfo
- Publication number
- EP0374609A2 EP0374609A2 EP19890122605 EP89122605A EP0374609A2 EP 0374609 A2 EP0374609 A2 EP 0374609A2 EP 19890122605 EP19890122605 EP 19890122605 EP 89122605 A EP89122605 A EP 89122605A EP 0374609 A2 EP0374609 A2 EP 0374609A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- components
- alkyl radical
- softening agent
- agent according
- contained
- 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
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
Definitions
- the present invention relates to hydrophilic softening agents for fibrous materials which, in addition to conventional emulsifiers, known constituents and water, contain a water-soluble ammonium salt containing at least one fatty acid residue, at least one further quaternary compound with a long-chain alkyl residue and polyethylene wax dispersed in a known manner.
- a water-soluble ammonium salt containing at least one fatty acid residue, at least one further quaternary compound with a long-chain alkyl residue and polyethylene wax dispersed in a known manner.
- the use of these softening agents is claimed.
- polyethylene dispersions are well suited for improving the grip, in particular also for improving the sewability, of textile materials.
- fatty acid alkanolamides were used to achieve a soft, smooth surface.
- quaternary ammonium compounds are also suitable as handle components for fibrous materials, in particular textiles.
- DE-A 2 833 172 discloses water-soluble, quaternary ammonium salts having at least one fatty acid residue as softening agents and their use for the antistatic and finishing of organic fiber materials. This known equipment provides good hydrophilicity, but the handle is unsatisfactory and, above all, yellowing of the finished material can be observed to a considerable extent.
- hydrophilic softening agents all of which are aimed for Combine properties and can also be produced inexpensively if they have the composition described in more detail in claim 1.
- the essential components of the hydrophilic softening agents according to the invention are components (1). These compounds are largely known from DE-A 2 833 172. The production of the same is fundamentally known from this literature reference and can be carried out in the manner described there. Thus, only the compounds quaternized with a di-Cl to 2-alkyl ester of a Cl to 2-alkylphosphonic acid are used as components (1), with the alkyl radical having 9 to 24 C atoms of component (1) to a lesser extent (too less than 50%) can also be unsaturated.
- Components (1) are present in the softening agents in amounts of 2 to 10, in particular 2 to 6,% by weight.
- At least one other quaternary ammonium compound with at least one long-chain, saturated and / or unsaturated alkyl radical which is different from the components (1) is used as components (2).
- These compounds are generally known and, as the long-chain alkyl radical, have at least one saturated and / or unsaturated alkyl radical with at least 12, in particular 16 to 24, carbon atoms.
- Examples include octadecyloxymethylpyridinium chloride and stearylamidomethylpyridinium chloride.
- quaternary imidazolinium derivatives and quaternary ammonium compounds in the narrower sense are particularly suitable as components (2).
- component 2a 1-stearic acid amido
- the amounts of component (2) used are 1 to 13, in particular 2 to 7,% by weight, based on the hydrophilic softening agent.
- the component (3) namely the emulsifiable polyethylene (polyethylene wax), is known and is described in detail in the prior art (DE-C 23 59 966, DE-A 28 24 716 and DE-A 19 25 993).
- the emulsifiable polyethylene is one with functional groups, in particular COOH groups, which can be partially esterified. These functional groups are introduced by oxidation of the polyethylene. However, it is also possible to obtain the functionality by copolymerizing ethylene with, for example, acrylic acid.
- the emulsifiable polyethylenes have a density of at least 0.92 g / cm 3 and an acid number of 5 to 115 and a saponification number of 15 to 150 at 20 ° C.
- hydrophilic softening agents according to the invention with emulsifiable polyethylenes which have a density at 20 ° C. of 0.95 to 1.05 g / cm 3, an acid number of 10 to 60 and a saponification number of 15 to 80 are particularly preferred.
- This material is generally commercially available in the form of scales, lozenges and the like.
- Component (3) ie the polyethylene wax in dispersed form, is used in the hydrophilic softening agents in amounts of 2 to 10, in particular 3 to 8,% by weight, based on the Softening agents (calculated as polyethylene wax) are used.
- the polyethylene wax is used in the form of 20 to 35% aqueous dispersions. Different emulsifiers are required for this. These emulsifiers can have a positive effect on the soft handle effect of the hydrophilic soft handle agents.
- hydrophilic softening agents according to the invention can also contain emulsifiers and other known constituents.
- emulsifiers are indicated on a case-by-case basis when relatively small amounts of components (1) and especially (2) are used or when increased requirements for compatibility with other finishing agents, e.g. optical brighteners.
- the known nonionic and / or cationic emulsifiers different from (1) or (2) are used as emulsifiers.
- Organopolysiloxanes are to be mentioned as further known components.
- hydrophilizing agents in particular are used acting silicones into consideration. This addition makes the handle even softer, more pleasant and also has a favorable influence on the hydrophilicity.
- the amounts of organopolysiloxanes used are 0.5 to 7, in particular 1.5 to 5,% by weight, based on the hydrophilic softening agent.
- the usable organopolysiloxanes with a hydrophilizing effect are likewise known to the person skilled in the art.
- Organopolysiloxanes which have groups (a) and (b) in the same molecule are particularly suitable.
- fatty acid dialkanolamides as constituents of softening agent formulations. These connections can also be used here. With regard to the use of these compounds, reference is made to the prior art. These fatty acid dialkanolamides (fatty acid residues with 16-22 carbon atoms) are used in amounts of 1 to 10, in particular 4 to 8,% by weight, based on the hydrophilic softening agent.
- hydrophilic softening agents such as Paraffin emulsions or the condensation products known from DE-C 2 318 906 are known to the person skilled in the art and require no further explanation.
- the soft-grip agents according to the invention can be produced by mixing the components together, advantageously at a slightly elevated temperature.
- the pH value improves the resistance to metal salts with inorganic acids, for example hydrochloric acid, or else mono- or dibasic organic acids, such as acetic, maleic and especially glycolic acid, adjusted to 3 to 7, in particular 3.5 to 6.
- the hydrophilic softening agents obtained serve for the softening and at the same time hydrophilizing finishing of fiber materials of all kinds, in particular terry goods, especially cotton terry goods.
- all other textiles that are expected to have moisture-wicking, in particular sweat-absorbing properties, such as shirt poplin and especially bed linen, are advantageously equipped with the present agents.
- the textiles are treated in a known manner with liquors which contain 15 to 80 g / l, in particular 20 to 60 g / l, of the hydrophilic softening agents, based on a dispersion with a total solids content of about 20% by weight. which results in a coating of about 0.2 to 3% by weight of solid substance on the fiber material.
- the softening agents according to the invention can also advantageously be used by the pull-out process. In this method, approximately 1 to 6, in particular 2 to 4.5%, based on the weight of the goods (based on the soft handle dispersion) are used, depending on the required circulation.
- the equipment is completed by conventional drying and, if necessary, brief post-condensation.
- the degree of whiteness is determined according to a formula developed by GANZ (see R.G. Griesser Textilveredlung 18 (1983), No. 5, pages 157 to 162).
- the "ELREPHO-2000 spectrophotometer for reflectance measurements" from Data-color has proven itself for these investigations.
- the mixture is then allowed to cool to 100 ° C. and 136 g of dimethyl methanephosphonate are added dropwise, the temperature again not to exceed 120 ° C. Finally, the temperature is carefully raised to 130 ° C. and stirring is continued for 2 hours at this temperature.
- the N, N-diethyl-N-methyl-N (stearylamidopropyl) ammonium monomethyl methanephosphonate obtained is filled hot through a filter. After cooling, a pasty product is obtained.
- hydrophilic softening agent 20%, based on polyethylene wax) of ethoxylated alcohols as emulsifier; emulsifiable polyethylene with a density of 0.96 g / m3, acid number approx. 25 and saponification number approx 45) added, cooled to below 30 ° C and poured off through a filter.
- a storage-stable (at least 1 year), hydrophilic softening agent is obtained, which can also be exposed to temperatures of 50 ° C and more, or temperatures below freezing point (to -15 ° C) without being influenced.
- Example 1 B 35 g of component (1) prepared as described above are used instead of component (1) used there, and instead of the polyethylene wax dispersion described in Example 1 B), 250 g of a nonionic, finely divided, aqueous, 21% polyethylene wax dispersion (25% tallow fatty amine, ethoxylated with 8 mol ethylene oxide, based on polyethylene wax, as Emulsifier; Polyethylene wax with a density at 20 ° C of 0.93 g / cm3 and an acid / saponification number of about 16) was used.
- a nonionic, finely divided, aqueous, 21% polyethylene wax dispersion 25% tallow fatty amine, ethoxylated with 8 mol ethylene oxide, based on polyethylene wax, as Emulsifier; Polyethylene wax with a density at 20 ° C of 0.93 g / cm3 and an acid / saponification number of about 16
- a softening agent can be prepared using 60 g of components (2d) and (2h) instead of the two components (2e1) and (2f).
- 35 g / l of the dispersion prepared under B) are used and a light cotton terry towel (240 g / m 2) is equipped with the resulting liquor by immersion, squeezing to 100% liquor absorption and drying at 120 ° C. for 10 minutes.
- the goods treated in this way have a very soft, fluffy, full feel and are also very good hydrophilic.
- connection 11.12 of DE-A 2 833 172 is established.
- a softening agent is produced in accordance with Example 1 B), the following polyethylene dispersion being used: 300 g of a 27% polyethylene wax dispersion (Poly ethylene wax with a density at 20 ° C of 0.98 g / cm3, an acid number of 25 and a saponification number of 50; 50%, based on polyethylene wax, of an emulsifier mixture of C 16/18 fatty alcohol ethoxylated with an average of 40 moles of ethylene oxide per mole of alcohol and emulsifier according to Example 1 of US Pat. No. 3,904,661 in a ratio of 1: 9) with a correspondingly reduced amount of water.
- a 27% polyethylene wax dispersion Poly ethylene wax with a density at 20 ° C of 0.98 g / cm3, an acid number of 25 and a saponification number of 50
- a cotton jersey (285 g / m2) is treated by the pull-out process at 40 ° C. in a liquor ratio of 1:30 (weight: volume) with a liquor which contains 3% of the softening agent prepared as described above (duration 30 minutes). Finally, the goods are spun off briefly and dried at 110 ° C.
- the cotton jersey finished in this way is characterized by a soft, fluffy feel, good hydrophilicity and good retention of whiteness.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3842571 | 1988-12-17 | ||
DE3842571A DE3842571A1 (de) | 1988-12-17 | 1988-12-17 | Hydrophile weichgriffmittel fuer faserige materialien und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0374609A2 true EP0374609A2 (fr) | 1990-06-27 |
EP0374609A3 EP0374609A3 (fr) | 1992-03-04 |
Family
ID=6369431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19890122605 Ceased EP0374609A3 (fr) | 1988-12-17 | 1989-12-07 | Adoussicant hydrophile pour matériaux fibreux et son application |
Country Status (3)
Country | Link |
---|---|
US (1) | US5019281A (fr) |
EP (1) | EP0374609A3 (fr) |
DE (1) | DE3842571A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0535438A1 (fr) * | 1991-10-04 | 1993-04-07 | Pfersee Chemie GmbH | Dispersions aqueuses de lécithine et leur utilisation pour le traitement de matières fibreuses |
EP0535437A1 (fr) * | 1991-10-01 | 1993-04-07 | Pfersee Chemie GmbH | Dispersions aqueuses à base d'organopolysiloxanes contenant de l'azote |
WO1996010623A1 (fr) * | 1994-10-04 | 1996-04-11 | Henkel Kommanditgesellschaft Auf Aktien | Dispersions aqueuses d'agents assouplissants |
US6180593B1 (en) * | 1998-09-30 | 2001-01-30 | Goldschmidt Rewo Gmbh & Co. Kg | Fabric softeners with improved color-retaining action |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02259162A (ja) * | 1989-03-29 | 1990-10-19 | Nitto Boseki Co Ltd | セルロース系布帛の処理方法 |
US5789373A (en) * | 1996-01-31 | 1998-08-04 | Baker; Ellen Schmidt | Laundry additive compositions including dispersible polyolefin |
US5728673A (en) * | 1996-01-31 | 1998-03-17 | The Procter & Gamble Company | Process for making a fluid, stable liquid fabric softening composition including dispersible polyolefin |
US5830843A (en) * | 1996-01-31 | 1998-11-03 | The Procter & Gamble Company | Fabric care compositions including dispersible polyolefin and method for using same |
WO1997046654A1 (fr) * | 1996-06-03 | 1997-12-11 | The Procter & Gamble Company | Compositions adoucissant les tissus |
GB9725828D0 (en) * | 1997-12-06 | 1998-02-04 | Albright & Wilson Uk Ltd | Fabric treatment and polymeric compositions therefor |
CA2384108C (fr) * | 1999-09-07 | 2011-07-05 | Crompton Corporation | Sels d'ammonium quaternaire en tant qu'agents epaississants pour des systemes aqueux |
US7358215B1 (en) * | 1999-09-07 | 2008-04-15 | Akzo Nobel Surface Chemistry Llc | Quaternary ammonium salts as thickening agents for aqueous systems |
WO2002079364A1 (fr) * | 2001-03-30 | 2002-10-10 | Ciba Specialty Chemicals Holding Inc. | Compositions d'adoucissant et leur utilisation |
US10900168B2 (en) | 2002-04-09 | 2021-01-26 | Gregory van Buskirk | Fabric treatment for stain repellency |
US20030192130A1 (en) * | 2002-04-09 | 2003-10-16 | Kaaret Thomas Walter | Fabric treatment for stain release |
US7893014B2 (en) * | 2006-12-21 | 2011-02-22 | Gregory Van Buskirk | Fabric treatment for stain release |
US20050204477A1 (en) * | 2004-03-22 | 2005-09-22 | Casella Victor M | Fabric treatment for stain release |
WO2016115408A1 (fr) | 2015-01-14 | 2016-07-21 | Gregory Van Buskirk | Procédé de traitement de tissu amélioré pour l'élimination des taches |
US10822577B2 (en) | 2002-04-09 | 2020-11-03 | Gregory van Buskirk | Fabric treatment method for stain release |
US6620794B1 (en) * | 2002-07-08 | 2003-09-16 | Colonial Chemical Inc. | Guerbet functionalized phospholipids |
US20050229327A1 (en) * | 2004-04-20 | 2005-10-20 | Casella Victor M | Fabric treatment for stain release |
US20070125542A1 (en) * | 2005-12-07 | 2007-06-07 | Akzo Nobel N.V. | High temperature gellant in low and high density brines |
CN110983787B (zh) * | 2019-12-17 | 2022-02-11 | 广东新翔星科技股份有限公司 | 一种亲水挺厚有机硅柔软剂及其制备方法 |
CN115787308B (zh) * | 2022-12-20 | 2024-02-02 | 莆田达凯新材料有限公司 | 一种适用于n/r罗马布的柔软剂及其制备方法及整理方法 |
CN115787137A (zh) * | 2023-01-07 | 2023-03-14 | 许昌鸿洋生化实业发展有限公司 | 一种抗菌抗紫外可降解假发纤维及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2399433A1 (fr) * | 1977-08-01 | 1979-03-02 | Ciba Geigy Ag | Sels d'ammonium quaternaire de produits antistatiques ou d'agents adoucisseurs du toucher presentant des restes d'acide gras, leur procede de preparation et leur utilisation |
EP0032267A1 (fr) * | 1980-01-11 | 1981-07-22 | THE PROCTER & GAMBLE COMPANY | Compositions concentrées de traitement de textiles et procédé pour leur préparation |
EP0075168A1 (fr) * | 1981-09-17 | 1983-03-30 | Bayer Ag | Composés d'ammonium |
EP0082456A2 (fr) * | 1981-12-18 | 1983-06-29 | Hoechst Aktiengesellschaft | Prémélanges concentrés d'agents adoucissant le linge |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3583912A (en) * | 1968-01-29 | 1971-06-08 | Cpc International Inc | Detergent compatible fabric softener |
US3565840A (en) * | 1968-05-21 | 1971-02-23 | Allied Chem | Color stabilized oxidized polyethylene emulsions |
US3920563A (en) * | 1972-10-31 | 1975-11-18 | Colgate Palmolive Co | Soap-cationic combinations as rinse cycle softeners |
US3954634A (en) * | 1973-07-27 | 1976-05-04 | S. C. Johnson & Son, Inc. | Stable, low-viscosity fabric softener |
DE2359966C3 (de) * | 1973-12-01 | 1980-07-03 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Verfahren zur wasserabweisenden Ausrüstung von Fasermaterialien aller Art |
JPS5932585B2 (ja) * | 1978-12-05 | 1984-08-09 | 花王株式会社 | 繊維用柔軟剤 |
JPS6030395B2 (ja) * | 1979-02-23 | 1985-07-16 | ライオン株式会社 | 仕上剤組成物 |
JPS55116877A (en) * | 1979-03-02 | 1980-09-08 | Lion Fat Oil Co Ltd | Household softening finish agent with excellent slip imparting effect |
DE3437321A1 (de) * | 1984-10-11 | 1986-04-24 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Umsetzungsprodukte von hoeheren fettsaeuren mit dialkanolaminen, deren herstellung und verwendung |
US4851141A (en) * | 1984-12-12 | 1989-07-25 | Colgate-Palmolive Company | Concentrated stable nonaqueous fabric softener composition |
US4960526A (en) * | 1985-07-25 | 1990-10-02 | Colgate-Polmolive Company | Diammonium compound containing fabric softening and antistatic detergent composition |
GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
JPS6369884A (ja) * | 1986-09-12 | 1988-03-29 | Lion Corp | 柔軟剤組成物 |
US4908160A (en) * | 1986-10-25 | 1990-03-13 | Tag Investments, Inc. | Fire retardant composition |
DE3720332A1 (de) * | 1987-06-19 | 1988-12-29 | Huels Chemische Werke Ag | Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung |
-
1988
- 1988-12-17 DE DE3842571A patent/DE3842571A1/de not_active Withdrawn
-
1989
- 1989-12-07 EP EP19890122605 patent/EP0374609A3/fr not_active Ceased
- 1989-12-12 US US07/450,134 patent/US5019281A/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2399433A1 (fr) * | 1977-08-01 | 1979-03-02 | Ciba Geigy Ag | Sels d'ammonium quaternaire de produits antistatiques ou d'agents adoucisseurs du toucher presentant des restes d'acide gras, leur procede de preparation et leur utilisation |
EP0032267A1 (fr) * | 1980-01-11 | 1981-07-22 | THE PROCTER & GAMBLE COMPANY | Compositions concentrées de traitement de textiles et procédé pour leur préparation |
EP0075168A1 (fr) * | 1981-09-17 | 1983-03-30 | Bayer Ag | Composés d'ammonium |
EP0082456A2 (fr) * | 1981-12-18 | 1983-06-29 | Hoechst Aktiengesellschaft | Prémélanges concentrés d'agents adoucissant le linge |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0535437A1 (fr) * | 1991-10-01 | 1993-04-07 | Pfersee Chemie GmbH | Dispersions aqueuses à base d'organopolysiloxanes contenant de l'azote |
EP0535438A1 (fr) * | 1991-10-04 | 1993-04-07 | Pfersee Chemie GmbH | Dispersions aqueuses de lécithine et leur utilisation pour le traitement de matières fibreuses |
WO1996010623A1 (fr) * | 1994-10-04 | 1996-04-11 | Henkel Kommanditgesellschaft Auf Aktien | Dispersions aqueuses d'agents assouplissants |
US6180593B1 (en) * | 1998-09-30 | 2001-01-30 | Goldschmidt Rewo Gmbh & Co. Kg | Fabric softeners with improved color-retaining action |
Also Published As
Publication number | Publication date |
---|---|
DE3842571A1 (de) | 1990-06-21 |
EP0374609A3 (fr) | 1992-03-04 |
US5019281A (en) | 1991-05-28 |
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