EP0324345B1 - Procédé pour rendre hydrophobes le cuir, les fourrures et les cuirs synthétiques - Google Patents

Procédé pour rendre hydrophobes le cuir, les fourrures et les cuirs synthétiques Download PDF

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Publication number
EP0324345B1
EP0324345B1 EP89100027A EP89100027A EP0324345B1 EP 0324345 B1 EP0324345 B1 EP 0324345B1 EP 89100027 A EP89100027 A EP 89100027A EP 89100027 A EP89100027 A EP 89100027A EP 0324345 B1 EP0324345 B1 EP 0324345B1
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EP
European Patent Office
Prior art keywords
leather
weight
water
furs
groups
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.)
Expired - Lifetime
Application number
EP89100027A
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German (de)
English (en)
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EP0324345A1 (fr
Inventor
Herbert Dr. Bay
Guenter Dr. Eckert
Wolfram Dr. Bergold
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes

Definitions

  • the invention relates to a process for hydrophobizing leather, furs and leather substitutes with a carboxyl-containing polysiloxane, the carboxyl groups of which are present in neutralized form, in the aqueous phase in the absence of emulsifiers and without aftertreatment with mineral tanning agents.
  • Polysiloxanes, fluorocarbon resins, aluminum soaps or water-in-oil emulsifiers suitable for hydrophobicization are also suitable for the finishing stage of the hydrophobization of leather, furs and leather substitutes, which are always present in organic solvents, e.g. Petrol or chlorinated hydrocarbons, dissolved, are used. Disadvantages when working with these solvents are the harmful and environmentally harmful effects and the fire hazard when using gasoline. Incidentally, the leather treatment with products dissolved in organic solvents means a considerable amount of additional work.
  • DE-OS 3 529 869 (EP-A- 0 213 480) a method for hydrophobicizing leather and furs with a silicone oil in the presence of a salt of an N- (C9bisC20-acyl) amino acid, for example oleic acid sarcoside or medialanic acid, as Emulsifier described in which the aqueous emulsion of a silicone oil in the presence of the above emulsifiers in an aqueous liquor lets the leather or fur to be treated act at pH values of 4.5 to 8.0, then sets them to a pH value of 3.0 to 5.0 and after-treatment with a 2-, 3- to maintain favorable results or 4-valent metal salt must be carried out.
  • a salt of an N- (C9bisC20-acyl) amino acid for example oleic acid sarcoside or medialanic acid
  • silicone oils which can be used here are the commercially available silicone oils with viscosities of 30 to 1,000 mPas, preferably 80 to 500 mPas. Such silicone oils can be readily used by those skilled in the art, for example Römpps Chemie-Lexikon, 7th edition, Stuttgart, 1975, pp. 3223ff, or Ullmanns Enzyklopadie der techn. Chemie, 4th ed., 1982, volume 21, pp. 512ff. The viscosities given are a practical measure of the molecular weights, which can often only be determined with great effort.
  • Preferred silicone oils in this process are dimethylpolysiloxanes with a viscosity of 80 to 110 mPas, phenylmethyl polysiloxanes with a viscosity of 85 to 120 mPas, dimethylpolysiloxanes with amino groups as reactive groups, characterized by an amine number of about 0.8 to 1.1. 0 and a viscosity of 30 to 50 mPa ⁇ s, and dimethylpolysiloxanes with carboxyl groups as reactive groups, on average with 2 to 10 carboxyl groups per molecule.
  • Dimethylpolysiloxanes, the methyl groups of which are partially replaced by mercaptopropyl or aminopropyl groups as reactive groups are very particularly preferred.
  • the object of the present invention is to provide a process for waterproofing leather, furs and leather substitutes which can be carried out in an aqueous liquor and which involves the use of emulsifiers and aftertreatment with metal salts, in particular chromium III salts , can be dispensed with.
  • the solution to the problem consists in a process for hydrophobizing with a carboxyl-containing polysiloxane, the carboxyl groups of which are present in neutralized form.
  • a carboxyl-containing polysiloxane the carboxyl groups of which are present in neutralized form.
  • these special polysiloxanes the salts of which have self-emulsifying properties in water or can be soluble, at least equivalent results to the prior art are achieved without the presence of emulsifiers and without aftertreatment with metal salts, since these can readily be incorporated into the leather in an unforeseeable manner have it incorporated.
  • Organic solvents, especially hydrocarbons, can be dispensed with.
  • the method of the invention is characterized by its simple, time-saving, safe and environmentally friendly implementation. Usual auxiliaries for the preparation of the emulsions or solutions are not necessary.
  • the invention relates to a process for the hydrophobization of leather, furs and leather substitutes with carboxyl-containing polysiloxane, which is characterized in that the carboxyl groups of the polysiloxane are in neutralized form and in that the neutralized polysiloxane is present in an amount of 0.1 to 15% by weight.
  • the leather or furs to be treated can act before, during or after retanning and then adjusts to a pH of 3.0 to 5.0, preferably 3.5 to 4.5.
  • carboxyl-containing polysiloxanes used in the process according to the invention are known per se to the person skilled in the art. Particularly suitable are polysiloxanes in which the remaining valences of silicon are saturated by hydrocarbon radicals, in particular methyl, but also ethyl, propyl or phenyl, and which have carboxylic acid or preferably carboxylic acid anhydride groups at their ends and / or in the side chains in their production via these hydrocarbon radicals Molecule built in included.
  • hydrocarbon radicals in particular methyl, but also ethyl, propyl or phenyl
  • Dimethylpolysiloxanes and methyl-propyl-polysiloxanes which have terminal carboxylic anhydride groups are particularly preferred. They can be characterized by their anhydride numbers from 0.2 to 1.7, preferably from 0.4 to 0.8.
  • the molecular weights of the polysiloxanes with acid anhydride groups are expediently described by the viscosity ranges from 100 to 500 mPa ⁇ s, preferably 150 to 220 mPa ⁇ s (determined in each case in an Ubbelohde viscometer at 25 ° C.).
  • the polysiloxanes are expediently brought to a pH of 7 in aqueous solution with the appropriate amount of alkali (for example sodium or valium hydroxide), ammonia, a saturated organic amine, alkanolamine or an aminocarboxylic acid to 10, preferably 7.5 to 8.5.
  • alkali for example sodium or valium hydroxide
  • ammonia a saturated organic amine
  • alkanolamine or an aminocarboxylic acid
  • the carboxylic anhydride groups can also first be reacted with alcohols to give the half ester, the free carboxyl group is then neutralized.
  • the salts are the alkali metal salts, in particular sodium or potassium, the ammonium salts, the amine salts, in particular those of mopoline, and the alkanolamine salts, in particular those of mono-, di- or trialkanolamines having 2 to 6 carbon atoms in the alkanol radical, such as mono-, di- or triethanolamine, in Consider.
  • aminocarboxylic acids with a total of 2 to 6 carbon atoms such as sarcosine, can also be used to neutralize the carboxyl groups.
  • the polysiloxanes containing anhydride groups are reacted, in particular the polysiloxanes which contain a maleic anhydride or succinic anhydride group as the end group, with amines, the corresponding half-amides are formed.
  • Amines which are preferably used are morpholine or sarcosine.
  • the polysiloxanes containing carboxylic anhydride groups can also with alcohols, for example monohydric C1 to C8 alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, n-octonal, isooctanol or 2-ethylhexanol the corresponding half-ester groups.
  • Alcohols for example monohydric C1 to C8 alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, n-octonal, isooctanol or 2-ethylhexanol the corresponding half-ester groups.
  • Polyhydric alcohols such as glycol or glycerol, can also react with the carboxylic anhydride end groups of the poly
  • aqueous emulsions with a concentration of 5 to 90, preferably 20 to 50% by weight, as can be seen from the examples, are expediently prepared and added to the treatment liquor.
  • the aqueous emulsions obtained are surprisingly stable, so that additional auxiliaries need not be used.
  • solvent-water mixtures with a lower alcohol such as isopropanol / water, ethanol / water or methoxypropanol / water, are useful, for example if dry leather is to be subsequently hydrophobized.
  • the invention also relates to the use of polysiloxanes containing carboxyl groups, the carboxyl groups of which are present in the neutralized form given above, for the hydrophobization of leather, furs and leather substitutes in an aqueous liquor before, during or after retanning without the use of emulsifiers.
  • the actual hydrophobization according to the invention takes place before, during or after retanning with drumming in a suitable device in a conventional manner: ie with liquor lengths of 10 to 2000%, preferably 50 to 200%, based on the fold weight of the leather or the wet weight of the furs , in the case of furs relatively long liquor lengths come into consideration, at temperatures of 20 to 60 ° C., preferably 30 to 50 ° C., the pH values between 4.0 and 8.0, preferably 5.0 to 6, initially 0, lie. The times required are between 20 and 180 minutes, preferably 30 to 90 minutes.
  • the usual fixation of the tannins, dyes and any other tanning aids used is to a pH of 3.0 to 5.0, preferably 3.5 to 4.5, in particular 3.5 to 3, 9 set.
  • the pH is preferably adjusted by adding formic acid.
  • hydrophobization process according to the invention can advantageously be combined with conventional hydrophobizing agents for leather and furs, as are known to the person skilled in the art, for example, on the basis of a paraffin or wax emulsion.
  • the hydrophobization according to the invention can also take place in several stages, partly before, during and after the actual retanning, as can be seen from the application examples b and c.
  • Starting leather is expediently mineral-tanned leather.
  • Vegetable tanning agents and synthetic tanning agents based on phenolic and / or naphthalenesulfonic acid-formaldehyde condensates, polymeric tanning agents based on, for example, acrylates or methacrylates, aldehyde tanning agents or resin tanning agents based on e.g. Melamine-urea or dicyandiamide-formaldehyde condensates are used.
  • the usual acidic, substantive or basic aniline dyes come into consideration as dyes.
  • milling takes place at temperatures of 40 ° C.
  • Chrome-tanned cowhides with a fold thickness of 2 mm, which have been deacidified to a pH of 5, are based on the fold weight with 5% by weight of commercially available mimosa extract and 5% by weight of a commercially available synthetic tanning agent based on phenolsulfonic acid-formaldehyde -Condensation and 1% by weight of a commercially available aniline dye in the tanning drum for 60 minutes.
  • the mixture is then drummed for 60 minutes with 10% by weight of the polysiloxane emulsion given in Example 1 and the working liquor is acidified to a pH of 3.8 using 100% formic acid.
  • the leathers are then washed, mechanically stretched and dried.
  • the leather obtained is soft and supple, has a pleasant feel and excellent dynamic water resistance.
  • Chrome-tanned cowhide with a fold thickness of 1.8 mm and deacidified according to Example a are based on the fold weight, with 4% by weight of a commercially available hydrophobicizing agent based on a paraffin emulsion and 2.5% by weight of the polysiloxane emulsion described in Example 4 for 30 minutes Tumbled in the tanning barrel.
  • the mixture is retanned with 8% by weight of a synthetic tanning agent based on phenolsulfonic acid-formaldehyde condensate and dyed with 1% by weight of aniline dye and then acidified to a pH of 4.0 with 100% of the treatment liquor.
  • a further 2.5% by weight of the polysiloxane emulsion specified in Example 4 are then rolled in for 30 minutes in a fresh bath with 100% liquor. While walking for another 20 minutes, the mixture is acidified to a pH of 3.9, rinsed and the leather is finished in a customary manner.
  • Chromium-tanned cowhide leather with a fold thickness of 1.1 mm and deacidified to a pH of 6.5 are dyed through with 4% by weight of aniline dye and with 8% by weight, a commercially available hydrophobizing agent based on a paraffin emulsion and with 2.5% by weight of the polysiloxane emulsion described in Example 1 pre-greased for 45 minutes.
  • the retanning is carried out using 2% by weight of an acrylic-based polymer tanning agent and 4% by weight of a synthetic tanning agent based on phenolsulfonic acid-formaldehyde condensate.
  • the mixture is then acidified to a pH of 3.8 using a further 6% by weight of a commercially available hydrophobicizing agent based on a paraffin emulsion and 2.5% by weight of the polysiloxane emulsion specified in Example 1, and the leather is acidified to a practical level, as indicated in Example a, completed.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)

Claims (2)

1. Procédé d'hydrophobisation du cuir, de fourrures et de succédanés du cuir, à l'aide d'un polysiloxanne contenant des radicaux carboxyle, sans utilisation conjointe d'émulsifs, caractérisé en ce que les radicaux carboxyle du polysiloxanne se présentent sous forme neutralisée et on laisse agir le polysiloxanne neutralisé, en une proportion de 0,1 à 15% en poids, par rapport au poids drayé du cuir ou au poids mouillé des fourrures, en bain aqueux, à un pH de 4,0 à 8,0 sur les fourrures ou le cuir à traiter, pendant ou après le retannage et on règle ensuite la valeur du pH à 3,0-5,0.
2. Utilisation de polysiloxannes contenant des radicaux carboxyle, dont les radicaux carboxyle se présentent sous forme neutralisée, sans l'utilisation conjointe d'émulsifs, en vue de l'hydrophobisation du cuir, de fourrures et de succédanés du cuir, en bain aqueux, avant ou après le retannage.
EP89100027A 1988-01-12 1989-01-03 Procédé pour rendre hydrophobes le cuir, les fourrures et les cuirs synthétiques Expired - Lifetime EP0324345B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3800629 1988-01-12
DE3800629A DE3800629A1 (de) 1988-01-12 1988-01-12 Verfahren zum hydrophobieren von leder, pelzen und lederaustauschmaterialien

Publications (2)

Publication Number Publication Date
EP0324345A1 EP0324345A1 (fr) 1989-07-19
EP0324345B1 true EP0324345B1 (fr) 1992-04-15

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Family Applications (1)

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EP89100027A Expired - Lifetime EP0324345B1 (fr) 1988-01-12 1989-01-03 Procédé pour rendre hydrophobes le cuir, les fourrures et les cuirs synthétiques

Country Status (6)

Country Link
US (1) US4931062A (fr)
EP (1) EP0324345B1 (fr)
JP (1) JP2735594B2 (fr)
CA (1) CA1285712C (fr)
DE (2) DE3800629A1 (fr)
ES (1) ES2032607T3 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022464A1 (fr) * 1992-04-29 1993-11-11 Chemische Fabrik Stockhausen Gmbh Procede et dispositif d'impermeabilisation de materiaux a structure fibreuse
WO1995022627A2 (fr) * 1994-02-16 1995-08-24 Basf Aktiengesellschaft Procede d'impermeabilisation de cuirs et de peaux avec des polysiloxanes a fonction carboxyle et a structure en peigne
US6007801A (en) * 1996-09-27 1999-12-28 Basf Aktiengesellschaft Use of carboxyl-containing polysiloxanes in cosmetic formulations
US6110230A (en) * 1996-11-13 2000-08-29 Basf Aktiengesellschaft Use of carboxyamide-polysiloxanes for water proofing leather
US6294103B1 (en) 1996-11-07 2001-09-25 3M Innovative Properties Company Use of amphiphilic copolymers containing a fluorinated monomer to impart waterproofness to leather
EP2557181A1 (fr) 2011-08-12 2013-02-13 LANXESS Deutschland GmbH Procédé d'hydrophobisation de substrats contenant des fibres de collagène

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4139090A1 (de) * 1991-11-28 1993-06-03 Stockhausen Chem Fab Gmbh Verwendung von copolymerisaten mit polysiloxan-einheiten zur behandlung von leder und pelzen
DE4234679A1 (de) * 1992-10-14 1994-04-21 Philipp Schaefer Leder, insbesondere solches mit rauher Oberfläche, und Verfahren zum Veredeln von Leder
DE4244951C2 (de) * 1992-12-01 1998-08-06 Minnesota Mining & Mfg Fasersubstrat mit Wasser-, Öl-, Schmutzabweisungsvermögen und Weichgriffigkeit
DE69306578T2 (de) * 1993-10-19 1997-04-10 Minnesota Mining & Mfg Hochleistungszusammensetzungen mit wasser- und ölabweisenden Eigenschaften
DE4415062B4 (de) * 1994-04-29 2004-04-01 Stockhausen Gmbh & Co. Kg Mittel und Verfahren zur Hydrophobierung von Ledern und Pelzen
US5911901A (en) * 1995-10-04 1999-06-15 Hodgson Process Chemicals, Inc. Leather waterproofing method and composition
DE19545689A1 (de) * 1995-12-07 1997-06-12 Henkel Kgaa Verwendung von Silicium-haltigen Terpolymeren zur fettenden Ausrüstung von Leder
DE19629986A1 (de) * 1996-07-25 1998-01-29 Basf Ag Verfahren zum Hydrophobieren von mit Polymergerbstoffen gegerbten Ledern und Pelzfellen
DE69605925T2 (de) 1996-11-07 2000-07-20 Minnesota Mining & Mfg Verwendung amphiphiler Copolymere, enthaltend fluorhaltige Monomer zur wasserfesten Ausrüstung von Leder
FR2772605B1 (fr) * 1997-12-24 2001-01-05 Oreal Compositions cosmetiques contenant une silicone carboxylee et procedes
FR2782637B1 (fr) 1998-08-27 2000-11-24 Oreal Composition capillaire contenant un polycondensat comprenant au moins un motif polyurethanne et/ou polyuree et un polyol
FR2782635B1 (fr) * 1998-08-27 2001-09-14 Oreal Dispositif aerosol contenant un polycondensat comprenant au moins un motif polyurethanne et/ou polyuree
JP2002523439A (ja) 1998-08-27 2002-07-30 ロレアル 少なくとも一のポリウレタン及び／またはポリウレア単位を含む重縮合物を実装してなるエアロゾルディスペンサー
FR2782636B1 (fr) 1998-08-27 2001-09-14 Oreal Compositions contenant un polycondensat comprenant au moins un motif polyurethanne et/ou polyuree et une silicone comprenant au moins une fonction carboxylique
US6525127B1 (en) 1999-05-11 2003-02-25 3M Innovative Properties Company Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates
US7049379B2 (en) * 1999-05-11 2006-05-23 3M Innovative Properties Company Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates
FR2794971B1 (fr) 1999-06-18 2003-08-29 Oreal Composition de cosmetique capillaire sous forme d'emulsion d'eau-dans-silicone comprenant au moins un polymere fixant
DE19959949A1 (de) 1999-12-13 2001-06-21 Bayer Ag Hydrophobierung mit carboxylgruppenhaltigen Polysiloxanen
DE10003322A1 (de) * 2000-01-27 2001-08-02 Bayer Ag Polysiloxane zur Hydrophobierung
JP4469062B2 (ja) * 2000-04-25 2010-05-26 東レ・ダウコーニング株式会社 塩基性アミノ酸変性オルガノポリシロキサンの製造方法
US7025950B2 (en) 2002-05-09 2006-04-11 The Procter & Gamble Company Oral care compositions comprising dicarboxy functionalized polyorganosiloxanes
US7166235B2 (en) 2002-05-09 2007-01-23 The Procter & Gamble Company Compositions comprising anionic functionalized polyorganosiloxanes for hydrophobically modifying surfaces and enhancing delivery of active agents to surfaces treated therewith
DE10250111A1 (de) * 2002-10-28 2004-05-06 Bayer Ag Chromfreies, wasserdichtes Leder
DE10304330A1 (de) 2003-02-04 2004-08-12 Goldschmidt Ag Lineare carboxyfunktionelle Organosiloxanylderivate und deren Verwendung zur Behandlung der Oberflächen von Leder
DE102006027400A1 (de) * 2006-06-13 2007-12-20 Wacker Chemie Ag Verfahren zur Behandlung von proteinhaltigen, faserartigen Stoffen mit beta-Ketocarbonyl-funktionellen Siloxanpolymeren
US8398964B2 (en) * 2009-07-28 2013-03-19 Shin-Etsu Chemical Co., Ltd. Organopolysiloxane having amide group, and cosmetic material containing same
CN103038274B (zh) 2010-05-28 2015-03-25 迈图高新材料有限责任公司 用聚有机硅氧烷使纤维材料疏水化
CN102605112A (zh) * 2012-03-31 2012-07-25 陕西科技大学 一种结合型氨基硅油皮革加脂剂及其制备方法
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
NL2027334B1 (en) 2021-01-18 2022-07-25 Stahl Int B V Composition and process for waterproofing leather

Family Cites Families (3)

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Publication number Priority date Publication date Assignee Title
US3116965A (en) * 1963-08-27 1964-01-07 Union Carbide Corp Silatrioxane tanned leather and the production thereof
US4501619A (en) * 1983-11-14 1985-02-26 Dow Corning Corporation Aqueous emulsions of carboxyl-containing silicone fluids and a method for their preparation
DE3529869A1 (de) * 1985-08-21 1987-02-26 Basf Ag Verfahren zum hydrophobieren von leder und pelzen

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022464A1 (fr) * 1992-04-29 1993-11-11 Chemische Fabrik Stockhausen Gmbh Procede et dispositif d'impermeabilisation de materiaux a structure fibreuse
WO1995022627A2 (fr) * 1994-02-16 1995-08-24 Basf Aktiengesellschaft Procede d'impermeabilisation de cuirs et de peaux avec des polysiloxanes a fonction carboxyle et a structure en peigne
AU683723B2 (en) * 1994-02-16 1997-11-20 Basf Aktiengesellschaft Water-proofing process for leathers and pelts by comb-like carboxylated polysiloxanes
US5702490A (en) * 1994-02-16 1997-12-30 Basf Aktiengesellschaft Water repellent treatment of leather and skins with polysiloxanes functionalized with carboxyl groups in a comb-like manner
US6007801A (en) * 1996-09-27 1999-12-28 Basf Aktiengesellschaft Use of carboxyl-containing polysiloxanes in cosmetic formulations
US6294103B1 (en) 1996-11-07 2001-09-25 3M Innovative Properties Company Use of amphiphilic copolymers containing a fluorinated monomer to impart waterproofness to leather
US6110230A (en) * 1996-11-13 2000-08-29 Basf Aktiengesellschaft Use of carboxyamide-polysiloxanes for water proofing leather
EP2557181A1 (fr) 2011-08-12 2013-02-13 LANXESS Deutschland GmbH Procédé d'hydrophobisation de substrats contenant des fibres de collagène
WO2013023980A1 (fr) 2011-08-12 2013-02-21 Lanxess Deutschland Gmbh Procédé d'hydrophobisation de substrats contenant des fibres de collagène

Also Published As

Publication number Publication date
DE58901120D1 (de) 1992-05-21
JPH01215900A (ja) 1989-08-29
US4931062A (en) 1990-06-05
JP2735594B2 (ja) 1998-04-02
CA1285712C (fr) 1991-07-09
EP0324345A1 (fr) 1989-07-19
ES2032607T3 (es) 1993-02-16
DE3800629A1 (de) 1989-07-20

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