EP0087799B1 - Process for the liquoring and simultaneous water-proofing of leather, fur and leather substitutes - Google Patents

Process for the liquoring and simultaneous water-proofing of leather, fur and leather substitutes Download PDF

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Publication number
EP0087799B1
EP0087799B1 EP83101962A EP83101962A EP0087799B1 EP 0087799 B1 EP0087799 B1 EP 0087799B1 EP 83101962 A EP83101962 A EP 83101962A EP 83101962 A EP83101962 A EP 83101962A EP 0087799 B1 EP0087799 B1 EP 0087799B1
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Prior art keywords
carbon atoms
saturated
fatty acid
unsaturated
stuffing
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German (de)
French (fr)
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EP0087799A1 (en
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Heribert Dr. Schmitz
Wolfgang Eberhardt
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Muenzing Chemie GmbH
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    • 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

Abstract

1. A method of stuffing and at the same time water-proofing leather, fleece and leather substitutes whereby the material to be stuffed and waterproofed is treated in an aqueous liquor which contains a stuffing and waterproofing agent, characterised in that the stuffing and waterproofing agent consists in a compound of general formula see diagramm : EP0087799,P4,F2 wherein X, R, M and z have the following meanings : - X is a straight or branched, saturated or unsaturated, cyclic, acyclic or aromatic, possibly also heteroatom, containing diol with 2 to 16 carbon atoms or a condensation product of ethylene oxide and/or propylene oxide and/or butylene oxide with 2 to 6 moles alkylene oxide or a mixture of said diols ; R is a hydroxy compound acting as an esterification compound, i.e. a straight or branched, saturated or unsaturated alcohol with 12 to 18 carbon atoms, or one of said alcohols, condensed with 1 to 6 mols alkylene oxide, or a phenol or alkyl phenol with 6 to 30 carbon atoms, or one of said phenols and alkyl phenols, condensed with 1 to 12 moles ethylene oxide, or a saturated or unsaturated fatty acid ester, the fatty acid radical containing 8 to 22 carbon atoms and the ester components being polyalkylene oxides with 1 to 6 mols ethylene oxide, or a saturated or unsaturated fatty acid mono- or diglyceride with 8 to 22 carbon atoms per fatty acid radical, or a saturated or unsaturated, primary or secondary fatty amine with 8 to 22 carbon atoms per alkyl radical, condensed with 1 to 24 mols alkylene oxide, or a saturated or unsaturated fatty acid amide with 8 to 22 carbon atoms, condensed with 1 to 24 mols alkylene oxide ; M is a monovalent metal cation, ammonium ion or an organic ammonium compound ; z is an integer from 1 to 5.

Description

Die Erfindung betrifft ein Verfahren zum Fetten und gleichzeitigen Hydrophobieren von Leder, Pelz und Lederaustauschstoffen nach dem Oberbegriff des Patentanspruchs 1.The invention relates to a method for greasing and simultaneously hydrophobizing leather, fur and leather substitutes according to the preamble of claim 1.

In der CH-A-300 953 ist ein solches Verfahren beschrieben, wobei als Mittel zur Durchführung des Verfahrens eine Stoffgruppe angegeben ist, die durch eine allgemeine Formel repräsentiert ist. Es wurde festgestellt, daß zahlreiche Verbindungen, die unter diese Formel fallen, für das Fetten und gleichzeitige Hydrophobieren von Leder nicht oder nur in sehr unbefriedigendem Ausmaß geeignet sind.Such a process is described in CH-A-300 953, a group of substances which is represented by a general formula being indicated as the means for carrying out the process. It has been found that numerous compounds which fall under this formula are unsuitable or only to a very unsatisfactory extent for the greasing and simultaneous waterproofing of leather.

Es ist Aufgabe der Erfindung, das gattungsgemäße Fettungs- und Hydrophobierverfahren zu verbassern und spezielle Mittel anzugeben, mit denen sich das Verfahren erfolgreich durchführen läßt.It is an object of the invention to improve the generic greasing and waterproofing process and to provide special agents with which the process can be carried out successfully.

Die Aufgabe wird erfindungsgemäß durch die kennzeichnenden Merkmale des Patentanspruchs 1 gelöst.The object is achieved by the characterizing features of claim 1.

Die nachstehende Beschreibung dient im Zusammenhang mit einigen Beispielen der weiteren Erläuterung der Erfindung.The following description is used in conjunction with some examples to further explain the invention.

Zur Herstellung der Phosphorsäureester der allgemeinen, im Patentanspruch 1 angegebenen Formel geht man vorzugsweise in einem ersten Reaktionsschrit von Phosphoroxidchlorid (POC13) und einem Diol X aus, die unter Abspaltung von Chlorwasserstoff kondensiert werden. Das molVerhältnis Phosphoroxidchlorid zu Diol beträgt 2 zu 1 bis 1.1 zu 1, vorzugsweise 1.5 zu 1. Man erhält durch die Kondensation Verbindungen der allgemeinen Formel (1), worin z eine ganze Zahl von 1-5 ist.

Figure imgb0001
To prepare the phosphoric acid esters of the general formula given in claim 1, it is preferable to start in a first reaction step from phosphorus oxychloride (POC1 3 ) and a diol X, which are condensed with elimination of hydrogen chloride. The molar ratio of phosphorus oxychloride to diol is 2 to 1 to 1.1 to 1, preferably 1.5 to 1. The condensation gives compounds of the general formula (1) in which z is an integer from 1-5.
Figure imgb0001

Als Diol X kommen infrage lineare oder verzweigte, gesättigte oder ungesättigte, acyclische Diole mit 2-16, vorzugsweise 2-10 C-Atomen, wie z.B. Butandiol-1.4, Hexandiol-2.5, Hexandiol-1.6 oder Decandiol-1.10, Buten-2-diol-1.4 oder Hexin-3-diol-2.5, oder cyclische Diole, wie z.B. Cyclohexandiol-1.4, oder aromatische Diole, wie z.B. Bisphenol A. Außerdem kann X sein ein Kondensationsprodukt des Ethylenoxids und/ oder des Propylenoxids und/oder des Butylenoxids mit 2-8 mol Alkylenoxid, wie z.B. Tripropylenglykol oder Polyethylenglykol 200.Suitable diol X are linear or branched, saturated or unsaturated, acyclic diols with 2-16, preferably 2-10, carbon atoms, such as e.g. Butanediol-1.4, Hexanediol-2.5, Hexanediol-1.6 or Decanediol-1.10, Butene-2-diol-1.4 or Hexin-3-diol-2.5, or cyclic diols, e.g. Cyclohexanediol-1.4, or aromatic diols, e.g. Bisphenol A. In addition, X can be a condensation product of ethylene oxide and / or propylene oxide and / or butylene oxide with 2-8 moles of alkylene oxide, e.g. Tripropylene glycol or polyethylene glycol 200.

Die Phosphorverbindung der allgemeinen Formel (1) wird in einem zweiten Reaktionsschritt unter Chlorwasserstoffabspaltung mit einer Hydroxiverbindung R kondensiert (verestert).The phosphorus compound of the general formula (1) is condensed (esterified) with a hydroxyl compound R in a second reaction step with elimination of hydrogen chloride.

Als Hydroxiverbindung R kommen infrage lineare oder verzweigte, gesättigte oder ungesättigte Alkohole mit 12-18 C-Atomen, oder die vorgenannten Alkohole, kondensiert mit 1-6 mol Alkylenoxid, wie z.B. Oleylalkohol, TaIgfettalkohol, synthetische Alfol-Alkohole, Isooctadecylalkohol oder Oleylalkohol mit 4 mol Ethylenoxid, ferner Phenole oder Alkylphenole mit 6-30 C-Atomen, wie z.B. Octylphenol, Nonylphenol, Dinonyphenol, Dodecylphenol, oder die entsprechenden ethoxilierten Phenole und Alkyphenole (1-12 mol Ethylenoxid).Possible hydroxyl compounds R are linear or branched, saturated or unsaturated alcohols with 12-18 C atoms, or the abovementioned alcohols condensed with 1-6 mol alkylene oxide, such as e.g. Oleyl alcohol, tallow fatty alcohol, synthetic Alfol alcohols, isooctadecyl alcohol or oleyl alcohol with 4 mol ethylene oxide, furthermore phenols or alkylphenols with 6-30 C-atoms, e.g. Octylphenol, nonylphenol, dinonyphenol, dodecylphenol, or the corresponding ethoxylated phenols and alkylphenols (1-12 mol ethylene oxide).

Als Hydroxiverbindung R finden auch gesättigte oder ungesättigte Fettsäureester Anwendung, wobei der Fettsäurerest 8-22 C-Atome enthält und die Ester-Komponente Polyalkylenoxide mit 1-6 mol Ethylenoxid sind, wie z.B. Talgfettsäure mit 6 mol Ethylenoxid oder Ölsäure, verestert mit Polyethylenglykol 200, oder es findet ein gesättigtes oder ungesättigtes Mono- bzw. Diglyzerid einer Fettsäure mit 8-22 C-Atomen pro Fettsäurerest, wie z.B. Ölsäuremonoglyzerid Anwendung. Auch alkoxilierte, gesättigte oder ungesättigte Fettamine mit 8-22 C-Atomen pro Alkylrest und kondensiert mit 1-24 mol Alkylenoxid, wie Fettsäuremono- bzw. dialkanolamide, können verwendet werden. Beispiele hierfür sind Kokosfettamin mit 12 mol Ethylenoxid, Talgfettsäureamid mit 10 mol Ethylenoxid, Ölsäureamid mit 4 mol Ethylenoxid und Kokosfettsäurediethanolamid.Saturated or unsaturated fatty acid esters are also used as the hydroxyl compound R, the fatty acid residue containing 8-22 carbon atoms and the ester component being polyalkylene oxides with 1-6 mol ethylene oxide, such as e.g. Tallow fatty acid with 6 mol ethylene oxide or oleic acid, esterified with polyethylene glycol 200, or a saturated or unsaturated mono- or diglyceride of a fatty acid with 8-22 carbon atoms per fatty acid residue, e.g. Oleic acid monoglyceride application. Alkoxylated, saturated or unsaturated fatty amines with 8-22 carbon atoms per alkyl radical and condensed with 1-24 mol alkylene oxide, such as fatty acid mono- or dialkanolamides, can also be used. Examples include coconut fatty amine with 12 mol ethylene oxide, tallow fatty acid amide with 10 mol ethylene oxide, oleic acid amide with 4 mol ethylene oxide and coconut fatty acid diethanolamide.

In einem dritten Reaktionsschritt werden die noch verbliebenden P-CI-Bindungen des ursprünglichen Phosphoroxidchlorids (POCI3) mit einer Base M-OH abneutralisiert.In a third reaction step, the remaining P-CI bonds of the original phosphorus oxide chloride (POCI 3 ) are neutralized with a base M-OH.

M steht für ein Alkalimetallkation, z.B. Na+, K+ oder für das Ammonium-lon oder für eine organische, cyclische oder acyclische Ammoniumverbindung, wie z.B. Cyclohexylammonium-, Triethylammonium- oder Monoethanolammoniumlon.M stands for an alkali metal cation, for example Na + , K + or for the ammonium ion or for an organic, cyclic or acyclic ammonium compound, such as for example cyclohexylammonium, triethylammonium or monoethanolammonium ion.

Die zur Fettung und Hydrophobierung verwendete wässrige Flotte kann durch Einrühren des erfindungsgemäß verwendeten Fettungs- und Hydrophobierungsmittels in warmes Wasser (ca. 50°C; 3 Teile Wasser auf 1 Teil Lederbehandlungsmittel) hergestellt werden. Eine solche Flotte ist ausreichend stabil und wird zum Lickern (d.h. Behandeln in wässrigem System) von chromgegerbten oder vegetabil und/oder synthetisch nachgegerbten ledern verwendet. Ein besonderer Vorteil des erfindungsgemäßen Verfahrens besteht in der sehr starken Affinität der angegebenen Fettungs- und Hydrophobierungsmittel zur Faser. Dies zeigt sich z.B. bei der Extraktion mit Dichlormethan (nach DIN 53306), bei der das Lederbehandlungsmittel praktisch nicht von der Faser extrahiert werden kann.The aqueous liquor used for oiling and waterproofing can be prepared by stirring the oiling and waterproofing agent used according to the invention into warm water (approx. 50 ° C .; 3 parts water to 1 part leather treatment agent). Such a liquor is sufficiently stable and is used for licking (i.e. treating in an aqueous system) chrome-tanned or vegetable and / or synthetically retanned leathers. A particular advantage of the process according to the invention is the very strong affinity of the specified fatliquoring and hydrophobicizing agents for the fiber. This can be seen e.g. during extraction with dichloromethane (according to DIN 53306), in which the leather treatment agent can practically not be extracted from the fiber.

Die Leder, die nach dem beanspruchten Verfahren behandelt werden, zeichnen sich durch gute Weichheit und Geschmeidigkeit und angenehmen Griff aus.The leathers that are treated according to the claimed process are characterized by good softness and suppleness and a pleasant feel.

Der besondere Vorteil der nach dem erfindungsgemäßen Verfahren behandelten Leder liegt in der gleichzeitig erreichten, außergewöhnlich hohen dynamischen Wasserfestigkeit.The particular advantage of the leather treated by the process according to the invention lies in the extraordinarily high dynamic water resistance achieved at the same time.

Beispiel 1example 1

In üblicher Weise hergestelltes Chromnarbenleder wird mit 100% Flotte (= Wasser), 1% Farbstoff und 5% Lederbehandlungsmittel gemäß Formel im Patentanspruch 1 praxisgerecht gelikkert und aufgearbeitet. Die voranstehenden Prozentangaben beziehen sich auf das Ledergewicht. In der Formel bedeuten dabei X = Hexandiol-1.6, R = Oleylalkohol, M = Na und z = 2.Chrome grain leather produced in the usual way is treated with 100% liquor (= water), 1% dye and 5% leather treatment agent Formula in claim 1 practiced and worked up in a practical manner. The percentages above refer to the weight of the leather. In the formula, X = 1.6-hexanediol, R = oleyl alcohol, M = Na and z = 2.

Die erhaltenen Leder sind sehr weich und geschmeidig, besitzen einen trockenen seidigen Griff und zeigen eine hervorragende dynamische Wasserfestigkeit bei Prüfung auf dem "Bally-Penetrometer" (gemäß IUP/10; "Das Leder", 1961, 38).The leathers obtained are very soft and supple, have a dry silky feel and show excellent dynamic water resistance when tested on the "Bally penetrometer" (according to IUP / 10; "Das Leder", 1961, 38).

Wasserdurchtritt nach Minuten: >480 Minuten. Wasseraufnahme nach 480 Minuten: 14%.Water penetration after minutes:> 480 minutes. Water absorption after 480 minutes: 14%.

Beispiel 2Example 2

Chromnarbenleder wird in üblicher Weise mit 2% eines synthetischen Gerbstoffes nachgegerbt, gefärbt und mit 5% Lederbehandlungsmittel gemäß Formel im Patentanspruch 1 gelickert. Die voranstehenden Prozentangaben beziehen sich auf das Ledergewicht. In der Formel bedeuten dabei X = Ethylenglykol, R = Kokosfettalkohol, M = Ammonium und z = 3.Chrome grain leather is retanned in the usual way with 2% of a synthetic tanning agent, dyed and licked with 5% leather treatment agent according to the formula in claim 1. The percentages above refer to the weight of the leather. In the formula, X = ethylene glycol, R = coconut fatty alcohol, M = ammonium and z = 3.

Nach praxisgerechter Aufarbeitung wird ein weiches, gleichmäßig gefärbtes Leder mit großer Wasserfestigkeit erhalten.After practical processing, a soft, evenly colored leather with great water resistance is obtained.

Wasserdurchtritt nach Minuten: >480 Minuten. Wasseraufnahme nach 480 Minuten: 16%.Water penetration after minutes:> 480 minutes. Water absorption after 480 minutes: 16%.

Beispiel 3Example 3

In bekannter Weise wird Chromnarbenleder mit 20% vegetabilischen Gerbstoffen nachgegerbt und mit 6% Lederbehandlungsmittel gemäß Formel im Patentanspruch 1 in 100% Flotte gelickert. Die voranstehenden Prozentangaben beziehen sich auf das Ledergewicht. In der Formel bedeuten dabei X = Butandiol-1.4, R = Nonylphenolpolyglykolether (5 mol EO), M = Na und z = 1.In a known manner, chrome grain leather is retanned with 20% vegetable tanning agents and licked with 6% leather treatment agent according to the formula in claim 1 in 100% liquor. The percentages above refer to the weight of the leather. In the formula, X = 1,4-butanediol, R = nonylphenol polyglycol ether (5 mol EO), M = Na and z = 1.

Nach Aufarbeitung wird ein weiches und sehr wasserfestes Leder erhalten.After working up, a soft and very waterproof leather is obtained.

Wasserdurchtritt nach Minuten: >480 Wasseraufnahme nach 480 Minuten: 17%.Water penetration after minutes:> 480 Water absorption after 480 minutes: 17%.

In allen Beispielen werden dem Lederfettungs-und Hydrophobierungsmittel je nach Bedarf übliche Lederadditive zugefügt, beispielsweise neutrale Lederbehandlungsmittel wie Öle, Fette, chlorierte Öle und Fette, Chlorparaffine. höhermolekulare Fettalkohole, Fettsäuren, Fettsäureester sowie Kohlenwasserstoffe, ferner anionische Emulgatoren beispielsweise sulfierte Kohlenwasserstoffe, sulfierte native Fette oder Öle, oder sulfierte Fettsäuren und Fettsäureester, und/oder schließlich nichtionogene Emulgatoren, beispielsweise Fettalkoholethoxilate oder Alkylphenolethoxilate.In all examples, customary leather additives are added to the leather greasing and waterproofing agent as required, for example neutral leather treatment agents such as oils, fats, chlorinated oils and fats, chlorinated paraffins. High molecular weight fatty alcohols, fatty acids, fatty acid esters and hydrocarbons, furthermore anionic emulsifiers, for example sulfated hydrocarbons, sulfated native fats or oils, or sulfated fatty acids and fatty acid esters, and / or finally nonionic emulsifiers, for example fatty alcohol ethoxylates or alkylphenol ethoxylates.

Claims (4)

1. A method of stuffing and at the same time water-proofing leather, fleece and leather substitutes whereby the material to be stuffed and waterproofed is treated in an aqueous liquor which contains a stuffing and waterproofing agent, characterised in that the stuffing and waterproofing agent consists in a compound of general formula
Figure imgb0004
wherein X, R, M and z have the following meanings:-
X is a straight or branched, saturated or unsaturated, cyclic, acyclic or aromatic, possibly also heteroatom, containing diol with 2 to 16 carbon atoms or a condensation product of ethylene oxide and/or propylene oxide and/or butylene oxide with 2 to 6 moles alkylene oxide or a mixture of said diols;
R is a hydroxy compound acting as an esterification compound, i.e. a straight or branched, saturated or unsaturated alcohol with 12 to 18 carbon atoms,
or one of said alcohols, condensed with 1 to 6 mols alkylene oxide,
or a phenol or alkyl phenol with 6 to 30 carbon atoms,
or one of said phenols and alkyl phenols, condensed with 1 to 12 moles ethylene oxide,
or a saturated or unsaturated fatty acid ester, the fatty acid radical containing 8 to 22 carbon atoms and the ester components being polyalkylene oxides with 1 to 6 mols ethylene oxide, or a saturated or unsaturated fatty acid mono- or diglyceride with 8 to 22 carbon atoms per fatty acid radical, or a saturated or unsaturated, primary or secondary fatty amine with 8 to 22 carbon atoms per alkyl radical, condensed with 1 to 24 mols alkylene oxide,
or a saturated or unsaturated fatty acid amide with 8 to 22 carbon atoms, condensed with 1 to 24 mols alkylene oxide;
M is a monovalent metal cation, ammonium ion or an organic ammonium compound;
z is an integer from 1 to 5.
2. A method according to Claim 1, characterised in that neutral leather treatment agents such as, e.g. oils, fats, chlorinated oils and fats, chloroparaffins, higher molecular fatty alcohols, fatty acids and fatty acid esters, as well as hydrocarbons are added to the stuffing and waterproofing agent.
3. A method according to Claim 1 or 2, characterised in that anionic emulsifiers, particularly sulphided hydrocarbons, sulphided true fats or oils or sulphided fatty acids and fatty acid esters are also added to the stuffing and waterproofing agent.
4. A method according to Claims 1, 2 or 3, characterised in that nonionogenic emulsifiers, particularly fatty alcohol ethoxylates or alkyl phenol oxylates are subsequently added to the stuffing and waterproofing agent.
EP83101962A 1982-03-03 1983-02-28 Process for the liquoring and simultaneous water-proofing of leather, fur and leather substitutes Expired EP0087799B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83101962T ATE22929T1 (en) 1982-03-03 1983-02-28 METHOD OF LUBRICATION AND SIMULTANEOUSLY HYDROPHOBIZING LEATHER, FUR AND LEATHER REPLACEMENT MATERIALS.

Applications Claiming Priority (2)

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DE3207562 1982-03-03
DE19823207562 DE3207562A1 (en) 1982-03-03 1982-03-03 METHOD FOR FAT AND SIMULTANEOUSLY HYDROPHOBIZING LEATHER, FUR AND LEATHER EXCHANGERS

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EP0087799A1 EP0087799A1 (en) 1983-09-07
EP0087799B1 true EP0087799B1 (en) 1986-10-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9382504B2 (en) 2008-12-19 2016-07-05 3M Innovative Properties Company Composition and method to provide stain release and stain repellency properties to substrates

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2559784B1 (en) * 1984-02-22 1987-07-10 Sandoz Sa PROCESS FOR FEEDING TANNED LEATHER AND TANNED SKINS
DE3504308A1 (en) * 1984-02-22 1985-08-22 Sandoz-Patent-GmbH, 7850 Lörrach Process for the simultaneous fat-liquoring and water-repellent finishing of tanned leather
DE4435399A1 (en) * 1994-10-04 1996-04-11 Henkel Kgaa Leather and fur lubricants
EP1621640B1 (en) * 2004-07-13 2006-10-04 Zschimmer & Schwarz GmbH & Co KG Chemische Fabriken Agent for the hydrophobic treatment of leather
RU2748944C1 (en) * 2020-08-31 2021-06-02 Елена Николаевна Заблоцкая Method for processing hide leather fabric

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
CH300953A (en) * 1949-01-12 1954-08-31 Metallgesellschaft Ag Process for the production of supple leather.
US3934975A (en) * 1971-12-10 1976-01-27 Diamond Shamrock Corporation Leather treating process
US4018559A (en) * 1974-06-14 1977-04-19 Diamond Shamrock Corporation Non-rewet leather and method of producing same
DE2517057C3 (en) * 1975-04-17 1982-10-21 Chemische Fabrik Stockhausen GmbH, 4150 Krefeld Process for improving the mechanical and grip properties of mineral-tanned leathers or fur skins or clothing made from them

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9382504B2 (en) 2008-12-19 2016-07-05 3M Innovative Properties Company Composition and method to provide stain release and stain repellency properties to substrates

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EP0087799A1 (en) 1983-09-07
DE3207562C2 (en) 1988-06-23
ATE22929T1 (en) 1986-11-15
DE3207562A1 (en) 1983-09-15

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