EP0209780B1 - Agent de traitement du cuir et son utilisation - Google Patents

Agent de traitement du cuir et son utilisation Download PDF

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Publication number
EP0209780B1
EP0209780B1 EP86109234A EP86109234A EP0209780B1 EP 0209780 B1 EP0209780 B1 EP 0209780B1 EP 86109234 A EP86109234 A EP 86109234A EP 86109234 A EP86109234 A EP 86109234A EP 0209780 B1 EP0209780 B1 EP 0209780B1
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EP
European Patent Office
Prior art keywords
denotes
alkyl
substituted
alkylene
integer
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
Application number
EP86109234A
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German (de)
English (en)
Other versions
EP0209780A2 (fr
EP0209780A3 (en
Inventor
Harro Dr. Träubel
Manfred Dr. Dietrich
Hans-Werner Müller
Günther Held
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Bayer AG
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Bayer AG
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Filing date
Publication date
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Publication of EP0209780A3 publication Critical patent/EP0209780A3/de
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65125—Compounds containing ester groups
    • 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
    • C14C3/00—Tanning; Compositions for tanning
    • 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
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • 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
    • C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6138—Polymerisation products of glycols, e.g. Carbowax, Pluronics
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6492—(Thio)urethanes; (Di)(thio)carbamic acid derivatives; Thiuramdisulfide
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins

Definitions

  • From DE-OS2 626 430 is the use of compounds obtained by the condensation of carboxylic acids with compounds containing hydroxy or amino groups in a molar ratio are produced, for example the carboxylic acids of the formulas (I) and (II), known as tanning agents or retanning agents.
  • the (post) tanning with compounds containing amino groups and containing urethane groups is e.g. described in DE-OS 2 416 485 and EP-PS 0 001 067.
  • amino-containing polyethers in leather dyeing is e.g. from GB-PS 705 335, US-PS 3 334 960, US-PS 4 272 243 and DE-OS 2 539 671 known.
  • the leather treatment compositions according to the invention preferably contain components a) and b) in a weight ratio of 5-95: 95-5. For example, they are used as aqueous solutions.
  • the pH of the ready-to-use aqueous solutions is 1.5-10, especially 3.5-7.5. It can be adjusted by adding acids or alkalis.
  • the preferred total concentration of the mixture components a) and b) in the aqueous solutions is 20-60% by weight.
  • the molecular weights of the carboxylic acids (I) and (11) are between 170 and 100,000. Preference is given to products which are more than 90% in the molecular weight range between 170 and 10,000 and particularly preferably between 300 and 10,000.
  • the carboxylic acids (I) and (11) and preferred starting products are described in DE-OS 2 626 430.
  • the compounds b) containing amino groups can also contain ether, ester, carboxamide and / or urethane groups. They are known from the literature mentioned above. Their preferred molecular weights are 300-12,000, especially 300-3000.
  • Components b) include, in particular, polyethers containing amino groups, which are prepared by adding ethylene oxide and / or propylene oxide to mono-, di- or polyamines having primary or secondary amino groups or to alkanolamines. They usually have 1-6 hydroxyl groups.
  • Monoalkyl and dialkylamines with C 1 -C 18 alkyl groups Monoalkyl and dialkylamines with C 1 -C 18 alkyl groups, cycloaliphatic amines such as cyclohexylamine and homologues, aniline and N-alkylanilines and aniline derivatives substituted on the benzene nucleus.
  • Ethylene diamine diethylene triamine, triethylene tetramine, 1,2- and 1,3-propylene diamine and corresponding dipropylene triamines and tripropylene tetramines, 1,4-diaminobutane, 1,6-diaminohexane, 3-methyl-1,5-diaminopentane, 1,8- Diaminooctane, trimethyl-1,6-diaminohexane (mixture of isomers 2,2,4 and 2,4,4), 3,3'-bisaminopropyl-methylamine, N, N'-bis - 2-aminomethylpiperazine, 1-amino-3 , 3,5-trimethyl-5-aminomethylcyclohexane, 4,4'-diamino-dicyclohexylmethane and propane, 1,4-diaminocyclohexane, 2,4- and 2,6-hexahydrotoluenediamine, 3,3'-dimethyl
  • alkanolamines The following may be mentioned as alkanolamines:
  • Ethanolamine diethanolamine, propanolamine, di-propanolamine, dibutanolamine, N-methyldiethanolamine, N-dimethylethanolamine, N-diethylethanolamine and triethanolamine.
  • Oligourethanes containing amino groups may also be mentioned as preferred components b). They are made by reacting polyisocyanates such as 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate, 1-isocyanato-3, 3, 5-trimethyl -5-isocyanatomethyl-cyclohexane, 2,4- and 2,6-hexahydrotoluenediisocyanate, hexahydro-1,3- and -1,4-phenylene diisocyanate, perhydro-2,4'- and -4,4'-diphenylmethane diisocyanate, 1,3- and 1,4-phenylene diisocyanate, 2,4- and 2,6-tolylene diisocyanate, diphenylmethane-2,4'- and -4,4'-d
  • Particularly preferred components b) are those of the formula
  • R 3 and R 4 are hydrogen or methyl
  • R 5 is C 2 -C 6 alkylene, e 0-10 and f 1-100, and their reaction products with diisocyanates.
  • the processes for leather treatment are carried out according to known methods in, for example, tanning drums or tanning mixers.
  • the temperatures are generally 10-90 ° C, preferably 20-60 ° C.
  • the aqueous treatment liquors advantageously contain a total of 0.5-20% by weight of components a) and b).
  • the novel agents can g at different points of Lederbehandlun or -Fabrication be used. For example, they can be used for retanning chrome and vegetable tanned leather or simultaneously with chrome tanning or replacement tanning agents. However, they can also be used in the dyeing liquor or for greasing.
  • the joint treatment with the anionic compounds a) and the cationic compounds b) balances out different charge ratios on the leather surface and prevents deeper penetration into the leather. This achieves an effect that is known as gloss lubrication in the leather industry.
  • dyeings with a high level of levelness, brilliance and depth and a good removal of the dyeing liquor are achieved.
  • Soft, smooth leather with a good grain throw is obtained.
  • components a) and b) penetrate deeply into the leather when used individually, as is known, and cause an unevenly charged leather surface. This makes the colorations less important.
  • a glass bulb with a device for Azeotropic drainage 1117 g of diethylethanolamine and 1500 ml of toluene are placed and the air is replaced by nitrogen.
  • 100 g of 50% aqueous potassium hydroxide solution are added at 80 ° C. and 66 g of water are removed from the reaction mixture at 100-115 ° C. by azeotropic distillation.
  • 8883 g of ethylene oxide are then slowly metered in at 90-100 ° C. and 1.4-1.6 bar nitrogen and the mixture is subsequently stirred at 100 ° C. for 3 hours.
  • the alkaline reaction product is mixed with 1000 g of water and neutralized with 350 g of a 12.5% aqueous sulfuric acid.
  • 900 g of diethylethanolamine are placed in a glass flask and the air is replaced by nitrogen.
  • 100 g of 50% aqueous potassium hydroxide solution are added at 80 ° C. and 66 g of water are removed from the reaction mixture at 100 ° C. by vacuum distillation.
  • 6946 g of propylene oxide are then slowly metered in at 100 to 105 ° C. and 1.4-1.6 bar nitrogen.
  • the mixture is stirred at 105 ° C for 4 hours.
  • 1138 g of phthalic anhydride are added. After a further 2 hours, 1015 g of ethylene oxide are slowly metered in at 105 ° C.
  • a condensation product prepared according to DE-OS 2 626 430 from 1 mol of octaethylene glycol and 2 mol of phthalic anhydride are dissolved in 1500 g of water.
  • 1000 g (0.81 mol) of an oligourethane prepared according to DE-AS 2 504 081, consisting of 2 mol octaethylene glycol, 1 mol N-propyl-di-propanolamine and 1.8 mol 2,4- / 2,6, are added to this solution -Toluyien diisocyanate.
  • the resulting hydrosol is adjusted to pH 9 with formic acid.
  • the percentages relate to the weight of the leather.
  • the liquor is drained off, rinsed at 40 ° C. for 10 minutes, 50% 40 ° C. warm water is added, and after 20 minutes 2% of the mixture according to Example 2.1, 2.2, 2.3 or 2.4, with 4% added self-dulling chrome tanning dye ( O BAY-CHROM CL), adds 1% sodium formate after 60 minutes and 2% sodium bicarbonate after 10 minutes, runs for 60 minutes, greases, drains off the rinsing and rinses.
  • O BAY-CHROM CL self-dulling chrome tanning dye
  • the chrome tanning described above is carried out without adding a mixture according to the invention.
  • the addition of 1% of the mixture according to Example 2.1, 2.2, 2.3 or 2.4 takes place only in the dye liquor after the dyeing.
  • the after-treatment time is 20 minutes.
  • the percentages relate to the fold weight.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Coloring (AREA)

Claims (8)

1. Agents pour le traitement du cuir, caractérisés en ce qu'ils contiennent un mélange de
a) un acide carboxylique de formule générale
Figure imgb0032
dans laquelle
X représente un reste de formule
Figure imgb0033
dans laquelle
a et b représentent un nombre entier de 1 à 100
Z représente un groupe NR, ou un atome O ou S et
R1 est un atome d'hydrogène ou un groupe alky- lene en C1-C4, qui peut être substitué par OH ou alcoxy en C1-C4,
R représente un groupe alkylène en Ci ou C2 qui peut être substitué par NH2, -CH=CH-, phénylène, qui peut être substitué par alkyle en C1-C4, ou une liaison directe et
R' représente un groupe alkylène en C2-C20, qui peut être interrompu par
Figure imgb0034
un groupe cyclohexylène ou un groupe dicyclohexy- lèneméthane, ou un reste de formule
Figure imgb0035
dans laquelle
Z, R et R' ont la même signification que dans la formule 1,
c est égal à 0 ou un entier de 1 à 100,
R" représente un groupe alkylène en C1-C20 ou phénylène, qui peut être substitué par alkylène en C1-C4, ou de formule générale
Figure imgb0036
dans laquelle
Z, R, R' et c ont la même signification que précédemment,
k est un entier de 1 à 6,
1 est égal à 0 ou à un entier de 1 à 5,
la somme k+I est au plus égale à 6,
R"' représente un reste alkylène de valence k+l et
RlV représente un groupe alkyle en C1-C12, un groupe phényle qui peut être substitué par alkyle en C1-C4, ou un groupe de formule
Figure imgb0037
où RV représente un groupe alkyle en C1-C12, et le nombre des groupes carboxyles dans (1) et (II) est supérieur au nombre des groupes amino, et de
b) un composé contenant au moins un groupe amino primaire, secondaire ou tertiaire, d'un poids moléculaire de 200-20 000.
2. Agents selon la revendication 1, caractérisés en ce qu'ils contiennent les composants a) et b) dans le rapport de 5-95:95-5 en poids.
3. Agents selon la revendication 1, caractérisés en ce qu'ils sont constitués par des solutions aqueuses des composants a) et b) d'une concentration totale de 20-60% en poids et d'un pH de 1,5-10.
4. Agents selon la revendication 1, caractérisés en ce qu'ils contiennent comme composant a) un ester qui est fabriqué à partir d'un acide carboxylique de formule
Figure imgb0038
dans laquelle
R2 représente un groupe alkylène en Ci-C4, un groupe -CH = CH-, un groupe o-, m- ou p-phénylène, un groupe alkylène en C2 ou C3 substitué par NH2, ou une liaison directe, ou de son anhydre, et soit des composés polyhydroxylés de formules
Figure imgb0039
dans lesquelles
R1 a la signification indiquée précédemment et
R3 et R4 représentent l'hydrogène ou un groupe méthyle et d représente un nombre de 1 à 8, soit des polyalcools tels que glycérol, triméthylolpro- pane ou sorbitol.
5. Agents selon la revendication 1, caractérisés en ce qu'ils contiennent comme composant b) un composé contenant au moins un groupe amino, qui contient un groupe éther, ester, amide carboxylique et/ou uréthanne et qui a un poids moléculaire de 300-12000.
6. Agents selon la revendication 1, caractérisés en ce qu'ils contiennent comme composant b) un composé de formule
Figure imgb0040
dans laquelle
X représente un groupe alkyle en C1-C4 ou un groupe
Figure imgb0041
R3 et R4 représentent un atome d'hydrogène ou un groupe méthyle,
R5 représente un groupe alkylène en C2-C6, e est un nombre de 0 à 10 et
f est un nombre de 1 à 100, et leurs produits de réaction avec un diisocyanate.
7. Procédé pour le tannage, le prétannage, le re- tannage, la tainture ou le nourrissage de cuiret ou de cuir prétanné ou complètement tanné, caractérisé en ce que l'on opère en présence d'agents selon la revendication 1.
8. Procédé selon la revendication 7, caractérisé en ce que le traitement est mis en oeuvre dans un bain aqueux qui contient 0,5-20% en poids d'agents selon la revendication 1.
EP86109234A 1985-07-18 1986-07-07 Agent de traitement du cuir et son utilisation Expired EP0209780B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853525605 DE3525605A1 (de) 1985-07-18 1985-07-18 Lederbehandlungsmittel und ihre verwendung
DE3525605 1985-07-18

Publications (3)

Publication Number Publication Date
EP0209780A2 EP0209780A2 (fr) 1987-01-28
EP0209780A3 EP0209780A3 (en) 1987-11-11
EP0209780B1 true EP0209780B1 (fr) 1989-02-08

Family

ID=6276051

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86109234A Expired EP0209780B1 (fr) 1985-07-18 1986-07-07 Agent de traitement du cuir et son utilisation

Country Status (6)

Country Link
US (1) US5103521A (fr)
EP (1) EP0209780B1 (fr)
JP (1) JPS6220599A (fr)
CA (1) CA1285351C (fr)
DE (2) DE3525605A1 (fr)
ES (1) ES2000358A6 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3614280A1 (de) * 1986-04-26 1987-10-29 Bayer Ag Lederbehandlungsmittel
KR101849517B1 (ko) * 2010-10-28 2018-04-17 스탈 인터내셔날 비.브이. 비금속 태닝

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT482244A (fr) * 1950-12-29
DE1469014A1 (de) * 1961-10-05 1969-07-24 Diamond Shamrock Corp Neue Behandlungsmittel fuer poroese oder faserartige Stoffe,Verfahren zu ihrer Herstellung und ihrer Verwendung
US4106897A (en) * 1974-04-04 1978-08-15 Bayer Aktiengesellschaft Leather tanning with oligourethanes
CH599391A5 (fr) * 1974-09-10 1978-05-31 Sandoz Ag
DE2626430C2 (de) * 1976-06-12 1982-06-03 Bayer Ag, 5090 Leverkusen Verfahren zum Gerben von Leder und Gerbmischung
DE2739378A1 (de) * 1977-09-01 1979-03-15 Bayer Ag Wasserloesliche kationische oligourethan-harze und deren verwendung zur behandlung von bloesse oder leder

Also Published As

Publication number Publication date
US5103521A (en) 1992-04-14
EP0209780A2 (fr) 1987-01-28
DE3662058D1 (en) 1989-03-16
EP0209780A3 (en) 1987-11-11
JPS6220599A (ja) 1987-01-29
CA1285351C (fr) 1991-07-02
ES2000358A6 (es) 1988-02-16
DE3525605A1 (de) 1987-01-22

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