EP1592814B1 - Procede de production de cuir - Google Patents

Procede de production de cuir Download PDF

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Publication number
EP1592814B1
EP1592814B1 EP04706144A EP04706144A EP1592814B1 EP 1592814 B1 EP1592814 B1 EP 1592814B1 EP 04706144 A EP04706144 A EP 04706144A EP 04706144 A EP04706144 A EP 04706144A EP 1592814 B1 EP1592814 B1 EP 1592814B1
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Prior art keywords
process according
butyl
alkyl
leather
formula
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EP1592814A1 (fr
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Stephan Hüffer
Gerhard Wolf
Matthias KLÜGLEIN
Matthias Kroner
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BASF SE
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BASF SE
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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
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • C14C3/22—Chemical tanning by organic agents using polymerisation products

Definitions

  • polymers can be used in pre-treatment, main- and retanning. In many cases, the use of polymers in the pre-tanning process makes it possible to dispense entirely or at least partially with Cr compounds.
  • the choice of polymers can affect the properties of the final leather product. For the choice of polymers different proposals are made in the literature.
  • EP-A 0 628 085 describes the use of copolymers of maleic anhydride and optionally a second monomer, for example styrene, isobutene or vinyl acetate, the copolymers being reacted before use with retanning and filling with alkoxylated alcohols.
  • a second monomer for example styrene, isobutene or vinyl acetate
  • EP-A 0 372 746 is the use of amphiphilic copolymers of methacrylic acid and, for example, cetyl eicosyl methacrylate (Process Example A) or of acrylic acid with ⁇ -hexadecene (Process Example C) for the post-treatment of leather known.
  • the use of such polymers is limited to the post-treatment of chrome-tanned leathers (see page 8, lines 50-54).
  • EP-A 0 792 377 For example, a process is known in which the tanning and optionally also the pretanning is carried out by aldehydes or other reactive carbonyl compounds in the presence of polymers, for example maleic anhydride- ⁇ -olefin-styrene terpolymers (Valiante I).
  • polymers for example maleic anhydride- ⁇ -olefin-styrene terpolymers (Valiante I).
  • Valiante I maleic anhydride- ⁇ -olefin-styrene terpolymers
  • the polymers mentioned in the prior art are not yet optimal for the treatment of especially soft leathers.
  • the leathers produced by the previous methods can be improved in their fullness, their scar texture and the surface properties.
  • the distribution of the fats used in the retanning in the leather cross section is not optimal.
  • At least 0.55 equivalents (D), based on (A), are used for this purpose.
  • one may employ up to one equivalent of (D), based on (A).
  • Exemplary selected compounds of formula III are (meth) acrylamides such as acrylamide, N-methylacrylamide, N, N-dimethylacrylamide, N-ethylacrylamide, N-propylacrylamide, N-tert-butylacrylamide, N-tert-octylacrylamide, N-undecylacrylamide or the corresponding methacrylamides.
  • Exemplary selected compounds of the formula IV a are N-vinylcarboxamides such as N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide or N-vinyl-N-methylacetamide; Exemplary selected representatives of compounds of the formula IV b are N-vinylpyrrolidone, N-vinyl-4-piperidone and N-vinyl- ⁇ -caprolactam.
  • Exemplary selected compounds of formula VI are (meth) acrylic acid esters and amides such as N, N-dialkylaminoalkyl (meth) acrylates or N, N-dialkylaminoalkyl (meth) -acrylamides; Examples are N, N-dimethylaminoethyl acrylate, N, N-dimethylaminoethyl methacrylate, N, N-diethylaminoethyl acrylate, N, N-diethylaminoethyl methacrylate, N, N-dimethylaminopropyl acrylate, N, N-dimethylaminopropyl methacrylate, N, N-diethylaminopropyl acrylate, N, N-diethylaminopropyl methacrylate, 2- (N, N-Dimethylamino) ethylacrylamide, 2- (N, N-dimethylamino) ethylmethacrylamide,
  • Exemplary selected compounds of formula VII are vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate or vinyl laurate.
  • monomer (C) acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, acrylamide, vinyl n-butyl ether, vinyl isobutyl ether, N-vinylformamide, N-vinylpyrrolidone, 1-vinylimidazole and 4-vinylpyridine.
  • the molar ratio (A): (B) is in the range of 1: 0.1 to 10, preferably 1: 0.2 to 5, particularly preferably 1: 0.3 to 3.
  • the molar ratio (A) to (C) is in the range of 1: 0 to 1:10, preferably 10: 1 to 1: 5, more preferably 5: 1 to 1: 3.
  • the molar ratio (A) to [(B) + (C)] is in the range from 2: 1 to 1:20, preferably 1: 1 to 1:10, particularly preferably 1: 1 to 1: 6th
  • the polymers used in the preparation of the processes according to the invention can be carried out by methods known per se.
  • (A), (B) and optionally (C) can copolymerize in the form of random copolymers, as alternating copolymers or as block copolymers.
  • Pressure and temperature conditions for copolymerization of (A), (B) and optionally (C) are generally not critical.
  • the temperatures are for example in the range of 40 to 200 ° C, preferably 60 to 150 ° C, the pressure is for example in the range of 1 to 10 bar, preferably 1 to 3 bar.
  • Suitable solvents are those solvents which are considered inert to anhydrides of dicarboxylic acid having 4 to 8 carbon atoms, in particular acetone, tetrahydrofuran or 1,4-dioxane.
  • Suitable precipitants are aromatic and aliphatic hydrocarbons, for example toluene, ortho-xylene, meta-xylene, para-xylene, ethylbenzene or mixtures of one or more of the abovementioned aromatic hydrocarbons, n-hexane, petroleum ether or isododecane. Also mixtures of aromatic and aliphatic hydrocarbons are suitable.
  • regulators for example mercaptoethanol or n-dodecylmercaptan. Suitable amounts are, for example, 0.1 to 6 wt .-%, based on the mass of all monomers.
  • the copolymerization is advantageously started by initiators, for example peroxides or hydroperoxides.
  • Suitable peroxides or hydroperoxides are di-tert-butyl peroxide, tert-butyl peroctoate, tert-butyl perpivalate, tert-butyl per-2-ethylhexanoate, tert-butyl permalate, tert-butyl perisobutyrate, benzoyl peroxide, diacetyl peroxide, succinyl peroxide, p-butyl peroxide. Chlorobenzoyl peroxide, Dicyclohexylperoxiddicarbonat, exemplified.
  • redox initiators is also suitable, as well as azo compounds such as 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2-methylpropionamidine) dihydrochloride and 2,2'-azobis (4-methoxy-2,4 dimethylvaleronitrile).
  • these initiators are used in amounts of 0.1 to 20 wt .-%, preferably 0.2 to 15 wt .-%, calculated on the mass of all monomers.
  • copolymerization described above gives copolymers.
  • the resulting copolymers can be subjected to purification by conventional methods, for example reprecipitation or extractive removal of unreacted monomers. If a solvent or precipitant has been used, it is possible to remove it after completion of the copolymerization, for example by distillation.
  • the resulting copolymers are not subjected to additional purification and immediately reacted with (D).
  • the copolymerization is carried out in the presence of the entire amount or proportion of the compound (D) to be employed.
  • the copolymerization is carried out in the presence of the entire amount or proportion of the compound (D) to be employed.
  • reaction of the copolymers described above with (D) is carried out, for example, at temperatures of 90 to 150 ° C.
  • the reaction of the copolymers described above with (D) is carried out, for example, at pressures of 1 to 10 bar, preferably 1 to 3 bar.
  • the amount of (D) is calculated as starting from a complete reaction of (D) and 5 to 80 mol%, preferably 10 to 67 mol%, particularly preferably 20 to 50 mol% (D), based on all carboxyl groups of the copolymer used.
  • the duration of the reaction of the above-described copolymers with (D) is generally 0.1 to 8 hours, preferably 1 to 5 hours.
  • the reaction of the above-described copolymers with (D) can be carried out in the absence or presence of catalysts, in particular acidic catalysts, e.g. Sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, n-dodecylbenzenesulfonic acid, hydrochloric acid or acidic ion exchangers.
  • catalysts in particular acidic catalysts, e.g. Sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, n-dodecylbenzenesulfonic acid, hydrochloric acid or acidic ion exchangers.
  • reaction of the above-described copolymers with (D) is carried out in the presence of an entraining agent which forms an azeotrope with water which may be formed in the reaction.
  • the polymers are reacted with water or with an aqueous alkaline solution and obtain partially or completely hydrolyzed polymers, which are also referred to below as hydrolyzed polymers.
  • the hydrolysis is carried out by reacting the polymers according to the invention with water or aqueous alkaline solution, such as alkali metal hydroxides, e.g. Sodium hydroxide or potassium hydroxide, of ammonia, primary, secondary or tertiary alkylamines or alkanolamines.
  • alkali metal hydroxides e.g. Sodium hydroxide or potassium hydroxide
  • sodium hydroxide solution or potassium hydroxide solution are suitable.
  • about 20 to 50% by weight of water or aqueous alkaline solution, based on the copolymer, is used.
  • the temperature during the hydrolysis is generally not critical. In general, suitable are from 20 to 100.degree. C., preferably up to 90.degree. Usually, the hydrolysis is completed after 10 minutes to 4 hours.
  • Hydrolyzed polymers are obtained in which the anhydride groups unreacted in the reaction with (D) are completely or partially hydrolyzed and the carboxylic acid groups are present free or in the form of their alkali metal salts or ammonium salts.
  • the polydispersity of the hydrolyzed polymers described above is generally between 2 and 10, preferably up to 7.
  • the K values of the hydrolyzed polymers described above are from 6 to 100, preferably from 10 to 60 (measured according to H. Fikentscher at 25 ° C. in water and a polymer concentration of 1% by weight).
  • the polymers or hydrolyzed polymers described above can be used according to the invention in the pretanning or tanning.
  • the polymers or hydrolyzed polymers described above can be used according to the invention in the retanning.
  • the process according to the invention for the production of leather can be carried out as a process for pretanning or tanning, in the following also called tanning process according to the invention.
  • the tanning process according to the invention is based on hides pretreated by conventional methods from animals such as, for example, cattle, pigs, goats or deer, the so-called pelts. It is for that Tanning method according to the invention is not essential, whether the animals were killed, for example, by slaughtering or died of natural causes.
  • Conventional methods of pre-treatment include, for example, liming, deliming, pickling and pimpling, as well as mechanical operations such as skinning the hides.
  • the tanning process according to the invention is generally carried out by adding one or more tanning agents according to the invention in one portion or in several portions immediately before or else during the tanning step.
  • the tanning process according to the invention is preferably carried out at a pH of 2.5 to 4, it being frequently observed that the pH increases by about 0.3 to three units during the performance of the tanning process according to the invention. It is also possible to increase the pH by about 0.3 to three units by adding blunting agents.
  • the tanning process according to the invention is generally carried out at temperatures of 10 to 45 °, preferably at 20 to 30 ° C. Has proven useful a duration of 10 minutes to 12 hours, preferably one to three hours.
  • the tanning process according to the invention can be carried out in any conventional tanning vessel, for example by walking in barrels or in rotated drums.
  • the above-described polymers or hydrolyzed polymers are used together with one or more conventional tanning agents, for example with chrome tanning agents, mineral tannins, syntans, polymer tanning agents or vegetable tanning agents, as described, for example Ullmann's Encyclopedia of Industrial Chemistry, Volume A15, pages 259 to 282 and especially page 268 ff., 5th Edition, (1990), Verlag Chemie Weinheim.
  • the weight ratio of the polymers or hydrolyzed polymer described above: conventional tanning agent or sum of conventional tanning agents is advantageously from 0.01: 1 to 100: 1.
  • the above-described polymers or hydrolyzed polymers are added in one portion or in several portions before or during pre-tanning, in a particular variant already in pimples.
  • the process according to the invention for the production of leather can also be carried out as a process for retanning leather using the above-described polymers or hydrolyzed polymers, in the following also called retanning processes according to the invention.
  • the retanning process according to the invention is based on conventional, i. for example, with chrome tanning agents, mineral tannins, polymer tanning agents, aldehydes, syntans or resin tanning tanned semi-finished products or semi-finished products according to the invention as described above.
  • chrome tanning agents i. for example, with chrome tanning agents, mineral tannins, polymer tanning agents, aldehydes, syntans or resin tanning tanned semi-finished products or semi-finished products according to the invention as described above.
  • the above-described polymers or hydrolyzed polymers are allowed to act on semi-finished products.
  • the retanning process according to the invention can be carried out under otherwise customary conditions. It is convenient to choose one or more, i. 2 to 6 action steps and can rinse with water between the interaction steps.
  • the temperature in the individual reaction steps is in each case from 5 to 60.degree. C., preferably from 20 to 45.degree.
  • further agents customarily used during the retanning for example fatliquors, polymer tanning agents and acrylate- and / or methacrylate-based fatliquoring agents, retanning agents based on resin and vegetable tanning agents, fillers, leather dyes or emulsifiers.
  • aqueous dispersions and solutions containing the hydrolyzed polymers described above are aqueous dispersions and solutions containing the hydrolyzed polymers described above.
  • dispersions are to be understood as meaning, for example, emulsions or suspensions of the above-described polymers.
  • the aqueous dispersions according to the invention and the aqueous solutions according to the invention usually contain from 20 to 50% by weight of the polymers according to the invention. Its pH is usually 2 to 10 and is preferably in the range of 2 to 7.
  • the dispersions according to the invention contain unreacted Ia or Ib.
  • a further aspect of the present invention is leather produced by the tanning process according to the invention or the retanning process according to the invention or by a combination of inventive tanning process and retanning process according to the invention.
  • the leathers of the invention are characterized by an overall advantageous quality, for example, they feel particularly soft.
  • the leathers of the invention contain the polymers described above or the hydrolyzed polymers described above are distributed evenly over the cross section.
  • Another aspect of the present invention is the use of the leather according to the invention for the production of clothing, furniture or car parts.
  • garments are, for example, jackets, trousers, shoes, belts or suspenders.
  • furniture is to be understood as meaning all furniture which contains leather components. Examples include seating, such as armchairs, chairs, sofas.
  • Car parts are exemplified by car seats.
  • Another aspect of the present invention are garments comprising or made of leathers of the invention.
  • Another aspect of the present invention is furniture comprising or made of leathers according to the invention.
  • Another aspect of the present invention are car parts containing or made from leathers of the invention. The invention will be explained by working examples.
  • the K value of the white powder precursor VP10 was 15.9 (1 wt% in cyclohexanone at 25 ° C).
  • the preparation of the polymers P10 to 14 from the precursors VP 10 or VP 13 and the alkylpolyalkylene glycols indicated in Table 2 was carried out by heating a mixture of the two components under nitrogen. The reaction took place within 4 hours at a temperature of 170.degree. After cooling to 50 ° C, the oil was dispersed with 50 g of water and 10 g of aqueous 25 wt .-% sodium hydroxide solution. The molar ratio NaOH / (sum of maleic anhydride and acrylic acid) was 0.6 / 1.0, so that 30 to 40 wt .-% dispersions having a pH of 6 to 7 resulted.
  • Zebu Wetblue leather commercially available from Packer, USA, was folded to a thickness of 1.8-2.0 mm and cut into strips of 600 g each. Subsequently, the strips were commercially available in a barrel and a liquor length of 200% by weight at intervals of 10 minutes with 2% by weight of sodium formate, 0.4% by weight of NaHCO 3 and 1% by weight of Tamol®NA at BASF Aktiengessllschaft, offset. After 90 minutes, the fleet was drained. The strips were then distributed to separate walk barrels.
  • polymer P1 4 wt .-% polymer P1 were metered, followed by 4% by weight of sulfone tanning agent Basyntan® DLX, commercially available from BASF Aktiengesellschaft, and 2% by weight of resin tanning agent Relugan® DLF, commercially available from BASF Aktiengesellschaft.
  • the leathers were then tumbled for 45 minutes at 15 revolutions per minute in the barrel.
  • 3% by weight of vegetable tanning material Mimosa® commercially available from BASF Aktiengesellschaft, was added and drumming for a further 30 minutes.
  • another 2% by weight of Luganil® Brown was added and tumbling for a further 30 minutes.
  • the leather thus obtained was washed with water, dried and staked and evaluated according to the test criteria set out in Table 3.
  • the tensile strength was determined according to DIN 53328.
  • the evaluation of the liquor was done visually according to the criteria residual dye (extinction) and turbidity (fatliquoring agent).
  • the evaluation of further performance characteristics was carried out by subjects according to a grading system from 1 (very good) to 5 (deficient).
  • Table 3 Performance properties of the invention leather 2.1 to 2.9 and comparative samples V 2.17 to V 2.19 No.
  • Polymer V17 Polyacrylic acid with a K value of 60, determined according to Fikentscher, partially neutralized with NaOH to a pH of 5.
  • Polymer V18 polymer EP-B 0 628 085
  • Polymer V19 polymer EP-B 0 628 085 Example 20.
  • the pelt of a southern German bovine was converted into a corresponding wetwhite semi-finished product with 2.5% by weight of glutardialdehyde and 3% by weight of the sulfone tanning agent Basyntan®, commercially available from BASF Aktiengesellschaft, in each case based on the pelt weight.
  • the pH was 3.9).
  • the pre-tanned pelt was wilted, folded to a thickness of 1.2 mm and cut into strips of 400 g each.
  • Strips containing 100% by weight of water, 6% by weight of the sulfone tanning agent were placed in a barrel Basyntan® DLX-N, 5% by weight of the vegetable tanning agent Tara®, 3% by weight of the resin tanning agent Relugan® S and 1.5% by weight of the dye Luganil brown NGB®, each commercially available from BASF Aktiengesellschaft, over a period of time of 60 minutes at 25 ° C-30 ° C in the barrel at 10 revolutions per minute. Then a pH of 3.6 is adjusted with formic acid and drained after a further 20 minutes, the liquor and discarded.
  • the leather thus obtained was washed with water, dried and staked and evaluated according to the test criteria set out in Table 3.
  • the tensile strength was determined according to DIN 53328.
  • the evaluation of the liquor was done visually according to the criteria residual dye (extinction) and turbidity (fatliquoring agent).
  • the evaluation of further performance characteristics was carried out by subjects according to a grading system from 1 (very good) to 5 (deficient).
  • Table 4 Application properties of the furniture leather 3.8 to 3.14 invention and the comparative samples V 3.17 to V 3.19 No.
  • Polymer V17 Polyacrylic acid with a K value of 60, determined according to Fikentscher, partially neutralized with NaOH to a pH of 5.
  • Polymer V18 polymer EP-B 0 628 085
  • Polymer V19 polymer EP-B 0 628 085 Example 20.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Claims (13)

  1. Procédé de fabrication de cuir, caractérisé en ce que des peaux, des peaux picklées ou des semi-finis sont traités avec au moins un polymère
    qui peut être obtenu
    par copolymérisation
    d'au moins un anhydride d'acide dicarboxylique éthyléniquement insaturé (A), dérivé d'au moins un acide dicarboxylique contenant 4 à 8 atomes C,
    d'au moins un composé vinylaromatique (B) et éventuellement d'au moins un monomère éthyléniquement insaturé (C) différent de (A) contenant au moins un hétéroatome, mis en réaction avec au moins un composé (D) de formule générale Ia ou Ib
    Figure imgb0024
     au moins 0,55 équivalent de (D) étant utilisé par rapport à (A),
    et hydrolyse éventuelle avec de l'eau ou une solution alcaline aqueuse,
    les variables des formules Ia et Ib étant définies de la manière suivants :
    A1 identiques ou différents et alkylène en C2-C6
    R1 alkyle en C1-C20, linéaire ou ramifié,
    n un nombre entier de 6 à 200.
  2. Procédé selon la revendication 1, caractérisé en ce que le polymère est traité avant utilisation avec de l'eau ou une solution alcaline aqueuse.
  3. Procédé selon la revendication 1 ou 2, caractérisé en ce que (B) est le styrène.
  4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé en ce que le rapport molaire de (A) sur (C) se situe dans la plage allant de 1:0 à 1:10.
  5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que le rapport molaire de (A) sur [(B)+(C)] se situe dans la plage allant de 2:1 à 1:20.
  6. Procédé selon l'une quelconque des revendications 1 à 5, caractérisé en ce que (C) est choisi parmi les dérivés d'acides carboxyliques en C3-C8 éthyléniquement insaturés de formule générale II
    Figure imgb0025
     les acrylamides de formule III
    Figure imgb0026
     les amides non cycliques de formule générale Iva ou les amides cycliques de formule générale IVb
    Figure imgb0027
     les éthers vinyliques d'alkyle en C1-C20, les dérivés de N-vinyle de composés aromatiques contenant de l'azote, les nitriles α,β-insaturés, les éthers alcoxylés insaturés de formule générale V
    Figure imgb0028
     les esters ou les amides de formule générale VI
    Figure imgb0029
     les esters insaturés de formule générale VII
    Figure imgb0030
     les variables des formules générales étant définies de la manière suivants :
    R2, R3 identiques ou différents et choisis parmi l'hydrogène, un alkyle en C1-C10 ramifié ou non ramifié,
    R4 identiques ou différents et choisis parmi l'hydrogène ou un alkyle en C1-C22, ramifié ou non ramifié,
    R5 l'hydrogène ou un méthyle,
    x un nombre entier dans la plage allant de 2 à 6,
    y un nombre entier choisi parmi 0 ou 1,
    a un nombre entier dans la plage allant de 0 à 6, R6, R7 identiques ou différents et choisis parmi l'hydrogène, un alkyle en C1-C10 ramifié ou non ramifié,
    X l'oxygène ou N-R4,
    R8 [A1-O]n-R4,
    R9 identiques ou différents et choisis parmi l'hydrogène, un alkyle en C1-C10 ramifié ou non ramifié,
    les autres variables étant définies tel que précédemment.
  7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé en ce que l'hydrolyse est réalisée à des températures de 15 à 100 °C.
  8. Procédé selon l'une quelconque des revendications 1 à 7, caractérisé en ce que les polymères sont introduits sous la forme d'une dispersion ou solution aqueuse.
  9. Cuir, fabriqué par un procédé selon l'une quelconque des revendications 1 à 8.
  10. Utilisation de cuirs selon la revendication 9 pour la fabrication de vêtements, de meubles ou de parties d'automobiles.
  11. Vêtements, fabriqués à partir de ou contenant un cuir selon la revendication 9.
  12. Meubles, fabriqués à partir de ou contenant un cuir selon la revendication 9.
  13. Parties d'automobiles, fabriquées à partir de ou contenant un cuir selon la revendication 9.
EP04706144A 2003-02-06 2004-01-29 Procede de production de cuir Expired - Lifetime EP1592814B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10304959A DE10304959A1 (de) 2003-02-06 2003-02-06 Verfahren zur Herstellung von Leder
DE10304959 2003-02-06
PCT/EP2004/000777 WO2004070063A1 (fr) 2003-02-06 2004-01-29 Procede de production de cuir

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EP1592814A1 EP1592814A1 (fr) 2005-11-09
EP1592814B1 true EP1592814B1 (fr) 2010-10-13

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EP (1) EP1592814B1 (fr)
KR (1) KR20050097973A (fr)
CN (1) CN100523224C (fr)
AR (1) AR043361A1 (fr)
AT (1) ATE484599T1 (fr)
BR (1) BRPI0406758A (fr)
DE (2) DE10304959A1 (fr)
WO (1) WO2004070063A1 (fr)

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DE202006011724U1 (de) * 2006-07-31 2007-12-06 Schaefer, Philipp Fahrzeugsitz
CN101802071B (zh) 2007-09-03 2013-01-16 巴斯夫欧洲公司 含水配制料的制备方法、含水配制料及其用途
BRPI0816186A2 (pt) * 2007-09-03 2015-04-14 Basf Se Processo para a preparação der formulações aquosas, formulações aquosas, uso de formulações aquosas, processo para a produção de couro, couro, copolímero,e, misturas
JP5466678B2 (ja) * 2011-08-31 2014-04-09 下越生コン建設株式会社 選別バケット
EP2607499A3 (fr) * 2013-02-14 2013-07-10 Basf Se Procédé destiné à la fabrication de cuir
CN116376036A (zh) * 2023-04-20 2023-07-04 东南大学 一种梳型聚羧酸盐分散剂及其制备方法和应用

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GB2068999B (en) * 1980-02-11 1984-02-22 British Leather Mfg Res Tanning leather
DE4205839A1 (de) * 1992-02-26 1993-09-02 Basf Ag Verwendung von umsetzungsprodukten von homo- oder copolymerisaten auf basis monoethylenisch ungesaettigter dicarbonsaeureanhydride mit aminen oder alkoholen zum fetten und fuellen von leder oder pelzfellen
DE4334796A1 (de) * 1993-10-13 1995-04-20 Bayer Ag Weichmachende und hydrophobierende Nachgerbstoffe
DE19610553A1 (de) * 1996-03-18 1997-09-25 Henkel Kgaa Verfahren zur Herstellung von Leder

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CN1748038A (zh) 2006-03-15
DE10304959A1 (de) 2004-08-19
US20060130241A1 (en) 2006-06-22
AR043361A1 (es) 2005-07-27
EP1592814A1 (fr) 2005-11-09
KR20050097973A (ko) 2005-10-10
DE502004011774D1 (de) 2010-11-25
CN100523224C (zh) 2009-08-05
BRPI0406758A (pt) 2005-12-20
ATE484599T1 (de) 2010-10-15

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