EP0024014A1 - Procédé de retannage de cuirs tannés au minéral avec des acides sulfoniques aromatiques - Google Patents
Procédé de retannage de cuirs tannés au minéral avec des acides sulfoniques aromatiques Download PDFInfo
- Publication number
- EP0024014A1 EP0024014A1 EP80104522A EP80104522A EP0024014A1 EP 0024014 A1 EP0024014 A1 EP 0024014A1 EP 80104522 A EP80104522 A EP 80104522A EP 80104522 A EP80104522 A EP 80104522A EP 0024014 A1 EP0024014 A1 EP 0024014A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- leather
- terphenyl
- retanning
- alkali
- agents
- 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.)
- Granted
Links
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
- D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/622—Sulfonic acids or their salts
- D06P1/625—Aromatic
-
- 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
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/28—Multi-step processes
-
- 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
- the isomeric mono- and disulfonic acids of diphenyl, terphenyl, diphenyl ether and ditolyl ether and their alkali and ammonium salts are preferably used.
- sulfonic acids of other non-crosslinked aromatic hydrocarbons in various leather manufacturing processes for example naphthalene and toluene, as auxiliaries for decalcifying raw material (GB-PS 8096) or in the form of their chromium III salts for tanning (DE-PS 627 110 and 643 088) is already known.
- the alkali metal salts of the mono- and disulfonic acids of benzene and naphthalene have also already been proposed for the preservation and improvement of the storage stability of mineral-soft, undyed leather in a moist or dry state (DE-PS 578 785).
- aromatic sulfonic acids as non-swelling acids to acidify the skin material prior to tanning is state of the art (see Ullmanns Enzyklopadie der Technische Chemie, 4th edition; volume 16, page 120).
- Commonly used as retanning agents and as auxiliaries for leveling chemical and / or physical irregularities in the leather surface are, for example, formaldehyde condensation products of ⁇ -naphthalenesulfonic acid (DE-PS 290 965), the diphenyl and ditolyl ether sulfonic acids (US Pat. No. 2,315,951) and terphenyl sulfonic acids (US Pat. No. 3,906,037) and their ammonium or alkali salts.
- So-called exchange tanning agents which are predominantly present as phenol-containing formaldehyde condensation products of aromatic sulfonic acids or their salts, are customary as retanning and / or leveling agents for chrome leather (GB-PS 1 291 784 and DT-PS 611 671).
- tanning agents and leveling agents There are gradual differences in the brightening effect on colorations between the different types of tanning agents and leveling agents, which may depend, among other things, on the ratio of leveling agents or retanning agents to dye and dye-specific, but they consistently cause high color loss on leather, which can reach 50 - 80% compared to leather that can be dyed under comparable conditions but without retanning or leveling agent treatment.
- the sulfonic acids or their salts of the formula (I), which have not been condensed to form larger molecules with formaldehyde like anionic synthetic tanning agents and leveling agents, are particularly suitable as retanning agents. They offer the advantage that the leather retanned with it or the leather treated before or during dyeing results in deep and brilliant surface dyeings with anionic dyes with excellent levelness. The color depth results similar to that of pure chrome leather, which does not come with after tannins and / or leveling agents have been treated.
- Suitable retanning agents of the formula (I), which allow a deep and brilliant coloration of the leather with optimal use of the dye range, are preferably suitable partially or completely with sodium hydroxide or - because of their better solubility - preferably mixtures of terphenyl-mono- and- neutralized with ammonia disulfonic acids. They can e.g. produce by allowing 2 mols of sulfuric acid monohydrate to act for 2 hours at 145-150 ° C. for 2 hours for sulfonation in accordance with US Pat. No. 3,906,037, Example 3, lines 44-54, for 1 mol of a technical terphenyl isomer mixture and then reacting the reaction mixture neutralizes the desired final pH and converts it into powder by spray drying.
- the technical isomer mixtures of terphenyl which are inevitably obtained as by-products in the diphenyl synthesis from benzene, are suitable and particularly economical as the starting product for the production of such terphenylsulfonic acid mixtures.
- the sulfonic acids and their salts of the formula (I) are optimally effective for levelness, brilliance and depth of the coloration of the leather, if they are mixed with anionic dyes in amounts of before or during the coloration 2 - 10%, preferably 3 - 6% (based on the so-called fold weight of the leather) act on the leather and let it open. They are particularly good at leveling the color and compensating for the different dyeability of damaged and undamaged areas within individual skins or skins if they are applied to the leather before the dye is added and the dye can then be evenly applied to the leveled leather.
- Chromium leather from cowhide or calfskin which is manufactured in the usual way, folded to 1.6 - 1.8 mm and neutralized to pH 3.8 - 4.2, is treated with 100% liquor in a rotating tanning drum with 6% of an acid number (mg KOH / g) 40 adjusted mixture of terphenyl mono- and di-sulfonic acid ammonium salts, which is formed when 2.4 mol of sulfuric acid monohydrate is allowed to act on a technical mixture of terphenyl isomers from the diphenyl synthesis at 150 ° C. in the course of 3 hours and then after cooling and diluting to acid number 40 neutralized with ammonia and spray dried.
- an acid number (mg KOH / g) 40 adjusted mixture of terphenyl mono- and di-sulfonic acid ammonium salts which is formed when 2.4 mol of sulfuric acid monohydrate is allowed to act on a technical mixture of terphenyl isomers from the diphenyl synthesis at 150
- dyeing is carried out in the customary manner with 1% of the copper complex of a monoazo dye from DE-PS 670 935, example 1.
- greasing is carried out in the dye bath in the customary manner and then treated with 1.5% formic acid in order to achieve the best possible absorption of the dye and the greasing.
- this leather corresponds to a leather dyed without auxiliary treatment with the same amount of dye, but which results in significantly lower levelness.
- a diphenyl ether disulfonic acid sodium salt for 10 minutes to initiate retanning in a 100% warm liquor.
- 2.4 mol of sulfuric acid monohydrate on 1 mol of diphenyl ether are advantageously allowed to act at 120 ° C. for 2 hours with vigorous stirring, the mixture is cooled, diluted, neutralized with sodium hydroxide solution and converted into powder form by spray drying.
- chrome leather which is folded and neutralized to pH 6.0 (cut color with bromotymol blue, yellow to yellow-green), is first washed with 300% water at 40 ° C in a customary manner. After draining the wash liquor, pre-greased with 2.5% of a sulfited leather-based grease agent based on trans in 100% of a liquor at 40 ° C. for 15 minutes and then in the same liquor for 10 minutes with 1% of an ammonia solution is that contains 2.5 percent by weight of NH 3 .
- o-Terphenyl-4,4 ', 4 "-trisulfonic acid is prepared by reacting 230 g each of o-terphenyl (approx. 95%) with 1500 g of sulfuric acid monohydrate at 110 ° C. for 90 minutes and with potassium chloride in the potassium salt transferred (see Journal of Organic Chemistry 14, 163 (1949)).
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2932688 | 1979-08-11 | ||
DE19792932688 DE2932688A1 (de) | 1979-08-11 | 1979-08-11 | Verfahren zum nachgerben mineralisch gegerbter leder mit aromatischen sulfonsaeuren |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0024014A1 true EP0024014A1 (fr) | 1981-02-18 |
EP0024014B1 EP0024014B1 (fr) | 1982-05-19 |
Family
ID=6078301
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104522A Expired EP0024014B1 (fr) | 1979-08-11 | 1980-07-31 | Procédé de retannage de cuirs tannés au minéral avec des acides sulfoniques aromatiques |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0024014B1 (fr) |
JP (1) | JPS5628300A (fr) |
AR (1) | AR220483A1 (fr) |
BR (1) | BR8005016A (fr) |
DE (2) | DE2932688A1 (fr) |
ES (1) | ES494117A0 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347373A1 (fr) * | 1988-06-06 | 1989-12-20 | Ciba-Geigy Ag | Solutions aqueuses de tannins synthétiques |
FR2658211A1 (fr) * | 1990-02-10 | 1991-08-16 | Sandoz Sa | Utilisation de composes aromatiques contenant des groupes sulfo, comme auxiliaires d'application dans la traitement des matieres fibreuses. |
EP0470465A1 (fr) * | 1990-08-10 | 1992-02-12 | Bayer Ag | Procédé de retannage de cuir qui au préalable a subi un tannage minéral par des acides sulfoniques aromatiques |
US6922431B1 (en) | 1997-07-31 | 2005-07-26 | Telefonaktiebolaget Lm Ericsson (Publ) | Communication using spread spectrum methods over optical fibers |
WO2010130311A1 (fr) * | 2009-05-14 | 2010-11-18 | Clariant International Ltd | Procédé et composition de tannage |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5172228B2 (ja) | 2007-06-28 | 2013-03-27 | ミドリホクヨー株式会社 | 革 |
WO2009139194A1 (fr) | 2008-05-16 | 2009-11-19 | ミドリホクヨー株式会社 | Couche de finition |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR505388A (fr) * | 1913-12-08 | 1920-07-29 | Basf Ag | Procédé de tannage, nouveaux produits tannants et leurs applications |
US1945461A (en) * | 1930-12-10 | 1934-01-30 | Rohm & Haas | Method of retanning of chrome leather |
US2292067A (en) * | 1941-04-25 | 1942-08-04 | Du Pont | Production of white leather |
FR959065A (fr) * | 1950-03-23 | |||
US2973240A (en) * | 1951-06-21 | 1961-02-28 | Boehme Fettchemie Gmbh | Tanning with alkylbenzene sulfonate in combination with chrome tanning |
FR1282449A (fr) * | 1961-03-01 | 1962-01-19 | Stockhausen & Cie Chem Fab | Procédé d'égalisage des teintures sur cuirs ayant subi un tannage au chrome ou un tannage combiné |
DE2048171A1 (de) * | 1969-09-30 | 1971-04-01 | Imperial Chemical Industries Ltd , London | Farbeverfahren |
GB2006276A (en) * | 1977-09-24 | 1979-05-02 | Bayer Ag | Dyestuff formulations |
-
1979
- 1979-08-11 DE DE19792932688 patent/DE2932688A1/de not_active Withdrawn
-
1980
- 1980-07-31 DE DE8080104522T patent/DE3060449D1/de not_active Expired
- 1980-07-31 EP EP80104522A patent/EP0024014B1/fr not_active Expired
- 1980-08-07 JP JP10779880A patent/JPS5628300A/ja active Granted
- 1980-08-08 ES ES494117A patent/ES494117A0/es active Granted
- 1980-08-08 BR BR8005016A patent/BR8005016A/pt unknown
- 1980-08-11 AR AR282118A patent/AR220483A1/es active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR959065A (fr) * | 1950-03-23 | |||
FR505388A (fr) * | 1913-12-08 | 1920-07-29 | Basf Ag | Procédé de tannage, nouveaux produits tannants et leurs applications |
US1945461A (en) * | 1930-12-10 | 1934-01-30 | Rohm & Haas | Method of retanning of chrome leather |
US2292067A (en) * | 1941-04-25 | 1942-08-04 | Du Pont | Production of white leather |
US2973240A (en) * | 1951-06-21 | 1961-02-28 | Boehme Fettchemie Gmbh | Tanning with alkylbenzene sulfonate in combination with chrome tanning |
FR1282449A (fr) * | 1961-03-01 | 1962-01-19 | Stockhausen & Cie Chem Fab | Procédé d'égalisage des teintures sur cuirs ayant subi un tannage au chrome ou un tannage combiné |
DE2048171A1 (de) * | 1969-09-30 | 1971-04-01 | Imperial Chemical Industries Ltd , London | Farbeverfahren |
GB2006276A (en) * | 1977-09-24 | 1979-05-02 | Bayer Ag | Dyestuff formulations |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347373A1 (fr) * | 1988-06-06 | 1989-12-20 | Ciba-Geigy Ag | Solutions aqueuses de tannins synthétiques |
FR2658211A1 (fr) * | 1990-02-10 | 1991-08-16 | Sandoz Sa | Utilisation de composes aromatiques contenant des groupes sulfo, comme auxiliaires d'application dans la traitement des matieres fibreuses. |
BE1005672A3 (fr) * | 1990-02-10 | 1993-12-14 | Sandoz Sa | Utilisation de composes aromatiques contenant des groupes sulfo, comme auxiliares d'application dans le traitement des matieres fibreuses. |
EP0470465A1 (fr) * | 1990-08-10 | 1992-02-12 | Bayer Ag | Procédé de retannage de cuir qui au préalable a subi un tannage minéral par des acides sulfoniques aromatiques |
US5352241A (en) * | 1990-08-10 | 1994-10-04 | Bayer Aktiengesellschaft | Process for retanning mineral tanned leathers with aromatic sulphonic acids |
US6922431B1 (en) | 1997-07-31 | 2005-07-26 | Telefonaktiebolaget Lm Ericsson (Publ) | Communication using spread spectrum methods over optical fibers |
WO2010130311A1 (fr) * | 2009-05-14 | 2010-11-18 | Clariant International Ltd | Procédé et composition de tannage |
CN102282269A (zh) * | 2009-05-14 | 2011-12-14 | 科莱恩金融(Bvi)有限公司 | 鞣制方法和鞣制组合物 |
US8679195B2 (en) | 2009-05-14 | 2014-03-25 | Clariant Finance (Bvi) Limited | Tanning process and tanning composition |
CN102282269B (zh) * | 2009-05-14 | 2014-10-29 | 克拉里安特国际有限公司 | 鞣制方法和鞣制组合物 |
Also Published As
Publication number | Publication date |
---|---|
ES8104420A1 (es) | 1981-03-16 |
EP0024014B1 (fr) | 1982-05-19 |
ES494117A0 (es) | 1981-03-16 |
BR8005016A (pt) | 1981-02-24 |
AR220483A1 (es) | 1980-10-31 |
JPS5628300A (en) | 1981-03-19 |
DE2932688A1 (de) | 1981-02-26 |
DE3060449D1 (en) | 1982-07-08 |
JPS6318640B2 (fr) | 1988-04-19 |
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