EP0024014B1 - Verfahren zum Nachgerben mineralisch gegerbter Leder mit aromatischen Sulfonsäuren - Google Patents
Verfahren zum Nachgerben mineralisch gegerbter Leder mit aromatischen Sulfonsäuren Download PDFInfo
- Publication number
- EP0024014B1 EP0024014B1 EP80104522A EP80104522A EP0024014B1 EP 0024014 B1 EP0024014 B1 EP 0024014B1 EP 80104522 A EP80104522 A EP 80104522A EP 80104522 A EP80104522 A EP 80104522A EP 0024014 B1 EP0024014 B1 EP 0024014B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- leather
- terphenyl
- agents
- alkali
- retanning
- 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
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000010985 leather Substances 0.000 title description 37
- -1 aromatic sulfonic acids Chemical class 0.000 title description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 title description 3
- 239000011707 mineral Substances 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000006267 biphenyl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- FDLFMPKQBNPIER-UHFFFAOYSA-N 1-methyl-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(C)C=CC=2)=C1 FDLFMPKQBNPIER-UHFFFAOYSA-N 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 11
- 125000000129 anionic group Chemical group 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- AQWAQMZZGDSQNM-UHFFFAOYSA-N 3,4-bis(4-sulfophenyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1C1=CC=C(S(O)(=O)=O)C=C1 AQWAQMZZGDSQNM-UHFFFAOYSA-N 0.000 description 2
- 241001070941 Castanea Species 0.000 description 2
- 235000014036 Castanea Nutrition 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000434 metal complex dye Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000001887 acacia decurrens willd. var. dealbata absolute Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- DSHWASKZZBZKOE-UHFFFAOYSA-K chromium(3+);hydroxide;sulfate Chemical compound [OH-].[Cr+3].[O-]S([O-])(=O)=O DSHWASKZZBZKOE-UHFFFAOYSA-K 0.000 description 1
- 229910000356 chromium(III) sulfate Inorganic materials 0.000 description 1
- 239000011696 chromium(III) sulphate Substances 0.000 description 1
- 235000015217 chromium(III) sulphate Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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 an aid for the decalcification of pelt material (GB-A 8096) or in the form of their chromium III salts for tanning (DE-C 627 110 and 643088) 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-C 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).
- Formaldehyde condensation products of ⁇ -naphthalenesulfonic acid (DE-C 290 965), diphenyl and ditolyl ether sulfonic acids (US-A 2315951) and terphenylsulfonic acids (US) are, for example, common as retanning agents and as auxiliaries for leveling chemical and / or physical irregularities in the leather surface -A 3906037) 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 common practice as retanning and / or leveling agents for chrome leather (GB-A 1 291 784 and DT-A 611 671).
- 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 evenness of levelness. The color depth results similar to pure chrome leather that has not been treated with retanning agents and / or leveling agents.
- Suitable retanning agents of the formula (I), which allow a deep and brilliant coloration of the leather with optimal use of the dye, are preferably 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 moles of sulfuric acid monohydrate to act for 2 hours at 145-150 ° C. for 2 hours for sulfonation in accordance with US Pat Final pH neutralized and converted 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 formal (I) are optimally effective for levelness, brilliance and depth of the coloring of the leather if they are obtained before or during the coloring with anionic dyes in amounts of 2-10%, preferably 3-6% ( can act on the so-called fold weight of the leather) on the leather and pull it up. 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 made from cowhide or calfskin which is manufactured in the usual manner, folded to 1.6-1.8 mm and neutralized to pH 3.8-4.2, is 40 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 terphenyl isomer mixture 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 terphenyl isomer mixture from the diphenyl synthesis at 150 ° C. in the course of 3
- greasing is carried out in the dye bath in a 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 leather dyed with the same amount of dye without pretreatment, but this results in significantly lower levelness.
- a chrome leather which was treated under the same conditions with the Na salt of the terphenylsulfonic acid-formaldehyde condensate, which was prepared according to US Pat. No. 3,906,037, Example 3, instead of the terphenylsulfonic acid salts, has a strongly lightened, pale coloration.
- 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 for 15 minutes with 2.5% of a sulfite-based leather greasing agent based on trans in 100% of a liquor at 40 ° C. and then treated in the same liquor for 10 minutes with 1% of an ammonia solution containing 2.5% by weight of NH 3 contains.
- o-Terphenyl-4,4 ', 4 "-trisulfonic acid is prepared by reacting 230 g each of o-terphenyl (approx. 95%) with 1,500 g of sulfuric acid monohydrate at 110 ° C. for 90 minutes and adding potassium chloride to it 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 |
|---|---|---|---|
| DE19792932688 DE2932688A1 (de) | 1979-08-11 | 1979-08-11 | Verfahren zum nachgerben mineralisch gegerbter leder mit aromatischen sulfonsaeuren |
| DE2932688 | 1979-08-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0024014A1 EP0024014A1 (de) | 1981-02-18 |
| EP0024014B1 true EP0024014B1 (de) | 1982-05-19 |
Family
ID=6078301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80104522A Expired EP0024014B1 (de) | 1979-08-11 | 1980-07-31 | Verfahren zum Nachgerben mineralisch gegerbter Leder mit aromatischen Sulfonsäuren |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0024014B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5628300A (enrdf_load_stackoverflow) |
| AR (1) | AR220483A1 (enrdf_load_stackoverflow) |
| BR (1) | BR8005016A (enrdf_load_stackoverflow) |
| DE (2) | DE2932688A1 (enrdf_load_stackoverflow) |
| ES (1) | ES494117A0 (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE58905881D1 (de) * | 1988-06-06 | 1993-11-18 | Ciba Geigy | Wässrige Lösungen von synthetischen Gerbstoffen. |
| FR2658211B1 (fr) * | 1990-02-10 | 1994-07-29 | Sandoz Sa | Utilisation de composes aromatiques contenant des groupes sulfo, comme auxiliaires d'application dans la traitement des matieres fibreuses. |
| DE4025344A1 (de) * | 1990-08-10 | 1992-02-13 | Bayer Ag | Verfahren zum nachgerben mineralisch gegerbter leder mit aromatischen sulfonsaeuren |
| SE523374C2 (sv) | 1997-07-31 | 2004-04-13 | Ericsson Telefon Ab L M | Kommunikation med hjälp av spektrumspridningsmetoder över optiska fibrer |
| JP5172228B2 (ja) | 2007-06-28 | 2013-03-27 | ミドリホクヨー株式会社 | 革 |
| RU2494151C2 (ru) | 2008-05-16 | 2013-09-27 | Мидори Хокуйо Ко., Лтд. | Верхнее покрытие |
| EP2430197B1 (en) * | 2009-05-14 | 2013-01-16 | Clariant Finance (BVI) Limited | Tanning process and tanning composition |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR959065A (enrdf_load_stackoverflow) * | 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 |
| GB1302533A (enrdf_load_stackoverflow) * | 1969-09-30 | 1973-01-10 | ||
| DE2743066C3 (de) * | 1977-09-24 | 1981-02-19 | Bayer Ag, 5090 Leverkusen | Farbstoffpräparationen |
-
1979
- 1979-08-11 DE DE19792932688 patent/DE2932688A1/de not_active Withdrawn
-
1980
- 1980-07-31 EP EP80104522A patent/EP0024014B1/de not_active Expired
- 1980-07-31 DE DE8080104522T patent/DE3060449D1/de not_active Expired
- 1980-08-07 JP JP10779880A patent/JPS5628300A/ja active Granted
- 1980-08-08 BR BR8005016A patent/BR8005016A/pt unknown
- 1980-08-08 ES ES494117A patent/ES494117A0/es active Granted
- 1980-08-11 AR AR282118A patent/AR220483A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ES8104420A1 (es) | 1981-03-16 |
| DE2932688A1 (de) | 1981-02-26 |
| JPS6318640B2 (enrdf_load_stackoverflow) | 1988-04-19 |
| BR8005016A (pt) | 1981-02-24 |
| AR220483A1 (es) | 1980-10-31 |
| ES494117A0 (es) | 1981-03-16 |
| DE3060449D1 (en) | 1982-07-08 |
| JPS5628300A (en) | 1981-03-19 |
| EP0024014A1 (de) | 1981-02-18 |
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