US1938022A - Tanning agent - Google Patents
Tanning agent Download PDFInfo
- Publication number
- US1938022A US1938022A US514306A US51430631A US1938022A US 1938022 A US1938022 A US 1938022A US 514306 A US514306 A US 514306A US 51430631 A US51430631 A US 51430631A US 1938022 A US1938022 A US 1938022A
- Authority
- US
- United States
- Prior art keywords
- acid
- sulfonyl
- tanning
- aminobenzene
- bis
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000010985 leather Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000933336 Ziziphus rignonii Species 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- -1 sulfonyl -3-aminobenzene-l-sulfonyl Chemical group 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000009963 fulling Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- KPINZNVDHXIYAR-UHFFFAOYSA-N 2-(3-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=CC(Cl)=C1 KPINZNVDHXIYAR-UHFFFAOYSA-N 0.000 description 1
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000264648 Rhus coriaria Species 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010697 neat foot oil Substances 0.000 description 1
- HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
Definitions
- the present invention relates to new tanning agents.
- the materials to be tanned in accordance with 'tann'ers practice are treated with a water soluble com- I:-IH some 1 o I, r 7 o so,
- the tanning agent is obtainable by condensing bis-(3e amino benzene sulfonyl) benzidine-mm'-disulfonic acid (compare British Letters Patent No. 333,559, Example 6) With1.2-dichlorobenzene-4 -sulio'chloride analogously to the process as described in Example 5 of the said Letters Patent and corresponds to the formula:
- the tanning requires three to five days. After tanning the skins are well rinsed and oiled from the grain. 'The finished curried leather is soft,
- plumpjandlorig fibered shows great similarity to leather tanned with vegetable tanning agents. It dif fers, however, advantageously from the latter in its pure White color and practically complete fast'ness to light.
- This re-tanning confers upon the leather a re markable fullness.
- the color of the leather is lighter than that obtained by the often practiced sumach re-tanning. 8-0
- Example 4 bis (1.2 dichlorobenzene-4-sulfonyl-3-aminobenzene-1 -sulfonyl) -diaminostilbene-disulfonic acid may be produced analogously to the process described in Example 1 of British Letters Patent No.
- Example 3 East Indian sheep skin leather is well fulled in the customary manner and rinsed in running water. Re-tanning follows in 150% of water with 10% of the tanning agent of Example 1 and 1.3% 'of lactic acid. The time of tanning amounts to three hours.
- Example 5 Degreased sheep skins (freefrom lime) treated with a pickle consisting of 0.5% of formic acid, 6% of sodium chloride, and of water'are tanned with a synthetic tanning agent of the 35 probable formula:
- the tanning is performed with the addition of 10% of the tanning agent,
- the leather 'In-the examples the tanning agents specified can be replaced ,byother representatives of the compounds denoted by the general formula.
- Such .products are, for example, the sodium salt of bis- (1 :4-dich10robenzene-2-sulfony1 3 aminobenzene-1'-su1fony1 benzidine -m m disulfonic acid.
- R stands for a benzene, naphthalene or diphenyl radical, both nuclei of the diphenyl radical beinglinked together directly or by means of a bridge
- R1 and R2 represent dior polynuclear aryl-sulfone arylamide derivatives of the benzene or naphthalene series with chain-like linkage in which the sulfone-imide groups com bining the aryl nuclei may be partly replaced by aliphatic or aromatic carboxylic acid amide groups, and wherein at least one nucleus contains a sulfonic acid group, and wherein all nuclei may be further susbtituted by halogen or all y1- or hydroxyor carboxylicor alkylacetylamino groups.
- a tanning composition the active constituent of which is a condensation product of the probable formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE377741X | 1930-02-27 | ||
| DE55698X | 1930-02-27 | ||
| DE1938022X | 1930-02-27 | ||
| DE712204X | 1930-02-27 | ||
| DE593053T | 1930-02-28 | ||
| GB11342/30A GB353046A (en) | 1930-02-27 | 1930-04-09 | Improvements in or relating to tanning |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1938022A true US1938022A (en) | 1933-12-05 |
Family
ID=60201765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US514306A Expired - Lifetime US1938022A (en) | 1930-02-27 | 1931-02-07 | Tanning agent |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US1938022A (fr) |
| BE (1) | BE377741A (fr) |
| DE (1) | DE593053C (fr) |
| FR (1) | FR712204A (fr) |
| GB (1) | GB353046A (fr) |
| NL (1) | NL29569C (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727062A (en) * | 1954-05-26 | 1955-12-13 | Gen Aniline & Film Corp | Storage stable 4, 6-diamino metanilic acids |
| US2926658A (en) * | 1957-07-19 | 1960-03-01 | Ligon Cleon | Shutter type furnace observation port |
| US4117003A (en) * | 1977-03-28 | 1978-09-26 | American Cyanamid Company | Substituted aromatic naphthalene sulfonamides |
-
1930
- 1930-02-28 DE DE1930593053D patent/DE593053C/de not_active Expired
- 1930-04-09 GB GB11342/30A patent/GB353046A/en not_active Expired
-
1931
- 1931-02-07 US US514306A patent/US1938022A/en not_active Expired - Lifetime
- 1931-02-20 NL NL55698A patent/NL29569C/nl active
- 1931-02-26 FR FR712204D patent/FR712204A/fr not_active Expired
- 1931-02-27 BE BE377741D patent/BE377741A/fr unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727062A (en) * | 1954-05-26 | 1955-12-13 | Gen Aniline & Film Corp | Storage stable 4, 6-diamino metanilic acids |
| US2926658A (en) * | 1957-07-19 | 1960-03-01 | Ligon Cleon | Shutter type furnace observation port |
| US4117003A (en) * | 1977-03-28 | 1978-09-26 | American Cyanamid Company | Substituted aromatic naphthalene sulfonamides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB353046A (en) | 1931-07-07 |
| FR712204A (fr) | 1931-09-28 |
| DE593053C (de) | 1934-02-21 |
| NL29569C (nl) | 1931-04-15 |
| BE377741A (fr) | 1931-07-31 |
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