US2136997A - Tanning agents - Google Patents
Tanning agents Download PDFInfo
- Publication number
- US2136997A US2136997A US125154A US12515437A US2136997A US 2136997 A US2136997 A US 2136997A US 125154 A US125154 A US 125154A US 12515437 A US12515437 A US 12515437A US 2136997 A US2136997 A US 2136997A
- Authority
- US
- United States
- Prior art keywords
- tanning
- per cent
- parts
- tanning agents
- 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.)
- Expired - Lifetime
Links
- 239000003795 chemical substances by application Substances 0.000 description 35
- 239000003792 electrolyte Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000006277 sulfonation reaction Methods 0.000 description 9
- 239000007859 condensation product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000017343 Quebracho blanco Nutrition 0.000 description 2
- 241000065615 Schinopsis balansae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 2
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000001935 peptisation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C14C3/18—Chemical tanning by organic agents using polycondensation products or precursors thereof
- C14C3/20—Chemical tanning by organic agents using polycondensation products or precursors thereof sulfonated
-
- 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
- tanning agents there may especially be mentioned all sulfo pounds of high molecular we linking several aromatic nuclei
- acids of condensation nic acids of comight obtained by i. e. the sulfonic products obtained from aromatic bodies (phenols, naphthalene, aniline etc.) and bridge-forming agents, such as aldehydes, sulfur, sulfur chloride.
- sulfo group may be introduced In this case the either directly or by esteriflcation, peptisation etc.
- the known synthetic tanning agents are far less sensitive to the action of electrolytes. Furthermore the properties of these new mixtures may be varied to a greater extent than those of the known synthetic tanning agents.
- the mixtures may,
- a mixture of, for instance, 50 parts of quebracho (soluble in the cold state, solid) and 50 parts of the powdered tanning a ent described above is dissolved in water so as to form a liquor of a strength of 10 B.
- cow pelts are tanned which already have been tanned through in the color pits.
- the leather obtained is of lighter color and a better. stretch and is more plump than that treated with quebracho alone.
- a tanning agent consisting of the sulfonation product from a mixture of a phenolic body are tanned in a drum.
- a tanning agent consisting of the sulfonation product from phenolic bodies and natural resins, esteriiied in the presence of catalysts, with a content of electrolyte not higher than 10 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
- a tanning agent consisting of the sulfonation product from a mixture'of colophony and phenol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation prodnets.
- a tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and phenol with a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
- a tanning agent consisting of the sulionation product from colophony and cresol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
- a tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and cresol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
- a tanning agent consisting of the sulfonation product from colophony and xylenol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
- a tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and xylenol with a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclea aromatic condensation products.
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)
- Phenolic Resins Or Amino Resins (AREA)
- Coloring (AREA)
Description
Patented Nov. 15 19 UNITED STATES PATENT OFFICE 2,136,997
TANNINGAGENTS Werner Asch,
Heinrich Jam, and Walter Pens on-the-Main-Hochst,
G. for
No Drawing. Application Farbenlndustrie Germany, assignorc to I.
Aktiengesellschaft, Frankt-on-the-Main, Germany rial No. 125,154. 1936 process of 8 Claims.
to tanning agents. No. 123,734, filed Arthur Voss, Walter Pense, Werner Asch entitled Tanpreparing them preparing water soluble derivatives which comprises d phenols or the obtainable by heating such mixtures with sulfonating agents and eliminating the sulfonation products hering electrolytes. sulfonic acids which to a far extent from the ad- By this process these resinas such are very sensitive to electrolytes and therefore are not very suitable as tanning agents. electrolytes but under agents become industri valuable tanning It is possible completely to remove the al conditions this is very dimcult. 0n the other hand, if all the electrolytes are not removed, there is a certain difllculty in dissolving the product and that is sometimes detrimental.
We have found to electrolytes still mixing the products tures of resins and thereof with that a profound insensibility present may be attained by obtained by sulfonating mixphenolic bodies or the esters synthetically prepared tanning agents. As such tanning agents there may especially be mentioned all sulfo pounds of high molecular we linking several aromatic nuclei,
acids of condensation nic acids of comight obtained by i. e. the sulfonic products obtained from aromatic bodies (phenols, naphthalene, aniline etc.) and bridge-forming agents, such as aldehydes, sulfur, sulfur chloride. sulfo group may be introduced In this case the either directly or by esteriflcation, peptisation etc.
In combination with the products described in the copending application mentioned above the known synthetic tanning agents are far less sensitive to the action of electrolytes. Furthermore the properties of these new mixtures may be varied to a greater extent than those of the known synthetic tanning agents. The mixtures may,
therefore, be
successfully applied in far more tanning processes of various kind than the known synthetic tanning agents.
The following examples serve to illustrate the invention, but they are not intended thereto; the parts are by weight:-
to limit it (1) parts of a resin-sulfonation product obtainable from pine resin and phenol prepared according to the afore-named Serial No. 123,734 are water at a temperature of 50 is mixed with 100 parts of a t U. S. application dissolved in 200 parts of C. The solution anning agent ob- February 10, 1937, Se- Germany Fcbrnary 14,
tained by sulfonating 81.5 parts of alpha-methyl naphthalene with parts of sulfuric acid (of 100 per cent. strength) and by peptizing into this solution 70 parts of a liquid resin made by alkaline condensation of two mols of phenol with 1 mol of paraformaldehyde. The solution is stirred at 50 C. untilit has completely become homogeneous and is brought to a pH-value of nearly 3 by the addition of caustic soda solution. Thereby the sensitivity to salt of the solution is diminished to a great extent. Calf pelts are tanned with this combination by treating them in a pit with liquors beginning with a strength of 05 B. A leather is thus obtained showing a light color and having smooth grains and a very good stretch. Y
(2) 400 parts of resinic ican colophony with tricresol are sulfonated with fuming sulfuric acid of 10 per cent. strength; as described in U. S. application Serial No. 123,- 734 the mixture is freed from electrolytes by washing it out, drying and grinding it. 200 parts of this powder are gradually added to 500 parts of a solution of tanning agents of 25 per cent. strength preparedsimilarly to Example 1--by peptizing a phenol-formaldehyde resin into butylnaphthalene sulfonic acid. With this tanning agent cow pelts strength of the liquors begins with 1 B. and is increased during the tannage upto 5B.
(3) parts of the resin-sulfonlc acid prepared according to Example 5 of U. S. application Serial No. 123,734 from 120 parts of liquid Swedish resin and 46 parts of beta-naphthol are dissolved in 200 parts of water and the solution is rendered distinctly acid with formic acid. 50 parts of a synthetic tanning sulfonic acid obtained by causing formaldehyde to react upon naphthalene sulfonic acid are stirred into the solution. The homogeneous solution is evaporated so as to form a dry substance which is pulverized. A mixture of, for instance, 50 parts of quebracho (soluble in the cold state, solid) and 50 parts of the powdered tanning a ent described above is dissolved in water so as to form a liquor of a strength of 10 B. In this liquor cow pelts are tanned which already have been tanned through in the color pits. When being treated with this combination the leather obtained is of lighter color and a better. stretch and is more plump than that treated with quebracho alone.
We claim:
1. A tanning agent consisting of the sulfonation product from a mixture of a phenolic body are tanned in a drum. The,
and a natural resin and having a content of an electrolyte not higher than 10 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
2. A tanning agent consisting of the sulfonation product from phenolic bodies and natural resins, esteriiied in the presence of catalysts, with a content of electrolyte not higher than 10 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
3. A tanning agent consisting of the sulfonation product from a mixture'of colophony and phenol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation prodnets.
4. A tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and phenol with a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
5. A tanning agent consisting of the sulionation product from colophony and cresol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
6. A tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and cresol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
'7. A tanning agent consisting of the sulfonation product from colophony and xylenol and having a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclear aromatic condensation products.
8. A tanning agent consisting of the sulfonation product from equimolecular proportions of colophony and xylenol with a content of electrolyte not higher than 10 per cent., calculated upon a tanning agent of 100 per cent., mixed with synthetic tanning agents of the group consisting of water soluble polynuclea aromatic condensation products. it
WERNER ASCH. HEINRICH JANZ. WALTER PENSE. ARTHUR VOSS.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE817847X | 1936-02-14 | ||
| DE2136997X | 1936-02-14 | ||
| DE490296X | 1936-02-14 | ||
| DE201010X | 1936-02-14 | ||
| DE1936I0054331 DE698980C (en) | 1936-02-14 | 1936-02-15 | Method of tanning |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2136997A true US2136997A (en) | 1938-11-15 |
Family
ID=60293621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US125154A Expired - Lifetime US2136997A (en) | 1936-02-14 | 1937-02-10 | Tanning agents |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2136997A (en) |
| CH (1) | CH201010A (en) |
| DE (1) | DE698980C (en) |
| FR (1) | FR817847A (en) |
| GB (1) | GB490296A (en) |
-
1936
- 1936-02-15 DE DE1936I0054331 patent/DE698980C/en not_active Expired
-
1937
- 1937-02-06 CH CH201010D patent/CH201010A/en unknown
- 1937-02-10 US US125154A patent/US2136997A/en not_active Expired - Lifetime
- 1937-02-15 FR FR817847D patent/FR817847A/en not_active Expired
- 1937-02-15 GB GB4463/37A patent/GB490296A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH201010A (en) | 1938-11-15 |
| FR817847A (en) | 1937-09-11 |
| DE698980C (en) | 1940-11-20 |
| GB490296A (en) | 1938-08-12 |
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