US2746838A - Process of tanning with esters of chloracetic acid - Google Patents
Process of tanning with esters of chloracetic acid Download PDFInfo
- Publication number
- US2746838A US2746838A US301386A US30138652A US2746838A US 2746838 A US2746838 A US 2746838A US 301386 A US301386 A US 301386A US 30138652 A US30138652 A US 30138652A US 2746838 A US2746838 A US 2746838A
- Authority
- US
- United States
- Prior art keywords
- tanning
- chloracetic acid
- esters
- skins
- ester
- 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
- 238000000034 method Methods 0.000 title claims description 14
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 title claims description 13
- 150000002148 esters Chemical class 0.000 title description 7
- -1 HYDROXYL COMPOUND Chemical class 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 3
- 239000010985 leather Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- JPPYCWJDINILKY-UHFFFAOYSA-N dodecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCOC(=O)CCl JPPYCWJDINILKY-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002879 macerating effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HDNSRULOUMXYKG-UHFFFAOYSA-N octadecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCl HDNSRULOUMXYKG-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 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
- This invention relates to a new tanning process for skins and hides.
- chloracetic acid esters of hydroxyl compounds containing alkyl groups of 8-25 carbon atoms, may be used for tanning purposes.
- chloracetic acid esters of the so-called fatty alcohols are particularly suitable for tanning skins and hides.
- the new tanning agents have a high aflinity for the animal collagen fibre and can be worked smoothly into the skins and/ or hides.
- the treatment should be done in the presence of acid-binding agents, as, for example, caustic alkaline, alkali carbonates, such as soda ash, ammonia, ammonium carbonate, organic nitrogen bases, such as pyridium and the like.
- acid-binding agents as, for example, caustic alkaline, alkali carbonates, such as soda ash, ammonia, ammonium carbonate, organic nitrogen bases, such as pyridium and the like.
- the leathers thus treated are of good quality and exhibit chemical resistance against aqueous ammonia or alkali solutions.
- the tanning process in accordance with the invention may also be applied in conjunction with common mineral-, vegetable-, or synthetic tanning agents, the known tanning process being applied either before or after the process of the invention.
- the properties of the tanning agents used in accordance with the invention depend to a certain extent on the character of the ester residues, so that the tanning agents adopt the character of fatty tanning agents with increasing length of the chain of the alkyl radical.
- the new tanning agents are suitable for the tanning of animal skins and hides of any kind which will be prepared in the conventional manner in the water-workshop by soaking, slackening and/or liming, deliming, macerating, and, if necessary, pickling.
- the chloracetic acid esters to be used in the tanning process can be produced in a known manner, as for example, by esterification or re-esterification of chloracetic acid or its functional derivatives, such as halides or esters, with hydroxyl compounds containing alkyl groups of 8-25 carbon atoms.
- hydroxyl compounds are preferably alcohols containing aliphatic residues of higher molecular weight, i. e., with 8-20 carbon atoms.
- Such aliphatic alcohols may be obtained by reduction of natural fats and oils or by oxidation of parafiins or by the so-called Oxo process, i. e., the reaction of CO and Hz with olefins in the presence of a cobalt catalyst.
- hydroxyl compounds for building up the esters are alkylcyclohexyl alcohols with alkyl residues of approximately C3-C18 carbon atoms, naphthenyl alcohols, aromatic oxy compounds, alkylated in the nucleus, as, for example, alkyl phenols with alkyl residues of about 8-20 carbon atoms.
- tanning agents used in accordance with the invention are chloracetic acid dodecyl ester, chloracetic acid octadecyl ester, the chloracetic acid es- 2 ters of a mixture of fatty alcohols with 10-14 carbon atoms, the chloracetic acid esters of a mixture of unsaturated aliphatic alcohols with 14-1-6 carbon atoms, furthermore the chloracetic acid esters of a mixture of alkyl phenols with '10-16 carboii'atoms in the alkyl chain.
- the process of the invention can be elfected by intimately contacting the skins or hides to be tanned with the chloracetic acid esters which are preferably employed as concentrated as possible, either as such or in solution and emulsion, respectively, in an amount of about 2-20%, based on the weight of the material to be treated. After fulling, the leather is worked upon and finished in the conventional manner.
- Example 1 Depickled rabbit skins are preliminarily treated for one hour with 0.3% hydrochloric acid, 6% common salt, and water. Then tanning is effected for one hour with 70% water, 3% common salt, and 0.5% chromium oxide in the form of weakly alkaline chromium sulfate. The leather is left wet for one week and then properly squeezed.
- tanning is effected with 16% chloracetic acid dodecyl ester and 3.5% sodium carbonate. After 15 minutes hot air at a temperature of F. is blown in. Then the leather is left for 20 days. The reaction of the leather is now practically neutral. Upon this, the leather is washed for two hours with 0.5 sodium carbonate and 200% water at 86 F.; thereafter, it is properly rinsed. Finally, the leather is staked. The leather shows a good firmness; it is soft and smooth.
- chloracetic acid dodecyl ester instead of chloracetic acid dodecyl ester, the same quantity of chloracetic acid-p-dodecyl-phenyl ester may also be applied.
- Example 2 Depickled rabbit skins are preliminarily tanned at a temperature of 86 F. with 1.5% of a 30% aqueous formaldehyde solution and 0.7% sodium bicarbonate in 200% water, the formaldehyde and sodium bicarbonate solutions being added in three portions at intervals of 30 minutes. After 3 hours of tanning, the leather is taken out and left wet. Thereafter, final tanning is done with chloracetic acid oleyl ester in the same manner as described in Example 1. The leather is thereby well tanned and obtains a smooth quality.
- chloracetic acid ester of a mixture of alcohols obtained in well known manner by addition of CO and Hz to olefins of the chain length of C12-Cie, in the presence of a cobalt catalyst and reduction of the resulting aldehydes, may also be used.
- Example 3 Depickled cleaved neat skins are tanned for two hours with 5% of a chloracetic acid ester mixture of unsaturated fatty alcohols C14-C1s and 50% water.
- the ester mixture is applied in the form of an aqueous emulsion, with the sodium salt of an alkyl sulfate mixture C1-C9 serving as emulsifier.
- the treated skins are stored for a longer time, then they are washed and dried.
- the pieces which did not show a sufficient tanning effect before storing are now well tanned, and have a good leather character.
- the leather is fulled up, rinsed for one hour with 1% sodium bicarbonate and 200% water at a temperature of 95 F. Thereafter it is dyed, liquored, and finished in the conventional manner.
- Process for tanning skins and hides which comprises contacting skins and hides with an ester of chloracetic acid and a hydroxyl compound containing an alkyl group of 8-25 carbon atoms and recovering the tanned material.
Description
r 2,746,838 e ,atented ll 'lay 22, 1956 PROCESS OF TANNING WITH ESTERS OF CHLORACETIC ACID No Drawing. Application July 28, 1952, Serial No. 301,386
7 Claims. (Cl. 894.33)
This invention relates to a new tanning process for skins and hides.
It was found that chloracetic acid esters of hydroxyl compounds, containing alkyl groups of 8-25 carbon atoms, may be used for tanning purposes.
It was further found that chloracetic acid esters of the so-called fatty alcohols are particularly suitable for tanning skins and hides.
The new tanning agents have a high aflinity for the animal collagen fibre and can be worked smoothly into the skins and/ or hides. For reasons of expediency, the treatment should be done in the presence of acid-binding agents, as, for example, caustic alkaline, alkali carbonates, such as soda ash, ammonia, ammonium carbonate, organic nitrogen bases, such as pyridium and the like. The leathers thus treated are of good quality and exhibit chemical resistance against aqueous ammonia or alkali solutions.
The tanning process in accordance with the invention may also be applied in conjunction with common mineral-, vegetable-, or synthetic tanning agents, the known tanning process being applied either before or after the process of the invention. The properties of the tanning agents used in accordance with the invention depend to a certain extent on the character of the ester residues, so that the tanning agents adopt the character of fatty tanning agents with increasing length of the chain of the alkyl radical.
The new tanning agents are suitable for the tanning of animal skins and hides of any kind which will be prepared in the conventional manner in the water-workshop by soaking, slackening and/or liming, deliming, macerating, and, if necessary, pickling.
The chloracetic acid esters to be used in the tanning process can be produced in a known manner, as for example, by esterification or re-esterification of chloracetic acid or its functional derivatives, such as halides or esters, with hydroxyl compounds containing alkyl groups of 8-25 carbon atoms. Such hydroxyl compounds are preferably alcohols containing aliphatic residues of higher molecular weight, i. e., with 8-20 carbon atoms. Such aliphatic alcohols (of at least 8 carbon atoms in the molecule), as, for example, octyl alcohol, dodecyl alcohol, octadecyl alcohol, oleyl alcohol, and the homologues or mixtures of the same, may be obtained by reduction of natural fats and oils or by oxidation of parafiins or by the so-called Oxo process, i. e., the reaction of CO and Hz with olefins in the presence of a cobalt catalyst. Further suitable hydroxyl compounds for building up the esters are alkylcyclohexyl alcohols with alkyl residues of approximately C3-C18 carbon atoms, naphthenyl alcohols, aromatic oxy compounds, alkylated in the nucleus, as, for example, alkyl phenols with alkyl residues of about 8-20 carbon atoms.
Examples for the tanning agents used in accordance with the invention are chloracetic acid dodecyl ester, chloracetic acid octadecyl ester, the chloracetic acid es- 2 ters of a mixture of fatty alcohols with 10-14 carbon atoms, the chloracetic acid esters of a mixture of unsaturated aliphatic alcohols with 14-1-6 carbon atoms, furthermore the chloracetic acid esters of a mixture of alkyl phenols with '10-16 carboii'atoms in the alkyl chain.
The process of the invention can be elfected by intimately contacting the skins or hides to be tanned with the chloracetic acid esters which are preferably employed as concentrated as possible, either as such or in solution and emulsion, respectively, in an amount of about 2-20%, based on the weight of the material to be treated. After fulling, the leather is worked upon and finished in the conventional manner.
The following examples, in which is based on the weight of the skin, further illustrate the invention without limiting the same.
Example 1 Depickled rabbit skins are preliminarily treated for one hour with 0.3% hydrochloric acid, 6% common salt, and water. Then tanning is effected for one hour with 70% water, 3% common salt, and 0.5% chromium oxide in the form of weakly alkaline chromium sulfate. The leather is left wet for one week and then properly squeezed.
Thereupon, tanning is effected with 16% chloracetic acid dodecyl ester and 3.5% sodium carbonate. After 15 minutes hot air at a temperature of F. is blown in. Then the leather is left for 20 days. The reaction of the leather is now practically neutral. Upon this, the leather is washed for two hours with 0.5 sodium carbonate and 200% water at 86 F.; thereafter, it is properly rinsed. Finally, the leather is staked. The leather shows a good firmness; it is soft and smooth.
Instead of chloracetic acid dodecyl ester, the same quantity of chloracetic acid-p-dodecyl-phenyl ester may also be applied.
Example 2 Depickled rabbit skins are preliminarily tanned at a temperature of 86 F. with 1.5% of a 30% aqueous formaldehyde solution and 0.7% sodium bicarbonate in 200% water, the formaldehyde and sodium bicarbonate solutions being added in three portions at intervals of 30 minutes. After 3 hours of tanning, the leather is taken out and left wet. Thereafter, final tanning is done with chloracetic acid oleyl ester in the same manner as described in Example 1. The leather is thereby well tanned and obtains a smooth quality.
Instead of chloracetic acid oleylester, the chloracetic acid ester of a mixture of alcohols obtained in well known manner by addition of CO and Hz to olefins of the chain length of C12-Cie, in the presence of a cobalt catalyst and reduction of the resulting aldehydes, may also be used.
Example 3 Depickled cleaved neat skins are tanned for two hours with 5% of a chloracetic acid ester mixture of unsaturated fatty alcohols C14-C1s and 50% water. The ester mixture is applied in the form of an aqueous emulsion, with the sodium salt of an alkyl sulfate mixture C1-C9 serving as emulsifier. The treated skins are stored for a longer time, then they are washed and dried. The pieces which did not show a sufficient tanning effect before storing are now well tanned, and have a good leather character. After a longer time of storage, the leather is fulled up, rinsed for one hour with 1% sodium bicarbonate and 200% water at a temperature of 95 F. Thereafter it is dyed, liquored, and finished in the conventional manner.
What is claimed is:
1. Process for tanning skins and hides which comprises contacting skins and hides with an ester of chloracetic acid and a hydroxyl compound containing an alkyl group of 8-25 carbon atoms and recovering the tanned material.
2. Process according to claim 1, in which said hydroxyl compound is a fatty alcohol. I
3. Process accordingto claim 1, in which said hydroxyl compound is an unsaturated alcohol.
4. Process according to claim 1, in which said bydroxyl compound is dodecyl alcohol.
5.Proccss according to claim 1, in which said by droxyl compound is tetradccyl alcohol.
UNITED STATES PATENTS References Cited in the file of this patent 2,131,146 Schlack Sept. 27, 1938 2,183,754 Schlack Dec. 19, 1939 2,523,324 Putnam Sept. 26, 1950 Putnam Sept. 26, 1950
Claims (1)
1. PROCESS FOR TANNING SKINS AND HIDES WHICH COMPRISES CONTACTING SKINS AND HIDES WITH AN ESTER OF CHLORACETIC ACID AND A HYDROXYL COMPOUND CONTAINING AN ALKYL GROUP OF 8-25 CABON ATOMS AND RECOVERING THE TANNED MATERIAL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US301386A US2746838A (en) | 1952-07-28 | 1952-07-28 | Process of tanning with esters of chloracetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US301386A US2746838A (en) | 1952-07-28 | 1952-07-28 | Process of tanning with esters of chloracetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2746838A true US2746838A (en) | 1956-05-22 |
Family
ID=23163129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US301386A Expired - Lifetime US2746838A (en) | 1952-07-28 | 1952-07-28 | Process of tanning with esters of chloracetic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2746838A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2131146A (en) * | 1934-12-08 | 1938-09-27 | Xx their a | |
| US2183754A (en) * | 1935-02-21 | 1939-12-19 | Ig Farbenindustrie Ag | Process of dyeing |
| US2523324A (en) * | 1947-04-23 | 1950-09-26 | United Shoe Machinery Corp | Tanning with esters of chloroformic acid in an nonaqueous medium |
| US2523325A (en) * | 1947-07-10 | 1950-09-26 | United Shoe Machinery Corp | Tanning in a nonaqueous medium |
-
1952
- 1952-07-28 US US301386A patent/US2746838A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2131146A (en) * | 1934-12-08 | 1938-09-27 | Xx their a | |
| US2183754A (en) * | 1935-02-21 | 1939-12-19 | Ig Farbenindustrie Ag | Process of dyeing |
| US2523324A (en) * | 1947-04-23 | 1950-09-26 | United Shoe Machinery Corp | Tanning with esters of chloroformic acid in an nonaqueous medium |
| US2523325A (en) * | 1947-07-10 | 1950-09-26 | United Shoe Machinery Corp | Tanning in a nonaqueous medium |
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