US2955012A - Process of tanning hides with a condensation product of an acid salt of a phenyl amine, an acid salt of a lower alkyl amine and paraformaldehyde - Google Patents
Process of tanning hides with a condensation product of an acid salt of a phenyl amine, an acid salt of a lower alkyl amine and paraformaldehyde Download PDFInfo
- Publication number
- US2955012A US2955012A US446384A US44638454A US2955012A US 2955012 A US2955012 A US 2955012A US 446384 A US446384 A US 446384A US 44638454 A US44638454 A US 44638454A US 2955012 A US2955012 A US 2955012A
- Authority
- US
- United States
- Prior art keywords
- acid salt
- tanning
- amine
- condensation product
- lower alkyl
- 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 title claims description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 title claims description 17
- 239000007859 condensation product Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 11
- 229920002866 paraformaldehyde Polymers 0.000 title claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 title claims description 8
- 150000003973 alkyl amines Chemical class 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- -1 AMINO GROUP Chemical group 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 125000002091 cationic group Chemical group 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229940073579 ethanolamine hydrochloride Drugs 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AKECHHUMANPOQX-UHFFFAOYSA-N 3-(bromomethyl)-6,7-dichloro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CC(CBr)OC2=C1C=C(Cl)C(Cl)=C2 AKECHHUMANPOQX-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000004992 toluidines Chemical class 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
- C14C3/18—Chemical tanning by organic agents using polycondensation products or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24
Definitions
- the present invention relates to water-soluble condensation products and to processes for their production.
- Tanning agents of vegetable origin are known to be anion-active and also most synthetic tanning agents have anionic character due to their content of phenolic or sulfonic acid groups.
- cationic tanning agents of amphoteric character have become known (see for instance US. patent application Ser. No. 241,693, filed August 13, 1951, and now abandoned), which consist of aromatic condensation products containing hydroxy and additionally basic amino groups. These basic groups render the condensation products soluble in acid but they are not responsible for the tanning properties of the aromatic condensation products.
- a further object is the provision of cationic tanning agents having the capacity of tanning hides directly without any pretanning step being necessary.
- Another object consists in the provision of a process for producing tanning agents having the above characteristics.
- a still further object consists in a process of tanning with the above tanning agents.
- water-soluble condensation products suitable for tanning can be obtained by melting'mixtures of salts of aromatic amines and salts of aliphatic amines with lower aliphatic aldehydes having at most two carbon atoms.
- These tanning agents which contain no phenolic groups, can be regarded as cationic.
- the cationic tanning agents of the present invention differ from the known exclusively aliphatic condensation products which can only be used for the aftertreatment of pretanned hides.
- the tanning action of the cationic tanning agents of the invention is similar to amphoteric tanning agents; like chrome tanning agents, they are applied by pretanning therewith a pickled pelt in acid solution and efiecting finish tanning by gradually neutralizing the tanning solution.
- the character of the leather treated with the tanning agents of the invention can be influenced by neutralizing the tanning agents to a pH value near the neutral point, which gives a very firm leather of light color while a softer and yellower leather is obtained by stopping the tanning process in a weakly acid medium.
- the cationic tanning agents of the invention are prepared by melting together salts of aromatic and aliphatic amines with lower aliphatic aldehydes.
- aromatic amines are aniline, the toluidines and xylidines; suitable aliphatic amines are especially ethanolamine or diethanolamine, but also aliphatic amines containing no hydroxyl groups, for instance dirnethylamine and like alkylamines, are useful.
- dicyanodiamidine can be employed in the form of its hydrochloride.
- Suitable aldehydes according to the invention are formalamples Without being restricted thereto, the parts given being by weight:
- Example 1 13 parts of aniline hydrochloride and 10 parts of ethanolamine hydrochloride are heated to 150 C. to form a homogeneous melt. Heating is then stopped and paraformaldehyde is slowly introduced into the melt with stirring; care has to be taken that the addition is carried out so that the temperature does not exceed 140 C.
- the melt turns into a homogeneous dark red mass which almost solidifies on cooling, easily dissolves in water and has a pronounced capacity for precipitating gelatine.
- the tanning agent can be separated in the form of a yellow precipitate by means of a concentrated common salt solution,
- Example 2 14.3 parts of 0-, mor p-toluidine hydrochloride or a mixture of the three isomers are mixed with 10 parts of ethanol amine hydrochloride and 3 parts of paraformaldehyde at 140 C.
- the brick-red melt easily dissolves in waterif necessary with the addition of a small quantity of acidand has a marked capacity for precipitating gelatine.
- the tanning agent precipitates from the aqueous solution with a yellowish color by addition of concentrated common salt solution or by neutralizing with an alkali metal hydroxide solution.
- Example 3 13 grams of aniline hydrochloride and 8.1 parts of dimethyl amine hydrochloride are heated to C. to form a homogeneous melt. 14.6 grams of chloral hydrate are slowly introduced into the melt; care has to be taken that the addition is carried out so that the temperature does not exceed C.
- the brown-red resin easily dissolves in water and is precipitated from tht solution in blue-grey fiakes by addition of alkali metal hydroxide solution. The precipitate can be redissolved by means of dilute acids but is insoluble in an excess quantity of alkali metal hydroxide solution.
- the resin dissolved in dilute hydrochloric acid contains free primary amino groups of aromatic origin. This is seen by the formation of an intensely red dyestufi upon addition of nitrous acid and alkaline S-naphtol solution.
- condensation -pfodufet is prepa'red rremq arr acid salt of aniline, ---an ae-id sale of etlia'rrolan'ii'ne, aiid pa'raforinaldeh'yde.
- condensation product is prepared from an acid salt of aniline, an acid salt oi paratoluidine, and-paraformaldehyde.
- condensation product is prepared from an acid salt of aniline, an
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Description
IC V Patented Oct. 4, 1960 l 2 4 r p dehyde, especially paraformaldehyde and acetaldehyde.
2,955,012 The invention is further illustratedrby the following ex- PROCESS OF TANNING HIDE'S WITH A CONDEN- SATION PRODUCT OF AN ACID SALT OF A PHENYL AMINE, AN ACID SALT OF A LOWER ALKYL AMINE AND PARAFORMALDEHYDE Adolf Kiintzel and Kurt Rosenbusch, Darmstadt, Germany, assignors to Farbenfabriken Bayer Aktiengesellshaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed July 28, 1954, Ser. No. 446,384
Claims. priority, application Germany July 30, 1953 5 Claims. (Cl. 894.24)
The present invention relates to water-soluble condensation products and to processes for their production.
Tanning agents of vegetable origin are known to be anion-active and also most synthetic tanning agents have anionic character due to their content of phenolic or sulfonic acid groups. Recently, cationic tanning agents of amphoteric character have become known (see for instance US. patent application Ser. No. 241,693, filed August 13, 1951, and now abandoned), which consist of aromatic condensation products containing hydroxy and additionally basic amino groups. These basic groups render the condensation products soluble in acid but they are not responsible for the tanning properties of the aromatic condensation products.
It is an object of this invention to provide novel cationic tanning agents.
A further object is the provision of cationic tanning agents having the capacity of tanning hides directly without any pretanning step being necessary.
Another object consists in the provision of a process for producing tanning agents having the above characteristics. A still further object consists in a process of tanning with the above tanning agents.
Still further objects will become apparent as the following specification proceeds.
In accordance with this invention it has been found that water-soluble condensation products suitable for tanning can be obtained by melting'mixtures of salts of aromatic amines and salts of aliphatic amines with lower aliphatic aldehydes having at most two carbon atoms. These tanning agents which contain no phenolic groups, can be regarded as cationic.
The cationic tanning agents of the present invention differ from the known exclusively aliphatic condensation products which can only be used for the aftertreatment of pretanned hides. The tanning action of the cationic tanning agents of the invention is similar to amphoteric tanning agents; like chrome tanning agents, they are applied by pretanning therewith a pickled pelt in acid solution and efiecting finish tanning by gradually neutralizing the tanning solution.
The character of the leather treated with the tanning agents of the invention can be influenced by neutralizing the tanning agents to a pH value near the neutral point, which gives a very firm leather of light color while a softer and yellower leather is obtained by stopping the tanning process in a weakly acid medium.
The cationic tanning agents of the invention are prepared by melting together salts of aromatic and aliphatic amines with lower aliphatic aldehydes. Examples of aromatic amines are aniline, the toluidines and xylidines; suitable aliphatic amines are especially ethanolamine or diethanolamine, but also aliphatic amines containing no hydroxyl groups, for instance dirnethylamine and like alkylamines, are useful. Furthermore, dicyanodiamidine can be employed in the form of its hydrochloride. Suitable aldehydes according to the invention are formalamples Without being restricted thereto, the parts given being by weight:
Example 1 13 parts of aniline hydrochloride and 10 parts of ethanolamine hydrochloride are heated to 150 C. to form a homogeneous melt. Heating is then stopped and paraformaldehyde is slowly introduced into the melt with stirring; care has to be taken that the addition is carried out so that the temperature does not exceed 140 C. The melt turns into a homogeneous dark red mass which almost solidifies on cooling, easily dissolves in water and has a pronounced capacity for precipitating gelatine. Upon neutralizing the aqueous solution by addition of alkali metal hydroxide solution a white precipitate forms which is insoluble in an excess quantity of the alkali metal hydroxide solution, but can be redissolved by means of acid. The tanning agent can be separated in the form of a yellow precipitate by means of a concentrated common salt solution,
Products with similar properties can be obtained by the use of 14.1 parts of diethanolamine hydrochloride,
14 parts of dicyandiamidine hydrochloride or 8.1 parts of dimethylamine hydrochloride instead of the ethanolamine hydrochloride.
Example 2 14.3 parts of 0-, mor p-toluidine hydrochloride or a mixture of the three isomers are mixed with 10 parts of ethanol amine hydrochloride and 3 parts of paraformaldehyde at 140 C. The brick-red melt easily dissolves in waterif necessary with the addition of a small quantity of acidand has a marked capacity for precipitating gelatine. The tanning agent precipitates from the aqueous solution with a yellowish color by addition of concentrated common salt solution or by neutralizing with an alkali metal hydroxide solution.
If p-toluidine hydrochloride alone is condensed in the above described manner the red melt crystallized on cooling. By pouring the melt into a large quantity of water, colorless felted needles precipitate which can be recrystallized from ethanol and melt at 136 C.
Example 3 13 grams of aniline hydrochloride and 8.1 parts of dimethyl amine hydrochloride are heated to C. to form a homogeneous melt. 14.6 grams of chloral hydrate are slowly introduced into the melt; care has to be taken that the addition is carried out so that the temperature does not exceed C. The brown-red resin easily dissolves in water and is precipitated from tht solution in blue-grey fiakes by addition of alkali metal hydroxide solution. The precipitate can be redissolved by means of dilute acids but is insoluble in an excess quantity of alkali metal hydroxide solution. The resin dissolved in dilute hydrochloric acid contains free primary amino groups of aromatic origin. This is seen by the formation of an intensely red dyestufi upon addition of nitrous acid and alkaline S-naphtol solution.
We claim:
1. A process of tanning hides which comprises pretanning the hides with an acid solution of a cationic tanning agent, said tanning agent being the condensation product obtained by melting at a temperature of about 140 C. stoichiometric amounts of an acid salt of a phenyl amine from the group consisting of aniline and lower alkyl substituted aniline, an acid salt of an amine from the group consisting of lower alkyl amine, hydroxy lower alkyl amine and dicyanodiamidine, and paraformaldehyde, and precipitating the condensation product from the melt, the amino group of the phenyl amine reniainingdree'in tl=ie""'e6i1dnsation product; and effecting finish tanning by gradually "neutralizing said tanning solution. a
2. The process of claim 1, wherein said condensation -pfodufet is prepa'red rremq arr acid salt of aniline, ---an ae-id sale of etlia'rrolan'ii'ne, aiid pa'raforinaldeh'yde.
'3. The"' 'pr'ocess of clairn -l, wherein said condensation product is prepared from an acid salt of anilinejan acid salt of diethanolamine; arid par aformaldehyde.
4. The process of claim 1, whereinsaid condensation product is prepared from an acid salt of aniline, an acid salt oi paratoluidine, and-paraformaldehyde.
5. The process of claim 1, wherein said condensation product is prepared from an acid salt of aniline, an
References Cited in the file of this patent UNITED STATES iPATENTS Petersen Sept. 9, 1940 Grimmy Sept. 7, I943 'DAlelio Nov. 16, 1943 -Gundel Jan. 4, 1944 Olpin et a1. July.5, 1949 'Ran'i'oridt Jan. 15, 1952 Nagy '-Dec.- "9, 1952
Claims (1)
1. A PROCESS OF TANNING HIDES WHICH COMPRISES PRETANNING THE HIDES WITH AN ACID SOLUTION OA A CATIONIC TANNING AGENT, SAID TANNING AGENT BEING THE CONDENSATION PRODUCT OBTAINED BY MELTING AT A TEMPERATURE OF ABOUT 140*C. STOICHIOMETRIC AMOUNTS OF AN ACID SALT OF A PHENYL AMINE FROM THE GROUP CONSISTING OF ANILINE AND LOWER ALKYL SUBSTITUTED ANILINE, AN ACID SALT OF AN AMINE FROM THE GROUP CONSISTING OF LOWER ALKYL AMINE, HYDROXY FLOWER ALKYL AMINE AND DICYANODIAMIDINE, AND PARAFORMALDEHYDE, AND PRECIPITATING THE CONDENSATION PRODUCT FROM THE MELT, THE AMINO GROUP OF THE PHENYL AMINE REMAINING FREE IN THE CONDENSATION PRODUCT, AND EFFECTING FINISH TANNING BY GRADUALLY NEUTRALIZING SAID TANNING SOLUTION.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2955012X | 1953-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2955012A true US2955012A (en) | 1960-10-04 |
Family
ID=8017500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US446384A Expired - Lifetime US2955012A (en) | 1953-07-30 | 1954-07-28 | Process of tanning hides with a condensation product of an acid salt of a phenyl amine, an acid salt of a lower alkyl amine and paraformaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2955012A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558080A (en) * | 1984-01-24 | 1985-12-10 | Dearborn Chemical Company | Stable tannin based polymer compound |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2214067A (en) * | 1937-07-03 | 1940-09-10 | Gen Aniline & Film Corp | Process for improving the fastness of dyeings |
| US2328901A (en) * | 1938-08-23 | 1943-09-07 | Rohm & Haas | Nitrogenous condensation product |
| US2334545A (en) * | 1939-08-09 | 1943-11-16 | Gen Electric | Condensation product of a urea, an aliphatic aldehyde, and a mono salt of a polyamine |
| US2338637A (en) * | 1939-06-29 | 1944-01-04 | Hydronaphthene Corp | Polyamine-aldehyde condensation product and its production |
| US2474909A (en) * | 1945-05-08 | 1949-07-05 | Celanese Corp | Fixation of pigments on textile materials |
| US2582849A (en) * | 1942-07-28 | 1952-01-15 | Octrooien Mij Activit Nv | Phenylene diamine-formaldehyde resin preparation |
| US2621102A (en) * | 1947-12-06 | 1952-12-09 | American Cyanamid Co | Tanning with sulfonate tanning agents and a formaldehydearylamine-cyanamide type compound |
-
1954
- 1954-07-28 US US446384A patent/US2955012A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2214067A (en) * | 1937-07-03 | 1940-09-10 | Gen Aniline & Film Corp | Process for improving the fastness of dyeings |
| US2328901A (en) * | 1938-08-23 | 1943-09-07 | Rohm & Haas | Nitrogenous condensation product |
| US2338637A (en) * | 1939-06-29 | 1944-01-04 | Hydronaphthene Corp | Polyamine-aldehyde condensation product and its production |
| US2334545A (en) * | 1939-08-09 | 1943-11-16 | Gen Electric | Condensation product of a urea, an aliphatic aldehyde, and a mono salt of a polyamine |
| US2582849A (en) * | 1942-07-28 | 1952-01-15 | Octrooien Mij Activit Nv | Phenylene diamine-formaldehyde resin preparation |
| US2474909A (en) * | 1945-05-08 | 1949-07-05 | Celanese Corp | Fixation of pigments on textile materials |
| US2621102A (en) * | 1947-12-06 | 1952-12-09 | American Cyanamid Co | Tanning with sulfonate tanning agents and a formaldehydearylamine-cyanamide type compound |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558080A (en) * | 1984-01-24 | 1985-12-10 | Dearborn Chemical Company | Stable tannin based polymer compound |
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