US2233805A - Triazoles - Google Patents
Triazoles Download PDFInfo
- Publication number
- US2233805A US2233805A US2233805DA US2233805A US 2233805 A US2233805 A US 2233805A US 2233805D A US2233805D A US 2233805DA US 2233805 A US2233805 A US 2233805A
- Authority
- US
- United States
- Prior art keywords
- triazoles
- guanidine
- amino
- water
- acid
- 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
- 150000003852 triazoles Chemical class 0.000 title description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- 150000004665 fatty acids Chemical class 0.000 description 18
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 16
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 125000004432 carbon atoms Chemical group C* 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 230000000240 adjuvant Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N 4H-1,2,4-triazol-3-amine Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ODLVGZFVOAHGOS-UHFFFAOYSA-N Cl.C(CCCCCCCCCCCCCCCC)NC=1N=NNC1 Chemical compound Cl.C(CCCCCCCCCCCCCCCC)NC=1N=NNC1 ODLVGZFVOAHGOS-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 2
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged Effects 0.000 description 2
- 230000001681 protective Effects 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
Definitions
- the present invention relates to nitrogeneous condensation products, the manufacture thereof, and to a process of improving textiles. Specific details may be seen from the specification following hereafter.
- fatty acids containing more than 10 carbon atoms can in a simple manner be transformed into bases by melting them with amino-guanidine.
- the amino-guanidine may, for instance, be introduced into the molten fatty acid at a raised temperature (about 140 0.). Water vapor escapes, its amount being equivalent to 2 mols in case 1 mol of fatty acid has been caused to react with 1 mol of amino-guanidine.
- the free base there is preferably used one of its salts.
- the carbonate for instance, is especially suitable in view of the high volatility of carbonic acid. If salts of less volatile acids, for instance, the chlorides, are used, it is preferable to bind the acid, after heating for a short time, by introduction of sodium carbonate or of other alkalies.
- the temperature required for the condensation depends upon the nature of the components entering into reaction and upon the conditions of reaction. In general, it is necessary to apply temperatures above C. to about 200 0., a temperature of about C. is preferred.
- the water formed as a reaction product may also be removed by azeotropic distillation, for instance, by means of benzene.
- Example 1.136 parts of amino-guanidine carbonate are slowly introduced, at 140 0., while stirring, into 284 parts of molten stearic acid.
- the melt which initially begins to foam, becomes gradually clear, carbon dioxide and water being split 01f. After 36 parts of water have been split off, the reaction is interrupted.
- the melt which solidifies to a wax-like body is soluble in dilute acids, such as hydrochloric acid.
- the product may be purified by boiling it with a dilute sodium carbonate solution in order to eliminate small amounts of unaltered parent material, which may perhaps be present.
- stearic acid there may also be used with the same success coconut oil fatty acid, oleic acid, ricinoleic acid or also halogenated fatty acids and fatty acids having a branched chain.
- the amines thus obtained are soluble in dilute acids and they remain stable even if their solution in such acids is heated for a prolonged period of time. They display valuable properties as textile adjuvants.
- Example 2 A rayon skein having a weight of 100 grams is handled, for about 30 minutes, at 40 C. in 1000 cm. of a bath containing 0.1 gram of heptadecylaminotriazole hydrochloride. After thorough rinsing and drying, the silk is very soft to the touch.
- N-alkyl or N-hydroxyalkyl derivatives may be used with the same success.
- the new softening agents bring about practically no change of shade on dyed skeins or fabrics. As some of them give rise to the formation of difiiculty soluble sulfates, it is preferable to avoid any separation in flakes-in the case of water containing sulfates-by operating in the presence of protective colloids.
- the above-described textile processing is suitable not only for pure rayon of. the most varied kinds, but also for mixed fabrics as well as for natural fibers of vegetable or animal origin, such as wool and linen.
- Triazoles of the general formula R stands for alkyl with more than 9 carbon atoms, being soluble in dilute acids and being textile adjuvants.
- the process of producing triazoles which comprises condensing a. dry salt of amino-guanidine with stearic acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are'split off.
Description
Patented Mar. 4, 1941 UNITED STATES PATENT OFFICE in Anhalt, Germany, signments, to General assignors, by mesne as- Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application October 20, 1938, Serial No. 236,030. In Germany October 28, 1937 7 Claims.
The present invention relates to nitrogeneous condensation products, the manufacture thereof, and to a process of improving textiles. Specific details may be seen from the specification following hereafter.
It has been found that fatty acids containing more than 10 carbon atoms can in a simple manner be transformed into bases by melting them with amino-guanidine. For this purpose, the amino-guanidine may, for instance, be introduced into the molten fatty acid at a raised temperature (about 140 0.). Water vapor escapes, its amount being equivalent to 2 mols in case 1 mol of fatty acid has been caused to react with 1 mol of amino-guanidine.
In this condensation, there is probably formed with ring-closure a derivative of the aminotriazole, as is shown for stearic acid in the following formulae:
Instead of the free base there is preferably used one of its salts. The carbonate, for instance, is especially suitable in view of the high volatility of carbonic acid. If salts of less volatile acids, for instance, the chlorides, are used, it is preferable to bind the acid, after heating for a short time, by introduction of sodium carbonate or of other alkalies.
The temperature required for the condensation depends upon the nature of the components entering into reaction and upon the conditions of reaction. In general, it is necessary to apply temperatures above C. to about 200 0., a temperature of about C. is preferred. The water formed as a reaction product may also be removed by azeotropic distillation, for instance, by means of benzene.
The following examples illustrate the invention, the parts being by Weight:
Example 1.136 parts of amino-guanidine carbonate are slowly introduced, at 140 0., while stirring, into 284 parts of molten stearic acid.
The melt, which initially begins to foam, becomes gradually clear, carbon dioxide and water being split 01f. After 36 parts of water have been split off, the reaction is interrupted. The melt which solidifies to a wax-like body is soluble in dilute acids, such as hydrochloric acid.
The product may be purified by boiling it with a dilute sodium carbonate solution in order to eliminate small amounts of unaltered parent material, which may perhaps be present.
Instead of stearic acid, there may also be used with the same success coconut oil fatty acid, oleic acid, ricinoleic acid or also halogenated fatty acids and fatty acids having a branched chain.
The amines thus obtained are soluble in dilute acids and they remain stable even if their solution in such acids is heated for a prolonged period of time. They display valuable properties as textile adjuvants.
Example 2.A rayon skein having a weight of 100 grams is handled, for about 30 minutes, at 40 C. in 1000 cm. of a bath containing 0.1 gram of heptadecylaminotriazole hydrochloride. After thorough rinsing and drying, the silk is very soft to the touch.
The corresponding N-alkyl or N-hydroxyalkyl derivatives may be used with the same success.
The new softening agents bring about practically no change of shade on dyed skeins or fabrics. As some of them give rise to the formation of difiiculty soluble sulfates, it is preferable to avoid any separation in flakes-in the case of water containing sulfates-by operating in the presence of protective colloids. The above-described textile processing is suitable not only for pure rayon of. the most varied kinds, but also for mixed fabrics as well as for natural fibers of vegetable or animal origin, such as wool and linen.
The invention is not limited to the specific details described, for obvious modifications may occur to a person skilled in the art.
What we claim is:
1. Triazoles of the general formula R stands for alkyl with more than 9 carbon atoms, being soluble in dilute acids and being textile adjuvants.
2. The process of producing triazoles which comprises condensing dry amino-guanidine of the formula NH.NH:
HN=C
with an unsubstituted fatty acid containing more than 10 carbon atoms by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split ofi.
3. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with an unsubstituted fatty acid containing more than 10 carbon atoms by heating to a temuntil in one operation 2 mols of water are split off.
5. The process of producing triazoles which comprises condensing a. dry salt of amino-guanidine with stearic acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are'split off.
6. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with oleic acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split oil.
7. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with coconut oil fatty acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split off.
KARL BRODERSEN.
MATHIAS QUAEDVLIEG.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2233805A true US2233805A (en) | 1941-03-04 |
Family
ID=3431773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2233805D Expired - Lifetime US2233805A (en) | Triazoles |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2233805A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476549A (en) * | 1946-10-22 | 1949-07-19 | Gen Aniline & Film Corp | 2-[vinyl-dicarboxylic acid ester]-3-amino-1, 2, 4-triazoles and process of preparing the same |
| US2744116A (en) * | 1953-12-04 | 1956-05-01 | Purdue Research Foundation | Bis-(aminotriazolyl-)-hydrocarbons |
| US2875209A (en) * | 1955-12-23 | 1959-02-24 | Bayer Ag | Process for the production of 3-(or 5)-amino-1, 2, 4-triazole |
| US2981738A (en) * | 1958-05-12 | 1961-04-25 | Allied Chem | Heterocyclic nitrogen derivatives of bis(p-dialkylaminophenyl) methane |
-
0
- US US2233805D patent/US2233805A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476549A (en) * | 1946-10-22 | 1949-07-19 | Gen Aniline & Film Corp | 2-[vinyl-dicarboxylic acid ester]-3-amino-1, 2, 4-triazoles and process of preparing the same |
| US2744116A (en) * | 1953-12-04 | 1956-05-01 | Purdue Research Foundation | Bis-(aminotriazolyl-)-hydrocarbons |
| US2875209A (en) * | 1955-12-23 | 1959-02-24 | Bayer Ag | Process for the production of 3-(or 5)-amino-1, 2, 4-triazole |
| US2981738A (en) * | 1958-05-12 | 1961-04-25 | Allied Chem | Heterocyclic nitrogen derivatives of bis(p-dialkylaminophenyl) methane |
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