GB543092A - New nitrogen compounds, process for their preparation and their industrial application - Google Patents
New nitrogen compounds, process for their preparation and their industrial applicationInfo
- Publication number
- GB543092A GB543092A GB11326/40A GB1132640A GB543092A GB 543092 A GB543092 A GB 543092A GB 11326/40 A GB11326/40 A GB 11326/40A GB 1132640 A GB1132640 A GB 1132640A GB 543092 A GB543092 A GB 543092A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- heated
- urea
- added
- treated
- 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
Links
- 229910017464 nitrogen compound Inorganic materials 0.000 title abstract 3
- 150000002830 nitrogen compounds Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 34
- 239000000047 product Substances 0.000 abstract 22
- 239000004202 carbamide Substances 0.000 abstract 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 12
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 9
- 229960004418 trolamine Drugs 0.000 abstract 9
- 239000007864 aqueous solution Substances 0.000 abstract 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 229920000742 Cotton Polymers 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 235000019441 ethanol Nutrition 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 229920001864 tannin Polymers 0.000 abstract 4
- 239000001648 tannin Substances 0.000 abstract 4
- 235000018553 tannin Nutrition 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 3
- 229940073608 benzyl chloride Drugs 0.000 abstract 3
- 239000004744 fabric Substances 0.000 abstract 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 2
- 239000010985 leather Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920001131 Pulp (paper) Polymers 0.000 abstract 1
- 238000005054 agglomeration Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 239000004566 building material Substances 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000982 direct dye Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 150000002485 inorganic esters Chemical class 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000004575 stone Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- -1 trioxymethylene Chemical class 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
-
- 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
- C08G12/046—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 one being urea or thiourea
-
- 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
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5285—Polyurethanes; Polyurea; Polyguanides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
- D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16H—GEARING
- F16H9/00—Gearings for conveying rotary motion with variable gear ratio, or for reversing rotary motion, by endless flexible members
- F16H9/02—Gearings for conveying rotary motion with variable gear ratio, or for reversing rotary motion, by endless flexible members without members having orbital motion
- F16H9/04—Gearings for conveying rotary motion with variable gear ratio, or for reversing rotary motion, by endless flexible members without members having orbital motion using belts, V-belts, or ropes
- F16H9/12—Gearings for conveying rotary motion with variable gear ratio, or for reversing rotary motion, by endless flexible members without members having orbital motion using belts, V-belts, or ropes engaging a pulley built-up out of relatively axially-adjustable parts in which the belt engages the opposite flanges of the pulley directly without interposed belt-supporting members
- F16H9/16—Gearings for conveying rotary motion with variable gear ratio, or for reversing rotary motion, by endless flexible members without members having orbital motion using belts, V-belts, or ropes engaging a pulley built-up out of relatively axially-adjustable parts in which the belt engages the opposite flanges of the pulley directly without interposed belt-supporting members using two pulleys, both built-up out of adjustable conical parts
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
Abstract
543,092. Resinous condensation products ; organic nitrogen compounds ; dyeing. textiles tanning. COMPAGNIE NATIONAL DE MATIERES COLORANTES ET MANUFACTURES<SP> </SP>DE<SP> </SP>PRODUITS CHIMIQUES DU NORD REUNIES ETABLISSEMENTS KUHLMANN. July 6, 1940. No. 11326. Convention date, July 8, 1939. [Class 2 (iii) and 15 (ii),] [Also in Group VIII] Nitrogen compounds are prepared by heating together urea and an alkylolamine, and treating the product at ordinary or elevated temperatures with an ester of an inorganic acid. Alternatively, the alkylolamine may be treated with the ester at ordinary or elevated temperature, and the product heated with urea. The product of either of these processes may be treated with an aldehyde, or compounds which give rise to aldehydes, such as trioxymethylene, at ordinary or elevated temperature. Modifications comprise (a) heating the urea with the alkylolamine, heating the product with the aldehyde, and then treating the product with the ester at normal or elevated temperature and (b) heating together the urea, alkylolamine and aldehyde, and treating the product with the ester at ordinary or elevated temperature. Specified alkylolamines are mono-, di-, and tri-ethanolamine, N - #-hydroxyethyldiethylamine, N- methyl-diethanolamine, di - #-hydroxyethylaniline, #-γ-dihydroxypropylethylaniline, tri-γ-hydroxypropylamine, and N-#-γ- dihydroxypropyl - diethanolamine. Specified inorganic esters are methyl sulphate, ethyl chloride, amyl chloride, dodecyl chloride, benzyl chloride, and ethylene chloride or bromide. The nitrogen compounds produced are fairly soluble in water and may be used as glues, for the agglomeration in the cold and under pressure of pulverulent substances such as active carbons or building materials of crushed stone and the like, and in the paper, leather, textile or dyestuff industries, e.g. for improving the fastness to water of direct dyes, for increasing the affinity of cellulosic fibres for acid dyestuffs, for the fixation in paper pulp of dyestuffs containing acid groups by formation of insoluble salts of these dyestuffs, and for the precipitation or fixation in leather of natural or synthetic tannins by formation of an insoluble salt between the tannin and the condensation product. In examples, (1) triethanolamine is heated with urea, ethyl alcohol is added followed by methyl sulphate, and the alcohol is distilled off. When a cotton fabric dyed by a direct dyestuff is treated with an aqueous solution of the product, the dyeing becomes fast to water; (2) the product of example (1) is heated with formaldehyde ; (3) triethanolamine is mixed with methyl sulphate, urea is added and the mixture heated ; (4) triethanolamine is heated with urea, trioxymethylene is added and the product heated with benzaldehyde; (5) triethanolamine is heated with urea and the product treated with amyl chloride under heat and pressure. An aqueous solution of the product, which may be treated with formaldehyde, precipitates substantive dyestuffs; (6) triethanolamine is heated with urea and the product heated with ethylene bromide; (7) triethanolamine is heated with ethylene chloride and the product is heated with urea followed or not by treatment in the cold with formaldehyde. Aqueous solutions of the products improve the fastness of direct dyestuffs ; (8) diethanolamine is heated with urea and methyl sulphate added ; the product is dissolved in water, neutralized, if necessary with sodium carbonate, and heated with formaldehyde ; (9) di-#-hydroxyethyl aniline is heated with urea and methyl sulphate added. The product precipitates substantive dyestuffs from aqueous solutions; (10) N-#- hydroxyethyldiethylamine is heated with urea and methyl sulphate added ; (11) #-γ-dihydroxy-propyl-ethylaniline is heated with urea and ethyl alcohol is added, followed by methyl sulphate ; the alcohol is distilled off, and the product heated with formaldehyde ; (12) monoethanolamine is heated with urea and methyl sulphate or a mixture of methyl sulphate and benzyl chloride added; (13) triethanolamine is heated with urea and trioxymethylene, and benzyl chloride added. An aqueous solution of the product increases the fastness of direct dyestuffs on cotton ; (14) and (15) triethanolamine is treated. with methyl sulphate, the product is heated with urea and crotonaldehyde or furfural added. Aqueous solutions of the products fix direct dyestuffs on cotton fibre ; (16) a cotton fabric is impregnated with a solution of the product described in example (2), and dried. The treated fabric fixes acid dyestuffs in neutral or weak acetic acid baths; (17) hides which have undergone a preliminary treatment with vegetable tannins are treated with an aqueous solution of the product of example (2) and, after drying, are treated with a dilute solution of synthetic tannin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR860910T | 1939-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB543092A true GB543092A (en) | 1942-02-10 |
Family
ID=9336625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11326/40A Expired GB543092A (en) | 1939-07-08 | 1940-07-06 | New nitrogen compounds, process for their preparation and their industrial application |
Country Status (3)
| Country | Link |
|---|---|
| FR (1) | FR860910A (en) |
| GB (1) | GB543092A (en) |
| NL (1) | NL54113C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471188A (en) * | 1945-07-28 | 1949-05-24 | Rohm & Haas | Urea resins containing aminoalkoxy substituents |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744934A (en) * | 1951-10-19 | 1956-05-08 | Nopco Chem Co | Process for the production of choline halides |
| DE3829974A1 (en) * | 1988-09-03 | 1990-03-15 | Basf Ag | QUATERNATED CONDENSATION PRODUCTS |
-
1939
- 1939-07-08 FR FR860910D patent/FR860910A/en not_active Expired
-
1940
- 1940-03-30 NL NL97467A patent/NL54113C/en active
- 1940-07-06 GB GB11326/40A patent/GB543092A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471188A (en) * | 1945-07-28 | 1949-05-24 | Rohm & Haas | Urea resins containing aminoalkoxy substituents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR860910A (en) | 1941-01-28 |
| NL54113C (en) | 1943-03-15 |
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