GB865686A - Improvements relating to water-soluble basic resins containing nitrogen and their use - Google Patents
Improvements relating to water-soluble basic resins containing nitrogen and their useInfo
- Publication number
- GB865686A GB865686A GB16613/58A GB1661358A GB865686A GB 865686 A GB865686 A GB 865686A GB 16613/58 A GB16613/58 A GB 16613/58A GB 1661358 A GB1661358 A GB 1661358A GB 865686 A GB865686 A GB 865686A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- imidazoline
- direct
- examples
- methyl
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title abstract 4
- 239000011347 resin Substances 0.000 title abstract 3
- 229920005989 resin Polymers 0.000 title abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 title abstract 2
- 239000000047 product Substances 0.000 abstract 4
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 abstract 3
- REEBTHVEGMVLIR-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1h-imidazol-2-amine Chemical compound CC1CNC(=N)N1 REEBTHVEGMVLIR-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 2
- MSYFITFSZJKRQJ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-amine Chemical class NN1CCN=C1 MSYFITFSZJKRQJ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001879 copper Chemical class 0.000 abstract 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- RZISTNHSOMNHDE-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.NC1=NCCN1 RZISTNHSOMNHDE-UHFFFAOYSA-N 0.000 abstract 1
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 abstract 1
- HYWCPNMPNFJCMD-UHFFFAOYSA-N 4,6-dichloro-n,n-diethyl-1,3,5-triazin-2-amine Chemical compound CCN(CC)C1=NC(Cl)=NC(Cl)=N1 HYWCPNMPNFJCMD-UHFFFAOYSA-N 0.000 abstract 1
- QRTBWWIIFMMESL-UHFFFAOYSA-N 4,6-dichloro-n-methyl-1,3,5-triazin-2-amine Chemical compound CNC1=NC(Cl)=NC(Cl)=N1 QRTBWWIIFMMESL-UHFFFAOYSA-N 0.000 abstract 1
- STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- NYFBLJMUQITZGQ-UHFFFAOYSA-N C(O)(O)=O.CC1N=C(NC1)N Chemical compound C(O)(O)=O.CC1N=C(NC1)N NYFBLJMUQITZGQ-UHFFFAOYSA-N 0.000 abstract 1
- YRMBZSATHVGZED-UHFFFAOYSA-N C(O)(O)=O.NC=1NCCN1 Chemical compound C(O)(O)=O.NC=1NCCN1 YRMBZSATHVGZED-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 1
- HZBTZQVWJPRVDN-UHFFFAOYSA-J copper;disodium;5-[[4-[4-[[2,6-dioxido-3-[(2-oxido-5-sulfonatophenyl)diazenyl]phenyl]diazenyl]phenyl]phenyl]diazenyl]-2-oxidobenzoate;hydron Chemical compound [H+].[H+].[Na+].[Na+].[Cu+2].C1=C([O-])C(C(=O)[O-])=CC(N=NC=2C=CC(=CC=2)C=2C=CC(=CC=2)N=NC=2C(=C(N=NC=3C(=CC=C(C=3)S([O-])(=O)=O)[O-])C=CC=2[O-])[O-])=C1 HZBTZQVWJPRVDN-UHFFFAOYSA-J 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 229940113088 dimethylacetamide Drugs 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 238000009988 textile finishing Methods 0.000 abstract 1
- 150000003918 triazines Chemical class 0.000 abstract 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- 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
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted diazines, diazoles or triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Water-soluble basic resins containing nitrogen are made by heating at temperatures from 120 DEG to 280 DEG C. amino-imidazoline compounds of the general formula:- <FORM:0865686/IV (a)/1> where A is an aliphatic or cycloaliphatic radical containing a , b -carbon atoms attached to the two nitrogen atoms in the ring, or their salts, either alone or together with organic solvents boiling between 120 DEG and 200 DEG C. and if necessary in the presence of aromatic sulphonic acids as condensing agents, until about half a mol of ammonia per mol of starting product is split off and then possibly further condensing the condensation products with formaldehyde or triazine compounds containing more than one mobile halogen atom. Specified organic solvents are tetrachloroethane, ethylene glycol, cyclohexanol, decahydronaphthalene, anisol, dimethyl formamide, dimethyl acetamide and dimethyl sulphoxide. Examples (1) to (4) describe the preparation of polymers from:-(1) 4-methyl -2- amino-imidazoline, (2) and (4) 2-amino-imidazoline and (3) 2-amino-imidazoline carbonate, 4-methyl -2- amino-imidazoline carbonate or 2-amino-imidazoline hydrochloride. Examples Examples (5) and (6) describe the cross-linking of the products of Example (2) with cyanuric chloride, 2-methyl amino -4, 6- dichloro -1, 3, 5-triazine, 2-diethylamino -4, 6- dichloro -1, 3, 5-triazine and 2-amino -4, 6- dichloro -1, 3, 5-triazine, the products of the examples being neutralized with sulphuric or hydrochloric acid. The products of the invention may be used as auxiliaries in textile finishing optionally in conjunction with soluble copper salts or complexes.ALSO:The wet fastness of dyeings with direct dyestuffs on textile materials, e.g. cotton, linen or artificial silk, is improved by treating the material in an aqueous bath, which may contain soluble copper salts or complexes, with a water-soluble basic resin made by condensing amino-imidazolines of the general formula:- <FORM:0865686/IV(c)/1> (see Group IV(a)). In the examples, cotton material dyed with:-(1) diphenyl fast brown BRL, (2) C.I. Direct Violet 48 and (5) C.I. Direct Yellow 39, C.I. Direct Red 105, C.I. Direct Green 37 or C.I. Direct Black 62 is treated with: (1) an aqueous solution containing diammine copper acetate and a neutralized condensate of 4-methyl-2-amino-imidazoline, (3) an aqueous solution of a neutralized condensate of 2-aminoimidazoline and (5) an aqueous solution of a condensate of 2-amino-imidazoline cross-linked by reaction with cyanuric chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH865686X | 1957-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB865686A true GB865686A (en) | 1961-04-19 |
Family
ID=4543617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16613/58A Expired GB865686A (en) | 1957-05-27 | 1958-05-23 | Improvements relating to water-soluble basic resins containing nitrogen and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB865686A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450646A (en) * | 1965-10-22 | 1969-06-17 | Petrolite Corp | Heterocyclic polymers |
-
1958
- 1958-05-23 GB GB16613/58A patent/GB865686A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450646A (en) * | 1965-10-22 | 1969-06-17 | Petrolite Corp | Heterocyclic polymers |
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