GB797175A - Improvements in addition products of polyamines - Google Patents
Improvements in addition products of polyaminesInfo
- Publication number
- GB797175A GB797175A GB23878/56A GB2387856A GB797175A GB 797175 A GB797175 A GB 797175A GB 23878/56 A GB23878/56 A GB 23878/56A GB 2387856 A GB2387856 A GB 2387856A GB 797175 A GB797175 A GB 797175A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- polyglycol
- amine
- reaction
- products
- 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
- 229920000768 polyamine Polymers 0.000 title 1
- 229920000151 polyglycol Polymers 0.000 abstract 11
- 239000010695 polyglycol Substances 0.000 abstract 11
- 150000001412 amines Chemical class 0.000 abstract 10
- 239000000047 product Substances 0.000 abstract 8
- 239000004744 fabric Substances 0.000 abstract 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 5
- 150000004820 halides Chemical group 0.000 abstract 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 4
- 229940057847 polyethylene glycol 600 Drugs 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 3
- 239000005977 Ethylene Substances 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 3
- 125000004185 ester group Chemical group 0.000 abstract 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 3
- 150000002430 hydrocarbons Chemical group 0.000 abstract 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 3
- WIFVBBXWAWZSJA-UHFFFAOYSA-N 1-n-(2-aminopropyl)propane-1,2-diamine Chemical compound CC(N)CNCC(C)N WIFVBBXWAWZSJA-UHFFFAOYSA-N 0.000 abstract 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 2
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- -1 glycol halohydrins Chemical class 0.000 abstract 2
- 238000005342 ion exchange Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 239000000741 silica gel Substances 0.000 abstract 2
- 229910002027 silica gel Inorganic materials 0.000 abstract 2
- 235000009518 sodium iodide Nutrition 0.000 abstract 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 abstract 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 229960001124 trientine Drugs 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- 229920002284 Cellulose triacetate Polymers 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000980 acid dye Substances 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000011243 crosslinked material Substances 0.000 abstract 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 238000004900 laundering Methods 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 235000010344 sodium nitrate Nutrition 0.000 abstract 1
- 239000004317 sodium nitrate Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
-
- 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
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- 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
- D06M13/325—Amines
- D06M13/332—Di- or polyamines
-
- 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
- D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
-
- 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
- D06P1/60—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 polyethers
-
- 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
- D06P1/60—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 polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Amines H2N-R-NH2 are reacted with polyglycol derivatives XCH2CH2(OCH2CH2) m-O-Z-O-(CH2CH2O)nCH2CH2X to give water-water-soluble products which can be further reacted to yield cross-linked material (see Group IV (a)); R represents a chain of methylene groups (e.g. 2-10) which may be substituted or may be interrupted by N or O; Z is a hydrocarbon residue (e.g. ethylene) or may be -CO-A-CO-or -CO-NH-A-NH-CO-, where A is e.g. phenylene or hexamethylene; X is a halide or ester group, e.g. chloride, bromide, iodide, sulphate or sulphonate; m and n are 3-40. The water-soluble products are obtained by using the amine in excess at a temperature of 10-150 DEG C., in the presence or absence of a solvent. Examples are given of the reaction between diethylene triamine and polyethylene glycol 600 dichloride in butanol. Other specified amines are hexamethylene diamine, triethylene tetramine, tetraethylene pentamine, bis-(2-aminopropyl) - amine, bis - (3 - aminopropyl)-amine and di-(3-aminopropyl)-ether. Starting materials.-Polyglycol dichlorides, di-methanesulphonates and di-toluene-p-sulphonates are made by reacting the polyglycols with thionyl chloride, methanesulphonyl chloride or toluene-p-sulphonyl chloride respectively, in the presence of pyridine or other base. Polyglycol disulphates are obtained as ammonium salts by reaction of the polyglycols with sulphamic acid. The di-iodides are prepared from the dichlorides by treatment with sodium iodide in the absence of a solvent, or in a solvent in which sodium chloride is insoluble, e.g. acetone. The polyglycol halides in which Z is -CO-A-CO- or -CO-NH-A-NH-CO- are made by reacting the glycol halohydrins with a dibasic acid (or anhydride) or di-isocyanate respectively.ALSO:The reaction products of amines H2N-R-NH2 with polyglycol derivatives XCH2CH2-(OCH2CH2) m-O-Z-O-(CH2CH2O)m\t CH2-CH2X are applied to textiles (particularly of hydrophobic or cellulose fibres) to give an antistatic finish that is fast to cleaning and laundering and to improve their receptivity for acid dyes. In the formul R represents a chain of methylene groups (e.g. 2-10) which may be substituted or may be interrupted by N or O; Z is a hydrocarbon residue (e.g. ethylene) or may be -CO-A-CO- or -CO-NH-A-NH-CO-, where A is, e.g., phenylene or hexamethylene; X is a halide or ester group, e.g. chloride, bromide, iodide, sulphate or sulphonate; m and n are 3-40. The products obtained by using an excess of the amine reactant are water-soluble but are cross-linked and rendered insoluble on the fabric by further heating, with or without further amounts of the polyglycol derivative. Instead of preparing the reaction product first, the fabric may be impregnated with solutions of the amine and the polyglycol derivative and the whole reaction carried out on the fibre. In the examples: (1) a bleached polyester taffeta fabric is padded with a solution of the product from diethylene triamine and polyethylene glycol 600 dichloride, and also polyethylene glycol 600 di-iodide, dried and cured; (2) a bleached nylon taffeta fabric is padded with a solution containing diethylene triamine and polyethylene glycol di-iodide, dried and cured; (3) the fabric of (1) is treated as in (2); (4) the process of (1) is repeated without the additional di-iodide; (5) the di-iodide of (1) is replaced by a mixture of the corresponding dichloride and sodium iodide, the latter acting also as curing catalyst. The process may also be applied to fabrics of cellulose triacetate, polyacrylonitrile, and acrylonitrile-vinylchloride copolymers. Other suitable amines besides diethylene triamine are specified.ALSO:Products are obtained by reacting amines H2N-R-NH2\t with polyglycol derivatives <FORM:0797175/IV (a)/1> at temperatures between 10 DEG and 150 DEG C. When the reactants are taken in 1 : 1 proportions the products are polymeric and cross-linked, but by using excess of amine water-soluble compounds are obtained which can be cross-linked by reaction with further quantities of the polyglycol derivative. In the formul R represents a chain of methylene groups (e.g. 2-10) which may be substituted or may be interrupted by N or O; Z is an hydrocarbon residue (e.g. ethylene) or may be-CO-A-CO-or -CO-NH-A-NH-CO-, where A is e.g. phenylene or hexamethylene; X is an halide or ester group, e.g. chloride, bromide, iodide, sulphate or sulphonate; m and n are 3-40. It is desirable to use conditions such that the reaction takes place only partially, e.g. to the extent of 70-95 per cent. The halide ions in the product can be exchanged for nitrate by allowing it to stand with aqueous sodium nitrate. The products may be used for treating textiles (see Group IV (c)) or as ion-exchange materials, especially when formed on an inert carrier such as silica gel or alumina. Examples show the reaction of diethylene triamine with polyethylene glycol 600 dichloride and di-iodide, the latter in the presence of silica gel to give an ion-exchange material. Other specified amines are hexamethylene diamine, triethylene tetramine, tetraethylene pentamine, bis - (2 - aminopropyl) - amine, bis-(3 - aminopropyl) - amine and di - (3 - aminopropyl)-ether.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US797175XA | 1956-01-25 | 1956-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB797175A true GB797175A (en) | 1958-06-25 |
Family
ID=22152347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23878/56A Expired GB797175A (en) | 1956-01-25 | 1956-08-02 | Improvements in addition products of polyamines |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE554506A (en) |
| DE (1) | DE1103284B (en) |
| FR (1) | FR1165287A (en) |
| GB (1) | GB797175A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU661279B2 (en) * | 1990-10-15 | 1995-07-20 | Precision Processes Textiles | Softening agent for natural or systhetic fibres |
| US5858023A (en) * | 1990-10-15 | 1999-01-12 | Precision Processes Textiles | Softening agents |
| EP1978051A1 (en) * | 2007-04-03 | 2008-10-08 | Rohm and Haas Electronic Materials, L.L.C. | Metal plating compositions and methods |
| US8956523B2 (en) | 2011-09-06 | 2015-02-17 | Rohm And Haas Electronic Materials Llc | Metal plating compositions and methods |
| IT201700029963A1 (en) * | 2017-03-17 | 2018-09-17 | Giovanni Bozzetto Spa | NEW POLYMERIC CARRIER FOR DYEING WITH LOW TEMPERATURE OF POLYESTER FIBER |
| CN113429558A (en) * | 2021-07-20 | 2021-09-24 | 上海益思妙医疗器械有限公司 | Preparation method of high-purity polyethylene glycol bisacrylamide |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL245471A (en) * | 1958-11-17 | 1900-01-01 | ||
| BE619144A (en) * | 1961-06-30 | |||
| US3230183A (en) * | 1961-07-07 | 1966-01-18 | Onyx Chemical Corp | Addition products of polyamines with polyalkoxy compounds and textiles treated therewith |
| DE2733973A1 (en) * | 1977-07-28 | 1979-02-15 | Basf Ag | WATER-SOLUBLE, CROSS-LINKED NITROGEN CONDENSATION PRODUCTS |
| US4360607A (en) * | 1979-09-04 | 1982-11-23 | Phillips Petroleum Company | Microwave energy sensitizing concentrate |
| US4851291A (en) * | 1986-06-19 | 1989-07-25 | The United States Of America As Represented By The Secretary Of Agriculture | Temperature adaptable textile fibers and method of preparing same |
| CN107652211B (en) * | 2017-09-22 | 2020-03-24 | 南昌航空大学 | Preparation method of hyperbranched sodium sulfonate micromolecule electron transport layer |
| CN116531183B (en) * | 2023-05-16 | 2023-11-03 | 广东美登新材料科技有限公司 | 3D composite core body of sanitary article and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE667744C (en) * | 1930-11-30 | 1938-11-19 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
| DE694991C (en) * | 1936-06-15 | 1940-08-13 | Sandoz Ag | Process for the production of high molecular weight whatn |
| DE874757C (en) * | 1942-11-20 | 1953-04-27 | Cassella Farbwerke Mainkur Ag | Process for uniform dyeing of cellulosic fibers with Kuepen or sulfur dyes and for peeling off such dyeings |
-
0
- BE BE554506D patent/BE554506A/xx unknown
-
1956
- 1956-08-02 GB GB23878/56A patent/GB797175A/en not_active Expired
- 1956-08-14 DE DEO5040A patent/DE1103284B/en active Pending
-
1957
- 1957-01-24 FR FR1165287D patent/FR1165287A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU661279B2 (en) * | 1990-10-15 | 1995-07-20 | Precision Processes Textiles | Softening agent for natural or systhetic fibres |
| US5858023A (en) * | 1990-10-15 | 1999-01-12 | Precision Processes Textiles | Softening agents |
| EP1978051A1 (en) * | 2007-04-03 | 2008-10-08 | Rohm and Haas Electronic Materials, L.L.C. | Metal plating compositions and methods |
| US8012334B2 (en) | 2007-04-03 | 2011-09-06 | Rohm And Haas Electronic Materials Llc | Metal plating compositions and methods |
| US8329018B2 (en) | 2007-04-03 | 2012-12-11 | Rohm And Haas Electronic Materials Llc | Metal plating compositions and methods |
| US8956523B2 (en) | 2011-09-06 | 2015-02-17 | Rohm And Haas Electronic Materials Llc | Metal plating compositions and methods |
| IT201700029963A1 (en) * | 2017-03-17 | 2018-09-17 | Giovanni Bozzetto Spa | NEW POLYMERIC CARRIER FOR DYEING WITH LOW TEMPERATURE OF POLYESTER FIBER |
| EP3375805A1 (en) * | 2017-03-17 | 2018-09-19 | Giovanni Bozzetto S.p.A. | Novel polymer carrier for low-temperature dye designed for polyester fibres |
| CN113429558A (en) * | 2021-07-20 | 2021-09-24 | 上海益思妙医疗器械有限公司 | Preparation method of high-purity polyethylene glycol bisacrylamide |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1165287A (en) | 1958-10-21 |
| DE1103284B (en) | 1961-03-30 |
| BE554506A (en) |
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