DE1131404B - Process for the production of water-insoluble, nitrogen-containing condensation products - Google Patents
Process for the production of water-insoluble, nitrogen-containing condensation productsInfo
- Publication number
- DE1131404B DE1131404B DEF25873A DEF0025873A DE1131404B DE 1131404 B DE1131404 B DE 1131404B DE F25873 A DEF25873 A DE F25873A DE F0025873 A DEF0025873 A DE F0025873A DE 1131404 B DE1131404 B DE 1131404B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- water
- insoluble
- condensation
- 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.)
- Pending
Links
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
- 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
- D06M15/55—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Epoxy Resins (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
F25873IVd/39cF25873IVd / 39c
BEKANNTMACHUNG DER ANMELDUNG UNDADSGABEDER AUSLEGESCHRIFT: 14. JUNI 1962NOTICE THE REGISTRATION UNDADSGABEDER EDITORIAL: JUNE 14, 1962
Die Herstellung von Kondensationsprodukten aus Polyaminen, die oxäthyliert und danach mit Epichlorhydrin quaterniert wurden, und mit Polyalkylenpolyaminen, wie Triäthylentetramin, zu unlöslichen Harzen vernetzt werden können, ist bekannt.The production of condensation products from polyamines, which are oxethylated and then with epichlorohydrin were quaternized, and with polyalkylenepolyamines, such as triethylenetetramine, to insoluble Resins can be crosslinked is known.
Es wurde nun gefunden, daß man wasserunlösliche, stickstoffhaltige Kondensationsprodukte herstellen kann, wenn man Verbindungen, die mindestens zwei endständige primäre Aminogruppen und eine entsprechende Menge an Polyäthylenglykolester enthalten bzw. aus polymerem Äthylenoxyd hergestellt worden sind, mit Polyepoxyverbindungen, die im Molekül mindestens zwei Epoxygruppen enthalten, umsetzt und gegebenenfalls die Umsetzung auf Textilmaterial vornimmt.It has now been found that water-insoluble, nitrogen-containing condensation products can be prepared can, if you have compounds that have at least two terminal primary amino groups and a corresponding Contain amount of polyethylene glycol ester or made from polymeric ethylene oxide with polyepoxy compounds that contain at least two epoxy groups in the molecule, implements and, if necessary, implements the implementation on textile material.
Das neue Verfahren beruht insbesondere darauf, daß sich die vernetzenden primären Aminogruppen zusammen mit dem polymeren Äthylenoxyd in einem Molekül befinden. Hierdurch entfällt die Verwendung eines besonderen Härtungsmitiels, beispielsweise von Polyalkylenpolyamin.The new process is based in particular on the fact that the crosslinking primary amino groups together with the polymeric ethylene oxide are in one molecule. This eliminates the Use of a special hardening agent, for example polyalkylene polyamine.
Als Verbindungen, die neben Polyäthylenglykolresten bzw. polymerem Äthylenoxyd mindestens zwei endständige primäre Aminogruppen enthalten, kommen in Frage Polyäthylenglykole, bei denen mindestens zwei OH-Gruppen nach bekannten Methoden (vgl. »Methoden der organischen Chemie« von Houben—Weyl, 1957, 4. Auflage, Bd. XI/1, S. 24 bis 96 und 108 bis 217) durch NH2-Gruppen ersetzt wurden, ferner Oxäthylierungsprodukte von Ammoniak oder mehrwertigen Alkoholen, wie z. B. Triäthanolamin, Glycerin, Butandiol, Trimethylolpropan oder mehrwertigen Aminen, wie z. B. Diäthylentriamin, bei denen ebenfalls jeweils mindestens zwei der endständigen OH-Gruppen in NH2-Gruppen übergeführt wurden, sowie weiterhin Verbindungen, die durch Umsetzung von PoIyäthylenglykolreste enthaltenden Polyepoxyden mit Ammoniak oder Polyaminen entstanden sind.Compounds which, in addition to polyethylene glycol residues or polymeric ethylene oxide, contain at least two terminal primary amino groups are polyethylene glycols in which at least two OH groups according to known methods (cf. "Methods of Organic Chemistry" by Houben-Weyl, 1957, 4. Edition, Vol. XI / 1, pp. 24 to 96 and 108 to 217) have been replaced by NH 2 groups, as well as products of oxyethylation of ammonia or polyhydric alcohols, such as. B. triethanolamine, glycerol, butanediol, trimethylolpropane or polyvalent amines, such as. B. diethylenetriamine, in each of which at least two of the terminal OH groups have also been converted into NH 2 groups, as well as compounds formed by reacting polyepoxides containing polyethylene glycol residues with ammonia or polyamines.
Als Polyepoxyde mit mindestens zwei Epoxydgruppen im Molekül kommen beispielsweise Glycidäther mehrwertiger Hydroxyverbindungen in Frage. Als Hydroxyverbindungen seien beispielsweise genannt: mehrwertige Alkohole, wie Athylenglykol, Diäthylenglykol, Polyäthylenglykole sowie die entsprechenden Propylen- und Butylengiykole, Glycerin, Sorbit, Pentaerythrit, Butandiol, Hexadecantriol, polymeres Propylenoxyd, Diphenylolpropan-dioxäthyläther, ferner Xylylenalkohol sowie Bisphenole, wie Diphenylolpropan, Diphenylolmethan. Als PoIyepoxydverbindungen kommen ferner in Betracht das sich von der Cyanursäure ableitende Triglycid-Verfahren zur HerstellungGlycide ethers, for example, are used as polyepoxides with at least two epoxy groups in the molecule polyvalent hydroxy compounds in question. Examples of hydroxy compounds include: polyhydric alcohols such as ethylene glycol, diethylene glycol, polyethylene glycols and the corresponding Propylene and butylene glycols, glycerine, sorbitol, pentaerythritol, butanediol, hexadecanetriol, polymeric propylene oxide, diphenylolpropane-dioxäthylether, also xylylene alcohol and bisphenols, such as diphenylolpropane, diphenylolmethane. As polyepoxy compounds The triglycidic process derived from cyanuric acid can also be used for the production
von wasserunlöslichen, stickstoffhaltigenof water-insoluble, nitrogenous
KondensationsproduktenCondensation products
Anmelder:Applicant:
Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Brüning,Farbwerke Hoechst Aktiengesellschaft formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Ludwig Orthner, Frankfurt/M.,Dr. Ludwig Orthner, Frankfurt / M.,
Dr. Karl Horst, Hofheim (Taunus),Dr. Karl Horst, Hofheim (Taunus),
Dr. Karl Brodersen f, Oberstauffen (Allgäu), Dr. Walter Dürsch und Dr. Karl Waldmann,Dr. Karl Brodersen f, Oberstauffen (Allgäu), Dr. Walter Dürsch and Dr. Karl Waldmann,
Frankfurt/M.-Höchst, sind als Erfinder genannt wordenFrankfurt / M.-Höchst, have been named as inventors
cyanurat, Butandiendioxyd. Als besonders geeignet haben sich erwiesen: Glycerindi- bzw. Glycerintriglycidäther und Triglycidcyanurat.cyanurate, butanedioxide. The following have proven to be particularly suitable: glycerol di- or glycerol triglycid ether and triglycide cyanurate.
Die Fixierung der Kondensationsprodukte auf dem Fasermaterial kann so vorgenommen werden, daß man Lösungen oder Dispersionen der Reaktionskomponenten und/oder Vorkondensate von Konden- sationsprodukten, gelöst in Wasser und/oder organischen Lösungsmitteln, z. B. Dioxan, Benzol, Chlorbenzol oder chlorierte niedermolekulare Kohlenwasserstoffe, auf das Fasermaterial aufbringt und dort die Vernetzung durchführt. Dabei sind die Behandlungsbäder so einzustellen, daß sie genügend lange haltbar sind.The fixation of the condensation products on the fiber material can be carried out in such a way that one solutions or dispersions of the reaction components and / or precondensates of condensate sation products dissolved in water and / or organic solvents, e.g. B. dioxane, benzene, chlorobenzene or chlorinated low molecular weight hydrocarbons, applied to the fiber material and carries out the networking there. The treatment baths are to be set so that they are sufficient have a long shelf life.
Der hohe Gehalt der härtenden Aminoverbindungen an Polyglykolresten bedingt eine gute Löslichkeit der Kondensationsprodukte, er verhindert jedoch nicht die in relativ kurzer Zeit bei erhöhter Temperatur auf dem Fasermaterial erfolgende Vernetzung zu einem unlöslichen Harz.The high content of hardening amino compounds on polyglycol residues requires good solubility of the condensation products, but it does not prevent them the crosslinking which takes place in a relatively short time at elevated temperature on the fiber material into one insoluble resin.
Besonders vorteilhaft vor allem in wirtschaftlicher Hinsicht ist es, wenn man eine wäßrige Lösung oder Dispersion der beiden Reaktionskomponenten auf die Faser bringt und erst dort die Vernetzungsreaktion durchführt. Die Haltbarkeit der Behand- It is particularly advantageous, especially from an economic point of view, if you have an aqueous solution or Brings dispersion of the two reaction components onto the fiber and only there carries out the crosslinking reaction. The durability of the treatment
2Γ.9 60S-/4392Γ.9 60S- / 439
Claims (5)
reichend.Treatment baths are suitable for this type of procedure - Example 1
reaching.
Die Härtung bzw. Auskondensation der neuen R . . . „
Kondensationsprodukte auf dem Fasermaterial er- 25 .Beispiel ζ
folgt durch kurzzeitiges Erhitzen auf Temperaturen 5 Gewichtsteile Triglycidcyanurat werden in 89 Gebis zu etwa 150° C. Dabei ist die Härtungsdauer wichtsteilen Chlorbenzol gelöst. Mit dieser Lösung abgesehen von der Art der eingesetzten Reaktions- werden Gewebe aus Polyäthylenglykolterephthalat teilnehmer selbstverständlich vor allem von der imprägniert, anschließend wird abgequetscht. Hierangewandten Härtungstemperatur abhängig. Es ist 30 nach wird das so behandelte Gewebe mit einer auch möglich, die Härtung bei niederen Tempera- Lösung aus 9 Gewichtsteilen coX-Diaminopolyglykol türen, z. B. beim Trocknen der Imprägnierungen, bei in 111 Gewichtsteilen Wasser getränkt. Das eu,a>'-Di-Temperaturen unterhalb 100° C vorzunehmen. Diese aminopolyglykol wurde aus dem Bis-benzolsulfomilden Härtungsbedingungen werden insbesondere säureester eines Polyglykols vom Molgewicht 1500 bei empfindlichen Geweben bevorzugt. 35 durch Umsetzen mit NH3 hergestellt. Nach dem Die neuen Kondensationsprodukte liefern auf Trocknen an der Luft bei 60° C erfolgt auf dem Textilien jeglicher Art, insbesondere auf Textil- Gewebe die unter Vernetzung vor sich gehende material aus hydrophoben Kunstfasern hervor- Umsetzung zu einem wasserunlöslichen Kondenragende waschechte Ausrüstungen, die z. B. für sationsprodukt, das dem Gewebe eine gute Ober-Pigmentfixierung, Appretureffekte usw. sowie insbe- 40 flächenleitfähigkeit erteilt, welche nach mehreren sondere auch für antistatische Ausrüstungen ver- Wäschen nur geringfügig zurückgeht,
wendet werden können. Gleiche Effekte erhält man, wenn man an Stelle des Gegenüber den bekannten, quaternär^ Stickstoff- Trigrycidcyanurats eine entsprechende Menge des atome, Epoxydgruppen und polymeres Äthylenoxyd Glycidäthers des 4,4'-Diphenylolpropans einsetzt und enthaltenden Kondensationsprodukten, die durch 45 die Kondensation durch 10 Minuten langes Erhitzen zusätzliche Verwendung von Härtern, wie z. B. auf 140 bis 145° C beendet,
niedermolekularen Polyalkylenpolyaminen und lang . .
andauerndem Erhitzen auf Temperaturen über eispielJ
100° C vernetzt werden müssen, um zu unlöslichen The application of the 7.5 parts by weight ω, ω'-diaminopolyglycol, Herge condensation products or their precondensates, prepared according to the invention, is made from the bis-benzenesulfonic acid ester of the poly or the two reaction components to the 5 ethylene glycol with a molecular weight of 1000 by means of um fiber material by impregnation or application with ammonia, and 1.5 parts of glycerine spray from aqueous solution and / or organic glycidyl ether are dissolved in 81 parts by weight of water, solvents or from mixtures or emulsions. With this solution, fabrics made of polyethylene glycol terephthalate are made of polyethylene glycol terephthalate in the case of Raumtemsionen of water and organic solvents. io impregnated, on a three-roll pad to 50%. The compounds used according to the invention increase in weight and then dried on with polyethylene glycol residues or compounds from the air. The already onset of polymeric ethylene oxide with at least two pri-polycondensation is brought to an end by heating in a cupboard mär amino groups have approximately the same or on a heating section at 145 ° C within solubility in water and in non-aqueous organic 15 15 minutes. Solvents such as dioxane, benzene, chlorine, the formation of the insoluble basic condensation benzene or chlorinated, low molecular weight carbon product from the glycidic compound and the hydrogen, in which the possibly water-diaminopolyglycol took place, have been found on the fabric. After nine insoluble epoxy compounds are readily soluble. Washing with a mild detergent solution from Han-These properties enable 20 dels that contain 0.2% coconut fat alcohol sulfonate (for each water-insoluble epoxy compound, a 15 minute at 60 ° Q reduces the amount of the two components from the example fabric initially achieved excellent anti-wise organic solvents, static effect not noticeable.
The hardening or condensation of the new R. . . "
Condensation products on the fiber material 25 .Example ζ
followed by brief heating to temperatures 5 parts by weight of triglycide cyanurate are converted to about 150 ° C. in 89 parts. The curing time is dissolved by parts by weight of chlorobenzene. With this solution, apart from the type of reaction used, fabrics made of polyethylene glycol terephthalate are of course primarily impregnated by the participants, and then squeezed off. The curing temperature used depends on this. It is 30 after the treated fabric is also possible to do the curing at low temperature solution of 9 parts by weight of coX-diaminopolyglycol, z. B. when drying the impregnations, soaked in 111 parts by weight of water. Make the eu, a>'- Di temperatures below 100 ° C. This aminopolyglycol was made from bis-benzenesulfomide. Curing conditions are particularly preferred acid esters of a polyglycol with a molecular weight of 1500 for sensitive fabrics. 35 produced by reacting with NH3. After the The new condensation products deliver on drying in air at 60 ° C is carried out on textiles of any kind, especially on textile fabrics, the crosslinking material made of hydrophobic synthetic fibers out- implementation to a water-insoluble condensate washable finishes that z. B. for stationery, which gives the fabric a good upper pigment fixation, finishing effects, etc. as well as surface conductivity, which decreases only slightly after several washes, especially for antistatic finishes,
can be turned. The same effects are obtained if, instead of the known quaternary ^ nitrogen trigrycidcyanurate, an appropriate amount of the atoms, epoxy groups and polymeric ethylene oxide glycidether of 4,4'-diphenylolpropane is used and the condensation products that are obtained by condensation for 10 minutes long heating additional use of hardeners, such as. B. ended at 140 to 145 ° C,
low molecular weight polyalkylenepolyamines and long. .
continuous heating to temperatures above example
100 ° C must be crosslinked in order to become insoluble
ehern, Appretur- und Füllmitteln, wie Homo- und fy
Mischpolymerisaten, zur Veredelung von Faser- Patentansprüche.
materialien zu verwenden. Für die Behandlung mit 65 1. Verfahren zur Herstellung von wasserunden genannten Produkten kommen z. B. endlose löslichen, stickstoffhaltigen Kondensationspro-Fäden, Stapelfasern, Gewebe oder Gewirke, Filme, dukten mit einem Gehalt von mindestens 50 GeBänder in Frage. wichtsprozent Polyäthylenglykolresten, dadurch 4 parts by weight of polyglycol-di- (3-amino-2-hydroxy products) have the propyl) ethers of the invention, prepared from the bis-glycidyl ether, among other things, that of a polyglycol (molecular weight about 600) with NH 3 The advantage is that the hardening can take place under gentle and 1.5 parts by weight of a mixture of glycerol conditions, preferably even with tem- di- or glycerol triglycid ether, in 45 temperatures below 100 ° C. Parts of the water are also dissolved. This solution impregnates a fabric made of poly-e-caprolactam with the use of polyalkylenepolyamines 55, disadvantages associated with the physiological unpleasantness of the amines and their unpleasant air drying at 50 ° C occurs based on the smell, largely avoided. Tissue already polycondensation. The polycondensate adhering to the condensation products of the fiber gives the fabric of the present invention, either alone or in part, a good surface conductivity and showed a combination of mono- and polyvalent aliphatic excellent resistance to repeated washing aldehydes, aminoplast precondensates, soft materials synthetic detergents or soap,
brass, finishing and filling agents such as homo- and fy
Mixed polymers, for the refinement of fiber claims.
materials to use. For the treatment with 65 1. Process for the production of water and products mentioned come z. B. endless soluble, nitrogen-containing condensation threads, staple fibers, woven or knitted fabrics, films, products with a content of at least 50 GeBänder in question. weight percent polyethylene glycol residues, thereby
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE579238D BE579238A (en) | 1958-05-31 | ||
NL239535D NL239535A (en) | 1958-05-31 | ||
NL125289D NL125289C (en) | 1958-05-31 | ||
DEF25873A DE1131404B (en) | 1958-05-31 | 1958-05-31 | Process for the production of water-insoluble, nitrogen-containing condensation products |
GB1870259A GB914152A (en) | 1958-05-31 | 1959-06-01 | New condensation products and process of preparing them |
FR796226A FR1226159A (en) | 1958-05-31 | 1959-06-01 | Preparation of condensation products of polyamine compounds and polyepoxides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF25873A DE1131404B (en) | 1958-05-31 | 1958-05-31 | Process for the production of water-insoluble, nitrogen-containing condensation products |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1131404B true DE1131404B (en) | 1962-06-14 |
Family
ID=7091798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF25873A Pending DE1131404B (en) | 1958-05-31 | 1958-05-31 | Process for the production of water-insoluble, nitrogen-containing condensation products |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE579238A (en) |
DE (1) | DE1131404B (en) |
FR (1) | FR1226159A (en) |
GB (1) | GB914152A (en) |
NL (2) | NL125289C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1246659B (en) * | 1962-05-24 | 1967-08-10 | Montedison Spa | Process for improving the dyeability of threads or fibers made from polyolefins |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE676117C (en) * | 1934-12-11 | 1939-05-26 | I G Farbenindustrie Akt Ges | Process for the production of high molecular weight polyamines |
FR1132051A (en) * | 1954-05-26 | 1957-03-05 | Ciba Geigy | New quaternary ammonium compounds, their preparation process and their use |
-
0
- NL NL239535D patent/NL239535A/xx unknown
- NL NL125289D patent/NL125289C/xx active
- BE BE579238D patent/BE579238A/xx unknown
-
1958
- 1958-05-31 DE DEF25873A patent/DE1131404B/en active Pending
-
1959
- 1959-06-01 FR FR796226A patent/FR1226159A/en not_active Expired
- 1959-06-01 GB GB1870259A patent/GB914152A/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE676117C (en) * | 1934-12-11 | 1939-05-26 | I G Farbenindustrie Akt Ges | Process for the production of high molecular weight polyamines |
FR1132051A (en) * | 1954-05-26 | 1957-03-05 | Ciba Geigy | New quaternary ammonium compounds, their preparation process and their use |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1246659B (en) * | 1962-05-24 | 1967-08-10 | Montedison Spa | Process for improving the dyeability of threads or fibers made from polyolefins |
Also Published As
Publication number | Publication date |
---|---|
BE579238A (en) | |
NL239535A (en) | |
GB914152A (en) | 1962-12-28 |
FR1226159A (en) | 1960-07-08 |
NL125289C (en) |
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