DE1619028A1 - Process for making cellulose textiles flame resistant - Google Patents
Process for making cellulose textiles flame resistantInfo
- Publication number
- DE1619028A1 DE1619028A1 DE19661619028 DE1619028A DE1619028A1 DE 1619028 A1 DE1619028 A1 DE 1619028A1 DE 19661619028 DE19661619028 DE 19661619028 DE 1619028 A DE1619028 A DE 1619028A DE 1619028 A1 DE1619028 A1 DE 1619028A1
- Authority
- DE
- Germany
- Prior art keywords
- flame resistant
- making cellulose
- cellulose textiles
- ammonia
- textiles flame
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 239000004753 textile Substances 0.000 title description 5
- 229920002678 cellulose Polymers 0.000 title description 3
- 239000001913 cellulose Substances 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002657 fibrous material Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000009988 textile finishing Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- QZHCWVOOQUPXGE-UHFFFAOYSA-N OC[P] Chemical class OC[P] QZHCWVOOQUPXGE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LSKVBJHJMLFTDB-UHFFFAOYSA-N chloro(methyl)phosphane Chemical compound CPCl LSKVBJHJMLFTDB-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007706 flame test Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- IZCXEXNXJRMUKJ-UHFFFAOYSA-N phosphanylmethanetriol Chemical compound OC(O)(O)P IZCXEXNXJRMUKJ-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
FARBWERKE HOECHST AG. vormals Meister Lucius & Brüning Aktenzeichen: P 16 19 028.6 - Fw 4594a Datum: 8. November 1968FARBWERKE HOECHST AG. formerly Master Lucius & Brüning File number: P 16 19 028.6 - Fw 4594a Date: November 8, 1968
Verfahren zum Flammfestmachen von Cellulosetextilien (Zusatz zu Patent . ... .... (Patentanmeldung P 14 69 353,e9)>Process for making cellulose textiles flame resistant (addendum to patent. ... .... (patent application P 14 69 353, e 9)>
An die Flammfestausrüstung von Cellulosetextilien werden durch das steigende Sicherheitsbedürfnis immer höhere Anforderungen gestellt, so hinsichtlich verminderter Entflammbarkeit, besserer Haltbarkeit nach der Chemischreinigung und der Naßwäsche» Außerdem soll die Ausrüstung so gesteuert werden, daß sie die Beißfestigkeit und Scheuerfestigkeit möglichst wenig vermindert.The flame retardant finish of cellulose textiles is made by the increasing need for security made ever higher demands, so in terms of reduced flammability, better Shelf life after dry cleaning and wet washing »In addition the equipment should be controlled in such a way that it increases the bite resistance and abrasion resistance reduced as little as possible.
Gegenstand des Hauptpatentes . ... .., (Patentanmeldung P 14 69 353.9) ist ein Verfahren zum Flammfestmachen von Cellulosefasern mit Phosphorverbindungen, die an Phosphor gebundene Methylolgruppen enthalten, wobei das Fasergut mit wäßrigen Lösungen der öligen und neutralen Umsetzungsprodukte aus 1 Mol Epihalogenhydrin und etwa 2 Mol Tri-hydroxymethyl-phosphin imprägniert und anschließend mit Ammoniak behandelt wird.Subject of the main patent. ... .., (Patent Application P 14 69 353.9) is a method for flameproofing cellulosic fibers with phosphorus compounds, the phosphorus bound methylol, wherein the fiber material with aqueous solutions of the oily and neutral reaction products of 1 mole of epihalohydrin and about 2 moles of tri -hydroxymethyl-phosphine is impregnated and then treated with ammonia.
Die nach diesem Verfahren erhaltenen Flammfestausrüstungen entsprechen den Prüfbedingungen laut DIN-Vorschrift 53 906 und vielen Erfordernissen der Praxis. *The flame retardant finishes obtained by this method correspond the test conditions according to DIN regulation 53 906 and many Practical requirements. *
In weiterer Ausgestaltung des Verfahrens zum Flammfestmachen von Cellulosefasern gemäß Patent , ...... (PatentanmeldungIn a further embodiment of the method for making flame resistant Cellulose fibers according to patent, ...... (patent application
P 14 69 353.9) wurde nun gefunden, daß Fasergut mit wäßrigen Lösungen der öligen und neutralen Umsetzungsprodukte aus 1 Mol Epihalogenhydrin und etwa 2 Mol Trihydroxymethylphosphxn unter Zusatz von Trisaziridinyl-phosphinoxid imprägniert und anschlieskibiä^ wird.P 14 69 353.9) has now been found that fiber material with aqueous solutions of the oily and neutral reaction products of 1 mol Epihalohydrin and about 2 mol Trihydroxymethylphosphxn with the addition of Trisaziridinylphosphinoxid and anschlieskibiä ^ will.
909838/1397909838/1397
Das Verfahren des Hauptpatentes wird in der Weise ausgeführt, daß das Fasergut oder die Gewebe mit einer etwa 5 bis 80 %igen, vorzugsweise 20 bis 40 %igen wäßrigen Lösung des Umsetzungsproduktes a*is Epihalogenhydrin und Tris-hydroxymethyl-phosphin in üblicher Weise, Z9 B. auf dem Foulard, imprägniert wird. Man wählt hierbei Aöquetscheffekte von etwa 50 bis etwa 100 % Flüssigkeitsaufnahme. Anschließend wird das Fasergut im allgemeinen in üblicher Weise bei etwa 40 bis 130°C getrocknet, wobei man Restfeuchtigkeiten von etwa 3 bis etwa 30 %, vorzugsweise 7 bis 20 %, "erreicht.The method of the main patent is carried out in such a way that the fiber material or the fabric with an approximately 5 to 80%, preferably 20 to 40%, aqueous solution of the reaction product a * is epihalohydrin and tris-hydroxymethyl-phosphine in the usual way, Z 9 B. on the foulard, is impregnated. A squeeze effect of about 50 to about 100 % liquid absorption is selected here. The fiber material is then dried in the usual way at about 40 to 130 ° C., residual moisture levels of about 3 to about 30%, preferably 7 to 20%, being achieved.
Bsi dem gemäß <ler vorliegenden Erfindung anzuwendenden Verfahren werden der Imprägnierflotte, wie sie vorstehend und im Hauptp >v ent beschrieben ist, etwa 20 bis 200 g/l Trisaziridinylpfcjsphinoxid zugesetzt. Damit wird eine Verbesserung des Flamm-S-:nutzes erreicht, auch gegenüber längerer Einwirkung von größeren Flammen. Dabei werden die Gewebe nur unwesentlich in ihren technologischen Eigenschaften geschädigt. Außerdem bleibt der textile Griff und die Möglichkeit von Nachbehandlungen (z. B. Hydrophobieren, ölabweisende Ausrüstung u„ a.) erhalten.According to the method to be used according to the present invention, about 20 to 200 g / l trisaziridinylphosphine oxide are added to the impregnation liquor, as described above and in the main paragraph. In order to improve the flame is S:-interest achieved even over prolonged exposure to larger flames. The technological properties of the tissue are only insignificantly damaged. In addition, the textile feel and the possibility of subsequent treatments (e.g. hydrophobization, oil-repellent finish, etc.) are retained.
Vorteilhaft ist es, das imprägnierte und zwischen 2 Walzen abge-It is advantageous to use the impregnated and coated between 2 rollers
o Quetschte Cellulosefasergut bei 90 bis 120 C zu trocknen, wobei der oben erwähnte Restfeuchtigkeitsgehalt zu beachten ist.o Squeezed cellulose fiber to dry at 90 to 120 C, whereby the above-mentioned residual moisture content must be observed.
Die nachfolgende Wirkung von Ammoniak kann entweder mit Ammoniakgas oder vorteilhaft auch mit wäßrigen Lösungen von etwa 3 bis 12 % von Ammoniak erfolgen. Bei Verwendung von Ammoniaklösungen ist es zweckmäßig, außerdem noch anorganische Neutralsalze, wie Natriumsulfat, Kaliumchlorid, zuzusetzen. Auch bei diesem technologisch besonders einfachen Verfahren, für das lediglich gängige Textilausrüstungsaaschinen erforderlich sind, z. B. ein 2- oder 3-Walzenfoulard, einfache Trocknungsspannrahmen und für die Naßvernetzung Jigger oder Y/aschraaschine, wird eine überraschend-gute Wasch- und Chemischreinigungsbeständigkeit erreicht.The subsequent effect of ammonia can either be with ammonia gas or advantageously also with aqueous solutions of about 3 to 12% of ammonia. When using ammonia solutions it is advisable to also add inorganic neutral salts such as sodium sulfate and potassium chloride. Even with this technologically particularly simple process for which only common textile finishing machines are required, e.g. B. a 2- or 3-roll foulard, simple drying frame and for wet crosslinking Jigger, or Y / aschraaschine, will be a surprisingly good one Wash and dry cleaning resistance achieved.
Es ist zwate.auSider französischen Patentschrift 1 177 158 bekannt,It is known from French patent specification 1,177,158,
909838/1387 BAD909838/1387 BAD
61S02861S028
aus Trisaziridinyl-phosphinoxid Imprägnierflotten für den Textilfiammschutz zu bereiten unter wahlweisem Zusatz von Ammcni&M zni bssw, oder Methylol-Phosphorverbindüngen vom Typ Tetrakishyöros'/-methylphosphoniumchlorid. Eine stufenweise Kombination, also nachträgliche Einwirkung von Ammoniak, ist dort jedoch nicht ι :igegeben. Bei der aus der französischen Patentschrift zu eatael;:: · den Möglichkeit der Kombination der drei Komponenten bildea &:-,..;*: wjie. festgestellt wurde, sogleich unlösliche Niederschläge, didas Verfahren für Imprägnierverfahxen ungeeignet machen.to prepare from trisaziridinyl phosphine oxide impregnation liquors for textile flame protection with the optional addition of Ammcni & M zni etc., or methylol-phosphorus compounds of the tetrakishyoros' / methylphosphonium chloride type. A step-by-step combination, that is, subsequent exposure to ammonia, is not given there, however. In the case of the French patent to eatael; :: · the possibility of combining the three components bildea &: -, ..; *: wjie. was found, instantly insoluble precipitates, which made the process unsuitable for impregnation processes.
sispiel 1example 1
EIa Berufsköpergewebe aus 100 % Baumwolle (280 g/m"), mercerisiert und gefärbt mit Indanthrenfarbstoffen, wird mit einer Lösung vonEIa professional twill fabric made of 100 % cotton (280 g / m "), mercerized and dyed with indanthrene dyes, is mixed with a solution of
75 g/l Trisaziridinyiphosphinoxid (80 %) und 450 g/l Propan-2-hydroxy-l-(trishydrosymethylphosphoniumhydroxid)-3-(trishydroxymethylphosphoniumchloiM) (70 %ig)75 g / l trisaziridinyiphosphine oxide (80%) and 450 g / l propane-2-hydroxy-l- (trishydrosymethylphosphonium hydroxide) -3- (trishydroxymethylphosphoniumchloiM) (70%)
imprägniert und dann auf einem 2-Walzenfoulard bei Raumtemperatiar abgequetscht. Der Abquetscheffekt beträgt 75 % Feuchtigkeitsaufnahme. Anschließend wird auf einem in der Textilausrüstung üblichen 5-Felderspannrahmen bei 120 C getrocknet. Dabei wird eine Restfeuchte von etwa 12 % innegehalten. Dann wird das Gewebe in einer geeigneten Kammer bei etwa 200C mit Ammoniakgas 10 Minuten lang behandelt. Schließlich erfolgt eine·Nachwäsche mit 2 g/l Seife unter Zugabe von 5 g/l handelsüblicher Wasserstoffsuperoxidlösung; das getrocknete Gewebe zeigt einen ausgezeichneten Flamiuschutzeffekt. Bei dem Flammtest nach DIN 53 906 entzündet sich das Gewebe auch bei doppelt so langer Flaimneinwirkung nicht.impregnated and then squeezed on a 2-roll foulard at room temperature. The squeezing effect is 75 % moisture absorption. This is followed by drying at 120 ° C. on a 5-field clamping frame that is customary in textile finishing. A residual moisture of around 12 % is retained. The tissue is then treated with ammonia gas for 10 minutes at about 20 ° C. in a suitable chamber. Finally, it is rewashed with 2 g / l soap with the addition of 5 g / l commercial hydrogen peroxide solution; the dried fabric shows an excellent anti-inflammatory effect. In the flame test according to DIN 53 906, the fabric does not ignite, even if it is exposed to the flaimn for twice as long.
BAD ORIGINALBATH ORIGINAL
•JA*■*?*"· ■■" *■ • YES * ■ *? * "· ■■" * ■
·—^G ^ · 9U9B3 8/13 97· - ^ G ^ · 9U9B3 8/13 97
Ein in der in Beispiel 1 angegebenen Weise imprägniertes Gewebe wird bei 12O°C getrocknet. Anschließend erfolgt bei 50°C eine Naßbehandlung von 15 Minuten Dauer am Jigger nit einer 10 %igen wäßrigen Ammoniaklösung. Das Gewebe wird, wie in Beispiel 1 angegeben; nachgewaschen und getrocknet und zeigt ebenfalls einen ganz ausgezeichneten Flammschutz, der mehrere Kochwäschen überdauert .A fabric impregnated in the manner indicated in Example 1 is dried at 120.degree. This is followed by a 15-minute wet treatment at 50 ° C. on a jig with a 10% aqueous ammonia solution. The fabric is as indicated in Example 1 ; washed and dried and also shows excellent flame retardancy that lasts for several washes.
CRiwiU*·";CRiwiU * · ";
909 838/1397909 838/1397
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEH0044037 | 1964-09-23 | ||
DEF44037A DE1288556B (en) | 1964-09-23 | 1964-09-23 | Process for making cellulose fibers flame resistant |
DEF0049804 | 1966-07-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1619028A1 true DE1619028A1 (en) | 1969-09-18 |
Family
ID=27210390
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF44037A Pending DE1288556B (en) | 1964-09-23 | 1964-09-23 | Process for making cellulose fibers flame resistant |
DE19661619028 Pending DE1619028A1 (en) | 1964-09-23 | 1966-07-28 | Process for making cellulose textiles flame resistant |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF44037A Pending DE1288556B (en) | 1964-09-23 | 1964-09-23 | Process for making cellulose fibers flame resistant |
Country Status (5)
Country | Link |
---|---|
BE (2) | BE670025A (en) |
CH (2) | CH432456A (en) |
DE (2) | DE1288556B (en) |
GB (1) | GB1131899A (en) |
NL (2) | NL6512332A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA826861B (en) * | 1981-09-28 | 1983-07-27 | Albright & Wilson | Flameproofing textiles |
GB9928644D0 (en) * | 1999-12-04 | 2000-02-02 | Sterling Textiles Limited | Method of treating a textile material and textile material treated thereby |
WO2003021031A1 (en) * | 2001-09-01 | 2003-03-13 | Rhodia Consumer Specialties Limited | Phosphorus compounds |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2772188A (en) * | 1953-11-18 | 1956-11-27 | Wilson A Reeves | Ammonia insolubilized methylol-phosphorus polymers and cellulosic materials impregnated therewith |
DE1067811B (en) * | 1957-01-30 | 1959-10-29 | Hoechst Ag | Process for the production of quaternary organic phosphorus compounds |
NL135656C (en) * | 1961-06-16 |
-
1964
- 1964-09-23 DE DEF44037A patent/DE1288556B/en active Pending
-
1965
- 1965-09-21 CH CH1303765A patent/CH432456A/en unknown
- 1965-09-22 NL NL6512332A patent/NL6512332A/xx unknown
- 1965-09-23 BE BE670025D patent/BE670025A/xx unknown
-
1966
- 1966-07-28 DE DE19661619028 patent/DE1619028A1/en active Pending
-
1967
- 1967-07-26 CH CH1062067A patent/CH492821A/en unknown
- 1967-07-27 NL NL6710389A patent/NL6710389A/xx unknown
- 1967-07-28 BE BE701987D patent/BE701987A/xx unknown
- 1967-07-28 GB GB3481967A patent/GB1131899A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH492821A (en) | 1970-08-14 |
NL6512332A (en) | 1966-03-24 |
GB1131899A (en) | 1968-10-30 |
CH1303765A4 (en) | 1966-12-15 |
CH1062067A4 (en) | 1970-02-13 |
NL6710389A (en) | 1968-01-29 |
DE1288556B (en) | 1969-02-06 |
BE701987A (en) | 1968-01-29 |
CH432456A (en) | 1967-09-15 |
BE670025A (en) | 1966-03-23 |
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