PL73024B2 - - Google Patents

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Publication number
PL73024B2
PL73024B2 PL146115A PL14611571A PL73024B2 PL 73024 B2 PL73024 B2 PL 73024B2 PL 146115 A PL146115 A PL 146115A PL 14611571 A PL14611571 A PL 14611571A PL 73024 B2 PL73024 B2 PL 73024B2
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PL
Poland
Prior art keywords
formula
parts
symbols
phosphorus compound
symbol
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Application number
PL146115A
Other languages
Polish (pl)
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PL73024B1 (en
Original Assignee
Ciba — Geigy Ag
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Publication date
Priority claimed from CH198870A external-priority patent/CH541658A/en
Application filed by Ciba — Geigy Ag filed Critical Ciba — Geigy Ag
Publication of PL73024B1 publication Critical patent/PL73024B1/xx
Publication of PL73024B2 publication Critical patent/PL73024B2/pl

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014Use of organic additives
    • C08J9/0038Use of organic additives containing phosphorus
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333Esters of phosphonic acids
    • C08K5/5353Esters of phosphonic acids containing also nitrogen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes

Description

Sposobem wedlug wynalazku mozna nadawac og¬ nioodpornosc tak zwanym sztywnym i miekkim piankom poliuretanowym.Sposób niniejszy korzystnie stosuje sie równiez do nadawania ognioodpornosci powlokom poliure¬ tanowym na podlozu wlóknistym.W ponizszych przepisach wytwarzania czesci oznaczaja czesci wagowe a procenty oznaczaja pro¬ centy wagowe. Stosunek czesci wagowych do czesci objetosciowych jest taki jak grama do mililitra.Przyklad I. Do reaktora o pojemnosci 500 czesci objetosciowych, zaopatrzonego w chlodnice zwrotna, termometr i oddzielacz wody zaladowuje sie 211 czesci (1 mol) hydroksymetyloamidu kwasu 3-(dwumetylofosfono)-propionowego (produkt bez¬ wodny), 72,5 czesci 98-procentowego akryloamidu (1 mol), 0,15 czesci eteru jednometylowego hydro¬ chinonu, 1 czesc kwasu p-toluenosulfonowego oraz 200 czesci benzenu a nastepnie silnie mieszajac do¬ prowadza sie zawartosc aparatu do wrzenia pod chlodnica zwrotna i utrzymuje w tych warunkach tak dlugo dopóki nie przestanie powstawac woda.Otrzymuje sie 16 czesci wody, co odpowiada 89-pro- centowemu przereagowaniu wedlug teorii. Nastepnie mieszanine reakcyjna schladza sie do temperatury otoczenia, wylewa powoli do 2000 czesci objetoscio¬ wych acetonu i za pomoca mieszadla szybkobiezne¬ go doprowadza wytracone spolimeryzowane sklad¬ niki do stanu drobnej zawiesiny.Po odsaczeniu tych spolimeryzowanych skladni¬ ków (30 czesci) usuwa sie z przesaczu benzen i ace¬ ton w temperaturze 50°C pod zmniejszonym cisnie¬ niem.Otrzymuje sie 227 czesci cieczy o malej lepkosci, bezbarwnej i odpowiadajacej wzorowi 6. Produkt ten mozna latwo spolimeryzowac w roztworze wod¬ nym w obecnosci sladowej ilosci nadsiarczanu amo¬ nowego i w temperaturze 70°C.Przyklad II. W aparaturze opisanej w prze¬ pisie wytwarzania A umieszcza sie 211 czesci (1 mol) hydroksymetyloamidu kwasu 3-(dwumetylofosfono)- propionowego, 64 czesci (0,5 mola) dwuamidu kwa¬ su itakonowego, 0,15 czesci eteru jednometylowego hydrochinonu, 1 czesc kwasu p-toluenosulfonowego oraz 200 czesci toluenu a nastepnie silnie miesza¬ jac doprowadza sie zawartosc do wrzenia pod chlod¬ nica zwrotna. Otrzymuje sie przy tym 19 czesci wody. Nastepnie schladza sie do temperatury 60°C i mozliwie jak najbardziej usuwa toluen przez de- kantacje. Pozostalosc rozpuszcza sie w 150 czesciach objetosciowych metanolu, odsacza od nie rozpusz¬ czonych zanieczyszczen a nastepnie usuwa, sie me¬ tanol oraz pozostala ilosc toluenu w temperaturze 50°C pod zmniejszonym cisnieniem. Otrzymuje sie 264 czesci lepkiego, zóltawego produktu, rozpuszcza¬ jacego sie klarownie w wodzie, który odpowiada wzorowi 10.Przyklad III. W aparaturze opisanej w prze¬ pisie wytwarzania A umieszcza sie 48 czesci (0,127 mola) amidu kwasu 3-[dwu-(chloroetylo)-fosfono]- propionowego, 12,8 czesci N-hydroksymetyloakrylo- amidu (0,127 mola), 0,03 czesci eteru jednometylo¬ wego hydrochinonu, 0,2 czesci kwasu p-toluenosul¬ fonowego oraz 250 czesci toluenu a nastepnie, silnie mieszajac, doprowadza sie zawartosc do wrzenia pod 10 15 20 25 30 35 40 45 50 55 605 73 024 6 chlodnica zwrotna. Otrzymuje sie 2,3 czesci wody.Nastepnie schladza sie do temperatury otoczenia i usuwa mozliwie jak najbardziej toluen przez de- kantacje. Pozostalosc rozpuszcza sie w 150 czesciach objetosciowych metanolu, odsacza od nie rozpuszczo¬ nych zanieczyszczen i usuwa metanol oraz pozosta¬ la ilosc toluenu w temperaturze 50°C pod zmniej¬ szonym cisnieniem. Otrzymuje sie 57 czesci lepkiej cieczy o lekko zóltawej barwie, rozpuszczajacej sie klarownie w wodzie _i- odpowiadajacej wzorowi 11.Przyklad IV. W aparaturze, opisanej w prze¬ pisie wytwarzania A umieszcza sie 211 czesci (1 mol) amidu kwasu 3-(dwumetylofosfono)-hydroksymety- lopropionowego, 85 czesci (1 mol) amidu kwasu me¬ takrylowego, 0,17 czesci eteru jednometylowego hy¬ drochinonu, 1 czesc kwasu p-toluenosulfonowego oraz 2000 czesci benzenu a nastepnie, silnie miesza¬ jac, doprowadza sie zawartosc do wrzenia pod chlod¬ nica zwrotna. Otrzymuje sie 16,5 czesci wody. Na¬ stepnie schladza sie do temperatury 50°C i usuwa benzen pod zmniejszonym cisnieniem. Otrzymuje sie 274 czesci zóltawego, lepkiego produktu roz¬ puszczalnego w wodzie i odpowiadajacego wzoro¬ wi 12.Przyklad V. Mieszanine, skladajaca sie z 20 g powoli reagujacego poliolu, 8 g fluorotrójchlorome¬ tanu, 21,4 g dwuizocyjanianu, 4,4'-dwufenylometanu i 4 g zwiazku o wzorze 6 miesza sie w ciagu jednej minuty zwyklym mieszadlem skrzydelkowym, wy¬ konujacym 1000 obr./min. Nastepnie spieniajaca sie mase umieszcza sie natychmiast w rurze o srednicy 5,5 cm i tam pozostawia az do zakonczenia reakcji.Równoczesnie wytwarza sie tworzywo piankowe bez dodatku zwiazku o wzorze 6.Badanie ognioodpornosci. Kazda badana próbke o wymiarach 120X30X10 mm umocowuje sie kra¬ wedzia 120 mm w katowniku ustawionym pod ka¬ tem 45° wzgledem poziomu, tak aby krawedz 30 mm miala pozycje pozioma. Na próbce w odleglosci 25 mm i 100 mm umieszcza sie znaki. Próbki zapala sie w dolnym koncu palnikiem motylkowym. Otrzy¬ muje sie nastepujace wartosci: Czas palenia sie (w sekun¬ dach) Znak 25 mm Znak 100 mm Strata na wadze Próbka bez dodatku 1 spala sie cal¬ kowicie osiagniety osiagniety 100% Próbka z dodatkiem 2 9 osiagniety nie osiagniety 20% Przyklad VI. Do poliuretanowej masy do po¬ wlekania, skladajacej sie z 40 g poliestru, modyfi¬ kowanego izocyjanianem, 2 g przyspieszacza reak¬ cji i 2 g wielofunkcyjnego izocyjanianu (srodek sie¬ ciujacy) wprowadza sie 4,4 g zwiazku o wzorze 6.Mieszanina ta powleka sie tkanine bawelniana o wykonczeniu ognioodpornym (grubosc mokrej warstwy •= 1 mm) a nastepnie suszy w temperatu¬ rze 25°C. Powstaje bezbarwna powloka. Tak po¬ wleczona tkanine, poddaje sie badaniu na ognio- odpornosc wedlug DIN 53906. Czas zapalania wyr nosi 6 sekund a próbki maja dlugosc 15 cm. Rów¬ noczesnie bada sie takze powloke bez dodatku 5 zwiazku o wzorze 6.Ognioodpornosc Czas palenia sie (w sekundach) Czas zarzenia sie (w sekundach) Dlugosc wypalonego odcinka (w cm) Bez dodatku 30 — —" Z dodatkiem zwiazku o wzorze 6 0 0 4 Dodatek zwiazku o wzorze 6 nie wplywa na bar¬ we masy do powlekania, równiez i po poddaniu dzialaniu ciepla w ciagu 5 minut w temperatu¬ rze 100°C.Przyklad VII. Tkanine bawelniana juz wy¬ konczona ognioodpornie powleka sie sposobem „Re- lease" nastepujacymi preparatami poliuretanowy¬ mi: Produkt o wzorze 10 (w gramach) Produkt o wzorze 11 (w gramach) Produkt o wzorze 12 (w gramach) Dwumetyloformamid /Metyloetyloketon 1 :1 (ml) Termoplastycznazywica poliestrowo-poliuretanowa (Roztwór 30-procentowy w DMF/DMK 1 :1) | Preparat nr | 1 _^ — — 10 50 1 2 5 — — 10 50 3 ^_ 5 — 10 50 4 . — 5 10 50 Ciezar powleczonej tkaniny wynosi 490 g/m2. Po wysuszeniu powloke poddaje sie badaniu na ognio¬ odpornosc, tak jak to podano w przykladzie VI.Czas zapalania wynosi 8 sekund.Preparat nr 1 2 3 4 Czas dopalania sie (w sekundach) pali sie 0 1 0 | ¦ Dlugosc wypalo¬ nego odcinka w cm 10 10,5 10 Przyklad VIII. Mieszanine, skladajaca sie z: 20 g poliestru, zawierajacego grupy wodorotleno¬ we, 8 g fluorotrójchlorometanu, 0,2 ml przyspiesza¬ cza reakcji, 21,4 g poliestru zawierajacego grupy izocyjanianowe i 5 g zwiazku o wzorze 6 przera¬ bia sie na poliuretanowe tworzywo piankowe tak jak podano w przykladzie I. Równoczesnie wytwa¬ rza sie tworzywo piankowe bez dodatku zwiazku Czas palenia sie (w sekun¬ dach) Znak 25 mm Znak 100 mm Strata na wadze spala sie cal¬ kowicie osiagniety osiagniety 100% 9 osiagniety nie osiagniety 20% 55 Preparat nr 15 20 25 30 35 40 45 50 55 60 Czas dopalania sie (w sekundach) Dlugosc wypalo¬ nego odcinka w cm7 73 024 8 o wzorze 6. Kazda badana próbke o wymiarach 120X30X10 mm umocowuje sie tak aby krawedz 120 mm byla pozioma i zapala sie u dolu palnikiem motylkowym. Otrzymuje sie nastepujace dlugosci wypalania i straty na wadze: Dlugosc wypa¬ lania w cm Strata na wa¬ dze w % Próbka bez dodatku pali sie 75 z dodatkiem 3,75 19 PL PLThe method according to the invention can impart fire resistance to so-called rigid and soft polyurethane foams. The present method is also advantageously used to make polyurethane coatings on a fibrous substrate fire resistant. In the following manufacturing regulations, parts are parts by weight and percentages are percentages by weight. The ratio of parts by weight to parts by volume is gram to milliliter. Example I. A 500 parts by volume reactor equipped with a reflux cooler, a thermometer and a water separator is charged with 211 parts (1 mole) of 3- (dimethylphosphono) propionic acid hydroxymethylamide (anhydrous product), 72.5 parts of 98% acrylamide (1 mole), 0.15 parts of hydroquinone monomethyl ether, 1 part of p-toluenesulphonic acid and 200 parts of benzene, and then by vigorously stirring the contents of the apparatus to boil under reflux and keep under these conditions until no more water is produced. 16 parts of water are retained, corresponding to 89 percent conversion by theory. The reaction mixture is then cooled to ambient temperature, slowly poured up to 2000 parts by volume of acetone and, with the aid of a high-speed stirrer, the precipitated polymerized components are brought to a fine slurry. After draining these polymerized components (30 parts) it is removed from pass benzene and acetone at 50 ° C under reduced pressure. 227 parts of a low viscosity, colorless liquid corresponding to the formula 6 are obtained. This product can be easily polymerized in an aqueous solution in the presence of a trace amount of ammonium persulfate and at a temperature of 70 ° C. Example II. 211 parts (1 mole) of 3- (dimethylphosphono) propionic acid hydroxymethylamide, 64 parts (0.5 mole) of itaconic acid diamide, 0.15 parts of hydroquinone monomethyl ether are placed in the apparatus described in the preparation of A, 1 part of p-toluenesulfonic acid and 200 parts of toluene, and then, with strong stirring, the contents are brought to the boil under reflux. 19 parts of water are obtained. Then it is cooled to 60 ° C and the toluene is removed as much as possible by decantation. The residue is dissolved in 150 parts by volume of methanol, drained from undissolved impurities, and then the methanol and the remaining amount of toluene are removed at 50 ° C under reduced pressure. 264 parts of a viscous, yellowish, water-soluble product which corresponds to the formula 10 are obtained. 48 parts (0.127 mol) of 3- [di (chloroethyl) -phosphono] propionic acid amide, 12.8 parts of N-hydroxymethylacrylamide (0.127 mol), 0.03 parts of N-hydroxymethylacrylamide (0.127 mol) are placed in the apparatus described in the preparation A. parts of hydroquinone monomethyl ether, 0.2 parts of p-toluenesulfonic acid and 250 parts of toluene, and then, with vigorous stirring, the contents are brought to the boil under a reflux condenser of 10 15 20 25 30 35 40 45 50 55 605 73 024 6. 2.3 parts of water are obtained. It is then cooled to ambient temperature and the toluene removed as much as possible by decantation. The residue is dissolved in 150 parts by volume of methanol, drained of undissolved impurities, and the methanol and the remaining amount of toluene are removed at 50 ° C. under reduced pressure. 57 parts of a viscous liquid are obtained, slightly yellowish in color, which dissolves clearly in water and corresponds to formula 11. Example IV. 211 parts (1 mole) of 3- (dimethylphosphono) hydroxymethylpropionic acid amide, 85 parts (1 mole) of methacrylic acid amide, 0.17 parts of monomethyl ether are placed in the apparatus described in the preparation A. droquinone, 1 part p-toluenesulfonic acid and 2,000 parts benzene, and then, with vigorous stirring, the contents are brought to the boil under reflux. You get 16.5 parts of water. It is then cooled to 50 ° C. and the benzene is removed under reduced pressure. 274 parts of a yellowish, viscous, water-soluble product corresponding to the formula 12 are obtained. Example 5 A mixture consisting of 20 g of slowly reacting polyol, 8 g of fluorotrichloromethane, 21.4 g of diisocyanate, 4.4 ' -diphenylmethane and 4 g of a compound of formula VI are mixed for one minute with a conventional paddle stirrer at 1000 rpm. The foaming mass is then immediately placed in a pipe 5.5 cm in diameter and left there until the reaction is completed. At the same time, foam is produced without the addition of the compound of formula 6. Fire resistance test. Each test specimen measuring 120 × 30 × 10 mm is clamped with a 120 mm edge in an angle positioned at 45 ° to the horizontal so that the 30 mm edge is horizontal. Marks are placed on the sample at a distance of 25 mm and 100 mm. The samples are ignited at the lower end with a butterfly burner. The following values are obtained: Burn time (in seconds) Mark 25 mm Mark 100 mm Weight loss Sample without additive 1 burns completely achieved achieved 100% Sample with additive 2 9 achieved not achieved 20% Example VI . A polyurethane coating compound consisting of 40 g of isocyanate-modified polyester, 2 g of a reaction accelerator and 2 g of a multifunctional isocyanate (crosslinking agent) is charged with 4.4 g of the compound of formula 6. they are coated with a cotton fabric with a fireproof finish (wet layer thickness = 1 mm) and then dried at 25 ° C. A colorless coating is formed. The fabric so coated is subjected to a fire resistance test in accordance with DIN 53906. The ignition time is 6 seconds and the samples are 15 cm long. A coating without the addition of the compound of formula 6 is also tested at the same time. Fire resistance. Burn time (seconds). Glow time (seconds). Burn length (cm) Without addition 30 - - "With the addition of the compound of formula 6 0 0 4 The addition of the compound of formula 6 does not affect the color coatings, even after being subjected to heat for 5 minutes at 100 ° C. Example VII. A cotton fabric already finished with a flame retardant is coated with the "Re - lease "with the following polyurethane preparations: Product of Formula 10 (in grams) Product of Formula 11 (in grams) Product of Formula 12 (in grams) Dimethylformamide / Methylethylketone 1: 1 (ml) Polyester-polyurethane thermoplastic resin (Solution 30- percentage in DMF / DMK 1: 1) | Preparation no | 1 _ ^ - - 10 50 1 2 5 - - 10 50 3 ^ _ 5 - 10 50 4. - 5 10 50 The weight of the coated fabric is 490 g / m2. After drying, the coating is subjected to a fire resistance test as described in Example VI. The ignition time is 8 seconds. Preparation No. 1 2 3 4 Afterburn time (seconds) burns 0 1 0 | ¦ Length of the burned segment in cm 10 10.5 10 Example VIII. A mixture consisting of: 20 g of polyester containing hydroxyl groups, 8 g of fluorotrichloromethane, 0.2 ml of reaction accelerator, 21.4 g of isocyanate-containing polyester and 5 g of the compound of formula 6 is converted to polyurethane foam as shown in example I. At the same time a foam is produced without the addition of a compound Burning time (in seconds) Mark 25 mm Mark 100 mm Loss in weight burns completely achieved achieved 100% 9 achieved not achieved 20% 55 Preparation No. 15 20 25 30 35 40 45 50 55 60 Afterburning time (in seconds) The length of the burned segment in cm7 73 024 8 of formula 6. Each tested sample with dimensions of 120X30X10 mm is fixed so that the edge of 120 mm is was horizontal and ignites at the bottom with a butterfly burner. The following firing lengths and losses in weight are obtained: Firing length in cm Weight loss in% The sample without additive burns 75 with the addition of 3.75 19 PL EN

Claims (6)

1. Zastrzezenia patentowe 1. Sposób nadawania ognioodpornosci piankom lub powlokom poliuretanowym, znamienny tym, ze wprowadza sie do nich zwiazek fosforowy o wzo- 10 15 rze 1, w którym symbol A oznacza grupe o wzo¬ rze 2, grupe, —COOH, —CONH2 lub —CONHCH2OR"', symbol R oznacza rodnik alkilo¬ wy o 1—18 atomach wegla lub rodnik chlorowcoal- kilowy o 1—4 atomach wegla, albo rodnik cyklo- alkilowy lub arylowy, symbole R' i R" oznaczaja atomy wodoru lub rodnik alkilowy o 1—4 atomach wegla a symbole n i p oznaczaja liczbe 1 lub 2.1. Claims 1. A method of imparting fire resistance to polyurethane foams or coatings, characterized by incorporating a phosphorus compound of formula 1, in which the symbol A represents a group of formula 2, group, -COOH, CONH2 or "CONHCH2OR" ", the symbol R represents an alkyl radical of 1-18 carbon atoms or a haloalkyl radical of 1-4 carbon atoms, or a cycloalkyl or aryl radical, the symbols R 'and R" denote hydrogen atoms or an alkyl radical of 1-4 carbon atoms and the symbols n and p denote the number 1 or 2. 2. Sposób wedlug zastrz. 1, znamienny tym, ze stosuje sie zwiazek forsforowy o wzorze 3, w któ¬ rym symbole R5 i R6 oznaczaja rodniki alkilowe lub chlorowcoalkilowe z co najwyzej 4 atomami wegla, zas symbole X i Y oznaczaja rodniki metylowe lub atomy wodoru.2. The method according to claim The process of claim 1, characterized in that the phosphorus compound of formula III is used, wherein the symbols R5 and R6 represent alkyl or haloalkyl radicals with up to 4 carbon atoms, and the symbols X and Y represent methyl radicals or hydrogen atoms. 3. Sposób wedlug zastrz. 2, znamienny tym, ze stosuje sie zwiazek fosforowy o wzorze 4, w którym symbole R5 i Y maja znaczenie podane w zastrz. 2.3. The method according to p. A compound according to claim 2, characterized in that the phosphorus compound of formula 4 is used, wherein the symbols R5 and Y are as defined in claim 2. 4. Sposób wedlug zastrz. 3, znamienny tym, ze stosuje sie zwiazek fosforowy o wzorze 5, w któ¬ rym symbol R7 oznacza rodnik etylowy lub metylo¬ wy a symbol Y ma znaczenie, podane w zastrz. 2.4. The method according to p. A compound according to claim 3, characterized in that the phosphorus compound of formula 5 is used, in which the symbol R7 represents an ethyl or methyl radical, and the symbol Y has the meaning given in claim 1. 2. 5. Sposób wedlug zastrz. 4, znamienny tym, ze stosuje sie zwiazek fosforowy o wzorze5. The method according to p. The process of claim 4, wherein the phosphorus compound of formula is used 6. Rr0 (-H)2-P(-R")p-1 R-'(PC-CH2CH-C0NH-cH2-NHC0-C-C-(H)2.n(-A)n_. (-H)n-I 2-n X (-R') , ("CH2A)2 (-H)n_! Wzór! 2-n C0NH-CH2-NHC0-CH2CH2-P 0 '0-R-, 0-R, Wzór 2KI. 39b5,22/44 73 024 MKP C08g 22/44 R5-0X,0 Y P l R6-0/ xCH2-CH-C0-NH-CH2-NH-C0-C=CH2 X Wzór 3 Rr0x,0 Y P i R5-0/ NCH2-CH2-CO-NH-CH2-NH-CO-C=CH2 Wzór 4 R7-0Xp/0 Y R7-0/ NCH2-CH2- CO-NH-CH2-NH-CO-C=CH2 Wzór 5 H3C-0Xp/0 HgC-o' NCH2-CH2-C0-NH-CH2-NH-CO-CH=CH2 Wzór 6KI.391^,22/44 73024 MKP C08g 22/44 CH2=CHC0NH2 • Wzór 7 ,0CH3 H0-H2CHNC0CH2CH2-Px — x0CH3 Wzór 8 /OCHo CH2=CHC0NH-CH2-HNC0-CH,CH9 — P; 2 (5XOCH3 Wzór 9 H3C-(X/O (\ /0-CH3 H3C-07 CH2-CH2-C0-NH-CH2-HN-0CC-CH2-C0-NH-CH2-HN-0C-CH2-CH2VCH3 CH2 Wzór JO CL-CH2CH2-0x /O P /K\ CL-CH2CH2-0 CH2-CH2-CO-NH-CH2-HN-OC-CH=CH2 Wzor 11 H3C -0Xp/0 H3C-O CH2-CH2-C0-NH-CH2-HN-0C-C =CH2 CH3 Wzor 12' PZG Bydg., zam. 3215/74, nakl. 110+20 Cena 10 zl PL PL6. Rr0 (-H) 2-P (-R ") p-1 R - '(PC-CH2CH-CoNH-cH2-NHC0-CC- (H) 2.n (-A) n_. (-H) nI 2-n X (-R '), ("CH2A) 2 (-H) n_! Formula! 2-n C0NH-CH2-NHCO-CH2CH2-P 0' 0-R-, O-R, Formula 2KI. 39b5,22 / 44 73 024 MKP C08g 22/44 R5-0X, 0 YP l R6-0 / xCH2-CH-C0-NH-CH2-NH-C0-C = CH2 X Formula 3 Rr0x, 0 YP and R5- 0 / NCH2-CH2-CO-NH-CH2-NH-CO-C = CH2 Formula 4 R7-0Xp / 0 Y R7-0 / NCH2-CH2- CO-NH-CH2-NH-CO-C = CH2 Formula 5 H3C-0xp / 0 HgC-o 'NCH2-CH2-C0-NH-CH2-NH-CO-CH = CH2 Formula 6KI.391 ^, 22/44 73024 MKP C08g 22/44 CH2 = CHC0NH2 • Formula 7, 0CH3 H0 -H2CHNC0CH2CH2-Px - x0CH3 Formula 8 / OCHo CH2 = CHC0NH-CH2-HNC0-CH, CH9 - P; 2 (5XOCH3 Formula 9 H3C- (X / O (/ O-CH3 H3C-07 CH2-CH2-C0- NH-CH2-HN-OCC-CH2-C0-NH-CH2-HN-OC-CH2-CH2VCH3 CH2 Formula JO CL-CH2CH2-0x / OP / K \ CL-CH2CH2-0 CH2-CH2-CO-NH-CH2 -HN-OC-CH = CH2 Pattern 11 H3C -0Xp / 0 H3C-O CH2-CH2-C0-NH-CH2-HN-OC-C = CH2 CH3 Pattern 12 'PZG Bydgoszcz, order 3215/74, new 110 + 20 Price PLN 10 PL PL
PL146115A 1971-02-09 PL73024B2 (en)

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CH198870A CH541658A (en) 1970-02-11 1970-02-11 Flame-proofing of polyurethane coatings on textile substrates

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PL73024B1 PL73024B1 (en) 1974-08-30
PL73024B2 true PL73024B2 (en) 1974-08-31

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