DE1044398B - Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products with shaping - Google Patents
Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products with shapingInfo
- Publication number
- DE1044398B DE1044398B DEF22227A DEF0022227A DE1044398B DE 1044398 B DE1044398 B DE 1044398B DE F22227 A DEF22227 A DE F22227A DE F0022227 A DEF0022227 A DE F0022227A DE 1044398 B DE1044398 B DE 1044398B
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- unsaturated
- production
- shaping
- weight
- 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
- 238000006068 polycondensation reaction Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 6
- 239000011574 phosphorus Substances 0.000 title claims description 6
- 239000002131 composite material Substances 0.000 title claims description 5
- 150000003017 phosphorus Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000007493 shaping process Methods 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 title claims description 3
- 239000010425 asbestos Substances 0.000 claims 1
- 239000002685 polymerization catalyst Substances 0.000 claims 1
- 229910052895 riebeckite Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 alcohols Carboxylic acids Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6928—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
Verfahren zur Herstellung polymerer phosphorhaltiger Verbundpolymerisate auf der Grundlage von ungesättigten phosphorhaltigen Polykondensationsprodukten unter Formgebung Es wurde bereits vorgeschlagen, ungesättigte phosphorhaltige Polykondensationsprodukte durch Umsetzung von mit Hydroxylgruppen reaktionsfähigen Derivaten der Phosphorsäure, z. B. Phosphoroxychlorid oder Ester der Phosphorsäure, mit mehrwertigen oder mit Gemischen aus ein- und mehrwertigen ungesättigten Alkoholen, wobei ein Teil der ungesättigten Alkohole durch gesättigte Alkohole ersetzt sein kann, oder durch Umsetzung von mit Hydroxylgruppen reaktionsfähigen Derivaten der Phosphorsäure mit mehrwertigen bzw. Gemischen aus ein- und mehrwertigen gesättigten Alkoholen und ungesättigten Carbonsäuren oder Carbonsäurederivaten, z. B. Maleinsäure, Maleinsäureanhydrid, Maleinsäuredialkylester, wobei ein Teil der ungesättigten Carbonsäuren durch gesättigte Carbonsäuren ersetzt sein kann, herzustellen. Diese Herstellungsverfahren sind in vielfacher Weise variierbar.Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products under shaping It has already been proposed to use unsaturated phosphorus-containing polycondensation products by reaction of derivatives of phosphoric acid that are reactive with hydroxyl groups, z. B. phosphorus oxychloride or esters of phosphoric acid, with polyvalent or with Mixtures of monohydric and polyhydric unsaturated alcohols, some of which are unsaturated alcohols can be replaced by saturated alcohols, or by reaction of phosphoric acid derivatives that are reactive with hydroxyl groups with polyvalent ones or mixtures of monohydric and polyhydric saturated alcohols and unsaturated alcohols Carboxylic acids or carboxylic acid derivatives, e.g. B. maleic acid, maleic anhydride, Maleic acid dialkyl ester, with some of the unsaturated carboxylic acids replaced by saturated ones Carboxylic acids can be replaced to produce. These manufacturing processes are in can be varied in many ways.
Es wurde nun gefunden, daß man die genannten ungesättigten phosphorhaltigen Polykondensationsprodukte in unlösliche und unschmelzbare Massen überführen kann, wenn man sie, in niedermolekularen Verbindungen mit aktivierten Doppelbindungen gelöst, unter an sich bekannten Bedingungen einer Verbundpolymerisation unter Formgebung unterwirft.It has now been found that the unsaturated phosphorus-containing substances mentioned can be used Can convert polycondensation products into insoluble and infusible masses, when you get them, in low molecular weight compounds with activated double bonds dissolved, under conditions known per se, a composite polymerization with shaping subject.
Als Beispiele für die niedermolekularen Verbindungen mit aktivierten Doppelbindungen seien unter anderem genannt: Styrol, im Kern und/oder in der Seitenkette alkylierter Styrole, Vinylnaphthalin, Vinylester wie Vinylacetat, Acrylsäure und Methacrylsäure einschließlich ihrer Ester und Nitrile, Allyl- und Methallylester von gesättigten oder ungesättigten ein-und mehrbasischen Carbonsäuren, Allyl- und Methallylcarbonate, Allyl- und Methallylphosphate und -phosphonate, Ester der Vinylphosphonsäure, Triallylcyanurat, Triallyltrimesinat, niedermolekulare ungesättigte Polyester, besonders solche mit Allyl- bzw. Methallylestergruppen, sowie deren insbesondere durch Halogen substituierte Derivate.As examples of the low molecular weight compounds with activated Double bonds may be mentioned, inter alia: styrene, in the core and / or in the side chain alkylated styrenes, vinyl naphthalene, vinyl esters such as vinyl acetate, acrylic acid and Methacrylic acid including its esters and nitriles, allyl and methallyl esters of saturated or unsaturated mono- and polybasic carboxylic acids, allyl and Methallyl carbonates, allyl and methallyl phosphates and phosphonates, esters of vinyl phosphonic acid, Triallyl cyanurate, triallyl trimesinate, low molecular weight unsaturated polyesters, especially those with allyl or methallyl ester groups, and especially those with halogen substituted derivatives.
Die erfindungsgemäß erhaltenen gehärteten Produkte zeichnen sich durch Unlöslichkeit in organischen Lösungsmitteln aus; sie sind in diesen nur noch quellbar. Es handelt sich um vollkommen transparente Produkte von großer Härte, die infolge des Phosphorgehaltes nicht brennen bzw. selbstverlöschende Eigenschaften besitzen. Sie eignen sich daher für viele Verwendungszwecke, z. B. als Formkörper, als Imprägnierung von Papier und Textilien und, vor der Härtung in Form von Lacken oder sonstigen Anstrichmitteln auf Oberflächen aufgebracht, als Mittel zum Oberflächenschutz. Außerdem können sie mit verschiedenen Zusätzen, z. B. hochchlorierten Kohlenwasserstoffen oder Füllstoffen organischer oder anorganischer Natur, versehen und durch Einbettung von organischen oder anorganischen Fasern, z. B. Glasfasern, verstärkt sein.The hardened products obtained according to the invention are distinguished by Insolubility in organic solvents from; they can only be swelled in these. These are products that are completely transparent and have great hardness as a result of of the phosphorus content do not burn or have self-extinguishing properties. They are therefore suitable for many uses, e.g. B. as a molded body, as an impregnation of paper and textiles and, before hardening, in the form of varnishes or other Paints applied to surfaces as a surface protection agent. aside from that they can be mixed with various additives, e.g. B. highly chlorinated hydrocarbons or fillers of an organic or inorganic nature, provided and by embedding of organic or inorganic fibers, e.g. B. glass fibers, be reinforced.
Die nach der vorliegenden Erfindung erhaltenen gehärteten selbstverlöschenden Massen zeichnen sich gegenüber solchen Massen, die Phosphor als Reste niedermolekularer Allylester seiner Säuren enthalten, dadurch aus, daß zu ihrer Herstellung eine glatt verlaufende Vernetzung mit Vinylverbindungen, insbesondere mit Styrol, durchgeführt werden kann, während die Allylester die Nachteile besitzen, die mit der bekanntlich gegenüber Vinylverbindungen, z. B. Styrol, schlechter durchführbaren Verbundpolymerisation zusammenhängen, daß letztere also z. B. weniger hart werden. Auch sind die nach dem erfindungsgemäßen Verfahren erhaltenen gehärteten Massen besonders wirtschaftlich in der Herstellung.The hardened self-extinguishing ones obtained according to the present invention Masses stand out against those masses that contain phosphorus as residues of low molecular weight Allyl esters contain its acids, from the fact that for their preparation a smooth ongoing crosslinking with vinyl compounds, in particular with styrene, carried out while the allyl esters have the disadvantages associated with the known to vinyl compounds, e.g. B. styrene, poorly feasible composite polymerization related that the latter so z. B. become less hard. They are also after the cured compositions obtained by the process according to the invention are particularly economical in production.
Beispiel 1 Herstellung des verwendeten Polykondensationsproduktes In einem mit Thermometer, Rührwerk und Wasserabscheider mit aufgesetztem Rückflußkühler ausgerüsteten Vierhalskolben werden 144 Gewichtsteile Maleinsäuredimethylester, _ _182 Gewichtsteile Triäthylphosphat, 124 Gewichtsteile Äthylenglykol und 74 Gewichtsteile Butanol in Gegenwart von 1 Gewichtsteil Ca0 unter Einleiten von Stickstoff so lange erhitzt, bis die Umesterung beendet ist. Anschließend wird 1 Stunde lang im Vakuum bei 140° C gehalten.Example 1 Production of the polycondensation product used In one with thermometer, stirrer and water separator with attached reflux condenser equipped four-necked flask are 144 parts by weight of maleic acid dimethyl ester, _ _182 parts by weight of triethyl phosphate, 124 parts by weight of ethylene glycol and 74 parts by weight Butanol in the presence of 1 part by weight of Ca0 while passing in nitrogen for so long heated until the transesterification is complete. Then 1 hour in vacuo held at 140 ° C.
70 Gewichtsteile des so erhaltenen Polykondensationsproduktes werden erfindungsgemäß mit 30 Gewichtsteilen Styrol vermischt und bis zur Homogenität verrührt. Nach Zusatz von 0,5 % Benzoylperoxyd härtet die Lösung bei 90° C innerhalb kurzer Zeit zu einem festen Produkt aus, das sich nicht mehr in organischen Lösungsmitteln löst und in einer Flamme nur schwer brennt, außerhalb der Flamme sogleich verlöscht. Beispiel 2 Herstellung des verwendeten Polykondensationsproduktes In einem 500-cm3-Vierhalskolben, der mit Rührer, Thermometer, Wasserabscheider und Stickstoffeinleitungsrohr versehen ist, werden 98 Gewichtsteile Maleinsäureanhydrid mit 83 Gewichtsteilen Äthylenglykol verestert. Nach der Abtrennung des Wassers, zuletzt bei etwa 200° C, wird 1 Stunde lang im Vakuum erhitzt, um die letzten Wasserreste zu entfernen. Danach läßt man abkühlen, löst das Reaktionsprodukt in 150 cm3 Dioxan und gibt 20 Gewichtsteile Butanol zu. Darauf werden 51 Gewichtsteile Phosphoroxychlorid mittels eines Tropftrichters langsam eintropfen gelassen. Nach Beendigung der Zugabe destilliert man das Dioxan allmählich ab, während gleichzeitig Stickstoff durch das Reaktionsgemisch perlt. Schließlich gibt man nochmals 150 cm3 Dioxan zu und destilliert es in der gleichen Weise wieder ab. Die letzten Anteile Dioxan werden im Vakuum entfernt. 80 Gewichtsteile des so erhaltenen Polykondensationsproduktes werden erfindungsgemäß mit 20 Gewichtsteilen Vinylacetat homogen vermischt und mit 1% Benzoylperoxyd versetzt. Bei 100° C erhält man schnell daraus harte, unlösliche Gießlinge, die praktisch nicht brennen.70 parts by weight of the polycondensation product thus obtained mixed according to the invention with 30 parts by weight of styrene and stirred until homogeneous. After adding 0.5% benzoyl peroxide, the solution hardens within a short time at 90 ° C Time to become a solid product that is no longer in organic solvents dissolves and burns only with difficulty in a flame, immediately extinguishes outside the flame. Example 2 Production of the polycondensation product used In a 500 cm3 four-necked flask, which is equipped with a stirrer, thermometer, water separator and nitrogen inlet tube is 98 parts by weight of maleic anhydride with 83 parts by weight of ethylene glycol esterified. After the water has been separated off, last at about 200 ° C., it is 1 hour Heated for a long time in a vacuum to remove the last remaining water. Then you let cool, dissolve the reaction product in 150 cm3 of dioxane and add 20 parts by weight Butanol too. 51 parts by weight of phosphorus oxychloride are then added using a dropping funnel allowed to drip in slowly. After the addition has ended, the dioxane is distilled off gradually off, while nitrogen bubbles through the reaction mixture at the same time. Finally, another 150 cm3 of dioxane are added and it is distilled in the same Reject again. The last portions of dioxane are removed in vacuo. 80 parts by weight of the polycondensation product thus obtained are, according to the invention, with 20 parts by weight Vinyl acetate mixed homogeneously and mixed with 1% benzoyl peroxide. Maintains at 100 ° C hard, insoluble castings, which practically do not burn, are quickly made from them.
Beispiel 3 70 Gewichtsteile des gleichen Polykondensationsproduktes wie im Beispiel 2 werden mit 30 Gewichtsteilen Diallylphthalat vermischt. Nach Zusatz von 1 Gewichtsteil Benzoylperoxyd erhält man schnell bei 80° C ein hartes, unlösliches Produkt.Example 3 70 parts by weight of the same polycondensation product as in Example 2 are mixed with 30 parts by weight of diallyl phthalate. After addition 1 part by weight of benzoyl peroxide quickly becomes a hard, insoluble one at 80 ° C Product.
Beispiel 4 70 Gewichtsteile des gleichen Polykondensationsproduktes wie im Beispiel 2 werden mit 30 Gewichtsteilen Phenylphosphonsäurediallyiester vermischt und unter Zusatz von 1 Gewichtsteil Benzoylperoxyd bei 80° C in ein unlösliches, praktisch unbrennbares Produkt übergeführt. _Example 4 70 parts by weight of the same polycondensation product as in Example 2 are mixed with 30 parts by weight of phenylphosphonic diallyiester and with the addition of 1 part by weight of benzoyl peroxide at 80 ° C in an insoluble, practically incombustible product transferred. _
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22227A DE1044398B (en) | 1957-01-26 | 1957-01-26 | Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products with shaping |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22227A DE1044398B (en) | 1957-01-26 | 1957-01-26 | Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products with shaping |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1044398B true DE1044398B (en) | 1958-11-20 |
Family
ID=7090362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF22227A Pending DE1044398B (en) | 1957-01-26 | 1957-01-26 | Process for the production of polymeric phosphorus-containing composite polymers based on unsaturated phosphorus-containing polycondensation products with shaping |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1044398B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1110411B (en) * | 1959-05-02 | 1961-07-06 | Hoechst Ag | Process for the production of hardened phosphorus-containing composite polymers |
-
1957
- 1957-01-26 DE DEF22227A patent/DE1044398B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1110411B (en) * | 1959-05-02 | 1961-07-06 | Hoechst Ag | Process for the production of hardened phosphorus-containing composite polymers |
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