DE1098709B - Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds - Google Patents
Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compoundsInfo
- Publication number
- DE1098709B DE1098709B DE1958F0027044 DEF0027044A DE1098709B DE 1098709 B DE1098709 B DE 1098709B DE 1958F0027044 DE1958F0027044 DE 1958F0027044 DE F0027044 A DEF0027044 A DE F0027044A DE 1098709 B DE1098709 B DE 1098709B
- Authority
- DE
- Germany
- Prior art keywords
- polyester resins
- mixtures
- phosphorus
- peroxide
- allyl compounds
- 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
- 239000000203 mixture Substances 0.000 title claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 7
- 239000011574 phosphorus Substances 0.000 title claims description 7
- 150000002978 peroxides Chemical class 0.000 title claims description 6
- 229920002554 vinyl polymer Polymers 0.000 title claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 title claims description 5
- 229920006337 unsaturated polyester resin Polymers 0.000 title description 5
- 229920001225 polyester resin Polymers 0.000 claims description 9
- 239000004645 polyester resin Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000001133 acceleration Effects 0.000 claims 1
- 239000011152 fibreglass Substances 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920006305 unsaturated polyester Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 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
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 2
- -1 vinyl compound Chemical class 0.000 description 2
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- JEQBFCJBVVFPGT-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C=CC=C2)C2=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C=CC=C2)C2=C1 JEQBFCJBVVFPGT-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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
Gegenstand des deutschen Patentes 1 061 065 ist ein Verfahren zur Beschleunigung der peroxydisch bewirkten Härtung von Mischungen aus ungesättigten, Reste von phosphorhaltigen Säuren aufweisenden Polyestern mit daran anpolymerisierbären monomeren Vinylverbindüngen, wonach als Beschleuniger 0,001 bis 10% einer Verbindung der allgemeinen FormelThe subject of the German patent 1,061,065 is a process for accelerating the peroxidically effected Curing of mixtures of unsaturated polyesters containing residues of phosphoric acids with monomeric vinyl compounds that can be polymerized onto it, after which 0.001 to 10% of a compound of the general formula as an accelerator
R(N = C = O)2;R (N = C = O) 2 ;
verwendet wird, wobei χ eine ganze Zahl von 1 bis 4 und R einen gegebenenfalls noch durch andere mit Isocyanaten nicht reagierende Gruppen substituierten ein- oder mehrwertigen Alkyl-, Alkylen-, Aryl-, Aralkyl-, Alkylaryl-, Cycloalkyl- oder heterocyclischen Rest bedeutet. is used, where χ is an integer from 1 to 4 and R is a mono- or polyvalent alkyl, alkylene, aryl, aralkyl, alkylaryl, cycloalkyl or heterocyclic radical which is optionally substituted by other groups which do not react with isocyanates .
Es wurde nun gefunden, daß auch die peroxydisch bewirkte Härtung von Mischungen aus handelsüblichen phosphorfreien ungesättigten Polyesterharzen und monomeren phosphorhaltigen Vinyl- und Allylverbindungen, z. B. Triallylphosphit, Trimethallylphosphit oder Trimethallylphosphat, durch Zugabe von 0,001 bis 10% einer Verbindung der allgemeinen FormelIt has now been found that the peroxide-induced curing of mixtures of commercially available phosphorus-free unsaturated polyester resins and monomeric phosphorus-containing vinyl and allyl compounds, z. B. triallyl phosphite, trimethallyl phosphite or trimethallyl phosphate, by adding from 0.001 to 10% of a compound of the general formula
R . (N = C = O)x R. (N = C = O) x
wesentlich beschleunigt werden kann.can be accelerated significantly.
In der allgemeinen Formel bedeutet χ eine ganze Zahl von 1 bis 4 und R einen gegebenenfalls noch durch andere mit Isocyanaten nicht reagierende Gruppen substituierten ein- oder mehrwertigen Alkyl-, Alkylen-, Aryl-, Aralkyl-, Alkylaryl-, Cycloalkyl- oder heterocyclischen Rest.In the general formula, χ denotes an integer from 1 to 4 and R denotes a mono- or polyvalent alkyl, alkylene, aryl, aralkyl, alkylaryl, cycloalkyl or heterocyclic radical which is optionally substituted by other groups which do not react with isocyanates .
Die handelsüblichen ungesättigten Polyesterharzmassen sind Mischungen aus ungesättigten Polyestern, wie sie beispielsweise durch Kondensation von a,/?-ungesättigten mehrbasischen Carbonsäuren, vorzugsweise ungesättigten Dicarbonsäuren, wie Maleinsäure, Fumarsäure oder Itaconsäure, wobei ein Teil der ungesättigten Säuren durch gesättigte Säuren, z. B. Adipinsäure oder Phthalsäure, ersetzt sein kann, mit mehrwertigen Alkoholen, vorzugsweise Glykolen, wie Äthylenglykol und Diäthylenglykol, erhalten sind, und daran anpolymerisierbären Vinylverbindungen, z. B. Styrol.The commercially available unsaturated polyester resin compositions are mixtures of unsaturated polyesters like them for example by condensation of a, /? - unsaturated polybasic carboxylic acids, preferably unsaturated dicarboxylic acids, such as maleic acid, fumaric acid or Itaconic acid, some of the unsaturated acids being replaced by saturated acids, e.g. B. adipic acid or phthalic acid, can be replaced with polyhydric alcohols, preferably glycols, such as ethylene glycol and diethylene glycol, are obtained and thereon anpolymerisierbären vinyl compounds, e.g. B. styrene.
Das erfindungsgemäße Verfahren zur Härtung von Massen, die neben handelsüblichen Polyesterharzen im allgemeinen 0,1 bis 30% einer phosphorhaltigen monomeren Vinylverbindung enthalten, ist technisch deswegen von erheblicher Bedeutung, weil bei diesen Massen die sonst zur Beschleunigung der Härtung von Polyesterharzen eingesetzten üblichen Beschleunigungsmittel, z.B. Kobaltnaphthenat und Dimethalanilin, im allgemeinen versagen.The process according to the invention for curing masses which, in addition to commercially available polyester resins, im generally contain 0.1 to 30% of a phosphorus-containing monomeric vinyl compound, is therefore technical of considerable importance because with these masses the otherwise accelerated hardening of polyester resins common accelerating agents used, e.g., cobalt naphthenate and dimethalaniline, in general fail.
Selbstverständlich lassen sich auch Mischungen aus ungesättigten Polyestern und daran anpolymerisierbären phosphorhaltigen monomeren Vinyl- und Allylverbindungen erfindungsgemäß härten.Mixtures of unsaturated polyesters and polymerizable onto them can of course also be used Cure phosphorus-containing monomeric vinyl and allyl compounds according to the invention.
Verfahren zur Beschleunigung
der peroxydisch bewirkten Härtung
von Mischungen aus ungesättigten
Polyesterharzen und phosphorhaltigen
monomeren Vinyl- und Allylverbindungen Procedure to speed up
the peroxide-induced hardening
of mixtures of unsaturated
Polyester resins and phosphorus-containing
monomeric vinyl and allyl compounds
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Heinz Schmidt, Frankfurt/M.,
ist als Erfinder genannt wordenDr. Heinz Schmidt, Frankfurt / M.,
has been named as the inventor
Als Beschleuniger seien beispielsweise genannt: Monoisocyanate, wie Octadecylisocyanat, n-Dodecylisocyanat,Examples of accelerators that may be mentioned are: monoisocyanates, such as octadecyl isocyanate, n-dodecyl isocyanate,
Cyclohexylisocyanat, Phenylisocyanat, Polyisocyanate, wie Hexamethylendiisocyanat, Naphthylendiisocyanat, Toluylendiisocyanat oder Naphthalintriisocyanat.Cyclohexyl isocyanate, phenyl isocyanate, polyisocyanates such as hexamethylene diisocyanate, naphthylene diisocyanate, Tolylene diisocyanate or naphthalene triisocyanate.
Zusammen mit Peroxyd-Katalysatoren, wie z. B. Dialkyl-, Diaryl-, Arylalkyl-, Acylperoxyden, vorzugsweise Hydroperoxyden, Persäuren und Perestern, bewirken die Substanzen der von der angeführten Formel umfaßten Verbindungsklasse eine schnellere und auch vorteilhaftere Härtung der Polyesterharze. So werden von den nach diesem Verfahren ausgehärteten Polyesterharzen bessere mechanische Werte und bessere Werte für die Wasseraufnahme erreicht, als wenn die genannten Peroxyde allein eingesetzt werden.Together with peroxide catalysts, such as. B. dialkyl, diaryl, arylalkyl, acyl peroxides, preferably Hydroperoxides, peracids and peresters cause the substances of the formula given included a class of compounds a faster and also more advantageous curing of the polyester resins. Be like that better mechanical values and better values of the polyester resins cured by this process for water absorption than when the peroxides mentioned are used alone.
Durch Variation des Beschleunigerzusatzes in Art und Menge und des Aktivators sowie der Temperatur könnenBy varying the type and amount of accelerator added and the activator and temperature, you can
die Gelier- und Härtungszeiten der ungesättigten Polyesterharze in geeigneter Weise gesteuert werden.the gelation and hardening times of the unsaturated polyester resins can be controlled in a suitable manner.
Die gemäß der Erfindung mit Mono- und/oder Polyisocyanaten als Beschleuniger versetzten ungesättigten Polyesterharzmassen können Verwendung finden alsThe unsaturated compounds mixed with mono- and / or polyisocyanates as accelerators according to the invention Polyester resin compositions can be used as
Gießharze, Überzugsmassen, Lacke, Dispersionen und Klebemittel. Füllmittel, wie Siliciumdioxyd, Farbstoffe, Pigmente, Plastifizierungsmittel oder Armierungsmittel (z. B. Glasfasern) können vor der Härtung zugesetzt werden.Casting resins, coating compounds, lacquers, dispersions and adhesives. Fillers such as silicon dioxide, dyes, Pigments, plasticizers or reinforcing agents (e.g. glass fibers) can be added before curing will.
109 508/412109 508/412
Nach dem erfrndungsgemäßen Verfahren lassen sich auch, wenn ein gewisser Mindestzusatz an phosphorhaltigen monomeren Vinylverbindungen nicht unterschritten wird, auf der Basis von handelsüblichen, normalen und damit leicht und wirtschaftlich zugänglichen Polyesterharzen Massen herstellen, die durch schnelle Härtbaxkeit und im gehärteten Zustand durch Unbrennbarkeit bzw. durch einen Selbstlöscheffekt ausgezeichnet sind.According to the method according to the invention even if a certain minimum addition of phosphorus-containing monomeric vinyl compounds is not fallen below is based on commercially available, normal and thus easily and economically accessible Produce polyester resins masses, which through rapid hardening and in the hardened state Are incombustible or are characterized by a self-extinguishing effect.
20 g einer handelsüblichen Polyesterharzmasse, die aus 70 Gewichtsteilen eines ungesättigten Polyesters und 30 Gewichtsteilen Styrol besteht, wurden mit 2 % Methyläthylketonperoxydlösung (400/(,ig in Dimethylphthalat) und 2 °/0 Octadecylisocyanat versetzt. Zu dieser Mischung wurden5 0/0Phosphorigsäuretriallylester (Triallylphosphit) zugesetzt. Die Masse gelierte nach 21 Minuten bei Raumtemperatur.20 g of a commercial polyester resin composition consisting of an unsaturated polyester and 30 parts by weight of styrene of 70 weight parts, were mixed with 2% Methyläthylketonperoxydlösung (40 0 / (, ig added in dimethyl phthalate) and 2 ° / 0 octadecyl isocyanate. To this mixture wurden5 0/0 Phosphorigsäuretriallylester (Triallyl phosphite) was added The mass gelled after 21 minutes at room temperature.
Die im Beispiel angegebenen Prozentzahlen sind Gewichtsprozente und beziehen sich auf die Gesamtmenge an Polyesterharzmasse.The percentages given in the example are percentages by weight and relate to the total amount on polyester resin compound.
Claims (1)
Deutsche Patentschriften Nr. 889 666,925 499,956 720,Considered publications:
German patent specifications No. 889 666,925 499,956 720,
Morgan, »Glass Reinforced Plastics«, London, 1954,951 729; U.S. Patent No. 2,503,209;
Morgan, Glass Reinforced Plastics, London, 1954,
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1958F0027044 DE1098709B (en) | 1958-08-20 | 1958-08-20 | Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1958F0027044 DE1098709B (en) | 1958-08-20 | 1958-08-20 | Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1098709B true DE1098709B (en) | 1961-02-02 |
Family
ID=600018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1958F0027044 Pending DE1098709B (en) | 1958-08-20 | 1958-08-20 | Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1098709B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2503209A (en) * | 1948-01-30 | 1950-04-04 | American Cyanamid Co | Unsaturated alkyd reacted with unsaturated isocyanate |
| DE889666C (en) * | 1950-05-27 | 1953-09-14 | Bayer Ag | Process for the production of paint raw materials |
| DE925499C (en) * | 1952-10-14 | 1955-03-24 | Bayer Ag | Process for the production of copolymers |
| DE951729C (en) * | 1952-10-11 | 1956-10-31 | Bayer Ag | Suitable solutions for the production of coatings, varnishes and bonds |
| DE956720C (en) * | 1952-10-11 | 1957-01-24 | Bayer Ag | Process for the production of molded articles, including those made from foams, from polyoxy compounds and polyisocyanates |
-
1958
- 1958-08-20 DE DE1958F0027044 patent/DE1098709B/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2503209A (en) * | 1948-01-30 | 1950-04-04 | American Cyanamid Co | Unsaturated alkyd reacted with unsaturated isocyanate |
| DE889666C (en) * | 1950-05-27 | 1953-09-14 | Bayer Ag | Process for the production of paint raw materials |
| DE951729C (en) * | 1952-10-11 | 1956-10-31 | Bayer Ag | Suitable solutions for the production of coatings, varnishes and bonds |
| DE956720C (en) * | 1952-10-11 | 1957-01-24 | Bayer Ag | Process for the production of molded articles, including those made from foams, from polyoxy compounds and polyisocyanates |
| DE925499C (en) * | 1952-10-14 | 1955-03-24 | Bayer Ag | Process for the production of copolymers |
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