DE1054703B - Process for the production of alkali and solvent-resistant plastics based on epoxy resin - Google Patents
Process for the production of alkali and solvent-resistant plastics based on epoxy resinInfo
- Publication number
- DE1054703B DE1054703B DEB32888A DEB0032888A DE1054703B DE 1054703 B DE1054703 B DE 1054703B DE B32888 A DEB32888 A DE B32888A DE B0032888 A DEB0032888 A DE B0032888A DE 1054703 B DE1054703 B DE 1054703B
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- parts
- alkali
- solvent
- production
- 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 6
- 239000003822 epoxy resin Substances 0.000 title claims description 5
- 229920000647 polyepoxide Polymers 0.000 title claims description 5
- 239000003513 alkali Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000004033 plastic Substances 0.000 title claims description 4
- 229920003023 plastic Polymers 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910002804 graphite Inorganic materials 0.000 claims description 7
- 239000010439 graphite Substances 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000003245 coal Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- -1 monomeric Substances 0.000 claims description 3
- 239000002685 polymerization catalyst Substances 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 2
- 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 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- 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
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Description
Gegenstand des Patents 970 975 ist ein Verfahren zur Herstellung von alkali- und lösungsmittelbeständigen Kunststoffen auf Epoxyharzgrundlage durch Härten eines Gemisches aus einem wärmehärtbaren Epoxyharz, monomeren, epoxydgruppenfreien, polymerisierbaren Verbindungen mit einer reaktionsfähigen Doppelbindung, einer mehrbasischen, nicht polymerisierbaren Carbonsäure oder deren Anhydrid in einer wenigstens 20%), bezogen auf das Gemisch, betragenden Menge und gegebenenfalls Polymerisationskatalysatoren in der Wärme unter Formgebung.The subject of patent 970 975 is a process for the production of alkali and solvent-resistant Epoxy resin-based plastics by curing a mixture of a thermosetting Epoxy resin, monomeric, epoxy group-free, polymerizable compounds with a reactive Double bond, a polybasic, non-polymerizable carboxylic acid or its anhydride in an amount of at least 20%, based on the mixture, and optionally polymerization catalysts in the warmth under shaping.
Es wurde nun gefunden, daß sich mechanisch sehr feste Formkörper mit großer Korrosionsbeständigkeit gegen heiße organische Lösungsmittel, Salzlösungen, Säuren und Laugen herstellen lassen, wenn härtbare Mischungen gemäß Hauptpatent verwendet werden, die zusätzlich Graphit oder zerkleinerte Kohle enthalten. It has now been found that mechanically very strong moldings with high corrosion resistance Can be prepared against hot organic solvents, salt solutions, acids and alkalis, if curable Mixtures according to the main patent are used, which additionally contain graphite or crushed coal.
Es ist besonders vorteilhaft, etwa 30' bis 75% Graphit, bezogen auf die Mischung der härtbaren Bestandteile, zu verwenden, doch kann auch ein Zusatz von 100% Graphit und mehr günstig sein. Auch insbesondere feingemahlene Kohle, wie Hartbrandkohle. Koks oder aufbereitete Kohle, kann von Vorteil sein. Die verwendeten wärmehärtbaren Kunstharze sind z. B. die Umsetzungsprodukte von Phenolen, z. B. von p.p'-Dioxydiphenylpropan mit Epichlorhydrin, die naah bekannten Verfahren durch Erwärmen der Ausgangsverbindungen in Gegenwart von Basen erhalten werden, ferner Glycidyläther ein- oder mehrwertiger Alkohole, z. B. des Glycerins, ButandioIs oder Butantriols. Auch Gemische dieser Verbindungen können verwendet werden. Geeignete ungesättigte, polymerisierbare Verbindungen sind beispielsweise monomere Vinylverbindungen, besonders ungesättigte Kohlenwasserstoffe, z. B. Styrol oder substituierte Styrole, ferner Ester ungesättigter Alkohole oder ungesättigter Säuren, die keine Epoxydgruppen enthalten, z. B. Diallylphthalat oder Acrylsäureester. Zur Gruppe der mehrbasischen gesättigten Carbonsäuren oder ihrer Anhydride gehört z. B. Phthalsäureanhydrid. Es können außerdem die Härtung beschleunigende Verbindungen, z. B. Dicyandiamid, zusammen mit den Carbonsäuren verwendet werden.It is particularly advantageous to use about 30 'to 75% graphite, based on the mixture of the hardenable Ingredients to use, but an addition of 100% graphite and more can also be beneficial. Even especially finely ground coal, such as hard coal. Coke, or processed coal, can be beneficial be. The thermosetting resins used are e.g. B. the reaction products of phenols, z. B. of p.p'-dioxydiphenylpropane with epichlorohydrin, the well-known method by heating the starting compounds are obtained in the presence of bases, also glycidyl ether or polyhydric alcohols, e.g. B. of glycerine, butanediol or butanetriol. Also mixtures of these compounds can be used. Suitable unsaturated, polymerizable compounds are, for example monomeric vinyl compounds, especially unsaturated hydrocarbons, e.g. B. styrene or substituted Styrenes, also esters of unsaturated alcohols or unsaturated acids that do not contain epoxy groups, z. B. diallyl phthalate or acrylic acid ester. To the group of polybasic saturated carboxylic acids or its anhydride belongs to e.g. B. phthalic anhydride. It can also accelerate the hardening process Connections, e.g. B. dicyandiamide, can be used together with the carboxylic acids.
Die Komponenten werden zweckmäßig in der Wärme homogenisiert und mit Graphit oder Kohle
vermischt. Man gießt die Mischungen zweckmäßig in Formen und härtet in bekannter Weise bei Temperaturen
zwischen etwa 90 und 220° C Vorteilhaft fügt man Katalysatoren und Beschleuniger zu. Als Polymerisationskatalysatoren
können Peroxyde, z. B. Cyclohexanonperoxyd. Benzoylperoxyd oder Di-tert.-butylperoxyd,
dienen. Gegebenenfalls können sie in Verbindung mit Beschleunigern, wie Kobalt- oder
Verfahren zur Herstellung
von alkali- und lösungsmittelbeständigen Kunststoffen auf EpoxyharzgrundlageThe components are expediently homogenized in the heat and mixed with graphite or carbon. The mixtures are expediently poured into molds and cured in a known manner at temperatures between about 90 and 220 ° C. It is advantageous to add catalysts and accelerators. As polymerization catalysts, peroxides, e.g. B. cyclohexanone peroxide. Benzoyl peroxide or di-tert-butyl peroxide, serve. Optionally, they can be used in conjunction with accelerators, such as cobalt or manufacturing processes
of alkali and solvent-resistant plastics based on epoxy resin
Anmelder:Applicant:
Badische Anihn- & Soda-Fabrik
Aktiengesellschaft,
Ludwigshafen/RheinBadische Anihn- & Soda-Fabrik
Corporation,
Ludwigshafen / Rhine
Dr. Werner Kunzer, Ludwigshafen/Rhein, und Dr. Ferdinand Meyer, Mannheim, sind als Erfinder genannt wordenDr. Werner Kunzer, Ludwigshafen / Rhine, and Dr. Ferdinand Meyer, Mannheim, have been named as inventors
Bleinaphthenat, verwendet werden. Zur Verbesserung der mechanischen Eigenschaften, insbesondere der Schlagfestigkeit, lassen sich die Formkörper mit Geweben, z. B. mit Textil- oder Glasfasergeweben, oder mit Metallstützen versteifen.Lead naphthenate can be used. To improve the mechanical properties, especially the Impact resistance, the moldings can be made with fabrics such. B. with textile or fiberglass fabrics, or stiffen with metal supports.
Die neuen Formkörper haften sehr fest an den verschiedensten Werkstoffen, z. B. an Metallen. Sie eignen sich hervorragend für den Bau von Apparaten und Apparateteilen besonders in der chemischen und verwandten Industrie, die korrodierenden Einflüssen ausgesetzt sind. Sie sind außerordentlich beständig gegen Säuren, Laugen, Salzlösungen und organische Lösungsmittel und besitzen eine große mechanische Festigkeit.The new moldings adhere very firmly to a wide variety of materials, e.g. B. on metals. she are ideal for the construction of apparatuses and apparatus parts especially in the chemical and related industries that are exposed to corrosive influences. They are extremely stable against acids, alkalis, salt solutions and organic solvents and have a great mechanical Strength.
15 Teile eines Polyglyeidyläthers aus p,p'-Dioxydiphenylpropan und Epichlorhydrin mit dem Epoxydwert 0,1 bis 0,4 (der Epoxydwert gibt an, wieviel Äquivalente Epoxydgruppen in 100 g Glycidylpolyärher enthalten sind) werden mit 15 Teilen Styrol, 4,5 Teilen Phthalsäureanhydrid und 65 Teilen Graphit gemischt. Man fügt 0,5 Teile Cyclohexanonperoxyd zu, gießt in Formen und härtet bei Temperaturen über 100° C15 parts of a polyglyeidyl ether made from p, p'-dioxydiphenylpropane and epichlorohydrin with the epoxy value 0.1 to 0.4 (the epoxy value indicates how many equivalents of epoxy groups in 100 g of glycidyl polyether are contained) with 15 parts of styrene, 4.5 parts of phthalic anhydride and 65 parts of graphite mixed. 0.5 part of cyclohexanone peroxide is added, poured into molds and cured at temperatures over 100 ° C
Man vermischt 20 Teile eines Glycidylpolyäthers aus Glycerin und Epichlorhydrin mit dem Epoxyd-Mix 20 parts of a glycidyl polyether made from glycerine and epichlorohydrin with the epoxy
809 789/521809 789/521
Claims (1)
Deutsche Patentschrift Nr. 906 998.Considered publications:
German patent specification No. 906 998.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB32888A DE1054703B (en) | 1954-10-06 | 1954-10-06 | Process for the production of alkali and solvent-resistant plastics based on epoxy resin |
| FR1131761D FR1131761A (en) | 1954-10-06 | 1955-09-30 | Mixtures of hardenable casting resins for obtaining plastics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB32888A DE1054703B (en) | 1954-10-06 | 1954-10-06 | Process for the production of alkali and solvent-resistant plastics based on epoxy resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1054703B true DE1054703B (en) | 1959-04-09 |
Family
ID=6963876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB32888A Pending DE1054703B (en) | 1954-10-06 | 1954-10-06 | Process for the production of alkali and solvent-resistant plastics based on epoxy resin |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1054703B (en) |
| FR (1) | FR1131761A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1184953B (en) * | 1960-07-22 | 1965-01-07 | Henkel & Cie Gmbh | Improvement of the flow properties of highly filled polyester molding compounds |
| US3385802A (en) * | 1964-07-30 | 1968-05-28 | United States Steel Corp | Foamed polyester coatings containing coal as filler |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1068889B (en) * | 1959-11-12 | |||
| DE1130166B (en) * | 1959-08-25 | 1962-05-24 | Licentia Gmbh | Process for the production of cast resin bodies by curing polyepoxides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE906998C (en) * | 1948-03-29 | 1954-03-18 | Bataafsche Petroleum | Compositions hardenable to resinous products and processes for their manufacture |
-
1954
- 1954-10-06 DE DEB32888A patent/DE1054703B/en active Pending
-
1955
- 1955-09-30 FR FR1131761D patent/FR1131761A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE906998C (en) * | 1948-03-29 | 1954-03-18 | Bataafsche Petroleum | Compositions hardenable to resinous products and processes for their manufacture |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1184953B (en) * | 1960-07-22 | 1965-01-07 | Henkel & Cie Gmbh | Improvement of the flow properties of highly filled polyester molding compounds |
| US3385802A (en) * | 1964-07-30 | 1968-05-28 | United States Steel Corp | Foamed polyester coatings containing coal as filler |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1131761A (en) | 1957-02-27 |
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