DE1016935B - Process for the polymerization of organic compounds - Google Patents
Process for the polymerization of organic compoundsInfo
- Publication number
- DE1016935B DE1016935B DED19859A DED0019859A DE1016935B DE 1016935 B DE1016935 B DE 1016935B DE D19859 A DED19859 A DE D19859A DE D0019859 A DED0019859 A DE D0019859A DE 1016935 B DE1016935 B DE 1016935B
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- carried out
- compounds
- small amounts
- polymerized
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 12
- 150000002894 organic compounds Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 claims description 5
- -1 compound Betaine derivatives Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002443 hydroxylamines Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000005609 naphthenate group Chemical group 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002978 peroxides Chemical group 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 230000003678 scratch resistant effect Effects 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
- BOOBDAVNHSOIDB-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC(C(=O)OOC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl BOOBDAVNHSOIDB-UHFFFAOYSA-N 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 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
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
Description
Verfahren zur Polymerisation organischer Verbindungen Es ist bekannt, organische Verbindungen mit endständigen oder mittelständigen Doppelbindungen zwischen zwei Kohlenstoffatomen zu polymerisieren. Als solche Verbindungen kommen beispielsweise Styrol oder seine Derivate, Acrylsäure und Methacrylsäure oder ihre Ester, Vinylverbindungen, Acrylnitril, Butadien, Chlorbutadien, Dimethylbutadien, für sich oder in Gemischen miteinander, in Betracht. Die Polymerisation dieser Verbindungen kann in Lösung oder Emulsion oder im Block durchgeführt werden. Für viele Zwecke kann mit Vorteil ein System polymerisiert werden, das aus einer Lösung oder Suspension eines hochmolekularen Stoffes in einem polymerisierbaren monomeren Stoff besteht. Derartige Mischungen können z. B. mit gutem Erfolge für Dentalzwecke verwendet werden.Process for the polymerization of organic compounds It is known organic compounds with terminal or central double bonds between polymerize two carbon atoms. Examples of such compounds are Styrene or its derivatives, acrylic acid and methacrylic acid or their esters, vinyl compounds, Acrylonitrile, butadiene, chlorobutadiene, dimethylbutadiene, alone or in mixtures with each other, into consideration. The polymerization of these compounds can take place in solution or emulsion or in block. Can be beneficial for many purposes a system that consists of a solution or suspension of a high molecular weight The substance consists of a polymerizable monomeric substance. Such mixtures can e.g. B. be used with good results for dental purposes.
Für die Polymerisation derartiger Stoffe oder Stoffgemische sind schon verschiedene Katalysatoren, insbesondere Redox-Systeme, vorgeschlagen worden.For the polymerization of such substances or mixtures of substances are already various catalysts, particularly redox systems, have been proposed.
Es wurde nun gefunden, daß als Katalysatoren hierfür mit ausgezeichnetem Erfolg Systeme verwendet werden können, die einerseits mindestens ein Umsetzungsprodukt eines a-Oxysulfons mit einem primären Amin oder Ammoniak, andererseits solche quaternäre Verbindungen enthalten, die die Bromphenolblaureaktion geben. Ausgeschlossen sind die Betainderivate der allgemeinen Formel fR,N # (CH,)." - CO OR]+Cl- und Hydroxylaminderivate der allgemeinen Formel rR, N # O R]+ Cl-. R bedeutet aliphatische, aromatische, hydroaromatische oder heterocyclische Reste.It has now been found that the catalysts used for this purpose with excellent success are systems which, on the one hand, contain at least one reaction product of an α-oxysulfone with a primary amine or ammonia and, on the other hand, contain quaternary compounds which give the bromophenol blue reaction. The betaine derivatives of the general formula fR, N # (CH,). "- CO OR] + Cl- and hydroxylamine derivatives of the general formula rR, N # OR] + Cl-. R denotes aliphatic, aromatic, hydroaromatic or heterocyclic radicals.
a-Oxysulfone haben die allgemeine Formel R'- S02-R"-OH.α-Oxysulfones have the general formula R'-S02-R "-OH.
Hierbei bedeutet R' einen aliphatischen, aromatischen, hydroaromatischen oder heterocyclischen Rest, R" vorzugsweise einen aliphatischen Rest mit zwei freien Valenzen. Bei der Umsetzung derartiger a-Oxysulfone mit Ammoniak oder primären Aminen entstehen Verbindungen der allgemeinen Formeln wobei R"' einen aliphatischen, aromatischen, hydroaromatischen oder heterocyclischen Rest bedeutet.Here, R 'denotes an aliphatic, aromatic, hydroaromatic or heterocyclic radical, and R "preferably denotes an aliphatic radical with two free valences. The reaction of such α-oxysulfones with ammonia or primary amines gives compounds of the general formulas where R "'denotes an aliphatic, aromatic, hydroaromatic or heterocyclic radical.
In der Zeitschrift »Proc. Soc. Exper. Biol. Med., 81 (1952), S. 105 bis 109« ist ein Verfahren für die Bestimmung vorzugsweise quaternärer Ammoniumverbindungen durch Reaktion mit Bromphenolblau in wäßriger Lösung beschrieben. Von uns durchgeführte weitere Untersuchungen haben ergeben, daß diese Reaktion mit allen Verbindungen stattfindet, die die allgemeinen Formeln haben. In diesem Falle bedeuten R', R", R"' und R"" aliphatische, aromatische, hydroaromatische oder heterocyclische Reste, X einen Säurerest, der vorzugsweise ein Halogen, z. B. Chlor, ist, aber auch ein anderes Säureradikal, z. B. den Schwefelsäurerest, Phosphorsäurerest oder einen Sulfonrest, bedeuten kann.In the magazine “Proc. Soc. Exper. Biol. Med., 81 (1952), pp. 105 to 109 «describes a method for the determination of preferably quaternary ammonium compounds by reaction with bromophenol blue in aqueous solution. Further investigations carried out by us have shown that this reaction takes place with all compounds that correspond to the general formulas to have. In this case, R ', R ", R"' and R "" mean aliphatic, aromatic, hydroaromatic or heterocyclic radicals, X is an acid radical which is preferably a halogen, e.g. B. chlorine, but also another acid radical, e.g. B. the sulfuric acid residue, phosphoric acid residue or a sulfone residue, can mean.
Es wurde gefunden, daß mit besonderem Vorteil solche die Bromphenolblaureaktion gebende Verbindungen verwendet werden können, die in der zu polymerisierenden Verbindung in den verwendeten Mengen löslich sind. Ausgenommen sind Betainderivate der allgemeinen Formel [R@N . (CH,), . COOR]+Cl- und Hydroxylaminderivate der allgemeinen Formel [R3 N . O R] + Cl-.It has been found that the bromophenol blue reaction is particularly advantageous giving compounds used can be that in the to be polymerized Compound are soluble in the amounts used. Betaine derivatives are excluded of the general formula [R @ N. (CH,),. COOR] + Cl- and hydroxylamine derivatives of the general Formula [R3 N. O R] + Cl-.
Die Polymerisation kann mit gutem Erfolge in Gegenwart von Sauerstoff durchgeführt werden. Zweckmäßig wird der Sauerstoff in peroxydischer Form, z. B. als Wasserstoffperoxyd öder als Dibenzoylperoxyd, verwendet.The polymerization can be carried out with good results in the presence of oxygen be performed. The oxygen is expediently in peroxide form, e.g. B. used as hydrogen peroxide or as dibenzoyl peroxide.
Der Polymerisationsvorgang kann ferner verbessert werden, wenn man geringe Mengen von Schwermetallverbindungen und/oder ein- oder mehrwertige Alkohole zusetzt. Ebenso wirkt die Gegenwart geringer Mengen von Wasser polymerisationsfördernd.The polymerization process can also be improved if small amounts of heavy metal compounds and / or mono- or polyhydric alcohols clogs. The presence of small amounts of water also promotes polymerization.
Die Polymerisation gemäß der Erfindung wird vorteilhaft im Block durchgeführt. Hierbei können die Temperaturen verhältnismäßig niedrig, z. B. auf Zimmertemperatur oder darunter; gehalten werden; in manchen Fällen kann die Polymerisation auch durch Erwärmen beschleunigt werden.The polymerization according to the invention is advantageously carried out in block. The temperatures can be relatively low, e.g. B. at room temperature or below; being held; in some cases the polymerization can also go through Heating can be accelerated.
Mit besonderem Erfolge läßt sich das Verfahren der Erfindung zur Polymerisation von Gemischen anwenden, die aus einer Lösung oder Dispersion mindestens einer polymeren Verbindung in mindestens einer flüssigen monomeren polymerisierbaren Verbindung bestehen.The process of the invention can be used for polymerization with particular success of mixtures that consist of a solution or dispersion of at least one polymeric Compound in at least one liquid monomeric polymerizable compound exist.
Zur Stabilisierung des monomeren Bestandteiles der Ausgangsstoffe hat sich der Zusatz geringer Mengen von Polyesterharzen, z. B. von Umsetzungsprodukten von Maleinsäure oder Fumarsäure mit Diolen, als zweckmäßig erwiesen. Diese Polyesterharze sollen hierbei in dem monomeren Anteil löslich sein.To stabilize the monomeric component of the starting materials the addition of small amounts of polyester resins, e.g. B. of conversion products of maleic acid or fumaric acid with diols, proved to be useful. These polyester resins should be soluble in the monomeric part.
Die erfindungsgemäßen Katalysatorkombinationen sind besonders gut geeignet zur Herstellung von Dentalpräparaten, z. B. für die Herstellung von Prothesen, Dentalfüllungen und für Prothesenreparaturen, aber auch für andere technische Zwecke, z. B. für Spachtelmassen, Klebezwecke oder Reaktionslacke. Sie sind gut brauchbar in Kombination mit monomerem Methacrylat und Methacrylat-Perlpulver. Ihre Anwendung ist jedoch keineswegs nur auf dieses System beschränkt.The catalyst combinations according to the invention are particularly good suitable for the production of dental preparations, e.g. B. for the manufacture of prostheses, Dental fillings and for prosthesis repairs, but also for other technical purposes, z. B. for leveling compounds, adhesive purposes or reactive paints. They are very useful in combination with monomeric methacrylate and methacrylate pearl powder. Your application however, it is by no means restricted to this system only.
Solche Systeme zeichnen sich, soweit sie auf dem Dental-Sektor zur Anwendung gelangen, durch eine besonders rasche Polymerisation aus, durch eine vorzügliche Oberflächenhärte und vollständige Polymerisation auch dünner Schichten. Die hohe Farbbeständigkeit erfüllt auch die von dieser Seite erwachsenen, jetzt hohen Anforderungen. Solche Systeme können außer Füllmittel», Fasermaterial, Glasfasern, auch die üblichen Pigmente enthalten.Such systems stand out as far as they are used in the dental sector Use, through a particularly rapid polymerization, through an excellent Surface hardness and complete polymerisation of even thin layers. The height Color fastness also fulfills the now high requirements that have arisen from this side. In addition to fillers, fiber material, glass fibers, such systems can also include the usual Contain pigments.
Es ist zweckmäßig, bei Zweikomponentenpräparaten für den Dentalsektor das Peroxyd und das Derivat des a-Oxysulfons mit der pulverförmigen Komponente zu mischen und die quaternäre Ammoniumverbindung im Monomeren zu lösen. Dem monomeren Methacrylat können hierbei die üblichen Stabilisatoren zugesetzt werden. Beispiel 1 0,6m1 monomerer Methacrylsäuremethylester, der 0,70/0 Phenyläthyldihexylbenzylammoniumchlorid und 1,70/0 1, 2-Propandiol sowie 10y Kupfer je ml (als Naphthenat) enthält, werden mit 1 g polymerem Methacrylsäuremethylester vermengt, in den 0,80/, eines a-Aminosulfons der Formel (C H3 C0 H4 S O2)2 N H und 0,811/0 Dichlorbenzoylperoxyd eingemischt sind.It is useful for two-component preparations for the dental sector the peroxide and the derivative of a-oxysulfone with the powdery component mix and dissolve the quaternary ammonium compound in the monomer. The monomeric The usual stabilizers can be added to methacrylate. example 1 0.6m1 monomeric methyl methacrylate, the 0.70 / 0 phenylethyldihexylbenzylammonium chloride and 1.70 / 0.1, 2-propanediol and 10y copper per ml (as naphthenate) mixed with 1 g of polymeric methyl methacrylate, in the 0.80 /, of an α-aminosulfone of the formula (C H3 C0 H4 S O2) 2 N H and 0.811 / 0 dichlorobenzoyl peroxide mixed in are.
Die Masse ist in einem Gefäß von 25 mm Durchmesser nach 9 3/4 Minuten erhärtet. Beispiel 2 0,6m1 monomerer Methacrylsäuremethylester, der 0,70/0 Phenyläthyldihexylbenzylammoniumchlorid, 1,7°/0 1, 2-Propandiol und 10y Cu++ je ml (als Naphthenat) enthält, werden mit 1 g polymerem Methacrylsäuremethylester vermengt, in den 0,8"/, Di-(p-tolylsulfonmethyl)-amin und 0,60/, p-Chlorbenzoylperoxyd eingemischt sind.The mass has hardened in a vessel with a diameter of 25 mm after 9 3/4 minutes. Example 2 0.6 ml of monomeric methyl methacrylate containing 0.70 / 0 phenylethyldihexylbenzylammonium chloride, 1.7% / 0 1, 2-propanediol and 10% Cu ++ per ml (as naphthenate) are mixed with 1 g of polymeric methyl methacrylate, in which 0, 8 "/, di- (p-tolylsulfonmethyl) -amine and 0.60 /, p-chlorobenzoyl peroxide are mixed in.
Die Oberflächenaushärtung des nach dem Beispiel 2 erhaltenen Polymerisationsproduktes wurde mit einem Produkt nach dem Stand der Technik aus dem nachstehenden Ansatz verglichen: 0,6 ml monomerer Methacrylsäuremethylester, der 0,150/0 p-Tolyläthyldibutylaminhydrochlorid, 2,50/0 1, 2-Propandiol und 15 y Cu++ je ml (als Naphthenat) enthält, werden mit 1 g polymerem Methacrylsäuremethylester vermengt, in den 0,80/, Di-(p-tolylsulfonmethyl)-amin und 0,60/, p-Chlorbenzoylperoxyd eingemischt sind.The surface hardening of the polymerization product obtained according to Example 2 was compared with a product according to the prior art from the following approach: 0.6 ml of monomeric methyl methacrylate, 0.150 / 0 p-tolylethyldibutylamine hydrochloride, 2.50 / 0 1, 2-propanediol and 15 y Cu ++ per ml (as naphthenate) are mixed with 1 g of polymeric methyl methacrylate into which 0.80 /, di- (p-tolylsulfonmethyl) amine and 0.60 /, p-chlorobenzoyl peroxide are mixed.
Der Zeitpunkt, bei dem der Probekörper beim Klopfen mit einem Kugelinstrument einen klingenden Ton gibt, d. h. der Beginn der Durchhärtung, wird als »klopfhart« bezeichnet.The point in time at which the test specimen was knocked with a ball instrument gives a ringing tone, d. H. the beginning of hardening, is called "knock hard" designated.
Der Zeitpunkt, bei dem sich die Oberfläche des Probekörpers bei mäßig
starkem Druck mit dem Kugelinstrument nicht mehr ritzen läßt, d. h. der Endpunkt
der Durchhärtung, wird als »kratzfest» bezeichnet.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED19859A DE1016935B (en) | 1955-02-22 | 1955-02-22 | Process for the polymerization of organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED19859A DE1016935B (en) | 1955-02-22 | 1955-02-22 | Process for the polymerization of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1016935B true DE1016935B (en) | 1957-10-03 |
Family
ID=7036518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED19859A Pending DE1016935B (en) | 1955-02-22 | 1955-02-22 | Process for the polymerization of organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1016935B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134200B (en) * | 1960-07-13 | 1962-08-02 | Richter & Hoffmann Harvard Den | Process for the preparation of polymerization and copolymerization products |
| DE1301074B (en) * | 1964-06-20 | 1969-08-14 | Resart Ihm Ag | Process for the preparation of polymerization products |
| DE1301516B (en) * | 1966-07-21 | 1969-08-21 | Cassella Farbwerke Mainkur Ag | Process for the production of homo- and co-polymers from olefinically unsaturated monomers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE913477C (en) * | 1950-07-17 | 1954-06-14 | Degussa | Process for the preparation of polymerization products |
| DE916733C (en) * | 1950-07-17 | 1954-08-16 | Degussa | Process for the preparation of polymerization products |
-
1955
- 1955-02-22 DE DED19859A patent/DE1016935B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE913477C (en) * | 1950-07-17 | 1954-06-14 | Degussa | Process for the preparation of polymerization products |
| DE916733C (en) * | 1950-07-17 | 1954-08-16 | Degussa | Process for the preparation of polymerization products |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134200B (en) * | 1960-07-13 | 1962-08-02 | Richter & Hoffmann Harvard Den | Process for the preparation of polymerization and copolymerization products |
| DE1301074B (en) * | 1964-06-20 | 1969-08-14 | Resart Ihm Ag | Process for the preparation of polymerization products |
| DE1301516B (en) * | 1966-07-21 | 1969-08-21 | Cassella Farbwerke Mainkur Ag | Process for the production of homo- and co-polymers from olefinically unsaturated monomers |
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