DE1004381B - Process for the copolymerization of methyl isopropenyl ketone - Google Patents
Process for the copolymerization of methyl isopropenyl ketoneInfo
- Publication number
- DE1004381B DE1004381B DER17585A DER0017585A DE1004381B DE 1004381 B DE1004381 B DE 1004381B DE R17585 A DER17585 A DE R17585A DE R0017585 A DER0017585 A DE R0017585A DE 1004381 B DE1004381 B DE 1004381B
- Authority
- DE
- Germany
- Prior art keywords
- isopropenyl ketone
- methyl isopropenyl
- copolymerization
- methyl
- 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
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 8
- 238000007334 copolymerization reaction Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 1
- WQMWHMMJVJNCAL-UHFFFAOYSA-N 2,4-dimethylpenta-1,4-dien-3-one Chemical compound CC(=C)C(=O)C(C)=C WQMWHMMJVJNCAL-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- -1 Vinyl methyl ketone Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/36—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by a ketonic radical
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
Description
Verfahren zur Mischpolymerisation von Methylisopropenylketon Es ist bereits bekannt, Methylisopropenylketon sowohl für sich allein als auch zusammen mit anderen polymerisierbaren Verbindungen zu polymerisieren, wobei feste Kunststoffe erhalten werden. Bei einem dieser bekannten Verfahren wird 1-Chlor-butadien-1, 3 in Abwesenheit oder in Gegenwart beschränkter Mengen von Sauerstoff für sich allein oder mit polymerisierbaren Stoffen, wie z. B. Methylisopropenylketon, polymerisiert. Die Polymerisation kann in einer inerten Gasphase bei vermindertem, gewöhnlichem oder erhöhtem Druck und in Gegenwart polymerisationsbeschleunigender Mittel, wie z. B. Alkalimetallen oder deren Legieruhgen oder Peroxyde, erfolgen. Durch Zusatz von Verzögerern, wie aromatischen Hydroxylverbindungen oder Aminen, kann die Polymerisation verlangsamt oder bei einem gewünschten Punkt unterbrochen werden. Die Polymerisation der Gemische läßt sich in Lösung oder in Emulsion durchführen. Nach einem anderen Verfahren wird Halogen-2-butadien-(1, 3) in wäßriger Emulsion zusammen mit anderen polymerisierbaren Stoffen in Mengen von 1 bis 501/o polymerisiert. Als polymerisierbare Stoffe werden Acryl-, Methacrylsäureester, Vinylchlorid, ungesättigte Ketone, wie Vinylmethylketon, und Methylisopropenylketon, Styrol sowie Vinylester angewandt.Process for copolymerization of methyl isopropenyl ketone It is already known, methyl isopropenyl ketone both alone and together polymerize with other polymerizable compounds, being solid plastics can be obtained. In one of these known processes, 1-chloro-1,3-butadiene is used in the absence or presence of limited amounts of oxygen on its own or with polymerizable substances, such as. B. methyl isopropenyl ketone polymerized. The polymerization can be carried out in an inert gas phase at reduced, ordinary or increased pressure and in the presence of polymerization accelerating agents, such as z. B. alkali metals or their alloys or peroxides. By addition of retarders, such as aromatic hydroxyl compounds or amines, the polymerization slowed down or paused at a desired point. The polymerization the mixture can be carried out in solution or in emulsion. According to another Process is halogen-2-butadiene- (1, 3) in aqueous emulsion along with others polymerizable substances in amounts of 1 to 501 / o polymerized. As polymerizable Substances are acrylic, methacrylic acid esters, vinyl chloride, unsaturated ketones, such as Vinyl methyl ketone, and methyl isopropenyl ketone, styrene and vinyl ester are used.
Diese bekannten Verfahren führen jedoch zu Polymerisationsprodukten, die wegen der aus dem Methylisopropenylketon stammenden labilen C H3 C O-Gruppen nur eine relativ geringe thermische Beständigkeit, geringe Lichtechtheit, unzureichendes Filmbildungsvermögen und eine schlechte Wasserbeständigkeit aufweisen.However, these known processes lead to polymerization products, because of the unstable C H3 C O groups originating from the methyl isopropenyl ketone only a relatively low thermal resistance, low lightfastness, inadequate Have film-forming ability and poor water resistance.
Es wurde nun gefunden, daß man zu wesentlich besseren Polymerisationsprodukten gelangt, wenn man auf diese labilen Gruppen des Methylisopropenylketons geeignete Monomere aufpfropft, wodurch der ungünstige Einfluß dieser Gruppen ausgeschaltet wird. Zu dieser Aufpolymerisation eignen sich grundsätzlich alle Verbindungen, die auch in reiner Copolymerisation mit dem Methylisopropenylketon polymerisiert werden können. Verbindungen dieser Art sind z. B. Styrol, Vinylchlorid, Acryl- und Methacrylsäure sowie deren Derivate, ferner Butadien und andere mehrfach ungesättigte Bindungen aufweisende Kohlenwasserstoffe.It has now been found that significantly better polymerization products can be obtained if you look at these labile groups of methyl isopropenyl ketone suitable Grafted monomers, thereby eliminating the unfavorable influence of these groups will. In principle, all compounds are suitable for this grafting can also be polymerized in pure copolymerization with methyl isopropenyl ketone can. Connections of this type are e.g. B. styrene, vinyl chloride, acrylic and methacrylic acid and their derivatives, as well as butadiene and other polyunsaturated bonds containing hydrocarbons.
Im Gegensatz zu den in reiner Copolymerisation erhaltenen Mischpolymerisaten werden nach dem erfindungsgemäßen Verfahren Mischpolymerisate von wesentlich besseren Eigenschaften erhalten, wie z. B. höherer thermischer Beständigkeit, besserer Lichtechtheit, besserem Filmbildungsvermögen, höherer spezifischer Viskosität sowie einer besseren Verträglichkeit mit den üblichen Weichmachern. Bei dieser Mischpolymerisation wendet man zweckmäßig gleiche Gewichtsteile Methylisopropenylketon und der Mischungskomponente an, jedoch kann auch eine der Komponenten im fTberschuß angewandt werden. Bei dem anmeldungsgemäßen Verfahren können die gebräuchlichen Polymerisationsbeschleuniger angewandt werden.In contrast to the copolymers obtained in pure copolymerization copolymers of substantially better are obtained by the process according to the invention Get properties such as B. higher thermal resistance, better lightfastness, better film-forming capacity, higher specific viscosity and a better one Compatibility with the usual plasticizers. In this interpolymerization turns one expediently equal parts by weight of methyl isopropenyl ketone and the mixture component on, but one of the components can also be used in excess. In which The processes according to the application can use the customary polymerization accelerators can be applied.
Die Art der Pfropfung kann auf verschiedenste Weise durchgeführt werden, sei es, daß man das polymere Methylisopropenylketon in dem aufzupfropfenden Monomeren, gegebenenfalls unter Verwendung eines Lösungsvermittlers, löst oder das polymere Methylisopropenylketon gemeinsam mit dem aufzupfropfenden Monomeren in einem geeigneten organischen Lösungsmittel polymerisiert.The type of grafting can be carried out in a variety of ways, be it that the polymeric methyl isopropenyl ketone in the monomers to be grafted, optionally using a solubilizer, dissolves or the polymer Methyl isopropenyl ketone together with the monomers to be grafted in a suitable one polymerized organic solvent.
Die Erfindung sei an Hand des nachfolgenden Beispiels näher erläutert.The invention will be explained in more detail with reference to the following example.
Beispiel 200 Gewichtsteile Methylisopropenylketon werden mit 250 Gewichtsteilen Methacrylsäuremethylester gemischt und in Blockpolymerisation in Gegenwart von 0,11/e Benzoylperoxyd bei 40° polymerisiert. Das erhaltene Polymerisat ist ein gelblich gefärbter glasartiger Körper, der beim Erhitzen bereits bei 160° zu starken Verfärbungen unter Zersetzung führt. Die Verträglichkeit dieses Polymerisats mit bekannten Weichmachern, wie Dibutylphthalat, reicht nicht aus, um einen klaren Film zu bilden. Die Filme zeigen zudem eine schlechte Lichtbeständigkeit.Example 200 parts by weight of methyl isopropenyl ketone are mixed with 250 parts by weight Methacrylic acid methyl ester mixed and in block polymerization in the presence of 0.11 / e Benzoyl peroxide polymerized at 40 °. The polymer obtained is yellowish colored glass-like body, which when heated at 160 ° to strong discoloration leads to decomposition. The compatibility of this polymer with known plasticizers, like dibutyl phthalate, is insufficient to form a clear film. The movies also show poor light resistance.
Führt man die gleiche Mischpolymerisation in der Weise durch, daß man zunächst das Methylisopropenylketon mit 0,1 % Benzoylperoxyd bei 60° für sich polymerisiert, worauf man das erhaltene Polymethylisopropenylketon in.Methyläthylketon. löst und in dieser Lösung gemeinsam mit -der gleichen Gewichtsmenge Methacrylsäuremethylester --bei - 80° weiterpolymerisiert, so erhält man ein Mischpolymerisat, welches bis 250° in - glasklarer;- Schmelze beständig ist und gute filmbildende Eigenschafter@ sowie gute Lichtbeständigkeit aufweist.If you carry out the same copolymerization in such a way that you first the methyl isopropenyl ketone with 0.1% benzoyl peroxide at 60 ° for yourself polymerized, whereupon the obtained Polymethyl isopropenyl ketone in methyl ethyl ketone. dissolves and in this solution together with -the same amount by weight Methacrylic acid methyl ester - polymerized further at - 80 °, a copolymer is obtained, which up to 250 ° in - more crystal clear; - melt resistant and good film-forming Propertyer @ as well as good lightfastness.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER17585A DE1004381B (en) | 1955-10-13 | 1955-10-13 | Process for the copolymerization of methyl isopropenyl ketone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER17585A DE1004381B (en) | 1955-10-13 | 1955-10-13 | Process for the copolymerization of methyl isopropenyl ketone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1004381B true DE1004381B (en) | 1957-03-14 |
Family
ID=7400007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER17585A Pending DE1004381B (en) | 1955-10-13 | 1955-10-13 | Process for the copolymerization of methyl isopropenyl ketone |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1004381B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE608681C (en) * | 1933-03-02 | 1935-01-29 | I G Farbenindustrie Akt Ges | Process for the production of plastics |
| FR803563A (en) * | 1935-03-23 | 1936-10-03 | Ig Farbenindustrie Ag | Polymerization products and their production process |
-
1955
- 1955-10-13 DE DER17585A patent/DE1004381B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE608681C (en) * | 1933-03-02 | 1935-01-29 | I G Farbenindustrie Akt Ges | Process for the production of plastics |
| FR803563A (en) * | 1935-03-23 | 1936-10-03 | Ig Farbenindustrie Ag | Polymerization products and their production process |
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