DE956272C - Process for the production of crystal clear polymerisation products - Google Patents
Process for the production of crystal clear polymerisation productsInfo
- Publication number
- DE956272C DE956272C DER15910A DER0015910A DE956272C DE 956272 C DE956272 C DE 956272C DE R15910 A DER15910 A DE R15910A DE R0015910 A DER0015910 A DE R0015910A DE 956272 C DE956272 C DE 956272C
- Authority
- DE
- Germany
- Prior art keywords
- production
- crystal clear
- polymerization
- polymerisation products
- methylol
- 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.)
- Expired
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Description
AUSGEGEBEN AM 17. JANUAR 1957ISSUED JANUARY 17, 1957
R 15910 IVb/39cR 15910 IVb / 39c
Homberg (Ndrh.)Homberg (Ndrh.)
Es ist bekannt, daß 2-Methylol-buten-i-on durch Polymerisation glasklare Produkte ergibt (vgl. deutsche Patentschrift 577256 sowie Gilbert, Morgan, N. J. L. Megson und K. W. Pepper, Colourless Ketonic Resins, Zeitschrift Chemistry and Industry, Jahrgang 1938, S. 887). Die Eigenschaften dieser Polymerisate sind aber weitgehend ungünstig. Neben der großen Sprödigkeit ist besonders die vollständige Unlöslichkeit dieser Polymerisationsprodukte in fast allen Lösungsmitteln einer Weiterverwendung als Kunstharz stark hinderlich.It is known that 2-methylol-buten-i-one by Polymerization gives crystal clear products (see German patent specification 577256 and Gilbert, Morgan, N.J.L. Megson and K.W. Pepper, Colorless Ketonic Resins, Chemistry Journal and Industry, year 1938, p. 887). However, the properties of these polymers are largely unfavorable. In addition to the great brittleness, the complete insolubility of these polymerization products is particularly important in almost all solvents a further use as synthetic resin is a major obstacle.
Es wurde nun gefunden, daß man wertvolle glasklare, in den meisten organischen Lösungsmitteln lösliche Kunststoffe erhält, wenn man Äther des 2 - Methylol - buten -1 - ons - (3) der Polymerisation unterwirft. Diese Äther können beispielsweise nach dem Verfahren der Patentanmeldung R 14032 IVc/39 c durch Umsetzung von 2-Methylol-buten-I-on-(3) unter Zugabe eines Überschusses an einem aliphatischen Alkohol und einer kleinen Menge einer starken Säure, wie Schwefelsäure, Phosphorsäure oder p-Toluolsulfonsäure, bei erhöhter Temperatur gewonnen werden.It has now been found that you can get valuable crystal clear, in most organic solvents Soluble plastics are obtained if the ether of 2 - methylol - buten - 1 - one - (3) is polymerized subject. These ethers can, for example, according to the method of patent application R 14032 IVc / 39 c by converting 2-methylol-buten-I-one- (3) with the addition of an excess of an aliphatic alcohol and a small amount a strong acid such as sulfuric acid, phosphoric acid or p-toluenesulfonic acid at an elevated temperature be won.
Die Polymerisation erfolgt in üblicher Weise und kann mit den üblichen Polymerisationsbeschleunigern, wie Wärme, Licht und Peroxyden, gefördert werden, während geringe Mengen von Inhibitoren, wie z. B. Hydrochinon, die Polymerisation verlangsamen oder ganz verhindern. EsThe polymerization takes place in the usual way and can with the usual polymerization accelerators, such as heat, light and peroxides, be promoted, while small amounts of inhibitors, such as. B. Hydroquinone, the polymerization slow down or prevent it altogether. It
ist vorteilhaft, die Polymerisation unter Ausschluß von Luftsauerstoff durchzuführen, da bei Anwesenheit von Luftsauerstoff ein Vergilben der Polymerisate eintreten kann. Man arbeitet daher zweckmäßig in Gegenwart eines inerten Gases, wie Stickstoff oder Kohlendioxyd.It is advantageous to carry out the polymerization in the absence of atmospheric oxygen, since it is present yellowing of the polymers can occur due to atmospheric oxygen. So you work expediently in the presence of an inert gas such as nitrogen or carbon dioxide.
Die erfindungsgemäß erhaltenen Kunststoffe zeichnen sich durch ihre große Klarheit und Härte, durch große Elastizität und gutes LösungsvermögenThe plastics obtained according to the invention are characterized by their great clarity and hardness, due to great elasticity and good dissolving power
ίο in vielen Lösungsmitteln aus. Auf Grund ihrer Festigkeit und Durchsichtigkeit lassen sich die Polymerisate einerseits als Kunststoffe oder Kunstgläser, wegen ihrer guten Löslichkeit in organischen Lösungsmitteln aber auch als Kunstharze in der Lacktechnik verwenden.ίο in many solvents. Because of your Strength and transparency, the polymers can be on the one hand as plastics or synthetic glasses, because of their good solubility in organic solvents but also as synthetic resins in the Use paint technology.
2OO g 2-Methylol-buten-1 -on- (3) -methyläther2OO g of 2-methylol-buten-1-one- (3) -methyl ether
werden bei 300 4 Tage unter Stickstoff gehalten.are kept at 30 0 for 4 days under nitrogen.
Man erhält ein glasklares Harz, welches in vielen Lösungsmitteln löslich ist, wie z. B. in Äthylacetat, Propylacetat, Butylacetat, Aceton, Methyläthylketon, Benzol und Toluol, ferner in Glykoläthern und Glykolacetaten.A crystal clear resin is obtained, which is soluble in many solvents, such as. B. in ethyl acetate, Propyl acetate, butyl acetate, acetone, methyl ethyl ketone, benzene and toluene, also in glycol ethers and glycol acetates.
Claims (2)
Deutsche Patentschrift Nr. 577 256;
Chemistry and Industry, Jahrgang 1938, S. 887 (Colourless Ketonic Resins).Considered publications:
German Patent No. 577 256;
Chemistry and Industry, year 1938, p. 887 (Colorless Ketonic Resins).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER15910A DE956272C (en) | 1954-04-17 | 1954-04-18 | Process for the production of crystal clear polymerisation products |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE774826X | 1954-04-17 | ||
| DER15910A DE956272C (en) | 1954-04-17 | 1954-04-18 | Process for the production of crystal clear polymerisation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE956272C true DE956272C (en) | 1957-01-17 |
Family
ID=25948070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER15910A Expired DE956272C (en) | 1954-04-17 | 1954-04-18 | Process for the production of crystal clear polymerisation products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE956272C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE577256C (en) * | 1931-05-16 | 1933-06-01 | I G Farbenindustrie Akt Ges | Process for the preparation of unsaturated ketone alcohols |
-
1954
- 1954-04-18 DE DER15910A patent/DE956272C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE577256C (en) * | 1931-05-16 | 1933-06-01 | I G Farbenindustrie Akt Ges | Process for the preparation of unsaturated ketone alcohols |
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