DE281688C - - Google Patents
Info
- Publication number
- DE281688C DE281688C DE1914281688D DE281688DA DE281688C DE 281688 C DE281688 C DE 281688C DE 1914281688 D DE1914281688 D DE 1914281688D DE 281688D A DE281688D A DE 281688DA DE 281688 C DE281688 C DE 281688C
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- catalysts
- vinyl
- organic
- products
- 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 - Lifetime
Links
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920001567 vinyl ester resin Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 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
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 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
- C08F18/00—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 acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/20—Esters containing halogen
-
- 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
- C08F16/12—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 an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/16—Monomers containing no hetero atoms other than the ether oxygen
- C08F16/18—Acyclic compounds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/16—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated carboxylic acids or unsaturated organic esters, e.g. polyacrylic esters, polyvinyl acetate
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Paints Or Removers (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
Nach dem Hauptpatent 281687 werden organische Vinylester dadurch in wertvolle Produkte übergeführt, daß man diese Vinylester durch Erwärmen, Belichten oder andere PoIymerisationsmethoden, z. B. gleichzeitiges Erwärmen und Belichten, polymerisiert.According to the main patent 281687, organic Vinyl esters converted into valuable products by these vinyl esters being heated, exposed to light or other polymerization methods, z. B. simultaneous heating and exposure, polymerized.
Es wurde nun gefunden, daß in allen diesen Fällen der Vorgang durch katalytisch wirkende Substanzen außerordentlich beschleunigt werden kann. Als Katalysatoren kommen /.. B. die organischen Superoxyde, die Ozonide, die organischen Säurcanhydride in Verbindung mit Sauerstoff oder Sauerstoff abgebenden Mitteln (Perborate, Perkarbonate) sowie gewisse Metalloxyde, z. B. Silberoxyd, in Betracht.It has now been found that in all these cases the process is catalytically active Substances can be accelerated extraordinarily. The catalysts are / .. B. the organic super oxides, the ozonides, the organic acid anhydrides in connection with Oxygen or oxygen-releasing agents (perborates, percarbonates) and certain metal oxides, z. B. silver oxide into consideration.
Die. in Betracht kommenden Katalysatoren wirken einerseits beschleunigend auf die Reaktion ein, während dieselben anderseits die Fähigkeit besitzen, die Eigenschaften der erzielten Polymerisationsprodukte mehr oder weniger zu beeinflussen. Man ist mithin in der Lage, durch Anwendung bestimmter Katalysatoren in gegebenen Fällen die Eigenschaften der Produkte zu modifizieren.The. On the one hand, suitable catalysts have an accelerating effect on the reaction on the one hand, while on the other hand they have the ability to change the properties of the obtained To influence polymerization products more or less. You are therefore able to use certain catalysts to modify the properties of the products in given cases.
ι kg Chloressigsäurevinylester wird mit 0,5 bis ι g Benzoylsuperoxyd versetzt und in einem geräumigen, mit Rückflußkühler versehencn Gefäß vorsichtig erwärmt. Bei 80 bis ioo° tritt unter raschem Ansteigen der Temperatur der Polymerisationsvorgang ein, in diesem Moment ist für Kühlung des Reaktionsgefäßes zu sorgen. Man kann den etwas stürmi- sehen Verlauf des Prozesses dadurch mildern, daß man die Reaktionsflüssigkeit von vorn- · herein mit einem indifferenten Lösungsmittel verdünnt, in vorliegendem Beispiel etwa mit 300 g Chlorbenzol.ι kg of vinyl chloroacetate is 0.5 up to 1 g of benzoyl peroxide are added and placed in a spacious, reflux condenser The vessel is carefully warmed. At 80 to 100 ° the temperature rises rapidly the polymerization process starts, at this moment the reaction vessel must be cooled. You can see the somewhat stormy see the course of the process attenuated by removing the reaction liquid from the front diluted in with an inert solvent, in the present example with 300 g chlorobenzene.
Das Reaktionsprodukt stellt einen zähen Sirup dar, der in verschiedener Weise weiter verarbeitet werden kann; z. B. erhält man durch Belichten des ohne Verdünnungsmittel erhaltenen Sirups in sehr kurzer Zeit die in dem Hauptpatent beschriebenen wertvollen festen Massen, indem sich auch der noch unverändert gebliebene Vinylester polymerisiert. Auch dadurch, daß man letzteren und das eventuell zugesetzte Verdünnungsmittel im Vakuum abdestilliert, kann man die festen Massen erhalten. 5"The reaction product is a viscous syrup that continues in various ways can be processed; z. B. is obtained by exposing the without diluent syrups obtained the valuable solid described in the main patent in a very short time Masses in which the still unchanged vinyl ester polymerizes. Also by that the latter and any added diluent are distilled off in vacuo, one can get the solid masses. 5 "
ι kg Chloressigsäurevinylester wird mit etwa 2 g Silberoxyd unter Rühren erwärmt. Bei etwa 100° setzt der Polymerisationspr'ozcßein, und unter mäßiger Wärmeentwicklung verwandelt sich im Laufe von ungefähr 1 Stunde die ganze Flüssigkeit in eine hellbräunliche zähe Masse, die je nach dem Verwendungszweck in geeigneter Weise, z. B. durch Abdunsten im Vakuum, Lösen usw., weiterverarbeitet wird.ι kg of vinyl chloroacetate is heated with about 2 g of silver oxide while stirring. at The polymerization process begins at about 100 ° and is transformed with moderate evolution of heat In the course of about 1 hour all the liquid turns into a light brownish viscous Mass, which depending on the intended use in a suitable manner, for. B. by evaporation in Vacuum, loosening, etc., is further processed.
I3A τ E N τ - A ν s i' R υ c ii:I 3 A τ EN τ - A ν si ' R υ c ii:
Abänderung des Verfahrens zur Herstellung wertvoller Produkte aus organischen Vinylestern nach Patent 281687, dadurch gekennzeichnet, daß man die Polymerisation der Vinylester in Gegenwart von Katalysatoren vornimmt.Modification of the process for the production of valuable products from organic Vinyl esters according to Patent 281687, characterized in that the polymerization the vinyl ester takes place in the presence of catalysts.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE281687T | 1913-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE281688C true DE281688C (en) |
Family
ID=32585097
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1913281687D Expired - Lifetime DE281687C (en) | 1913-07-03 | 1913-07-03 | |
| DE1914281688D Expired - Lifetime DE281688C (en) | 1913-07-03 | 1914-04-02 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1913281687D Expired - Lifetime DE281687C (en) | 1913-07-03 | 1913-07-03 |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE281687C (en) |
| FR (1) | FR474086A (en) |
| GB (1) | GB191415271A (en) |
| NL (1) | NL3351C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE751853C (en) * | 1938-08-02 | 1951-10-31 | Albert Ag Chem Werke | Process for polymerizing vinyl compounds |
| DE1074860B (en) * | 1960-02-04 | Rohm & Haas G.m.b.H., Darmstadt | Process for the preparation of polymeric compounds containing thiol groups and based on vinyl monochloroacetate | |
| DE1235591B (en) * | 1964-04-15 | 1967-03-02 | Hoechst Ag | Process for the polymerization of vinyl esters |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2821504A (en) * | 1952-12-06 | 1958-01-28 | Koppers Co Inc | Changeover valves for regenerative ovens |
| DE1060142B (en) * | 1956-12-28 | 1959-06-25 | Ministerul Ind Petrolului | Process for making low molecular weight polyvinyl acetate bead polymers |
-
0
- NL NL3351D patent/NL3351C/xx active
-
1913
- 1913-07-03 DE DE1913281687D patent/DE281687C/de not_active Expired - Lifetime
-
1914
- 1914-04-02 DE DE1914281688D patent/DE281688C/de not_active Expired - Lifetime
- 1914-06-25 GB GB191415271D patent/GB191415271A/en not_active Expired
- 1914-06-25 FR FR474086D patent/FR474086A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1074860B (en) * | 1960-02-04 | Rohm & Haas G.m.b.H., Darmstadt | Process for the preparation of polymeric compounds containing thiol groups and based on vinyl monochloroacetate | |
| DE751853C (en) * | 1938-08-02 | 1951-10-31 | Albert Ag Chem Werke | Process for polymerizing vinyl compounds |
| DE1235591B (en) * | 1964-04-15 | 1967-03-02 | Hoechst Ag | Process for the polymerization of vinyl esters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR474086A (en) | 1915-02-05 |
| GB191415271A (en) | 1915-10-21 |
| NL3351C (en) | |
| DE281687C (en) |
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