DE703582C - Process for the preparation of polymerization products from butadienes - Google Patents
Process for the preparation of polymerization products from butadienesInfo
- Publication number
- DE703582C DE703582C DE1937I0059195 DEI0059195D DE703582C DE 703582 C DE703582 C DE 703582C DE 1937I0059195 DE1937I0059195 DE 1937I0059195 DE I0059195 D DEI0059195 D DE I0059195D DE 703582 C DE703582 C DE 703582C
- Authority
- DE
- Germany
- Prior art keywords
- butadienes
- preparation
- polymerization products
- weight
- parts
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 7
- 238000006116 polymerization reaction Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 6
- YFFCIMCCNCFYPB-UHFFFAOYSA-N 5-chloro-1-methoxypenta-1,3-diene Chemical compound COC=CC=CCCl YFFCIMCCNCFYPB-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KTNFTWKBRMSZKQ-UHFFFAOYSA-N 1-butoxy-5-chloropenta-1,3-diene Chemical compound C(CCC)OC=CC=CCCl KTNFTWKBRMSZKQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PCPYTNCQOSFKGG-UHFFFAOYSA-N 1-chlorobuta-1,3-diene Chemical compound ClC=CC=C PCPYTNCQOSFKGG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verfahren zur Herstellung von Polymerisationsprodukten aus Butadienen Gegenstand vorliegender Erfindung ist die Herstellung neuer Polymerisationsprodukte. Das Verfahren ist dadurch gekennzeichnet, daB Butadiene der Mischpolymerisation in Emulsion mit Halogenpentadienyläthern der folgenden Konstitution: unterworfen werden. Bei den durch die obengenannte Formel definierten Ausgangsmaterialien wird als Halogen in erster Linie Chlor und als Alkyl z. B. Methyl oder Butyl angewandt. Unter dem Ausdruck Butadiene werden sowohl Butadien selbst als auch dessen Substitutionsprodukte, wie z. B. Isopren oder a-Chlorbutadien, verstanden. Selbstverständlich können auch noch andere polymerisationsfähige Komponenten bei der Durchführung des neuen Verfahrens zusätzlich angewandt werden. Hierfür kommen vorzugsweise solche mit aktivierten Vinylgruppen in Frage, z. B. Vinylbenzole oder Acrylsäurederivate.Process for the preparation of polymerization products from butadienes The present invention relates to the preparation of new polymerization products. The process is characterized in that butadienes are copolymerized in emulsion with halopentadienyl ethers of the following constitution: be subjected. In the starting materials defined by the above formula, the halogen is primarily chlorine and the alkyl z. B. methyl or butyl applied. The term butadienes includes both butadiene itself and its substitution products, such as. B. isoprene or α-chlorobutadiene understood. Of course, other polymerizable components can also be used when carrying out the new process. For this purpose, those with activated vinyl groups are preferred, e.g. B. vinylbenzenes or acrylic acid derivatives.
Die erhältlichen kautschukähnlichen Polymerisate sind besser verarbeitbar als die bisher bekannten Mischpolymerisate von Butadien mit anderen polymerisierbaren Substanzen. Die neuen Polymerisate können in üblicher Weise vulkanisiert werden und zeichnen sich im vulkanisierten Zustand vor den genannten Produkten durch eine erhöhte Dehnung und eine verringerte Härte aus.The rubber-like polymers available are easier to process than the previously known copolymers of butadiene with other polymerizable Substances. The new polymers can be vulcanized in the usual way and are characterized in the vulcanized state by a increased elongation and decreased hardness.
Die als Ausgangsmaterial dienenden Halogenpentadienyläther können hergestellt werden gemäß der Arbeit in »Journal of American Chemical Society«, Bd. 58, S. 1748.The halopentadienyl ethers used as starting material can getting produced according to work in Journal of American Chemical Society ", Vol. 58, p. 1748.
Beispiel i 75 Gewichtsteile Butadien und 25 Gewichtsteile Chlorpentadienylmethylätlier werden in i50 Gewichtsteilen io°/oiger Natriumoleatlösung unter Rühren emulgiert und nach Zusatz von 0.35 Gewichtsteilen Ammonpersulfat 70 Stunden bei 30° polymerisiert. Das durch Koagulation erhaltene Poly merisat ist gut verarbeitbar und läßt sich in üblicher Weise vulkanisieren. Das Vulkanisat ist durch hohe Dehnung und geringe Härte ausgezeichnet.Example i 75 parts by weight of butadiene and 25 parts by weight of chloropentadienylmethyl ether are emulsified in 150 parts by weight of 10% sodium oleate solution with stirring and, after addition of 0.35 part by weight of ammonium persulfate, polymerized at 30 ° for 70 hours. The polymer obtained by coagulation is easy to process and can be vulcanized in the usual way. The vulcanizate is characterized by high elongation and low hardness.
Beispiel 2 An Stelle des im vorigen Beispiel angeführten Chlorpentadienylmethyläthers wird die Polymerisation unter Verwendung des n-Butyläthers unter sonst gleichen Bedingungen durchgeführt. Bereits nach einer Polymerisationsdauer von 4o Stunden wird ein Polymerisat von den im Beispiel i erwähnten Eigenschaften erhalten. Beispiel 3 Ein Gemisch aus 75 Gewichtsteilen 2-Chlorbutadien und 25 Gewichtsteilen Chlorpentadienyl-n-butyläther, das g Gewichtsteile Phen-",pxypropenoxyd gelöst enthält, wird in i oo ?'nwichtsteilen 20%iger \atriumoleatlösung unter Rühren emulgiert und bei 30° in 5 Stunden bis zu einer Ausbeute von 7090 ° polymerisiert. Das erhaltene Polymerisat zeichnet sich durch ein höheres Festigkeitsplateau bei besserer Verarbeitbarkeit vor Polymerisaten aus reinem 2-Chlorbutadien aus.Example 2 Instead of the chloropentadienyl methyl ether mentioned in the previous example the polymerization using n-butyl ether is otherwise the same Conditions carried out. Already after a polymerization time of 40 hours a polymer with the properties mentioned in Example i is obtained. example 3 A mixture of 75 parts by weight of 2-chlorobutadiene and 25 parts by weight of chloropentadienyl-n-butyl ether, the g parts by weight of phen- ", contains pxypropenoxide dissolved, is in i oo? 'nwichtstpeile 20% iger \ atrium oleate solution emulsified with stirring and at 30 ° in 5 hours up to polymerized in a yield of 7090 °. The polymer obtained is noticeable due to a higher strength plateau with better processability before polymers made from pure 2-chlorobutadiene.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1937I0059195 DE703582C (en) | 1937-10-01 | 1937-10-01 | Process for the preparation of polymerization products from butadienes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1937I0059195 DE703582C (en) | 1937-10-01 | 1937-10-01 | Process for the preparation of polymerization products from butadienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE703582C true DE703582C (en) | 1941-03-12 |
Family
ID=7194954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1937I0059195 Expired DE703582C (en) | 1937-10-01 | 1937-10-01 | Process for the preparation of polymerization products from butadienes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE703582C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445378A (en) * | 1943-07-22 | 1948-07-20 | Standard Oil Dev Co | Alkoxypolyolefin polymers and process of making same |
-
1937
- 1937-10-01 DE DE1937I0059195 patent/DE703582C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445378A (en) * | 1943-07-22 | 1948-07-20 | Standard Oil Dev Co | Alkoxypolyolefin polymers and process of making same |
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