DE950031C - Process for the production of polymers of unsaturated organic compounds - Google Patents
Process for the production of polymers of unsaturated organic compoundsInfo
- Publication number
- DE950031C DE950031C DEP13479D DEP0013479D DE950031C DE 950031 C DE950031 C DE 950031C DE P13479 D DEP13479 D DE P13479D DE P0013479 D DEP0013479 D DE P0013479D DE 950031 C DE950031 C DE 950031C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- organic compounds
- polymers
- oxidizing agents
- 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
- 229920000642 polymer Polymers 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 6
- 150000002894 organic compounds Chemical class 0.000 title claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 15
- 239000003638 chemical reducing agent Substances 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000002081 peroxide group Chemical group 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000002978 peroxides Chemical group 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- 229940048086 sodium pyrophosphate Drugs 0.000 description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PNXAPWZUZUZMDA-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PNXAPWZUZUZMDA-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- -1 glucose Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and 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
- C08F36/04—Homopolymers and 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)
- Compositions Of Macromolecular Compounds (AREA)
Description
Verfahren zur Herstellung von Polymerisaten ungesättigter organischer Verbindungen Man hat :schon die Polymerisation von einfach ungesättigten Verbindungen in Gegenwart von Oxydationsmitteln und überschüssigenReduktionsmitteln, bezogen auf die verwendeten Oxydationsmittel, durc'hgefü'hrt. Der Vorteil des Verfahrens liegt in einer wesentlich erhöhten Reaktionsgeschwindigkeit und einer guten Beherrschbarkeit der Reaktion.Process for the production of polymers of unsaturated organic Compounds One has: already the polymerization of monounsaturated compounds in the presence of oxidizing agents and excess reducing agents on the oxidizing agents used. The advantage of the procedure lies in a significantly increased reaction speed and good controllability the reaction.
Es wurde nun gefunden, daß man Polymerisate oder Mischpolymerisate mehrfach ungesättigter organischer Verbindungen für sich oder im Gemisch, miteinander oder mit einfach ungesättigten organischen Verbindungen im wäßrigen Medium in Gegenwart von Oxydationsmitteln mit Peroxydstruktur und von die Polymerisation nicht störenden, mit den Oxydationsmitteln unter den Reaktionsbedingungen reagierenden Reduktionsmitteln dadurch herstellen kann, daß die Reduktionsmittel im Übersc'huß, bezogen auf die Oxydationsmittel, angewandt werden, wobei zweckmäßigerweise molekularer Sauerstoff möglichst weitgehend ausgeschlossen wird.It has now been found that polymers or copolymers can be used polyunsaturated organic compounds alone or in a mixture with one another or with monounsaturated organic compounds in an aqueous medium in the presence of oxidizing agents with a peroxide structure and of those that do not interfere with the polymerization, reducing agents reacting with the oxidizing agents under the reaction conditions can thereby produce that the reducing agent in excess, based on the Oxidizing agents, may be used, advantageously molecular oxygen is excluded as far as possible.
Das Verfahren hat bei der Polymerisation von Dienen noch besondere Vorteile. Polymerisiert man Diene nur mit Hilfe von Oxydationsmitteln oder mit überschüssigen Oxydationsmitteln, so können sich ungünstige Einwirkungen des oxydierenden Katalysators auf das fertige Polymerisat ergeben. Um dies zu verhindern, hat man z. B. bei der Polymerisation mit Persulfaten nach beendigter Polymerisation starke Reduktionsmittel zugegeben und dadurch den peroxydischen Katalysator zerstört. Noch ungünstiger können sich organischePeroxyde auswirken, die im Polymerisat verbleiben; beispielsweise ist von Benzoylperoxyd bekannt, daß es auf Kautschuk vulkanisierend wirkt; außerdem werden gewisse Alterungsschutzmittel, wie z. B. Phenyl-ß-naphthylamin, angegriffen. Es ist deshalb wesentlich, möglichst geringe Mengen an peroxydischen Katalysatoren anzuwenden, die zwar für die Polymerisation ausreichen, am Ende derselben aber verbraucht sind. DieserForderung kann durch Anwendung überschüssiger Reduktionsmittel gemäß der Erfindung leicht entsprochen werden. Die notwendige und ausreichende Menge des Oxydationsmittels kann durch wenige Versuche ermittelt werden, da bei .einer gegebenen Menge an Reduktionsmitteln und einer unzureichenden Menge des Oxydationsmittels die Polymerisation vorzeitig aufhört und ohne Zusatzeiner weiteren Menge des Oxydationsmittels nicht zu Ende geführt werden kann.The process has special features in the polymerization of dienes Advantages. If dienes are polymerized only with the help of oxidizing agents or with excess Oxidizing agents, so can unfavorable effects of the oxidizing Catalyst result in the finished polymer. To prevent this, one has z. B. strong in the polymerization with persulfates after completion of the polymerization Adding reducing agent and thereby destroying the peroxide catalyst. Yet Organic peroxides that remain in the polymer can have a less favorable effect; For example, benzoyl peroxide is known to vulcanize on rubber acts; In addition, certain anti-aging agents, such as. B. Phenyl-ß-naphthylamine, attacked. It is therefore essential to use the smallest possible amounts of peroxidic Apply catalysts that are sufficient for the polymerization, at the end of the same but are used up. This requirement can be met by using excess reducing agents easily met according to the invention. The necessary and sufficient amount of the oxidizing agent can be determined by a few experiments, since with .einer given amount of reducing agents and an insufficient amount of oxidizing agent the polymerization ceases prematurely and without the addition of an additional amount of the oxidizing agent cannot be completed.
Der Zusatz von Oxydations- und Reduktionsmitteln kann in beliebiger Weise geschehen, wenn nur dafür gesorgt wird, daß das Reduktionsmittel sich immer im Überschuß befindet. Die durch das beschriebene Verfahren bewirkte Polymerisationsbeschleunigung erlaubt auch das Arbeiten bei tieferen Temperaturen, als es ohne Anwendung von Reduktionsmitteln möglich ist. Dies wirkt sich auf die Eigenschaften der Polymerisate günstig aus.The addition of oxidizing and reducing agents can be in any Wise done, if only care is taken that the reducing agent is always turned off is in excess. The acceleration of polymerization brought about by the process described also allows working at lower temperatures than would be the case without the use of reducing agents is possible. This has a favorable effect on the properties of the polymers.
Geeignete Oxydationsmittel sind z. B. die Persulfate, Wasserstoffperoxyd., Benzoylperoxyd; brauchbare Reduktionsmittel sind z. B. reduzierend wirkende Zucker, wie Glucose, ferner Benzoin und Natriumformaldehydsulfoxylat.Suitable oxidizing agents are, for. B. the persulfates, hydrogen peroxide., Benzoyl peroxide; useful reducing agents are e.g. B. reducing sugars, such as glucose, also benzoin and sodium formaldehyde sulfoxylate.
Es ist zweckmäßig, den Luftsauerstoff möglichst ,weitgehend auszuschließen, da er den Ablauf der Polymerisation stört.It is advisable to exclude the oxygen in the air as far as possible, because it interferes with the polymerization process.
Durch geeignete Wahl der Reaktionstemperatur und des pH-Wertes der Emulgatorlösung kann die Polymerisation weiterhin beeinflußt werden. Beispiel 1 In 2ooo Gewichtsteilen einer wäßrigen Lösung, die6oGewichtsteile diisobutylnaphthal@insulfosaures Natrium, 16 Gewichtsteile Natriumpyrophosphat, 4,7 Gewichtsteile Natriumhydroxyd und 3o Ge-,vichtsteile Ölsäure enthält, werden 75o Gewichtsteile Butadien und 25o Gewichtsteile Styrol emulgiert. Unter Zusatz von 2,5 Gewichtsteilen Ammoniumpersulfat erhält man bei 4o° nach 24Stunden 2o,7 0/0 eines kautschukähnlichen Polymerisates. Werden dem Ansatz außerdem 5 Gewichtsteile Traubenzucker oder Arabinose oder Galaktose zugesetzt; so' erhält man dagegen in derselben Zeit 39,3 bzw. 43,3 bzw. 31,3% Ausbeute. Wird der Ansatz mit 1 Gewichtsteil Diisopropylxanthogendisulfid geregelt, so erhält man mit Traubenzucker nach derselben Zeit 30,3% Polymerisat, während ohne Zusatz von Traubenzucker nur 17% erhalten werden. Werden an Stelle von 21/2 Gewichtsteilen Ammoniumpersulfat 1o Gewichtsteile 30%iges Wasserstoffsuperoxyd angewandt, so erhält man nach 3 Stunden ohne weitere Zusätze 2,9% Polymerisat. Werden diesem Ansatz 5 Gewichtsteile Traubenzucker zugesetzt, so erhält man in derselben Zeit q.5,20/0, mit 3 Gewichtsteilen Dioxyaceton 23,7% Ausbeute. Wird der Ansatz, der 1o Gewichtsteile 30%iges Wasserstoffsuperoxyd und 5 Gewichtsteile Traubenzucker enthält, mit einem halben Gewichtsteil Diisopropylxanthogendisulfid geregelt, so erhält man 24,8%, ohne Traubenzucker dagegen nur o,9% Polymerisat. An Stelle von Ammonpersulfat bzw. Wasserstoffperoxyd kann man mit ähnlichem Erfolg z. B. Natriumpercarbonat anwenden. Beispiele In 2ooo Gewichtsteilen einer wäßrigen Lösung, wie sie im Beispiel 1 angewandt wurde, werden 75o Gewichtsteile Butadien und 25o Gewichtsteile Styrol emulgiert. Unter Zusatz von 2 Gewichtsteilen Benzoylperoxyd erhält man bei 40° nach 14 Stunden 11,8% eines kautschukähnlichen Polymezisates. Werden dem Ansatz außerdem 3 Gewichtsteile Benzoin oder 3 Gewichtsteile Oxymethylbenzoin zugesetzt, so erhält man in derselben Zeit 63,5 bzw. 72,50/0, mit 5 Gewichtsteilen Benzoin 98,4% Ausbeute. Beispiel 3 In 2ooo Gewichtsteilen einer wäßrigen Lösung, die 3o Gewichtsteile diisobutylnaphthalinsulfosaures Natrium, 11,2 Gewichtsteile Seifenfettsäure, 2,4 Gewichtsteile Natriumhydroxyd und 2o Gewichtsteile Natriumpyrophosphat enthält, werden 75o Gewichtsteile B.utadien und: 25o Gewichtsteile Styrol emulgiert. Werden dieser Emulsion 21/2 Gewichtsteile Benzoylperoxyd zugesetzt, so erhält man nach 41/2 Stunden bei 40° weniger als 2% Polymerisat. Werden außer-dem 16 Gewichtsteile Ferro-ammonsulfat zugegeben, so. erhält man in derselben Zeit und unter denselben Bedingungen 9570/0 Polymerisat.By suitable choice of the reaction temperature and the pH value of the The polymerization can still be influenced by emulsifier solution. example 1 In 2,000 parts by weight of an aqueous solution, the 6o parts by weight of diisobutylnaphthal @ insulfosaures Sodium, 16 parts by weight sodium pyrophosphate, 4.7 parts by weight sodium hydroxide and contains 3o parts by weight of oleic acid, 75o parts by weight are butadiene and 25o Parts by weight of styrene emulsified. With the addition of 2.5 parts by weight of ammonium persulfate at 40 ° after 24 hours 20.7% of a rubber-like polymer is obtained. Add 5 parts by weight of glucose or arabinose or galactose to the approach added; on the other hand, 39.3%, 43.3% and 31.3% yield, respectively, are obtained in the same time. If the batch is regulated with 1 part by weight of diisopropylxanthogen disulfide, then this is obtained one with grape sugar after the same time 30.3% polymer, while without addition only 17% of glucose can be obtained. Used in place of 21/2 parts by weight Ammonium persulfate 1o parts by weight of 30% hydrogen peroxide is used after 3 hours without further additives, 2.9% polymer. Will this approach 5 Parts by weight of dextrose added, one obtains in the same time q 5.20 / 0, with 3 parts by weight of dioxyacetone 23.7% yield. Will the approach of 1o parts by weight Contains 30% hydrogen peroxide and 5 parts by weight of grape sugar, with a half part by weight of diisopropylxanthogen disulfide regulated, this gives 24.8%, without grape sugar, on the other hand, only 0.9% polymer. Instead of ammonium persulphate or Hydrogen peroxide can be used with similar success z. B. Use sodium percarbonate. EXAMPLES In 2,000 parts by weight of an aqueous solution as used in Example 1 75o parts by weight of butadiene and 250 parts by weight of styrene are emulsified. With the addition of 2 parts by weight of benzoyl peroxide, it is obtained at 40 ° after 14 hours 11.8% of a rubber-like polymer. If the approach is also 3 parts by weight Benzoin or 3 parts by weight of oxymethylbenzoin are added, it is obtained in the same Time 63.5 and 72.50 / 0, with 5 parts by weight of benzoin 98.4% yield. Example 3 In 2ooo parts by weight of an aqueous solution, the 3o parts by weight of diisobutylnaphthalenesulfonic acid Sodium, 11.2 parts by weight of soap fatty acid, 2.4 parts by weight of sodium hydroxide and Contains 2o parts by weight of sodium pyrophosphate, 75o parts by weight of B.utadiene and: 250 parts by weight of styrene emulsified. This emulsion will be 21/2 parts by weight Benzoyl peroxide added, after 41/2 hours at 40 ° less than 2% is obtained Polymer. If 16 parts by weight of ferro-ammonium sulfate are also added, so. 9570/0 polymer is obtained in the same time and under the same conditions.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13479D DE950031C (en) | 1943-10-15 | 1943-10-15 | Process for the production of polymers of unsaturated organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13479D DE950031C (en) | 1943-10-15 | 1943-10-15 | Process for the production of polymers of unsaturated organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE950031C true DE950031C (en) | 1956-10-04 |
Family
ID=7364632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP13479D Expired DE950031C (en) | 1943-10-15 | 1943-10-15 | Process for the production of polymers of unsaturated organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE950031C (en) |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE593399C (en) * | 1932-03-05 | |||
| DE504436C (en) * | 1929-03-22 | 1930-08-07 | I G Farbenindustrie Akt Ges | Process for the preparation of polymerisation products of butadiene hydrocarbons which are soluble in organic solvents |
| DE608681C (en) * | 1933-03-02 | 1935-01-29 | I G Farbenindustrie Akt Ges | Process for the production of plastics |
| US2097263A (en) * | 1936-07-07 | 1937-10-26 | Du Pont | Polymerization product and process of polymerization |
| DE664351C (en) * | 1933-05-12 | 1938-08-25 | I G Farbenindustrie Akt Ges | Process for the production of polyvinyl esters |
| FR843903A (en) * | 1937-09-29 | 1939-07-12 | Ig Farbenindustrie Ag | Polymerization process |
| US2168808A (en) * | 1937-07-02 | 1939-08-08 | Goodrich Co B F | Acceleration of vinyl halide polymerization |
| DE679587C (en) * | 1937-12-24 | 1939-08-09 | I G Farbenindustrie Akt Ges | Emulsion polymerization of butadiene or its derivatives |
| AT157424B (en) * | 1938-05-14 | 1939-11-10 | Ig Farbenindustrie Ag | Process for the polymerization of butadienes. |
| GB514912A (en) * | 1938-05-18 | 1939-11-21 | James Gordon Anderson | Improvements in or relating to the manufacture and application of synthetic rubber-like materials |
| US2227517A (en) * | 1937-07-30 | 1941-01-07 | Du Pont | Plastic polymer and process of producing the same |
| GB549234A (en) * | 1939-10-06 | 1942-11-12 | Norton Grinding Wheel Co Ltd | Method of polymerizing unsaturated methylene compounds |
| CH224217A (en) * | 1939-04-22 | 1942-11-15 | Wacker Chemie Gmbh | Process for the polymerization of vinyl compounds. |
-
1943
- 1943-10-15 DE DEP13479D patent/DE950031C/en not_active Expired
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE504436C (en) * | 1929-03-22 | 1930-08-07 | I G Farbenindustrie Akt Ges | Process for the preparation of polymerisation products of butadiene hydrocarbons which are soluble in organic solvents |
| DE593399C (en) * | 1932-03-05 | |||
| DE608681C (en) * | 1933-03-02 | 1935-01-29 | I G Farbenindustrie Akt Ges | Process for the production of plastics |
| DE664351C (en) * | 1933-05-12 | 1938-08-25 | I G Farbenindustrie Akt Ges | Process for the production of polyvinyl esters |
| US2097263A (en) * | 1936-07-07 | 1937-10-26 | Du Pont | Polymerization product and process of polymerization |
| US2168808A (en) * | 1937-07-02 | 1939-08-08 | Goodrich Co B F | Acceleration of vinyl halide polymerization |
| US2227517A (en) * | 1937-07-30 | 1941-01-07 | Du Pont | Plastic polymer and process of producing the same |
| FR843903A (en) * | 1937-09-29 | 1939-07-12 | Ig Farbenindustrie Ag | Polymerization process |
| DE679587C (en) * | 1937-12-24 | 1939-08-09 | I G Farbenindustrie Akt Ges | Emulsion polymerization of butadiene or its derivatives |
| AT157424B (en) * | 1938-05-14 | 1939-11-10 | Ig Farbenindustrie Ag | Process for the polymerization of butadienes. |
| GB514912A (en) * | 1938-05-18 | 1939-11-21 | James Gordon Anderson | Improvements in or relating to the manufacture and application of synthetic rubber-like materials |
| CH224217A (en) * | 1939-04-22 | 1942-11-15 | Wacker Chemie Gmbh | Process for the polymerization of vinyl compounds. |
| FR881919A (en) * | 1939-04-22 | 1943-05-12 | Wacker Chemie Gmbh | Process for the polymerization of vinyl compounds |
| GB549234A (en) * | 1939-10-06 | 1942-11-12 | Norton Grinding Wheel Co Ltd | Method of polymerizing unsaturated methylene compounds |
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