GB421146A - Improvements in the manufacture and production of artificial masses - Google Patents
Improvements in the manufacture and production of artificial massesInfo
- Publication number
- GB421146A GB421146A GB6445/34A GB644534A GB421146A GB 421146 A GB421146 A GB 421146A GB 6445/34 A GB6445/34 A GB 6445/34A GB 644534 A GB644534 A GB 644534A GB 421146 A GB421146 A GB 421146A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butadiene
- product
- agents
- emulsion
- heating
- 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
- 238000004519 manufacturing process Methods 0.000 title 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- 239000000839 emulsion Substances 0.000 abstract 12
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 abstract 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 8
- 239000003570 air Substances 0.000 abstract 8
- 238000010438 heat treatment Methods 0.000 abstract 8
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 6
- 238000005096 rolling process Methods 0.000 abstract 6
- 238000010792 warming Methods 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 4
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 abstract 4
- 239000004902 Softening Agent Substances 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 230000001112 coagulating effect Effects 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 238000012856 packing Methods 0.000 abstract 4
- 229910052708 sodium Inorganic materials 0.000 abstract 4
- 239000011734 sodium Substances 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- 238000004073 vulcanization Methods 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 229920001971 elastomer Polymers 0.000 abstract 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005642 Oleic acid Substances 0.000 abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910045601 alloy Inorganic materials 0.000 abstract 2
- 239000000956 alloy Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- -1 aromatic hydroxy compounds Chemical class 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000006229 carbon black Substances 0.000 abstract 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 2
- 238000000576 coating method Methods 0.000 abstract 2
- 230000003247 decreasing effect Effects 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 230000001804 emulsifying effect Effects 0.000 abstract 2
- 239000000945 filler Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000011261 inert gas Substances 0.000 abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- AXLHVTKGDPVANO-UHFFFAOYSA-N methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound COC(=O)C(N)CNC(=O)OC(C)(C)C AXLHVTKGDPVANO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 230000000379 polymerizing effect Effects 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 230000008961 swelling Effects 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 238000009736 wetting Methods 0.000 abstract 2
- 239000000080 wetting agent Substances 0.000 abstract 2
- 239000003340 retarding agent Substances 0.000 abstract 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
- C08F36/14—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 containing elements other than carbon and hydrogen
- C08F36/16—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 containing elements other than carbon and hydrogen containing halogen
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)
Abstract
Elastic, ductile products are obtained by polymerizing 1-chlor-butadiene-1 : 3 in the absence of large amounts of oxygen, for example, in presence of nitrogen, hydrogen, or inert gases, at decreased, atmospheric or increased pressure. The process may be carried out at temperatures of from 0--100 DEG C., but preferably at 0--50 DEG C.; accelerating agents such as oxygen, air, alkali metals, their alloys, peroxides such as benzoyl peroxide or hydrogen peroxide, and actinic rays may be employed, or, alternatively, retarding agents such as aromatic hydroxy compounds, or amines, or low temperatures. Non-polymerizable solvents or diluents such as dimethyl ether, diethyl ether, hydrocarbons, such as benzene, carbon tetrachloride and other chlorinated hydrocarbons, or polymerizable solvents such as butadiene, isoprene, styrene, and methyl-isopropenyl-ketone, or an aqueous medium giving an emulsion may also be employed. When an emulsion of the 1-chlor-butadiene-1 : 3 is employed, stabilizing agents such as wetting or emulsifying agents may be added, with, if desired, accelerators or retarders and with natural latex or other emulsions. The products may be obtained soluble, insoluble or capable of swelling, in organic solvents and may be obtained mixed with fillers, acid binding agents, softening agents, vulcanization accelerators, anti-agers, dyes, or sulphur, added during, before, or after the polymerization. The products may be used as solutions, pastes or emulsions, for impregnating, as coating materials, packings, putties, and as solids, for motor car tyres, conveying bands, packings stable to oil and like technical rubber articles. According to examples, 1 - chlor - butadiene-1 : 3 is polymerized, (1) by heating in a vacuum at 30 DEG C. and the product worked up with aldol-a -naphthylamine into a sheet; (2) by heating at 25 DEG C. with benzoyl peroxide and toluene, the product being worked up for a coating-mass or by vulcanization; (3) by heating in vacuo with benzoyl peroxide at 60 DEG C. to give an elastic product suitable for rolling; (4) by warming with sodium at 30 DEG C. in presence of a small quantity of air, to give a product suitable for rolling; (5) by warming with methylheptane and sodium wire in presence of a small quantity of air to give a product insoluble in benzene suitable for rolling; (6) by forming an emulsion with sodium oleate solution, and coagulating with acetic acid, the product being worked up to an elastic sheet with aldol-a -naphthylamine, or mixed with carbon black, dicyclohexyl-aminedithiocarbamic dicyclohexylamine, colophony, and the rubber softening agent known under the Registered Trade Mark " Kautschol," and vulcanized without or with sulphur to give strong elastic products; (7) by heating as an emulsion with methyl isopropenyl ketone water, ammonia, oleic acid and hydrogen peroxide, at 30 DEG C. and coagulating with acetic acid; (8) by emulsifying with butadiene, sodium oleate solution, and magnesium oleate, in presence of air and warming at 60 DEG C., followed by treating with acetic acid.ALSO:Elastic, ductile products are obtained by polymerizing 1-chlor-butadiene-1 : 3 in the absence of large amounts of oxygen, for example in presence of nitrogen, hydrogen, or inert gases, at decreased, atmospheric or increased pressure. The process may be carried out at temperatures of from 0-100 DEG C., but preferably at 0-50 DEG C.; accelerating agents such as oxygen, air, alkali metals, their alloys, peroxides such as benzoyl peroxide or hydrogen peroxide, and actinic rays may be employed, or alternatively, agents such as aromatic hydroxy compounds, or amines, or low temperatures. Non-polymerizable solvents or diluents such as dimethyl ether, diethyl ether, hydrocarbons, such as benzene, carbon tetrachloride and other chlorinated hydrocarbons or polymerizable solvents such as butadiene, isoprene, styrene and methylisopropenyl-ketone, or an aqueous medium giving an emulsion may also be employed. When an emulsion of the 1-chlor-butadiene-1 : 3 is employed, stabilizing agents such as wetting or emulsifying agents may be added, with, if desired, accelerators, or retarders and with, for example, natural latex or other emulsions. The products may be obtained soluble, insoluble or capable of swelling, in organic solvents, and may be obtained mixed with fillers, acid binding agents, softening agents, vulcanization accelerators, anti-agers, dyes, or sulphur, added during, before, or after the polymerization. The products may be used as solutions, pastes or emulsions, for impregnating, as coating materials, packings, putties, and as solids, for motor car tyres, conveying bands, packings stable to oil and like technical rubber articles. According to examples, 1-chlor-butadiene-1 : 3 is polymerized (1) by heating in a vacuum at 30 DEG C. and the product worked up with aldol-a -naphthylamine into a sheet; (2) by heating at 25 DEG C. with benzoyl peroxide and toluene, the product being worked up for a coating-mass or by vulcanization; (3) by heating in vacuo with benzoyl peroxide at 60 DEG C. to give an elastic product suitable for rolling; (4) by warming with sodium at 30 DEG C. in presence of a small quantity of air, to give a product suitable for rolling; (5) by warming with methylheptane and sodium wire in presence of a small quantity of air to give a product insoluble in benzene suitable for rolling; (6) by forming an emulsion with sodium oleate solution, and coagulating with acetic acid, the product being worked up to an elastic sheet with aldol-a -naphthylamine, or mixed with carbon black, dicyclohexylaminedithiocarbamic dicyclohexylamine, colophony, and the rubber-softening agent known under the Registered Trade Mark "Kautschol," and vulcanized without or with sulphur to give strong elastic products; (7) by heating as an emulsion with methyl isopropenyl ketone, water, ammonia, oleic acid and hydrogen peroxide, at 30 DEG C. and coagulating with acetic acid; (8) by emulsifying with butadiene, sodium oleate solution and magnesium oleate, in presence of air and warming at 60 DEG C., followed by treating with acetic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI46654D DE608681C (en) | 1933-03-02 | 1933-03-02 | Process for the production of plastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB421146A true GB421146A (en) | 1934-12-14 |
Family
ID=6456169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6445/34A Expired GB421146A (en) | 1933-03-02 | 1934-02-28 | Improvements in the manufacture and production of artificial masses |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE608681C (en) |
| FR (1) | FR769472A (en) |
| GB (1) | GB421146A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE750677C (en) * | 1938-08-02 | 1945-01-22 | Heat-resistant flat seal | |
| DE950031C (en) * | 1943-10-15 | 1956-10-04 | Hoechst Ag | Process for the production of polymers of unsaturated organic compounds |
| US2471456A (en) * | 1946-03-26 | 1949-05-31 | Montclair Res Corp | Wool shrinkproofing baths containing a chloroprene polymer |
| DE1004381B (en) * | 1955-10-13 | 1957-03-14 | Rheinpreussen Ag | Process for the copolymerization of methyl isopropenyl ketone |
| DE1004807B (en) * | 1955-10-13 | 1957-03-21 | Rheinpreussen Ag | Process for the copolymerization of methyl isopropenyl ketone with vinyl compounds |
-
1933
- 1933-03-02 DE DEI46654D patent/DE608681C/en not_active Expired
-
1934
- 1934-02-28 GB GB6445/34A patent/GB421146A/en not_active Expired
- 1934-03-01 FR FR769472D patent/FR769472A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE608681C (en) | 1935-01-29 |
| FR769472A (en) | 1934-08-27 |
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