GB600317A - Improved process for the low temperature polymerisation of olefinic materials - Google Patents
Improved process for the low temperature polymerisation of olefinic materialsInfo
- Publication number
- GB600317A GB600317A GB2247844A GB2247844A GB600317A GB 600317 A GB600317 A GB 600317A GB 2247844 A GB2247844 A GB 2247844A GB 2247844 A GB2247844 A GB 2247844A GB 600317 A GB600317 A GB 600317A
- Authority
- GB
- United Kingdom
- Prior art keywords
- specified
- methyl
- acid
- organic
- butene
- 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
- -1 chloracetic acid Chemical class 0.000 abstract 3
- 239000003607 modifier Substances 0.000 abstract 3
- 229920000098 polyolefin Polymers 0.000 abstract 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 150000002826 nitrites Chemical class 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 1
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 abstract 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 abstract 1
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methylpent-1-ene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-Chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N Cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 1
- 229940094941 ISOAMYL BUTYRATE Drugs 0.000 abstract 1
- UAHWPYUMFXYFJY-UHFFFAOYSA-N Myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N Piperylene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N Pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N Thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N Tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 229930006719 beta-myrcene Natural products 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N cyanoguanidine Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229940073769 methyl oleate Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- MOQRZWSWPNIGMP-UHFFFAOYSA-N pentyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCC MOQRZWSWPNIGMP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000737 periodic Effects 0.000 abstract 1
- 150000003346 selenoethers Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- 229960002447 thiram Drugs 0.000 abstract 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011787 zinc oxide 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
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)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Mixtures of a major proportion of a pure isoolefin with minor proportions of a pure polyolefin are polymerized at -40 DEG to -165 DEG C. by the use of a solid or liquid Friedel-Crafts catalyst in a low-freezing inert solvent in the presence of from 0.001 to 15 per cent by weight of an organic modifying agent selected from one or more of the following classes, viz. hydrocarbons having a non-metallic substituent selected from Groups V and VI of the Periodic Table with or without halogen, C4 and higher normal olefins, C5 and higher isoolefins and aromatic hydrocarbons. Specified isoolefins are isobutylene, 2-methyl-butene-1 and 2-methyl-pentene-1 and specified polyolefins p are butadiene, isoprene, piperylene, dimethyl butadiene, myrcene and dimethallyl, the preferred polyolefins having from 4 to 14 carbon atoms per molecule. Specified groups of modifiers are the hydrocarbons, alcohols, ketones, organic acids and their esters, thioacids are their esters, amides, amines, nitrites, organic sulphides and mercaptans, ethers, sulphoxides, sulphones, sulphonates, organic sulphates, acid halides, acid anhydrides, nitro compounds, nitroso compounds, nitrates, nitrites, hydroxylamines, selenides, substituted alcohols of the type of ethylene chlorohydrin, substituted acids such as chloracetic acid, substituted phenols such as meta - chlorophenol, dicyandiamide, metallic alcoholates, sulphonamides, phenols, ureas, cyclic dinitrogen compounds such as pyrimidine and pyrazoline and acetylene. Particularly preferred modifiers are diisobutylene, ethyl ether, butene-1, butene-2, benzene, xylene, toluene, cumene, naphthalene, methyl alcohol, methyl oleate, acetaldehyde, isoamyl butyrate, amyl stearate, dodecyl mercaptan, tributylamine, Lorolamine, trimethylamine, oleic acid, sulphur dioxide, acetone and trimethylethylene. Long lists of specified modifiers are given. The products may be compounded with carbon black, stearic acid, zinc oxide, tetramethyl thiuramdisulphide, and sulphur. Specifications 525,542, 560,924, 577,350 and 589,393 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB600317A true GB600317A (en) | 1948-04-06 |
Family
ID=1736987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2247844A Expired GB600317A (en) | 1944-11-14 | Improved process for the low temperature polymerisation of olefinic materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB600317A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995017436A1 (en) * | 1993-12-23 | 1995-06-29 | University Of Massachusetts Lowell | Initiation via haloboration in living cationic polymerization |
| EP1426387A2 (en) * | 2002-12-05 | 2004-06-09 | Bayer Aktiengesellschaft | Process for production of high-isoprene butyl rubber |
-
1944
- 1944-11-14 GB GB2247844A patent/GB600317A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995017436A1 (en) * | 1993-12-23 | 1995-06-29 | University Of Massachusetts Lowell | Initiation via haloboration in living cationic polymerization |
| US5665837A (en) * | 1993-12-23 | 1997-09-09 | University Of Massachusetts Lowell | Initiation via haloboration in living cationic polymerization |
| EP1426387A2 (en) * | 2002-12-05 | 2004-06-09 | Bayer Aktiengesellschaft | Process for production of high-isoprene butyl rubber |
| EP1426387A3 (en) * | 2002-12-05 | 2004-07-21 | Bayer Aktiengesellschaft | Process for production of high-isoprene butyl rubber |
| US7256244B2 (en) | 2002-12-05 | 2007-08-14 | Lanxess Inc. | Process for production of high-isoprene butyl rubber |
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