GB934469A - Stereoregular polymers of alpha-substituted acrylonitriles - Google Patents
Stereoregular polymers of alpha-substituted acrylonitrilesInfo
- Publication number
- GB934469A GB934469A GB819862A GB819862A GB934469A GB 934469 A GB934469 A GB 934469A GB 819862 A GB819862 A GB 819862A GB 819862 A GB819862 A GB 819862A GB 934469 A GB934469 A GB 934469A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alpha
- polymers
- group
- catalyst
- acrolein
- 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
- 239000003054 catalyst Substances 0.000 abstract 4
- 229920000642 polymer Polymers 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910052790 beryllium Inorganic materials 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 2
- YSGPDJCRZNUFBU-UHFFFAOYSA-N 2-methylidenepentanenitrile Chemical compound CCCC(=C)C#N YSGPDJCRZNUFBU-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 150000008360 acrylonitriles Chemical class 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 abstract 1
- ANYNYRPVUUZMGG-UHFFFAOYSA-N bromobenzene;magnesium Chemical compound [Mg].BrC1=CC=CC=C1 ANYNYRPVUUZMGG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 abstract 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000008098 formaldehyde solution Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229920006158 high molecular weight polymer Polymers 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 150000002642 lithium compounds Chemical class 0.000 abstract 1
- -1 lithium n-butyl Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- IASJILDAHOUCFO-UHFFFAOYSA-N n-hex-1-en-3-ylidenehydroxylamine Chemical compound CCCC(C=C)=NO IASJILDAHOUCFO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000004065 semiconductor Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/42—Nitriles
- C08F20/50—Nitriles containing four or more carbon atoms
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Artificial Filaments (AREA)
Abstract
Linear, head to tail, high molecular weight polymers of monomers of alpha-substituted acrylonitriles having the general formula <FORM:0934469/IV(a)/1> where is a linear aliphatic group containing at least two carbon atoms or a branched aliphatic or cycloaliphatic group are prepared using as catalyst a metal organic compound of the general formula MR1aR11bHac where M is a Group Ia, II or III metal of the Mendel<\>aeeff Periodic Table; R1 and R11 are the same or different alkyl, aryl or cycloalkyl groups; Ha is a halogen; a is 0, 1, 2 or 3, b is 1, 2 or 3 and c is 0, 1 or 2 and is zero when M is a Group Ia metal; a+b+c corresponds to the valency of M. The preferred catalysts are the magnesium, beryllium and lithium compounds, e.g. lithium n-butyl, magnesium phenyl bromide and beryllium diethyl. The monomer/catalyst molar ratios are usually between 10 : 1 and 200 : 1. The polymerization is preferably carried out in an inert solvent which does not react or form complexes with the catalyst, e.g. aliphatic or aromatic hydrocarbons such as toluene and benzene. Complex forming solvents cannot be used. The examples describe the preparation of polymers of a -ethylacrylonitrile, a -n-propylacrylonitrile and a -isopropylacrylonitrile. The polymers may be saponified and then acidified to yield polyacids which may be used in ion-exchangers. On heating the polymers to a few degrees below the melting temperature, cyclization through the nitrile groups which are transformed into a system of conjugated groups of the type =N-C-N-C=N-, occurs, giving the polymers the properties of oriented semiconductors.ALSO:Alpha-n-propyl acrolein is prepared by reacting together under reflux n-valeraldehyde, dimethylamine hydrochloride and a 40% formaldehyde solution. The oxime is formed by treatment of the acrolein with hydroxylamine hydrochloride. Alpha-n-propyl acrylonitrile is then formed by reacting the alpha-n-propyl acrolein oxime with acetic anhydride in the presence of hydroquinone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT423561 | 1961-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB934469A true GB934469A (en) | 1963-08-21 |
Family
ID=11112469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB819862A Expired GB934469A (en) | 1961-03-07 | 1962-03-02 | Stereoregular polymers of alpha-substituted acrylonitriles |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1172430B (en) |
| GB (1) | GB934469A (en) |
| NL (1) | NL275563A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017066131A (en) * | 2015-09-30 | 2017-04-06 | 富士フイルム株式会社 | METHOD FOR PRODUCING Aromatic COMPOUND |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB843611A (en) * | 1957-11-22 | 1960-08-04 | Ici Ltd | Polymerisation process |
-
0
- NL NL275563D patent/NL275563A/xx unknown
-
1962
- 1962-03-02 GB GB819862A patent/GB934469A/en not_active Expired
- 1962-03-05 DE DEM52014A patent/DE1172430B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017066131A (en) * | 2015-09-30 | 2017-04-06 | 富士フイルム株式会社 | METHOD FOR PRODUCING Aromatic COMPOUND |
| EP3357914A4 (en) * | 2015-09-30 | 2018-08-08 | FUJIFILM Corporation | Aromatic compound production method |
| US10323005B2 (en) | 2015-09-30 | 2019-06-18 | Fujifilm Corporation | Aromatic compound production method |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1172430B (en) | 1964-06-18 |
| NL275563A (en) |
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