GB593036A - Modified olefinic polymers - Google Patents
Modified olefinic polymersInfo
- Publication number
- GB593036A GB593036A GB2998/45A GB299845A GB593036A GB 593036 A GB593036 A GB 593036A GB 2998/45 A GB2998/45 A GB 2998/45A GB 299845 A GB299845 A GB 299845A GB 593036 A GB593036 A GB 593036A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polymer
- specified
- phenol
- chloride
- sulphonyl chloride
- 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 abstract 7
- 150000001336 alkenes Chemical class 0.000 abstract 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 4
- 229920001577 copolymer Polymers 0.000 abstract 3
- 150000002894 organic compounds Chemical class 0.000 abstract 3
- 229920003051 synthetic elastomer Polymers 0.000 abstract 3
- 239000005061 synthetic rubber Substances 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 abstract 2
- -1 ethylene, propylene, butadiene Chemical class 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000005060 rubber Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000004291 sulphur dioxide Substances 0.000 abstract 2
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- 241001608519 Bursera fagaroides Species 0.000 abstract 1
- 239000004859 Copal Substances 0.000 abstract 1
- 235000010919 Copernicia prunifera Nutrition 0.000 abstract 1
- 240000003412 Copernicia prunifera Species 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- 241001553290 Euphorbia antisyphilitica Species 0.000 abstract 1
- 239000004698 Polyethylene (PE) Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- MRMOZBOQVYRSEM-UHFFFAOYSA-N Tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000004429 atoms Chemical group 0.000 abstract 1
- 235000013871 bee wax Nutrition 0.000 abstract 1
- 239000012166 beeswax Substances 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-M carbamodithioate Chemical compound NC([S-])=S DKVNPHBNOWQYFE-UHFFFAOYSA-M 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012170 montan wax Substances 0.000 abstract 1
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 235000019809 paraffin wax Nutrition 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920001084 poly(chloroprene) Polymers 0.000 abstract 1
- 229920000058 polyacrylate Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 150000003343 selenium compounds Chemical class 0.000 abstract 1
- 150000003498 tellurium compounds Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
-
- 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
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/38—Sulfohalogenation
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
An olefin or mixture of olefins having 2-10 C atoms per molecule is polymerized to a product of a molecular weight of 1000 or more and the polymer treated in solution in a chlorine-resisting solvent with a mixture of sulphur dioxide and chlorine in a molar proportion of at least 2 : 1, and the resulting sulphonyl chloride is reacted with an organic compound having an -OH, -SH, -NH2, -CONH2 group or a quinonoid compound. Olefins specified are isobutylene, ethylene, propylene, butadiene alone or with styrene or acrylonitrile; and as solvents carbon tetrachloride, chloroform, ethylene dichloride, carbon disulphide, carbon oxychloride and analogous selenium and tellurium compounds are specified. The sulphochlorination may be carried out under pressure and aided by actinic light or the presence of iodine or lead tetraethyl. The reactive organic compounds specified are ethylene glycol, phenol, aryl or alkyl saturated or unsaturated alcohols, aryl or alkyl mercaptans, dimercaptans and diethylene triamine. In example III, the sulphonyl chloride of a "C4 cut" polymer is reacted with phenol and then treated with formaldehyde and aluminium chloride. Reaction of a sulphonyl chloride with an unsaturated alcohol may be followed by treatment with quinone dioxide, a nitroso compound or a dithiocarbamate. The modified polymers may be used as softeners with natural and synthetic rubbers or compounded with dyes, pigments, copal, beeswax, carnauba, ozokerite, candelilla, japan, montan or paraffin waxes, polyindene, polycoumarone, polyvinyl chloride, polyvinyl acetylene, polyacrylates, cellulose ethers and esters, polystyrene, polyethylene, factice, ester gums, phenol-aldehyde resins and chlorinated rubber. Specification 542,414 is referred to.ALSO:Natural and synthetic rubbers may be softened by compounding therewith a modified olefin polymer obtained by treating a solution of a polymer or copolymer of an olefin having 2-10C. atoms per molecule with sulphur dioxide and chlorine simultaneously in molar ratio of at least 2:1 and reacting the sulphonyl chloride with an organic compound containing an -OH, -SH, -NH2, -CONH2 group, or a quinonoid compound (see Group IV). Synthetic rubbers specified are polychloroprene, isobutylene-butadiene copolymer, and copolymers of butadiene with styrene or acrylonitrile. Chlorinated rubber may also be compounded with the modified polymer.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB593036A true GB593036A (en) | 1947-10-07 |
Family
ID=1627543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2998/45A Expired GB593036A (en) | 1945-02-06 | Modified olefinic polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB593036A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2570094A (en) * | 1950-03-28 | 1951-10-02 | Du Pont | Alkylolamine and morpholine salts of polymerized olefin sulfonic acids |
| US2583370A (en) * | 1947-07-15 | 1952-01-22 | Shell Dev | Method of stabilizing diolefine polymer-sulfur dioxide reaction products |
| US2654680A (en) * | 1948-05-18 | 1953-10-06 | Shell Dev | Method for increasing stability of rubbery polymer reaction products and resulting compositions |
| US3230029A (en) * | 1958-02-21 | 1966-01-18 | Montedison Spa | Process for improving synthetic fibers and the dyeable fibers obtained thereby |
| FR2845090A1 (en) * | 2002-10-01 | 2004-04-02 | Merck Sante Sas | NEW NITROSATION POLYMER IN ORGANIC SYNTHESIS |
-
1945
- 1945-02-06 GB GB2998/45A patent/GB593036A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2583370A (en) * | 1947-07-15 | 1952-01-22 | Shell Dev | Method of stabilizing diolefine polymer-sulfur dioxide reaction products |
| US2654679A (en) * | 1947-07-15 | 1953-10-06 | Shell Dev | Stabilized reaction products of rubbery polymers with inorganic acidifying compounds |
| US2654680A (en) * | 1948-05-18 | 1953-10-06 | Shell Dev | Method for increasing stability of rubbery polymer reaction products and resulting compositions |
| US2570094A (en) * | 1950-03-28 | 1951-10-02 | Du Pont | Alkylolamine and morpholine salts of polymerized olefin sulfonic acids |
| US3230029A (en) * | 1958-02-21 | 1966-01-18 | Montedison Spa | Process for improving synthetic fibers and the dyeable fibers obtained thereby |
| FR2845090A1 (en) * | 2002-10-01 | 2004-04-02 | Merck Sante Sas | NEW NITROSATION POLYMER IN ORGANIC SYNTHESIS |
| WO2004031248A1 (en) * | 2002-10-01 | 2004-04-15 | Merck Patent Gmbh | Novel nitrosation polymer in organic synthesis |
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