CA1253292A - Process for producing high molecular weight vinyl copolymers - Google Patents
Process for producing high molecular weight vinyl copolymersInfo
- Publication number
- CA1253292A CA1253292A CA000513862A CA513862A CA1253292A CA 1253292 A CA1253292 A CA 1253292A CA 000513862 A CA000513862 A CA 000513862A CA 513862 A CA513862 A CA 513862A CA 1253292 A CA1253292 A CA 1253292A
- Authority
- CA
- Canada
- Prior art keywords
- monomers
- weight
- vinylpyridine
- polymerization
- polymer
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- 229920006163 vinyl copolymer Polymers 0.000 title abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 37
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 7
- 239000012736 aqueous medium Substances 0.000 claims abstract description 5
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 35
- 239000003999 initiator Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical group NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical group [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000839 emulsion Substances 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000950638 Symphysodon discus Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000167354 Liberibacter crescens Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CAMYKONBWHRPDD-UHFFFAOYSA-N Phenprobamate Chemical compound NC(=O)OCCCC1=CC=CC=C1 CAMYKONBWHRPDD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/759,196 US4593082A (en) | 1985-07-26 | 1985-07-26 | Process for producing high molecular weight vinyl copolymers |
| US759,196 | 1985-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1253292A true CA1253292A (en) | 1989-04-25 |
Family
ID=25054751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000513862A Expired CA1253292A (en) | 1985-07-26 | 1986-07-15 | Process for producing high molecular weight vinyl copolymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4593082A (OSRAM) |
| EP (1) | EP0235177B1 (OSRAM) |
| JP (1) | JPS63500458A (OSRAM) |
| CA (1) | CA1253292A (OSRAM) |
| DE (1) | DE3676188D1 (OSRAM) |
| TR (1) | TR23372A (OSRAM) |
| WO (1) | WO1987000537A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4853461A (en) * | 1988-06-13 | 1989-08-01 | Eastman Kodak Company | Method of isolating copolymers of vinylpyridine and styrene |
| US5149775A (en) * | 1991-01-25 | 1992-09-22 | Eastman Kodak Company | Method for purifying high molecular weight vinylpyridine/styrene polymers from solution |
| US5210149A (en) * | 1992-10-30 | 1993-05-11 | Hoechst Celanese Corporation | Amphoteric copolymer derived from vinylpyridine and acetoxystyrene |
| US5304610A (en) * | 1993-01-12 | 1994-04-19 | Hoechst Celanese Corporation | Amphoteric copolymer derived from vinylpyridine and acetoxystyrene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862902A (en) * | 1953-08-10 | 1958-12-02 | Phillips Petroleum Co | Polymerization of 3-vinylpyridines and latex produced thereby |
| FR2067764A5 (OSRAM) * | 1969-11-15 | 1971-08-20 | Raffinage Cie Francaise |
-
1985
- 1985-07-26 US US06/759,196 patent/US4593082A/en not_active Expired - Fee Related
-
1986
- 1986-07-14 JP JP61503844A patent/JPS63500458A/ja active Granted
- 1986-07-14 WO PCT/US1986/001434 patent/WO1987000537A1/en not_active Ceased
- 1986-07-14 DE DE8686904640T patent/DE3676188D1/de not_active Expired - Fee Related
- 1986-07-14 EP EP86904640A patent/EP0235177B1/en not_active Expired
- 1986-07-15 CA CA000513862A patent/CA1253292A/en not_active Expired
- 1986-07-21 TR TR402/86A patent/TR23372A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR23372A (tr) | 1989-12-28 |
| DE3676188D1 (de) | 1991-01-24 |
| JPS63500458A (ja) | 1988-02-18 |
| JPH0579243B2 (OSRAM) | 1993-11-01 |
| WO1987000537A1 (en) | 1987-01-29 |
| EP0235177A1 (en) | 1987-09-09 |
| EP0235177B1 (en) | 1990-12-12 |
| US4593082A (en) | 1986-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |