GB696066A - Polymers - Google Patents
PolymersInfo
- Publication number
- GB696066A GB696066A GB661350A GB661350A GB696066A GB 696066 A GB696066 A GB 696066A GB 661350 A GB661350 A GB 661350A GB 661350 A GB661350 A GB 661350A GB 696066 A GB696066 A GB 696066A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylonitrile
- copolymers
- polymerization
- acid esters
- acetone
- 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 2
- -1 peroxy compound Chemical class 0.000 abstract 7
- 229920001577 copolymer Polymers 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000007792 addition Methods 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000004816 latex Substances 0.000 abstract 3
- 229920000126 latex Polymers 0.000 abstract 3
- 238000006116 polymerization reaction Methods 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000011877 solvent mixture Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004160 Ammonium persulphate Substances 0.000 abstract 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical class CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 abstract 1
- 229920000459 Nitrile rubber Polymers 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019395 ammonium persulphate Nutrition 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical class CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 abstract 1
- 150000004680 hydrogen peroxides Chemical class 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- UHOGYFJGPNJUTQ-UHFFFAOYSA-M sodium;octadecan-2-yl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCC(C)OS([O-])(=O)=O UHOGYFJGPNJUTQ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- 229950011008 tetrachloroethylene Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene 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
- 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
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)
Abstract
An acetone-soluble film-forming copolymer of methacrylonitrile and vinylidene chloride alone which contains 55 to 99 per cent of methacrylonitrile is preferably prepared in an aqueous suspension or dispersion containing methacrylonitrile and vinylidene chloride in a ratio between 52.5 : 47.5 and 90 : 10, the ratio of water to total monomer being from 3 : 1 to 6 : 1, polymerization being initiated by means of a peroxy compound. The emulsifying agent used is preferably sodium secondary octadecyl sulphate, other suitable emulsifying agents being alkali metal or ammonium salts of other long-chain alkyl sulphates, of aralkyl sulphates, of alkyl-aryl sulphonic acids or of long-chain alkyl carboxylic acids. The catalyst is preferably potassium or ammonium persulphate, other suitable catalysts being benzoyl, acetyl, lauryl and hydrogen peroxides and tertiary butyl hydroperoxide. Redox system may be employed using oxygen or one of the above catalysts in conjunction with a reducing agent such as sodium sulphinate or a sugar. Regulators such as dodecyl mercaptan, acetaldehyde and dioxane may be used to control the average molecular weight of the polymer, and polymerization may be stopped by addition of an anti-oxidant such as phenyl-beta-naphthylamine. Additions of methacrylonitrile may be made in the course of polymerization so as to keep the monomer ratio constant throughout. The copolymer may be recovered from the aqueous latex by addition of an aqueous solution containing ions capable of neutralizing the charge on the latex particles, by freezing the p latex, or by the use of a water-soluble organic precipitant such as methanol or ethanol. The copolymers of the invention may be plasticized with dialkyl and alkoxyalkyl phthalates, glycolic acid esters, dicarboxylic acid esters of cyclohexanol and its derivatives, sebacic and phosphoric acid esters, butadiene-acrylonitrile copolymers and low molecular weight condensation products of glycols with aliphatic dicarboxylic acids. Films and filaments may be made from acetone solutions of the copolymers and may be dyed by the methods used in dyeing cellulose acetate fibres. They may be stretched to many times their original length and annealed, e.g. at a temperature above 60 DEG C. Coating compositions may be made by dissolving the copolymers in volatile solvents or solvent mixtures such as one or more of acetone, methyl ethyl ketone, dioxane, dioxolane, tetrahydrofurane, nitromethane and nitroethane or in less volatile solvents such as cyclohexanone, cyclopentanone, isophorone, mesityl oxide and pyridine, and diluents such as benzene, toluene or a xylene may be added. Solvent mixtures may also include ethyl acetate, ethyl and butyl lactates, diethyl, methyl isobutyl, and methyl amyl ketones, diacetone alcohol, methylene and ethylene dichlorides, trichlorethylene, carbon tetrachloride, perchlorethylene and monochlorbenzene. Specifications 569,182, 570,711 and 629,137 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB661350A GB696066A (en) | 1950-03-16 | 1950-03-16 | Polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB661350A GB696066A (en) | 1950-03-16 | 1950-03-16 | Polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB696066A true GB696066A (en) | 1953-08-26 |
Family
ID=9817651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB661350A Expired GB696066A (en) | 1950-03-16 | 1950-03-16 | Polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB696066A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048955A (en) * | 1999-02-02 | 2000-04-11 | Solutia Inc. | Modacrylic copolymer composition |
-
1950
- 1950-03-16 GB GB661350A patent/GB696066A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048955A (en) * | 1999-02-02 | 2000-04-11 | Solutia Inc. | Modacrylic copolymer composition |
| WO2000046261A1 (en) * | 1999-02-02 | 2000-08-10 | Solutia Inc. | Modacrylic copolymer composition |
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