DE1271714B - Stabilisieren von gegebenenfalls alkylsubstituierten Vinylpyridinen gegen Verfaerbung - Google Patents
Stabilisieren von gegebenenfalls alkylsubstituierten Vinylpyridinen gegen VerfaerbungInfo
- Publication number
- DE1271714B DE1271714B DEP1271A DE1271714A DE1271714B DE 1271714 B DE1271714 B DE 1271714B DE P1271 A DEP1271 A DE P1271A DE 1271714 A DE1271714 A DE 1271714A DE 1271714 B DE1271714 B DE 1271714B
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- polymerization
- optionally alkyl
- discoloration
- stabilization
- 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.)
- Pending
Links
- 238000002845 discoloration Methods 0.000 title claims description 14
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 title claims description 13
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 11
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000003449 preventive effect Effects 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 18
- 239000000178 monomer Substances 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 11
- 229910017464 nitrogen compound Inorganic materials 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 150000002830 nitrogen compounds Chemical class 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- -1 heterocyclic nitrogen compounds Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 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 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical class C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 description 1
- YQUDMNIUBTXLSX-UHFFFAOYSA-N 2-ethenyl-5-ethylpyridine Chemical compound CCC1=CC=C(C=C)N=C1 YQUDMNIUBTXLSX-UHFFFAOYSA-N 0.000 description 1
- UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 1
- ISRUHSKWYGWJIX-UHFFFAOYSA-N 3-ethenyl-2,4-dimethyl-5,6-dipentylpyridine Chemical compound CCCCCC1=NC(C)=C(C=C)C(C)=C1CCCCC ISRUHSKWYGWJIX-UHFFFAOYSA-N 0.000 description 1
- KNWOTKCKGFQYRP-UHFFFAOYSA-N 3-ethenyl-5-ethylpyridine Chemical compound CCC1=CN=CC(C=C)=C1 KNWOTKCKGFQYRP-UHFFFAOYSA-N 0.000 description 1
- ZVBVBFGGZJJWHR-UHFFFAOYSA-N 4-ethenyl-2,6-diethylpyridine Chemical compound CCC1=CC(C=C)=CC(CC)=N1 ZVBVBFGGZJJWHR-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- NTFOOQDZAMZVJD-UHFFFAOYSA-N 5-ethenyl-4-nonyl-2-propan-2-ylpyridine Chemical compound CCCCCCCCCC1=CC(C(C)C)=NC=C1C=C NTFOOQDZAMZVJD-UHFFFAOYSA-N 0.000 description 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 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F26/00—Homopolymers and 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
- C08F26/06—Homopolymers and 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US221452A US3248363A (en) | 1962-09-05 | 1962-09-05 | Color stabilization of polymerizable heterocyclic nitrogen compounds by formaldehyde |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1271714B true DE1271714B (de) | 1968-07-04 |
Family
ID=22827885
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP1271A Pending DE1271714B (de) | 1962-09-05 | 1963-07-24 | Stabilisieren von gegebenenfalls alkylsubstituierten Vinylpyridinen gegen Verfaerbung |
Country Status (7)
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3060051B2 (ja) * | 1991-04-11 | 2000-07-04 | 塩野香料株式会社 | ピリジン誘導体及び該誘導体を含有する香料組成物 |
WO2006014427A1 (en) * | 2004-07-02 | 2006-02-09 | Advancis Pharmaceutical Corporation | Tablet for pulsed delivery |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2556845A (en) * | 1947-08-21 | 1951-06-12 | Allied Chem & Dye Corp | Production of vinyl pyridine compounds |
US2732376A (en) * | 1956-01-24 | wagner | ||
US2754300A (en) * | 1953-07-24 | 1956-07-10 | Celanese Corp | Production of substituted pyridines |
US2878205A (en) * | 1956-05-23 | 1959-03-17 | Chemstrand Corp | Acrylonitrile polymer composition stabilized with formaldehyde, a substituted phenol, and acetic anhydride, and method of making same |
US2887490A (en) * | 1952-08-05 | 1959-05-19 | Phillips Petroleum Co | Color stabilization of polymerizable heterocyclic nitrogen compounds |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE552299A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-11-16 | |||
NL273600A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1956-05-23 | |||
US2878213A (en) * | 1956-05-23 | 1959-03-17 | Chemstrand Corp | Acrylonitrile polymer composition stabilized with formaldehyde, zinc dicetyldithiophosphate, and an inorganic acid and method of making same |
US2878227A (en) * | 1956-12-17 | 1959-03-17 | Chemstrand Corp | Acrylonitrile polymer compositions stabilized with paraformaldehyde and trialkyl subsituted phosphites, and method of making same |
US2962476A (en) * | 1956-11-30 | 1960-11-29 | Gen Aniline & Film Corp | Polymerized alkyl vinyl ethers of improved stability |
US2980642A (en) * | 1958-01-16 | 1961-04-18 | Armstrong Cork Co | Color stable lacquer comprising vinyl chloride resin and 1, 3-butylene adipate |
-
0
- NL NL296510D patent/NL296510A/xx unknown
- NL NL123741D patent/NL123741C/xx active
- NL NL221452D patent/NL221452A/xx unknown
- BE BE635537D patent/BE635537A/xx unknown
-
1962
- 1962-09-05 US US221452A patent/US3248363A/en not_active Expired - Lifetime
-
1963
- 1963-06-26 GB GB25342/63A patent/GB967156A/en not_active Expired
- 1963-07-19 FR FR942116A patent/FR1363794A/fr not_active Expired
- 1963-07-24 DE DEP1271A patent/DE1271714B/de active Pending
- 1963-07-31 LU LU44177D patent/LU44177A1/xx unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2732376A (en) * | 1956-01-24 | wagner | ||
US2556845A (en) * | 1947-08-21 | 1951-06-12 | Allied Chem & Dye Corp | Production of vinyl pyridine compounds |
US2887490A (en) * | 1952-08-05 | 1959-05-19 | Phillips Petroleum Co | Color stabilization of polymerizable heterocyclic nitrogen compounds |
US2754300A (en) * | 1953-07-24 | 1956-07-10 | Celanese Corp | Production of substituted pyridines |
US2878205A (en) * | 1956-05-23 | 1959-03-17 | Chemstrand Corp | Acrylonitrile polymer composition stabilized with formaldehyde, a substituted phenol, and acetic anhydride, and method of making same |
Also Published As
Publication number | Publication date |
---|---|
BE635537A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
GB967156A (en) | 1964-08-19 |
LU44177A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-02-01 |
NL221452A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
US3248363A (en) | 1966-04-26 |
NL123741C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
FR1363794A (fr) | 1964-06-12 |
NL296510A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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