FR2491480A1 - Nouvelles associations de derives b-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des resines vinyliques - Google Patents
Nouvelles associations de derives b-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des resines vinyliques Download PDFInfo
- Publication number
- FR2491480A1 FR2491480A1 FR8021243A FR8021243A FR2491480A1 FR 2491480 A1 FR2491480 A1 FR 2491480A1 FR 8021243 A FR8021243 A FR 8021243A FR 8021243 A FR8021243 A FR 8021243A FR 2491480 A1 FR2491480 A1 FR 2491480A1
- Authority
- FR
- France
- Prior art keywords
- vinyl
- resin
- parts
- radical
- carbon atoms
- 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.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 57
- 229920005989 resin Polymers 0.000 title claims abstract description 57
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 26
- 230000006641 stabilisation Effects 0.000 title claims abstract description 17
- 238000011105 stabilization Methods 0.000 title claims abstract description 17
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 15
- 239000003381 stabilizer Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 21
- 235000013305 food Nutrition 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 15
- 239000004800 polyvinyl chloride Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- -1 alkyl radical Chemical class 0.000 claims description 13
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical compound C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 claims description 5
- 229920006163 vinyl copolymer Polymers 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 2
- 229950006389 thiodiglycol Drugs 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical group CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- UKVYVZLTGQVOPX-NSCUHMNNSA-N (e)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C/C(O)=O UKVYVZLTGQVOPX-NSCUHMNNSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
- 239000008116 calcium stearate Substances 0.000 description 5
- 235000013539 calcium stearate Nutrition 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000003490 calendering Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003017 thermal stabilizer Substances 0.000 description 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 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101150055917 BRE1 gene Proteins 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 240000005589 Calophyllum inophyllum Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 101100219037 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) upl-1 gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SPBMMWPWMPIQPR-UHFFFAOYSA-L calcium;zinc;octadecanoate Chemical compound [Ca+2].[Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SPBMMWPWMPIQPR-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 1
- DYYYPIJLRRHUPR-UHFFFAOYSA-N dimethyl 1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=CNC=C(C(=O)OC)C1 DYYYPIJLRRHUPR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010101 extrusion blow moulding Methods 0.000 description 1
- 235000003086 food stabiliser Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021243A FR2491480A1 (fr) | 1980-10-03 | 1980-10-03 | Nouvelles associations de derives b-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des resines vinyliques |
| US06/307,298 US4388430A (en) | 1980-10-03 | 1981-09-30 | Associations for stabilizing vinyl resins |
| AT0422481A ATA422481A (de) | 1980-10-03 | 1981-10-01 | Neue stabilisatormischung fuer vinylharze |
| EP81870039A EP0049699A1 (fr) | 1980-10-03 | 1981-10-02 | Nouvelles associations de dérivés bêta-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des résines vinyliques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021243A FR2491480A1 (fr) | 1980-10-03 | 1980-10-03 | Nouvelles associations de derives b-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des resines vinyliques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2491480A1 true FR2491480A1 (fr) | 1982-04-09 |
| FR2491480B1 FR2491480B1 (OSRAM) | 1982-12-31 |
Family
ID=9246541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8021243A Granted FR2491480A1 (fr) | 1980-10-03 | 1980-10-03 | Nouvelles associations de derives b-aminocrotoniques et de dihydropyridines utiles pour la stabilisation des resines vinyliques |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4388430A (OSRAM) |
| EP (1) | EP0049699A1 (OSRAM) |
| AT (1) | ATA422481A (OSRAM) |
| FR (1) | FR2491480A1 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808642A (en) * | 1985-04-26 | 1989-02-28 | Takiron Co., Ltd. | Chlorine-containing resin molding and material for use therewith |
| DE10109366A1 (de) * | 2001-02-27 | 2002-09-12 | Baerlocher Gmbh | Stabilisatorzusammensetzung für halogenierte Polymere, deren Verwendung, und solche Zusammensetzungen enthaltende Polymere |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3249584A (en) * | 1961-02-15 | 1966-05-03 | Montedison Spa | Polyvinylchloride stabilized with urea and butyl amino crotonate |
| FR2405974A1 (fr) * | 1977-10-14 | 1979-05-11 | Labaz | Nouveau procede de stabilisation a la lumiere de resines de chlorure de polyvinyle |
| EP0002007A1 (de) * | 1977-11-11 | 1979-05-30 | Ciba-Geigy Ag | Neue Pyridindicarbonsäureesterderivate und ihre Gemische mit metallhaltigen Stabilisatoren sowie ihre Verwendung zur Stabilisierung von chlorhaltigen Thermoplasten |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1544768B2 (de) * | 1964-12-02 | 1970-09-10 | Deutsche Advance Produktion GmbH, 6141 Lautern | Stabilisieren von Vinylchloridpolymerxsaten |
| DE1803787B2 (de) * | 1968-10-18 | 1973-09-06 | Chemische Werke Hüls AG, 4370 Mari | Polyvinylchlorid-mischung zur herstellung antistatischer hohlkoerper und blasfolien |
| FR2405937A1 (fr) * | 1977-10-14 | 1979-05-11 | Labaz | Nouveaux derives de dihydropyridine, leur procede de preparation et leur application |
| DE2844130A1 (de) * | 1977-10-14 | 1979-04-26 | Labaz | Neue dihydropyridine und deren verwendung |
| FR2407236A1 (fr) * | 1977-10-28 | 1979-05-25 | Labaz | Nouvelle association stabilisante pour resines vinyliques |
-
1980
- 1980-10-03 FR FR8021243A patent/FR2491480A1/fr active Granted
-
1981
- 1981-09-30 US US06/307,298 patent/US4388430A/en not_active Expired - Fee Related
- 1981-10-01 AT AT0422481A patent/ATA422481A/de unknown
- 1981-10-02 EP EP81870039A patent/EP0049699A1/fr not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3249584A (en) * | 1961-02-15 | 1966-05-03 | Montedison Spa | Polyvinylchloride stabilized with urea and butyl amino crotonate |
| FR2405974A1 (fr) * | 1977-10-14 | 1979-05-11 | Labaz | Nouveau procede de stabilisation a la lumiere de resines de chlorure de polyvinyle |
| EP0002007A1 (de) * | 1977-11-11 | 1979-05-30 | Ciba-Geigy Ag | Neue Pyridindicarbonsäureesterderivate und ihre Gemische mit metallhaltigen Stabilisatoren sowie ihre Verwendung zur Stabilisierung von chlorhaltigen Thermoplasten |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0049699A1 (fr) | 1982-04-14 |
| US4388430A (en) | 1983-06-14 |
| FR2491480B1 (OSRAM) | 1982-12-31 |
| ATA422481A (de) | 1984-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CA | Change of address | ||
| CD | Change of name or company name | ||
| ST | Notification of lapse |