NL8100835A - Pyrrolidine-ring-bevattende samenstelling voor toepassing als anti-ultravioletstabilisator in kunststofmaterialen. - Google Patents

Pyrrolidine-ring-bevattende samenstelling voor toepassing als anti-ultravioletstabilisator in kunststofmaterialen. Download PDF

Info

Publication number: NL8100835A
Authority: NL; Netherlands
Prior art keywords: ultraviolet; ultraviolet stabilizer; plastic materials; polyolefin polymers; acid ester
Prior art date: 1980-02-19

Application number

NL8100835A

Other languages

English (en)

Dutch (nl)

Original Assignee

Anic Spa

Priority date (The priority date 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 date listed.)

1980-02-19

Filing date

1981-02-19

Publication date

1981-09-16

1981-02-19 Application filed by Anic Spa filed Critical Anic Spa

1981-09-16 Publication of NL8100835A publication Critical patent/NL8100835A/nl

Links

239000000326 ultraviolet stabilizing agent Substances 0.000 title claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 9
239000000203 mixture Substances 0.000 title claims description 8
239000000463 material Substances 0.000 title description 3
239000004033 plastic Substances 0.000 title description 3
229920003023 plastic Polymers 0.000 title description 3
-1 straight chain fatty acid ester Chemical class 0.000 claims description 21
229920000642 polymer Polymers 0.000 claims description 11
229920000098 polyolefin Polymers 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
230000002411 adverse Effects 0.000 claims 1
230000002939 deleterious effect Effects 0.000 claims 1
229940070765 laurate Drugs 0.000 claims 1
239000004743 Polypropylene Substances 0.000 description 10
229920001155 polypropylene Polymers 0.000 description 10
239000003381 stabilizer Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
235000021314 Palmitic acid Nutrition 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
229940024874 benzophenone Drugs 0.000 description 3
230000006866 deterioration Effects 0.000 description 3
MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 3
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
NOXHNAYUTJEYNN-UHFFFAOYSA-N 2,2,3,4,5,5-hexamethylpyrrolidine Chemical compound CC1C(C)C(C)(C)NC1(C)C NOXHNAYUTJEYNN-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000005639 Lauric acid Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
AAEJQHLAJICLHR-UHFFFAOYSA-N 1,2,2,3,3,4-hexamethylpyrrolidine Chemical compound CC1CN(C)C(C)(C)C1(C)C AAEJQHLAJICLHR-UHFFFAOYSA-N 0.000 description 1
HICQVZTYLBJIIY-UHFFFAOYSA-N 2-(2,2,3,3,4,4-hexamethylpyrrolidin-1-yl)ethanol Chemical compound CC1(C)CN(CCO)C(C)(C)C1(C)C HICQVZTYLBJIIY-UHFFFAOYSA-N 0.000 description 1
ZFMPCFWNBXALCU-UHFFFAOYSA-N 2-(2,2,3,4,5,5-hexamethylpyrrolidin-1-yl)ethanol Chemical compound CC1C(C)C(C)(C)N(CCO)C1(C)C ZFMPCFWNBXALCU-UHFFFAOYSA-N 0.000 description 1
OCAQNEYBPDEIGD-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)OCC.CC1C(C(N(C1)C)(C)C)(C)C Chemical compound C(CCCCCCCCCCC)(=O)OCC.CC1C(C(N(C1)C)(C)C)(C)C OCAQNEYBPDEIGD-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000000368 destabilizing effect Effects 0.000 description 1
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
LDOZSADIRVDPKA-UHFFFAOYSA-N ethyl hexadecanoate 1,2,2,3,3,4-hexamethylpyrrolidine Chemical compound C(CCCCCCCCCCCCCCC)(=O)OCC.CC1C(C(N(C1)C)(C)C)(C)C LDOZSADIRVDPKA-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
230000001788 irregular Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002942 palmitic acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010998 test method Methods 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- C08K5/3415—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cosmetics (AREA)

NL8100835A 1980-02-19 1981-02-19 Pyrrolidine-ring-bevattende samenstelling voor toepassing als anti-ultravioletstabilisator in kunststofmaterialen. NL8100835A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2000180		1980-02-19
IT20001/80A IT1174663B (it)	1980-02-19	1980-02-19	Composizioni pirrolidiniche e loro uso quali stabilizzanti uv per materie plastiche

Publications (1)

Publication Number	Publication Date
NL8100835A true NL8100835A (nl)	1981-09-16

Family

ID=11162984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100835A NL8100835A (nl)	1980-02-19	1981-02-19	Pyrrolidine-ring-bevattende samenstelling voor toepassing als anti-ultravioletstabilisator in kunststofmaterialen.

Country Status (14)

Country	Link
US (1)	US4325864A (fr)
JP (1)	JPS56131644A (fr)
BE (1)	BE887565A (fr)
CH (1)	CH652730A5 (fr)
DE (1)	DE3106217C2 (fr)
DK (1)	DK56081A (fr)
FR (1)	FR2476105A1 (fr)
GB (2)	GB2069507B (fr)
IE (1)	IE50926B1 (fr)
IT (1)	IT1174663B (fr)
LU (1)	LU83146A1 (fr)
NL (1)	NL8100835A (fr)
NO (1)	NO810527L (fr)
SE (1)	SE8100746L (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1196327B (it) *	1984-11-16	1988-11-16	Consiglio Nazionale Ricerche	3-aza-7-idrossi-2,2,4,4-tetraalchilbiciclo (3.3.0) ottani,procedimento per la loro preparazione,intermedi adatti allo scopo e procedimento per l'ottenimento di questi ultimi
US5350786A (en) *	1986-06-30	1994-09-27	Enichem Synthesis S.P.A.	Process of (co)polymerization of α-olefins in the presence of stabilizers

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE923915C (de) *	1951-05-05	1955-02-24	Upjohn Co	Verfahren zur Herstellung von spasmolytisch wirksamen Pyrrolidinverbindungen
GB1398414A (en) *	1972-07-28	1975-06-18	Ciba Geigy Ag	Piperidine derivatives
GB1437002A (en) *	1972-09-13	1976-05-26	Ici Ltd	Cyclic amines
DE2459331A1 (de) *	1973-12-28	1975-07-10	Ciba Geigy Ag	Pyrrolidin-dicarbonsaeuren und ihre ester als lichtstabilisatoren
GB1467672A (en) *	1974-04-11	1977-03-16	Ciba Geigy Ag	Stabilised epoxy resin
US4093586A (en) *	1975-01-15	1978-06-06	Ciba-Geigy Corporation	Pyrrolidine dicarboxylic acids and esters and stabilized compositions
US4111901A (en) *	1977-06-06	1978-09-05	Borg-Warner Corporation	Hindered five-membered nitrogen rings as polyolefin stabilizers
IT1160064B (it) *	1978-11-10	1987-03-04	Anic Spa	Procedimento per la stabilizzazione di polimeri mediante impiego di sali di nichel di pirrolidinditiocarbammati sostituiti

1980
- 1980-02-19 IT IT20001/80A patent/IT1174663B/it active
- 1980-12-05 US US06/213,653 patent/US4325864A/en not_active Expired - Lifetime
1981
- 1981-01-30 SE SE8100746A patent/SE8100746L/xx not_active Application Discontinuation
- 1981-02-04 GB GB8103466A patent/GB2069507B/en not_active Expired
- 1981-02-10 DK DK56081A patent/DK56081A/da not_active Application Discontinuation
- 1981-02-16 CH CH1015/81A patent/CH652730A5/it not_active IP Right Cessation
- 1981-02-17 FR FR8103117A patent/FR2476105A1/fr active Granted
- 1981-02-17 NO NO810527A patent/NO810527L/no unknown
- 1981-02-18 IE IE322/81A patent/IE50926B1/en unknown
- 1981-02-18 BE BE0/203829A patent/BE887565A/fr not_active IP Right Cessation
- 1981-02-18 LU LU83146A patent/LU83146A1/fr unknown
- 1981-02-18 JP JP2162481A patent/JPS56131644A/ja active Pending
- 1981-02-19 DE DE3106217A patent/DE3106217C2/de not_active Expired
- 1981-02-19 NL NL8100835A patent/NL8100835A/nl not_active Application Discontinuation
1983
- 1983-06-20 GB GB08316728A patent/GB2129813B/en not_active Expired

Also Published As

Publication number	Publication date
FR2476105B1 (fr)	1984-02-24
GB2129813B (en)	1984-11-21
US4325864A (en)	1982-04-20
GB2069507B (en)	1984-02-08
FR2476105A1 (fr)	1981-08-21
SE8100746L (sv)	1981-08-20
IT8020001A0 (it)	1980-02-19
GB8316728D0 (en)	1983-07-20
GB2069507A (en)	1981-08-26
NO810527L (no)	1981-08-20
BE887565A (fr)	1981-08-18
IT1174663B (it)	1987-07-01
CH652730A5 (it)	1985-11-29
IE810322L (en)	1981-08-19
IE50926B1 (en)	1986-08-20
JPS56131644A (en)	1981-10-15
DE3106217C2 (de)	1985-03-28
LU83146A1 (fr)	1981-09-11
DE3106217A1 (de)	1982-01-21
DK56081A (da)	1981-08-20
GB2129813A (en)	1984-05-23

Legal Events

Date	Code	Title
1983-09-01	BA	A request for search or an international-type search has been filed
1983-10-03	BB	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1987-10-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0323409B1 (fr)	1996-01-03	Compositions de polyoléfines stabilisées à l'aide de N,N-dialkylhydroxylamines à longue chaîne
DE69806696T2 (de)	2003-04-03	N,N',N''-Tris(2,4-Bis(1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl)alkylamino)-s-triazin-6-yl)-3,3'-ethylenediiminodipropylamine, ihre Isomere und überbrückte Derivate, sowie damit stabilisierte Polymerzusammensetzungen
HK1004563B (en)	1998-11-27	Polyolefin compositions stabilized with long chain n,n-dialkylhydroxylamines
US3850877A (en)	1974-11-26	Piperidine stabilizers for polymers
JP5666429B2 (ja)	2015-02-12	エチレン性不飽和酸またはそのエステルの製造
EP0727410A1 (fr)	1996-08-21	Dérivés esters du bisphénol
DE2512895A1 (de)	1975-10-02	Phenolester und phenolamide
US4093586A (en)	1978-06-06	Pyrrolidine dicarboxylic acids and esters and stabilized compositions
JPH09510485A (ja)	1997-10-21	Ｈｄｐｅの安定化方法
EP0716076A2 (fr)	1996-06-12	Dérivés bisphénol ester
FR2476104A1 (fr)	1981-08-21	Compositions de polyolefine stabilisees contre la radiation ultraviolette avec des amines a chaine ouverte, comportant un encombrement sterique
NL8100834A (nl)	1981-09-16	Met pyrrolidinederivaten tegen ultravioletstraling gestabiliseerde polyalkeensamenstellingen.
DE1593750A1 (de)	1970-12-10	Substituierte Benzophenone als Lichtstabilisatoren
WO1997007159A1 (fr)	1997-02-27	Utilisation de composes de piperidine
US4325864A (en)	1982-04-20	Pyrrolidine-ring-containing compositions for use as anti-UV stabilizers in plastics materials
DE3629703C2 (de)	1996-10-02	5-Höheralkylsubstituierte 2H-Benztriazole und stabilisierte Zusammensetzungen
US3883477A (en)	1975-05-13	Compositions stabilized with 1,4-disubstituted-7-azabicyclo (2.2.1) heptane-2,5 or 2, 6-dicarboxylic acid esters
DE2254476A1 (de)	1973-05-17	Nickel-komplexe von 2-(2'-hydroxyphenyl)-v-triazolen
IE50927B1 (en)	1986-08-20	Polymers containing pyrrolidine-ring-containing compounds as stabilizers against uv-radiation;and method of stabilizing polymers
JPS61254641A (ja)	1986-11-12	紫外線吸収剤
DE2337822A1 (de)	1974-02-07	Piperidinderivate
EP0761698A2 (fr)	1997-03-12	Procédé de préparation de polymères à base de monomères vinyliques basiques
RU2100360C1 (ru)	1997-12-27	Продукты олигомеризации 10-пропенилфенотиазина в качестве стабилизаторов для полиолефинов
DE2446996C3 (de)	1977-04-28	Azo-bis-1,3-dloxane und deren Verwendung als Photoinitiator für die Polymerisation von Vinylmonomeren
DE2109703A1 (de)	1971-09-30	Hydroxybenzophenone, Verfahren zu deren Herstellung und ihre Verwendung