CA2087227A1 - Stabilisants oxamidiques - Google Patents

Stabilisants oxamidiques

Info

Publication number: CA2087227A1
Authority: CA; Canada
Prior art keywords: compounds; formula; silicon; organic polymer; organofunctional
Prior art date: 1992-01-14
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.): Abandoned

Application number

CA 2087227

Other languages

English (en)

Inventor

Carlo Neri

Luciano Pallini

Daniele Fabbri

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Enichem Sintesi SpA

Original Assignee

Individual

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.)

1992-01-14

Filing date

1993-01-13

Publication date

1993-07-15

1993-01-13 Application filed by Individual filed Critical Individual

1993-07-15 Publication of CA2087227A1 publication Critical patent/CA2087227A1/fr

Status Abandoned legal-status Critical Current

Links

239000003381 stabilizer Substances 0.000 title abstract description 10
229910052710 silicon Inorganic materials 0.000 claims abstract description 7
239000010703 silicon Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 40
230000000087 stabilizing effect Effects 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
-1 Polysiloxanes Polymers 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
229920000620 organic polymer Polymers 0.000 claims description 8
229920000642 polymer Polymers 0.000 claims description 8
238000006116 polymerization reaction Methods 0.000 claims description 6
229920001577 copolymer Polymers 0.000 claims description 4
229920000098 polyolefin Polymers 0.000 claims description 4
229920001296 polysiloxane Polymers 0.000 claims description 4
229920002943 EPDM rubber Polymers 0.000 claims description 3
229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
230000006641 stabilisation Effects 0.000 claims description 3
238000011105 stabilization Methods 0.000 claims description 3
229920003051 synthetic elastomer Polymers 0.000 claims description 3
239000005061 synthetic rubber Substances 0.000 claims description 3
229920001897 terpolymer Polymers 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000007787 solid Substances 0.000 abstract description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000654 additive Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 8
230000000996 additive effect Effects 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
238000012512 characterization method Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
239000000243 solution Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
229920001903 high density polyethylene Polymers 0.000 description 3
239000004700 high-density polyethylene Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000005012 migration Effects 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
OZXSNNLNKWAGLD-UHFFFAOYSA-N Cl.CCCCCCC=C Chemical compound Cl.CCCCCCC=C OZXSNNLNKWAGLD-UHFFFAOYSA-N 0.000 description 1
GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
239000002656 Distearyl thiodipropionate Substances 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000004703 cross-linked polyethylene Substances 0.000 description 1
229920003020 cross-linked polyethylene Polymers 0.000 description 1
230000003413 degradative effect Effects 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011810 insulating material Substances 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
229920000092 linear low density polyethylene Polymers 0.000 description 1
239000004707 linear low-density polyethylene Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229920001684 low density polyethylene Polymers 0.000 description 1
239000004702 low-density polyethylene Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
FFYAVOJIYAAUNX-UHFFFAOYSA-N n,n'-diethyloxamide Chemical compound CCNC(=O)C(=O)NCC FFYAVOJIYAAUNX-UHFFFAOYSA-N 0.000 description 1
239000002667 nucleating agent Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

CA 2087227 1992-01-14 1993-01-13 Stabilisants oxamidiques Abandoned CA2087227A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITPA920055		1992-01-14
ITMI92A000055		1992-01-14

Publications (1)

Publication Number	Publication Date
CA2087227A1 true CA2087227A1 (fr)	1993-07-15

Family

ID=11388669

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2087227 Abandoned CA2087227A1 (fr)	1992-01-14	1993-01-13	Stabilisants oxamidiques

Country Status (1)

Country	Link
CA (1)	CA2087227A1 (fr)

1993
- 1993-01-13 CA CA 2087227 patent/CA2087227A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1999-10-26	EEER	Examination request
2001-01-15	FZDE	Dead

Publication	Publication Date	Title
US4946880A (en)	1990-08-07	Silylated U.V. stabilizers containing hindered tertiary amines
CA1168852A (fr)	1984-06-12	Stabilisateur pour substance polymerique; composition a base de cette substance renfermant le stabilisateur
US5945555A (en)	1999-08-31	Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone composition
DE19603241C1 (de)	1997-07-10	Multifunktionelle, cyclische Organosiloxane, Verfahren zu deren Herstellung und deren Verwendung
US5302735A (en)	1994-04-12	Polysiloxanic stabilizers containing sterically hindered phenol groups and oxamidic groups
US3243429A (en)	1966-03-29	Aziridinyl siloxanes
US5264604A (en)	1993-11-23	Oxamidic stabilizers
US5216103A (en)	1993-06-01	Siliconic u.v. stabilizers containing reactive groups
CN109971034B (zh)	2022-03-08	硅烷混合物和其制备方法
CA2164278A1 (fr)	1996-06-06	Derives d'ester de bisphenol
US3778430A (en)	1973-12-11	Silicon substituted azonitriles
CA2013407A1 (fr)	1990-09-30	Compositions de polymeres stabilisees par des polydialkylsiloxanes renfermant des unites siloxy associees a certains groupes phenol definis encombres steriquement
GB2075533A (en)	1981-11-18	Process for producing alkoxylated silanes
EP0532121A1 (fr)	1993-03-17	Stabilisants polysiloxaniques comportant des groupes phénols à empêchement stériques et des groupes réactifs
US6153781A (en)	2000-11-28	Silacyclobutene compounds, methods of preparing same, and polymers formed therefrom
DE69423954T2 (de)	2000-10-05	Hartbäres Silizium-enthaltendes Polymer und härtbare Zusammensetzung auf Basis dieses Polymeres
US4788311A (en)	1988-11-29	Novel organosilicon compounds useful as a stabilizer for organopolysiloxane compositions
US4417071A (en)	1983-11-22	Phenols useful as stabilizers
CN110003525B (zh)	2022-03-08	硅烷混合物和其制备方法
US6136940A (en)	2000-10-24	Silacyclobutane compounds, methods of preparing same, and polymers formed therefrom
CA2058762C (fr)	2001-05-08	Esters aryliques d'acide phosphonique; methode de preparation et utilisation pour stabiliser des matieres plastiques, notamment des polyolefines de moulage
US5914419A (en)	1999-06-22	Organosilicon compound
CN121175320A (zh)	2025-12-19	具有用甲硅烷基保护的羧基的有机氧基硅烷化合物及其制造方法
SU256769A1 (ru)		Способ получения оловоорганических ацетиленовых соединений
US2863893A (en)	1958-12-09	Arsonosiloxanes and their preparation