CA1244597A - Amines polymeres comportant un empechement sterique - Google Patents

Amines polymeres comportant un empechement sterique

Info

Publication number: CA1244597A
Authority: CA; Canada
Prior art keywords: olefin polymer; tetramethylpiperidine; residue; weight; mixture
Prior art date: 1985-05-23
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

Application number

CA000482119A

Other languages

English (en)

Inventor

Anthony B. Clayton

William R. Diveley

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.)

FIBERVISIONS LP

Hercules LLC

Original Assignee

Hercules LLC

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.)

1985-05-23

Filing date

1985-05-23

Publication date

1988-11-08

1985-05-23 Application filed by Hercules LLC filed Critical Hercules LLC

1985-05-23 Priority to CA000482119A priority Critical patent/CA1244597A/fr

1988-11-08 Application granted granted Critical

1988-11-08 Publication of CA1244597A publication Critical patent/CA1244597A/fr

Status Expired legal-status Critical Current

Links

150000001412 amines Chemical class 0.000 title abstract description 17
229920000098 polyolefin Polymers 0.000 claims abstract description 43
YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims abstract description 15
-1 polypropylene residue Polymers 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 14
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 13
239000004743 Polypropylene Substances 0.000 claims description 12
229920000642 polymer Polymers 0.000 claims description 12
229920001155 polypropylene Polymers 0.000 claims description 11
239000004711 α-olefin Substances 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 4
229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
GOJOVSYIGHASEI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)NC(C)(C)C1 GOJOVSYIGHASEI-UHFFFAOYSA-N 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 21
239000004611 light stabiliser Substances 0.000 abstract description 11
239000000463 material Substances 0.000 abstract description 9
150000001336 alkenes Chemical class 0.000 abstract description 2
229940044600 maleic anhydride Drugs 0.000 description 18
150000001875 compounds Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 9
229920001577 copolymer Polymers 0.000 description 8
150000003254 radicals Chemical group 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000008096 xylene Substances 0.000 description 7
150000003949 imides Chemical class 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
229920005629 polypropylene homopolymer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
238000000034 method Methods 0.000 description 2
238000000465 moulding Methods 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
239000000843 powder Substances 0.000 description 2
229940095050 propylene Drugs 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010015946 Eye irritation Diseases 0.000 description 1
229940123457 Free radical scavenger Drugs 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
229920003300 Plexar® Polymers 0.000 description 1
208000037062 Polyps Diseases 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
239000000428 dust Substances 0.000 description 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 description 1
229920001038 ethylene copolymer Polymers 0.000 description 1
231100000013 eye irritation Toxicity 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
239000004700 high-density polyethylene Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
229920001684 low density polyethylene Polymers 0.000 description 1
239000004702 low-density polyethylene Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000013014 purified material Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 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 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004753 textile Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000482119A 1985-05-23 1985-05-23 Amines polymeres comportant un empechement sterique Expired CA1244597A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000482119A CA1244597A (fr)	1985-05-23	1985-05-23	Amines polymeres comportant un empechement sterique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000482119A CA1244597A (fr)	1985-05-23	1985-05-23	Amines polymeres comportant un empechement sterique

Publications (1)

Publication Number	Publication Date
CA1244597A true CA1244597A (fr)	1988-11-08

Family

ID=4130531

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000482119A Expired CA1244597A (fr)	1985-05-23	1985-05-23	Amines polymeres comportant un empechement sterique

Country Status (1)

Country	Link
CA (1)	CA1244597A (fr)

1985
- 1985-05-23 CA CA000482119A patent/CA1244597A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-11-08	MKEX	Expiry

Publication	Publication Date	Title
US4520171A (en)	1985-05-28	Polymeric hindered amines
EP0070358B1 (fr)	1987-01-21	Nouveaux stabilisateurs à la lumière pour des polymères
US3542729A (en)	1970-11-24	Stabilization of synthetic polymers
JPS6341394B2 (fr)	1988-08-17
EP0293253B1 (fr)	1993-05-12	Photostabilisants à base d'amines polymères à empêchement stérique
EP0022080A1 (fr)	1981-01-07	Compositions de polymères synthétiques contenant des dérivés de la triazine comme stabilisants contre les dégradations sous l'action de la lumière et certains dérivés de la triazine
CA1169061A (fr)	1984-06-12	COPOLYMERES D'.alpha.-OLEFINES CONTENANT DES GROUPEMENTS AMINES SUSPENDUS EMPECHES
JP2594612B2 (ja)	1997-03-26	安定化コポリマー組成物
US4395508A (en)	1983-07-26	Polycondensates of substituted piperidines and use thereof as stabilizers for polymers
GB2202226A (en)	1988-09-21	Bound antioxidant masterbatches
EP0373778B1 (fr)	1995-01-25	Composés à base de triazine comme stabilisateurs à la lumière pour matières plastiques
CA1244597A (fr)	1988-11-08	Amines polymeres comportant un empechement sterique
US5658973A (en)	1997-08-19	Compositions for the stabilization of synthetic polymers
KR0163474B1 (ko)	1999-01-15	합성 중합체 안정화용 조성물
CA1169067A (fr)	1984-06-12	Polymeres a base de piperidine et emploi comme agents stabilisateurs
EP0373779B1 (fr)	1995-01-25	Composés à base de mélamine comme stabilisateurs à la lumière pour matières plastiques
US4373042A (en)	1983-02-08	N,N-Di-(hydroxy-phenyl) derivatives of piperazine and use thereof as stabilizers for polymers
US4240954A (en)	1980-12-23	Polymers stabilized against degradation by ultraviolet radiation
US4386177A (en)	1983-05-31	Light stabilizers for polymers containing hindered piperidinyl-substituted 1,3,5 triazine groups
US4370430A (en)	1983-01-25	Hindered amine light stabilizers for polymers
AU701371B2 (en)	1999-01-28	Polyketone polymer composition
CA1287057C (fr)	1991-07-30	Photosbilisants de type spiroacetals de type polyalkylpiperidin-4-one a base de malonate
JPS62143907A (ja)	1987-06-27	トリアジン系光安定剤化合物の製造方法
JPH07179685A (ja)	1995-07-18	ピペリジニルホスフィット組成物及びそれらを含むポリオレフィン組成物
EP0031424A1 (fr)	1981-07-08	Polyesters de N,N-di-alcanol-amines et de bis-(hydroxy-alkyl-benzyl)-acides maloniques et compositions les contenant comme stabilisants