JPH04252247A - 安定化ポリマー及びその製造方法 - Google Patents

安定化ポリマー及びその製造方法

Info

Publication number: JPH04252247A
Authority: JP; Japan
Prior art keywords: polymer; antioxidant; composition; organotin; oxidatively stabilized
Prior art date: 1990-01-20
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

Application number

JP3019404A

Other languages

English (en)

Japanese (ja)

Inventor

Neil S Davidson

ネイル　シャラー　ディビッドスン

Hilda A Leiper

ヒルダ　アダムズ　リーパー

Murro Colette A A Di

コリット　アスンタ　アーカンジラ　ディ　マロ

Kenneth Wilkinson

ケネス　ウィルキンスン

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.)

BP Chemicals Ltd

Original Assignee

BP Chemicals Ltd

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.)

1990-01-20

Filing date

1991-01-19

Publication date

1992-09-08

1991-01-19 Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd

1992-09-08 Publication of JPH04252247A publication Critical patent/JPH04252247A/ja

Status Pending legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 95
238000004519 manufacturing process Methods 0.000 title claims abstract 3
239000003963 antioxidant agent Substances 0.000 claims abstract description 81
230000003078 antioxidant effect Effects 0.000 claims abstract description 58
229920000098 polyolefin Polymers 0.000 claims abstract description 39
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 35
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims abstract description 28
239000000155 melt Substances 0.000 claims abstract description 25
239000003999 initiator Substances 0.000 claims abstract description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 7
150000003568 thioethers Chemical class 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 49
-1 polyethylene Polymers 0.000 claims description 41
150000002989 phenols Chemical class 0.000 claims description 33
239000004698 Polyethylene Substances 0.000 claims description 24
229920000573 polyethylene Polymers 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 21
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
239000005977 Ethylene Substances 0.000 claims description 10
239000004594 Masterbatch (MB) Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
229920001903 high density polyethylene Polymers 0.000 claims description 5
239000004700 high-density polyethylene Substances 0.000 claims description 5
230000002452 interceptive effect Effects 0.000 claims description 5
150000001336 alkenes Chemical class 0.000 claims description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 claims 2
150000007942 carboxylates Chemical class 0.000 claims 1
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 17
150000002148 esters Chemical class 0.000 abstract description 2
239000000047 product Substances 0.000 description 31
150000003254 radicals Chemical class 0.000 description 21
238000000034 method Methods 0.000 description 18
235000013824 polyphenols Nutrition 0.000 description 15
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 11
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 10
125000004432 carbon atom Chemical group C* 0.000 description 10
238000004132 cross linking Methods 0.000 description 10
238000000605 extraction Methods 0.000 description 9
239000007983 Tris buffer Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
239000002904 solvent Substances 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
230000008018 melting Effects 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
238000010348 incorporation Methods 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000000178 monomer Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
150000002978 peroxides Chemical class 0.000 description 5
230000000087 stabilizing effect Effects 0.000 description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 4
BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001125 extrusion Methods 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
239000000463 material Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229920000231 antioxidant polymer Polymers 0.000 description 3
229920005601 base polymer Polymers 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000006208 butylation Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
230000006698 induction Effects 0.000 description 3
238000000465 moulding Methods 0.000 description 3
150000001451 organic peroxides Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
JOWXNCPELQZFHF-UHFFFAOYSA-N 2-[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoyloxy]ethyl 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoate Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(CC(=O)OCCOC(=O)CC(C)(C=2C=C(C(O)=CC=2)C(C)(C)C)C=2C=C(C(O)=CC=2)C(C)(C)C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 JOWXNCPELQZFHF-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
239000012963 UV stabilizer Substances 0.000 description 2
XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
230000009471 action Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920001038 ethylene copolymer Polymers 0.000 description 2
239000000835 fiber Substances 0.000 description 2
229920000578 graft copolymer Polymers 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229920001684 low density polyethylene Polymers 0.000 description 2
239000004702 low-density polyethylene Substances 0.000 description 2
229940049920 malate Drugs 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000006078 metal deactivator Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
239000002530 phenolic antioxidant Substances 0.000 description 2
239000011990 phillips catalyst Substances 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
230000005855 radiation Effects 0.000 description 2
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229940071127 thioglycolate Drugs 0.000 description 2
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 description 1
GXBCWRMJQPLZDU-UHFFFAOYSA-N 2-methyl-2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)(C)C GXBCWRMJQPLZDU-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
RIVJYLGQARVCBI-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;cumene Chemical compound CC(C)C1=CC=CC=C1.CC(C)(C)OOC(C)(C)C RIVJYLGQARVCBI-UHFFFAOYSA-N 0.000 description 1
HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
VNPRJHMMOKDEDZ-UHFFFAOYSA-L 6-methylheptyl 2-[dibutyl-[2-(6-methylheptoxy)-2-oxoethyl]sulfanylstannyl]sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS[Sn](CCCC)(CCCC)SCC(=O)OCCCCCC(C)C VNPRJHMMOKDEDZ-UHFFFAOYSA-L 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
238000000944 Soxhlet extraction Methods 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
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230000002860 competitive effect Effects 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
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
FFGHLLOLFQHABK-UHFFFAOYSA-L dibutyltin(2+);dodecane-1-thiolate Chemical group CCCCCCCCCCCCS[Sn](CCCC)(CCCC)SCCCCCCCCCCCC FFGHLLOLFQHABK-UHFFFAOYSA-L 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical class C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
ZLQKLRJBHMDQPD-UHFFFAOYSA-L dioctyltin(2+);dodecane-1-thiolate Chemical compound CCCCCCCCCCCCS[Sn](CCCCCCCC)(CCCCCCCC)SCCCCCCCCCCCC ZLQKLRJBHMDQPD-UHFFFAOYSA-L 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
125000003438 dodecyl group Chemical group [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])* 0.000 description 1
238000006446 extruder reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical group CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000011068 loading method Methods 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012803 melt mixture Substances 0.000 description 1
238000010128 melt processing Methods 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical group CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical group C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical class CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000001542 size-exclusion chromatography Methods 0.000 description 1
239000012748 slip agent Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl 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])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
- C08L23/0815—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic 1-olefins containing one carbon-to-carbon double bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond

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)
Processes Of Treating Macromolecular Substances (AREA)

JP3019404A 1990-01-20 1991-01-19 安定化ポリマー及びその製造方法 Pending JPH04252247A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB909001367A GB9001367D0 (en)	1990-01-20	1990-01-20	Oxidatively stable polymers and processes for preparing said polymers
GB9001367		1990-01-20

Publications (1)

Publication Number	Publication Date
JPH04252247A true JPH04252247A (ja)	1992-09-08

Family

ID=10669659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3019404A Pending JPH04252247A (ja)	1990-01-20	1991-01-19	安定化ポリマー及びその製造方法

Country Status (8)

Country	Link
US (1)	US5304589A (2)
EP (1)	EP0442614A3 (2)
JP (1)	JPH04252247A (2)
KR (1)	KR100215536B1 (2)
AU (1)	AU641207B2 (2)
CA (1)	CA2034515A1 (2)
GB (1)	GB9001367D0 (2)
IN (1)	IN180368B (2)

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IT1318478B1 (it)	2000-04-20	2003-08-25	Great Lakes Chemical Europ	Miscele stabilizzanti liquide per polimeri organici.
JP2008507613A (ja) *	2004-07-23	2008-03-13	ポルノクスコーポレーション	抗酸化マクロモノマーおよび抗酸化ポリマー、ならびにその作製方法および使用方法
US20060128930A1 (en) *	2004-12-03	2006-06-15	Ashish Dhawan	Synthesis of sterically hindered phenol based macromolecular antioxidants
WO2006060800A1 (en)	2004-12-03	2006-06-08	Polnox Corporation	Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers
EP1861484A2 (en) *	2005-02-22	2007-12-05	Polnox Corporation	Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
CA2606303A1 (en) *	2005-03-25	2006-10-05	Polnox Corporation	Alkylated and polymeric macromolecular antioxidants and methods of making and using the same
EP1966293A1 (en) *	2005-10-27	2008-09-10	Polnox Corporation	Stabilized polyolefin compositions
WO2007050985A2 (en) *	2005-10-27	2007-05-03	Polnox Corporation	Macromolecular antioxidants based on stξrically hindered phenolic phosphites
US20070106059A1 (en) *	2005-10-27	2007-05-10	Cholli Ashok L	Macromolecular antioxidants and polymeric macromolecular antioxidants
US20070161522A1 (en)	2005-12-02	2007-07-12	Cholli Ashok L	Lubricant oil compositions
WO2008005358A2 (en) *	2006-07-06	2008-01-10	Polnox Corporation	Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same
US7767853B2 (en)	2006-10-20	2010-08-03	Polnox Corporation	Antioxidants and methods of making and using the same
KR20080101791A (ko) *	2007-05-16	2008-11-21	주식회사 엘지화학	장쇄분지를 포함하는 에틸렌-알파올레핀 공중합체
US8110532B2 (en)	2008-11-24	2012-02-07	Chemtura Corporation	Antioxidant compositions
CN103975011A (zh) *	2011-10-14	2014-08-06	嘉拉塔化工有限责任公司	源自可再生原料的增塑剂
WO2015077635A2 (en)	2013-11-22	2015-05-28	Polnox Corporation	Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same
JP6336622B2 (ja) *	2014-02-03	2018-06-06	アランセオ・ドイチュランド・ゲーエムベーハー	安定化ゴム
US20180251695A1 (en)	2017-03-01	2018-09-06	Polnox Corporation	Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same
CN111454403A (zh) *	2020-04-17	2020-07-28	安徽世倾环保科技有限公司	耐腐蚀氧化滤袋的滤料制备方法
FR3113664B1 (fr)	2020-08-27	2022-08-05	Asidium	Dispositif de machine industrielle de pelliculage à plat selon un principe de multiplication de modules de pelliculage

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GB1055299A (en) *	1963-06-07	1967-01-18	Toyo Rayon Co Ltd	Heat-stabilized dyeable polyolefin compositions
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1990
- 1990-01-20 GB GB909001367A patent/GB9001367D0/en active Pending
1991
- 1991-01-18 CA CA002034515A patent/CA2034515A1/en not_active Abandoned
- 1991-01-18 US US07/643,723 patent/US5304589A/en not_active Expired - Fee Related
- 1991-01-18 AU AU69819/91A patent/AU641207B2/en not_active Ceased
- 1991-01-18 IN IN43DE1991 patent/IN180368B/en unknown
- 1991-01-18 EP EP19910300407 patent/EP0442614A3/en not_active Withdrawn
- 1991-01-19 KR KR1019910000920A patent/KR100215536B1/ko not_active Expired - Fee Related
- 1991-01-19 JP JP3019404A patent/JPH04252247A/ja active Pending

Also Published As

Publication number	Publication date
GB9001367D0 (en)	1990-03-21
KR100215536B1 (ko)	1999-08-16
KR910014444A (ko)	1991-08-31
CA2034515A1 (en)	1991-07-21
EP0442614A2 (en)	1991-08-21
US5304589A (en)	1994-04-19
AU6981991A (en)	1991-07-25
EP0442614A3 (en)	1992-07-01
IN180368B (2)	1998-01-24
AU641207B2 (en)	1993-09-16

Publication	Publication Date	Title
JPH04252247A (ja)	1992-09-08	安定化ポリマー及びその製造方法
US6525158B1 (en)	2003-02-25	Process for the stabilization of a stabilizer mixtures for recycled plastic mixtures
CA1190692A (en)	1985-07-16	Polyethylene compositions for rotational moulding processes
BRPI0900686A2 (pt)	2010-05-04	composições reticuláveis, processo para a produção de composições e de elastÈmeros termoplásticos, elastÈmeros termoplásticos, uso de composições e de elastÈmeros termoplásticos, moldes, revestimentos de cabo, adesivos a quente ou pelìculas
US4835194A (en)	1989-05-30	Film-forming compositions and fog resistant film produced therefrom
CA2574515A1 (en)	2006-02-16	Moisture-curable, silane crosslinkable composition
US5401787A (en)	1995-03-28	Flame retardant insulation compositions
US5238978A (en)	1993-08-24	Peroxide masterbatches using polycaprolactone as the carrier
EP0194382B1 (en)	1989-02-15	Pigmented thermoplastic polymer master batch composition
JP2830358B2 (ja)	1998-12-02	高酸化防止性樹脂組成物
CA2022349C (en)	2001-07-17	Peroxide masterbatches using polycaprolactone as the carrier
AU654361B2 (en)	1994-11-03	Cross linkable polymeric composition
US3060149A (en)	1962-10-23	Stabilized polymer compositions
EP0501671A2 (en)	1992-09-02	Crosslinkable polymeric composition
CN1258692A (zh)	2000-07-05	交联低烟无卤阻燃聚烯烃复合材料及其制备方法
US3708457A (en)	1973-01-02	Pigmented polyolefin compositions containing phthalocyanine compounds
CA2100457A1 (en)	1992-07-15	Stabilized polyethylene resins and method of stabilization
US3542725A (en)	1970-11-24	Plastic compositions containing sulfite and thiol stabilizers
AU625411B2 (en)	1992-07-09	Process for stabilizing mixtures based on halogenated polymers
AU671809B2 (en)	1996-09-12	Crosslinkable polymeric composition
JPH03273061A (ja)	1991-12-04	安定化樹脂組成物
JPS6042441A (ja)	1985-03-06	ポリエチレン組成物
CA1068040A (en)	1979-12-11	Low pressure ethylene polymer based compositions
CN111410832B (zh)	2022-10-28	一种抗老化油漆附着性能高的组合物及其制备方法
JPS6067549A (ja)	1985-04-17	有機アンチモン化合物およびオルトメルカプトフエノ−ル化合物によって安定化されたハロゲン含有ポリマ−