CN1036275C - 3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,0-,二磷杂螺环(5,5)十一烷在聚烯烃中作为稳定剂 - Google Patents
3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,0-,二磷杂螺环(5,5)十一烷在聚烯烃中作为稳定剂 Download PDFInfo
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- CN1036275C CN1036275C CN92109331A CN92109331A CN1036275C CN 1036275 C CN1036275 C CN 1036275C CN 92109331 A CN92109331 A CN 92109331A CN 92109331 A CN92109331 A CN 92109331A CN 1036275 C CN1036275 C CN 1036275C
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- Prior art keywords
- tertiary butyl
- ester
- acid
- butyl
- phenyl
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- NNRXZKGFFVLIQF-UHFFFAOYSA-N dipiperidin-4-yl hydrogen phosphite Chemical compound C1CNCCC1OP(O)OC1CCNCC1 NNRXZKGFFVLIQF-UHFFFAOYSA-N 0.000 title 1
- -1 polyethylene Polymers 0.000 claims abstract description 108
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- 239000000203 mixture Substances 0.000 claims description 45
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 9
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- 230000015556 catabolic process Effects 0.000 claims description 7
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- 238000007254 oxidation reaction Methods 0.000 claims description 4
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- 239000002530 phenolic antioxidant Substances 0.000 claims description 2
- 239000011368 organic material Substances 0.000 abstract description 17
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- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
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- 239000002253 acid Substances 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 13
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- 150000002431 hydrogen Chemical class 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- 239000000654 additive Substances 0.000 description 8
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- 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 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
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- 150000001993 dienes Chemical class 0.000 description 6
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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- 239000000460 chlorine Substances 0.000 description 5
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- 229940059574 pentaerithrityl Drugs 0.000 description 5
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- PMNGNPRHPYYVNM-UHFFFAOYSA-N 1-hydroxyundecane-3-sulfonic acid Chemical compound CCCCCCCCC(CCO)S(O)(=O)=O PMNGNPRHPYYVNM-UHFFFAOYSA-N 0.000 description 4
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- VEZIKIAGFYZTCI-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(OC)C=C1 VEZIKIAGFYZTCI-UHFFFAOYSA-N 0.000 description 1
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- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 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
- YVYHWOZEQUFKOB-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(N)=O YVYHWOZEQUFKOB-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- CSWFWSPPZMEYAY-UHFFFAOYSA-N octadecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)O CSWFWSPPZMEYAY-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
- 125000005447 octyloxy 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])O* 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 229920009441 perflouroethylene propylene Polymers 0.000 description 1
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- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- ZDNRHFGRVXPQAI-UHFFFAOYSA-N piperidin-1-yl dihydrogen phosphite Chemical compound OP(O)ON1CCCCC1 ZDNRHFGRVXPQAI-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 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 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/529—Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
本发明涉及式I的新化合物3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺(5,5)十一烷:
该化合物可用作有机材料的稳定剂,特别是用作聚乙烯和聚丙烯的加工稳定剂。
Description
本发明涉及新化合物3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺环〔5,5〕十一烷,含有所说化合物的组合物,以及它们作为有机材料稳定剂的应用。
有机亚磷酸酯和膦酸酯已知可用作共稳定剂继发抗氧化剂及加工稳定剂,特别是用于聚烯烃。这类已知亚磷酸酯稳定剂的例子包括R.G_chter/H.M_ller(Ed.),PlasticsAdditives Handbook,3rd Ed.,P47,Hanser,Hunich.1990中所用的连接螺环的双亚磷酸酯。
位阻胺,特别含有2,2.6,6-四甲基-哌啶基的位阻胺已优选用作位阻胺光稳定剂(HALS)。
GB-A-1513629中公开了许多
类型的基本不对称的哌啶基亚磷酸酯,以及双亚磷酸酯,其中包括3,9-双(2,2,6,6-四甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷(第7页第45-50行的实施例8;命名已根据IUPAC的规定作了修改)。
GB-A-2014586中还指出了3,9-双(2,2,6,6-四甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷作为稳定烯烃聚合物的应用。
US-A-5021481中公开了相应的N-烷氧基取代的双-4-哌啶亚磷酸酯。
仍然有必要为那些对氧化、热和/或光诱导之降解作用敏感的有机材料提供有效的稳定剂。
现已令人惊奇地发现,如下列式I所示的特定双-4-哌啶亚磷酸酯化合物,是有机材料的很适用的稳定剂。有必要对该化合物作为合成聚合物之加工聚稳定剂的适用性作特殊说明。
一个方面,本发明涉及式I的化合物3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷
可从已知的并已描述过的3,9-二氯-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷(特别参见Houben-Wey1,2nd Edition,Vol.XII/2,pp.48,Thieme-Verlag,Stuttgart 1964)开始制备式I的化合物。在该反应中,起始化合物在适当的有机极性或非极性非质子传递溶剂存在下与约2当量1,2,2,6,6-五甲基哌啶-4-醇反应。该反应最好在碱存在下,在0℃至溶剂沸点的温度范围内进行。
另外,也可以使用由1,2,2,6,6-五甲基哌啶-4-醇衍生的醇化物代替碱。
可以使用从催化量到化学计算量以至超过哌啶衍生物多摩尔过量的不同量的碱。可使用碱使反应中生成的氯化氢转化成氯化物,后者则可经过滤和/或用适当的含水或固相洗涤而除去。该方法中也可以使用第二种可与水混溶的溶剂。可通过重结晶有机相的残留物来纯化产物,然后浓缩或蒸发至干。用于重结晶的溶剂一般是乙腈或己烷。
适于进行缩合反应的溶剂包括烃(如甲苯、二甲苯、己烷、戊烷或其它石油醚馏份)、卤代烃(如二或三氯甲烷、1,2-二氯乙烷、1,1,1-三氯乙烷)、醚(如二***、二丁醚或四氢呋喃),以及乙腈、二甲基甲酰胺、二甲基亚砜、N-甲基吡咯烷酮。
适用的碱包括叔胺(如三甲胺、三乙胺、三丁胺、N,N-二甲苯胺、N,N-二乙苯胺或吡啶)、氢化物(如氢化锂、钠、钾)或醇化物(典型的是甲醇钠)。
也可使用氢化物、碱金属、碱金属氢氧化物或甲醇钠形成1,2,2,6,6-五甲基哌啶-4-醇的醇化物。在与氯代亚磷酸酯反应之前经蒸馏(如用甲苯作共沸物)除去所生成的反应产物(如水、甲醇)。
进一步的制备方法可从低沸点醇或酚的适当酯或适当酰胺开始,以代替从3,9-二氯-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷开始。因此可按照上述的一般性方法,使用3,9-二乙氧基-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷或3,9-双(二甲氨基)-2,4,8,10-四氧杂-3,9-二磷杂螺环〔5,5〕十一烷作为起始化合物。在此情况下,须选用适当反应条件以使反应期间生成的低沸点醇或酚或酰胺能够通过蒸馏被定量地除去(参见GB-A-1513629中所述的相似反应)。
式I的化合物特别适用于稳定有机材料,对抗光诱导的热和/或氧化降解作用。因此,本发明还涉及包含(a)一种对氧化、热和/或光诱导的降解作用敏感的有机材料,以及(b)式I化合物的组合物。
这类有机材料的有代表性例子是:
1.单烯烃和二烯属烃的聚合物,如聚丙烯、聚异丁烯、聚丁-1-烯、聚甲基戊-1-烯、聚异丙烯或聚丁二烯,以及环烯烃的聚合物,如环戊烯或降冰片烯、聚乙烯(其可以是未交联的或交联的),如高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、分支低密度聚乙烯(BLDPE)的聚合物。
2.上面1)中提到的聚合物的混合物,如聚丙烯与聚异丁烯,聚丙烯与聚乙烯(如PP/HDPE,PP/LDPE)的混合物和不同类型聚乙烯(如LDPE/HDPE)的混合物。
3.单烯烃和二烯烃彼此间的共聚物,或它们与其它乙烯单体的共聚物,典型的有乙烯/丙烯、线性低密度聚乙烯(LLDPE)及其与低密度聚乙烯(LDPE)的混合物、丙烯/丁-1-烯、乙烯/己烯、乙烯/乙基戊烯、乙烯/庚烯、乙烯/辛烯、丙烯/异丁烯、乙烯/丁-1-烯、丙烯/丁二烯、异丁烯/异戊二烯、乙烯/丙烯酸烷基酯、乙烯/异丁烯酸烷基酯、乙烯/乙酸乙烯酯共聚物或乙烯/丙烯酸共聚物以及它们的盐(离聚物)和乙烯与丙烯和二烯如己二烯、二环戊二烯或亚乙基-降冰片烯的三元聚合物;以及它们之间和与上文1)中所述聚合物的混合物,如聚丙烯/乙烯-丙烯共聚物,LDPE/乙烯-乙酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA和随机或交替的聚烷烯/一氧化碳共聚物以及它们与其它聚合物如聚酰胺的混合物。
3a.烃类树脂(如C5-C9)和其氢化的修饰产物(如增稠剂),以及聚链烷烯与淀粉的混合物。
4.聚苯乙烯、聚(对位甲基苯乙烯)、聚(α-甲基苯乙烯)。
5.苯乙烯或α-甲基苯乙烯与二烯或丙烯酸衍生物的共聚物,典型的有苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/异丁烯酸烷基酯、苯乙烯/马来酐、苯乙烯/丁二烯/丙烯酸烷基酯、苯乙烯/丁二烯/异丁烯酸烷基酯、苯乙烯/丙烯腈/丙烯酸甲酯;高冲击强度苯乙烯共聚物与另一种聚合物,如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元聚合物的混合物;以及苯乙烯的嵌段共聚物,如苯乙烯/丁二烯/苯乙烯、苯乙烯/异戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6.苯乙烯或α-甲基苯乙烯的接枝共聚物,典型的有在聚丁二烯上接苯乙烯,在苯丁二烯-苯乙烯或聚丁二烯-丙烯腈上接苯乙烯,在聚丁二烯上接苯乙烯和丙烯腈(或异丁烯腈)、在聚丁二烯上接苯乙烯和马来酐或马来酰胺、在聚丁二烯上接苯乙烯,丙烯腈和马来酐或马来酰胺、在聚丁二烯上接苯乙烯、丙烯腈和异丁烯酸甲酯,在聚丁二烯上接苯乙烯和丙烯酸烷基酯或异丁烯酸烷基酯、在乙烯/丙烯/二烯三元聚合物上接苯乙烯和丙烯腈、在聚丙烯酸或聚异丁烯酸酯上接苯乙烯和丙烯腈、在丙烯酸酯/丁二烯共聚物上接苯乙烯和丙烯腈、以及它们与5)中所列共聚物的混合物,如称为ABS、MBS、ASA或AES聚合物的共聚物混合物。
7.含卤素聚合物,典型的有聚氯丁二烯、氯化橡胶、氯化或氯硫化聚乙烯、乙烯和氯化乙烯的共聚物、表氯醇均聚和共聚物,卤化乙烯化合物的聚合物,如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏氟乙烯、以及其共聚物,如氯乙烯/偏二氯乙烯、氯乙烯/乙酸乙烯酯或偏二氯乙烯/乙酸乙烯酯共聚物。
8.衍生于α,β-不饱和酸和其衍生物的聚合物,如聚丙烯酸酯和聚异丁烯酸酯、用丙烯酸丁酯冲击修饰的聚异丁烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
9.上文8)中所述单体彼此间或与其它不饱和单体的共聚物,如丙烯腈/丁二烯、丙烯腈/丙烯酸烷基酯、丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/卤乙烯共聚物或丙烯腈/异丁烯酸烷基酯/丁二烯三元聚合物。
10.衍生于不饱和醇和胺,或其酰基衍生物或其缩醛的聚合物,典型的有聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙基酯或聚烯丙基蜜胺;以及它们与上文1)中提到的烯烃的共聚物。
11.环酯的均聚物和共聚物,典型的有聚二醇、聚环氧乙烷、聚环氧丙烷或它们与缩水甘油醚的共聚物。
12.聚缩醛,如聚甲醛和那些含有环氧乙烷作为共聚用单体的聚甲醛;用热望聚氨基甲酸乙酯、丙烯酸酯或MBS修饰的聚缩醛。
13.聚苯氧和聚苯硫,以及聚苯氧与聚苯乙烯或聚酰胺的混合物。
14.一方面由聚醚、聚酯或带羟基末端的聚丁二烯,且另一方面由脂族或芳族聚异氰酸酯及其前体衍生的聚氨酯。
15.由二胺和二羧酸和/或由氨基羧酸或相应内酰胺衍生的聚酰胺和共聚酰胺,如通过缩合间二甲苯、二胺和己二酸所得到的聚酰胺4、聚酰胺6、聚酰胺6/6、6/10、6/9、6/12、4/6、12/12、聚酰胺11、聚酰胺12、芳族聚酰胺;由六亚甲基二胺和间苯二酸和/或对苯二酸,且可加入高弹体作为修饰剂而制备的聚酰胺,如聚(2,4,4-三甲基亚己基)对苯二酰胺或聚-间-亚苯基间苯二酰胺;另外还有上述聚酰胺与聚烯烃、链烯烃共聚物、离聚物或化学结合或接枝的高弹体生成的共聚物,或者与聚醚,如与聚乙二醇、聚丙二醇或聚亚丁二醇形成的共聚物;用EPDM或ABS修饰的聚酰胺或共聚酰胺;在加工期间缩合的聚酰胺(RIM聚酰胺***)。
16.聚脲:聚酰亚胺、聚酰胺-酰亚胺和聚苯并咪唑。
17.由二羧酸和二醇和/或由羟基羧酸或相应的内酯衍生的聚酯,如聚对苯二甲酸乙酯、聚对苯二甲酸丁酯、聚对苯二甲酸1,4二羟甲基环己酯、聚〔2,2-(4-羟苯基)丙烷〕对苯二甲酸酯以及由带羟基末端的聚醚衍生的聚羟基苯甲酸酯以及嵌段-共聚多醚-酯。
18.聚碳酸酯和聚酯碳酸酯。
19.聚砜、聚砜醚和聚酮醚。
20.一方面衍生于醛,另一方面衍生于酚、脲和蜜胺的交联聚合物,如苯酚/甲醛树脂、脲/甲醛树脂和蜜胺/甲醛树脂。
21.干燥和未干燥醇酸树脂。
22.由饱和和不饱和的二羧酸与多元醇和乙烯系化合物(作为交联剂)衍生的不饱和的聚酯,以及其卤化的低可燃性修饰产物。
23.由取代的丙烯酸酯如环氧丙烯酸酯、聚氨酯丙烯酸酯或聚酯丙烯酸酯衍生的可交联的丙烯酸树脂。
24.与蜜胺树脂尿素树脂、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂或丙烯酸树脂。
25.由聚环氧化物特别是双缩水甘油醚或由脂环族环氧化物衍生的交联环氧树脂。
26.天然聚合物,如纤维素、橡胶、明胶及其化学修饰的同源衍生物,如乙酸纤维素、丙酸纤维素和丁酸纤维素,或纤维素醚,特别是甲基纤维素、松香及其衍生物。
27.上述聚合物的混合物,特别是PP/EPDM、聚酰胺EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑的PUR、PC/热塑的PUR、POM/丙烯酸酯、POM/MBS、PPE/HIPS、PPE/PA6.6及共聚物、PA/HDPE、PA/PP、PA/PPE。
28.作为这些化合物之纯单体化合物或混合物的天然存在或合成的有机材料,如包括矿物油、动物和植物脂肪、油和蜡,或基于合成酯的油脂肪和蜡(如邻苯二甲酸酯、己二酸酯、磷酸酯或苯三酸酯),合成酯与矿物油以可用作纺织组合物的 任何重量比例混合的混合物以及这些材料的含水乳剂。
29.天然或合成橡胶的含水乳剂,如羧化苯乙烯/丁二烯共聚物的天然乳胶或胶乳。
本发明进一步涉及包括成分(a),即天然、半合成或合成聚合物的组合物,所说的聚合物对氧化、热和/或光诱导的降解作用敏感,特别是热塑的聚合物,较好是聚烯烃,更好是聚乙烯或聚丙烯。
本发明还涉及式I的化合物在稳定有机材料对抗氧化,热和/或光化降解中的应用,特别是在热塑聚合物中作为加工稳定剂(热稳定剂)的应用。
被保护的有机材料较好是天然、半合成的,或更好是合成的有机材料。特别优选的有机材料是热塑的聚合物,较好是PVC或聚烯烃,更好是聚乙烯和聚丙烯(PP)。
本发明的组合物所含式I化合物的量常规为重量的0.01-10%,典型为0.05-5%,较好是0.05-3%,更好是0.05-1%。该重量百分比是基于所说化合物的总量。计算是基于没有式1化合物之有机材料的总重量。
可通过混合或加入的方法将式I的化合物掺入有机材料中,然后再按本领域常用方法进一步加入适当添加剂。如果有机材料是聚合物,特别是合成聚合物,可在加工成型物体前或期间掺入,或者将已溶解或分散的化合物加入聚合物中,然后蒸发或不蒸发掉溶剂。在使用高弹体的情况下,这些材料亦可作胶乳得以稳定。将式I化合物混入聚合物中的其它方法包括在聚合相应单体之前、期间或之后,或者在交联之前加入所说的化合物。也可以胶囊包裹的形式(如在蜡、油或聚合物中)加入式I的化合物。如果在聚合前或期间加入式I的化合物,它也可以用作聚合物链长度的调节剂(链终止剂)。
也可以以含有该化合物之母炼胶的形式将式I的化合物加入被稳定的聚合物中,其一般浓度为2.5-25%(重量)。
可按下述技术掺入式I的化合物:
——作为乳剂或分散剂(如加入胶乳或乳剂聚合物中);
——作为同时混合其它成分或聚合物混合物的干混合物;
——直接加到加工装置(如挤压机、密封式混合机等)内;
——作为溶液或熔化物。
本发明的聚合物组合物可以以不同形式使用,并可加工成不同产品,包括薄板,丝、条带,模制件、压型件或作为涂料和清漆的粘合剂、胶粘剂或油灰。
如前所述,被保护的有机材料较好是天然、半合成或更好为合成的聚合物。其特别适用于保护热塑树脂,更好是适用于聚烯烃。在此,须特别提到式I化合物作为加工稳定剂(热稳定剂)的极好作用。为此目的,可在加工聚合物之前或期间常规加入式I的化合物。但也可以稳定其它聚合物(如高弹体)或润滑剂及水力流体以对抗降解,如光诱导的和/或热氧化降解作用。高弹体的例子可在上面列出的可能的有机材料中找到。
适当的润滑剂和水力流体可基于矿物油或合成油或其混合物。润滑剂是本领域技术人员已知的,并已在现有技术文献中作了描述,如参见Dieter Klamann,″Schmierstoffe und verwandle Produkte″(Lubricants and Related Products),Verlag Chemie,Weinheim,1982,in Schewe-Kobek,″Das Schmiermittel-Taschenbuch″(The Lubricant Handbook),D r.Alfred H_thig-Verlag,Heidelberg,1974)and in″Ulimanns Enzyklop_die dertechnisehen Chemie″,(Encyclopedia of Industrial Chemistry),Vol.13,pages 85-94(Verlag Chemie,Weinheim,1977).
本发明进一步包括保护有机材料对抗氧化、热和/或光化降解的方法,该方法包括向所说的材料中掺入或加入式I的化合物,作为其稳定剂。
除含有该新化合物外,本发明的组合物当具体含有有机、更好是合成聚合物的组合物时,还可含有其它常规添加剂。
其它添加剂的例子是:
1.抗氧化剂
1.1烷基化的一元酚,如2,6-二-叔丁基-4-甲基酚、2-叔丁基-4,6-二甲基酚、2,6-二叔丁基-4-乙基酚、2,6-二-叔丁基-4-正丁基酚、2,6-二-叔丁基-4-异丁基酚、2,6-二环戊基-4-甲基酚、2-(2-甲基环己基)-4,6-二甲基酚、2,6-二-十八基-4-甲基酚、2,4,6-三环己基酚、2,6-二-叔丁基-4-甲氧基甲基酚、2,6-二壬基-4-甲基酚、2,4-二甲基-6-(1′-甲基十一-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十七-1′-基)苯酚、2,4-二甲基-6-(1 ′-甲基十三-1′-基)苯酚和其混合物。
1.2.烷基硫代甲基苯酚,例如2,4-二-辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二-辛基硫代甲基-6-乙基苯酚、2,6-二-十二基硫代甲基-4-壬基苯酚。
1.3.氢醌和烷基化氢醌,例如2,6-二-叔丁基-4-甲氧基苯酚、2,5-二-叔丁基-氢醌、2,5-二-叔戊基-氢醌、2,6-二苯基-4-十八氧基苯酚、2,6-二叔丁基氢醌、2,5-二叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟苯基硬脂酸酯、双(3,5-二-叔丁基-4-羟苯基)己二酸酯。
1.4.羟基化硫代二苯基醚,例如2,2′-硫代双(6-叔丁基-4-甲基苯酚);2,2′-硫代双(4-辛基苯酚)、4,4 ′-硫代双(6-叔丁基-3-甲基苯酚)、4,4 ′-硫代双(6-叔丁基-2-甲基苯酚)、4,4 ′-硫代双(3,6-二-仲戊基苯酚)、4,4 ′-双(2,6-二甲基-4-羟苯基)二硫化物。
1.5.亚烷基双酚,例如2,2′-亚甲基双(6-叔丁基-4-甲基酚)、2,2 ′-亚甲基双(6-叔丁基-4-乙基酚)、2,2 ′-亚甲基双〔 4-甲基-6-(α-甲基环己基)酚〕、2,2 ′-亚甲基双(4-甲基-6-环己基酚)、2,2 ′-亚甲基双(6-壬基-4-甲基酚)、2,2 ′-亚甲基双(4,6-二-叔丁基酚)、2,2 ′-亚乙基双(4,6-二-叔丁基酚、2,2 ′-亚乙基双(6-叔丁基-4-异丁基酚)、2,2′,-亚甲基双〔6-(α-甲苄基)-4-壬基酚〕、2,2′-亚甲基双〔6-(α,α-二甲苄基)-4-壬基酚〕、4,4′-亚甲基双(2,6-二-叔丁基酚〕、4,4′-亚甲基双(6-叔丁基-2-甲基酚〕、1,1-双(5-叔丁基-4-羟基-2-甲基苯基〕丁烷、2,6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲基酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二基巯基丁烷、乙二醇双〔3,3-双(3′-叔丁基-4′-羟苯基)丁酸酯〕、双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊烯、双〔2-(3 ′-叔丁基-2′-羟基-5′-甲基-苄基)-6-叔丁基-4-甲基苯基〕对苯二酸酯、1.1-双(3,5-二甲基-2-羟苯基)丁烷、2,2-双(3,5-二叔丁基-4-羟苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.6.O-、N-和S-苄基化合物,例如3,5,3′,5′-四-叔丁基-4,4′-二羟基-二苄基酯、十八基-4-羟基-3,5二甲基苄基巯基乙酸酯、三(3,5-二-叔丁基-4-羟基苄基)胺、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二酸酯、双(3,5-二-叔丁基-4-羟基苄基)硫化物、异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯。
1.7.羟苄基化的丙二酸酯,例如二一十八基-2,2-双(3,5-二-叔丁基-2-羟苄基)丙二酸酯、二一十八基-2-(3-叔丁基-4-羟基-5-甲苄基)丙二酸酯、二一十八基巯乙基-2,2-双(3,5-二-叔丁基-4-羟苄基)丙二酸酯、双(4-(1,1,3,3-四甲基丁基)-苯基〕-2,2-双(3,5-二-叔丁基-4-羟苄基)-丙二酸酯。
1.8.芳香羟苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟苄基-)-2,4,6-三甲基苯、1,4-双(3,5-二-叔丁基-4-羟苄基)-2,3,5,6-四甲基苯、3,4,6-三(3,5-二-叔丁基-4-羟苄基)苯酚。
1.9.三嗪化合物,例如2,4-双辛基巯基-6-(3,5-二-叔丁基-4-羟苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二-叔丁基-4-羟苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟苄基)异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯、2,4,6-三(3,5-二-叔丁基-4-羟苯乙基)-1,3,5-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟苯丙基)六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟苄基)异氰脲酸酯。
1.10.膦酸苄酯,例如二甲基-2,5-二-叔丁基-4-羟苄基膦酸酯、二乙基-3,5-二-叔丁基-4-羟苄基膦酸酯、二一十八基-3,5-二-叔丁基-4-羟苄基膦酸酯、二一十八基-5-叔丁基-4-羟基-3-甲苄基膦酸酯、3,5-二叔丁基-4-羟苄基膦酸-乙酯的钙盐。
1.11.酰氨基酚,例如4-羟月桂酐、4-羟硬脂酐、N-(3,5-二-叔丁基-4-羟苯基)氨基甲酸辛酯。
1.12.β-(3,5-二-叔丁基-4-羟苯基)丙酸与单或多元羟基醇形成的酯,如与甲醇、乙醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环〔2,2,2〕辛烷形成的酯。
1.13.β-(5-叔丁基-4-羟基-3-甲苯基)丙酸与单或多羟基醇形成的酯,如与甲醇、乙醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环〔2,2,2〕辛烷形成的酯。
1.14.β-(3,5-二环己基-4-羟苯基)丙酸与单或多羟基醇形成的酯,例如与甲醇、乙醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯,N,N′-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环〔2,2,2〕辛烷形成的酯。
1.15.3,5-二-叔丁基-4-羟苯基乙酸与单或多羟基醇形成的酯,如与甲醇、乙醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环〔2,2,2〕辛烷形成的酯。
1.16.β-(3,5-二-叔丁基-4-羟苯基)丙酸的酰胺,例如N,N′-双(3,5-二-叔丁基-4-羟苯基丙基)六亚甲基二胺、N,N′-双(3,5-二-叔丁基-4-羟苯基丙基)三亚甲基二胺、N,N′-双(3,5-二-叔丁基-4-羟苯基丙基)肼。
2.UV吸收剂和光稳定剂
2.1.2-(2′-羟苯基)-苯并***,例如5 ′-甲基-3′,5′-二叔丁基-、5′-叔丁基-、5′-(1,1,3,3-四甲基丁基)-、5-氯-3′,5′-二叔丁基-、5-氯-3′-叔丁基-5′-甲基-、3′-仲丁基-5′-叔丁基-、4′-辛氧基-、3′,5′-二叔戊基-、3′,5′-双(α,α-二甲苄基)-、5-氯-3 ′-叔丁基-5′-(2-辛氧基羰乙基)-与5′-氯-3′-叔丁基-5′-〔2-(2-乙基己氧基)-羰乙基〕-的混合物、5-氯-3′-叔丁基-5′-(2-甲氧基羰乙基)-、3′-叔丁基-5′-(2-甲氧基羰乙基)-、3′-叔丁基-5′-(2-辛氧基羰基乙基)-、3′-叔丁基-5′-〔 2-(2-乙基己氧基)-羰乙基〕-、3′-十二烷基-5′-甲基-和3′-叔丁丞-5′-(2-异辛氧基羰基乙基)-2′-羟苯基-2H-苯并***(2)、2,2′-亚甲基-双〔4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基酚〕;2-〔3′-叔丁基-5′-(2-甲氧羰基乙基)-2′-羟基-苯基〕-2H-苯并***与聚乙二醇300的酯基转移产物;〔R-其中R=3′-叔丁基-4′-羟基-5′-2H-苯并***-2-基苯基。
2.2.2-羟基二苯酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2′,4′-三羟基或2′-羟基-4,4′-二甲氧基衍生物。
2.3.不饱和和饱和苯甲酸的酯,例如4-叔丁基苯基水杨酸酯、苯基水杨酸酯、辛苯基水杨酸酯、二苯甲酰基间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二-叔丁基-4-羟苯甲酸的2,4-二叔丁基苯基酯、3,5-二-叔丁基-4-羟苯甲酸的十六基酯、3,5-二-叔丁基-4-羟苯甲酸的十八基酯、3,5-二-叔丁基-4-羟苯甲酸的2-甲基-4,6-二叔丁基苯基酯。
2.4.丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯。α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲酯基肉桂酸甲酯、α-氰基-β-甲基-对位甲氧基内桂酸甲酯或α-氰基-β-甲基-对位甲氧基内桂酸丁酯、a-甲酯基-对位甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基-二氢吲哚。
2.5.镍化合物,例如2,2′-硫代双〔4-(1,1,3,3-四甲基丁基)酚〕的镍复合物,如1∶1或1∶2复合物,其中可有或没有其它配体,典型的例子有正丁胺、三乙醇胺或N-环己基-二乙醇胺、二丁基二氨荒酸镍、一烷基酯的镍盐,典型的例子有4-羟基-3,5-二叔丁基苄基膦酸的甲基或乙基酯、酮肟如2-羟基-4-甲基苯基十一烷基酮肟的镍复合物、1-苯基-4-月桂酰-5-羟基-吡唑的镍复合物,其中可有或没有其它配体。
2.6.空间位阻胺,例如双(2,2,6,6-四甲基-哌啶基)癸二酸酯、双(2,2,6,6-四甲基-哌啶基)琥珀酸酯、双(1,2,2,6,6-五甲基哌啶基)癸二酸酯、正丁基-3,5-二叔丁基-4-羟苄基-丙二酸双(1,2,2,6,6-五甲基-哌啶基)酯、1-羟乙基-2,2,6,6-四甲基-4-羟基-哌啶与琥珀酸的缩合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)-六亚甲基二胺和4-叔辛氨基-2,6-二氯-1,3,5-S-***的缩合物、三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3 ,4-四燕麦酸丁酯、1,1′-(1,2-联乙基)-双(3,3,5,5-四甲基-哌嗪酮)、4-苄氧基-2,2,6,6-四甲基哌啶、4-硬酯酰氧基-2,2,6,6-四甲基哌啶、双(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺环〔4,5〕癸烷-2,4-二酮、双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-***的缩合物、2-氯-4,6-二-(4-正丁氨基-2,2,6,6-四甲基哌啶基)-1,3,5-***和1,2-双(3-氨丙基氨基)乙烷的缩合物。2-氯-4,6-二-(4-正丁基氨基-1,2,3,6,6-五甲基哌啶基)-1,3,5-***和1,2-双(3-氨丙基氨基)乙烷的缩合物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺环〔4,5〕癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮。
2.7.草酰胺,例如4,4′-二辛氧基N,N′-草酸二苯胺、2,2′-二辛氧基-5,5 ′-二-叔丁草酸二苯胺、2,2′-二-十二烷氧基-5,5 ′-二-叔丁草酸二苯胺、2-乙氧基-2′-乙草酸二苯胺、N,N′-双(3-二甲氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2′-乙草酸二苯胺和其与2-乙氧基-2′-乙基-5,4′-二-叔丁草酸二苯胺的混合物、邻-和对-甲氧基二取代的以及邻-和对-乙氧基二取代的草酸二苯胺的混合物。
2.8.2-(2-羟苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟苯基)-4,6-双(2,4-二甲苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲基苯基-1,3,5-三嗪,2-〔2-羟基-4-(2-羟基-3-丁氧基-丙氧基)苯基〕-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-〔2-羟基-4-(2-羟基-3-辛氧基-丙氧基)苯基〕-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属减活化剂,例如N,N′-二苯基草酰胺、N-水杨醛-N′-水杨酰肼、N,N′-双(水杨酰)肼、N,N′-双(3,5-二-叔丁基-4-羟苯基丙酰)肼、3-水杨酰氨基-1,2,4-***、双(亚苄基)草酸二肼、草酸二苯胺、间苯二酸二肼、癸二酸双苯肼、N,N′-二缩醛己二酸二肼、N,N′-双(水杨酰)草酸二肼、N,N′-双(水杨酰)硫代丙酸二肼。
4.亚磷酸酯和膦酸酯,例如亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、三(壬基苯基)亚磷酸酯、亚磷酸三月桂酸酯、亚磷酸三十八酯、二硬脂酰季戊四醇二亚磷酸酯、三(2,4-二-叔丁基苯基)-亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、双异癸氧基季戊四醇二亚磷酸酯、双(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂酰山梨醇三亚磷酸酯、四(2,4-二叔丁基苯基)-4,4′-亚联苯基二膦酸酯、6-异癸氧基-2,4,8,10-四-叔丁基-12H-二苯并〔d,g〕-1,3,2-二氧杂磷星、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并〔d,g〕-1,3,2-二氧杂磷星。
5.过氧化物清除剂,例如酯,典型例子包括β-硫代二丙酸的十二烷基、十八烷基、十四烷基或十三烷基酯、巯基苯并咪唑、2-巯基苯并咪唑的锌盐、二丁基二硫代甲氨酸锌、二一十八烷基二硫代物,四(β-十二烷基巯基)季戊四醇丙酸酯。
6.聚酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐及二价锰的盐。
7.碱性共稳定剂,例如蜜胺、聚乙烯吡咯烷酮、双氰胺、氰尿酸三烯丙基酯、尿素衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属和碱土金属盐、如硬脂酸钙、硬脂酸锌、二十二烷酸镁、硬脂酸镁、蓖麻醇酸钠、棕榈酸钾、焦儿茶酸锑或焦儿茶酸锡
8.成核剂,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸,
9.填料和增稠剂,例如碳酸钙、硅酸盐、玻璃纤维、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、碳黑、石墨。
10.其它添加剂,例如增塑剂、润滑剂、色素、增亮剂、阻燃剂、抗静电剂、发泡剂。
11.苯并呋喃酮或二氢吲哚酮。
除含有成分(a)和式(1)化合物外,其它优选的组合物还可包含其它添加剂,特别是酚抗氧化剂、光稳定剂和/或加工稳定剂。
特别优选的其它添加剂(稳定剂)是WO-A80/01566和EP-A415887中公开的苯并呋喃-2-酮
其中R1是苯基或被加在一起不超过18个碳原子的1至3个烷基残基、1至12个碳原子的烷氧基、2至18个碳原子的烷氧羰基或氯取代的苯基;
R2是氢;
R6是氢、1至18个碳原子的烷基、有被氧或硫原子隔开的2至18个碳原子的烷基、共含有3至16个碳原子二烷氨基烷基、环戊基、环己基、苯基或被加在一起含有不超过18个碳原子的1至3个烷基残基取代的苯基;
n是0、1或2;
取代基R7各自是氢、1至18个碳原子的烷基、环戊基、环己基、苯基、被加在一起含有不超过16个碳原子的1或2个烷基取代的苯基、有-C2H4OH,-C2H4-O-CmH2m+1或
的残基,或它们与连接氮原子一起形成哌啶子基或吗啉代残基;
m是1至18;
R10是氢、1至22个碳原子的烷基或含有5至12个碳原子的环烷基;
A是有被氮、氧或硫隔开之2至6个碳原子的亚烷基;
R8是氢、1至18个碳原子的烷基、环戊基、环己基、苯基、被加在一起不起过16个碳原子的1或2个烷基取代的苯基,或苄基;
R9是1至18个碳原子的烷基;
D是-O-、-S-、-SO-、-SO2-或C(R11)2-取代基R11各自是氢、加在一起含有不超过16个碳原子的烷基、苯基或具有式
的残基,其中n、R6和R7具有给定的定义;E是式的残基,其中R1、R2和R4具有给定的意义;且R5是氢、1至20个碳原子的烷基、环戊基、环己基、氯或具有式的残基,其中R6和R7具有给定的含义,或R5与R4一起形成四亚甲基残基。
优选的苯并呋喃-2-酮是其中R3为氢、1至12个碳原子的烷基、环戊基、环己基、氯或式
或-D-E的残基者,其中n、R6、R7、D和E的定义同上,R6较好是氢、1至18个碳原子的烷基、环戊基或环己基。
其它优选的苯并呋喃-2-酮是其中R1为苯基或被加在一起含有不超过12个碳原子的1或2个烷基取代的苯基;R2是氢;R4是氢或1至12个碳原子的烷基;R3是氢、1至12个碳原子的烷基、或-D-E:R5是氢、1至20个碳原子的烷基、或者R5与R4一起形成四亚甲基残基,且n、R6、R7、D和E的定义如前所述。
特别令人感兴趣的还有其中R1为苯基;R3为氢、1至12个碳原子的烷基或-D-E;R2和R4各目是其它氢或1至4个碳原子的烷基,且R5是1至20个碳原子的烷基,而D和E有前述定义的苯并呋喃-2-酮。
最后,更令人感兴趣的是其中R1是苯基;R3是1至4个碳原子的烷基或-D-E;R2和R4是氢;且R5是1至4个碳原子的烷基、环戊基或环己基,D是-C(R11)2-、E是式的残基的苯并呋喃-2-酮,上式中取代基R11是彼此相同或不同的,且各自是1至4个碳原子的烷基,且R1、R2、R4和R5具有给定的意义。
其它附加添加剂,特别是包括已列出的苯并呋喃-2-酮的稳定剂的量可以有很大的变化范围。它们在本发明组合物中的量一般是0.005-10%(重量),较好是0.01-5%(重量),最好是0.05-2%(重量)。
下列实施例旨在举例说明本发明化合物的制备和应用,除特别指出者外,所有百分比均为重量比。
3,9-双(1,2,2,6,6-五甲基-4-哌啶氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺环〔5,5〕十一烷的制备
于60℃下将553g(3.2mol)1,2,2,6,6-五甲基哌啶-4-醇在789.8g(7.8mol)三乙胺中制成的溶液和5.00mml甲苯逐滴加入344g(1.3mol)3,9-二氯-2,4,8,10-四氧杂-3,9-二磷杂螺环〔5,5〕十一烷在450ml甲苯中形成的溶液中。升高温度至93℃。将反应混合物回流22小时,并通过硅胶过滤。将滤液蒸发至于。
在甲苯中重新溶解部分(350g)残留物(716g),并用水和0.1M HCl洗该溶液。除去溶剂并从400ml己烷中重结晶出有机相的残留物(290g),得到201g熔点为106℃的题目化合物。
在甲苯中重新溶解第二部分未纯化的残留物,用水洗所得溶液并除去溶剂。然后从700ml乙腈中重结晶出有机相的残留物,得到240.7g熔点为106℃的题目化合物。
从200ml乙腈中重结晶出合并之母液(162.7g)残留物,进一步得到75.4g熔点为106℃的产物。
总产率为74.4%。
应用实施例1:聚丙烯的稳定化作用
将1.3Kg聚丙烯粉末(熔体指数3.2g/10分钟,测定230℃/2.16Kg)与0.05%硬脂酸钙、0.05%四(3,5-二-叔丁基-4-羟基苯基丙氧甲基)甲烷和0.05%与0.1%新的双亚磷酸酯(式1化合物)混合。在具有20mm圆柱体直径和400mm长的挤压机中挤出该掺合物,其中三个加热区分别被调整到260℃、270℃和280℃。排入水浴中冷却压出物然后制成颗粒。颗粒再挤出四次。在第1、第3和第5次挤出后,测熔体指数(230℃/2.16Kg)。结果示于表1中。
表1.干230℃第1、3和5次挤出后聚丙烯的熔体指数
双亚磷酸酯
的浓度 0.1% 0.05% 没有亚磷酸酯
熔体指数
第1次挤出后 2.3 2.4 8
第3次挤出后 2.9 3.1 15
第5次挤出后 4.0 4.4 27
(g/10分钟)
应用实施例2:高密度聚乙烯的稳定化作用
将1.3Kg用铬催化剂制备的高密度聚乙烯(d=0.940g/cm3)与表2-4中指出的不同量的Irganox1076_(3,5-二-叔丁基-4-羟苯基丙氧基十八烷)和式I的化合物相掺合。
挤压前,以190℃/5Kg测得聚乙烯熔体指数为3.0g/10分钟,以190℃/21.6Kg测得这一指数为48.1g/10分钟。在挤压期间,使用铬催化剂制备的高密度聚乙烯以一种不期望的方式发生交联。在熔体指数降低中观察到了这种方式的交联。
在一圆柱体直径为20mm、长400mm的、三个加热区分别调整到240℃、250℃和260℃的挤压机中挤压掺合物。排入水浴中冷却压出物,然后造粒。再将颗粒挤压4次。第3次和第5次挤压后,于190℃/5Kg和190℃/21.6Kg测定熔体指数。为了比较,另外还在没有新的稳定剂和没有所有添加剂的条件下,即没有新的稳定剂和没有Irganox1076_的条件下分别进行试验。结果示于表2和3中。表4还显示了在190℃测得的两个熔体指数MFI(21.6Kg)/MFI(5Kg)的比例。
表2:在190℃/21.6Kg测得的熔体指数(g/10分钟)
浓度:
式1的化合物 0.10% 0.13% 无 无
Irganox1076_ 0.0 5% 0.02% 0.15% 无
溶体指数
第1次抗压前 48.1 48.1 48.1 48.1
第3次挤压后 42.3 42.4 40.9 29.2
第5次挤压后 41.1 40.9 38.9 23.3
表3:在190℃/5Kg测得的溶体指数(9/10分钟)
浓度:式I化合物 0.10% 0.13% 无 无Irganox1076_ 0.05% 0.02% 0.15% 无熔体指数第1次挤压前 3.0 3.0 3.0 3.0第3次挤压后 2.4 2.5 2.0 0.7第5次挤压后 2.2 2.2 1.6 0.4
表4:在190℃下测得的熔体指数比例MFI(21.6Kg)/MFI(5Kg)
浓度:
式I化合物 0.10% 0.13% 无 无
Irganox1076_ 0.05% 0.02% 0.15 无
熔体指数
第1次挤压前 16.0 16.0 16.0 16.0
第3次挤压后 17.6 16.9 20.5 41.7
第5次挤压后 18.7 18.5 24.3 58.2
表2和3显示,当使用新的稳定剂时有较高熔体指数。这相当于在加工聚乙烯期间只有较低程度的不期望的交联。
表4中显示了用在21.6Kg时测得的熔体指数(表2)除以在5Kg时测得的熔体指数(表3)所得到的熔体指数比例。如果分子量分布宽,则这一比例就大。如果分子量分布窄,熔体指数比例就小。在加工期间加入稳定剂倾向于抵消分子量分布的加宽。表4的结果表明新的双亚磷酸酯以预期的方式发挥作用。
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US6521681B1 (en) * | 1996-07-05 | 2003-02-18 | Ciba Specialty Chemicals Corporation | Phenol-free stabilization of polyolefin fibres |
US7442732B2 (en) * | 2005-03-29 | 2008-10-28 | Crompton Corporation | Hindered amine light stabilizers comprising neoalkanediol phosphites |
US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
RU2562642C1 (ru) * | 2014-05-16 | 2015-09-10 | Общество с ограниченной ответственностью Научно-техническая фирма "Атомбиотех" | Реагент для нефтедобычи и способ нефтедобычи с его использованием |
RU2581070C1 (ru) * | 2015-02-19 | 2016-04-10 | Общество С Ограниченной Ответственностью "ЛУКОЙЛ-Инжиниринг" | Применение титанового коагулянта для обработки обводненного нефтяного пласта |
CN105294758A (zh) * | 2015-11-24 | 2016-02-03 | 淄博亿丰中铁高分子材料有限公司 | 亚磷酸酯抗氧剂及其制备方法 |
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GB1513629A (en) * | 1975-12-19 | 1978-06-07 | Ciba Geigy Ag | Piperidyl phosphites |
GB2014586A (en) * | 1978-02-15 | 1979-08-30 | Borg Warner | Stabilising olefin polymers against UV radiation |
US5021481A (en) * | 1989-03-21 | 1991-06-04 | Ciba-Geigy Corporation | N-hydrocarbyloxy hindered amine light stabilizers with phosphorus moieties |
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JPS5266551A (en) * | 1975-12-01 | 1977-06-02 | Adeka Argus Chem Co Ltd | Stabilizer for plastics |
IT1176167B (it) * | 1984-05-22 | 1987-08-18 | Montedison Spa | Derivati della quattro idrossi metil piperidina alchil sostituita e loro impiego come stabilizzanti |
AU3788189A (en) * | 1988-07-25 | 1990-01-25 | Borg-Warner Specialty Chemicals, Inc. | 3, 9-diphosphaspiroundecanes and process for making3, 9-diphosphaspiroundecanes |
US5023285A (en) * | 1988-07-25 | 1991-06-11 | G E Specialty Chemicals | Bis (tri-tertiary-alkylphenoxy) diphosphaspiroundecanes |
JP2653681B2 (ja) * | 1988-09-16 | 1997-09-17 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
EP0389430B1 (en) * | 1989-03-21 | 1994-10-26 | Ciba-Geigy Ag | N-hydrocarbyloxy hindered amine light stabilizers substituted with phosphorus moieties |
-
1992
- 1992-08-10 DE DE4226439A patent/DE4226439A1/de not_active Withdrawn
- 1992-08-10 SE SE9202323A patent/SE9202323L/ not_active Application Discontinuation
- 1992-08-10 GB GB9216932A patent/GB2258866B/en not_active Expired - Fee Related
- 1992-08-10 MX MX9204623A patent/MX9204623A/es unknown
- 1992-08-10 US US07/928,246 patent/US5239076A/en not_active Expired - Fee Related
- 1992-08-11 CA CA002075788A patent/CA2075788A1/en not_active Abandoned
- 1992-08-11 FR FR9209899A patent/FR2680367B1/fr not_active Expired - Fee Related
- 1992-08-11 BE BE9200712A patent/BE1007096A3/fr not_active IP Right Cessation
- 1992-08-12 RU SU925052491A patent/RU2086557C1/ru active
- 1992-08-12 BR BR929203115A patent/BR9203115A/pt not_active Application Discontinuation
- 1992-08-12 CZ CS922494A patent/CZ249492A3/cs unknown
- 1992-08-12 NL NL9201446A patent/NL9201446A/nl not_active Application Discontinuation
- 1992-08-12 IT ITMI921982A patent/IT1262011B/it active IP Right Grant
- 1992-08-12 ES ES09201692A patent/ES2044787B1/es not_active Expired - Lifetime
- 1992-08-12 SK SK2494-92A patent/SK249492A3/sk unknown
- 1992-08-12 KR KR1019920014620A patent/KR930004319A/ko not_active Application Discontinuation
- 1992-08-12 CN CN92109331A patent/CN1036275C/zh not_active Expired - Fee Related
- 1992-08-13 JP JP4237667A patent/JPH05208984A/ja active Pending
- 1992-08-18 TW TW081106536A patent/TW208018B/zh active
-
1993
- 1993-05-17 US US08/063,999 patent/US5340855A/en not_active Expired - Fee Related
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GB1513629A (en) * | 1975-12-19 | 1978-06-07 | Ciba Geigy Ag | Piperidyl phosphites |
GB2014586A (en) * | 1978-02-15 | 1979-08-30 | Borg Warner | Stabilising olefin polymers against UV radiation |
US5021481A (en) * | 1989-03-21 | 1991-06-04 | Ciba-Geigy Corporation | N-hydrocarbyloxy hindered amine light stabilizers with phosphorus moieties |
Also Published As
Publication number | Publication date |
---|---|
ES2044787A1 (es) | 1994-01-01 |
FR2680367B1 (fr) | 1994-12-02 |
KR930004319A (ko) | 1993-03-22 |
US5239076A (en) | 1993-08-24 |
CA2075788A1 (en) | 1993-02-14 |
GB2258866A (en) | 1993-02-24 |
ITMI921982A1 (it) | 1993-02-14 |
BE1007096A3 (fr) | 1995-03-14 |
SE9202323D0 (sv) | 1992-08-10 |
RU2086557C1 (ru) | 1997-08-10 |
FR2680367A1 (fr) | 1993-02-19 |
DE4226439A1 (de) | 1993-02-18 |
CN1069274A (zh) | 1993-02-24 |
TW208018B (zh) | 1993-06-21 |
GB9216932D0 (en) | 1992-09-23 |
US5340855A (en) | 1994-08-23 |
ITMI921982A0 (it) | 1992-08-12 |
JPH05208984A (ja) | 1993-08-20 |
CZ249492A3 (en) | 1993-02-17 |
SE9202323L (sv) | 1993-02-14 |
MX9204623A (es) | 1993-04-01 |
IT1262011B (it) | 1996-06-18 |
GB2258866B (en) | 1995-06-21 |
SK249492A3 (en) | 1994-12-07 |
BR9203115A (pt) | 1993-03-30 |
NL9201446A (nl) | 1993-03-01 |
ES2044787B1 (es) | 1994-06-16 |
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