CN1092785A - 用作稳定剂的低聚hals亚磷酸酯和hals亚膦酸酯 - Google Patents
用作稳定剂的低聚hals亚磷酸酯和hals亚膦酸酯 Download PDFInfo
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- CN1092785A CN1092785A CN93120897A CN93120897A CN1092785A CN 1092785 A CN1092785 A CN 1092785A CN 93120897 A CN93120897 A CN 93120897A CN 93120897 A CN93120897 A CN 93120897A CN 1092785 A CN1092785 A CN 1092785A
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- Prior art keywords
- alkyl
- represent
- phenyl
- unsubstituted
- formula
- Prior art date
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- -1 phosphorous acid ester Chemical class 0.000 title claims description 178
- 239000003381 stabilizer Substances 0.000 title claims description 15
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 31
- 239000011368 organic material Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 12
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 12
- 235000006708 antioxidants Nutrition 0.000 claims abstract description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 47
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- 150000002431 hydrogen Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 20
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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 13
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- 125000002252 acyl group Chemical group 0.000 description 7
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 5
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
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- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
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- 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
- 239000011574 phosphorus Substances 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
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- 229920002312 polyamide-imide Polymers 0.000 description 1
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 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
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 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
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride 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
- 239000007790 solid phase Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 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
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5373—Esters of phosphonic acids containing heterocyclic rings not representing cyclic esters of phosphonic 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
-
- 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
- C08L23/06—Polyethene
-
- 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
- C08L23/10—Homopolymers or copolymers of propene
- C08L23/12—Polypropene
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)
- Hydrogenated Pyridines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
新的式I低聚化合物,其中L代表下式基团:其
中基团I中的氧原子与结构重复单元中的磷原子相
连,且基团L中的R5或哌啶环的4-位上碳原子与
结构重复单元中的氧原子相连结,其它符号的定义同
权利要求1所述,该低聚化合物可作为保护有机材料
抗氧化,热或光诱导降解的稳定剂。
Description
本发明涉及新的低聚HALS亚磷酸酯和HALS亚膦酸酯,包含一种有机材料,优选聚合物,和所述新的低聚HALS亚磷酸酯和HALS亚膦酸酯的组合物,以及它们在稳定有机材料抗氧化,热或光诱导降解的应用。
现有技术中有机亚磷酸酯被认为是助稳定剂,辅助抗氧化剂和加工稳定剂,尤其用于聚烯烃。这类已知的亚磷酸酯稳定剂的实例可从R.G
chter/H.Müller(Ed.),Plastics Additives Handbook,3rd Ed.,P.47,Hanser,Munich 1990和EP-A-356688中得到。
位阻胺,特别是包括含有2,2,6,6-四甲基哌啶基基团的化合物,较可取的是其可作为抗光剂应用(受阻胺抗光剂;HALS)。
W.D.Habichey等,J.Prakt.Chem.334,333-349(1992)和GB-A-2247 241已描述了含有HALS结构单元的亚磷酸酯或亚膦酸酯。
不过仍需要对氧化,热和/或光诱导降解敏感的有机材料提供有效的稳定剂。
现已发现特定的这种HALS亚磷酸酯和HALS亚膦酸酯系特别适于作为对氧化,热或光诱发的降解敏感的有机材料的稳定剂。所述化合物特别适宜作为合成聚合物中的加工稳定剂。
更具体地讲,本发明涉及下述式Ⅰ的低聚化合物:
其中L代表下式基团:
其中基团L中的氧原子与结构重复单元中的磷原子相连结,基团L中的R5或哌啶环4-位上的碳原子与结构重复单元中的氧原子相连;R1和R2各自独立为氢,C1-25烷基,C2-C24链烯基,未取代的或C1-C4烷基-取代的C5-C8环烷基,未取代的或C1-C4烷基-取代的苯基,未取代的或C1-C4烷基-取代的C5-C8环烯基:C7-C9苯基烷基或-CH2-S-R6,
R5代表氢或甲基,
R4代表氢,C1-C25烷基,C2-C24链烯基,未取代的或C1-C4烷基取代的C5-C8环烷基,未取代的或C1-C4烷基取代的苯基,未取代的或C1-C4烷基-取代的C5-C8环烯基;C7-C9苯烷基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8,
R6代表C1-C18烷基,未取代的或C1-C4烷基取代的C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基或-(CH2)rCOOR7,
R7代表C1-C18烷基,未取代的或C1-C4烷基取代的C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;或C7-C9苯烷基,
R8代表C1-C25烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基,C1-C25链烷酰基,C3-C25链烯酰基,被氧,硫或
N-R9间断的C2-C25链烷酰基;C6-C9环烷羰基,未取代的或C1-C12烷基取代的苯甲酰基;噻吩甲酰或呋喃甲酰,
R9代表氢或C1-C8烷基,
m代表0或1,
n代表2至50的整数,
p代表0,1或2,
q代表3至8的整数,以及
r代表1或2,其条件是在式Ⅰ的结构重复单元中,L,R1,R2,R3,R4,R5,R6,R7,R8和R9以及符号m,p,p和r相同或不同。
多至25个碳原子的烷基为支链或无支链的残基且具有代表性的为甲基,乙基,丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,2-乙基丁基,正戊基,异戊基,1-甲基戊基,1,3-二甲基丁基,正己基,1-甲基己基,正庚基,异庚基,1,1,3,3-四甲基丁基,1-甲基庚基,3-甲基庚基,正辛基,2-乙基己基,1,1,3-三甲基己基,1,1,3,3-四甲基戊基,壬基,癸基,十一烷基,1-甲基十一烷基,十二烷基,1,1,3,3,5,5-六甲基己基,十三烷基,十四烷基,十五烷基,十六烷基,十七烷基,十八烷基,二十烷基或二十二烷基。优选的R1,R2,R4和R7的定义一般为C1-C18烷基,特别优选的R1,R2,R4和R7的烷基含义为C1-C4烷基。特别优选的R1,R2和R4的烷基含义为叔丁基,特别优选的R7烷基含义为甲基。
2至24碳原子的链烯基为支链或无支链的残基,如乙烯基,丙烯基,2-丁烯基,3-丁烯基,异丁烯基,正-2,4-戊二烯基,3-甲基-2-丁烯基,2-正辛烯基,2-正十二烯基,异十二烯基,油基(Oleyl),2-正十八烯基,或4-正十八烯基,优选的链烯基为3至18,更具体为3至12,一般为3至6,最优选为3至4个碳原子的链烯基。
未取代的或C1-C4烷基取代的C5-C8环烷基,特别是优选含有1至3个,更具体讲1或2个支链或无支链的烷基残基的C5-C6环烷基,一般为环戊基,甲基环戊基,二甲基环戊基,环己基,甲基环己基,二甲基环己基,三甲基环己基,叔丁基环己基,环庚基或环辛基。优选环己基和叔丁基环己基。
最好含有1至3个,更具体讲1或2个烷基基团的C1-C4烷基取代的苯基一般为邻-,间-或对-甲基苯基,2,3-二甲基苯基,2,4-二甲基苯基,2,5-二甲基苯基,2,6-二甲基苯基,3,4-二甲基苯基,3,5-二甲基苯基,2-甲基-6-乙基苯基,4-叔丁基苯基,2-乙基苯基或2,6-二乙基苯基。
未取代的或优选含有1至3个,更具体讲1或2个支链或无支链的烷基残基的C1-C4烷基取代的C5-C8环烯基一般为环戊烯基,甲基环戊烯基,二甲基环戊烯基,环己烯基,甲基环己烯基,二甲基环己烯基,三甲基环己烯基,叔丁基环己烯基,环庚烯基或环辛烯基,优选环己烯基和叔丁基环己烯基。
C7-C9苯烷基一般为苄基,α-甲基苄基,α,α-二甲基苄基或2-苯乙基。优选苄基。
C1-C18亚烷基为支链或无支链的残基,且一般为亚甲基,1,2-亚乙基,1,2-亚丙基,1,4-亚丁基,1,5-亚戊基,1,6-亚己基,1,7-亚庚基,1,8-亚辛基,1,10-亚癸基,1,12-亚十二基或1,18-亚十八基。优选C1-C8亚烷基。优选的R5的定义为1,2-亚乙基和1,2-亚丙基。
被氧,硫或
-R9间断的C2-C18亚烷基一般为-CH2-O-CH2-,-CH2-S-CH2,-CH2-NH-CH2-,-CH2-N(CH3)-CH2-,-CH2-O-CH2CH2-O-CH2-,-CH2-(O-CH2CH2-)2O-CH2-,-CH2-(O-CH2CH2-)3O-CH2-,-CH2-(O-CH2CH2-)4O-CH2-或-CH2CH2-S-CH2CH2-。
R5的C4-C8亚链烯基定义一般为2-丁烯-1,4-亚基。
未取代的或优选含有1至3个,更具体讲1或2个支链或无支链的烷基残基的C1-C4烷基取代的C5-C12环烷基一般为环戊基,甲基环戊基,二甲基环戊基,环己基,甲基环己基,二甲基环己基,三甲基环己基,叔丁基环己基,环庚基,环辛基或环癸基。优选环己基和叔丁基环己基。
含有多至25碳原子的链烷酰基为支链或无支链残基,如甲酰基,乙酰基,丙酰基,丁酰基,戊酰基,己酰基,庚酰基,辛酰基,壬酰基,癸酰基,十一酰基,十二酰基,十三酰基,十四酰基,十五酰基,十六酰基,十七酰基,十八酰基,二十酰基或二十二酰基。优选含2至18个,更具体讲2至12个,一般2至6个碳原子的链烷酰基。
3至25碳原子的链烯酰基为支链或无支链残基,如丙烯酰基,2-丁烯酰基,3-丁烯酰基,异丁烯酰基,2,4-正戊二烯酰基,3-甲基-2-丁烯酰基,2-正辛烯酰基,2-正十二碳烯酰基,异十二碳烯酰基,油酰基,2-正十八碳烯酰基或4-正十八碳烯酰基。优选含3至18个,更具体讲2至12个,一般为2至6个碳原子的链烯酰基。
被氧,硫或
-R9间断的C2-C25链烷酰基,优选C3-C25链烷酰基,一般为CH3OCO-,CH3-O-CH2-CO-,CH3-S-CH2CO-,CH3-NH-CH2CO-,CH3-N(CH3)-CH2CO-,CH3-O-CH2CH2-O-CH2CO-,CH3-(O-CH2CH2-)2O-CH2-CO-,CH3-(O-CH2CH2-)3O-CH2CO-或CH3-(O-CH2CH2-)4O-CH2-CO-。
C6-C9环烷羰基一般为环戊羰基,环己羰基,环庚羰基或环辛羰基。优选环己羰基。
优选含有1至3个,更具体讲1或2个烷基的C1-C12烷基取代的苯甲酰基一般为邻-,间-,或对-甲基苯甲酰基,2,3-二甲基苯甲酰基,2,4-二甲基苯甲酰基,2,5-二甲基苯甲酰基,2,6-二甲基苯甲酰基,3,4-二甲基苯甲酰基,3,5-二甲基苯甲酰基,2-甲基-6-乙基苯甲酰基,4-叔丁基苯甲酰基,2-乙基苯甲酰基,2,4,6-三甲基苯甲酰基,2,6-二甲基-4-叔丁基苯甲酰基或3,5-二叔丁基苯甲酰基。
优选的式Ⅰ低聚化合物是其中:
R1和R2各自独立代表氢,C1-C18烷基,C2-C18链烯基,C5-C8环烷基,未取代的或C1-C4烷基取代的苯基;C5-C8环烯基,C7-C9苯烷基或-CH2-S-R6,
R4代表氢,C1-C18烷基,C2-C18链烯基,C5-C8环烷基,未取代的或C1-C4烷基取代的苯基;C5-C8环烯基,C7-C9苯烷基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8。
R5代表C1-C12亚烷基,C4-C8亚烯基或苯亚乙基,
R6代表C1-C18烷基,C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基或-(CH2)rCOOR7,
R7代表C1-C18烷基,C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;或C7-C9苯烷基,
R8代表C1-C18烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基,C1-C18链烷酰基,C3-C18链烯酰基,被氧,硫或
N-R9间断的C2-C18链烷酰基;C6-C9环烷羰基,未取代的或C1-C4烷基取代的苯甲酰基,
R9代表氢或C1-C4烷基,和
n为2至40的整数的那些化合物。
此外优选的是其中R5代表1,2-亚乙基或1,2-亚丙基的式Ⅰ低聚化合物。
进一步优选的是那些其中R1和R2各自独立为氢或C1-C4烷基,且R5为1,2-亚乙基或1,2-亚丙基的式Ⅰ低聚化合物
特别优选的式Ⅰ低聚化合物是其中
R1和R2各自独立为氢或C1-C12烷基,C2-C12链烯基,环己基,苯基或环己烯基,
R4为氢,C1-C12烷基,C2-C12链烯基,环己基,苯基,环己烯基,苄基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8,
R5代表C1-C8亚烷基或苯亚乙基,
R6代表C1-C12烷基,C5-C8环烷基,苯基,苄基或-(CH2)rCOOR7,
R7代表C1-C12烷基,C5-C8环烷基,苯基或苄基,
R8代表C1-C12烷基,苯基,苄基,C1-C12链烷酰基,被氧间断的C2-C12链烷酰基;环己羰基或苯甲酰基,
n为2至30的整数,
p为2,
q为3至6的整数,和
r为1的那些化合物。
特别有利的式Ⅰ低聚化合物是其中
R1和R2各自独立代表氢,C1-C8烷基,环己基或苯基,
R4代表氢,C1-C8烷基,环己基或-(CH2)pCOOR7,
R5代表1,2-亚乙基,1,2-亚丙基或苯亚乙基,
R7代表C1-C12烷基或苄基,
n为2至20的整数,和
p为2的那些化合物。
更具体的有利的式Ⅰ低聚化合物是其中
R1和R2各自独立代表氢或C1-C4烷基,
R3代表氢,
R4代表氢,C1-C4烷基或-(CH2)pCOOR7,
R5代表1,2-亚乙基或1,2-亚丙基,
R7代表C1-C4烷基,
n为2至10的整数,以及
p为2的那些化合物。
新的式Ⅰ低聚化合物可按本来已知的方法制备。
优选方法一般包括使式Ⅱ化合物或式Ⅱ化合物的混合物与式Ⅲ化合物或式Ⅲ化合物的混合物反应,
其中R1,R2,R3,R4和R5及指数m的定义同式Ⅰ低聚化合物中所述。
反应在熔化状态下或在适宜的有机极性或非极性非质子传递溶剂中进行。该反应优选在碱存在下于-20℃和溶剂的沸点的温度范围内,最好在20℃至150℃范围内进行。
碱如胺也可同时用作溶剂。
可使用不同数量的碱,从经化学计算的催化量至超过式Ⅱ化合物或式Ⅲ化合物多倍摩尔量不等。反应过程中所放出的氯化氢可与碱作用转变成能够通过过滤和/或用适宜的水溶液洗涤除去的氯化物或固相。也可使用另一种与水不混溶的溶剂。产物很容易通过蒸发浓缩有机相和干燥残余物分离得到。
进行上述反应的适宜溶剂一般包括烃(如1,3,5-三甲基苯,甲苯,二甲苯,己烷,戊烷或精馏(further)石油醚部分);卤代烃(如二氯-或三氯甲烷,1,2-二氯乙烷,1,1,1-三氯乙烷或氯苯);醚(如乙醚,二丁醚或四氢呋喃),酮(如丙酮,乙基甲基酮,二乙酮,甲基丙基酮或环己酮);以及乙腈,乙酸丁酯,二甲基甲酰胺,二甲亚砜或N-甲基吡咯烷酮。
适宜的碱包括叔胺(如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二乙基苯胺或吡啶),氢化物(如锂,钠或钾的氢化物)或醇盐(如甲醇钠)。
如果使用氢化物(如氢化钠,硼氢化钠或氢化铝锂),碱金属,碱土金属的氢氧化物或甲醇钠作为碱,则首先形成式Ⅲ化合物的相应醇盐。在这种情况下反应产物(如水,甲醇)可在与式Ⅲ化合物反应之前蒸去(如以与甲苯形成的共沸物形式蒸去)。
式Ⅰ低聚化合物的结构取决于反应条件,如溶剂或反应温度,以及式Ⅱ和式Ⅲ化合物的摩尔比和浓度。
可以使用等摩尔比的式Ⅱ和式Ⅲ化合物。但是最好使用过量的式Ⅲ的HALS二醇。优选的式Ⅱ与式Ⅲ化合物的摩尔比为1∶1.05至1∶1.9。特别优选1∶1.3至1∶1.8摩尔比。
因而本发明还涉及式Ⅱ化合物或式Ⅱ化合物的混合物与式Ⅲ化合物或式Ⅲ化合物的混合物反应所能得到的低聚产物。
式Ⅲ化合物的制备是已知的。
其中m=1的式Ⅱ二氯代亚磷酸芳基酯是已知的或者可以通过本来已知的方法制备,例如尤其是DE-A-3928291中公开的方法或R.A.Bartlett等,J.Amer.Chem.Soc.109(19),5699(1987)所描述的方法。
其中m=0的式Ⅱ二氯芳基膦也是已知的或可按本来已知的方法制备,如尤其是Org.Syntheses Coll.Vol.IV,784(1963)或Th.Weil等,Helv.Chim.Acta 1952,1412或F.Nief,Tetrahedron 47(33),6673(1991)中所描述的方法。
制备新的式Ⅰ化合物所需要的式(Ⅱ)化合物可按类似上述文献的方法就地制备,而不需分离,进一步与式Ⅲ化合物反应制得式Ⅰ化合物。
式Ⅲ的HALS化合物是已知的或可按本来已知的方法制备,如尤其是US-A-4233412中所描述的方法。
式Ⅰ的结构重复单元中的L可以具有相同或不同的定义。
如式Ⅳ所示:
式Ⅰ低聚化合物的端基大部分为通过已知方法能够容易衍生的羟基基团。这些羟基基团可与酰基卤,适宜为碳酰卤或磷酰卤,或酸酐酯化;或与烷基或苄基卤烷基化或苄基化;或与异氰酸酯反应形成氨基甲酸乙酯;或与异硫氰酸酯衍生成硫代氨基甲酸乙酯;或与磺酰卤且适宜为亚硫酰氯反应生成卤化物;或与如式Ⅴ,Ⅵ或Ⅶ的氯代亚磷酸酯反应
其中R10一般为C1-C25烷基,未取代的或C1-C4烷基取代的苯基;或为C7-C9苯烷基,X和Y各自代表为氢或C1-C4烷基,或者,与所连接的碳原子一同形成3,4-脱氢环己亚基环。
式Ⅰ低聚化合物也可以式Ⅷ的环系形式得到,
其中L中的羟基端基与另一链端(-P-C1)成环,同时伴随着脱去氯化氢。
新的式Ⅰ化合物适宜稳定有机材料抗氧化,热或光诱导的降解。
这种材料的说明性实例包括:
1. 单烯类和二烯类聚合物,如聚丙烯,聚异丁烯,聚丁-1-烯,聚-4-甲基戊-1-烯,聚异戊二烯或聚丁二烯,以及环烯类聚合物,如环戊烯或降冰片烯的聚合物,聚乙烯(可任意被交联),例如高密度聚乙烯(HDPE),低密度聚乙烯(LDPE),线性低密度聚乙烯(LLDPE),支化低密度聚乙烯(BLDPE)。
聚烯烃,即前段中所述的单烯类聚合物,优选聚乙烯和聚丙烯,可用不同方法制备,特别是用下述方法制备:
a)游离基聚合反应(通常在高压和升高的温度下进行)。
b)使用通常含有一种或多种周期表中Ⅳb,Ⅴb,Ⅵb或Ⅷ族金属的催化剂的催化聚合反应。这些金属一般具有一种或多种配位体,典型的有氧化物,卤化物,醇化物,酯,醚,胺,可以是π或6-配位的烷基,链烯基和/或芳基。这些金属配合物可以为游离态或固定在底物上,一般固定在活性氯化镁,氯化钛(Ⅲ),氧化铝或氧化硅上。这些催化剂在聚合媒介中是可溶的或不可溶的。上述催化剂可单独在聚合作用中使用或可使用另外的活化剂,这些活化剂较典型的有烷基金属,金属氢化物,卤化烷基金属,烷基金属氧化物或烷基环氧乙烷合金属(metal alkyloxames),所述金属为周期表中Ⅰa,Ⅱa和/或Ⅲa族元素。活化剂可被另外的酯,醚,胺或甲硅烷基醚基团很方便地改良。这些催化剂体系通常被称作Phillips,Standard Oil Indiana,齐格勒(-纳塔),TNE(DuPont),金属茂或单一位置催化剂(SSC)。
2. 1)中所述聚合物的混合物,例如聚丙烯与聚异丁烯的混合物,聚丙烯与聚乙烯的混合物(如PP/HDPE,PP/LDPE)以及不同类型的聚乙烯混合物(如LDPE/HDPE)。
3. 单烯烃和二烯属烃彼此的共聚物或它们与其它乙烯型单体的共聚物,如乙烯/丙烯共聚物,线型低密度聚乙烯(LLDPE)和其与低密度聚乙烯(LDPE)的混合物,丙烯/丁-1-烯共聚物,丙烯/异丁烯共聚物,乙烯/丁-1-烯共聚物,乙烯/己烯共聚物,乙烯/甲基戊烯共聚物,乙烯/庚烯共聚物,乙烯/辛烯共聚物,丙烯/丁二烯共聚物,异丁烯/异戊二烯共聚物,乙烯/丙烯酸烷基酯共聚物,乙烯/异丁烯酸烷基酯共聚物,乙烯/乙酸乙烯酯共聚物和具有一氧化碳的它们的共聚物或乙烯/丙烯酸的共聚物和它们的盐(离聚物)以及乙烯与丙烯和一种二烯如己二烯,双环戊二烯或亚乙基降冰片烯的三元共聚物;以及这些共聚物相互之间或与上述1)中所述的聚合物的混合物,例如聚丙烯/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以及交联或无规聚烯/一氧化碳共聚物和它们与其它聚合物,如聚酰胺的混合物。
4. 烃类树脂(如C5-C9),包括其氢化变型(如粘合剂)和聚烯和淀粉的混合物。
5. 聚苯乙烯,聚(对-甲基苯乙烯),聚(α-甲基苯乙烯)。
6. 苯乙烯或α-甲基苯乙烯与二烯类或丙烯酸衍生物的共聚物,例如苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/异丁酸烷基酯,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/马来酐,苯乙烯/丙烯腈/丙烯酸甲酯的共聚物;高冲击强度的苯乙烯共聚物和其它聚合物的混合物,所述其它聚合物如聚丙烯酸酯,二烯类聚合物或乙烯/丙烯/二烯三元共聚物;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。
7. 苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯接枝在聚丁二烯上,苯乙烯接枝在聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上;苯乙烯和丙烯腈(或甲基丙烯腈)接枝在聚丁二烯上;苯乙烯,丙烯腈和异丁烯酸甲酯接枝在聚丁二烯上;苯乙烯和马来酐接枝在聚丁二烯上;苯乙烯,丙烯腈和马来酐或马来酰亚胺接枝在聚丁二烯上;苯乙烯和马来酰亚胺接枝在聚丁二烯上;苯乙烯和丙烯酸烷基酯或异丁烯酸烷基酯接枝在聚丁二烯上;苯乙烯和丙烯腈接枝在乙烯/丙烯/二烯三元共聚物上;苯乙烯和丙烯腈接枝在聚丙烯酸烷基酯或聚异丙烯酸烷基酯上,苯乙烯和丙烯腈接枝在丙烯酸酯/丁二烯共聚物上的接枝共聚物,以及它们与上述6)中所列共聚物的混合物,例如所述共聚物混合物被称为ABS,MBS,ASA或AES聚合物。
8. 含卤素的聚合物,如氯丁橡胶,氯化橡胶,氯化或氯磺化聚乙烯,乙烯和氯化乙烯的共聚物,3-氯-1,2-环氧丙烷均一及共聚物,特别是含卤素的乙烯基化合物的聚合物,例如聚氯乙烯,聚偏二氯乙烯,聚氟乙烯,聚偏氟乙烯,以及它们的共聚物如氯乙烯/1,1-二氯乙烯,氯乙烯/乙酸乙烯酯或1,1-二氯乙烯/乙酸乙烯酯的共聚物。
9. 由α,β-不饱和酸及其衍生物产生的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯;聚甲基丙烯酸甲酯,聚丙烯酰胺以及被丙烯酸丁酯改进冲击强度的聚丙烯腈。
10. 上述9)所述单体彼此的共聚物或它们与其它不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物,丙烯腈/丙烯酸烷基酯共聚物,丙烯腈/丙烯酸烷氧烷基或丙烯腈/乙烯基卤共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11. 由不饱和醇和胺或酰基衍生物或缩醛产生的聚合物,例如聚乙烯醇,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,聚丁酸乙烯酯,聚邻苯二甲酸烯丙酯或聚烯丙基三聚氰胺(polyallyl melamine);以及它们与上述1)中所述烯烃的共聚物。
12. 环醚的均聚物和共聚物,如聚亚烷基二醇,聚环氧乙烷,聚环氧丙烷或它们与双缩水甘油醚的共聚物。
13. 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;被热塑性聚氨酯,丙烯酸酯或MBS改性的聚缩醛。
14. 聚苯氧和聚苯硫,和聚苯氧与苯乙烯聚合物或聚酰胺的混合物。
15. 由羟基终端的聚醚,聚酯或Ⅱ端为聚丁二烯而另一端为脂族或芳族聚异氰酸酯,以及它们的前体产生的聚氨基甲酸酯。
16. 由双胺和二元羧酸产生的聚酰胺和共聚多酰胺和/或由氨基羧酸或其相应的内酰胺产生的聚酰胺和其共聚多酰胺,例如聚酰胺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,由间-二甲苯二胺与己二酸形成的芳族聚酰胺;由1,6-己二胺和间苯二酸或/和对苯二酸在或无高弹体作为改性剂存在下制得的聚酰胺,例如聚对苯二酰-2,4,4-三甲基六亚甲基二胺或聚间苯二酰间苯二胺;还包括具有聚烯烃,烯烃共聚物,离聚物或化学键合的或接枝的高弹体的上述聚酰胺的嵌段共聚物,或具有聚醚如聚乙二醇,聚丙二醇或聚丁二醇的上述聚酰胺的嵌段共聚物;以及被PDM或ABS改性的聚酰胺或共聚多酰胺;和加工过程中缩合的聚酰胺(RIM聚酰胺体系)。
17. 聚脲,聚酰亚胺,聚酰胺-酰亚胺和聚苯并咪唑。
18. 由二元羧酸和二醇和/或由羟基羧酸或相应的内酯形成的聚酯,例如聚对苯二甲酸乙二醇酯,聚对苯二甲酸丁二醇酯,聚对苯二酸1,4-二甲基环己基酯和聚羟基苯甲酸酯,以及由羟基终端的聚醚形成的嵌段共聚物;还包括被聚碳酸酯纤维或MBS改性的聚酯。
19. 聚碳酸酯纤维和聚酯碳酸酯。
20. 聚砜,聚醚砜和聚醚酮。
21. 由一端为醛且另一端为酚,脲和三聚氰胺形成的交联聚合物,如苯酚/甲醛树脂,脲/甲醛树脂和三聚氰胺/甲醛树脂。
22. 干燥和非干性醇酸树脂。
23. 由饱和和不饱和的二元羧酸与多元醇形成的共聚多酯以及作为交联剂的乙烯基化合物产生的不饱和聚酯树脂,并且以及其含卤素的低可燃性变体。
24. 由取代的丙烯酸酯形成的可交联丙烯酸树脂,例如环氧丙烯酸酯,聚氨酯丙烯酸酯或聚丙烯酸酯。
25. 醇酸树脂,聚酯树脂和被密胺树脂交联的丙烯酸树脂,尿素树脂,聚异氰酸酯或环氧树脂。
26. 由聚环氧化物如由双缩水甘油醚或环脂族双环氧化合物形成的交联环氧树脂。
27. 天然聚合物如纤维素,橡胶,明胶和它们的化学改性的同系衍生物,例如乙酸纤维素,丙酸纤维素和丁酸纤维素,或所述的纤维素醚如甲基纤维素;以及松香及其衍生物。
28. 上述聚合物的掺合物(高聚物混体),例如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/热塑性PUR,PC/热塑性PUR,POM/丙烯酸酯,POM/MBS,PPO/HIPS,PPO/PA6.6和共聚物,PA/HDPE,PA/PP,PA/PPO。
29. 天然存在的或合成的有机物,它们是纯单体化合物或这些化合物的混合物,例如矿物油,动植物脂肪,油和蜡,或以合成酯(如邻苯二甲酸酯,己二酸酯,磷酸酯或1,2,4-苯三酸酯)为基质的油,脂肪和蜡以及合成酯类与矿物油以任何重量比例形成的混合物,典型的是那些用作纺丝组合物的混合物,以及这些物料的水乳浊液。
30. 天然或合成橡胶的水乳浊液,即天然胶乳或羧基化苯乙烯/丁二烯共聚物的胶乳。
本发明还涉及含有(a)对氧化,热或光诱导的降解敏感的有机材料和(b)至少一种式Ⅰ化合物的组合物。
优选的需保护的有机材料为天然,半合成的或,更具体地讲,合成的有机材料。特别优选热塑性聚合物,更准确讲PVC或聚烯烃,最优选聚乙烯和聚丙烯。
本发明新化合物稳定有机材料抗热和氧化性降解的作用特别显著,特别是在热可塑性加工过程中受到热的作用时。因而本发明新化合物最适于作为加工稳定剂。
优选的是将式Ⅰ低聚化合物以0.01至10,一般为0.01至5,优选0.025至3,且最优选0.025至1%重量比的量加到需稳定的材料中。所述重量百分比以需稳定的有机材料的重量为基准。
除了含有式Ⅰ低聚化合物外,此新的组合物还可含有下列典型的其它共稳定剂:
1.抗氧化剂
1.1烷化一元苯酚,例如2,6-二叔丁基-4-甲基苯酚,2-叔丁基-4,6-二甲基苯酚,2,6-二叔丁基-4-乙基苯酚,2,6-二叔丁基-4-正丁基苯酚,2,6-二叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲基苯酚,2-(α-甲基环己基)-4,6-二甲基苯酚,2,6-二(十八烷基)-4-甲基苯酚,2,4,6-三环己基苯酚,2,6-二叔丁基-4-甲氧甲基苯酚,2,6-二-壬基-4-甲基苯酚,2,4-二甲基-6-(1′-甲基十一烷-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十七烷-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十三烷-1′-基)苯酚及其混合物。
1.2烷硫甲基苯酚,例如2,4-二辛硫甲基-6-叔丁基苯酚,2,6-二辛硫甲基-6-甲基苯酚,2,4-二辛硫甲基-6-乙基苯酚,2,6-二-十二烷硫基甲基-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-4-十八烷氧基苯酚,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-羟基苯基硬脂酸酯,双-(3,5-二叔丁基-4-羟基苯基)己二酸酯。
1.4羟基化硫代二苯醚,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-羟基苯基)二硫化物。
1.5亚烷基双酚类,例如2,2′-亚甲基双(6-叔丁基-4-甲基苯酚),2,2′-亚甲基双(6-叔丁基-4-乙基苯酚),2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚],2,2′-亚甲基双(4-甲基-6-环己基苯酚)2,2′-亚甲基双(6-壬基-4-甲基苯酚),2,2′-亚甲基双(4,6-二叔丁基苯酚),2,2′-亚乙基双(4,6-二叔丁基苯酚),2,2′-亚乙基双(6-叔丁基-4-异丁基苯酚),2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4′-亚甲基双(2,6-叔丁基苯酚),4,4′-亚甲基双(6-叔丁基-2-甲基苯酚),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-羟基苄基)-4-甲基苯酚,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-正十二烷硫基丁烷,乙二醇双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸酯],双(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯,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-羟基苯基)丁烷,2,2-双-(3,5-二叔丁基-4-羟基苯基)丙烷,2,2-双-(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷硫基丁烷,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-二苄基醚,十八烷基-4-羟基-3,5-二甲基苄基硫代乙酸酯,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)硫醚,异辛基-3,5-二叔丁基-4-羟基苄基硫代乙酸酯。
1.7 羟苄基化的丙二酸酯,例如二-十八烷基-2,2-双-(3,5-二叔丁基-2-羟基苄基)丙二酸酯,二-十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯,二-十二烷硫基乙基-2,2-双-(3,5-二叔丁基-4-羟基苄基)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-羟基苄基)丙二酸酯。
1.8 芳族羟苄基化合物,例如1,3,5-三-(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯,1,4-双(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯,2,4,6-(3,5-二叔丁基-4-羟基苄基)苯酚。
1.9 三嗪化合物,例如2,4-双(辛硫基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛硫基-4,6-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛硫基-4,6-双(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪,2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪,1,3,5-三-(3,5-二叔丁基-4-羟基苄基)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-羟基苯乙基)-1,3,5-三嗪,1,3,5-三(3,5-二叔丁基-4-羟苯基丙酰基)-六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯。
1.10磷酸苄酯,例如二甲基-2,5-二叔丁基-4-羟基苄基磷酸酯,二乙基-3,5-二叔丁基-4-羟基苄基磷酸酯,二-十八烷基3,5-二叔丁基-4-羟基苄基磷酸酯,二-十八烷基-5-叔丁基-4-羟基-3-甲基苄基磷酸酯,3,5-二叔丁基-4-羟基苄基磷酸单乙酯的钙盐。
1.11 酰氨基苯酚,例如4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.12 β-(3,5-二叔丁基-4-羟基苯基)丙酸与一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。
1.13 β-(5-叔丁基-4-羟基-3-甲苯基)丙酸与一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。
1.14 β-(3,5-二环己基-4-羟苯基)丙酸与一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-羟基苯基乙酸与一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。
1.16 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-羟苯基丙酰基)-1,6-亚己基二胺,N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)-1,3-亚丙基二胺,N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)肼。
2. UV吸收剂和抗光剂
2.1. 2-(2′-羟苯基)苯并三唑,例如2-(2′-羟基-5′-甲苯基)苯并三唑,2-(3′,5′-二叔丁基-2′-羟苯基)苯并三唑,2-(5′-叔丁基-2′-羟苯基)苯并三唑,2-(2′-羟基-5′-(1,1,3,3-四甲丁基)苯基)苯并三唑,2-(3′,5′-二叔丁基-2′-羟苯基)-5-氯-苯并三唑,2-(3′-叔丁基-2′-羟基-5′-甲苯基)-5-氯苯并三唑,2-(3′-仲丁基-5′-叔丁基-2′-羟苯基)苯并三唑,2-(2′-羟基-4′-辛氧苯基)苯并三唑,2-(3′,5′-二叔戊基-2′-羟苯基)苯并三唑,2-(3′,5′-双-(2,2-二甲苄基)-2′-羟苯基)苯并三唑;2-(3′-叔丁基-2′-羟基-5′-(2-辛氧羰乙基)苯基)-5-氯-苯并三唑,2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰乙基]-2′-羟苯基)-5-氯-苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-甲氧羰乙基)苯基)-5-氯-苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-甲氧羰乙基)苯基)苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-辛氧羰乙基)苯基)苯并三唑,2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰乙基]-2′-羟苯基)苯并三唑,2-(3′-十二烷基-2′-羟基-5′-甲苯基)苯并三唑,和2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧羰乙基)苯基苯并三唑的混合物,2,2′-亚甲基-双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3′-叔丁基-5′-(2-甲氧羰乙基)-2′-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯基转化产物;[R-CH2CH2-COO(CH2)3 2,其中R=3′-叔丁基-4′-羟基-5′-2H-苯并三唑-2-基苯基。
2.2. 2-羟基二苯酮,例如其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′-三羟基和2′-羟基-4,4′-二甲氧基衍生物。
2.3. 取代的和未取代的苯甲酸的酯,例如水杨酸4-叔丁基苯酯,水杨酸苯酯,水杨酸辛基苯酯,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-羟基苯甲酸2,4-二叔丁基苯酯,3,5-二叔丁基-4-羟基苯甲酸十六烷基酯,3,5-二叔丁基-4-羟基苯甲酸十八烷基酯,3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯酯。
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-甲氧基肉桂酸甲酯,α-氰基-β-甲基-对-甲氧基-肉桂酸丁酯,α-甲酯基-对-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,例如有或没有其它配体如正丁胺,三乙醇胺或N-环己基二乙醇胺的2,2′-硫代-双-[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,例如1∶1或1∶2配合物,二丁基二硫代氨基甲酸镍,单烷基酯例如4-羟基-3,5-二叔丁基苄基磷酸的甲酯或乙酯的镍盐,酮肟例如2-羟基-4-甲苯基十一烷基酮肟的镍配合物,1-苯基-4-月桂酰-5-羟基吡唑的镍配合物,并可含有或没有其它配体。
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,双(1,2,2,6,6-五甲基哌啶基)正丁基-3,5-二叔丁基-4-羟苄基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N′-双(2,2,6,6-四甲基-4-哌啶基)-1,6-亚己基二胺和4-叔辛氨基-2,6-二氯-1,3,5-三嗪的缩合物,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-丁烷-四羧酸酯,1,1′-(1,2-乙烷二基)双(3,3,5,5-四甲基哌嗪酮),4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酰氧基-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[4,5]癸-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)-1,6-亚己基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合物,2-氯-4,6-双(4-正丁氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2双(3-氨基丙氨基)乙烷的缩合物,2-氯-4,6-二-(4-正丁氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-双-(3-氨基丙氨基)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[4,5]癸-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′-二辛氧基草酰苯胺,2,2′-二辛氧基-5,5′-二叔丁基草酰苯胺,2,2′-二-十二烷氧基-5,5′-二叔丁基草酰苯胺,2-乙氧基-2′-乙草酰苯胺,N,N′-双(3-二甲氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙草酰苯胺和其与2-乙氧基-2′-乙基-5,4′-二叔丁基草酰苯胺以及邻-和对甲氧基二取代的草酰苯胺的混合物和邻-和对-乙氧基-二取代的草酰苯胺的混合物。
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-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-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-羟基苯基丙酰基)肼,3-水杨酰氨基-1,2,4-三唑,双(亚苄基)草酰基二酰肼,草酰苯胺,异邻苯二甲酰基二酰肼,癸二酰基双苯基酰肼,N,N′-二乙酰基己二酰二酰肼,N,N′-双(水杨酰)草酰二酰肼,N,N′-双(水杨酰)硫代丙酰基二酰肼。
4.亚磷酸酯和亚膦酸酯,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,亚磷酸三(壬基苯基)酯,亚磷酸三月桂基酯,亚磷酸三-十八烷基酯,二硬脂基季戊四醇二亚磷酸酯,亚磷酸三(2,4-二叔丁基苯基)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-甲苯基)-季戊四醇二亚磷酸酯,二异癸氧基季戊四醇二亚磷酸酯,双(2,4-二叔丁基-6-甲苯基)季戊四醇二亚磷酸酯,双(2,4,6-三(叔丁苯基)季戊四醇二亚磷酸酯,三硬脂基山梨醇三亚磷酸酯,四(2,4-二叔丁苯基)4,4′-亚联苯基二亚磷酸酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂辛英,6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂辛英,双(2,4-二叔丁基-6-甲苯基)甲基亚磷酸酯,双(2,4-二叔丁基-6-甲苯基)乙基亚磷酸酯。
5.过氧化物清除剂,例如β-硫代二丙酸的酯,如月桂基酯,硬脂基酯和三癸基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,二-十八烷基二硫化物,季戊四醇四(β-十二烷硫基)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和二价镁盐。
7.碱性助稳定剂,例如蜜胺,聚乙烯吡咯烷酮双氰胺,氰脲酸三烯丙酯,脲衍生物,肼衍生物,胺,聚酰胺,聚氨基甲酸乙酯,高级脂肪酸的碱金属盐和碱土金属盐例如硬脂酸钙,硬脂酸锌,山嵛酸镁,硬脂酸镁,蓖麻酸钠和棕榈酸钾,邻苯二酚锑或邻苯二酚锡。
8.成核剂,例如4-叔丁基苯甲酸,己二酸,二苯基乙酸。
9.填充剂和增强剂,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,炭黑,石墨。
10.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,荧光增白剂,耐焰剂,抗静电剂和发泡剂。
11.苯并呋喃酮和二氢吲哚酮,例如US-A-4325863,US-A-338244或US-A-175312中所公开的那些或3-[4-(2-乙酰氧乙氧基)苯基]-5,7-二叔丁基苯并呋喃-2-酮,5,7-二叔丁基-3-[4-(2-硬脂酰氧乙氧基)苯基]苯并呋喃-2-酮,3,3′-双[5,7-二叔丁基-3-(4-[2-羟乙氧基]苯基)苯并呋喃-2-酮],5,7-二叔丁基-3-(4-乙氧苯基)苯并呋喃-2-酮,3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮,3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二叔丁基-苯并呋喃-2-酮。
以被稳定材料的总量为基准,除了上述11)项所列苯并呋喃酮外,所加入光稳定剂的浓度典型为0.01-10%重量比。
除了组分(a)和式Ⅰ低聚化合物外,进一步优选的组合物还含有其它添加剂,特别是酚类防老剂,抗光剂和/或加工稳定剂。
特别优选的添加剂是酚类防老剂(第12页所列),位阻胺(第2.6项所列),亚磷酸酯和亚膦酸酯(第4项所列)和过氧化物清除剂(第5项所列)。
特别优选的其它添加剂(稳定剂)是US-A-4 325 863,US-A-4 338 244或US-A-5 175 312中公开的其它苯并呋喃-2-酮。
此类苯并呋喃-2-酮说明性实例是下式化合物
其中
R11是苯基或被1-3个总共含有不超过18个碳原子的烷基,1-12个碳原子的烷氧基,2-18个碳原子的烷氧羰基或氯取代的苯基;R12是氢;
R14是氢,1-12个碳原子的烷基,环戊基,环己基或氯;
-D-E基团,其中
R16是氢,1-18个碳原子的烷基,被氧或硫间断的2-18个碳原子烷基,含有总共3-16个碳原子的二烷氨基烷基,环戊基,环己基,苯基或被1-3个总共含有不超过18个碳原子的烷基取代的苯基,
s是0,1或2;
所述R17取代基各自独立是氢,1-18个碳原子的烷基,环戊基,环己基,苯基,被1或2个总共含有不超过16个碳原子的烷基取代的苯基,式-C2H4OH,-C2H4-O-CtH2t+1或
残基,或者与所连氮原子形成一个哌啶子基或吗啉代残基;
t是1-18;
R20是氢,1-22个碳原子的烷基或5-12个碳原子的环烷基;
A是2-22个碳原子的可被氮,氧或硫间断的亚烷基;
R18是氢,1-18个碳原子的烷基,环戊基,环己基,苯基,被1-2个总共含有不超过16个碳原子的烷基取代的苯基,或苄基;
R19是1-18个碳原子的烷基;
D是-O-,-S-,-SO-,-SO2-或-C(R11)2-;
所述R21取代基各自独立是氢,不超过16个碳原子的烷基,苯基或式
残基,其中s,R16和R17具有上述给出的定义;
E为下式残基
其中R11,R12和R14具有上述给出的定义;和
优选的苯并呋喃-2-酮为其中R13为氢,1-12个碳原子的烷基,环戊基,环己基,氯或式
或D-E残基,其中S,R16,R17,D和E如上定义,R16优选是氢,1-18个碳原子的烷基,环戊基或环己基的那些苯并呋喃-2-酮。
进一步优选的苯并呋喃-2-酮为其中R11为苯基或被1或2个总共含有不超过12个碳原子的烷基取代的苯基;R12为氢;R14为氢或1-12个碳原子的烷基;R13为氢,1-12个碳原子的烷基,或D-E;R15为氢,1-20个碳原子的烷基,
或
,或R15和R14一起形成一个1,4-亚丁基基团,其中上式中S,R16,R17,D和E具有当初定义的那些苯并呋喃-2-酮。
特别感兴趣的苯并呋喃-2-酮还可以是其中R11为苯基;R13为氢,1-12个碳原子的烷基或-D-E;R12和R14各自独立为氢或1-4个碳原子的烷基;和R15为1-20个碳原子的烷基,而D和E如当初定义的那些苯并呋喃-2-酮。
最后,应特别提到那些其中R11为苯基;R13为1-4个碳原子的烷基或-D-E;R12和R14为氢;而R15为1-4个碳原子的烷基,环戊基或环己基,D为-C(R21)2-和E为下式基团
其中各R21取代基相同或不同并分别是1-4个碳原子的烷基,R11,R12,R14和R15具有上述给出含义的苯并呋喃-2-酮。
添加苯并呋喃-2-酮的量可以在很宽的范围内变化。本发明组合物典型地含有0.0001-5%重量比,优选0.001-2%重量比,更优选0.01-2%重量比的所述添加剂。
通过已知方法很容易在成型成模制件之前或期间可将式Ⅰ化合物和其它非必需的添加剂掺和到有机聚合物中,或者可用上述化合物的溶液或分散体将有机聚合物包衣并随后蒸发溶剂。式Ⅰ低聚化合物也可以以母炼胶形式加到欲稳定的材料中,所述母炼胶较典型地包含2.5至25%重量比浓度的式Ⅰ化合物。
式Ⅰ低聚化合物也可在聚合之前或期间或者在交联之前加入。
式Ⅰ低聚化合物可以纯体形式或处于蜡,油或聚合物中的密封形式掺入到欲被稳定的材料中。
式Ⅰ低聚化合物也可以喷涂到欲稳定的聚合物上。它们能够稀释其它添加剂(典型的是列于上面的常规添加剂)或将其熔化,从而它们也能与这些添加剂一起喷涂到欲稳定的聚合物上。在聚合催化剂的减活化过程中喷涂使用是特别有利的,此时喷涂可很方便地利用用于减活化作用的蒸汽进行。
在有或没有其它添加剂的情况下,将式Ⅰ低聚化合物喷涂到球形聚合的聚合烯烃上是较便利的。
所述稳定材料可以以任何形式存在,典型的是片状物,丝状物,带状物,模制物,用于包衣组合物的成型物或粘合剂,胶粘剂或油灰状物。
如上所述,被保护的有机材料优选是有机的,更优选是合成的聚合物。特别是用于保护热塑性聚合物,优选是聚合烯烃。在这一点上,作为加工稳定剂(热稳定剂)的式Ⅰ低聚化合物的显著作用是十分明显的。为此,通常是在聚合之前或期间加入式Ⅰ化合物。而且,其也可能会稳定其它聚合物(如高弹体)或抗润滑剂和水力流体降解例如光诱导的和/或热氧化性降解。高弹体的实例可见上述例举的那些可能的有机材料。
适宜的润滑剂和水力流体可以以矿物油或合成油或其混合物为基质。润滑剂是技术人员公知的并在有关的技术文献中描述过,例如见Dieter Klamann,“Schmierstoffe und verwandte Produkte”(Lubricants and Related Products),Verlage Chemie,Weinheim,1982,Schewe-Kabek,“Das Schmiermittel-Taschenbuch”(The Lubricant Hand-book),Dr.Alfred Hüthig-Verlag,Heidelberg,1974)和“Ullmanns Enzyklopaedie der technischen Chemie”,(Encyclopedib of Industrial Chemistry),Vol.13,P85-94(Verlag Chemie,Weinheim,1977)。
因此,本发明的优选方面是式Ⅰ低聚化合物在稳定聚合物抗氧化、热或光诱导的降解作用方面的应用。
本发明还涉及一种稳定有机材料抗氧化、热或光诱导的降解作用的方法,其包括在所述材料中掺入或在所述材料涂敷上至少一种式Ⅰ低聚化合物。
本发明通过下列实施例更具体地说明,其中份数和百分比为重量比。
实施例1:低聚化合物(101)(表1)的制备
a)将42.9g(0.31mol)三氯化磷滴加到保持于50℃熔融的52.9g(0.24mol)2,4-二叔丁基-6-甲基-苯酚和580mg(4.8mmol)二甲氨基吡啶中。约1小时后,将反应混合物热至100℃并于此温度下继续搅拌3小时。于旋转蒸发仪上将过量的三氯化磷蒸掉并于高真空下将残余物蒸馏,得到70.0g(91%)无色油状2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯;b.p.95℃/0.03mbar。元素分析:计算值:C 56.09%,H 7.22%,C 122.07%。实测值:C 56.37%,H 7.20%,C 121.97%。31P-NMR(145.785 MHz,CDCl3):162.661 ppm。
b)于氮气氛下10℃将7.19g(36mmol;1.7当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶的160ml四氢呋喃溶液滴加到搅拌下的6.73g(21.0mmol)2,4-二叔丁基-6-甲基-苯基二氯亚磷酸酯(实施例1a)和6.4ml(46mmol;2.2当量)三乙胺的5ml四氢呋喃溶液中,然后将反应混合物于55-60℃搅拌3小时。白色悬浮液经硅藻土过滤,滤液于真空旋转蒸发仪上浓缩。残余物在甲苯中溶解,再一次过滤。甲苯于真空旋转蒸发仪上汽提除去,残余物于高真空下干燥,得到10.5g(77%)所要低聚化合物(101)(表1),m.p.83-86℃。
用凝胶渗透色谱法(GPC)测定重量平均分子量Mw并测得数均分子量Mn。
大体按照实施例1b所述的方法由相应的二氯代亚磷酸芳基酯和商业上可得到的二氯苯膦可制备低聚化合物(102),(103),(104)和(105)(表1)。
实施例2:低聚化合物(106)(表1)的制备
大体按照实施例1b所述的方法,由6.73g(21mmol)2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯(实施例1a)和6.34g(31.5mmol;1.5当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶可得到9.3g(98%)低聚化合物(106)(表1),m.p.90-93℃。
实施例3:低聚化合物(107)(表1)的制备
大体按照实施例1b所述的方法,由6.73g(21mmol)2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯(实施例1a)和5.5g(27.3mmol;1.3当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶可得到8.6g(91%)低聚化合物(107)(表1),m.p.92-96℃。
实施例4:低聚化合物(108)(表1)的制备
大体按照实施例1b所述的方法,由6.73g(21mmol)2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯(实施例1a)和4.65g(23mmol;1.1当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶可得到8.5g(90%)低聚化合物(108)(表1),m.p.92-95℃。
实施例5:低聚化合物(109)(表1)的制备
于氮气氛10℃将6.73g(21.0mmol)2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯(实施例1a)的10ml甲苯溶液滴加到搅拌下的7.19g(36mmol;1.7当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶和5.1g(50mmol;2.5当量)三乙胺的80ml甲苯悬浮液中,然后将反应混合物于95-100℃剧烈搅拌3小时。冷却至室温后,浓稠悬浮液经硅藻土过滤并将滤液于真空旋转蒸发仪上浓缩。残余物于真空下干燥,得9.5g(75%)低聚化合物(109)(表1)m.p.95-99℃。
大体按照此实施例所述的方法由相应的二氯代亚磷酸芳基酯和二氯芳基膦可制备低聚化合物(110),(111),(112)和(113)(表1)。
实施例6:低聚化合物(114)(表1)的制备
于室温氮气氛下将9.64g(30mmol)2,4-二叔丁基-6-甲基苯基二氯亚磷酸酯(实施例1a)的10ml二甲苯溶液滴加到搅拌下的10.98g(51mmol;1.7当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶和7.5g(75mmol;2.5当量)三乙胺的170ml二甲苯悬浮液中,然后将反应混合物于130℃搅拌5小时。冷却至室温后,浓稠悬浮液经硅藻土过滤并将滤液于真空旋转蒸发仪上浓缩。残余物经高真空下干燥,得到16.9g(92%)低聚化合物(114)(表1),m.p.55-72℃。
实施例7:低聚化合物(115)(表1)的制备
a)于氮气氛下向装有温度计,搅拌器,回流冷凝器和滴液漏斗的200ml磺化瓶中加入44.07g(0.20mol)2,4-二叔丁基-6-甲基苯酚,0.49g(4.0mmol)二甲氨基吡啶和44ml甲苯。将反应混合物加热至50℃并于此温度下于20分钟内滴加入35.7g(0.26mol;1.3当量)三氯化磷。释放出的氢氯酸气体用10%氢氧化钠水溶液中和,此后反应混合物加热95分钟至105℃并于此温度下继续搅拌30分钟(氢氯酸气体释放完)。在温和的氮气流下于105℃继续搅拌60分钟。溶液用20ml甲苯稀释,然后蒸馏除去过量的三氯化磷和约20ml甲苯。
b)氮气氛下向1.5l磺化瓶中加入68.45g(0.34mol;1.7当量)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶,46.5g(0.46mol;2.3当量)三乙胺和1000ml甲苯。于室温45分钟内向所得悬浮液中滴加上述a)溶液,将浓稠悬浮液热至105℃并于此温度下再搅拌3.5小时。反应混合物冷至室温并经硅藻土过滤。滤液于真空旋转蒸发仪上浓缩,残余物于高真空下干燥,得到82.5g(70%)白色粉状低聚化合物(115)(表1),m.p.98-99℃。
实施例8:低聚化合物(116)(表1)的制备
a)大体按照实施例7a所述的方法,将33.05g(0.15mol)2,4-二叔丁基-6-甲基苯酚,17.1ml(0.195mol)三氯化磷和0.37g(3.0mmol)二甲氨基吡啶于33ml甲苯中反应,得到相应的二氯代亚磷酸酯溶液。
b)于氮气氛下向750l磺化瓶中加入71.3g(0.255mol)N-2′-羟乙基-4-羟基-2,2,6,6-四甲基哌啶,170g三乙胺和170ml甲苯。于室温45分钟内向所得悬浮液中滴加上述a)溶液,然后将浓稠悬浮液加热至100℃并于此温度下再搅拌3.5小时。将反应混合物冷至室温并经硅藻土过滤。滤液于真空旋转蒸发仪上浓缩。残余物于高真空下干燥,得到75.0g(85%)白色粉状低聚化合物(116)(表1),m.p.92-96℃。
表1
表1(续)
表1(续)
表1(续)
实施例9:多次挤压的聚丙烯的稳定作用
将用0.025%Irganox
1076(3-[3,5-二叔丁基-4-羟基苯基]丙酸正十八烷酯(于230°/216kg测得熔体指数为3.2)预稳定的1.3kg聚丙烯粉(Profax
6501)与0.05%Irganox
1010(四-[3-(3,5-二叔丁基-4-羟基苯基)丙酸季戊四醇酯),0.05%硬脂酸钙,0.03%dihydrotalcite[DHT4A
,Kyowa Chemical Industry Co.,Ltd.,Mg4.5Al2(OH)13CO3·3,5H2O]和0.05%表1化合物掺合。然后将该掺合物于圆筒直径20mm,长400mm的挤压机上以100rpm挤压,3个加热区调至下列温度260℃,270℃,280℃。通过将压出物通过水浴而冷却,然后制成颗粒。将此颗粒重复挤压,挤压3次后测定熔体指数(230℃/2.16kg)。熔体指数的显著提高意味着明显的链降解,即不稳定。结果如表2所示。
表2
表1化合物 | 3 次挤压后熔体指数 |
-101102103104105108109111112113 | 20.04.84.64.94.84.54.85.04.94.34.6 |
实施例10:多次挤压的聚丙烯的稳定作用
将用0.025%Irganox
1076(3-[3,5-二叔丁基-4-羟基苯基]丙酸正十八烷酯(于230°/216kg测得熔体指数为3.2)预稳定的1.3kg聚丙烯粉(Profax
6501)与0.05%Irganox
1010(四-[3-(3,5-二叔丁基-4-羟基苯基)丙酸季戊四醇酯),0.05%硬脂酸钙,0.03%dihydrotalcite[DHT4A
,Kyowa Chemical Industry Co.,Ltd.,Mg4.5Al2(OH)13CO3·3,5H2O]和0.025%表1化合物掺合。然后将掺合物于圆筒直径20mm,长400mm的挤压机上以100rpm挤压,3个加热区调至下列温度260℃,270℃,280℃。通过将压出物通过水浴而冷却,然后制成颗粒。将此颗粒重复挤压,挤压3次后测定熔体指数(230℃/2.16kg)。熔体指数的显著提高意味着明显的链降解,即不稳定。结果如表3所示。
表3
表1化合物 | 3次挤压后熔体指数 |
-106107114115116 | 20.06.36.76.96.36.3 |
实施例11:加工过程中聚乙烯的稳定作用
将100份聚乙烯粉(Lupolen
5260Z)与0.05份Irganox
1010(四-[3-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯)和0.1份实施例1的稳定剂掺合。于Brabender塑性机中在220℃和50rpm下将掺合物捏合。此间连续记录作为转矩的捏合阻力。在持续恒定后聚合物开始交联的捏合期间,通过迅速提高的转矩测定捏合时间。至转矩显著提高时所用时间作为稳定作用的量度如表4所示。该时间越长稳定作用越好。
表3
表1化合物 | 转矩提高时所用时间 |
-101103105107109111115 | 5.012.012.514.014.012.512.514.5 |
Claims (19)
1、式Ⅰ低聚化合物:
其中L代表下式基团:
其中基团L中的氧原子与结构重复单元中的磷原子相连接,基团L中的R5或哌啶环4-位上的碳原子与结构重复单元中的氧原子相连;R1和R2各自独立为氢,C1-25烷基,C2-24链烯基,未取代的或C1-C4烷基-取代的C5-C8环烷基,未取代的或C1-C4烷基-取代的苯基,未取代的或C1-C4烷基-取代的C5-C8环烯基;C7-C9苯基烷基或-CH2-S-R6,
R3代表氢或甲基,
R4代表氢,C1-C25烷基,C2-C24链烯基,未取代的或C1-C4烷基取代的C5-C8环烷基,未取代的或C1-C4烷基取代的苯基,未取代的或C1-C4烷基-取代的C5-C8环烯基;C7-C9苯烷基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8,
R6代表C1-C18烷基,未取代的或C1-C4烷基取代的C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基或-(CH)rCOOR7,
R7代表C1-C18烷基,未取代的或C1-C4烷基取代的C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;或C7-C9苯烷基,
R8代表C1-C25烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基,C1-C25链烷酰基,C3-C25链烯酰基,被氧,硫或
,间断的C2-C25链烷酰基;C6-C9环烷羰基,未取代的或C1-C12烷基取代的苯甲酰基;噻吩甲酰或呋喃甲酰,
R9代表氢或C1-C8烷基,
m代表0或1,
n代表2至50的整数,
p代表0,1或2,
q代表3至8的整数,以及
r代表1或2,其条件是在式Ⅰ的结构重复单元中,L1,R1,R2,R3,R4,R5,R6,R7,R8和R9以及符号m,p,q和r相同或不同。
2、根据权利要求1的低聚化合物,其中:
R1和R2各自独立代表氢,C1-C18烷基,C2-C18链烯基,C5-C8环烷基,未取代的或C1-C4烷基取代的苯基;C5-C8环烯基,C7-C9苯烷基或-CH2-S-R6,
R4代表氢,C1-C18烷基,C2-C18链烯基,C5-C8环烷基,未取代的或C1-C4烷基取代的苯基;C5-C8环烯基,C7-C9苯烷基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8,
R5代表C1-C12亚烷基,C4-C8亚烯基或苯亚乙基,
R6代表C1-C18烷基,C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基或-(CH2)rCOOR7,
R7代表C1-C18烷基,C5-C12环烷基,未取代的或C1-C4烷基取代的苯基;或C7-C9苯烷基,
R8代表C1-C18烷基,未取代的或C1-C4烷基取代的苯基;C7-C9苯烷基,C1-C18链烷酰基,C3-C18链烯酰基,被氧,硫或
间断的C2-C18链烷酰基;C6-C9环烷羰基,未取代的或C1-C4烷基取代的苯甲酰基,
R9代表氢或C1-C4烷基,以及
n代表2至40的整数。
3、根据权利要求1的低聚化合物,其中R5代表1,2-亚乙基或1,2-亚丙基。
4、根据权利要求1的低聚化合物,其中R1和R2各自独立代表氢或C1-C4烷基,且R5代表1,2-亚乙基或1,2-亚丙基。
5、根据权利要求1的低聚化合物,其中
R1和R2各自独立代表氢或C1-C12烷基,C2-C12链烯基,环己基,苯基或环己烯基,
R4代表氢,C1-C12烷基,C2-C12链烯基,环己基,苯基,环己烯基,苄基,-CH2-S-R6,-(CH2)pCOOR7或-(CH2)qOR8,
R5代表C1-C8亚烷基或苯亚乙基,
R6代表C1-C12烷基,C5-C8环烷基,苯基,苄基或-(CH2)rCOOR7,
R7代表C1-C12烷基,C5-C8环烷基,苯基或苄基,
R8代表C1-C12烷基,苯基,苄基,C1-C12链烷酰基,被氧间断的C2-C12链烷酰基,环己羰基或苯甲酰基,
n代表2至30的整数,
p代表2,
q代表3至6的整数,以及
r代表1。
6、根据权利要求1的低聚化合物,其中
R1和R2各自独立代表氢,C1-C8烷基,环己基或苯基,
R4代表氢,C1-C8烷基,环己基或-(CH2)pCOOR7,
R5代表1,2-亚乙基,1,2-亚丙基或苯亚乙基,
R7代表C1-C12烷基或苄基,
n代表2至20的整数,和
p代表2。
7、根据权利要求1的低聚化合物,其中
R1和R2各自独立代表氢或C1-C4烷基,
R3代表氢,
R4代表氢,C1-C4烷基或-(CH2)pCOOR7,
R5代表1,2-亚乙基或1,2-亚丙基,
R7代表C1-C4烷基,
n代表2至10的整数,和
p代表2。
8、一种组合物,包含
(a)一种对氧化,热或光诱导降解敏感的有机材料,和
(b)至少一种权利要求1所述的式Ⅰ低聚化合物。
9、根据权利要求8的组合物,除组分(a)和(b)之外还包含另外的添加剂。
10、根据权利要求9的组合物,其中所述另外的添加剂选自酚类防老剂,抗光剂和加工稳定剂。
11、根据权利要求9的组合物,包括至少一种苯并呋喃-2-酮类化合物作为另外的添加剂。
12、根据权利要求8的组合物,其中组分(a)为天然,半合成或合成聚合物。
13、根据权利要求8的组合物,其中组分(a)为热塑性聚合物。
14、根据权利要求8的组合物,其中组分(a)为聚烯烃。
15、根据权利要求8的组合物,其中组分(a)为聚乙烯或聚丙烯。
16、权利要求1所限定的式Ⅰ低聚化合物作为保护有机材料抗氧化,热或光诱导的降解的稳定剂的应用。
17、权利要求16所述的式Ⅰ低聚化合物作为热塑性聚合物的加工稳定剂(热稳定剂)的应用。
18、一种稳定有机材料抗氧化,热或光诱导的降解的方法,包括向所述材料中掺入或向所述材料涂上至少一种权利要求1所述的式Ⅰ低聚化合物。
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CH3722/92-8 | 1992-12-04 | ||
CH372292 | 1992-12-04 |
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CN1092785A true CN1092785A (zh) | 1994-09-28 |
CN1036928C CN1036928C (zh) | 1998-01-07 |
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CN93120897A Expired - Fee Related CN1036928C (zh) | 1992-12-04 | 1993-12-03 | 新的低聚hals亚磷酸酯和hals亚膦酸酯,及其组合物和其对有机材料抗氧、热、光诱导降解的用途 |
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US (1) | US5405891A (zh) |
EP (1) | EP0601973B1 (zh) |
JP (1) | JPH06211988A (zh) |
KR (1) | KR940014420A (zh) |
CN (1) | CN1036928C (zh) |
AT (1) | ATE185569T1 (zh) |
BR (1) | BR9304926A (zh) |
CA (1) | CA2110550A1 (zh) |
CZ (1) | CZ284155B6 (zh) |
DE (1) | DE59309835D1 (zh) |
MX (1) | MX9307592A (zh) |
RU (1) | RU2130461C1 (zh) |
SK (1) | SK280039B6 (zh) |
TW (1) | TW252991B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101511913B (zh) * | 2006-09-08 | 2011-06-22 | 西巴控股有限公司 | 作为稳定剂的液体聚合物亚磷酸酯和亚膦酸酯 |
CN106574090A (zh) * | 2014-08-05 | 2017-04-19 | 巴斯夫欧洲公司 | 作为稳定剂的3‑苯基‑苯并呋喃‑2‑酮二亚磷酸酯衍生物 |
CN111450857A (zh) * | 2020-05-13 | 2020-07-28 | 江苏帕睿尼新材料科技有限公司 | 一种催化剂及叔丁基异硫氰酸酯的制备工艺 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5616636A (en) * | 1992-03-11 | 1997-04-01 | Sandoz Ltd. | Phosphonite-hals and phosphite-hals compounds as stabilizers |
TW350859B (en) * | 1994-04-13 | 1999-01-21 | Ciba Sc Holding Ag | HALS phosphonites as stabilizers |
TW297822B (zh) * | 1994-04-13 | 1997-02-11 | Ciba Geigy Ag | |
TW330942B (en) * | 1994-04-13 | 1998-05-01 | Ciba Sc Holding Ag | Monomeric and oligomeric bisphenyl-HALS phosphites as stabilizers |
TW338768B (en) * | 1994-06-02 | 1998-08-21 | Ciba Sc Holding Ag | Oligometic HALS phosphites and HALS phosphonites as stabilizers |
EP0707035B1 (de) * | 1994-10-12 | 1999-01-13 | Ciba SC Holding AG | HALS-Phosphorinane als Stabilisatoren |
SG91852A1 (en) * | 1998-12-21 | 2002-10-15 | Toyo Boseki | Hindered amine compound, resin composition, polyurethane fiber and production method and use thereof |
US20040030203A1 (en) * | 2002-07-16 | 2004-02-12 | Gorton Earl M. | Method of stabilizing trichloroethane during production |
US7118689B2 (en) * | 2003-08-27 | 2006-10-10 | Ppg Industries Ohio, Inc. | Stabilized polychloroethylenes |
CN101393529B (zh) * | 2008-11-07 | 2011-01-12 | 用友软件股份有限公司 | 一种实现计算机软件多语言支持的方法 |
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DE290906C (zh) * | ||||
DE2656766A1 (de) * | 1975-12-19 | 1977-07-07 | Ciba Geigy Ag | Neue phosphit-stabilisatoren |
CH626109A5 (zh) * | 1976-05-11 | 1981-10-30 | Ciba Geigy Ag | |
US4136083A (en) * | 1978-05-16 | 1979-01-23 | Eastman Kodak Company | Piperidinyl hydrogen alkylene or arylene phosphates and metal salts thereof which compounds are useful as ultraviolet stabilizers for organic compositions |
GB2042562B (en) * | 1979-02-05 | 1983-05-11 | Sandoz Ltd | Stabilising polymers |
AU3788189A (en) * | 1988-07-25 | 1990-01-25 | Borg-Warner Specialty Chemicals, Inc. | 3, 9-diphosphaspiroundecanes and process for making3, 9-diphosphaspiroundecanes |
DD290906A5 (de) * | 1988-12-30 | 1991-06-13 | Tu Dresden,Direk. Forschung,De | Verfahren zur stabilisierung von polyolefinen und deren copolymerisaten durch ester der phosphorigen und phosphonigen saeuren |
DE3928291A1 (de) * | 1989-08-26 | 1991-02-28 | Hoechst Ag | Phosphorigsaeure-arylester-amid-halogenide, phosphonigsaeurearylester-amide, verfahren zu ihrer herstellung und deren verwendung zur stabilisierung von kunststoffen |
US5175312A (en) * | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
GB2247241A (en) * | 1990-08-22 | 1992-02-26 | Sandoz Ltd | Stabilising composition for filled polymeric materials |
RU2071478C1 (ru) * | 1991-03-26 | 1997-01-10 | Циба Гейги АГ | Несимметричные арилфосфиты, полимерная композиция и способ ее получения |
-
1993
- 1993-11-06 TW TW082109565A patent/TW252991B/zh active
- 1993-11-25 DE DE59309835T patent/DE59309835D1/de not_active Expired - Fee Related
- 1993-11-25 AT AT93810823T patent/ATE185569T1/de not_active IP Right Cessation
- 1993-11-25 EP EP93810823A patent/EP0601973B1/de not_active Expired - Lifetime
- 1993-11-30 US US08/159,410 patent/US5405891A/en not_active Expired - Fee Related
- 1993-12-01 KR KR1019930026078A patent/KR940014420A/ko not_active Application Discontinuation
- 1993-12-02 SK SK1355-93A patent/SK280039B6/sk unknown
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- 1993-12-02 MX MX9307592A patent/MX9307592A/es not_active IP Right Cessation
- 1993-12-02 CZ CZ932615A patent/CZ284155B6/cs not_active IP Right Cessation
- 1993-12-03 CN CN93120897A patent/CN1036928C/zh not_active Expired - Fee Related
- 1993-12-03 BR BR9304926A patent/BR9304926A/pt not_active Application Discontinuation
- 1993-12-03 RU RU93053758A patent/RU2130461C1/ru active
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101511913B (zh) * | 2006-09-08 | 2011-06-22 | 西巴控股有限公司 | 作为稳定剂的液体聚合物亚磷酸酯和亚膦酸酯 |
CN106574090A (zh) * | 2014-08-05 | 2017-04-19 | 巴斯夫欧洲公司 | 作为稳定剂的3‑苯基‑苯并呋喃‑2‑酮二亚磷酸酯衍生物 |
CN106574090B (zh) * | 2014-08-05 | 2019-11-19 | 巴斯夫欧洲公司 | 作为稳定剂的3-苯基-苯并呋喃-2-酮二亚磷酸酯衍生物 |
CN111450857A (zh) * | 2020-05-13 | 2020-07-28 | 江苏帕睿尼新材料科技有限公司 | 一种催化剂及叔丁基异硫氰酸酯的制备工艺 |
CN111450857B (zh) * | 2020-05-13 | 2023-06-13 | 江苏帕睿尼新材料科技有限公司 | 一种催化剂及叔丁基异硫氰酸酯的制备工艺 |
Also Published As
Publication number | Publication date |
---|---|
JPH06211988A (ja) | 1994-08-02 |
US5405891A (en) | 1995-04-11 |
TW252991B (zh) | 1995-08-01 |
CZ284155B6 (cs) | 1998-08-12 |
ATE185569T1 (de) | 1999-10-15 |
SK280039B6 (sk) | 1999-07-12 |
CN1036928C (zh) | 1998-01-07 |
EP0601973B1 (de) | 1999-10-13 |
CZ261593A3 (en) | 1994-06-15 |
MX9307592A (es) | 1994-06-30 |
RU2130461C1 (ru) | 1999-05-20 |
DE59309835D1 (de) | 1999-11-18 |
SK135593A3 (en) | 1994-07-06 |
EP0601973A1 (de) | 1994-06-15 |
CA2110550A1 (en) | 1994-06-05 |
BR9304926A (pt) | 1994-07-05 |
KR940014420A (ko) | 1994-07-18 |
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