JP4490260B2 - 構造的に変性された末端基を使用した、原子移動ラジカル重合技術により製造されたポリマー - Google Patents
構造的に変性された末端基を使用した、原子移動ラジカル重合技術により製造されたポリマー Download PDFInfo
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- JP4490260B2 JP4490260B2 JP2004503522A JP2004503522A JP4490260B2 JP 4490260 B2 JP4490260 B2 JP 4490260B2 JP 2004503522 A JP2004503522 A JP 2004503522A JP 2004503522 A JP2004503522 A JP 2004503522A JP 4490260 B2 JP4490260 B2 JP 4490260B2
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- acrylic acid
- acid
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- 229920000642 polymer Polymers 0.000 title claims abstract description 158
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 title claims abstract description 37
- 238000005516 engineering process Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 25
- 239000006078 metal deactivator Substances 0.000 claims abstract description 12
- 239000007866 anti-wear additive Substances 0.000 claims abstract description 6
- 239000005069 Extreme pressure additive Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 209
- -1 alkylidene bisphenol Chemical compound 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 85
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 61
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- 239000000178 monomer Substances 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 230000003078 antioxidant effect Effects 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000003505 polymerization initiator Substances 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000005907 alkyl ester group Chemical group 0.000 claims description 11
- 239000012634 fragment Substances 0.000 claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000004185 ester group Chemical group 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 150000001350 alkyl halides Chemical group 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 4
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 4
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 4
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002199 base oil Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 claims description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
- 229930185605 Bisphenol Natural products 0.000 claims description 3
- 239000003490 Thiodipropionic acid Substances 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 239000012990 dithiocarbamate Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000005353 silylalkyl group Chemical group 0.000 claims description 3
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 claims description 3
- 235000019303 thiodipropionic acid Nutrition 0.000 claims description 3
- QLMGIWHWWWXXME-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C1=CC(CC(O)=O)=CC(C(C)(C)C)=C1O QLMGIWHWWWXXME-UHFFFAOYSA-N 0.000 claims description 2
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 claims description 2
- KDAKDBASXBEFFK-UHFFFAOYSA-N 2-(tert-butylamino)ethyl prop-2-enoate Chemical compound CC(C)(C)NCCOC(=O)C=C KDAKDBASXBEFFK-UHFFFAOYSA-N 0.000 claims description 2
- DBHUTHZPCWZNRW-UHFFFAOYSA-N 3-(3,5-dicyclohexyl-4-hydroxyphenyl)propanoic acid Chemical compound OC=1C(C2CCCCC2)=CC(CCC(=O)O)=CC=1C1CCCCC1 DBHUTHZPCWZNRW-UHFFFAOYSA-N 0.000 claims description 2
- GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 claims description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 33
- 239000000314 lubricant Substances 0.000 abstract description 31
- 229920001400 block copolymer Polymers 0.000 abstract description 13
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- 238000005260 corrosion Methods 0.000 abstract description 8
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- 230000015556 catabolic process Effects 0.000 abstract description 7
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- 238000006731 degradation reaction Methods 0.000 abstract description 7
- 101710141544 Allatotropin-related peptide Proteins 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 28
- 239000003999 initiator Substances 0.000 description 26
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- 150000001875 compounds Chemical class 0.000 description 19
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- 239000002904 solvent Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 239000003446 ligand Substances 0.000 description 11
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 10
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- 150000003839 salts Chemical class 0.000 description 7
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
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- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
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| EP02405377 | 2002-05-08 | ||
| PCT/EP2003/004449 WO2003095512A1 (en) | 2002-05-08 | 2003-04-29 | Polymers produced by atom transfer radical polymerisation technique with structurally modified terminal groups |
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| CA2584744C (en) * | 2004-10-25 | 2013-09-24 | The Lubrizol Corporation | Star polymers and compositions thereof |
| DE102005041528A1 (de) * | 2005-08-31 | 2007-03-01 | Rohmax Additives Gmbh | Öllösliche Polymere |
| EP2027236B1 (en) * | 2006-04-24 | 2016-06-08 | The Lubrizol Corporation | Star polymer lubricating composition |
| SG10201404267UA (en) * | 2006-04-24 | 2014-10-30 | Lubrizol Corp | Star Polymer Lubricating Composition |
| DE102008043674A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit einer bimodalen Molekulkargewichtsverteilung |
| US8802606B2 (en) | 2010-08-06 | 2014-08-12 | Basf Se | Lubricant composition having improved antiwear properties |
| BR112012002808B1 (pt) | 2009-08-07 | 2019-06-04 | Basf Se | Composição lubrificante, e, método para reduzir a corrosão de um artigo de aço |
| CN101845129B (zh) * | 2010-05-21 | 2012-07-04 | 中科院广州化学有限公司 | 有机硅(甲基)丙烯酸酯aba型嵌段共聚物及其制备方法和应用 |
| US8796189B2 (en) * | 2011-10-14 | 2014-08-05 | Chevron U.S.A. Inc. | Gear lubricant |
| JP5822706B2 (ja) * | 2011-12-13 | 2015-11-24 | 株式会社Adeka | 潤滑油用摩擦摩耗低減剤及びそれを含有する潤滑油組成物 |
| WO2013109907A1 (en) * | 2012-01-18 | 2013-07-25 | University Of Kansas | Drug and imaging agent delivery compositions and methods |
| WO2013116020A1 (en) * | 2012-02-03 | 2013-08-08 | Seeo, Inc | Acrylonitrile grafted to pvdf |
| CN102861558B (zh) * | 2012-09-24 | 2014-06-04 | 浙江工商大学 | 聚丙烯腈螯合树脂金属吸附材料的制备方法 |
| CN103709335B (zh) * | 2013-12-27 | 2016-03-16 | 齐鲁工业大学 | pH响应接枝共聚物及其制备方法和用途 |
| CN103880996B (zh) * | 2014-01-13 | 2016-08-17 | 盐城工学院 | 聚4-乙烯基吡啶以及基于反相细乳液aget atrp体系合成聚4-乙烯基吡啶的方法 |
| WO2018033449A1 (en) * | 2016-08-15 | 2018-02-22 | Evonik Oil Additives Gmbh | Functional polyalkyl (meth)acrylates with enhanced demulsibility performance |
| CN106263924A (zh) * | 2016-08-25 | 2017-01-04 | 费孝锋 | 一种改良结构的桌布 |
| CN106213925A (zh) * | 2016-08-25 | 2016-12-14 | 费孝锋 | 一种改进后的餐桌布 |
| CN109134788B (zh) * | 2017-06-28 | 2022-03-11 | 中国石油化工股份有限公司 | 一种端羧基sbs、制备及其在沥青改性中的应用 |
| CN107880229B (zh) * | 2017-12-08 | 2020-12-15 | 万华化学集团股份有限公司 | 一种端基改性的聚丙烯酸酯嵌段共聚物的制备方法及其制得的聚丙烯酸酯嵌段共聚物 |
| CN108755141B (zh) * | 2018-06-29 | 2021-03-12 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种粘胶纤维纺丝油剂及其制备方法 |
| CN113121778B (zh) * | 2021-05-06 | 2022-08-05 | 福建师范大学泉港石化研究院 | 一种含有改性石墨烯的聚氨酯阻燃发泡材料及其制备方法 |
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| EP0420793B1 (de) * | 1989-08-30 | 1993-11-10 | Ciba-Geigy Ag | Phenolische Verbindungen als Kettenabbrecher für die anionische Lösungspolymerisation von Dienen |
| DE69840831D1 (de) | 1997-07-28 | 2009-06-25 | Kaneka Corp | Härtbare klebstoffzusammensetzung |
| WO1999007803A1 (fr) | 1997-08-06 | 1999-02-18 | Kaneka Corporation | Composition auto-adhesive |
| CN1241195A (zh) * | 1997-08-19 | 2000-01-12 | 因芬优姆控股有限公司 | 官能化聚合物 |
| DE69921194T2 (de) * | 1998-09-29 | 2006-03-09 | Ciba Speciality Chemicals Holding Inc. | Verfahren zur herstellung von polymeren enthaltend endständige n-0 gruppen |
| US6403746B1 (en) | 1999-11-30 | 2002-06-11 | Rohmax Additives Gmbh | Method for preparation of a composition that contains polymer ester compounds with long-chain alkyl residues and use of this composition |
| DE10052646A1 (de) | 2000-10-24 | 2002-05-16 | Boettcher Henrik | Verfahren zur Herstellung von Funktionspolymeren sowie Schichten aus Funktionspolymeren auf Festkörperoberflächen über "lebende"/kontrollierte radikalische Polymerisation |
| US6576722B2 (en) | 2000-12-13 | 2003-06-10 | Ppg Industries Ohio, Inc. | Acrylic-halogenated polyolefin copolymer adhesion promoters |
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| ATE462740T1 (de) | 2010-04-15 |
| EP1501881B1 (en) | 2010-03-31 |
| EP1501881A1 (en) | 2005-02-02 |
| TWI338696B (en) | 2011-03-11 |
| CN1653101A (zh) | 2005-08-10 |
| CA2483030C (en) | 2011-03-08 |
| BR0309831B1 (pt) | 2013-09-17 |
| WO2003095512A8 (en) | 2004-10-21 |
| CN1294172C (zh) | 2007-01-10 |
| BR0309831A (pt) | 2005-02-15 |
| KR100956565B1 (ko) | 2010-05-07 |
| AU2003229749A1 (en) | 2003-11-11 |
| CA2483030A1 (en) | 2003-11-20 |
| KR20050007384A (ko) | 2005-01-17 |
| US7615522B2 (en) | 2009-11-10 |
| WO2003095512A1 (en) | 2003-11-20 |
| DE60331906D1 (de) | 2010-05-12 |
| ES2342374T3 (es) | 2010-07-06 |
| TW200403263A (en) | 2004-03-01 |
| JP2005524743A (ja) | 2005-08-18 |
| US20050272617A1 (en) | 2005-12-08 |
| AU2003229749B2 (en) | 2009-02-12 |
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