JP5777635B2 - ペルフルオロポリエーテルセグメント及び複数のアミノオキサリルアミノ基を有するコポリマー - Google Patents
ペルフルオロポリエーテルセグメント及び複数のアミノオキサリルアミノ基を有するコポリマー Download PDFInfo
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- JP5777635B2 JP5777635B2 JP2012547149A JP2012547149A JP5777635B2 JP 5777635 B2 JP5777635 B2 JP 5777635B2 JP 2012547149 A JP2012547149 A JP 2012547149A JP 2012547149 A JP2012547149 A JP 2012547149A JP 5777635 B2 JP5777635 B2 JP 5777635B2
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- 229920001577 copolymer Polymers 0.000 title claims description 82
- 239000010702 perfluoropolyether Substances 0.000 title claims description 51
- -1 primary amine compound Chemical class 0.000 claims description 135
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 127
- 125000002947 alkylene group Chemical group 0.000 claims description 111
- 125000004432 carbon atom Chemical group C* 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 93
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 75
- 150000001412 amines Chemical class 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 55
- 239000011541 reaction mixture Substances 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000003107 substituted aryl group Chemical group 0.000 claims description 40
- 125000000732 arylene group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 29
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
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- 239000000047 product Substances 0.000 description 28
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- 229910052786 argon Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
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- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004965 chloroalkyl group Chemical group 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
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- 238000000518 rheometry Methods 0.000 description 3
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- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- KNURRSZDMIXZLO-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)=O KNURRSZDMIXZLO-UHFFFAOYSA-N 0.000 description 2
- CEMJPCANJOXITK-UHFFFAOYSA-N 2-oxo-2-(2,2,2-trifluoroethoxy)acetic acid Chemical compound OC(=O)C(=O)OCC(F)(F)F CEMJPCANJOXITK-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
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- 238000001308 synthesis method Methods 0.000 description 2
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- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
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- 0 C*(C)CC*CC*(C)C(*)(*)[N+]([N+]([O-])O*)[O-] Chemical compound C*(C)CC*CC*(C)C(*)(*)[N+]([N+]([O-])O*)[O-] 0.000 description 1
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- YMTUYHWOWDFXOX-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) oxalate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)C(=O)OC1=C(F)C(F)=C(F)C(F)=C1F YMTUYHWOWDFXOX-UHFFFAOYSA-N 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ULOZDEVJRTYKFE-UHFFFAOYSA-N diphenyl oxalate Chemical compound C=1C=CC=CC=1OC(=O)C(=O)OC1=CC=CC=C1 ULOZDEVJRTYKFE-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- CIYGMWIAXRMHQS-UHFFFAOYSA-N ditert-butyl oxalate Chemical compound CC(C)(C)OC(=O)C(=O)OC(C)(C)C CIYGMWIAXRMHQS-UHFFFAOYSA-N 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000004745 nonwoven fabric Substances 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
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007858 starting material Substances 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
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- GEVPIWPYWJZSPR-UHFFFAOYSA-N tcpo Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OC(=O)C(=O)OC1=C(Cl)C=C(Cl)C=C1Cl GEVPIWPYWJZSPR-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/06—Oxalic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29108309P | 2009-12-30 | 2009-12-30 | |
| US61/291,083 | 2009-12-30 | ||
| PCT/US2010/061709 WO2011082046A1 (en) | 2009-12-30 | 2010-12-22 | Copolymers with perfluorpolyether segment and multiple aminooxalylamino groups |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516516A JP2013516516A (ja) | 2013-05-13 |
| JP2013516516A5 JP2013516516A5 (enExample) | 2015-02-12 |
| JP5777635B2 true JP5777635B2 (ja) | 2015-09-09 |
Family
ID=43733351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012547149A Expired - Fee Related JP5777635B2 (ja) | 2009-12-30 | 2010-12-22 | ペルフルオロポリエーテルセグメント及び複数のアミノオキサリルアミノ基を有するコポリマー |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8907046B2 (enExample) |
| EP (1) | EP2519560B1 (enExample) |
| JP (1) | JP5777635B2 (enExample) |
| CN (1) | CN102770478B (enExample) |
| WO (1) | WO2011082046A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8765881B2 (en) | 2009-12-30 | 2014-07-01 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| EP2519530B1 (en) * | 2009-12-30 | 2014-11-19 | 3M Innovative Properties Company | Moisture-curable siloxanes and siloxane polymers |
| JP5635622B2 (ja) * | 2009-12-30 | 2014-12-03 | スリーエム イノベイティブ プロパティズ カンパニー | 水分硬化性シロキサン含有及びフルオロカーボン含有化合物、並びに該化合物から形成されるポリマー |
| WO2011082046A1 (en) * | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and multiple aminooxalylamino groups |
| WO2011082067A2 (en) * | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Perfluoropolyether-containing compounds with oxalylamino groups |
| EP2519564B1 (en) * | 2009-12-30 | 2014-10-22 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and polydiorganosiloxane segment |
| US10377857B2 (en) | 2013-12-24 | 2019-08-13 | Solvay Specialty Polymers Italy S.P.A. | Polyamides modified with (per)fluoropolyether segments |
| EP3394190B1 (en) * | 2015-12-22 | 2020-06-24 | 3M Innovative Properties Company | Oxalate ester - polyamine thermosetting compositions |
| WO2017112456A1 (en) | 2015-12-22 | 2017-06-29 | 3M Innovative Properties Company | Curable polymeric materials and methods of using same |
| US12139626B2 (en) * | 2020-01-28 | 2024-11-12 | SOCIéTé BIC | Irreversibly erasable ink composition having a discoloration agent |
| KR20240163733A (ko) * | 2022-04-27 | 2024-11-19 | 다이킨 고교 가부시키가이샤 | 플루오로폴리에테르기 함유 옥시알킬렌아미드 화합물 |
| CN115028666A (zh) * | 2022-07-28 | 2022-09-09 | 上海凌凯医药科技有限公司 | 一种呋喃糖2号位芳基氰基双取代化合物的制备方法 |
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| US3250807A (en) | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
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| NL6709067A (enExample) | 1964-04-09 | 1968-01-08 | ||
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| US3715378A (en) | 1967-02-09 | 1973-02-06 | Montedison Spa | Fluorinated peroxy polyether copolymers and method for preparing them from tetrafluoroethylene |
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| US3810874A (en) | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US4085137A (en) | 1969-03-10 | 1978-04-18 | Minnesota Mining And Manufacturing Company | Poly(perfluoroalkylene oxide) derivatives |
| US3728311A (en) | 1971-12-16 | 1973-04-17 | Du Pont | Polyureas,polyurethanes and polyamides based on a tetra-oxo diamine component |
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| US6355759B1 (en) | 1996-04-25 | 2002-03-12 | 3M Innovative Properties Company | Polydiorganosiloxane polyurea segmented copolymers and a process for making same |
| US6313335B1 (en) | 1997-11-25 | 2001-11-06 | 3M Innovative Properties | Room temperature curable silane terminated and stable waterborne polyurethane dispersions which contain fluorine and/or silicone and low surface energy coatings prepared therefrom |
| JP3729687B2 (ja) | 1999-08-04 | 2005-12-21 | 株式会社巴川製紙所 | 反射防止材料 |
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| US6923921B2 (en) | 2002-12-30 | 2005-08-02 | 3M Innovative Properties Company | Fluorinated polyether compositions |
| US20040266985A1 (en) | 2003-06-26 | 2004-12-30 | Jon Lee Howell | Nitrogenated perfluoropolyether composition |
| US7288619B2 (en) * | 2004-05-07 | 2007-10-30 | 3M Innovative Properties Company | Fluorinated polyether polyamine and method of making the same |
| CN101346649B (zh) | 2005-12-23 | 2010-09-01 | 3M创新有限公司 | 包含热塑性有机硅嵌段共聚物的膜 |
| US7371464B2 (en) | 2005-12-23 | 2008-05-13 | 3M Innovative Properties Company | Adhesive compositions |
| US20070149745A1 (en) | 2005-12-23 | 2007-06-28 | 3M Innovative Properties Company | Polydiorganosiloxane-containing materials with oxalylamino groups |
| US7501184B2 (en) * | 2005-12-23 | 2009-03-10 | 3M Innovative Properties Company | Polydiorganosiloxane polyoxamide copolymers |
| BRPI0706862A2 (pt) | 2006-01-13 | 2011-04-12 | Du Pont | composições, método de produção de refrigeração, método de produção de calor, processo de transferência de calor, processo de substituição de refrigerante ou fluido de transferência de calor, aparelho de refrigeração, aparelho de ar condicionado e aparelho de bomba de aquecimento com superfìcies de transferência de calor |
| EP2057248A2 (en) | 2006-09-01 | 2009-05-13 | E.I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| JP5056763B2 (ja) * | 2006-12-11 | 2012-10-24 | 宇部興産株式会社 | ポリアミド樹脂 |
| US7745653B2 (en) | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
| US7335786B1 (en) | 2007-03-29 | 2008-02-26 | 3M Innovative Properties Company | Michael-adduct fluorochemical silanes |
| US8063166B2 (en) * | 2007-06-22 | 2011-11-22 | 3M Innovative Properties Company | Polydiorganosiloxane polyamide copolymers having organic soft segments |
| US7705101B2 (en) | 2007-06-22 | 2010-04-27 | 3M Innovative Properties Company | Branched polydiorganosiloxane polyamide copolymers |
| US8765881B2 (en) | 2009-12-30 | 2014-07-01 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| WO2011082067A2 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Perfluoropolyether-containing compounds with oxalylamino groups |
| WO2011082046A1 (en) * | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and multiple aminooxalylamino groups |
| EP2519564B1 (en) | 2009-12-30 | 2014-10-22 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and polydiorganosiloxane segment |
| KR20130060301A (ko) * | 2010-09-17 | 2013-06-07 | 우베 고산 가부시키가이샤 | 내충격성이 우수한 폴리옥사미드 수지 및 내충격성 부품 |
-
2010
- 2010-12-22 WO PCT/US2010/061709 patent/WO2011082046A1/en not_active Ceased
- 2010-12-22 US US13/514,661 patent/US8907046B2/en not_active Expired - Fee Related
- 2010-12-22 EP EP10801529.8A patent/EP2519560B1/en not_active Not-in-force
- 2010-12-22 CN CN201080064616.5A patent/CN102770478B/zh not_active Expired - Fee Related
- 2010-12-22 JP JP2012547149A patent/JP5777635B2/ja not_active Expired - Fee Related
-
2014
- 2014-10-30 US US14/528,827 patent/US9279035B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013516516A (ja) | 2013-05-13 |
| US20120259088A1 (en) | 2012-10-11 |
| EP2519560A1 (en) | 2012-11-07 |
| US8907046B2 (en) | 2014-12-09 |
| US9279035B2 (en) | 2016-03-08 |
| CN102770478A (zh) | 2012-11-07 |
| US20150057428A1 (en) | 2015-02-26 |
| CN102770478B (zh) | 2014-03-12 |
| WO2011082046A1 (en) | 2011-07-07 |
| EP2519560B1 (en) | 2017-06-28 |
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