TW200909482A - Polydiorganosiloxane polyamide copolymers having organic soft segments - Google Patents
Polydiorganosiloxane polyamide copolymers having organic soft segments Download PDFInfo
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- TW200909482A TW200909482A TW97122923A TW97122923A TW200909482A TW 200909482 A TW200909482 A TW 200909482A TW 97122923 A TW97122923 A TW 97122923A TW 97122923 A TW97122923 A TW 97122923A TW 200909482 A TW200909482 A TW 200909482A
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- 239000004952 Polyamide Substances 0.000 title abstract description 8
- 229920002647 polyamide Polymers 0.000 title abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 104
- -1 polyoxypropylene residue Polymers 0.000 claims description 133
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 99
- 239000002243 precursor Substances 0.000 claims description 90
- 239000000463 material Substances 0.000 claims description 84
- 238000006243 chemical reaction Methods 0.000 claims description 76
- 150000004985 diamines Chemical class 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 45
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 239000000853 adhesive Substances 0.000 claims description 35
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 230000001070 adhesive effect Effects 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 12
- 239000006227 byproduct Substances 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 235000006408 oxalic acid Nutrition 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 238000010923 batch production Methods 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 238000011437 continuous method Methods 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 abstract description 22
- 229920000768 polyamine Polymers 0.000 description 59
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- 239000002904 solvent Substances 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 33
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- 150000001412 amines Chemical class 0.000 description 29
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229920000620 organic polymer Polymers 0.000 description 22
- 238000000576 coating method Methods 0.000 description 21
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- 239000011248 coating agent Substances 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
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- 230000008569 process Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 229920001451 polypropylene glycol Polymers 0.000 description 15
- 239000000376 reactant Substances 0.000 description 15
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000006482 condensation reaction Methods 0.000 description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
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- 125000004404 heteroalkyl group Chemical group 0.000 description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 7
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- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000013013 elastic material Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920002633 Kraton (polymer) Polymers 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000004965 chloroalkyl group Chemical group 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 3
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
- C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
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- 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
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- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/54—Nitrogen-containing linkages
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/10—Block or graft copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
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- C09J183/12—Block or graft copolymers containing polysiloxane sequences containing polyether sequences
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- C—CHEMISTRY; METALLURGY
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/00—Stock material or miscellaneous articles
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- Y10T428/1424—Halogen containing compound
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/14—Layer or component removable to expose adhesive
- Y10T428/1462—Polymer derived from material having at least one acrylic or alkacrylic group or the nitrile or amide derivative thereof [e.g., acrylamide, acrylate ester, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
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- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
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- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Polyamides (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Adhesive Tapes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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| US11/821,575 US8063166B2 (en) | 2007-06-22 | 2007-06-22 | Polydiorganosiloxane polyamide copolymers having organic soft segments |
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| US8063166B2 (en) * | 2007-06-22 | 2011-11-22 | 3M Innovative Properties Company | Polydiorganosiloxane polyamide copolymers having organic soft segments |
| US7705103B2 (en) * | 2007-06-22 | 2010-04-27 | 3M Innovative Properties Company | Polydiorganosiloxane polyoxamide copolymers |
| US20080318065A1 (en) * | 2007-06-22 | 2008-12-25 | Sherman Audrey A | Mixtures of polydiorganosiloxane polyamide-containing components and organic polymers |
| US7705101B2 (en) | 2007-06-22 | 2010-04-27 | 3M Innovative Properties Company | Branched polydiorganosiloxane polyamide copolymers |
| US8431671B2 (en) * | 2008-03-26 | 2013-04-30 | 3M Innovative Properties Company | Structured polydiorganosiloxane polyamide containing devices and methods |
| US8552136B2 (en) * | 2008-12-17 | 2013-10-08 | 3M Innovative Properties Company | Thermoplastic silicone-based polymer process additives for injection molding applications |
| CN102482426B (zh) * | 2009-09-21 | 2013-11-13 | 3M创新有限公司 | 有机硅聚乙二酰胺和有机硅聚乙二酰胺-酰肼共聚物 |
| CN102712665B (zh) * | 2009-12-30 | 2015-12-09 | 3M创新有限公司 | 含硅氧烷并含氟碳的可湿固化化合物及自其形成的聚合物 |
| WO2011082063A1 (en) * | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and polydiorganosiloxane segment |
| US8907046B2 (en) | 2009-12-30 | 2014-12-09 | 3M Innovative Properties Company | Copolymers with perfluoropolyether segment and multiple aminooxalylamino groups |
| US8765881B2 (en) | 2009-12-30 | 2014-07-01 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| CN102712750B (zh) | 2009-12-30 | 2014-06-25 | 3M创新有限公司 | 具有乙二酰胺基团的含全氟聚醚化合物 |
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| US20110202029A1 (en) * | 2010-02-16 | 2011-08-18 | The Procter & Gamble Company | Release sheet material |
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| US9540494B2 (en) | 2012-09-07 | 2017-01-10 | 3M Innovative Properties Company | Silicone compositions and related methods |
| JP2016501925A (ja) | 2012-10-29 | 2016-01-21 | スリーエム イノベイティブ プロパティズ カンパニー | ポリジオルガノシロキサンポリウレタン |
| BR112016006883A2 (pt) * | 2013-09-30 | 2017-08-01 | 3M Innovative Properties Co | composição de copolímero, adesivo sensível à pressão e método de preparo de uma composição de copolímero |
| JP2016533436A (ja) * | 2013-10-04 | 2016-10-27 | スリーエム イノベイティブ プロパティズ カンパニー | ポリジオルガノシロキサンポリアミドを含む多成分繊維、不織布ウェブ、及び物品 |
| CN103642048B (zh) * | 2013-12-02 | 2016-04-13 | 浙江科技学院 | 聚酰胺基有机硅热塑性弹性体及其制备方法 |
| EP2886581A1 (en) * | 2013-12-20 | 2015-06-24 | Siegwerk Druckfarben AG & Co. KGaA | Polyamide and its use in a release lacquer |
| US10330840B2 (en) * | 2013-12-20 | 2019-06-25 | Lg Chem, Ltd. | Optical film |
| WO2015138667A1 (en) | 2014-03-12 | 2015-09-17 | 3M Innovative Properties Company | Conductive polymeric material |
| DE102014104513A1 (de) * | 2014-03-31 | 2015-10-01 | Evonik Degussa Gmbh | Polymerzusammensetzung, Faserverbundhalbzeug und Verfahren zur Herstellung desselben |
| US10487180B2 (en) | 2014-12-08 | 2019-11-26 | 3M Innovative Properties Company | Compounds comprising modified diorganosiloxane polymers |
| CN107108880A (zh) | 2014-12-08 | 2017-08-29 | 3M创新有限公司 | 氟化硅烷化合物、组合物及制品 |
| KR20170097667A (ko) | 2014-12-22 | 2017-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 자유 라디칼 중합성 실록산 및 실록산 중합체 |
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| WO2018085066A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Silicone copolymers, methods of making, and articles |
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| WO2019043490A1 (en) * | 2017-08-31 | 2019-03-07 | 3M Innovative Properties Company | POLYDIORGANOSILOXANE-POLYOXAMIDE HYPERBRANCHED POLYMERS |
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| US2532011A (en) | 1946-09-07 | 1950-11-28 | Minnesota Mining & Mfg | Liners and adhesive tapes having low adhesion polyvinyl carbamate coatings |
| US2676182A (en) | 1950-09-13 | 1954-04-20 | Dow Corning | Copolymeric siloxanes and methods of preparing them |
| US2736721A (en) | 1952-10-08 | 1956-02-28 | Optionally | |
| US3627851A (en) | 1970-10-23 | 1971-12-14 | Dow Corning | Flexible coating composition |
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-
2007
- 2007-06-22 US US11/821,575 patent/US8063166B2/en not_active Expired - Fee Related
-
2008
- 2008-06-06 WO PCT/US2008/066047 patent/WO2009002681A1/en not_active Ceased
- 2008-06-06 JP JP2010513321A patent/JP5351148B2/ja not_active Expired - Fee Related
- 2008-06-06 CN CN2008800214821A patent/CN101687998B/zh not_active Expired - Fee Related
- 2008-06-06 EP EP08770284.1A patent/EP2167567B1/en not_active Not-in-force
- 2008-06-19 TW TW97122923A patent/TW200909482A/zh unknown
-
2011
- 2011-10-05 US US13/253,620 patent/US8361626B2/en not_active Expired - Fee Related
-
2012
- 2012-12-20 US US13/721,370 patent/US8623988B2/en not_active Expired - Fee Related
-
2013
- 2013-12-03 US US14/095,328 patent/US9018331B2/en active Active
-
2015
- 2015-03-23 US US14/665,243 patent/US9290684B2/en not_active Expired - Fee Related
-
2016
- 2016-02-10 US US15/040,598 patent/US9527965B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101687998A (zh) | 2010-03-31 |
| EP2167567B1 (en) | 2014-05-07 |
| US20080318058A1 (en) | 2008-12-25 |
| JP5351148B2 (ja) | 2013-11-27 |
| US8063166B2 (en) | 2011-11-22 |
| US8623988B2 (en) | 2014-01-07 |
| CN101687998B (zh) | 2012-11-21 |
| US8361626B2 (en) | 2013-01-29 |
| EP2167567A4 (en) | 2012-03-07 |
| US20120027976A1 (en) | 2012-02-02 |
| US20160159987A1 (en) | 2016-06-09 |
| US20140094584A1 (en) | 2014-04-03 |
| US20130109828A1 (en) | 2013-05-02 |
| US9527965B2 (en) | 2016-12-27 |
| JP2010530920A (ja) | 2010-09-16 |
| US9018331B2 (en) | 2015-04-28 |
| US9290684B2 (en) | 2016-03-22 |
| EP2167567A1 (en) | 2010-03-31 |
| WO2009002681A1 (en) | 2008-12-31 |
| US20150197675A1 (en) | 2015-07-16 |
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