TWI519572B - 具有可逆交聯性能之功能性材料 - Google Patents
具有可逆交聯性能之功能性材料 Download PDFInfo
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- TWI519572B TWI519572B TW100104752A TW100104752A TWI519572B TW I519572 B TWI519572 B TW I519572B TW 100104752 A TW100104752 A TW 100104752A TW 100104752 A TW100104752 A TW 100104752A TW I519572 B TWI519572 B TW I519572B
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- formulation
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- components
- polymers
- reaction
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Links
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 101710141544 Allatotropin-related peptide Proteins 0.000 claims 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
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- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 210000001520 comb Anatomy 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000004971 Cross linker Substances 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- CQQSQBRPAJSTFB-UHFFFAOYSA-N 4-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1 CQQSQBRPAJSTFB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OAOSXODRWGDDCV-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine;4-methylbenzenesulfonic acid Chemical compound CN(C)C1=CC=NC=C1.CC1=CC=C(S(O)(=O)=O)C=C1 OAOSXODRWGDDCV-UHFFFAOYSA-N 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 2
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- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
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- 235000009518 sodium iodide Nutrition 0.000 description 2
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 2
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZBCPXYOUEIYLPQ-UHFFFAOYSA-N 1-bromo-1-[2-(1-bromo-2-methylpropoxy)ethoxy]-2-methylpropane Chemical compound BrC(C(C)C)OCCOC(C(C)C)Br ZBCPXYOUEIYLPQ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DEBZEVJNWCNATM-MZWXYZOWSA-N 2,2,4,4,6,6-hexakis(deuteriomethyl)-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene Chemical compound [2H]CP1(C[2H])=NP(C[2H])(C[2H])=NP(C[2H])(C[2H])=N1 DEBZEVJNWCNATM-MZWXYZOWSA-N 0.000 description 1
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- GTOHSWJMILPTPK-UHFFFAOYSA-N C=CC.C=CC.C=CC.C=CC.[Ti] Chemical group C=CC.C=CC.C=CC.C=CC.[Ti] GTOHSWJMILPTPK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- UWTASUKCZNGRDU-UHFFFAOYSA-N Met-Arg-Phe-Ala acetate salt Chemical compound CSCCC(N)C(=O)NC(CCCN=C(N)N)C(=O)NC(C(=O)NC(C)C(O)=O)CC1=CC=CC=C1 UWTASUKCZNGRDU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
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- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
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- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- KZPXREABEBSAQM-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel(2+) Chemical compound [Ni+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KZPXREABEBSAQM-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000011089 mechanical engineering Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
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- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
- C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010001987A DE102010001987A1 (de) | 2010-02-16 | 2010-02-16 | Funktionsmaterialien mit reversibler Vernetzung |
Publications (2)
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| TW201141919A TW201141919A (en) | 2011-12-01 |
| TWI519572B true TWI519572B (zh) | 2016-02-01 |
Family
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| TW100104752A TWI519572B (zh) | 2010-02-16 | 2011-02-14 | 具有可逆交聯性能之功能性材料 |
Country Status (13)
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| US (1) | US8916635B2 (https=) |
| EP (1) | EP2536797B1 (https=) |
| JP (1) | JP5855021B2 (https=) |
| CN (1) | CN102844391B (https=) |
| AU (1) | AU2011217504A1 (https=) |
| BR (1) | BR112012020564A2 (https=) |
| CA (1) | CA2789841C (https=) |
| DE (1) | DE102010001987A1 (https=) |
| DK (1) | DK2536797T3 (https=) |
| ES (1) | ES2635083T3 (https=) |
| PL (1) | PL2536797T3 (https=) |
| TW (1) | TWI519572B (https=) |
| WO (1) | WO2011101176A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102010001992A1 (de) | 2010-02-16 | 2011-08-18 | Evonik Röhm GmbH, 64293 | Funktionsmaterialien mit steuerbarer Viskosität |
| DE102010040282A1 (de) | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Funktionsmaterialien mit steuerbarer Viskosität bzw. reversibler Vernetzung über Aza-Diels-Alder-Reaktionen mit Bishydrazonen oder konjugierten Bis-Schiff'schen Basen |
| DE102010044025A1 (de) | 2010-11-17 | 2012-05-24 | Evonik Röhm Gmbh | Materialien mit steuerbarem Vernetzungsgrad |
| EP2661459B1 (de) | 2011-01-04 | 2016-06-08 | Evonik Degussa GmbH | Composite-halbzeuge und daraus hergestellte formteile sowie direkt hergestellte formteile auf basis von hydroxyfunktionalisierten (meth) acrylaten, die mittels uretdionen duroplastisch vernetzt werden |
| DE102011079812A1 (de) | 2011-07-26 | 2013-01-31 | Evonik Röhm Gmbh | Polymerpulver zur Herstellung dreidimensionaler Objekte |
| DE102011080131A1 (de) | 2011-07-29 | 2013-01-31 | Evonik Degussa Gmbh | Niedermolekulare Produkte, und deren Verwendung als reversible oder permanente Niedertemperatur-Vernetzer bei Diels-Alder-Reaktionen |
| DE102011086502A1 (de) * | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung ungefärbter Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011086503A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung von kohäsiven Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011087226A1 (de) | 2011-11-28 | 2013-05-29 | Evonik Degussa Gmbh | Pseudo-thermoplastische, selbstvernetzende Composites |
| DE102012200235A1 (de) | 2012-01-10 | 2013-07-11 | Evonik Industries Ag | Photoinduzierte Vernetzung von Doppelbindungen-enthaltenden Polymeren mittels pericyclischer Reaktion |
| EP2740755A1 (en) * | 2012-12-07 | 2014-06-11 | Fonds de l'ESPCI - Georges Charpak | Processable semi-crystalline polymer networks |
| DE102012222742A1 (de) * | 2012-12-11 | 2014-03-27 | Evonik Industries Ag | Funktionsmaterialien mit reversibler Vernetzung |
| JP5594352B2 (ja) | 2012-12-13 | 2014-09-24 | 横浜ゴム株式会社 | 分子中に二重結合を有するゴム組成物 |
| US20160304683A1 (en) * | 2013-11-19 | 2016-10-20 | Evonik Degussa Gmbh | Mouldings based on diene-functionalized (meth)acrylates and (hetero-)diels-alder dienophiles, with reversible crosslinking |
| EP2982704A1 (de) | 2014-08-06 | 2016-02-10 | Evonik Degussa GmbH | Reversibel vernetzte Polymeremulsionen |
| EP2982503A1 (de) * | 2014-08-07 | 2016-02-10 | Evonik Röhm GmbH | Sandwich-Bauteile aus Poly(Meth)acrylat-basierten Schaumkörpern und reversibel vernetzbaren Composites |
| JP2016037571A (ja) * | 2014-08-08 | 2016-03-22 | Jsr株式会社 | 造形用樹脂組成物及び造形用フィラメント |
| JP6568218B2 (ja) | 2014-12-23 | 2019-08-28 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | 化学線硬化型高分子混合物、硬化高分子混合物、及び関連するプロセス |
| EP3053905A1 (de) | 2015-02-04 | 2016-08-10 | Evonik Degussa GmbH | Durch sichtbares Licht induzierte Zykloaddition zur Polymerisation bzw. Vernetzung mittels Azirin-Verbindungen |
| US11097531B2 (en) | 2015-12-17 | 2021-08-24 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
| EP3181652B1 (fr) * | 2015-12-18 | 2019-02-27 | The Swatch Group Research and Development Ltd. | Procédé d'assemblage et de repositionnement de pièces horlogères en utilisant un adhésif repositionnable à chaud |
| EP3181651B1 (fr) * | 2015-12-18 | 2019-02-06 | The Swatch Group Research and Development Ltd. | Ensemble de pièces horlogères assemblées par adhésif repositionnable à chaud et procédé d'assemblage et de repositionnement de telles pièces |
| EP3199575A1 (de) | 2016-01-29 | 2017-08-02 | Evonik Degussa GmbH | Neuartiger hetero-diels-alder-vernetzer und deren verwendung in reversibel vernetzenden polymersystemen |
| CN105694790B (zh) * | 2016-02-29 | 2018-06-29 | 中国工程物理研究院材料研究所 | 一种可快速拆解的环氧胶粘剂及其制备和拆解方法 |
| DE102016104071B4 (de) | 2016-03-07 | 2018-10-25 | Groz-Beckert Kg | Verfahren zum Biegen eines Bewehrungsstabes eines Bewehrungselements sowie Biegevorrichtung |
| WO2018054684A1 (de) | 2016-09-20 | 2018-03-29 | Evonik Degussa Gmbh | Neuartiger vernetzer-baustein für die verwendung in reversibel vernetzenden polymersystemen |
| EP3296347A1 (de) | 2016-09-20 | 2018-03-21 | Evonik Degussa GmbH | Neuartiger dien-baustein für die verwendung in reversibel vernetzenden (hetero-)diels-alder-polymersystemen |
| US11453161B2 (en) | 2016-10-27 | 2022-09-27 | Bridgestone Americas Tire Operations, Llc | Processes for producing cured polymeric products by additive manufacturing |
| DE102017120143A1 (de) | 2017-09-01 | 2019-03-07 | Groz-Beckert Kg | Biegeverfahren und Biegevorrichtung zum Biegen eines Verbundwerkstoffstabes |
| DE102017120624A1 (de) | 2017-09-07 | 2019-03-07 | Groz-Beckert Kg | Textilbewehrungsanordnung, Verfahren zu dessen Herstellung sowie Trenn- und/oder Formgebungseinrichtung zur Verwendung bei diesem Verfahren |
| DE102017131236A1 (de) * | 2017-12-22 | 2019-06-27 | Bundesrepublik Deutschland, Vertreten Durch Den Bundesminister Für Wirtschaft Und Energie, Dieser Vertreten Durch Den Präsidenten Der Bundesanstalt Für Materialforschung Und -Prüfung (Bam) | Verfahren zur herstellung von klebflächen mittels einer 3d-druckvorrichtung |
| US20210230781A1 (en) * | 2018-06-08 | 2021-07-29 | Cummins Filtration Ip, Inc. | Cross-linked non-wovens produced by melt blowing reversible polymer networks |
| CN112778548B (zh) * | 2019-11-04 | 2022-10-21 | 中国石油化工股份有限公司 | 可逆交联的脂肪族聚酯及其制备方法 |
| WO2021201228A1 (ja) * | 2020-04-01 | 2021-10-07 | 出光興産株式会社 | 樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、成形物、電子デバイス、および電子写真感光体の製造方法 |
| WO2025090402A1 (en) * | 2023-10-23 | 2025-05-01 | Geisys Ventures, LLC | Debondable adhesive |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047910A1 (en) * | 1997-04-21 | 1998-10-29 | Proligo Llc | Method for solution phase synthesis of oligonucleotides |
| JP4031866B2 (ja) * | 1998-06-16 | 2008-01-09 | 横浜ゴム株式会社 | リサイクル性エラストマー |
| DE19832629A1 (de) | 1998-07-21 | 2000-02-03 | Daimler Chrysler Ag | Klebstoffsystem zur Bildung reversibler Klebeverbindungen |
| DE19961940A1 (de) | 1999-12-22 | 2001-08-02 | Henkel Kgaa | Lösbare Klebeverindungen |
| US6933361B2 (en) | 2002-07-12 | 2005-08-23 | The Regents Of The University Of California | Thermally re-mendable cross-linked polymers |
| US7309754B2 (en) * | 2003-09-26 | 2007-12-18 | Hitachi Global Storage Technologies Netherlands B.V. | Stable encapsulant fluid capable of undergoing reversible Diels-Alder polymerization |
| US20050159521A1 (en) | 2004-01-20 | 2005-07-21 | Brown Donald A. | Reversible adhesive |
| JP2006193628A (ja) * | 2005-01-14 | 2006-07-27 | Yokohama Rubber Co Ltd:The | 共役ジエン化合物、硬化性組成物およびその硬化物 |
| US8685528B2 (en) | 2007-04-20 | 2014-04-01 | GM Global Technology Operations LLC | Shape memory polymer and adhesive combination and methods of making and using the same |
| US7976665B2 (en) | 2007-10-04 | 2011-07-12 | GM Global Technology Operations LLC | Method of minimizing residue adhesion for thermo-reversible dry adhesives |
| EP2062926A1 (de) | 2007-11-21 | 2009-05-27 | Sika Technology AG | Polyurethanpolymer für reversible Klebeverbindungen |
| EP2166030A1 (en) * | 2008-09-19 | 2010-03-24 | Rijksuniversiteit Groningen | Re-mouldable cross-linked resin, a composition, a substituted furan, and processes for preparing the same |
| ES2539184T3 (es) * | 2009-06-11 | 2015-06-26 | Henkel IP & Holding GmbH | Composición adhesiva termofusible térmicamente reversible que contiene compuestos de dieno y dienófilos multifuncionales |
| DE102010040282A1 (de) | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Funktionsmaterialien mit steuerbarer Viskosität bzw. reversibler Vernetzung über Aza-Diels-Alder-Reaktionen mit Bishydrazonen oder konjugierten Bis-Schiff'schen Basen |
| DE102010044025A1 (de) | 2010-11-17 | 2012-05-24 | Evonik Röhm Gmbh | Materialien mit steuerbarem Vernetzungsgrad |
| EP2661459B1 (de) | 2011-01-04 | 2016-06-08 | Evonik Degussa GmbH | Composite-halbzeuge und daraus hergestellte formteile sowie direkt hergestellte formteile auf basis von hydroxyfunktionalisierten (meth) acrylaten, die mittels uretdionen duroplastisch vernetzt werden |
| DE102011080131A1 (de) | 2011-07-29 | 2013-01-31 | Evonik Degussa Gmbh | Niedermolekulare Produkte, und deren Verwendung als reversible oder permanente Niedertemperatur-Vernetzer bei Diels-Alder-Reaktionen |
-
2010
- 2010-02-16 DE DE102010001987A patent/DE102010001987A1/de not_active Withdrawn
-
2011
- 2011-01-04 ES ES11700157.8T patent/ES2635083T3/es active Active
- 2011-01-04 US US13/577,932 patent/US8916635B2/en not_active Expired - Fee Related
- 2011-01-04 CA CA2789841A patent/CA2789841C/en not_active Expired - Fee Related
- 2011-01-04 CN CN201180007005.1A patent/CN102844391B/zh not_active Expired - Fee Related
- 2011-01-04 EP EP11700157.8A patent/EP2536797B1/de not_active Not-in-force
- 2011-01-04 AU AU2011217504A patent/AU2011217504A1/en not_active Abandoned
- 2011-01-04 BR BR112012020564A patent/BR112012020564A2/pt not_active Application Discontinuation
- 2011-01-04 JP JP2012553236A patent/JP5855021B2/ja not_active Expired - Fee Related
- 2011-01-04 WO PCT/EP2011/050043 patent/WO2011101176A1/de not_active Ceased
- 2011-01-04 PL PL11700157T patent/PL2536797T3/pl unknown
- 2011-01-04 DK DK11700157.8T patent/DK2536797T3/en active
- 2011-02-14 TW TW100104752A patent/TWI519572B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011101176A9 (de) | 2012-08-16 |
| PL2536797T3 (pl) | 2018-01-31 |
| JP2013519764A (ja) | 2013-05-30 |
| BR112012020564A2 (pt) | 2016-07-19 |
| EP2536797A1 (de) | 2012-12-26 |
| DK2536797T3 (en) | 2017-10-16 |
| US8916635B2 (en) | 2014-12-23 |
| ES2635083T3 (es) | 2017-10-02 |
| WO2011101176A1 (de) | 2011-08-25 |
| US20120309895A1 (en) | 2012-12-06 |
| DE102010001987A1 (de) | 2011-08-18 |
| CN102844391A (zh) | 2012-12-26 |
| CN102844391B (zh) | 2015-04-22 |
| AU2011217504A1 (en) | 2012-07-12 |
| EP2536797B1 (de) | 2017-06-21 |
| CA2789841A1 (en) | 2011-08-25 |
| JP5855021B2 (ja) | 2016-02-09 |
| TW201141919A (en) | 2011-12-01 |
| CA2789841C (en) | 2017-07-11 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |