JP6869936B2 - 可逆架橋反応組成物 - Google Patents
可逆架橋反応組成物 Download PDFInfo
- Publication number
- JP6869936B2 JP6869936B2 JP2018207712A JP2018207712A JP6869936B2 JP 6869936 B2 JP6869936 B2 JP 6869936B2 JP 2018207712 A JP2018207712 A JP 2018207712A JP 2018207712 A JP2018207712 A JP 2018207712A JP 6869936 B2 JP6869936 B2 JP 6869936B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- structure represented
- furan
- integer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 68
- 238000006243 chemical reaction Methods 0.000 title claims description 66
- 230000002441 reversible effect Effects 0.000 title claims description 49
- 238000004132 cross linking Methods 0.000 title claims description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 41
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 17
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- -1 indolylene group Chemical group 0.000 claims description 9
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 9
- 125000005556 thienylene group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 7
- 125000005560 phenanthrenylene group Chemical group 0.000 claims description 7
- 125000004653 anthracenylene group Chemical group 0.000 claims description 6
- 125000005567 fluorenylene group Chemical group 0.000 claims description 6
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005462 imide group Chemical group 0.000 claims description 3
- 125000000879 imine group Chemical group 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000003500 enol ether group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002966 varnish Substances 0.000 description 25
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 238000004611 spectroscopical analysis Methods 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 229920001955 polyphenylene ether Polymers 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 238000011925 1,2-addition Methods 0.000 description 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 150000002084 enol ethers Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
- C08F267/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of anhydrides
-
- 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
- C08F277/00—Macromolecular compounds obtained by polymerising monomers on to polymers of carbocyclic or heterocyclic monomers as defined respectively in group C08F32/00 or in group C08F34/00
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/08—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to polyphenylene oxides
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/831—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3318—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group heterocyclic
-
- 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
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
-
- 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
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/44—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols by oxidation of phenols
-
- 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
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- 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
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/126—Polyphenylene oxides modified by chemical 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/02—Low molecular weight, e.g. <100,000 Da.
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/149—Side-chains having heteroaromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/16—End groups
- C08G2261/164—End groups comprising organic end groups
- C08G2261/1646—End groups comprising organic end groups comprising aromatic or heteroaromatic end groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Furan Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
本出願は、参照することにより本明細書に援用される、2017年11月2日に出願された米国特許仮出願第62/580483号の利益を主張する。
Claims (7)
- 少なくとも1つの式(I)で示される構造を有するフラン基含有オリゴマーと、
式(II)で示される構造を有するビスマレイミドと、
を含み、
前記式(I)は、式(I)A、式(I)Bおよび式(I)Cのうち少なくとも1つである可逆架橋反応組成物。
xは1〜5の整数であり、Gは直接結合、−O−、−NH−、−Ar−NH−(CH 2 ) b −、−Ar−O−(CH 2 ) b −、−Ar−O−(CH 2 ) a −NH−(CH 2 ) b −、−(CH 2 ) a −NH−(CH 2 ) b −、−(CH 2 ) a −O−(CH 2 ) b −または−(CH 2 ) a −CH(OH)−(CH 2 ) b −NH−であり、Arは、1〜4個のC 1 〜C 6 アルキル基の置換基を有するフェニレン基、ビフェニレン基、ナフチレン基、チエニレン基、インドリレン基、フェナントレニレン基、インデニレン基、アントラセニレン基、またはフルオレニレン基であり、aは1〜5の整数であり、bは0〜5の整数であり、
(繰り返し単位
繰り返し単位
Eは、置換または未置換のC6−C25アリーレン基、C7−C25アルキルアリール基、C7−C25アリールアルキル基、C6−C25ヘテロアリーレン基、C7−C25アシルアリール基、C7−C25アルコキシアリール基、C7−C25アシルオキシアリール基、またはC6−C25アリーレンエーテル基である。) - 式(III)で示される構造を有するフラン基含有化合物をさらに含む請求項1に記載の可逆架橋反応組成物。
- 前記少なくとも1つの式(I)で示される構造を有するフラン基含有オリゴマーと、前記式(III)で示される構造を有するフラン基含有化合物との重量比が20:80〜80:20である、請求項3に記載の可逆架橋反応組成物。
- 前記式(I)で示される構造を有するフラン基含有オリゴマーおよび前記式(III)で示される構造を有するフラン基含有化合物のフラン基の合計当量数と、式(II)で示される構造を有するビスマレイミドのマレイミド基との当量数比が、0.7:1〜1:0.5である、請求項3に記載の可逆架橋反応組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762580483P | 2017-11-02 | 2017-11-02 | |
US62/580,483 | 2017-11-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019108524A JP2019108524A (ja) | 2019-07-04 |
JP6869936B2 true JP6869936B2 (ja) | 2021-05-12 |
Family
ID=64899157
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018207798A Pending JP2019085409A (ja) | 2017-11-02 | 2018-11-02 | フラン修飾の化合物及びオリゴマー(furan−modified compound and oligomer) |
JP2018207712A Active JP6869936B2 (ja) | 2017-11-02 | 2018-11-02 | 可逆架橋反応組成物 |
JP2020030500A Active JP6978107B2 (ja) | 2017-11-02 | 2020-02-26 | フラン修飾の化合物及びオリゴマー(furan−modified compound and oligomer) |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018207798A Pending JP2019085409A (ja) | 2017-11-02 | 2018-11-02 | フラン修飾の化合物及びオリゴマー(furan−modified compound and oligomer) |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020030500A Active JP6978107B2 (ja) | 2017-11-02 | 2020-02-26 | フラン修飾の化合物及びオリゴマー(furan−modified compound and oligomer) |
Country Status (5)
Country | Link |
---|---|
US (2) | US10858471B2 (ja) |
EP (1) | EP3480254A1 (ja) |
JP (3) | JP2019085409A (ja) |
CN (2) | CN109748998B (ja) |
TW (2) | TWI709602B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI709602B (zh) | 2017-11-02 | 2020-11-11 | 財團法人工業技術研究院 | 可逆交聯反應組成物 |
US11247978B2 (en) | 2017-11-02 | 2022-02-15 | Industrial Technology Research Institute | Reversible crosslinking reactant composition |
CN110317428A (zh) * | 2019-07-16 | 2019-10-11 | 中北大学 | 一种耐热耐腐蚀高力学性能共固化双马来酰亚胺/呋喃树脂 |
CN113388108B (zh) * | 2021-06-30 | 2022-05-31 | 宁波长阳科技股份有限公司 | 具有自修复功能的聚酰亚胺树脂、聚酰亚胺薄膜及制备方法和柔性可折叠显示屏盖板基膜 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3435003A (en) | 1966-06-01 | 1969-03-25 | Du Pont | Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides |
EP0357110A1 (en) | 1988-08-05 | 1990-03-07 | Akzo N.V. | Two component coating curable at ambient temperature via a Diels-Alder reaction |
US5844020A (en) * | 1997-03-31 | 1998-12-01 | Xerox Corporation | Phase change ink compositions |
WO2003038109A2 (en) * | 2001-09-18 | 2003-05-08 | The Board Of Regents Of The University Of Nebraska | Method for the inhibition of methanogenesis |
US6933361B2 (en) * | 2002-07-12 | 2005-08-23 | The Regents Of The University Of California | Thermally re-mendable cross-linked polymers |
JP2006335861A (ja) | 2005-06-01 | 2006-12-14 | Nippon Zeon Co Ltd | 接着剤、接着剤フィルム、半導体部品パッケージ、および半導体部品パッケージの製造方法 |
GB2453112B (en) * | 2007-09-25 | 2010-12-22 | Schlumberger Holdings | Reversible polymeric gelation for oilfield applications |
RU2555883C2 (ru) | 2009-06-11 | 2015-07-10 | ХЕНКЕЛЬ Юэс АйПи ЭлЭлСи | Термически обратимая термоплавкая клеевая композиция, содержащая многофункциональные диеновые и диенофильные соединения |
US9884944B2 (en) | 2010-05-19 | 2018-02-06 | Drexel University | Remendable interfaces for polymer composites |
WO2012074994A1 (en) | 2010-11-29 | 2012-06-07 | The Regents Of The University Of Colorado, A Body Corporate | Novel thermoreversible network scaffolds and methods of preparing same |
CA2819759C (en) | 2010-11-30 | 2019-09-10 | Connora Technologies, Inc. | Novel agents for reworkable epoxy resins |
US8511369B2 (en) | 2011-04-18 | 2013-08-20 | International Business Machines Corporation | Thermally reversible crosslinked polymer modified particles and methods for making the same |
DE102011087226A1 (de) * | 2011-11-28 | 2013-05-29 | Evonik Degussa Gmbh | Pseudo-thermoplastische, selbstvernetzende Composites |
WO2014025986A2 (en) | 2012-08-10 | 2014-02-13 | The University Of Akron | Novel polyisobutylene-based thermoplastic elastomers |
US9085719B2 (en) | 2013-03-18 | 2015-07-21 | International Business Machines Corporation | Thermally reversible thermal interface materials with improved moisture resistance |
CN103408684B (zh) * | 2013-07-12 | 2015-12-02 | 中山大学 | 一种热可逆交联聚合物薄膜及其制备方法 |
CN104045810B (zh) | 2014-06-18 | 2016-08-31 | 中国科学院化学研究所 | 一种二胺加成物交联剂、其制备方法及其制备热可逆交联环氧树脂及其复合材料 |
KR20170040297A (ko) | 2014-07-31 | 2017-04-12 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 열가역성 가교 폴리우레탄 |
TWI709602B (zh) | 2017-11-02 | 2020-11-11 | 財團法人工業技術研究院 | 可逆交聯反應組成物 |
-
2018
- 2018-11-02 TW TW107138967A patent/TWI709602B/zh active
- 2018-11-02 US US16/179,170 patent/US10858471B2/en active Active
- 2018-11-02 TW TW107138936A patent/TWI701244B/zh active
- 2018-11-02 JP JP2018207798A patent/JP2019085409A/ja active Pending
- 2018-11-02 CN CN201811299735.3A patent/CN109748998B/zh active Active
- 2018-11-02 US US16/179,296 patent/US10894853B2/en active Active
- 2018-11-02 EP EP18204154.1A patent/EP3480254A1/en active Pending
- 2018-11-02 JP JP2018207712A patent/JP6869936B2/ja active Active
- 2018-11-02 CN CN201811301767.2A patent/CN109749328B/zh active Active
-
2020
- 2020-02-26 JP JP2020030500A patent/JP6978107B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
CN109749328A (zh) | 2019-05-14 |
TWI709602B (zh) | 2020-11-11 |
EP3480254A1 (en) | 2019-05-08 |
CN109749328B (zh) | 2021-04-06 |
US10858471B2 (en) | 2020-12-08 |
JP2020079310A (ja) | 2020-05-28 |
JP2019108524A (ja) | 2019-07-04 |
US10894853B2 (en) | 2021-01-19 |
TW201918481A (zh) | 2019-05-16 |
JP2019085409A (ja) | 2019-06-06 |
US20190153139A1 (en) | 2019-05-23 |
JP6978107B2 (ja) | 2021-12-08 |
CN109748998A (zh) | 2019-05-14 |
US20190144410A1 (en) | 2019-05-16 |
CN109748998B (zh) | 2021-08-31 |
TW201918517A (zh) | 2019-05-16 |
TWI701244B (zh) | 2020-08-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6869936B2 (ja) | 可逆架橋反応組成物 | |
JP7361029B2 (ja) | 硬化性化合物 | |
KR101505199B1 (ko) | 열경화성 올리고머 또는 폴리머, 이를 포함한 열경화성 수지 조성물, 및 이를 이용한 인쇄회로기판 | |
JPS6121491B2 (ja) | ||
CA2835199A1 (en) | Halogen free thermoset resin system for low dielectric loss at high frequency applications | |
US11247978B2 (en) | Reversible crosslinking reactant composition | |
JP3435496B2 (ja) | 硬化性難燃樹脂組成物、これより製造したプリプレグ及び難燃電気用積層板 | |
JPS6118937B2 (ja) | ||
KR20160146113A (ko) | 마이크로파를 이용한 폴리이미드 필름 제조방법 | |
KR102652027B1 (ko) | 폴리 페닐렌 에테르계 수지 조성물 | |
KR101692137B1 (ko) | 수용성 폴리아믹산을 사용한 폴리이미드 분말 및 폴리이미드 성형품 제조방법 | |
CA1280540C (en) | Thermoset polymers of styrene terminated tetrakis phenols | |
KR102271573B1 (ko) | 마이크로파를 이용한 폴리이미드 필름 제조방법 | |
WO2024128145A1 (ja) | 置換型ポリフェニレンサルファイド樹脂 | |
JPH1112463A (ja) | 印刷配線板用樹脂組成物、ワニス、プリプレグ及びそれを用いた印刷配線板用積層板 | |
JP2024086554A (ja) | 置換型ポリフェニレンサルファイド樹脂 | |
CN117986578A (zh) | 经改质的双马来酰亚胺树脂 | |
JPH05320316A (ja) | 低誘電率熱硬化性樹脂組成物 | |
JPH05320314A (ja) | 低誘電率熱硬化性樹脂組成物 | |
KR20150037218A (ko) | 폴리벤족사진 및 그 제조방법 | |
JPH0345649A (ja) | 硬化性官能化ポリフェニレンエーテル樹脂組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20181102 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20191010 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20191023 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200123 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200407 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200707 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20201021 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210121 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210323 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210414 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6869936 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |