CN116710436A - 电荷转移络合物 - Google Patents
电荷转移络合物 Download PDFInfo
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- CN116710436A CN116710436A CN202280009944.8A CN202280009944A CN116710436A CN 116710436 A CN116710436 A CN 116710436A CN 202280009944 A CN202280009944 A CN 202280009944A CN 116710436 A CN116710436 A CN 116710436A
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- compound
- electron
- charge transfer
- transfer complex
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QPGRDTXELAFGRG-UHFFFAOYSA-N n',n'-di(propan-2-yl)propane-1,3-diamine Chemical compound CC(C)N(C(C)C)CCCN QPGRDTXELAFGRG-UHFFFAOYSA-N 0.000 description 1
- KXBUDXGDASOGBX-UHFFFAOYSA-N n',n'-dibenzylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1CN(CCCN)CC1=CC=CC=C1 KXBUDXGDASOGBX-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- YFQPICDSUBYACX-UHFFFAOYSA-N n'-(2-phenylethyl)propane-1,3-diamine Chemical compound NCCCNCCC1=CC=CC=C1 YFQPICDSUBYACX-UHFFFAOYSA-N 0.000 description 1
- HUWUUMUEMQWJKZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-benzylpropane-1,3-diamine Chemical compound NCCCN(CCCN)CC1=CC=CC=C1 HUWUUMUEMQWJKZ-UHFFFAOYSA-N 0.000 description 1
- LUZCQJHUWNIZNZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-pentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCN LUZCQJHUWNIZNZ-UHFFFAOYSA-N 0.000 description 1
- IZDWJSKWDHFHSF-UHFFFAOYSA-N n'-(cyclohexylmethyl)propane-1,3-diamine Chemical compound NCCCNCC1CCCCC1 IZDWJSKWDHFHSF-UHFFFAOYSA-N 0.000 description 1
- HUQLOABSMDKQBW-UHFFFAOYSA-N n'-benzyl-n-methylethane-1,2-diamine Chemical compound CNCCNCC1=CC=CC=C1 HUQLOABSMDKQBW-UHFFFAOYSA-N 0.000 description 1
- IWUHWRSKHTWKHZ-UHFFFAOYSA-N n'-cyclohexyl-n-methylethane-1,2-diamine Chemical compound CNCCNC1CCCCC1 IWUHWRSKHTWKHZ-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- WLNSKTSWPYTNLY-UHFFFAOYSA-N n-ethyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCNCCN(C)C WLNSKTSWPYTNLY-UHFFFAOYSA-N 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- HATIEXJZXOLRAO-UHFFFAOYSA-N octanedihydrazide Chemical compound NNC(=O)CCCCCCC(=O)NN HATIEXJZXOLRAO-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C07C25/10—Trichloro-benzenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/544—Diformyl benzenes; Alkylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
- C07C49/786—Benzophenone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/16—Quinones the quinoid structure being part of a condensed ring system containing three rings
- C07C50/18—Anthraquinones, i.e. C14H8O2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/121—Charge-transfer complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Epoxy Resins (AREA)
Abstract
本发明的目的在于提供在作为环氧树脂固化剂使用的情况下可得到固化性与贮藏稳定性的平衡优异的固化性树脂组合物的电荷转移络合物。本发明为具有咪唑部位作为电子给予部位的电荷转移络合物。上述电荷转移络合物可以为具有电子接受部位的化合物(b)接受了具有咪唑部位的化合物(a)中所含的电子而得到的物质,也可以为在分子中具有咪唑部位及电子接受部位的化合物中电子接受部位接受了咪唑部位中所含的电子而得到的物质。
Description
技术领域
本发明涉及电荷转移络合物,详细而言,涉及具有咪唑部位的电荷转移络合物、由该电荷转移络合物形成的环氧树脂固化剂、及含有该电荷转移络合物的固化性树脂组合物。
背景技术
环氧树脂作为涂料、粘接剂、各种成形材料等的成分而在工业上被广泛使用。
在将环氧树脂用于上述用途的情况下,通常与固化剂组合使用,作为该固化剂,已知有酸酐系固化剂、胺系固化剂、酚系固化剂等各种固化剂。
上述固化剂根据用途而分开使用,例如咪唑系固化剂与加聚型固化剂不同,由于为阴离子聚合型固化剂,因此通过少量的添加而能够固化,此外在低挥发性且毒性低的方面也是有用的,因此可以适宜用于电气/电子部件。
然而,在将环氧树脂固化剂单独使用的情况下,难以取得固化性与贮藏稳定性的平衡。为了提高贮藏稳定性,例如在专利文献1中提出了将咪唑化合物与环氧树脂的反应物用于环氧固化系统,在专利文献2中提出了包含改性咪唑、改性胺及酚类化合物的环氧树脂用固化剂组合物。
然而,在进行了这些各种改性的情况下,改性物的粘度上升,操作、作业性受损等,未得到能够令人满意的改性物。
现有技术文献
专利文献
专利文献1:美国专利4066625号
专利文献2:日本特开2007-297493号公报
非专利文献
非专利文献1:JORNAL OF POLYMER SCIENCE,PART A POLYMER CHEMISTRY 2016,54,2680-2688
非专利文献2:JORNAL OF POLYMER SCIENCE,PART A POLYMER CHEMISTRY 2018,56,471-474
非专利文献3:Composits Part B17(2019)107380
非专利文献4:Materials Leters234(2019)379-383
发明内容
因此,本发明所要解决的课题是提供在作为环氧树脂固化剂使用的情况下可得到固化性与贮藏稳定性的平衡优异的固化性树脂组合物的电荷转移络合物。
本发明人们进行了深入研究,结果发现:具有咪唑部位作为电子给予体的电荷转移络合物作为环氧树脂固化剂是有效的;进而将其与环氧树脂组合而得到的树脂组合物为固化性与贮藏稳定性的平衡优异的固化性树脂组合物,从而达成了本发明。
即,本发明为一种电荷转移络合物,其具有咪唑部位作为电子给予部位。
此外,本发明为一种环氧树脂用固化剂,其由上述电荷转移络合物形成。
此外,本发明为一种固化性树脂组合物,其含有环氧树脂及上述电荷转移络合物。
本发明的电荷转移络合物通过与环氧树脂组合,能够提供固化性与贮藏稳定性优异的固化性树脂组合物,因此作为环氧树脂固化剂是有用的。通过使用本发明的电荷转移络合物,能够提供适于单组分固化型的涂料、粘接剂等用途的树脂组合物。
附图说明
图1是本发明的电荷转移络合物的UV光谱测定结果。
具体实施方式
以下,对本发明的电荷转移络合物进行说明。
电荷转移络合物也被称为电子接受-给予络合物(Electron-donor-acceptorcomplex),是由电荷可在分子间移动的2个以上的不同分子、或在分子内具有电子接受部位和电子给予部位而电子能够移动的1个分子构成的缔合体。
本发明的电荷转移络合物的特征在于,电子给予部位为咪唑部位。
作为上述电荷转移络合物,例如可列举出通过具有电子接受部位的化合物(b)接受了具有咪唑部位的化合物(a)中所含的电子而得到的电荷转移络合物。此外,上述电荷转移络合物也可以为在分子中具有咪唑部位及电子接受部位的化合物中电子接受体部位接受了咪唑部位中所含的电子而得到的物质。
作为上述电荷转移络合物的(a)成分即具有咪唑部位的化合物,例如可列举出2-甲基咪唑、1,2-二甲基咪唑、2-乙基-4-甲基咪唑、2-异丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑等具有烷基的咪唑类;1-苄基-2-咪唑、1-苄基-2-乙基-4-甲基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、1-苯基甲基-2-苯基咪唑等具有芳香族基的咪唑类;2-氨基丙基咪唑等具有氨基烷基的咪唑类;1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-苯基咪唑等具有氰基的咪唑类;2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟基甲基咪唑等具有羟基甲基的咪唑类;1-丁氧基羰基乙基-2-甲基咪唑、1-丁氧基羰基乙基-2-乙基-4-甲基咪唑、1-丁氧基羰基乙基-2-苯基咪唑、1-(2-乙基己基)羰基乙基-2-甲基咪唑、1-(2-乙基己基)羰基乙基-2-乙基-4-甲基咪唑、1-(2-乙基己基)羰基乙基-2-苯基咪唑、1-辛氧基羰基乙基-2-甲基咪唑、1-辛氧基羰基乙基-2-乙基-4-甲基咪唑、1-辛氧基羰基乙基-2-苯基咪唑、己二醇·双(2-甲基咪唑基乙酸)酯、己二醇·双(2-乙基-4-甲基咪唑基乙酸)酯、己二醇·双(2-苯基咪唑基乙酸)酯、癸二醇·双(2-甲基咪唑基乙酸)酯、癸二醇·双(2-乙基-4-甲基咪唑基乙酸)酯、癸二醇·双(2-苯基咪唑基乙酸)酯、三环戊烷二甲醇·双(2-甲基咪唑基乙酸)酯、三环戊烷二甲醇·双(2-乙基-4-甲基咪唑基乙酸)酯、三环戊烷二甲醇·双(2-苯基咪唑基乙酸)酯、1-(2-羟基萘基甲基)-2-甲基咪唑、1-(2-羟基萘基甲基)-2-乙基-4-甲基咪唑、1-(2-羟基萘基甲基)-2-苯基咪唑等具有酯键的咪唑类;2,3-二氢-1H-吡咯并(1,2a)苯并咪唑、1-十二烷基-2-甲基-3-苄基咪唑鎓氯化物、咪唑硅烷、2,4-二氨基-6-〔2’-甲基咪唑基-(1’)〕-乙基-s-三嗪等特殊咪唑类。进而,上述例示的咪唑化合物也可以为利用环氧化合物、聚羧酸及异氰脲酸等的改性物。
作为上述环氧化合物,例如可列举出氢醌、间苯二酚、焦儿茶酚及间苯三酚等单核多元酚化合物的聚缩水甘油醚化物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、线型酚醛清漆、邻甲酚酚醛清漆、乙基线型酚醛清漆、丁基线型酚醛清漆、辛基线型酚醛清漆、间苯二酚酚醛清漆及萜烯酚等多核多元酚化合物的聚缩水甘油醚化物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫代甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基)丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇及双酚A-环氧烷烃加成物等多元醇化合物的聚缩水甘油醚化物;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸及桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯化物及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺及N,N,N’,N’-四(2,3-环氧丙基)-4,4-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯及双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯及环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物;异氰脲酸三缩水甘油酯等杂环化合物。
作为上述多聚羧酸,例如可列举出马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸及桥亚甲基四氢邻苯二甲酸等。
上述咪唑化合物中,2-甲基咪唑、2-乙基-4-甲基咪唑等未改性化合物能够通过添加比较少量而固化,并且通过与其他固化剂组合还能够发挥作为固化促进剂的效果,因此更优选。
上述电荷转移络合物的(b)成分即具有电子接受部位的化合物只要是在上述(a)成分即具有咪唑部位的化合物的存在下能够接受(a)成分即具有咪唑部位的化合物中所含的电子的化合物,则可以没有特别限制地使用。例如可列举出酰亚胺化合物、芳香族化合物等。
具有电子接受部位的化合物中酰亚胺化合物由于合成原料多样,分子设计的自由度高,并且相容性优异,因此容易选择不易对所得到的固化性树脂组合物的物性造成不良影响的化合物,因此优选。尤其是分子中具有芳香族骨架的酰亚胺化合物由于可得到贮藏稳定性与固化性的平衡优异的固化性树脂组合物,因此优选。
此外,(b)成分即具有电子接受部位的化合物的最低未占轨道(LUMO,lowestunoccupied molecular orbital,也可称为最低未占分子轨道)为-1eV以下的化合物由于将其与环氧树脂一起配合而制成固化性树脂组合物的情况下,可得到贮藏稳定性及固化性优异的组合物,因此优选。最低未占轨道(LUMO)例如通过电子结构计算而得到。
以下示出(b)成分即具有电子接受部位的化合物的具体例子。
[化学式1]
[化学式2]
[化学式3]
[化学式4]
[化学式5]
[化学式6]
[化学式7]
[化学式8]
[化学式9]
[化学式10]
[化学式11]
[化学式12]
[化学式13]
[化学式14]
[化学式15]
[化学式16]
[化学式17]
[化学式18]
[化学式19]
[化学式20]
[化学式21]
(b)成分即具有电子接受部位的化合物的使用量相对于(a)成分即具有咪唑部位的化合物1摩尔为0.01~20摩尔,优选为0.1~10摩尔,进一步优选为0.2~8摩尔。具有电子接受部位的化合物的使用量低于0.01摩尔时,在将由它们得到的电荷转移络合物作为环氧树脂固化剂使用的情况下,有可能无法得到固化性树脂组合物的稳定性赋予效果,在超过20摩尔的情况下有可能对固化性树脂组合物的固化性造成不良影响。
制造上述电荷转移络合物的方法没有特别限定,可以通过将上述(a)成分及(b)成分混合来制造。两成分为液状的情况可通过在常温下混合而得到电荷转移络合物,但在至少一者为固体的情况下也可以进行加热、熔融而混合、或使用溶剂制成溶液而混合。
本发明的电荷转移络合物为在分子中具有咪唑部位及电子接受部位的化合物中电子接受部位接受了咪唑部位中所含的电子而得到的物质的情况下,上述电子接受部位只要是能够接受由咪唑部位得到的电子的部位即可,例如可列举出酰亚胺部位、芳香族部位等。尤其是酰亚胺部位由于可得到合成原料多样、分子设计的自由度高、并且相容性优异、不易对所得到的固化性树脂组合物的物性造成不良影响的化合物,因此优选。
作为在分子中具有咪唑部位及电子接受部位的化合物,例如可列举出下述的通式(1)所表示的化合物。
[化学式22]
通式(1)中,R1、R2及R3分别独立地表示氢原子或可具有取代基的碳原子数为1~20的烃基,R4表示可具有取代基的碳原子数1~10的二价的烃基,环A表示可具有取代基的苯环、可具有取代基的环己烷环、或可具有取代基的降冰片烯环。
上述式(1)中,作为构成R6、R7及R8所表示的可具有取代基的碳原子数1~20的烃基的烃基,例如可列举出甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、仲戊基、叔戊基、己基、庚基、辛基、异辛基、叔辛基、2-乙基己基、壬基、异壬基、癸基、异癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等烷基;苯基、萘基及蒽基等芳基;环己基等脂环式基等。
此外,作为构成R9所表示的可具有取代基的碳原子数1~10的二价的烃基的烃基,例如可列举出亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基及亚癸基等。
此外,作为R6~R9中的取代基,可列举出烷基、烷氧基、卤代烷基、卤代烷氧基、卤素原子、硝基、腈基、氨基及缩水甘油醚基等。
作为上述通式(1)所表示的化合物中的咪唑骨架,例如可列举出2-甲基咪唑-1-基、2-乙基-4-甲基咪唑-1-基、2-异丙基咪唑-1-基、2-十一烷基咪唑-1-基、2-十七烷基咪唑-1-基、2-苯基咪唑-1-基及2-苯基-4-甲基咪唑-1-基等具有烷基的咪唑骨架;2-苄基咪唑-1-基、2-苄基-4-甲基咪唑-1-基及2-苯基甲基-4-苯基咪唑-1-基等具有芳香族基的咪唑骨架;2-氨基丙基咪唑-1-基等具有氨基烷基的咪唑骨架;2-氰基乙基-4-甲基咪唑-1-基、2-氰基乙基-4-十一烷基咪唑-1-基、2-氰基乙基-甲基咪唑-1-基及2-氰基乙基-4-苯基咪唑-1-基等具有氰基的咪唑骨架;2-苯基-4,5-二羟基甲基咪唑-1-基及2-苯基-4-甲基-5-羟基甲基咪唑-1-基等具有羟基甲基的咪唑骨架;2-丁氧基羰基乙基-4-甲基咪唑-1-基、2-丁氧基羰基乙基-4-甲基咪唑-1-基、2-丁氧基羰基乙基-4-苯基咪唑-1-基、2-(2-乙基己基)羰基乙基-4-甲基咪唑-1-基、2-(2-乙基己基)羰基乙基-4-甲基咪唑-1-基、2-(2-乙基己基)羰基乙基-4-苯基咪唑-1-基、2-辛氧基羰基乙基-4-甲基咪唑-1-基、2-辛氧基羰基乙基-4-甲基咪唑-1-基及2-辛氧基羰基乙基-4-苯基咪唑-1-基等具有酯键的咪唑骨架等。
此外,上述通式(1)所表示的化合物的最低未占轨道(LUMO)为-1eV以下的化合物在将其和环氧树脂配合而制成固化性树脂组合物的情况下,可得到贮藏稳定性及固化性优异的组合物,因此优选。最低未占轨道(LUMO)例如通过电子结构计算而得到。
以下示出在分子中具有咪唑部位及电子接受部位的化合物的具体例子。
[化学式23]
[化学式24]
电荷转移络合物是给予电子的电子给予部位与接受电子的电子接受部位形成络合物的物质。电荷转移络合物在激发状态下引起电荷转移跃迁。由该现象,电子给予部位及电子接受部位形成电荷转移络合物可以通过络合物形成后的UV-vis吸收光谱在比络合物形成前的各原料的UV-vis光谱中的吸收带更长的波长侧具有新的吸收带来确认。
本发明的环氧树脂固化剂由上述电荷转移络合物形成。本发明的电荷转移络合物在环氧树脂的存在下稳定,作为环氧树脂的固化剂是良好的。
接着,对本发明的固化性树脂组合物进行说明。
本发明的固化性树脂组合物含有环氧树脂及上述电荷转移络合物。
本发明中使用的环氧树脂只要是在分子中具有至少2个环氧基即可,可以对分子结构、分子量等没有特别限制地使用。
作为上述环氧树脂,可列举出氢醌、间苯二酚、焦儿茶酚及间苯三酚等单核多元酚化合物的聚缩水甘油醚化物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、线型酚醛清漆、邻甲酚酚醛清漆、乙基线型酚醛清漆、丁基线型酚醛清漆、辛基线型酚醛清漆、间苯二酚酚醛清漆及萜烯酚等多核多元酚化合物的聚缩水甘油醚化物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫代甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基)丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇及双酚A-环氧烷烃加成物等多元醇化合物的聚缩水甘油醚化物;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸及桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯化物及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺及N,N,N’,N’-四(2,3-环氧丙基)-4,4-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯及双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯及环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物;异氰脲酸三缩水甘油酯等杂环化合物。此外,这些环氧树脂也可以以通过末端异氰酸酯的预聚物而内部交联的形式、此外通过多价的活泼氢化合物(多元酚、多胺、含羰基的化合物、多聚磷酸酯等)而高分子量化的形式来使用。环氧树脂可以单独使用,也可以将2种以上并用。
本发明的固化性树脂组合物含有环氧树脂及上述电荷转移络合物。在使用由(a)成分即具有咪唑部位的化合物和(b)成分即具有电子接受部位的化合物得到的电荷转移络合物的情况下,也可以通过将环氧树脂与电荷转移络合物混合来制造,但也可以通过在环氧树脂中分别分开配合(a)成分即具有咪唑部位的化合物和(b)成分即具有电子接受部位的化合物,在固化性树脂组合物中形成电荷转移络合物,来制造目标固化性树脂组合物。
在本发明的固化性树脂组合物中,上述电荷转移络合物的使用量没有特别限制,但相对于环氧树脂100质量份,优选为0.01~500质量份,更优选为0.1~100质量份。在少于0.01质量份的情况下,有可能得不到相对于固化性及稳定性的改善效果,在超过500质量份而使用的情况下有可能对固化物的物性造成不良影响。
此外,在本发明的固化性树脂组合物中,除了上述电荷转移络合物以外,可以使用通常的环氧树脂固化剂。作为该环氧树脂固化剂,例如可列举出酸酐系固化剂、酚系固化剂、胺系固化剂及多硫醇系固化剂等。
作为上述酸酐系固化剂,例如可列举出降冰片烯二酸酐、邻苯二甲酸酐、马来酸酐、甲基降冰片烯二酸酐、琥珀酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、二苯甲酮四羧酸酐、偏苯三酸酐、均苯四甲酸酐及氢化甲基纳迪克酸酐等。
作为上述酚系固化剂,例如可列举出线型酚醛清漆树脂、甲酚线型酚醛树脂、芳香族烃甲醛树脂改性酚醛树脂、二环戊二烯苯酚加成型树脂、苯酚芳烷基树脂(Xylokresin)、萘酚芳烷基树脂、三苯酚基甲烷树脂、四苯酚基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩合酚醛清漆树脂、萘酚-甲酚共缩合酚醛清漆树脂、联苯改性酚醛树脂(通过双亚甲基而连接有酚核的多元酚化合物)、联苯改性萘酚树脂(通过双亚甲基而连接有酚核的多元萘酚化合物)、氨基三嗪改性酚醛树脂(在分子结构中具有苯酚骨架、三嗪环及伯氨基的化合物、)及含烷氧基的芳香环改性酚醛清漆树脂(通过甲醛而连接有酚核及含烷氧基的芳香环的多元酚化合物)等多元酚化合物等。
作为上述胺系固化剂,例如可列举出乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,3-二氨基丁烷、1,4-二氨基丁烷、六亚甲基二胺及间苯二胺等亚烷基二胺类;二亚乙基三胺、三亚乙基三胺及四亚乙基五胺等多烷基多胺类;1,4-二氨基环己烷、1,3-二氨基环己烷、1,3-二氨基甲基环己烷、1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、4,4’-二氨基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-二氨基二环己基丙烷、双(4-氨基环己基)砜、4,4’-二氨基二环己基醚、2,2’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺及降冰片烯二胺等脂环式多胺类;二氨基二苯基甲烷、二氨基二苯基砜、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二氨基苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯、3,3’-二乙基-4,4’-二氨基二苯基甲烷及3,5,3’,5’-四甲基-4,4’-二氨基二苯基甲烷等芳香族多胺类;N,N-二甲基氨基乙基胺、N,N-二乙基氨基乙基胺、N,N-二异丙基氨基乙基胺、N,N-二烯丙基氨基乙基胺、N,N-苄基甲基氨基乙基胺、N,N-二苄基氨基乙基胺、N,N-环己基甲基氨基乙基胺、N,N-二环己基氨基乙基胺、N-(2-氨基乙基)吡咯烷、N-(2-氨基乙基)哌啶、N-(2-氨基乙基)吗啉、N-(2-氨基乙基)哌嗪、N-(2-氨基乙基)-N’-甲基哌嗪、N,N-二甲基氨基丙基胺、N,N-二乙基氨基丙基胺、N,N-二异丙基氨基丙基胺、N,N-二烯丙基氨基丙基胺、N,N-苄基甲基氨基丙基胺、N,N-二苄基氨基丙基胺、N,N-环己基甲基氨基丙基胺、N,N-二环己基氨基丙基胺、N-(3-氨基丙基)吡咯烷、N-(3-氨基丙基)哌啶、N-(3-氨基丙基)吗啉、N-(3-氨基丙基)哌嗪、N-(3-氨基丙基)-N’-甲基哌啶、4-(N,N-二甲基氨基)苄基胺、4-(N,N-二乙基氨基)苄基胺、4-(N,N-二异丙基氨基)苄基胺、N,N,-二甲基异佛尔酮二胺、N,N-二甲基双氨基环己烷、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基乙二胺、N,N,N’-三乙基乙二胺、N’-乙基-N,N-二甲基丙烷二胺、N’-乙基-N,N-二苄基氨基丙基胺;N,N-(双氨基丙基)-N-甲基胺、N,N-双氨基丙基乙基胺、N,N-双氨基丙基丙基胺、N,N-双氨基丙基丁基胺、N,N-双氨基丙基戊基胺、N,N-双氨基丙基己基胺、N,N-双氨基丙基-2-乙基己基胺、N,N-双氨基丙基环己基胺、N,N-双氨基丙基苄基胺、N,N-双氨基丙基烯丙基胺、双〔3-(N,N-二甲基氨基丙基)〕胺、双〔3-(N,N-二乙基氨基丙基)〕胺、双〔3-(N,N-二异丙基氨基丙基)〕胺、双〔3-(N,N-二丁基氨基丙基)〕胺;草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼及邻苯二甲酸二酰肼等二元酸二酰肼;双氰胺、苯并胍胺及乙酰胍胺等胍化合物;三聚氰胺等。
此外,也可以使用将上述胺类改性而得到的改性胺系固化剂。作为改性方法,可列举出与羧酸的脱水缩合、与环氧树脂的加成反应、与异氰酸酯的加成反应、麦克尔加成反应、曼尼希反应、与尿素的缩合反应、及与酮的缩合反应等。
作为上述胺类的改性中可使用的羧酸,例如可列举出马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸及桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸等。
作为上述胺类的改性中可使用的环氧化合物,例如可列举出作为上述电荷转移络合物的(a)成分即具有咪唑部位的化合物的改性中可使用的环氧化合物所例示的环氧化合物。
作为上述胺类的改性中可使用的异氰酸酯化合物,例如可列举出2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、二苯基甲烷-4,4’-二异氰酸酯、苯二异氰酸酯、苯二甲基二异氰酸酯、四甲基苯二甲基二异氰酸酯、1,5-萘二异氰酸酯、1,5-四氢萘二异氰酸酯、3,3’-二甲基二苯基-4,4’-二异氰酸酯、二茴香胺二异氰酸酯及四甲基苯二甲基二异氰酸酯等芳香族二异氰酸酯;异佛尔酮二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯、反式-1,4-环己基二异氰酸酯及降冰片烯二异氰酸酯等脂环式二异氰酸酯;四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4和/或2,4,4-三甲基六亚甲基二异氰酸酯及赖氨酸二异氰酸酯等脂肪族二异氰酸酯;上述例示的二异氰酸酯的异氰脲酸酯三聚物、缩二脲三聚物及三羟甲基丙烷加合物等;三苯基甲烷三异氰酸酯、1-甲基苯-2,4,6-三异氰酸酯及二甲基三苯基甲烷四异氰酸酯等。进而这些异氰酸酯化合物也可以以碳二亚胺改性、异氰脲酸酯改性、缩二脲改性等改性物的形式使用,也可以以通过各种封端剂而封端的封端异氰酸酯的形式使用。
作为上述多硫醇系固化剂,例如可列举出季戊四醇四(3-巯基丙酸酯)、季戊四醇四(巯基乙酸酯)、二季戊四醇六(3-巯基丙酸酯)、二季戊四醇六(3-巯基丁酸酯)、1,3,4,6-四(2-巯基乙基)-1,3,4,6-四氮杂八氢戊烯-2,5-二酮、1,3,5-三(3-巯基丙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、4,8-、4,7-或5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷及1,3,4,6-四(2-巯基乙基)甘脲等。
作为上述咪唑系固化剂,例如可列举出2-甲基咪唑、2-乙基-4-甲基咪唑、2-异丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、2-氨基丙基咪唑、咪唑硅烷(例如四国化成工业(株)制;2MUSIZ)等。
此外,也可以为将这些咪唑化合物与上述胺系固化剂同样地改性而得到的物质或上述咪唑类与偏苯三酸、异氰脲酸、硼等的盐即咪唑盐类。
作为上述固化剂的市售品,例如可列举出Adeka Hardener EH-3636AS、AdekaHardener EH-4351S(株式会社艾迪科制;双氰胺型潜伏性固化剂)、Adeka Hardener EH-5011S、Adeka Hardener EH-5046S(株式会社艾迪科制;咪唑型潜伏性固化剂)、AdekaHardener EH-4357S、Adeka Hardener EH-5057P、Adeka Hardener EH-5057PK(株式会社艾迪科制;多胺型潜伏性固化剂)、Amicure PN-23、Amicure PN-40(Ajinomoto Fine-Techno制;胺加合系潜伏性固化剂)、Amicure VDH(Ajinomoto Fine-Technoo制;酰肼系潜伏性固化剂)、Fujicure FXR-1020(T&K TOKA制;潜伏性固化剂)、Curezol(四国化成工业制;咪唑系固化剂)、TS-G(四国化成工业制;多硫醇系固化剂)、DPMP、PEMP(SC有机化学制;多硫醇系固化剂)及PETG(淀化学制;多硫醇系固化剂)等。
固化剂可以单独使用,也可以将2种以上并用。
上述固化剂的配合量没有特别限定,但相对于环氧树脂100质量份,优选为0~500质量份,更优选为0~100质量份。
本发明中,可以根据需要将上述固化剂与公知的环氧树脂固化促进剂并用。作为固化促进剂,例如可列举出三苯基膦等膦类;四苯基溴化鏻等鏻盐;苄基二甲基胺及2,4,6-三(二甲基氨基甲基)苯酚等胺类;三甲基氯化铵等季铵盐类;3-(对氯苯基)-1,1-二甲基脲、3-(3,4-二氯苯基)-1,1-二甲基脲、3-苯基-1,1-二甲基脲、异佛尔酮二异氰酸酯-二甲基脲及甲苯二异氰酸酯-二甲基脲等脲类三氟化硼与胺类的络合物、及三氟化硼与醚化合物的络合物等。这些固化促进剂可以单独使用,也可以将2种以上并用。环氧树脂固化促进剂的含量可以没有特别限制地根据固化性树脂组合物的用途而适当设定。
在本发明的固化性树脂组合物中,可以含有硅烷偶联剂。作为硅烷偶联剂,例如可列举出γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷及γ-巯基丙基三甲氧基硅烷等。
在本发明的固化性树脂组合物中,可以含有填充剂。作为填充剂,例如可列举出熔融二氧化硅及结晶二氧化硅等二氧化硅;氢氧化镁、氢氧化铝、钼酸锌、碳酸钙、碳酸硅、硅酸钙、钛酸钾、氧化铍、二氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石及二氧化钛等粉体、或将它们球形化而得到的珠;玻璃纤维、纸浆纤维、合成纤维及陶瓷纤维等纤维等。
本发明的固化性树脂组合物可以溶解于各种溶剂、优选有机溶剂中来使用。作为适当的有机溶剂,例如可列举出四氢呋喃、1,2-二甲氧基乙烷及1,2-二乙氧基乙烷等醚类;异-或正-丁醇、异-或正-丙醇、戊基醇、苄基醇、糠醇及四氢糠醇等醇类;甲乙酮、甲基异丙基酮及甲基丁基酮等酮类;苯、甲苯及二甲苯等芳香族烃;三乙基胺、吡啶、二噁烷及乙腈等。
本发明的固化性树脂组合物也可以进一步根据需要含有其他的各种添加剂。作为上述添加剂,例如可列举出磷系抗氧化剂、酚系抗氧化剂及硫系抗氧化剂;紫外线吸收剂及受阻胺系光稳定剂;联苯酚等酚类化合物(;单烷基缩水甘油醚等反应性稀释剂;邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇及煤焦油等非反应性的稀释剂(增塑剂);玻璃布、芳纶布及碳纤维等增强材料;颜料;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯及芳香族醚等润滑剂;增稠剂;触变剂;消泡剂;防锈剂;胶体二氧化硅及胶体氧化铝等常用的添加剂。本发明中,也可以进一步并用氰酸酯树脂、二甲苯树脂及石油树脂等粘合性的树脂类。
本发明的树脂组合物其用途没有特别限制,但由于能够调整固化性与贮藏稳定性的平衡,因此能够制成单组分固化型的树脂组合物,可以用于相对于混凝土、水泥砂浆、各种金属、皮革、玻璃、橡胶、塑料、木、布、纸等的涂料及粘接剂。
实施例
接着,对本发明通过实施例及比较例进一步进行详细说明,但本发明不受这些实施例的任何限定。
〔最低未占轨道(LUMO)的计算〕
对于实施例中使用的具有电子接受部位的化合物及在分子中具有咪唑部位及电子接受部位的化合物的最低未占轨道(LUMO),使用Gaussian 09,EM64L-G09Rev.B.01,在密度泛函法B3LYP/6-31G(d,p)水平的理论中,不考虑对称性地进行结构最优化,确认任一最优化的结构通过简谐振动频率计算而平稳点都为局部的最小值后,算出。将结果示于表1中。
〔实施例1〕
将2-乙基-4-甲基咪唑〔EMI〕与N-(2-乙基己基)邻苯二甲酰亚胺〔2EHPI〕以1:1的比率混合而得到均匀的混合物。将所得到的混合物的UV光谱〔EMI+2EHPI〕测定结果示于图1中。
作为比较,测定2-乙基-4-甲基咪唑的UV光谱〔EMI〕及N-(2-乙基己基)邻苯二甲酰亚胺的UV光谱〔2EHPI〕,将对这些UV光谱合计的情况的UV光谱〔sum(EMI+2EHPI)〕一并示于图1中。
由该结果确认,将2-乙基-4-甲基咪唑〔EMI〕与N-(2-乙基己基)邻苯二甲酰亚胺〔2EHPI〕以1:1的比率混合而均匀的混合物的UV光谱从EMI及2EHPI的UV光谱的合计值向长波长侧位移,确认形成了电荷转移络合物。
〔实施例2~18及比较例1〕
将双酚A型环氧树脂(BISAEP)、2-乙基-4-甲基咪唑(EMI)及作为具有电子接受部位的化合物的具体例子所例示的化合物以表1中记载的配合比(摩尔)配合,制造含有电荷转移络合物的固化性树脂组合物。使用所得到的固化性树脂组合物来实施下述的评价。
〔实施例19及20〕
将双酚A型环氧树脂(BISAEP)以及作为在分子中具有咪唑部位及电子接受部位的化合物的具体例子所例示的化合物以表1中记载的配合比(摩尔)配合来制造固化性树脂组合物。使用所得到的固化性树脂组合物来实施下述的评价。
〔固化性〕
将固化性树脂组合物放入玻璃瓶中,在150℃、加热固化1小时,将确认没有粘性、完全为固体状并固化的组合物设定为〇,将不是这样的组合物设定为×。
〔贮藏稳定性〕
将固化性树脂组合物以从下起成为五分之一的量加入到直径13mm、高度40mm的玻璃瓶中并盖上盖子。使其在平桌上倾斜90°,观察1分钟后的状态,确认是否具有流动性。固化性树脂组合物的形状见到变化的情况设定为具有流动性,没有变化的情况设定为无流动性。每放置1天进行评价,在流动性消失的时刻结束评价。将能够维持流动性的天数示于表1中。在能够维持3天以上流动性的情况下,判断贮藏稳定性为合格(〇),不满足其的情况判断为贮藏稳定性不合格(×)。
如上述实施例中所示的那样,得到新型的电荷转移络合物。此外,显然该电荷转移络合物作为环氧树脂固化剂是有用的,含有环氧树脂和该电荷转移络合物得到的固化性树脂组合物的固化性及贮藏稳定性优异。
产业上的可利用性
根据本发明,特别是能够提供固化性、贮藏稳定性优异的单组分固化型的固化性树脂组合物,例如可以适宜用于电子部件粘接剂、电子部件密封材料、铸型材料、涂料、结构粘接剂等。
Claims (10)
1.一种电荷转移络合物,其具有咪唑部位作为电子给予部位。
2.根据权利要求1所述的电荷转移络合物,其包含具有咪唑部位的化合物(a)和具有电子接受部位的化合物(b),其中,所述具有电子接受部位的化合物(b)接受了所述具有咪唑部位的化合物(a)中所含的电子。
3.根据权利要求2所述的电荷转移络合物,其中,具有电子接受部位的化合物(b)的最低未占轨道(LUMO)为-1eV以下。
4.根据权利要求2或3所述的电荷转移络合物,其中,具有电子接受部位的化合物(b)为具有酰亚胺部位的化合物。
5.根据权利要求1所述的电荷转移络合物,其是在分子中具有咪唑部位及电子接受部位的化合物中电子接受部位接受了咪唑部位中所含的电子而得到的电荷转移络合物。
6.根据权利要求5所述的电荷转移络合物,其中,在分子中具有咪唑部位及电子接受部位的化合物的最低未占轨道(LUMO)为-1eV以下。
7.根据权利要求5或6所述的电荷转移络合物,其中,电子接受部位为酰亚胺部位。
8.根据权利要求5~7中任一项所述的电荷转移络合物,其中,在分子中具有咪唑部位及电子接受部位的化合物为下述式(1)所表示的化合物,
通式(1)中,R1、R2及R3分别独立地表示氢原子或可具有取代基的碳原子数为1~20的烃基,R4表示可具有取代基的碳原子数1~10的二价的烃基,环A表示可具有取代基的苯环、可具有取代基的环己烷环或可具有取代基的降冰片烯环。
9.一种环氧树脂用固化剂,其由权利要求1~8中任一项所述的电荷转移络合物形成。
10.一种固化性树脂组合物,其含有环氧树脂及权利要求1~8中任一项所述的电荷转移络合物。
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