TWI564302B - A novel compound, a near infrared ray absorber, and a synthetic resin composition containing the same - Google Patents
A novel compound, a near infrared ray absorber, and a synthetic resin composition containing the same Download PDFInfo
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- TWI564302B TWI564302B TW101113663A TW101113663A TWI564302B TW I564302 B TWI564302 B TW I564302B TW 101113663 A TW101113663 A TW 101113663A TW 101113663 A TW101113663 A TW 101113663A TW I564302 B TWI564302 B TW I564302B
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- Taiwan
- Prior art keywords
- group
- carbon atoms
- synthetic resin
- substituent
- infrared absorbing
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- 229920003002 synthetic resin Polymers 0.000 title claims description 50
- 239000000057 synthetic resin Substances 0.000 title claims description 50
- 239000000203 mixture Substances 0.000 title claims description 30
- 239000006096 absorbing agent Substances 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 title description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 150000001639 boron compounds Chemical class 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000011358 absorbing material Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- -1 1,3-dimethylbutyl Chemical group 0.000 description 163
- 125000001424 substituent group Chemical group 0.000 description 66
- 238000010521 absorption reaction Methods 0.000 description 32
- 229920005989 resin Polymers 0.000 description 29
- 239000011347 resin Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 11
- 229910019142 PO4 Inorganic materials 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229920005992 thermoplastic resin Polymers 0.000 description 10
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 229920000515 polycarbonate Polymers 0.000 description 9
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 8
- 229920000877 Melamine resin Polymers 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
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- 229940097275 indigo Drugs 0.000 description 8
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 238000000862 absorption spectrum Methods 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002675 Polyoxyl Polymers 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 239000000976 ink Substances 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FGQBMYYYVDAGNF-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-[6-(2,2,6,6-tetramethylpiperidin-4-yl)hexyl]piperidine Chemical compound C1C(C)(C)NC(C)(C)CC1CCCCCCC1CC(C)(C)NC(C)(C)C1 FGQBMYYYVDAGNF-UHFFFAOYSA-N 0.000 description 2
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- VYTVPRWAGRDIIR-UHFFFAOYSA-N 2-aminoethyl diphenyl borate Chemical compound C=1C=CC=CC=1OB(OCCN)OC1=CC=CC=C1 VYTVPRWAGRDIIR-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229920001893 acrylonitrile styrene Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 description 2
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- 238000004040 coloring Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Chemical compound CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
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- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- Compositions Of Macromolecular Compounds (AREA)
Description
本發明係關於一種新穎硼化合物及其用途,詳細而言,係關於一種於近紅外區域具有吸收,作為近紅外線吸收劑之用於利用雷射光之資訊記錄材料(例如光學卡、有機光導電體、雷射熱轉印記錄、雷射熱敏記錄、雷射直接製版等)、要求近紅外線吸收能力(或吸熱能力)之器材(例如近紅外線吸收過濾器、電漿顯示器用過濾器、濾光器、薄型顯示器用濾光器、光半導體元件用濾光器、熱線屏蔽薄膜、熱線屏蔽樹脂玻璃、保護眼鏡、隱顯墨水、農業用薄膜、玻璃、汽車內外飾材、樹脂成形體等)等之新穎硼化合物。又,本發明係關於一種含有該化合物之合成樹脂組合物。
近年來,於近紅外區域具有吸收,用於利用雷射光之資訊記錄材料(例如光學卡、有機光導電體、雷射熱轉印記錄、雷射熱敏記錄、雷射直接製版等)、要求近紅外線吸收能力(或吸熱能力)之器材(例如近紅外線吸收過濾器、電漿顯示器用過濾器、濾光器、薄型顯示器用濾光器、光半導體元件用濾光器、熱線屏蔽薄膜、熱線屏蔽樹脂玻璃、保護眼鏡、隱顯墨水、農業用薄膜、玻璃、汽車內外飾材、樹脂成形體等)等之近紅外線吸收色素之要求提高。
作為近紅外線吸收色素,使用花青系色素、聚次甲基系色素、方酸菁系色素、卟啉系色素、金屬二硫醇錯合物系
色素、酞菁系色素、二亞銨系色素、無機氧化物粒子等。
然而,由於該等化合物之近紅外線吸收能力並不讓人滿意,又於可見光線之區域具有吸收波長,故而無法用於必需透明性之用途或忌著色之用途。特別是,於使用該等近紅外線吸收色素作為近紅外線吸收劑之情形時,較多地與熱塑性樹脂等合成樹脂組合而使用,此時,有與樹脂之相溶性之問題,或因於可見光線之區域具有吸收波長而有損樹脂之透明性、著色之問題,或除此之外損害樹脂之物性之情況較多。
因此,必需有於近紅外區域具有最大吸收波長,且可見光區域之吸收較小之化合物。
又,有對環境之負荷之問題、或於精密電子材料領域等根據用途(重)金屬元素之使用成為問題之情況,較理想的是除金屬錯合物以外之近紅外線吸收劑。
另一方面,雖然於非專利文獻1中記載有N靛藍錯合物,但其係β-雙烯酮亞胺基金屬(鈀)錯合物,由此無法獲得本發明之見解。
非專利文獻1:Chem.Commun,2010,Vol.46,pp.6753-6755
因此,本發明之目的在於:提供一種於近紅外線之波長
區域具有最大吸收波長,且可見光區域之吸收較小,作為近紅外線吸收劑優異之新穎硼化合物及使用其之近紅外線吸收劑。進而本發明提供一種含有該近紅外線吸收劑之近紅外線吸收性合成樹脂組合物。
本發明者為了解決上述問題而進行努力研究,結果發現,具有特定之結構之新穎硼化合物於近紅外線之波長區域具有最大吸收波長,並且可見光區域之吸收較小,作為近紅外線吸收劑優異,從而完成本發明。
即,本發明提供一種硼化合物,其係下述通式(1)所示:
(式中,R1~R16可互相相同亦可不同,且表示氫原子、鹵素原子、硝基、氰基、胺基、可具有取代基之碳原子數1~20之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數1~20之烷氧基、可具有取代基之碳原子數
6~20之芳氧基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數5~12之環烷基、可具有取代基之碳原子數1~20之烷硫基、可具有取代基之碳原子數6~20之芳硫基、可具有取代基之碳原子數1~20之烷基胺基、或可具有取代基之碳原子數6~20之芳基胺基;R1~R16所示之基之中相鄰之2個基亦可連結且分別與鍵結之碳原子共同形成5員環或6員環)。
又,本發明提供一種近紅外線吸收劑,其含有上述硼化合物。
又,本發明提供一種近紅外線吸收性合成樹脂組合物,其含有上述硼化合物。
又,本發明提供一種近紅外線吸收材料,其含有上述近紅外線吸收性合成樹脂組合物。
根據本發明,可提供一種於近紅外線之波長區域具有最大吸收波長,且可見光區域之吸收較小,作為近紅外線吸收劑優異之新穎硼化合物。又,本發明可提供一種含有該硼化合物之近紅外線吸收劑及近紅外線吸收性合成樹脂組合物。
以下,基於較佳之實施形態對本發明進行詳細敍述。
首先,對本發明之新穎硼化合物進行說明。本發明之新穎硼化合物係下述通式(1)所示:[化2]
(式中,R1~R16可互相相同亦可不同,且表示氫原子、鹵素原子、硝基、氰基、胺基、可具有取代基之碳原子數1~20之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數1~20之烷氧基、可具有取代基之碳原子數6~20之芳氧基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數5~12之環烷基、可具有取代基之碳原子數1~20之烷硫基、可具有取代基之碳原子數6~20之芳硫基、可具有取代基之碳原子數1~20之烷基胺基、或可具有取代基之碳原子數6~20之芳基胺基;R1~R16所示之基之中相鄰之2個基亦可連結且分別與鍵結之碳原子共同形成5員環或6員環)。
於上述通式(1)之中,若舉出R1~R16所示之鹵素原子之例,則可列舉:氟、氯、溴、碘等。
於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數1~20之烷基之例,則作為未經取代之碳原子數1~20之烷基,可列舉:甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、異戊基、
新戊基、第三戊基、1,2-二甲基丙基、正己基、環己基、1,3-二甲基丁基、1-異丙基丙基、1,2-二甲基丁基、正庚基、2-庚基、1,4-二甲基戊基、第三庚基、2-甲基-1-異丙基丙基、1-乙基-3-甲基丁基、正辛基、第三辛基、2-乙基己基、2-甲基己基、2-丙基己基、正壬基、異壬基、正癸基、異癸基、正十一烷基、異十一烷基、正十二烷基、異十二烷基、正十三烷基、異十三烷基、正十四烷基、異十四烷基、正十五烷基、異十五烷基、正十六烷基、異十六烷基、正十七烷基、異十七烷基、正十八烷基、異十八烷基、正十九烷基、異十九烷基、正二十烷基、異二十烷基等。作為具有取代基之碳原子數1~20之烷基,可列舉上述烷基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數1~20之烷氧基之例,則可列舉對應上述烷基者,具體而言,作為未經取代之碳原子數1~20之烷氧基,可列舉:甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、異戊氧基、新戊氧基、1,2-二甲基-丙氧基、正己氧基、環己氧基、1,3-二甲基丁氧基、1-異丙基丙氧基等。作為具有取代基之碳原子數1~20之烷氧基,可列舉上述烷氧基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數6~20之芳基之例,則作為未經取代之碳原子數6~20之芳基,可列舉:苯基、萘基、蒽-1-基、菲-1-
基等。作為具有取代基之碳原子數6~20之芳基,可列舉上述芳基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數6~20之芳氧基之例,則可列舉對應於上述芳基者,具體而言,作為未經取代之碳原子數6~20之芳氧基,可列舉:苯氧基、萘氧基等。作為具有取代基之碳原子數1~20之芳氧基,可列舉上述芳氧基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數7~20之芳基烷基之例,則作為未經取代之碳原子數7~20之芳基烷基,可列舉:苄基、苯乙基、2-苯基丙烷-2-基、苯乙烯基、苯烯丙基、二苯甲基、三苯甲基等。作為具有取代基之碳原子數7~20之芳基烷基,可列舉上述芳基烷基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數5~12之環烷基之例,則作為未經取代之碳原子數5~12之環烷基,可列舉:環戊基、環己基、環辛基、環十二烷基、4-甲基環己基等。作為具有取代基之碳原子數5~12之環烷基,可列舉上述環烷基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數1~20之烷硫基之例,則作為未經取代之碳原子數1~20之烷硫基,可列舉:甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、第二丁硫基、第三
丁硫基、正戊硫基、異戊硫基、新戊硫基、1,2-二甲基-丙硫基、正己硫基、環己硫基、正庚硫基、2-乙基己硫基、正辛硫基、正壬硫基等。作為具有取代基之碳原子數1~20之烷硫基,可列舉上述烷硫基經下述之取代基取代者,具體而言,可列舉:甲氧基乙硫基、乙氧基乙硫基、丙氧基乙硫基、丁氧基乙硫基、胺基乙硫基、正丁基胺基乙硫基、苄基胺基乙硫基、甲基羰基胺基乙硫基、苯基羰基胺基乙硫基、甲基磺醯基胺基乙硫基、苯基磺醯基胺基乙硫基、二甲基胺基乙硫基、二乙基胺基乙硫基等。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數6~20之芳硫基之例,則作為未經取代之碳原子數6~20之芳硫基,可列舉:苯硫基、萘硫基等。作為具有取代基之碳原子數6~20之芳硫基,可列舉上述芳硫基經下述之取代基取代者,具體而言,可列舉:4-甲基苯硫基、4-乙基苯硫基、4-丙基苯硫基、4-第三丁基苯硫基、4-甲氧基苯硫基、4-乙氧基苯硫基、4-胺基苯硫基、4-烷基胺基苯硫基、4-二烷基胺基苯硫基、4-苯基胺基苯硫基、4-二苯基胺基苯硫基、4-羥基苯硫基、4-氯苯硫基、4-溴苯硫基、2-甲基苯硫基、2-乙基苯硫基、2-丙基苯硫基、2-第三丁基苯硫基、2-甲氧基苯硫基、2-乙氧基苯硫基、2-胺基苯硫基、2-烷基胺基苯硫基、2-二烷基胺基苯硫基、2-苯基胺基苯硫基、2-二苯基胺基苯硫基、2-羥基苯硫基、4-二甲基胺基苯硫基、4-甲基胺基苯硫基、4-甲基羰基胺基苯硫基、4-苯基羰基胺基苯硫基、4-甲基磺醯
基胺基苯硫基、4-苯基磺醯基胺基苯硫基等。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數1~20之烷基胺基之例,則作為未經取代之碳原子數1~20之烷基胺基,可列舉:甲基胺基、乙基胺基、正丙基胺基、異丙基胺基、丁基胺基、戊基胺基、二戊基胺基、己基胺基、庚基胺基、辛基胺基、2-乙基己基胺基、壬基胺基、苄基胺基、二甲基胺基、二乙基胺基、二正丙基胺基、二異丙基胺基、二丁基胺基、二戊基胺基、二己基胺基、二庚基胺基、二辛基胺基、二2-乙基己基胺基、二壬基胺基、甲基乙基胺基等。作為具有取代基之碳原子數1~20之烷基胺基,可列舉上述烷基胺基經下述之取代基取代者。
又,於上述通式(1)之中,若舉出R1~R16所示之可具有取代基之碳原子數6~20之芳基胺基之例,則作為未經取代之碳原子數6~20之芳基胺基,可列舉:苯基胺基、萘基胺基、二苯基胺基等。作為具有取代基之碳原子數6~20之芳基胺基,可列舉上述芳基胺基經下述之取代基取代者,具體而言,可列舉:4-甲基苯基胺基、4-甲氧基苯基胺基、羥基苯基胺基等。
又,於上述通式(1)之中,R1~R16所示之基之中相鄰之2個基亦可連結且分別與鍵結之碳原子共同形成5員環或6員環。該5員環或6員環亦可具有取代基。作為此種5員環,可列舉:環戊烯環、環戊二烯環、咪唑環、噻唑環、吡唑環、唑環、異唑環、噻吩環、呋喃環、吡咯環等,
又,作為6員環,可列舉:環己烷環、環己烯環、環己二烯環、苯環、吡啶環、哌環、哌啶環、嗎啉環、吡環、吡喃酮環、吡咯啶環等。
又,於上述通式(1)之中,作為R1~R16所示之可具有取代基之碳原子數1~20之烷基、可具有取代基之碳原子數1~20之烷氧基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數6~20之芳氧基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數5~12之環烷基、可具有取代基之碳原子數1~20之烷硫基、可具有取代基之碳原子數1~20之烷基胺基、可具有取代基之碳原子數6~20之芳基胺基、上述R1~R16所示之基之中相鄰之基連結而形成之可具有取代基之5員環或6員環之該取代基,可列舉以下者。再者,R1~R16係含有上述之碳原子之基,且該等基在以下之取代基之中,於具有含有碳原子之取代基之情形時,含有該取代基之R1~R16全體之碳原子數滿足所規定之範圍。
作為上述取代基,例如可列舉:甲基、乙基、丙基、異丙基、環丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、環戊基、己基、2-己基、3-己基、環己基、聯環己基、1-甲基環己基、庚基、2-庚基、3-庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基、壬基、異壬基、癸基等烷基;甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基、異丁氧基、戊氧基、異戊氧基、第三
戊氧基、己氧基、環己氧基、庚氧基、異庚氧基、第三庚氧基、正辛氧基、異辛氧基、第三辛氧基、2-乙基己氧基、壬氧基、癸氧基等烷氧基;甲硫基、乙硫基、丙硫基、異丙硫基、丁硫基、第二丁硫基、第三丁硫基、異丁硫基、戊硫基、異戊硫基、第三戊硫基、己硫基、環己硫基、庚硫基、異庚硫基、第三庚硫基、正辛硫基、異辛硫基、第三辛硫基、2-乙基己硫基等烷硫基;乙烯基、1-甲基乙烯基、2-甲基乙烯基、2-丙烯基、1-甲基-3-丙烯基、3-丁烯基、1-甲基-3-丁烯基、異丁烯基、3-戊烯基、4-己烯基、環己烯基、聯環己烯基、庚烯基、辛烯基、癸烯基、十五烯基、二十烯基、三十烯基等烯基;苄基、苯乙基、二苯甲基、三苯甲基、苯乙烯基、苯烯丙基等芳基烷基;苯基、萘基等芳基;苯氧基、萘氧基等芳氧基;苯硫基、萘硫基等芳硫基;吡啶基、嘧啶基、嗒基、哌啶基、吡喃基、吡唑基、三基、吡咯基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基、呋喃基、苯并呋喃基、噻吩基、苯硫基、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑基、異噻唑基、異唑基、吲哚基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基、
2,4-二氧基唑啶-3-基等雜環基;氟、氯、溴、碘等鹵素原子;乙醯基、2-氯乙醯基、丙醯基、辛醯基、丙烯醯基、甲基丙烯醯基、苯基羰基(苯甲醯基)、酞醯基、4-三氟甲基苯甲醯基、三甲基乙醯基、鄰羥苯甲醯基、草醯基、硬脂醯基、甲氧基羰基、乙氧基羰基、第三丁氧基羰基、正十八烷氧基羰基、胺甲醯基等醯基;乙醯氧基、苯甲醯氧基等醯氧基;胺基、乙基胺基、二甲基胺基、二乙基胺基、丁基胺基、環戊基胺基、2-乙基己基胺基、十二烷基胺基、苯胺基、氯苯基胺基、甲苯胺基、甲氧苯胺基、N-甲基-苯胺基、二苯基胺基、萘基胺基、2-吡啶基胺基、甲氧基羰基胺基、苯氧基羰基胺基、乙醯基胺基、苯甲醯基胺基、甲醯胺基、三甲基乙醯基胺基、月桂醯基胺基、胺甲醯基胺基、N,N-二甲基胺基羰基胺基、N,N-二乙基胺基羰基胺基、嗎啉基羰基胺基、甲氧基羰基胺基、乙氧基羰基胺基、第三丁氧基羰基胺基、正十八烷氧基羰基胺基、N-甲基-甲氧基羰基胺基、苯氧基羰基胺基、胺磺醯基胺基、N,N-二甲基胺基磺醯基胺基、甲基磺醯基胺基、丁基磺醯基胺基、苯基磺醯基胺基等取代胺基;硫醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、亞胺基、胺甲醯基、磺醯胺基等;該等基亦可進而經取代。又,羧基及磺基亦可形成鹽。
作為於上述通式(1)中之R1~R16,就近紅外線吸收能力方
面而言,較佳為氫原子或烷基,更佳為氫原子或甲基,最佳為氫原子。
作為本發明之上述通式(1)所示之新穎化合物之具體例,可列舉下述之化合物No.1~No.14,但並不限於該等化合物。
其次,對本發明之上述通式(1)所示之硼化合物之合成方法進行說明。
首先,對由原料之具有靛藍骨架之化合物獲得中間物之步驟進行說明。於本步驟中,於溶劑中,於存在四氯化鈦與1,4-二氮雜雙環[2.2.2]辛烷(DABCO)之情況下使具有靛
藍骨架之化合物與具有苯胺骨架之化合物進行反應而獲得中間物。例如,於將靛藍作為原料,合成用以合成上述化合物No.1之中間物-1之情形之流程,為下述流程1。
用於獲得中間物之反應溶劑,只要不使四氯化鈦與DABCO減活,則並無特別限定,但較佳為溶解具有靛藍骨架之化合物者,作為具體例,可列舉:芳香族系溶劑(甲苯、二甲苯、氯苯、硝基苯、均三甲苯、對異丙基甲苯、二氯苯、石腦油溶劑)或脂肪族系高沸點溶劑(癸烷等)等。較佳為甲苯、二甲苯、氯苯、鄰二氯苯、均三甲苯、及溴苯,更佳為溴苯。
反應溫度並無特別限定,較佳為對溶解作為原料之具有靛藍骨架之化合物所必需之溫度,較佳為使其於所使用之溶劑回流之溫度下進行反應。就該等方面而言,較佳為100℃~200℃之範圍,更佳為130℃~180℃。
反應時間並無特別限定,只要藉由HPLC或TLC確認反應之進行,直至反應結束即可。反應結束之後,亦可進行萃取處理或純化處理等後處理。
所使用之具有苯胺骨架之化合物之使用量,相對於具有靛藍骨架之化合物1莫耳,必需為2莫耳以上,較佳為3~4莫耳。
又,所使用之四氯化鈦之使用量,相對於具有靛藍骨架之化合物1莫耳,較佳為2~3莫耳。
又,所使用之DABCO之使用量,相對於具有靛藍骨架之化合物1莫耳,較佳為8~12莫耳。
其次,對由中間物獲得本發明之上述通式(1)所示之硼化合物之步驟進行說明。於本步驟中,於溶劑中,於存在硼酸酯等硼化合物與四氯化鈦等路易斯酸之情況下使於上述之步驟所得之中間物進行反應而獲得本發明之硼化合物。例如,用以由在上述流程1所得之中間物-1,獲得作為本發明之硼化合物之化合物No.1之流程,為下述流程2。
用於由中間物獲得上述通式(1)所示之硼化合物之反應溶劑,只要不使四氯化鈦等路易斯酸減活,則並無特別限
定,但較佳為溶解中間物者,作為具體例,可列舉:芳香族系溶劑(甲苯、二甲苯、氯苯、硝基苯、均三甲苯、對異丙基甲苯、二氯苯、石腦油溶劑)或脂肪族系高沸點溶劑(癸烷等)等。較佳為甲苯、二甲苯、氯苯、鄰二氯苯、均三甲苯、及溴苯,更佳為甲苯。
反應溫度並無特別限定,但較佳為對溶解中間物所必需之溫度,較佳為使其於所使用之溶劑回流之溫度下進行反應。就該等方面而言,較佳為50℃~170℃之範圍,更佳為70℃~150℃,進而較佳為90℃~130℃。
反應時間並無特別限定,只要藉由HPLC或TLC確認反應之進行,直至反應結束即可。反應結束之後,亦可對所使用之路易斯酸進行去活化處理等後處理或萃取處理、晶析等純化處理。
所使用之硼化合物,較佳為硼酸酯,特佳為二苯基硼酸2-胺基乙酯。所使用之硼化合物之使用量,相對於中間物1莫耳,為2莫耳以上,較佳為2.0~2.2莫耳。
所使用之路易斯酸並無特別限定,但較佳為四氯化鈦、氯化鋁、氯化鐵、氯化鋅、氯化錫、三氟化硼、及該等之溴化物,更佳為氯化鈦、三氟化硼、及氯化鋁,最佳為四氯化鈦。所使用之路易斯酸之使用量,相對於中間物1莫耳,較佳為1~4.4莫耳。
以上所說明之本發明之上述通式(1)所示之硼化合物,於近紅外線區域具有吸收,又,可見光區域之吸收較少,故而適合用作近紅外線吸收劑。
上述通式(1)所示之硼化合物之光吸收特性並無特別限定,但考慮到作為近紅外線吸收劑之用途,較佳為於700~1050 nm,尤其,700~1000 nm具有吸收最大值者。又,較佳為選擇性吸收波長700~1000 nm之近紅外線。又,較佳為可見光區域之吸收更少者。
其次,對本發明之近紅外線吸收劑、近紅外線吸收性合成樹脂組合物及近紅外線吸收材料進行說明。
本發明之近紅外線吸收劑係含有本發明之上述通式(1)所示之硼化合物者,亦可為本發明之上述通式(1)所示之硼化合物本身,亦可為適當調配有本發明之近紅外線吸收性合成樹脂組合物中可使用之任意之添加劑者,除本發明之硼化合物以外之成分並無特別限定。
由於本發明之近紅外線吸收劑(本發明之上述通式(1)所示之硼化合物))之可見光區域之吸收較少,即便合成樹脂使用其,亦無損樹脂之透明性,不影響樹脂本來之顏色,故而較佳為用作近紅外線吸收性合成樹脂組合物。又,由於耐熱性優異,故而較佳為用作於熱塑性樹脂中作為捏合型之近紅外線吸收劑而調配之近紅外線吸收性熱塑性樹脂組合物。
本發明之近紅外線吸收劑中之上述通式(1)所示之硼化合物之含量並無特別限定,但於合成樹脂使用其之情形時,較佳為成為於下述之近紅外線吸收性合成樹脂組合物中之上述通式(1)所示之硼化合物之含量之範圍。
本發明之近紅外線吸收性合成樹脂組合物係使合成樹脂
中含有本發明之近紅外線吸收劑(上述通式(1)所示之硼化合物)者。
作為可用於本發明之合成樹脂,可列舉:熱塑性樹脂、熱硬化性樹脂、氟樹脂、矽樹脂等。
作為上述熱塑性樹脂之例,可列舉:聚丙烯、高密度聚乙烯、低密度聚乙烯、直鏈低密度聚乙烯、交聯聚乙烯、超高分子量聚乙烯、聚丁烯-1、聚-3-甲基戊烯、聚-4-甲基戊烯等α-烯烴聚合物或乙烯-乙酸乙烯酯共聚物、乙烯-丙烯酸乙酯共聚物、乙烯-丙烯共聚物等聚烯烴系樹脂及該等之共聚物;聚氯乙烯、聚偏二氯乙烯、氯化聚乙烯、氯化聚丙烯、聚偏二氟乙烯、氯化橡膠、氯化乙烯-乙酸乙烯酯共聚物、氯化乙烯-乙烯共聚物、氯化乙烯-偏二氯乙烯共聚物、氯化乙烯-偏二氯乙烯-乙酸乙烯酯三元共聚物、氯乙烯-丙烯酸酯共聚物、氯乙烯-順丁烯二酸酯共聚物、氯乙烯-環己基馬來醯亞胺共聚物等含鹵素樹脂;石油樹脂、香豆酮樹脂、聚苯乙烯、聚乙酸乙烯酯、丙烯酸樹脂、苯乙烯及/或α-甲基苯乙烯與其他單體(例如順丁烯二酸酐、苯基馬來醯亞胺、甲基丙烯酸甲酯、丁二烯、丁烯腈等)之共聚物(例如AS(acrylonitrile-styrene,丙烯腈-苯乙烯)樹脂、ABS(acrylonitrile-butadiene-styrene,丙烯腈-丁二烯-苯乙烯)樹脂、ACS(acrylonitrile-chlorinated polyethylene-styrene,丙烯腈-氯化聚乙烯-苯乙烯三元共聚)樹脂、SBS(styrene-butadiene-styrene,苯乙烯-丁二烯-苯乙烯)樹脂、MBS(methyl methacrylate-butadiene-
styrene,甲基丙烯酸甲酯-丁二烯-苯乙烯)樹脂、耐熱ABS樹脂等);聚甲基丙烯酸甲酯、聚乙烯醇、聚乙烯甲醛、聚乙烯丁醛;聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯、聚對苯二甲酸環己二甲酯等聚對苯二甲酸烷二酯、聚萘二甲酸乙二酯、聚萘二甲酸丁二酯等聚萘二甲酸烷二酯等芳香族聚酯及聚對苯二甲酸丁二酯等直鏈聚酯;聚羥丁酸酯、聚己內酯、聚丁二酸丁二酯、聚丁二酸乙二酯、聚乳酸、聚蘋果酸、聚乙醇酸、聚二烷、聚(2-氧雜環丁酮)等分解性脂肪族聚酯;聚苯醚、聚己內醯胺及聚己二醯己二胺等聚醯胺、聚碳酸酯、聚碳酸酯/ABS樹脂、分支聚碳酸酯、聚縮醛、聚苯硫醚、聚胺基甲酸酯、纖維素系樹脂、聚醯亞胺樹脂等熱塑性樹脂及該等之混合物。
進而,上述熱塑性樹脂亦可為異戊二烯橡膠、丁二烯橡膠、丁烯腈-丁二烯共重合橡膠、苯乙烯-丁二烯共重合橡膠、氟橡膠、聚矽氧橡膠、烯烴系彈性體、苯乙烯系彈性體、聚酯系彈性體、腈系彈性體、尼龍系彈性體、氯乙烯系彈性體、聚醯胺系彈性體、聚胺基甲酸酯系彈性體等彈性體。
作為上述熱硬化性樹脂之例,可列舉:苯酚樹脂、脲樹脂、三聚氰胺樹脂、環氧樹脂、不飽和聚酯樹脂等。
作為上述氟樹脂之例,可列舉:聚四氟乙烯、聚偏二氟乙烯、聚氯三氟乙烯、聚氟乙烯、全氟烷氧基氟樹脂、四氟乙烯-乙烯共聚物等。
作為上述矽樹脂之例,可列舉:二甲基聚矽氧樹脂、甲
基苯基聚矽氧樹脂、甲基乙烯基聚矽氧樹脂、環氧改性聚矽氧樹脂、丙烯酸改性聚矽氧樹脂等。
進而若舉出合成樹脂之例,則可列舉:聚矽氧橡膠聚醚碸、聚碸、聚苯醚、聚醚酮、聚醚醚酮、液晶聚合物等。
於本發明中,可單獨使用該等合成樹脂,亦可使用2種以上。又,亦可將該等合成樹脂進行合金化。
該等合成樹脂可不拘泥於分子量、聚合度、密度、軟化點、不溶成分對溶劑之比例、立體規則性之程度、觸媒殘渣之有無、成為原料之單體之種類或調配比率、聚合觸媒之種類(例如,齊格勒觸媒、茂金屬觸媒等)等而使用。
於上述合成樹脂之中,就上述通式(1)所示之硼化合物之相溶性與加工性方面而言,較佳為熱塑性樹脂,於熱塑性樹脂之中,就透明性與近紅外線吸收性而言,特佳為聚碳酸酯、聚甲基丙烯酸甲酯。
本發明之近紅外線吸收性合成樹脂組合物中,上述通式(1)所示之硼化合物之含量,相對於上述合成樹脂100質量份,較佳為0.001~20質量份,更佳為0.01~10質量份,最佳為0.1~5質量份。若上述通式(1)所示之硼化合物之含量未達0.001質量份,則有無法達成充分之近紅外線吸收能力之可能性;反之,若超過20質量份,則有無法獲得與使用量相稱之效果且不經濟,並且損害可見光區域之透明性之可能性。
上述通式(1)所示之硼化合物之對合成樹脂之調配方法只要依據常法即可,並無特別限定。例如,於使用熱塑性
樹脂作為合成樹脂之情形時,可使用通常調配各種添加劑於熱塑性樹脂中時所使用之任意之方法,例如,只要藉由輥混練、保險桿混練、擠出機、捏合機等加以混合、捏合而調配即可。
又,於各種溶劑中,亦可溶解或分散上述通式(1)所示之硼化合物與上述合成樹脂,調配近紅外線吸收性合成樹脂組合物溶液而使用。
於本發明之近紅外線吸收性合成樹脂組合物之中,視需要,亦可調配苯酚系抗氧化劑、磷系抗氧化劑、硫醚系抗氧化劑、紫外線吸收劑、受阻胺系光穩定劑等合成樹脂中所使用之添加劑,並使其穩定。
作為上述苯酚系抗氧化劑,例如可列舉:2,6-二第三丁基-對甲酚、2,6-二苯基-4-十八烷氧基苯酚、二硬脂基(3,5-二第三丁基-4-羥基苄基)磷酸酯、1,6-環己烷雙[(3,5-二第三丁基-4-羥基苯基)丙酸醯胺]、4,4'-硫代雙(6-第三丁基-間甲酚)、2,2'-亞甲基雙(4-甲基-6-第三丁基苯酚)、2,2'-亞甲基雙(4-乙基-6-第三丁基苯酚)、4,4'-亞丁基雙(6-第三丁基-間甲酚)、2,2'-亞乙基雙(4,6-二第三丁基苯酚)、2,2'-亞乙基雙(4-第二丁基-6-第三丁基苯酚)、1,1,3-三(2-甲基-4-羥基-5-第三丁基苯基)丁烷、1,3,5-三(2,6-二甲基-3-羥基-4-第三丁基苄基)異氰尿酸酯、1,3,5-三(3,5-二第三丁基-4-羥基苄基)異氰尿酸酯、1,3,5-三(3,5-二第三丁基-4-羥基苄基)-2,4,6-三甲基苯、2-第三丁基-4-甲基-6-(2-丙烯醯氧基-3-第三丁基-5-甲基苄基)苯酚、十八烷基(3,5-二
第三丁基-4-羥基苯基)丙酸酯、四[3-(3,5-二第三丁基-4-羥基苯基)丙酸甲酯]甲烷、硫代二乙二醇雙[(3,5-二第三丁基-4-羥基苯基)丙酸酯]、1,6-環己烷雙[(3,5-二第三丁基-4-羥基苯基)丙酸酯]、雙[3,3-雙(4-羥基-3-第三丁基苯基)酪酸]二醇酯、雙[2-第三丁基-4-甲基-6-(2-羥基-3-第三丁基-5-甲基苄基)苯基]對苯二甲酸酯、1,3,5-三[(3,5-二第三丁基-4-羥基苯基)丙醯氧基乙基]異氰尿酸酯、3,9-雙[1,1-二甲基-2-{(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基}乙基]-2,4,8,10-四氧雜螺[5,5]十一烷、三乙二醇雙[(3-第三丁基-4-羥基-5-甲基苯基)丙酸酯]等。
上述苯酚系抗氧化劑之含量,相對於合成樹脂100質量份,較佳為0.001~10質量份,更佳為0.05~5質量份。
作為上述磷系抗氧化劑,例如可列舉:亞磷酸三壬基苯酯、三[2-第三丁基-4-(3-第三丁基-4-羥基-5-甲基苯硫基)-5-甲基苯基]亞磷酸酯、亞磷酸十三烷基酯、亞磷酸辛基二苯酯、亞磷酸二(癸基)單苯酯、二(十三烷基)季戊四醇二亞磷酸酯、二(壬基苯基)季戊四醇二亞磷酸酯、雙(2,4-二第三丁基苯基)季戊四醇二亞磷酸酯、雙(2,6-二第三丁基-4-甲基苯基)季戊四醇二亞磷酸酯、雙(2,4,6-三第三丁基苯基)季戊四醇二亞磷酸酯、雙(2,4-二異丙苯基苯基)季戊四醇二亞磷酸酯、四(十三烷基)異亞丙基二苯酚二亞磷酸酯、四(十三烷基)-4,4'-正亞丁基雙(2-第三丁基-5-甲基苯酚)二亞磷酸酯、六(十三烷基)-1,1,3-三(2-甲基-4-羥基-5-第三丁基苯基)丁烷三亞磷酸酯、二亞膦酸四(2,4-二第三
丁基苯基)伸聯苯酯、9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、亞磷酸2,2'-亞甲基雙(4,6-第三丁基苯基)-2-乙基己酯、亞磷酸2,2'-亞甲基雙(4,6-第三丁基苯基)-十八烷基酯、2,2'-亞乙基雙(4,6-二第三丁基苯基)氟亞磷酸酯、三(2-[(2,4,8,10-四第三丁基二苯[d,f][1,3,2]二磷環庚烷-6-基)氧基]乙基)胺、2-乙基-2-丁基丙二醇及2,4,6-三第三丁基苯酚之亞磷酸酯等。
上述磷系抗氧化劑之含量,相對於合成樹脂100質量份,較佳為0.001~10質量份,更佳為0.05~5質量份。
作為上述硫醚系抗氧化劑,例如可列舉:硫代二丙酸二月桂酯、硫代二丙酸二肉豆蔻酯、硫代二丙酸二硬脂酯等硫代二丙酸二烷基酯類,及季戊四醇四(β-烷基巰基丙酸酯)類。
上述硫醚系抗氧化劑之含量,相對於合成樹脂100質量份,較佳為0.001~10質量份,更佳為0.05~5質量份。
作為上述紫外線吸收劑,例如可列舉:2,4-二羥基二苯甲酮、2-羥基-4-甲氧基二苯甲酮、2-羥基-4-辛氧基二苯甲酮、5,5'-亞甲基雙(2-羥基-4-甲氧基二苯甲酮)等2-羥基二苯甲酮類;2-(2'-羥基-5'-甲基苯基)苯并三唑、2-(2'-羥基-3',5'-二第三丁基苯基)-5-氯苯并三唑、2-(2'-羥基-3'-第三丁基-5'-甲基苯基)-5-氯苯并三唑、2-(2'-羥基-5'-第三辛基苯基)苯并三唑、2-(2'-羥基-3',5'-二異丙苯基苯基)苯并三唑、2,2'-亞甲基雙(4-第三辛基-6-(苯并三唑)苯酚)、2-(2'-羥基-3'-第三丁基-5'-羧基苯基)苯并三唑等2-(2'-羥基苯基)
苯并三唑類;水楊酸苯酯、間苯二酚單苯甲酸酯、2,4-二第三丁基苯基-3,5-二第三丁基-4-羥基苯甲酸酯、2,4-二第三戊基苯基-3,5-二第三丁基-4-羥基苯甲酸酯、十六烷基-3,5-二第三丁基-4-羥基苯甲酸酯等苯甲酸酯類;2-乙基-2'-乙氧基草醯替苯胺、2-乙氧基-4'-十二烷基草醯替苯胺等羥取代草醯替苯胺類;丙烯酸乙基-α-氰基-β,β-二苯酯、甲基-2-氰基-3-甲基-3-(對甲氧基苯基)丙烯酸酯等氰基丙烯酸酯類;2-(2-羥基-4-辛氧基苯基)-4,6-雙(2,4-二第三丁基苯基)-均三、2-(2-羥基-4-甲氧基苯基)-4,6-二苯基-均三、2-(2-羥基-4-丙氧基-5-甲基苯基)-4,6-雙(2,4-二第三丁基苯基)-均三等三芳基三類。
上述紫外線吸收劑之含量,相對於合成樹脂100質量份,較佳為0.001~30質量份,更佳為0.05~10質量份。
作為上述受阻胺系光穩定劑,例如可列舉:2,2,6,6-四甲基-4-哌啶基硬脂酸酯、1,2,2,6,6-五甲基-4-哌啶基硬脂酸酯、2,2,6,6-四甲基-4-哌啶基苯甲酸酯、雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、四(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、雙(2,2,6,6-四甲基-4-哌啶基)-二(十三烷基)-1,2,3,4-丁烷四羧酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)-二(十三烷基)-1,2,3,4-丁烷四羧酸酯、雙(1,2,2,4,4-五甲基-4-哌啶基)-2-丁基-2-(3,5-二第三丁基-4-羥基苄基)丙二酸酯、1-(2-羥基
乙基)-2,2,6,6-四甲基-4-哌啶基/丁二酸二乙酯縮聚物、1,6-雙(2,2,6,6-四甲基-4-哌啶基胺基)己烷/2,4-二氯-6-嗎啉基-均三縮聚物、1,6-雙(2,2,6,6-四甲基-4-哌啶基胺基)己烷/2,4-二氯-6-第三辛基胺基-均三縮聚物、1,5,8,12-四[2,4-雙(正丁基-N-(2,2,6,6-四甲基-4-哌啶基)胺基)-均三-6-基]-1,5,8,12-四氮雜十二烷、1,5,8,12-四[2,4-雙(正丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)胺基)-均三-6-基]-1,5,8-12-四氮雜十二烷、1,6,11-三[2,4-雙(正丁基-N-(2,2,6,6-四甲基-4-哌啶基)胺基)-均三-6-基]胺基十一烷、1,6,11-三[2,4-雙(正丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)胺基)-均三-6-基]胺基十一烷等受阻胺化合物。
上述受阻胺系光穩定劑之含量,相對於合成樹脂100質量份,較佳為0.001~30質量份,更佳為0.05~10質量份。
進而於本發明之近紅外線吸收性合成樹脂組合物之中,視需要,亦可添加通常調配於對第三丁基苯甲酸鋁、芳香族磷酸酯金屬鹽、二亞苯基山梨醇類等成核劑、抗靜電劑、金屬皂、水滑石、含三環之化合物、金屬氫氧化物、磷酸酯系阻燃劑、縮合磷酸酯系阻燃劑、磷酸酯系阻燃劑、無機磷系阻燃劑、(聚)磷酸酯系阻燃劑、鹵素系阻燃劑、矽系阻燃劑、三氧化銻等氧化銻、其他之無機系阻燃助劑、其他之有機系阻燃助劑、填充劑、顏料、潤滑劑、發泡劑等合成樹脂中之添加劑。
作為上述含三環之化合物,例如可列舉:三聚氰胺、三聚氰酸二醯胺、苯胍胺、乙胍、鄰苯二甲醯二胍胺、
氰尿酸三聚氰胺、焦磷酸三聚氰胺、伸丁基二胍胺、降烯二胍胺、亞甲基二胍胺、乙烯基二(三聚氰胺)、三亞甲基二(三聚氰胺)、四亞甲基二(三聚氰胺)、六亞甲基二(三聚氰胺)、1,3-伸乙基二(三聚氰胺)等。
作為上述金屬氫氧化物,例如可列舉:氫氧化鎂、氫氧化鋁、氫氧化鈣、氫氧化鋇、氫氧化鋅、Kisuma 5A(氫氧化鎂:協和化學工業(股)製造)等。
作為上述磷酸酯系阻燃劑,例如可列舉:磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、磷酸三丁氧基乙酯、磷酸三氯乙酯、磷酸三(二氯丙酯)、磷酸三苯酯、磷酸三甲苯酯、磷酸甲苯基二苯酯、磷酸三(二甲苯酯)、磷酸辛基二苯酯、磷酸二甲苯二苯酯、磷酸三異丙基苯酯、磷酸2-乙基己基二苯酯、磷酸第三丁基苯基二苯酯、磷酸雙-(第三丁基苯基)苯酯、磷酸三-(第三丁基苯基)酯、磷酸異丙基苯基二苯酯、磷酸雙-(異丙基苯基)二苯酯、磷酸三-(異丙基苯基)酯等。
作為上述縮合磷酸酯系阻燃劑,例如可列舉:1,3-伸苯基-雙(磷酸二苯酯)、1,3-伸苯基-雙(磷酸二(二甲苯酯))、雙苯酚A-雙(磷酸二苯酯)等。
作為上述(聚)磷酸鹽系阻燃劑,例如可列舉:聚磷酸銨、聚磷酸三聚氰胺、聚磷酸哌、焦磷酸三聚氰胺、焦磷酸哌等(聚)磷酸之銨鹽或胺鹽。
作為上述其他之無機系阻燃助劑,例如可列舉:氧化鈦、氧化鋁、氧化鎂、水滑石、滑石、蒙脫石等無機化合
物,及其表面處理品,作為市售品,例如可列舉TIPAQUE R-680(氧化鈦:石原產業(股)製造)、Kyowamag 150(氧化鎂:協和化學工業(股)製造)、DHT-4A(水滑石:協和化學工業(股)製造)、Alcamizer 4(鋅改性水滑石:協和化學工業(股)製造)等。
作為上述其他之有機系阻燃助劑,例如可列舉季戊四醇。
另外,於本發明之近紅外線吸收性合成樹脂組合物之中,視需要,在不損及本發明之效果之範圍內可調配通常合成樹脂中所使用之添加劑,例如交聯劑、防霧劑、防離水展著劑、表面處理劑、塑化劑、潤滑劑、阻燃劑、防霧劑、螢光劑、防黴劑、殺菌劑、發泡劑、金屬減活劑、脫模劑、顏料、加工助劑、抗氧化劑、光穩定劑等。
於本發明之近紅外線吸收性合成樹脂組合物中,於使用上述通式(1)所示之硼化合物及上述合成樹脂以外之任意之添加劑之情形時,其使用量可根據添加劑之種類等而適當選擇,但就不損及本發明之效果之觀點而言,較佳為相對於合成樹脂100質量份,合計為20質量份以下。
本發明之近紅外線吸收性合成樹脂組合物,藉由成形可製成作為近紅外線吸收材料之成形體。成形方法並無特別限定,可列舉:擠壓加工、壓光加工、射出成形、輥、加壓成形、吹塑成形等,可製造樹脂板、片材、薄膜、纖維、異形品等各種形狀之成形品。
又,藉由溶解本發明之近紅外線吸收性合成樹脂組合物
於各種溶劑中製作澆鑄薄膜,可製作近紅外線吸收薄膜作為近紅外線吸收材料。
藉由本發明之近紅外線吸收性合成樹脂組合物所得之近紅外線吸收材料之近紅外線吸收能力優異。
本發明之近紅外線吸收性合成樹脂組合物及近紅外線吸收材料可用於必需近紅外線吸收能力(吸熱能力)之以下各種用途:光學卡、有機光導電體、雷射熱轉印記錄材料、雷射熱敏記錄材料、雷射直接製版用材料等光資訊記錄材料;電漿顯示器用過濾器、薄型顯示器用濾光器、光半導體元件用濾光器等以近紅外線吸收為目的之各種濾光器;熱線屏蔽材料、熱線屏蔽薄膜、熱線屏蔽樹脂玻璃;保溫蓄熱纖維;保護眼鏡、農業用薄膜、汽車內外飾材、片材、其他各種樹脂成形體;隱顯墨水、塗層材等。
以下,藉由實施例等進而對本發明進行具體說明。再者,於以下之實施例等之中,只要無特別記載,%及ppm係質量基準。
於100ml四口燒瓶中加入苯胺0.6 ml(6.6 mmol)、溴苯40 ml、及二氮雜雙環辛烷2.1 g(19 mmol),於氬氣中進行攪拌。然後,滴加四氯化鈦1 mol/l甲苯溶液4.8 ml(4.8 mmol)。於滴加結束後,加入靛藍0.55 g(2.1 mmol)於回流狀態下使其反應10小時。於反應結束後,加入丙酮並進行過濾,濃縮濾液而獲得綠色粉末。利用二氯甲烷及水將其
進行油水分離,並且濃縮有機相,藉此獲得0.5 g藏青色粉末之下述結構之中間物-1(產率58%)。
於三口燒瓶中並於氮氣環境氣體下2小時加熱回流0.2 g(0.5 mmol)所得之中間物-1、0.24 g(1.05 mmol)二苯基硼酸2-胺基乙酯、0.38 g(0.38 mmol)四氯化鈦、及50 ml甲苯。於室溫下冷卻後,加入甲醇,藉由過濾,獲得0.1 g藏青色結晶粉末。
對所得之藏青色結晶粉末進行FT-IR測定及1H-NMR測定。將利用FT-IR測定所得之分析結果示於下文中,將利用1H-NMR測定所得之分析結果示於[圖1]中。根據該等之測定結果,所得之粉末鑑定為下述結構式之化合物No.1。
FT-IR測定結果(cm-1)
3448、1685、1639、1608、1577、1531、1492、1473、1454、1431、1381、1330、1300、1207、1126、1072、1022、983、864、744、694
又,測定所得之化合物No.1之丙酮溶液(濃度8 mw%)之吸收光譜。測定係藉由日本分光股份有限公司製造之V-670進行。將吸收光譜示於[圖2]中。最大吸收波長為798 nm,莫耳吸光係數ε=1.8×104 mol-1cm-1。
於100 ml量瓶中放入1.25 g聚碳酸酯(Iupilon S-3000F(三菱工程塑膠股份有限公司製造))、12.5 mg於實施例1所得之化合物No.1、及二氯甲烷,使其充分溶解之後,稀釋至100 ml,獲得近紅外線吸收性合成樹脂組合物溶液。藉由取該溶液10 ml至培養皿中並慢慢地使其乾燥,獲得作為近紅外線吸收材料之聚碳酸酯近紅外線吸收薄膜。所得之薄膜之厚度為90 μm。又,測定所得之聚碳酸酯近紅外線吸收薄膜之吸收光譜。測定係藉由日本分光股份有限公司製造之V-670進行。將吸收光譜示於[圖3]中。所得之薄膜之最大吸收波長為814 nm,換算成化合物No.1之莫耳吸光係數ε=1.6×104 Mol-1cm-1,故而可確認該薄膜於近紅外線區域顯示出良好之吸收。
除使用聚甲基丙烯酸甲酯(PMMA)代替聚碳酸酯,並使薄膜之厚度為30 μm以外,以與實施例2同樣之方式獲得作為近紅外線吸收材料之PMMA近紅外線吸收薄膜。所得之薄膜之最大吸收波長為813 nm,換算成化合物No.1之莫耳吸光係數ε=1.6×104 Mol-1cm-1,故而可確認該薄膜於近紅外線區域顯示出良好之吸收。
依據JIS K7105測定於實施例2及3所得之近紅外線吸收薄膜之Haze值(透明性)。對除未使用化合物No.1以外以與實施例2同樣之方式製作而成之聚碳酸酯薄膜(比較例1)、及除未使用化合物No.1以外以與實施例3同樣之方式製作而成之PMMA薄膜(比較例2)亦進行測定。將測定結果示於[表1]中。
根據上述[表1]之結果,可確認本發明之硼化合物無損合成樹脂之透明性,且不影響樹脂本來之顏色。
圖1表示於實施例1合成之作為本發明之新穎硼化合物之化合物No.1之1H-NMR圖表。
圖2表示於實施例1合成之作為本發明之新穎硼化合物之化合物No.1之丙酮溶液之吸收光譜。
圖3表示於實施例2製造之作為使用本發明之近紅外線吸收性合成樹脂組合物之近紅外線吸收材料之聚碳酸酯近紅外線吸收薄膜之吸收光譜。
Claims (4)
- 一種硼化合物,其係下述通式(1)所示:
- 一種近紅外線吸收劑,其含有如請求項1之硼化合物。
- 一種近紅外線吸收性合成樹脂組合物,其含有如請求項1之硼化合物。
- 一種近紅外線吸收材料,其含有如請求項3之近紅外線吸收性合成樹脂組合物。
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