JPH0541667B2 - - Google Patents
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- Publication number
- JPH0541667B2 JPH0541667B2 JP60206614A JP20661485A JPH0541667B2 JP H0541667 B2 JPH0541667 B2 JP H0541667B2 JP 60206614 A JP60206614 A JP 60206614A JP 20661485 A JP20661485 A JP 20661485A JP H0541667 B2 JPH0541667 B2 JP H0541667B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- parts
- compound
- azo pigment
- 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.)
- Expired - Fee Related
Links
- 239000000049 pigment Substances 0.000 claims description 35
- -1 anthraquinonyl group Chemical group 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 12
- 239000012876 carrier material Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 19
- 238000007639 printing Methods 0.000 description 13
- HRNSEOMPRWUKQL-UHFFFAOYSA-N 2-hydroxy-n-(4-methoxyphenyl)-11h-benzo[a]carbazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC2=CC=C(C=3C(=CC=CC=3)N3)C3=C2C=C1O HRNSEOMPRWUKQL-UHFFFAOYSA-N 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 241001464837 Viridiplantae Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GMGDWNYWMLZUEF-UHFFFAOYSA-N 2-hydroxy-n-(4-methoxy-2-methylphenyl)-11h-benzo[a]carbazole-3-carboxamide Chemical compound CC1=CC(OC)=CC=C1NC(=O)C1=CC2=CC=C(C=3C(=CC=CC=3)N3)C3=C2C=C1O GMGDWNYWMLZUEF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000011344 liquid material Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- IDWXQRMUCRXFAK-UHFFFAOYSA-N (2-phenyldiazenylhydrazinyl)benzene Chemical compound C=1C=CC=CC=1N=NNNC1=CC=CC=C1 IDWXQRMUCRXFAK-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- XGYLSRFSXKAYCR-UHFFFAOYSA-N 2-chloro-4-methylaniline Chemical compound CC1=CC=C(N)C(Cl)=C1 XGYLSRFSXKAYCR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- VOYNKHKVVYBZQC-UHFFFAOYSA-N 2-methoxy-5-methyl-4-[(4-methyl-2-nitrophenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=C1C VOYNKHKVVYBZQC-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- WLJSUJOESWTGEX-UHFFFAOYSA-N 5-chloro-2-(4-chlorophenoxy)aniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 WLJSUJOESWTGEX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 229920002978 Vinylon Polymers 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VIUTVHGOAOMQHY-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1NC(=O)C1=CC=CC=C1 VIUTVHGOAOMQHY-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は迷彩用材料に関し、更に詳しく伝えば
森林、草原等の如き緑色植物等と同様な赤外線に
対する性質を有する性質を有する迷彩用材料に関
する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a camouflage material, and more specifically, to a camouflage material having properties similar to those of green plants such as forests, grasslands, etc. to infrared rays. .
（従来の技術）
従来、野戦偽装用として、その環境地域の物体
と錯覚を生じせしめる様な迷彩を施すことが軍事
的に広く行われている。例えば、森林や草原等で
の兵士の服装、装備、施設等は暗緑色と黒色との
ランダム模様の迷彩が施されているのが普通であ
る。(Prior Art) Hitherto, it has been widely used militarily to apply camouflage that creates the illusion of objects in the environment for field camouflage. For example, soldiers' clothing, equipment, facilities, etc. in forests, grasslands, etc. are usually decorated with dark green and black camouflage in random patterns.
（発明が解決しようとしている問題点）
しかしながら、軍事技術の向上からして、これ
らの迷彩を施しても、赤外線探知機等の使用によ
り、それらの迷彩は容易に植物から区別され探知
されてしまう欠点がある。これは従来の緑〜黒緑
色として使用されている顔料又は染料の赤外線反
射率と自然の植物の赤外線反射率とが明瞭な差が
ある為である。(Problem that the invention is trying to solve) However, as military technology improves, even if these camouflages are applied, they can be easily distinguished from plants and detected using infrared detectors, etc. There are drawbacks. This is because there is a clear difference between the infrared reflectance of pigments or dyes used in conventional green to dark green colors and the infrared reflectance of natural plants.
従つて、軍事用及びその他の迷彩用色素として
植物と同一或いは類似の赤外線に対する性質を有
する色素が要求されている。 Therefore, there is a demand for pigments for military and other camouflage purposes that have the same or similar infrared ray properties as plants.
（問題点を解決する為の手段）
本発明者は、上述の如き従来技術の要望に応え
るべく鋭意研究の結果、ある特定の構造のアゾ顔
料が、植物と殆ど同一の赤外線に対する性質を示
すことを知見し、該アゾ顔料を用いて、例えば、
着色剤、塗料或いは樹脂成形品とすることによつ
て、赤外線探知によつて緑色植物から区別し得な
い迷彩用材料が得られることを知見して本発明を
完成した。(Means for Solving the Problems) As a result of intensive research in response to the above-mentioned demands of the prior art, the present inventor has discovered that an azo pigment with a specific structure exhibits almost the same infrared ray properties as plants. and using the azo pigment, for example,
The present invention was completed based on the finding that a camouflage material that cannot be distinguished from green plants by infrared detection can be obtained by using a coloring agent, paint, or resin molding.
即ち、本発明は、下記一般式（）で表され、
結晶の大きさが0.3〜10μｍであるアゾ顔料及び担
体材料からなる迷彩用材料である。 That is, the present invention is represented by the following general formula (),
This is a camouflage material consisting of an azo pigment with a crystal size of 0.3 to 10 μm and a carrier material.
〔但し、上記式中のｎは１又は２であり、Ｘは水
素原子又はメチル基であり、ｎ＝１のとき、R1
は、ハロゲン原子、メチル基、ニトロ基、メトキ
シ基、フエノキシ基、フエニルアゾ基又はベンゾ
イルアミノ基を有してもよいフエニル基又はアン
トラキノニル基であり、ｎ＝２のときR1は、ハ
ロゲン原子、メチル基、メトキシ基、エトキシ基
又はニトロ基を有してもよいビフエニレン基であ
る。〕
本発明を更に詳細に説明すると、本発明で使用
し主として本発明を特徴づける上記一般式（）
のアゾ顔料は、下記一般式（）で表されている
化合物を、下記一般式（）で表されるカツプリ
ング成分に常法に従つてカツプリングさせる方法
によつて得られるものである。 [However, n in the above formula is 1 or 2, X is a hydrogen atom or a methyl group, and when n = 1, R 1
is a phenyl group or anthraquinonyl group which may have a halogen atom, methyl group, nitro group, methoxy group, phenoxy group, phenylazo group or benzoylamino group, and when n=2, R 1 is a halogen atom, methyl is a biphenylene group which may have a group, a methoxy group, an ethoxy group or a nitro group. ] To explain the present invention in more detail, the above general formula () used in the present invention and mainly characterizing the present invention
The azo pigment is obtained by coupling a compound represented by the following general formula () with a coupling component represented by the following general formula () according to a conventional method.
上記式中のＸ及びR1は前記と同意義である。 X and R 1 in the above formula have the same meanings as above.
上記一般式（）で表される化合物としては、
ｎ＝１のときは、アニリン、２−ニトロ−４−メ
チルアニリン、２−（4′−クロルフエノキシ）−５
−クロルアニリン、２−メチル−４−ビトロアニ
リン、２−メトキシ−４−ニトロアニリン、２−
ニトロ−４−クロルアニリン、２−メチル−４−
ニトロアニリン、２−アミノアントラキノン、２
−ニトロ−４−メトキシアニリン、２−メトキシ
−４−（2′−ニトロ−4′−メチルフエニル）アゾ
−５−メチルアニリン、２−クロル−４−（ベン
ゾイル）アミノ−５−メトキシアニリン、２，５
−ジメトキシ−４−（4′−ニトロフエニル）アゾ
アニリン等の如きアニリン又はアニリン誘導体或
いはアミノアントラキノンであり、ｎ＝２のと
き、４，4′−ジアミノ−２，2′−ジクロルジフエ
ニル、４，4′−ジアミノ−３，3′−ジクロジフエ
ニル、４，4′−ジアミノ−３，3′−ジメチルジフ
エニル、４，4′−ジアミノ−３，3′−ジメトキシ
ジフエニル、４，4′−ジアミノ−２−ニトロジフ
エニル、４，4′−ジアミノ−３−メチルジフエニ
ル、４，4′−ジアミノ−３，3′−ジエトキシジフ
エニル、４，4′−ジアミノ−３，3′−ジメチル−
６，6′−ジニトロジフエニル、４，4′−ジアミノ
−２，2′−ジクロル−５，5′−ジメトキシジフエ
ニル、４，4′−ジアミノ−２，2′5，5′−テトラク
ロルジフエニル、４，4′−ジアミノ−３，3′，
５，5′−テトラメチルジフエニル、４，4′−ジア
ミノ−オクタクロルジフエニル、４，4′−ジアミ
ノ−ジフエニル等が使用される。 As a compound represented by the above general formula (),
When n=1, aniline, 2-nitro-4-methylaniline, 2-(4'-chlorophenoxy)-5
-Chloraniline, 2-methyl-4-vitroaniline, 2-methoxy-4-nitroaniline, 2-
Nitro-4-chloroaniline, 2-methyl-4-
Nitroaniline, 2-aminoanthraquinone, 2
-Nitro-4-methoxyaniline, 2-methoxy-4-(2'-nitro-4'-methylphenyl)azo-5-methylaniline, 2-chloro-4-(benzoyl)amino-5-methoxyaniline, 2, 5
-dimethoxy-4-(4'-nitrophenyl) aniline or aniline derivatives such as azoaniline, or aminoanthraquinone, and when n=2, 4,4'-diamino-2,2'-dichlorodiphenyl, 4, 4'-Diamino-3,3'-dicrodiphenyl, 4,4'-diamino-3,3'-dimethyldiphenyl, 4,4'-diamino-3,3'-dimethoxydiphenyl, 4,4'-diamino -2-nitrodiphenyl, 4,4'-diamino-3-methyldiphenyl, 4,4'-diamino-3,3'-diethoxydiphenyl, 4,4'-diamino-3,3'-dimethyl-
6,6'-dinitrodiphenyl, 4,4'-diamino-2,2'-dichloro-5,5'-dimethoxydiphenyl, 4,4'-diamino-2,2'5,5'-tetrachlor Diphenyl, 4,4'-diamino-3,3',
5,5'-tetramethyldiphenyl, 4,4'-diamino-octachlordiphenyl, 4,4'-diamino-diphenyl, etc. are used.
次に上記一般式（）で表される芳香族アミン
をジアゾ化する方法は、従来の芳香族アミンのジ
アゾ化法をそのまま使用することが出来、例え
ば、一般式（）で表される芳香族アミンの鉱酸
塩の冷水溶液に亜硝酸ナトリウム溶液を加え冷却
下しばらく攪拌してジアゾ化し、ジアゾジニウム
塩の水溶液を得る方法や、特公昭45−18383号公
報、同46−371890号公報、同56−2102号公報、特
開昭49−120923号公報に開示の方法で行うことが
出来る。 Next, for the method of diazotizing the aromatic amine represented by the above general formula (), the conventional method for diazotizing aromatic amines can be used as is. For example, the aromatic amine represented by the general formula () A method for obtaining an aqueous solution of a diazodinium salt by adding a sodium nitrite solution to a cold aqueous solution of a mineral salt of an amine and stirring for a while under cooling to diazotize the solution; This can be carried out by the method disclosed in Japanese Patent Application Laid-Open No. 49-120923.
本発明において使用する一般式（）で表され
るカツプリング成分としては、従来公知のものが
使用でき、例えば、前記一般式（）で表される
化合物は、２−ヒドロキシ−1′，2′−ベンゾカル
バゾール−３−カルボン酸或いはその官能誘導体
と２−メトキシアニリン又は２−メトキシ−４−
メチルアニリンとを約１：１のモル比で反応させ
ることによつて得られ、ナフトールAS−SR及び
ナフトールAS−SGとして市場から入手すること
が出来る。 As the coupling component represented by the general formula () used in the present invention, conventionally known coupling components can be used. For example, the compound represented by the general formula () is 2-hydroxy-1',2'- Benzocarbazole-3-carboxylic acid or its functional derivative and 2-methoxyaniline or 2-methoxy-4-
It is obtained by reacting with methylaniline in a molar ratio of about 1:1, and is commercially available as naphthol AS-SR and naphthol AS-SG.
本発明において使用するアゾ顔料は上記一般式
（）で表される芳香族アミンのジアゾニウム塩
と一般式（）で表されるカツプリング成分と
を、従来行われているアゾ顔料の製造方法に準じ
てカツプリングすることにより得られる。 The azo pigment used in the present invention is produced by combining the diazonium salt of an aromatic amine represented by the above general formula () and the coupling component represented by the general formula () according to the conventional method for producing an azo pigment. Obtained by coupling.
即ち、上記カツプリング成分をアルカリ水溶液
に加えて加熱溶解させ、次いでその溶液を25℃近
くに冷却し、これに緩衝剤を加え、更にPHを調整
し、しかる後これに上記一般式（）で表される
芳香族アミンのジアゾニウム塩水溶液を滴下して
アルカリ性にて常温にてカツプリング反応を行
い、粗アゾ顔料を生成し、次いで濾過、水洗し乾
燥して目的とするアゾ顔料を得る。更に本発明に
おいて有機溶媒中においてもカツプリング反応を
行うことが出来る。 That is, the above coupling component is added to an alkaline aqueous solution and dissolved by heating, then the solution is cooled to around 25°C, a buffer is added thereto, the pH is adjusted, and then the solution expressed by the above general formula () is added. An aqueous solution of a diazonium salt of an aromatic amine is added dropwise to perform a coupling reaction in an alkaline environment at room temperature to produce a crude azo pigment, which is then filtered, washed with water, and dried to obtain the desired azo pigment. Furthermore, in the present invention, the coupling reaction can also be carried out in an organic solvent.
本発明者の詳細な研究によれば、上記のアゾ顔
料はその結晶の大きさが、0.3〜10μｍであるとき
に最も優れた赤外線反射性を示すことを知見し
た。 According to detailed research conducted by the present inventors, it has been found that the above-mentioned azo pigment exhibits the best infrared reflectivity when the crystal size thereof is 0.3 to 10 μm.
上記の如くして製造された本発明方法で使用す
るアゾ顔料は、暗色〜黒色であり、耐溶剤性、耐
光性、耐熱性、耐水性、耐薬品性も良好であり着
色力が高くアゾ顔料として充分使用され得る。 The azo pigment used in the method of the present invention produced as described above is dark to black in color, has good solvent resistance, light resistance, heat resistance, water resistance, and chemical resistance, and has high coloring power. It can be fully used as
本発明の迷彩用材料は、上記のアゾ顔料と担体
材料からなるものである。ここに本発明における
担体材料とは、従来、顔料捺染、印刷インキ、塗
料等において使用されているバインダー樹脂を云
い、又、合成繊維、例えば、アセチルセルロー
ス、ビニロン、ポリエステル、ポリアミド、ポリ
プロピレン等を前記アゾ顔料で原液着色する場合
には、これらの合成繊維も本発明の担体材料に包
含されるものである。更に前記のアゾ顔料を用い
て、上記の如き合成樹脂、その他ポリエチレン、
ポリプロピレン、ポリスチレン、ポリ塩化ビニ
ル、ポリカーボネート、ポリイミド、フエノール
樹脂、尿素樹脂、メラニン樹脂等の熱可塑性或い
は熱硬化性樹脂を着色して、フイルム、シートそ
の他の各種着色成形品を得る場合にはこれらの熱
可塑性及び熱硬化性の合成樹脂も本発明における
担体材料に包含されるものである。 The camouflage material of the present invention consists of the above-mentioned azo pigment and carrier material. The carrier material in the present invention refers to binder resins conventionally used in pigment textile printing, printing inks, paints, etc., and synthetic fibers such as acetylcellulose, vinylon, polyester, polyamide, polypropylene, etc. When coloring with an azo pigment as a stock solution, these synthetic fibers are also included in the carrier material of the present invention. Furthermore, using the azo pigment described above, synthetic resins such as those described above, other polyethylene,
When coloring thermoplastic or thermosetting resins such as polypropylene, polystyrene, polyvinyl chloride, polycarbonate, polyimide, phenolic resin, urea resin, melanin resin, etc., to obtain various colored molded products such as films, sheets, etc. Thermoplastic and thermosetting synthetic resins are also included as carrier materials in the present invention.
従つて、本発明の迷彩用材料の１例は、従来の
顔料捺染剤、印刷インキ、塗料等の液状材料にお
ける従来の顔料に代えて前記一般式（）のアゾ
顔料を用いたものに相当し、これらの例において
は従来技術におけると同様に、液状材料100重量
部で、前記一般式（）のアゾ顔料を約0.1〜50
重量部の割合で用いているのが一般的である。
又、担体材料は１〜30重量部、そして媒体は10〜
95重量部の割合で用いるのが一般的である。 Therefore, one example of the camouflage material of the present invention corresponds to one in which the azo pigment of the general formula () is used in place of the conventional pigment in liquid materials such as conventional pigment printing agents, printing inks, and paints. In these examples, as in the prior art, 100 parts by weight of the liquid material contains about 0.1 to 50 parts of the azo pigment of the general formula ().
It is generally used in parts by weight.
Also, the carrier material is 1 to 30 parts by weight, and the medium is 10 to 30 parts by weight.
It is generally used in a proportion of 95 parts by weight.
又、別の１例である着色合成繊維或いは着色樹
脂成形品においては、前記一般式（）のアゾ顔
料はそれらの繊維や成形品を実質的に着色出来る
程度、例えば、0.1〜30重量％の割合で包含され
るのが一般的である。 Furthermore, in the case of colored synthetic fibers or colored resin molded articles, which is another example, the azo pigment of the general formula () is used in an amount that can substantially color the fibers or molded articles, for example, 0.1 to 30% by weight. Generally, it is included by percentage.
以上の如き本発明の迷彩用材料は、上記の如き
液状材料であつても、又、上記の如き着色繊維又
は樹脂成形品であつても、いずれも従来公知の顔
料捺染剤、塗料、印刷インキの製造方法或いは原
液着色方法、合成樹脂の着色成形方法と同様な方
法で得ることが出来る。 The camouflage material of the present invention as described above may be a liquid material as described above, a colored fiber or resin molded product as described above, and any of the above-mentioned pigment printing agents, paints, and printing inks can be used. It can be obtained by a method similar to the manufacturing method, the method of coloring a stock solution, or the method of coloring and molding synthetic resins.
（作用・効果）
以上の如き本発明の迷彩用材料は、従来の顔料
捺染剤、塗料、印刷インキと同様に使用出来、織
布、不織布の捺染、各種物品の塗料、及び印刷に
有用であり、暗緑色〜黒色の彩色を与え、これら
の着色物品の赤外線に対する性質を天然の緑色植
物と同様な赤外線に対する性質とすることが出来
る。(Action/Effect) The camouflage material of the present invention as described above can be used in the same way as conventional pigment printing agents, paints, and printing inks, and is useful for printing woven fabrics and nonwoven fabrics, coatings for various articles, and printing. , giving a dark green to black coloring, and making these colored articles have infrared ray properties similar to those of natural green plants.
又、本発明の迷彩用材料が着色繊維や成形品で
ある場合にも同様であり、緑色動物と同様な赤外
線に対する性質を有する繊維や、成形品を与え
る。 The same applies when the camouflage material of the present invention is colored fibers or molded articles, and fibers or molded articles having properties against infrared rays similar to those of green animals are provided.
従つて、本発明の迷彩用材料により、軍事用の
各種装備、装置及び施設に迷彩を施すことによつ
て、赤外線探知機によつて環境雰囲気である緑色
植物から、探知されない迷彩を施すことが出来
る。 Therefore, by applying camouflage to various military equipment, equipment, and facilities using the camouflage material of the present invention, it is possible to apply camouflage that will not be detected by infrared detectors from green plants in the environment. I can do it.
次に実施例を挙げて本発明を更に具体的に説明
する。尚、文中、部又は％とあるのは特に断りの
ない限り重量基準である。 Next, the present invention will be explained in more detail with reference to Examples. In the text, parts or percentages are based on weight unless otherwise specified.
実施例 １
0.01モルの２−クロル−４−メチルアニリン
を、氷酢酸11.3部に懸濁し、これに濃塩酸3.7部
を加えて攪拌した。これに水2.6部を加え温度０
〜５℃に保ち、40％亜硝酸ナトリウム水溶液2.0
部を加え、約30分間同温度にて攪拌して黄色のジ
アゾニウム塩の溶液を得た。これに酢酸ナトリウ
ム３水和物4.8部を加えてジアゾニウム塩の溶液
を調製した。Example 1 0.01 mol of 2-chloro-4-methylaniline was suspended in 11.3 parts of glacial acetic acid, and 3.7 parts of concentrated hydrochloric acid was added thereto and stirred. Add 2.6 parts of water to this and the temperature is 0.
Keep at ~5℃, 40% sodium nitrite aqueous solution 2.0
of the solution and stirred at the same temperature for about 30 minutes to obtain a yellow diazonium salt solution. 4.8 parts of sodium acetate trihydrate was added to this to prepare a diazonium salt solution.
一方、ナフトールAS−SG0.01モルをｏ−ジク
ロルベンゼン250部中に懸濁させ、20〜30℃で上
記ジアゾニウム塩溶液を加え、30〜40に保ち氷酢
酸20部を加えた。この温度で５〜６時間保ちカツ
プリングを行い、下記式のアゾ顔料が得られた。
該アゾ顔料は黒色を呈する。 Separately, 0.01 mole of naphthol AS-SG was suspended in 250 parts of o-dichlorobenzene, the above diazonium salt solution was added at 20 to 30°C, the temperature was maintained at 30 to 40°C, and 20 parts of glacial acetic acid was added. The mixture was maintained at this temperature for 5 to 6 hours and coupled to obtain an azo pigment of the following formula.
The azo pigment exhibits a black color.
実施例 ２
0.01モルのジアニシジンをジメチルホルムアミ
ド45部に溶解させ、０℃に冷却する。この中に
0.06モルの塩酸を滴下し、60分間かき混ぜて塩酸
塩とし、更に0.02モルの亜硝酸ソーダを４部の水
に溶解したものを滴下して60分間ジアゾ化を行
う。 Example 2 0.01 mol of dianisidine is dissolved in 45 parts of dimethylformamide and cooled to 0°C. in this
0.06 mol of hydrochloric acid is added dropwise and stirred for 60 minutes to form a hydrochloride salt. Furthermore, 0.02 mol of sodium nitrite dissolved in 4 parts of water is added dropwise to carry out diazotization for 60 minutes.
一方、ナフトールAS−SG0.02モルをジメチル
ホルムアミド60部に溶解させ、酢酸ソーダ0.09モ
ルをメタノール24.5部に溶解させ、上記溶液に添
加する。この下漬液をかきまぜながら、20〜30℃
で上記のジアゾニウム溶液をゆつくりと滴下し
て、20〜30℃で２時間カツプリング反応を行つ
て、下記式で表される黒色のアゾ顔料を得た。 On the other hand, 0.02 mol of naphthol AS-SG is dissolved in 60 parts of dimethylformamide, and 0.09 mol of sodium acetate is dissolved in 24.5 parts of methanol, and these are added to the above solution. While stirring this subsoaking liquid, heat it at 20-30℃.
The above diazonium solution was slowly added dropwise, and a coupling reaction was carried out at 20 to 30°C for 2 hours to obtain a black azo pigment represented by the following formula.
実施例 ３〜14
実施例１又は実施例２と同様な方法で下記の一
般式（）の化合物及び一般式（）の化合物を
用いて夫々構造式で表される本発明で使用するア
ゾ顔料を得た。 Examples 3 to 14 In the same manner as in Example 1 or Example 2, the azo pigments used in the present invention represented by the structural formulas are prepared using the following compounds of the general formula () and the compound of the general formula (), respectively. Obtained.
実施例 ３
一般式（）の化合物；２−（4′−クロルフエノ
キシ）−５−クロルアニリン
一般式（）の化合物；ナフトールAS−SR
色調；やや赤味の黒色
実施例 ４
一般式（）の化合物；２−メチル−４−ニトロ
アニリン
一般式（）の化合物；ナフトールAS−SR
色調；黒色
実施例 ５
一般式（）の化合物；２−メトキシ−４−ニト
ロアニリン
一般式（）の化合物；ナフトールAS−SR
色調；黒色
実施例 ６
一般式（）の化合物；２−ニトロ−４−メチル
アニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや青色の黒色
実施例 ７
一般式（）の化合物；２−メチル−４−クロア
ニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや緑色の黒色
実施例 ８
一般式（）の化合物；２−メチル−４−ニトロ
エアニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや赤味の黒色
実施例 ９
一般式（）の化合物；２−メトキシ−４−ニト
ロアニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや緑色の黒色
実施例 10
一般式（）の化合物；１−アミノアントラキノ
ン
一般式（）の化合物；ナフトールAS−SG
色調；やや赤味の黒色
実施例 11
一般式（）の化合物；２−ニトロ−４−メトキ
シアニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや青味の黒色
実施例 12
一般式（）の化合物；２−メトキシ−４−
（2′−ニトロ−4′−メチルフエニル）−アゾ−５
−メチルアニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや緑味の黒色
実施例 13
一般式（）の化合物；２−クロル−４−ベンゾ
イルアミノ−５−メトキシアニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや緑味の黒色
実施例 14
一般式（）の化合物；２，５−ジメトキシ−４
−（4′−ニトロフエニル）−アゾ−アニリン
一般式（）の化合物；ナフトールAS−SG
色調；やや緑味の黒色
実施例 15
アクリル酸エステルエマルジヨン（活性剤フリー
タイプ、固形分40％） 30部
実施例１で得られたアゾ顔料 35部
消泡剤 0.5部
分散剤 １部
Daimonex EX−６（大日精化製） ３部
ターペン 15部
メタノール ８部水 15.5部
合計 100部
上記処方にてアゾ顔料を分散させた糊状の黒色
ペーストに、エチレンイミン系の架橋剤を１％併
用し、エントランス（東レ系）布上にシルクスク
リーンにてプリントし、120℃で15分間のキユア
ーを行うことにより、黒色のプリント物が得られ
る。このプリント物のプリント部分の赤外線反射
率を測定したところ、第１図に示す如く、カーボ
ンブラツク顔料による同物品の赤外線反射率より
も著しく反射率が高かつた。Example 3 Compound of general formula (); 2-(4'-chlorophenoxy)-5-chloroaniline Compound of general formula (); Naphthol AS-SR Color tone: Slightly reddish black Example 4 Compound of general formula (); 2-methyl-4-nitroaniline Compound of general formula (); Naphthol AS-SR Color tone: black Example 5 Compound of general formula (); 2-methoxy-4-nitroaniline Compound of general formula (); Naphthol AS-SR Color tone: Black Example 6 Compound of general formula (); 2-nitro-4-methylaniline Compound of general formula (); Naphthol AS-SG Color tone: slightly blue black Example 7 Compound of general formula (); 2-methyl-4-chloraniline Compound of general formula (); Naphthol AS-SG Color tone: slightly greenish black Example 8 Compound of general formula (); 2-methyl-4-nitroeaniline Compound of general formula (); Naphthol AS-SG Color tone: Slightly reddish black Example 9 Compound of general formula (); 2-methoxy-4-nitroaniline Compound of general formula (); Naphthol AS-SG Color tone: slightly greenish black Example 10 Compound of general formula (); 1-aminoanthraquinone Compound of general formula (); Naphthol AS-SG Color tone: Slightly reddish black Example 11 Compound of general formula (); 2-nitro-4-methoxyaniline Compound of general formula (); Naphthol AS-SG Color tone: Slightly bluish black Example 12 Compound of general formula (); 2-methoxy-4-
(2'-nitro-4'-methylphenyl)-azo-5
-Methylaniline Compound of general formula (); Naphthol AS-SG Color tone: slightly greenish black Example 13 Compound of general formula (); 2-chloro-4-benzoylamino-5-methoxyaniline Compound of general formula (); Naphthol AS-SG Color tone: slightly greenish black Example 14 Compound of general formula (); 2,5-dimethoxy-4
-(4′-nitrophenyl)-azo-aniline Compound of general formula (); Naphthol AS-SG Color tone: Black with a slight greenish tinge Example 15 Acrylic acid ester emulsion (activator-free type, solid content 40%) 30 parts Azo pigment obtained in Example 1 35 parts Antifoaming agent 0.5 parts Powder 1 part Daimonex EX-6 (manufactured by Dainichiseika) 3 parts turpentine 15 parts methanol 8 parts water 15.5 parts total 100 parts A paste-like black paste with azo pigment dispersed in the above formulation was combined with 1% ethyleneimine crosslinking agent, and was coated on Entrance (Toray brand) cloth. A black print can be obtained by printing with a silk screen and curing at 120℃ for 15 minutes. When the infrared reflectance of the printed portion of this printed article was measured, as shown in FIG. 1, it was found to be significantly higher than the infrared reflectance of the same article made of carbon black pigment.
実施例 16
実施例２で得られたアゾ顔料 17部
熱可塑性アクリル樹脂 70部
トルオール 6.8
キシロール 3.2部
ブタノール 2.2部セロソルブ 0.8部
合計 100部
上記組成物をボールミルで分散処理して黒色の
塗料とした。これを、鋼板に塗布して塗膜を形成
し、該塗膜の赤外線反射率を測定したところ、実
施例15と同様な結果が得られた。Example 16 Azo pigment obtained in Example 2 17 parts Thermoplastic acrylic resin 70 parts Toluene 6.8 parts Xylol 3.2 parts Butanol 2.2 parts Cellosolve 0.8 parts Total 100 parts The above composition was dispersed in a ball mill to obtain a black paint. When this was applied to a steel plate to form a coating film and the infrared reflectance of the coating film was measured, the same results as in Example 15 were obtained.
実施例 17
実施例３で得たアゾ顔料のフラツシドカラー
（純分50％） 38.0部
オフセツト平版インキ用調合ワニス 60.0部
５％コバルトドライヤー 0.2部
８％マンガンドライヤー 1.0部インキソルベルト 0.8部
合計 100部
上記成分を十分に混合練内してオフセツト印刷
インキを得た。この印刷インキにて上質紙にベタ
印刷し、その赤外線反射率を測定したところ、実
施例15と同様な結果を得た。Example 17 Fluid color of the azo pigment obtained in Example 3 (purity 50%) 38.0 parts Mixed varnish for offset lithographic ink 60.0 parts 5% Cobalt dryer 0.2 parts 8% Manganese dryer 1.0 parts Inksol belt 0.8 parts Total 100 Part The above components were sufficiently mixed and kneaded to obtain an offset printing ink. When solid printing was performed on high-quality paper using this printing ink and the infrared reflectance thereof was measured, the same results as in Example 15 were obtained.
実施例 18
実施例４で得たアゾ顔料0.5部とパンソルブ
H1.0部とを混練したものをポリ塩化ビニル樹脂
コンパウンド50部と混合し、６インチロールで
155〜160℃で３分間ロール練りしてシートを形成
し、このシートを170℃で50Kgの圧力で厚さ５mm
にプレス成形して黒緑色の着色シートを得た。こ
のシートの赤外線反射率を測定しところ実施例15
と同様な結果を得た。Example 18 0.5 part of azo pigment obtained in Example 4 and Pansolve
Mix 1.0 part of H with 50 parts of polyvinyl chloride resin compound and roll it into a 6-inch roll.
Form a sheet by roll kneading at 155-160℃ for 3 minutes, and roll this sheet to a thickness of 5mm at 170℃ with a pressure of 50Kg.
A black-green colored sheet was obtained by press molding. Example 15 The infrared reflectance of this sheet was measured.
obtained similar results.
尚、実施例６〜14で得られたアゾ顔料を用いて
いずれも実施例15〜18と同様に着色したものは、
優れた赤外線反射率を示した。 In addition, those colored in the same manner as Examples 15 to 18 using the azo pigments obtained in Examples 6 to 14,
It showed excellent infrared reflectance.
第１図は、天然の緑色植物の赤外線反射率曲線
（破線）と、実施例12で得られた迷彩用材料の赤
外線反射率曲線（実線）を示す。
FIG. 1 shows the infrared reflectance curve (dashed line) of a natural green plant and the infrared reflectance curve (solid line) of the camouflage material obtained in Example 12.
Claims (1)
0.3〜10μｍであるアゾ顔料及び担体材料からなる
迷彩用材料。 〔但し、上記式中のｎは１又は２であり、Ｘは水
素原子又はメチル基であり、ｎ＝１のとき、R1
は、ハロゲン原子、メチル基、ニトロ基、メトキ
シ基、フエノキシ基、フエニルアゾ基又はベンゾ
イルアミノ基を有してもよいフエニル基又はアン
トラキノニル基であり、ｎ＝２のときR1は、ハ
ロゲン原子、メチル基、メトキシ基、エトキシ基
又はニトロ基を有してもよいビフエニレン基であ
る。〕[Claims] 1. It is represented by the following general formula (), and the size of the crystal is
A camouflage material comprising an azo pigment having a diameter of 0.3 to 10 μm and a carrier material. [However, n in the above formula is 1 or 2, X is a hydrogen atom or a methyl group, and when n = 1, R 1
is a phenyl group or anthraquinonyl group which may have a halogen atom, methyl group, nitro group, methoxy group, phenoxy group, phenylazo group or benzoylamino group, and when n=2, R 1 is a halogen atom, methyl is a biphenylene group which may have a group, a methoxy group, an ethoxy group or a nitro group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20661485A JPS6268856A (en) | 1985-09-20 | 1985-09-20 | Camouflaging material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20661485A JPS6268856A (en) | 1985-09-20 | 1985-09-20 | Camouflaging material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6268856A JPS6268856A (en) | 1987-03-28 |
| JPH0541667B2 true JPH0541667B2 (en) | 1993-06-24 |
Family
ID=16526291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20661485A Granted JPS6268856A (en) | 1985-09-20 | 1985-09-20 | Camouflaging material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6268856A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103282443B (en) * | 2010-12-28 | 2015-01-07 | 大日精化工业株式会社 | Black azo pigment and process for production thereof, colored composition, coloring method, and colored articles |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700397A (en) * | 1969-05-06 | 1972-10-24 | Us Army | Camouflaged article and method of producing same |
| US4123270A (en) * | 1975-09-15 | 1978-10-31 | International Business Machines Corporation | Method of making electrophotographic imaging element |
| JPS59128545A (en) * | 1983-01-13 | 1984-07-24 | Ricoh Co Ltd | Electrophotographic sensitive body |
| JPS60146250A (en) * | 1984-01-10 | 1985-08-01 | Dainippon Ink & Chem Inc | Electrophotographic sensitive body |
-
1985
- 1985-09-20 JP JP20661485A patent/JPS6268856A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700397A (en) * | 1969-05-06 | 1972-10-24 | Us Army | Camouflaged article and method of producing same |
| US4123270A (en) * | 1975-09-15 | 1978-10-31 | International Business Machines Corporation | Method of making electrophotographic imaging element |
| JPS59128545A (en) * | 1983-01-13 | 1984-07-24 | Ricoh Co Ltd | Electrophotographic sensitive body |
| JPS60146250A (en) * | 1984-01-10 | 1985-08-01 | Dainippon Ink & Chem Inc | Electrophotographic sensitive body |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6268856A (en) | 1987-03-28 |
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|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |