JPH0426348B2 - - Google Patents
Info
- Publication number
- JPH0426348B2 JPH0426348B2 JP20661185A JP20661185A JPH0426348B2 JP H0426348 B2 JPH0426348 B2 JP H0426348B2 JP 20661185 A JP20661185 A JP 20661185A JP 20661185 A JP20661185 A JP 20661185A JP H0426348 B2 JPH0426348 B2 JP H0426348B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- black
- parts
- azo pigment
- group
- 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 - Lifetime
Links
- 239000000049 pigment Substances 0.000 claims description 40
- 239000000463 material Substances 0.000 claims description 18
- 239000012876 carrier material Substances 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 238000007639 printing Methods 0.000 description 13
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000012954 diazonium Substances 0.000 description 9
- 150000001989 diazonium salts Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000976 ink Substances 0.000 description 8
- 150000003931 anilides Chemical class 0.000 description 7
- 238000005859 coupling reaction Methods 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
- -1 2,5-dimethoxy-4(4'-nitrophenyl)azoaniline Chemical compound 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 239000000203 mixture 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
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- 230000005855 radiation Effects 0.000 description 3
- 238000002310 reflectometry 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
- 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 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 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 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 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
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- MSCMTURKIQRYPE-UHFFFAOYSA-N 2-hydroxyanthracene-1-carboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=C(O)C=CC3=CC2=C1 MSCMTURKIQRYPE-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
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-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
- 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
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001412 amines 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
- 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
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000017525 heat dissipation Effects 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
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-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
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline 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
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 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
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は赤外線反射性材料に関し、更に詳しく
云えば、従来のカーボンブラツクやアニリンブラ
ツク等の如き黒色顔料による着色物に比してより
高い赤外線反射性を有する赤外線反射性材料に関
する。Detailed Description of the Invention (Industrial Field of Application) The present invention relates to an infrared reflective material, and more specifically, the present invention relates to an infrared reflective material that has higher infrared rays than conventional colored materials using black pigments such as carbon black and aniline black. The present invention relates to an infrared reflective material having reflective properties.
（従来の技術及び発明が解決しようとしている問
題点）
従来、カーボンブラツク等の黒色顔料により
種々の物品が黒色に着色されているが、これらの
黒色着色物は、熱、即ち赤外線を吸収し易く、直
射日光等により異常に高温になり易いという問題
点がある。(Prior art and problems to be solved by the invention) Conventionally, various articles have been colored black with black pigments such as carbon black, but these black colored products tend to absorb heat, that is, infrared rays. However, there is a problem in that it tends to become extremely hot due to direct sunlight.
又、この様な黒色着色材料等を保温材に用いる
と赤外線放射による放熱が大で十分な保温を達成
出来ないという問題がある。 Furthermore, if such a black-colored material is used as a heat insulating material, there is a problem that heat radiation due to infrared radiation is large and sufficient heat retention cannot be achieved.
従つて、黒色に十分に着色しても赤外線を吸収
せずに反射する黒色材料が要望されている。 Therefore, there is a need for a black material that reflects infrared rays without absorbing them even when sufficiently colored black.
（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
料がある特定の粒子径範囲において、従来のカー
ボンブラツク顔料に比して著しく高い赤外線反射
性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、優れた赤外線反射性を有する赤外線反
射性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 demands of the prior art as described above, the present inventor has discovered that an azo pigment with a certain structure can be used in conventional carbon black in a certain particle size range. It has been discovered that the azo pigment exhibits significantly higher infrared reflectivity than pigments, and by using the azo pigment to make, for example, colorants, paints, or resin molded products, it is possible to create infrared reflectors with excellent infrared reflectivity. The present invention was completed by discovering that a flexible material can be obtained.
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
体材料からなる赤外線反射性材料である。 That is, the present invention is represented by the following general formula (),
It is an infrared reflective 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Ｘは、Ｎ＝Ｎ又はCONHで
あり、ｎは１又は２であり、R1は水素原子又は
ニトロ基であり、R2は、ハロゲン原子又はメト
キシ基であり、Ａ環はベンゼン環又はナフタレン
環であり、ｎ＝１のときのR3は、ハロゲン原子、
メチル基、ニトロ基又はメトキシ基を有してもよ
いフエニル基又は置換基を有していないナフチル
基であり、ｎ＝２のときR3は、メトキシ基を有
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, X in the above formula is N=N or CONH, n is 1 or 2, R 1 is a hydrogen atom or a nitro group, R 2 is a halogen atom or a methoxy group, and A The ring is a benzene ring or a naphthalene ring, and when n=1, R 3 is a halogen atom,
A phenyl group that may have a methyl group, a nitro group, or a methoxy group, or a naphthyl group that does not have a substituent, and when n=2, R 3 is a biphenylene group that may have a methoxy 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、ｎ、R1、R2、R3及びＡ環は前
記と同意義である。 In the above formula, X, n, R 1 , R 2 , R 3 and ring A have the same meanings as above.
上記一般式（）で表される化合物としては、
２−クロル−４−ベンゾイルアミノ−５−メトキ
シアニリン又は２，５−ジメトキシ−４（4′−ニ
トロフエニル）アゾアニリン（ブラツクＫベー
ス）が挙げられる。 As a compound represented by the above general formula (),
Mention may be made of 2-chloro-4-benzoylamino-5-methoxyaniline or 2,5-dimethoxy-4(4'-nitrophenyl)azoaniline (Black K base).
又、ｎ＝１のときの一般式（）で表される化
合物は、２−ヒドロキシ−３−ナフトエ酸又は２
−ヒドロキシアントラセン３−カルボン酸と芳香
族第１級アミン、例えば、アニリン、２−メチル
アニリン、２−メチル−４−メトキシアニリン、
２−メトキシアニリン、４−クロルアニリン、２
−メチル−４−クロルアニリン、３−ニトロアニ
リン、α−ナフチルアミン又はβ−ナフチルアミ
ンと反応させて得られるものであり、又、ｎ＝２
のときの一般式（）で表される化合物は、２−
ヒドロキシ−３−ナフトエ酸又は２−ヒドロキシ
アントラセンカルボン酸とジアミノジユフエニ
ル、例えば、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
ロルジフエニル、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−ジフエニル等とを２：１のモ
ル比で反応させて得られるものである。 Further, when n=1, the compound represented by the general formula () is 2-hydroxy-3-naphthoic acid or 2-hydroxy-3-naphthoic acid.
-hydroxyanthracene 3-carboxylic acid and aromatic primary amines, such as aniline, 2-methylaniline, 2-methyl-4-methoxyaniline,
2-methoxyaniline, 4-chloroaniline, 2
- It is obtained by reacting with methyl-4-chloroaniline, 3-nitroaniline, α-naphthylamine or β-naphthylamine, and n = 2
The compound represented by the general formula () when 2-
Hydroxy-3-naphthoic acid or 2-hydroxyanthracenecarboxylic acid and diaminodiufenyl, for example 4,4'-diamino-2,2'-dichlorodiphenyl, 4,4'-diamino-3,3'- Dichlordiphenyl, 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'-tetrachlordiphenyl, 4,4'-diamino-3,3',5,5'-tetramethyldiphenyl,
4,4'-diamino-octachlordiphenyl,
It is obtained by reacting with 4,4'-diamino-diphenyl etc. in a molar ratio of 2:1.
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46−37189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 acid salt of an amine and stirring for a while under cooling to diazotize the solution, as well as Japanese Patent Publications No. 18383/1983, No. 37189/1989, and No. 56 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, making it suitable as an azo pigment. It can be fully used.
本発明の赤外線反射性材料は、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。従つて、本
発明の赤外線反射性材料の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。 The infrared reflective material of the present invention consists of the above 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 acetyl cellulose, vinylon, polyester, polyamide,
In the case of coloring polypropylene or the like with the above-mentioned azo pigment, these synthetic fibers are also included in the carrier material of the present invention. Furthermore, the azo pigment described above can be used to color synthetic resins such as those described above, and other thermoplastic or thermosetting resins such as polyethylene, polypropylene, polystyrene, polyvinyl chloride, polycarbonate, polyimide, phenolic resin, urea resin, melanin resin, etc. When producing various colored molded products such as films, sheets, etc., these thermoplastic and thermosetting synthetic resins are also included in the carrier material in the present invention. Therefore, one example of the infrared reflective material of the present invention corresponds to a material using the azo pigment of the general formula () in place of the conventional pigment in liquid materials such as conventional pigment printing agents, printing inks, and paints. However, in these examples, as in the prior art, 100 parts by weight of the liquid material,
Generally, the azo pigment of the general formula () is used in an amount of about 0.1 to 50 parts by weight. Generally, the carrier material is used in an amount of 1 to 30 parts by weight, and the medium is used in an amount of 10 to 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％の割合で包含させ
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 added to an amount that can substantially color the fibers or molded articles, for example, 0.1 to 30% by weight. It is common to include them in proportions.
以上の如き本発明の赤外線反射性材料は、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 infrared reflective material of the present invention as described above may be a liquid material as described above, a colored fiber or a resin molded product as described above, and any of the above-mentioned pigment printing agents, paints, printing materials, etc. It can be obtained by a method similar to an ink manufacturing method, a undiluted solution coloring method, or a synthetic resin coloring molding method.
（作用・効果）
以上の如き本発明の赤外線反射性材料は、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、暗色〜黒色の彩色を与え、こ
れらの着色物品の赤外線反射率は、従来のカーボ
ンブラツク顔料を用いた着色物に比して著しく高
い値を示す。(Action/Effect) The infrared reflective 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. The infrared reflectance of these colored articles is significantly higher than that of colored articles using conventional carbon black pigments.
又、本発明の赤外線反射性材料が着色繊維や成
形品である場合にも同様であり、同様な赤外線反
射性を有する繊維や成形品を与える。 The same applies when the infrared reflective material of the present invention is colored fibers or molded articles, and fibers or molded articles having similar infrared reflective properties can be obtained.
従つて、本発明の赤外線反射性材料により、各
種の物品を得ることによつて、黒色でありながら
赤外線を吸収せず、直射日光等によつて過度には
昇温しない物品を得ることが出来、又、これらの
物品を保温材に使用すれば、内容物の赤外線放射
による放熱を抑制することが出来る。 Therefore, by obtaining various articles using the infrared reflective material of the present invention, it is possible to obtain articles that are black but do not absorb infrared rays and do not excessively increase in temperature due to direct sunlight, etc. Moreover, if these articles are used as a heat insulating material, it is possible to suppress heat dissipation due to infrared radiation of the contents.
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−ベンゾイルアミノ
−５−メトキシアニリンを、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-benzoylamino-5-methoxyaniline was suspended in 11.3 parts of glacial acetic acid, and 3.7 parts of concentrated hydrochloric acid was added thereto and stirred. To this was added 2.6 parts of water, the temperature was maintained at 0 to 5°C, 2.0 parts of a 40% aqueous sodium nitrite solution was added, and the mixture was 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、２−ヒドロキシ−３−カルボ（2′−メチ
ルアニライド）アントラセン0.01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を有する。 Separately, 0.01 mole of 2-hydroxy-3-carbo(2'-methylanilide) anthracene was suspended in 250 parts of o-dichlorobenzene, and the above diazonium salt solution was added at 20 to 30°C. Added 20 parts of glacial acetic acid. 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 has a black appearance.
実施例 ２
0.01モルのブラツクＫベースを、氷酢酸、11.3
部に懸濁し、これに農塩酸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 2 0.01 mole of Black K base was dissolved in glacial acetic acid, 11.3
3.7 parts of agricultural hydrochloric acid was added and stirred. Add 2.6 parts of water to this and keep the temperature at 0-5℃.
Add 2.0 parts of 40% sodium nitrite aqueous solution, approx.
The mixture was stirred for a minute at the same temperature to obtain a yellow diazonium salt solution. In this, sodium acetate trihydrate 4.8
of the diazonium salt was added to prepare a solution of the diazonium salt.
一方、２−ヒドロキシ−３−ナフトエ酸（2′−
メチル−4′−メトキシ）アニライド0.01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を有する。 On the other hand, 2-hydroxy-3-naphthoic acid (2'-
0.01 mol of methyl-4'-methoxy)anilide
- suspended in 250 parts of dichlorobenzene,
The above diazonium salt solution was added at 30°C 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 has a black appearance.
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；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（2′−メトキシ）アニライド
色 調；やや青味の黒色
実施例 ４
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸アニライド
色 調；やや青味の黒色
実施例 ５
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（4′−クロル）アニライド
色 調；やや青味の黒色
実施例 ６
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（2′−メチル）アニライド
色 調；やや青味の黒色
実施例 ７
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（2′，4′−ジクロル）アニライド
色 調；やや青味の黒色
実施例 ８
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（2′，4′5′−トリクロロ）アニライド
色 調；やや青味の黒色
実施例 ９
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸（3′−ニトロ）アニライド
色 調；やや青味の黒色
実施例 10
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸βナフチルアミド
色 調；やや青味の黒色
実施例 11
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；２−ヒドロキシ−３−ナ
フトエ酸αナフチルアミド
色 調；やや青味の黒色
実施例 12
一般式（）の化合物；ブラツクＫベース
一般式（）の化合物；４，4′−ビス（2′−ヒド
ロキシ−３−ナフトエ酸アミド）−３，3′−ジ
メトキシジユフエニル
色 調；やや赤味の黒色
実施例 13
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、エチレンイミド系の架橋剤を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 (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (2'-methoxy) anilide Color tone: slightly bluish black Example 4 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid anilide Color tone: slightly bluish black Example 5 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (4'-chloro) anilide Color tone: slightly bluish black Example 6 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (2'-methyl) anilide Color tone: slightly bluish black Example 7 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (2',4'-dichloro)anilide Color tone: Slightly bluish black Example 8 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (2',4'5'-trichloro)anilide Color tone: Slightly bluish black Example 9 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid (3'-nitro)anilide Color tone: slightly bluish black Example 10 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid β-naphthylamide Color tone: slightly bluish black Example 11 Compound of general formula (); Black K base Compound of general formula (); 2-hydroxy-3-naphthoic acid α-naphthylamide Color tone: slightly bluish black Example 12 Compound of general formula (); Black K base Compound of general formula (); 4,4'-bis(2'-hydroxy-3-naphthoic acid amide)-3,3'-dimethoxydiyphenyl color tone ;Slightly reddish black Example 13 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 glue-like black paste with azo pigment dispersed in the above recipe was combined with 1% ethyleneimide crosslinking agent to create an entrance (Toray brand) cloth. A black print is obtained by printing with a silk screen and curing at 120°C 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 14
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13と同様な結果が得られた。Example 14 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 13 were obtained.
実施例 15
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部インキソルベント 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13と同様な結果を得た。Example 15 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 Ink solvent 0.8 parts Total 100 Part The above components were thoroughly 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 13 were obtained.
実施例 16
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たところ実施例
13と同様な結果を得た。Example 16 0.5 part of the 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 of measuring the infrared reflectance of this sheet
13 obtained similar results.
尚、実施例６〜12で得られたアゾ顔料を用いて
いずれも実施例13〜16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 13 to 16 using the azo pigments obtained in Examples 6 to 12,
It showed excellent infrared reflectance.
第１図は、カーボンブラツクによる着色物の赤
外線反射率曲線（破線）と、実施例13で得られた
赤外線反射性材料の赤外線反射率曲線（実線）を
示す。
FIG. 1 shows an infrared reflectance curve (dashed line) of the colored product with carbon black and an infrared reflectance curve (solid line) of the infrared reflective material obtained in Example 13.
Claims (1)
0.3〜10μｍであるアゾ顔料及び担体材料からなる
赤外線反射性材料。 〔但し、上記式中のＸは、Ｎ＝Ｎ又はCONHで
あり、ｎは１又は２であり、R1は水素原子又は
ニトロ基であり、R2は、ハロゲン原子又はメト
キシ基であり、Ａ環はベンゼン環又はナフタレン
環であり、ｎ＝１のときのR3は、ハロゲン原子、
メチル基、ニトロ基又はメトキシ基を有してもよ
いフエニル基又は置換基を有していないナフチル
基であり、ｎ＝２のときR3は、メトキシ基を有
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
An infrared reflective material consisting of an azo pigment having a diameter of 0.3 to 10 μm and a carrier material. [However, X in the above formula is N=N or CONH, n is 1 or 2, R 1 is a hydrogen atom or a nitro group, R 2 is a halogen atom or a methoxy group, and A The ring is a benzene ring or a naphthalene ring, and when n=1, R 3 is a halogen atom,
A phenyl group that may have a methyl group, a nitro group, or a methoxy group, or a naphthyl group that does not have a substituent, and when n=2, R 3 is a biphenylene group that may have a methoxy group. . ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60206611A JPS6268858A (en) | 1985-09-20 | 1985-09-20 | Infrared-reflective material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60206611A JPS6268858A (en) | 1985-09-20 | 1985-09-20 | Infrared-reflective material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6268858A JPS6268858A (en) | 1987-03-28 |
| JPH0426348B2 true JPH0426348B2 (en) | 1992-05-07 |
Family
ID=16526247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60206611A Granted JPS6268858A (en) | 1985-09-20 | 1985-09-20 | Infrared-reflective material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6268858A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3794837B2 (en) * | 1998-10-27 | 2006-07-12 | 長島特殊塗料株式会社 | Thermal barrier paint and coating method thereof |
| JP2004027241A (en) * | 2003-10-14 | 2004-01-29 | Nagashima Tokushu Toryo Kk | Thermal insulation coating and its coating method |
| JP2016017242A (en) * | 2014-07-07 | 2016-02-01 | 山田化学工業株式会社 | Near infrared reflective polyamide fiber |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2477661A (en) * | 1943-03-13 | 1949-08-02 | Interchem Corp | Disazo dianisidine pigments |
| US3700397A (en) * | 1969-05-06 | 1972-10-24 | Us Army | Camouflaged article and method of producing same |
| JPS55144056A (en) * | 1979-04-24 | 1980-11-10 | Bayer Ag | Dyeing and printing of cellulosic fiber |
| JPS58178363A (en) * | 1982-04-13 | 1983-10-19 | Mita Ind Co Ltd | Electrophotographic receptor |
-
1985
- 1985-09-20 JP JP60206611A patent/JPS6268858A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2477661A (en) * | 1943-03-13 | 1949-08-02 | Interchem Corp | Disazo dianisidine pigments |
| US3700397A (en) * | 1969-05-06 | 1972-10-24 | Us Army | Camouflaged article and method of producing same |
| JPS55144056A (en) * | 1979-04-24 | 1980-11-10 | Bayer Ag | Dyeing and printing of cellulosic fiber |
| JPS58178363A (en) * | 1982-04-13 | 1983-10-19 | Mita Ind Co Ltd | Electrophotographic receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6268858A (en) | 1987-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |