JPH0713198B2 - Organic polymer material coloring pigment - Google Patents
Organic polymer material coloring pigmentInfo
- Publication number
- JPH0713198B2 JPH0713198B2 JP62027560A JP2756087A JPH0713198B2 JP H0713198 B2 JPH0713198 B2 JP H0713198B2 JP 62027560 A JP62027560 A JP 62027560A JP 2756087 A JP2756087 A JP 2756087A JP H0713198 B2 JPH0713198 B2 JP H0713198B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- colored
- polymer material
- organic polymer
- coloring
- 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
- 239000002861 polymer material Substances 0.000 title description 14
- 238000004040 coloring Methods 0.000 title description 12
- 229920000620 organic polymer Polymers 0.000 title description 11
- 239000000049 pigment Substances 0.000 title description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 17
- 239000000835 fiber Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 238000004043 dyeing Methods 0.000 description 12
- 239000000975 dye Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- -1 naphthalic acid compound Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920013716 polyethylene resin Polymers 0.000 description 4
- 229920001059 synthetic polymer Polymers 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、有機高分子材料着色用色素に関するものであ
る。詳しくは、本発明は、有機高分子材料、特に合成高
分子よりなる繊維あるいは薄膜、板などの成型品を鮮明
かつ堅牢な高濃度の赤色の色調に着色する際に使用する
色素に関するものである。The present invention relates to an organic polymer material coloring dye. More specifically, the present invention relates to a dye used for coloring a molded product such as a fiber or a thin film or a plate made of an organic polymer material, particularly a synthetic polymer, in a vivid and robust high-concentration red color tone. .
有機高分子材料を着色する色素およびその着色方法につ
いては、種々提案されており、例えば下記一般式で示さ
れるナフタル酸系化合物を使用した有機高分子材料の着
色方法が提案されている（特開昭54−18850号公報）。Various proposals have been made for a pigment for coloring an organic polymer material and a coloring method thereof, for example, a method for coloring an organic polymer material using a naphthalic acid compound represented by the following general formula has been proposed (JP 54-18850).
（式中、Ｒ′は水素原子、置換または非置換のアルキル
基、シクロアルキル基、アラルキル基、アリール基、ヒ
ドロキシル基、アシロキシ基、アルコキシ基、アミノ
基、アシルアミノ基、アルキルアミノ基またはアリール
アミノ基を示し、Ｒ″は水素原子、、アルキル基、アル
コキシ基、ニトロ基、ハロゲン原子、アシルアミノ基ま
たはアルキルアミノ基を示す。） 通常、有機高分子材料着色用色素は、繊維に適用する場
合には、水に不溶または難溶であるので、常法により、
分散剤を使用して、水性媒質中に分散させたものを、浸
染あるいは捺染に使用される。また、合成樹脂を着色す
る場合は、合成樹脂に配合し、加熱混練して、各種の成
型加工法による着色法に使用される。 (In the formula, R'is a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, a hydroxyl group, an acyloxy group, an alkoxy group, an amino group, an acylamino group, an alkylamino group or an arylamino group. And R ″ represents a hydrogen atom, an alkyl group, an alkoxy group, a nitro group, a halogen atom, an acylamino group or an alkylamino group.) In general, when an organic polymer material coloring dye is applied to a fiber, Since it is insoluble or poorly soluble in water,
The dispersant is used to disperse in an aqueous medium and used for dyeing or printing. Further, in the case of coloring a synthetic resin, it is mixed with the synthetic resin, kneaded by heating, and used in a coloring method by various molding processing methods.
しかし、従来の有機高分子材料用色素の場合、高分子材
料に対する着色性が不十分であり、色濃度をあまり高く
できず、なおかつ、耐光性、耐昇華性も劣るため、着色
性が良好で堅牢性にすぐれた高分子材料が得られていな
い。However, in the case of conventional dyes for organic polymer materials, the colorability of the polymer material is insufficient, the color density cannot be increased so much, and the light resistance and the sublimation resistance are poor, so that the colorability is good. Polymer materials with excellent robustness have not been obtained.
〔発明が解決しようとする問題点〕 本発明は、耐光性、耐熱性が良好で高濃度に着色する色
素を提供しようとするものである。[Problems to be Solved by the Invention] The present invention is intended to provide a dye which has good light resistance and heat resistance and is colored in a high concentration.
本発明は、耐光性、耐熱性、に優れ高濃度に着色するア
ザペリノン複素多環系化合物である。The present invention is an azaperinone heteropolycyclic compound which is excellent in light resistance and heat resistance and is colored in a high concentration.
すなわち、一般式〔Ｉ〕 （式中、Ｘ及びＹは同じでも異なつていても良く、水素
原子、ハロゲン原子、アルコキシ基またはアルキル基を
表わす。） で示される有機高分子材料着色用色素である。That is, the general formula [I] (In the formula, X and Y may be the same or different and each represents a hydrogen atom, a halogen atom, an alkoxy group or an alkyl group.).
Ｘ及びＹで表わされるアルキル基としては、メチル基、
エチル基、プロピル基、ブチル基、オクチル基等が挙げ
られ、アルコキシ基としては、メトキシ基、エトキシ
基、オクチルオキシ基等が挙げられ、ハロゲン原子とし
ては、塩素原子、臭素原子、フツ素原子、ヨウ素原子等
が挙げられる。The alkyl group represented by X and Y is a methyl group,
Ethyl group, propyl group, butyl group, octyl group and the like, alkoxy group, methoxy group, ethoxy group, octyloxy group and the like, the halogen atom, chlorine atom, bromine atom, fluorine atom, Examples thereof include iodine atom.
本発明の化合物は、例えば、次のようにして製造するこ
とができる。〔文献、西ら、日本学術振興会第116委員
会分科会資料（61.1.21）P55〕 すなわち、下記一般式〔II〕 （式中、Ｘ、Ｙは前記定義に同じ。） で示される化合物２モルと下記構造式〔III〕 で示される化合物１モルとをエタノール中70℃で縮合し
て下記一般式〔IV〕 （式中、Ｘ、Ｙは前記定義に同じ。） で示される化合物を得、次いでこれをα−クロロナフタ
レン中で煮沸することによつて製造することができる。The compound of the present invention can be produced, for example, as follows. [Literature, Nishi et al., Japan Society for the Promotion of Science 116th Committee Subcommittee Material (61.1.21) P55] That is, the following general formula [II] (Wherein X and Y are the same as defined above) and 2 mol of the compound represented by the following structural formula [III] 1 mol of the compound represented by (Wherein X and Y are the same as defined above), and then the compound can be prepared by boiling in α-chloronaphthalene.
本発明において適用される有機高分子材料としては、特
にポリエステル系、ポリアミド系、ポリウレタン系、ポ
リアクリロニトリル系、ポリオレフイン系、ポリ塩化ビ
ニル系、ポリスチレン系、ポリアクリレート系などの合
成高分子物質よりなる繊維、薄膜、板その他成型品があ
げられるが、セルロースアセテート系のような半合成高
分子物質よりなる繊維、その他の成型品であつてもよ
く、またポリエステル系繊維、ポリアミド系繊維、セル
ロースアセテート系繊維などの半合成または合成繊維相
互の混紡品、ないしはセルロース、羊毛などの天然繊維
との混紡品などのような種々の混紡品、あるいはABS系
などの共重合物からなる成型品であつてもよい。As the organic polymer material applied in the present invention, fibers made of synthetic polymer materials such as polyester, polyamide, polyurethane, polyacrylonitrile, polyolefin, polyvinyl chloride, polystyrene, and polyacrylate , Thin films, plates and other molded products, but fibers made of semi-synthetic polymer such as cellulose acetate, other molded products, polyester fiber, polyamide fiber, cellulose acetate fiber It may be a blended product of semi-synthetic or synthetic fibers such as, or various blended products such as a blended product with cellulose, natural fibers such as wool, or a molded product made of a copolymer such as ABS. .
本発明の方法に従つて前記の有機高分子材料を着色する
には、繊維に適用する場合には、本発明に使用される前
示一般式〔Ｉ〕で表わされる化合物は、水に不溶または
難溶であるので、常法により分散剤を使用して水性媒質
中に分散させた染色浴あるいは捺染糊を調製し、浸染ま
たは捺染を行なえばよい。例えば、浸染の場合、煮沸染
色法、高温染色法、キヤリヤー染色法、サーモゾル染色
法などのような分散染料染色法をそのまま適用すれば、
半合成または合成繊維ないしはその混紡品に諸堅牢度の
すぐれた着色を施すことができる。また、前示一般式
〔Ｉ〕で表わされる化合物は、ポリエステル繊維のよう
な合成繊維の製造過程における重合時、あるいは紡糸時
に添加して着色する、いわゆる原液着色法に適用するこ
とができる。In order to color the above-mentioned organic polymer material according to the method of the present invention, when it is applied to fibers, the compound represented by the above general formula [I] used in the present invention is insoluble in water or Since it is sparingly soluble, a dyeing bath or a printing paste dispersed in an aqueous medium using a dispersant may be prepared by a conventional method, and the dyeing or the printing may be carried out. For example, in the case of dip dyeing, if a disperse dyeing method such as a boiling dyeing method, a high temperature dyeing method, a carrier dyeing method, a thermosol dyeing method is applied as it is,
A semi-synthetic or synthetic fiber or a blended product thereof can be colored with excellent fastness. Further, the compound represented by the general formula [I] shown above can be applied to a so-called undiluted solution coloring method in which the compound is colored by adding it at the time of polymerization or spinning during the production process of synthetic fiber such as polyester fiber.
合成樹脂を着色する場合は、前示一般式〔Ｉ〕で表わさ
れる化合物の所要量を合成樹脂に配合し、加熱混練して
圧縮成型法、射出成型法、カレンダー成型法、押出成型
法などの通常の成型加工法を適用すれば、フイルム、シ
ート、パイプその他成型品に堅牢な着色を施すことがで
きる。更に、液状のモノマー、プレポリマーに前示一般
式〔Ｉ〕で表わされる化合物を配合して、重合、硬化さ
せるキヤスト成膜法によつても堅牢に着色された成型品
を得ることができる。In the case of coloring a synthetic resin, a required amount of the compound represented by the general formula [I] shown above is blended with the synthetic resin, and the mixture is kneaded by heating, followed by compression molding, injection molding, calender molding, extrusion molding and the like. By applying an ordinary molding method, a film, sheet, pipe or other molded article can be colored robustly. Furthermore, a cast product which is robustly colored can also be obtained by a cast film-forming method in which the liquid monomer or prepolymer is mixed with the compound represented by the above-mentioned general formula [I] and the compound is polymerized and cured.
次に本発明を実施例によつて更に具体的に説明するが、
本発明はその要旨を越えない限り、これらの実施例に限
定されるものではない。Next, the present invention will be described more specifically with reference to Examples.
The present invention is not limited to these examples as long as the gist thereof is not exceeded.
実施例１ 下記構造式 で表わされる化合物0.5gをポリエチレン樹脂〔NOVATEC
JV070（HDPE）：三菱化成工業（株）商品名〕10kgに
配合して、加熱シリンダー温度200〜240℃に加融混練
し、220℃、２分で射出成型したところ、厚さ2mmの堅牢
な高濃度の鮮明な青味赤色に着色されたポリエチレン樹
脂板が得られた。Example 1 The following structural formula0.5 g of the compound represented by
JV070 (HDPE): Mitsubishi Kasei Kogyo Co., Ltd. product name] 10kg
Mix and melt and knead at a heating cylinder temperature of 200-240 ℃
Then, injection molded at 220 ° C for 2 minutes, it is 2mm thick and robust.
High concentration of vivid bluish red colored polyethylene tree
A fat plate was obtained.
標準条件（220℃×２分）の着色板に対する耐熱条件（2
80℃×２分、10分）の着色板の変退色の度合いをグレー
スケール及びΔＥ＊ab値（色差）で判定する方法で上記
着色板の耐熱性を評価したところ、グレースケール４〜
５級、ΔＥ＊ab1.20であり、良好であつた。Heat resistance condition (2) under standard conditions (220 ° C x 2 minutes)
When the heat resistance of the colored plate was evaluated by a method of judging the degree of discoloration / discoloration of the colored plate at 80 ° C. × 2 minutes, 10 minutes) by the gray scale and ΔE * ab value (color difference), the gray scale of 4 to 4 was obtained.
Grade 5, ΔE * ab1.20, which was good.
またカーボンアークフエードメーターにて63℃×100時
間露光し、未露光部との変退色の度合いをグレースケー
ル及びΔＥ＊ab値（色差）で判定する方法で上記着色ポ
リエチレン樹脂板の耐光性を評価したところ、グレース
ケール３〜４級、ΔＥ＊ab4.00であり良好であつた。In addition, the light resistance of the above-mentioned colored polyethylene resin plate is evaluated by a method of judging the degree of discoloration with the unexposed area by gray scale and ΔE * ab value (color difference) by exposing with a carbon arc fade meter at 63 ° C for 100 hours. As a result of evaluation, the gray scale grades 3 to 4 and ΔE * ab4.00 were favorable.
実施例２ 下記構造式 で表わされる化合物0.6gをポリエチレン樹脂〔NOVATEC
JV070（HDPE）〕10kgに配合して、実施例１と同様に加
融混練・射出成型して、厚さ2mmの堅牢な高濃度の青味
赤色に着色されたポリエチレン樹脂板が得られた。Example 2 The following structural formula 0.6 g of the compound represented by
JV070 (HDPE)] 10 kg, and melt-kneading / injection molding in the same manner as in Example 1 to obtain a robust high-concentration bluish red colored polyethylene resin plate having a thickness of 2 mm.
上記ポリエチレン樹脂板の耐熱性および耐光性はいずれ
も良好であつた。Both the heat resistance and the light resistance of the polyethylene resin plate were good.
実施例３ 下記表に示した化合物を用いて、実施例１と同様の方法
でポリエチレン樹脂を着色し、同表に示すように高濃度
の鮮明な色調の樹脂板を得た。着色板の耐熱性および耐
光性は良好であつた。Example 3 Using the compounds shown in the table below, the polyethylene resin was colored in the same manner as in Example 1 to obtain a resin plate having a high density and a clear color tone as shown in the table. The heat resistance and light resistance of the colored plate were good.
実施例４ 実施例１で使用した化合物0.2gをポリスチレン樹脂1kg
に配合して、加熱シリンダー温度200〜240℃に加融混練
し、常法により射出成型したところ厚さ2mmの堅牢な高
濃度の鮮明な青味赤色に着色されたポリスチレン樹脂板
が得られた。 Example 4 0.2 g of the compound used in Example 1 was added to 1 kg of polystyrene resin.
Was blended with, melted and kneaded at a heating cylinder temperature of 200 to 240 ° C., and injection-molded by a conventional method to obtain a robust high-concentration vivid reddish-colored polystyrene resin plate having a thickness of 2 mm. .
着色板の耐光性は良好であつた。The light resistance of the colored plate was good.
実施例５ メチルメタクリレート（モノマー）1kgに重合開始剤を
加えて予備重合を行ない、得られたシラツプに実施例１
で使用した化合物0.2gを添加溶解し、この着色シラツプ
をガラスセル中に注入して、50〜70℃で６時間、次いで
100〜120℃で３時間重合させた後、冷却したところ、堅
牢な高濃度の鮮明な青味赤色に着色されたポリメチルメ
タクリレート樹脂板（板厚さ5mm）が得られた。Example 5 Prepolymerization was carried out by adding a polymerization initiator to 1 kg of methyl methacrylate (monomer), and the resulting syrup was subjected to Example 1
0.2 g of the compound used in 1. was added and dissolved, and the colored syrup was poured into a glass cell, and the mixture was heated at 50 to 70 ° C. for 6 hours, and then,
After polymerizing at 100 to 120 ° C. for 3 hours and then cooling, a robust high-density polymethylmethacrylate resin plate (plate thickness 5 mm) colored in a vivid bluish red was obtained.
着色板の耐光性は良好であつた。The light resistance of the colored plate was good.
実施例６ 実施例３−７で使用した化合物0.5gをナフタレンスルホ
ン酸ホルムアルデヒド縮合物1gおよび高級アルキルベン
ゼンスルホン酸ソーダ1gを含む水３に分散させて染色
浴を調製し、この染色浴にポリアミド繊維100gを浸漬
し、100℃で90分間染色した後、ソーピング、水洗、乾
燥した。Example 6 A dyeing bath is prepared by dispersing 0.5 g of the compound used in Example 3-7 in water 3 containing 1 g of naphthalene sulfonic acid formaldehyde condensate and 1 g of higher alkylbenzene sulfonic acid soda, and 100 g of polyamide fiber is added to the dyeing bath. Was dipped and dyed at 100 ° C. for 90 minutes, then soaped, washed with water and dried.
得られた青味赤色を呈するポリアミド繊維は、耐光性が
良好であつた。The obtained bluish red polyamide fiber had good light resistance.
実施例７ 実施例３−８で使用した化合物0.5gをナフタレンスルホ
ン酸とホルムアルデヒドの縮合物1g及び高級アルコール
硫酸エステル2gを含む水３に分散させて染色浴を調製
した。Example 7 A dye bath was prepared by dispersing 0.5 g of the compound used in Example 3-8 in water 3 containing 1 g of a condensate of naphthalene sulfonic acid and formaldehyde and 2 g of a higher alcohol sulfate ester.
この染色浴にポリエステル繊維100gを浸漬し、130℃で6
0分間染色した後、ソーピング、水洗、乾燥した。Dip 100 g of polyester fiber in this dyeing bath,
After dyeing for 0 minutes, it was soaped, washed with water, and dried.
得られた青味赤色を呈するポリエステル繊維は、耐光堅
牢度および昇華堅牢度が良好であつた。The obtained bluish red polyester fiber had good fastness to light and fastness to sublimation.
本発明の有機高分子材料着色用色素によれば、有機高分
子材料、特に合成高分子よりなる繊維あるいは薄膜、板
などの成型品を鮮明かつ堅牢な高濃度の赤色に着色で
き、得られた着色物は、耐光性、耐熱性に優れる。According to the dye for coloring an organic polymer material of the present invention, a molded product such as a fiber or a thin film or a plate made of an organic polymer material, particularly a synthetic polymer, can be colored in a clear and robust high-concentration red color. The colored product has excellent light resistance and heat resistance.
Claims (1)
原子、ハロゲン原子、アルコキシ基またはアルキル基を
表わす。） で示される有機高分子材料着色用色素。1. A general formula [I] (In the formula, X and Y may be the same or different and each represents a hydrogen atom, a halogen atom, an alkoxy group or an alkyl group.).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62027560A JPH0713198B2 (en) | 1987-02-09 | 1987-02-09 | Organic polymer material coloring pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62027560A JPH0713198B2 (en) | 1987-02-09 | 1987-02-09 | Organic polymer material coloring pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63193960A JPS63193960A (en) | 1988-08-11 |
| JPH0713198B2 true JPH0713198B2 (en) | 1995-02-15 |
Family
ID=12224426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62027560A Expired - Lifetime JPH0713198B2 (en) | 1987-02-09 | 1987-02-09 | Organic polymer material coloring pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0713198B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5028643A (en) * | 1989-06-27 | 1991-07-02 | Ciba-Geigy Corporation | Tetrabenzodiazadiketoperylene pigment |
| US7544448B2 (en) * | 2005-11-21 | 2009-06-09 | Ciba Specialty Chemicals Corporation | Tetrabenzodiazadiketoperylene pigments for laser marking |
| DE602007001577D1 (en) * | 2006-01-18 | 2009-08-27 | Ciba Holding Inc | TETRABENZODIAZADICETOPERYLENE STAINING AGENT IN IR-REFLECTIVE COATINGS AND PLASTICS |
| EP2094497B1 (en) * | 2006-11-07 | 2010-12-15 | Basf Se | Laser marking of pigmented substrates |
| US9204598B2 (en) | 2013-05-27 | 2015-12-08 | Saudi Basic Indsutries Corporation | Solar energy funneling using thermoplastics for agricultural applications |
| JP7086391B2 (en) * | 2017-09-25 | 2022-06-20 | 国立研究開発法人理化学研究所 | Quinoid-type π-conjugated near-infrared organic dye compound |
-
1987
- 1987-02-09 JP JP62027560A patent/JPH0713198B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63193960A (en) | 1988-08-11 |
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