JPH03126768A - New pigment - Google Patents

New pigment

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Publication number
JPH03126768A
JPH03126768A JP2263215A JP26321590A JPH03126768A JP H03126768 A JPH03126768 A JP H03126768A JP 2263215 A JP2263215 A JP 2263215A JP 26321590 A JP26321590 A JP 26321590A JP H03126768 A JPH03126768 A JP H03126768A
Authority
JP
Japan
Prior art keywords
formulas
tables
mathematical
chemical formulas
chemical
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.)
Granted
Application number
JP2263215A
Other languages
Japanese (ja)
Other versions
JP2956907B2 (en
Inventor
Bansi Lal Kaul
バンジ　ラル　カウル
Angelos-Elie Vougioukas
アンジェロ―エリ　ブジウカ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Coloring (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Dental Preparations (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

NEW MATERIAL: A salt of the general formula: IFn A [wherein F is an anion dye residue having 1 to 4 acid groups and free of metal; (n) is 1 to 2; and A is a group containing 1 to 4 sterically hindered amine groups and a group contg. at least n ammonium(s) or immonium(s)].
USE: A colorant for resins such as PVC, polyolefins, polyisobutylenes and polystyrenes; a lacquer; and a printing ink for obtaining printed cloths. Even when it is used in a small amount, the color density is extremely high and the colored substances are excellent in the fastness to sunlight. The substances to which the compound is applied are extremely stable to UV rays and heat.
PREPARATION: An acid group-contg. non-metallized dye F (pref. a compd. of the formula or the like) is reacted with a basic compd. A [pref. bis-(2',2',6',6'- tetramethylpiperidyl-4')-terephthalamide].
COPYRIGHT: (C)1991,JPO

Description

【発明の詳細な説明】 本発明は、酸性染料と少なくとも１個の立体障害アくン
基を有する塩基性化合物との実質的に不溶性の塩である
新規な有機化合物に関する。これ３ らの化合物は、溶剤を含まないプラスチック材料および
溶剤を含むプラスチック材料の着色に特に適するピグメ
ントとして優れている。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel organic compounds that are substantially insoluble salts of acidic dyes and basic compounds having at least one sterically hindered atom group. These three compounds are distinguished as pigments which are particularly suitable for the coloring of solvent-free and solvent-containing plastic materials.

本発明によれば下記式（Ｉ）の塩が提供される。According to the present invention, a salt of the following formula (I) is provided.

Ｆｌｌ−Ａ　　　　　（Ｉ） 上式中、Ｆは１〜４個の酸基を有し、金属を含まないア
ニオン染料の残基を表し、ｎは１〜２を表し、Ａは１〜
４個の立体障害アミン基および少なくともｎ個のアンモ
ニウムまたはインモニウム基を含む基を表す。Fll-A (I) In the above formula, F represents a residue of an anionic dye having 1 to 4 acid groups and not containing metal, n represents 1 to 2, and A represents 1 to 2.
Represents a group containing four sterically hindered amine groups and at least n ammonium or immonium groups.

本発明に係るピグメントは、ｐｖｃ　、あらゆるタイプ
のポリオレフィン（ＨＤＰＲまたはＬＤＰＥ、高密度ポ
リエチレンまたは低密度ポリエチレンまたはポリプロピ
レン）、ポリイソブチレン、ポリ−４−メチルペンテン
およびそれらのコポリマーを着色するために優れている
。さらに、本発明に係る化合物は、ポリスチレン（およ
びそのコポリマー）、ＡＢＳ　、ポリ酢酸ビニル、ポリ
ビニルアルコール、ポリアセテート、ＰＯＭ　、ポリア
クリレート、ポリアクリロニトリル、ポリアクリルアミ
ド、ポリ塩４ 化ビニリデン、ポリエステル、ポリエーテル、ポリチオ
エーテルおよびチオプラスト、ポリカーボネート、ボリ
ウレクン、セルロース誘導体、マレイン酸、メラミン、
フェノール、アニリン、フラン、カルバミド、エポキシ
ドおよびシリコーン樹脂の着色に用いることができる。The pigments according to the invention are excellent for coloring PVC, all types of polyolefins (HDPR or LDPE, high-density polyethylene or low-density polyethylene or polypropylene), polyisobutylene, poly-4-methylpentene and their copolymers. . Furthermore, the compounds according to the present invention include polystyrene (and copolymers thereof), ABS, polyvinyl acetate, polyvinyl alcohol, polyacetate, POM, polyacrylate, polyacrylonitrile, polyacrylamide, polyvinylidene tetrachloride, polyester, polyether, Polythioethers and thioplasts, polycarbonates, polyurecne, cellulose derivatives, maleic acid, melamine,
Can be used to color phenol, aniline, furan, carbamide, epoxide and silicone resins.

式（Ｉ）の化合物は、また、ラッカーおよび絵柄付き布
帛のための印刷インクに用いることができる。The compounds of formula (I) can also be used in printing inks for lacquers and patterned fabrics.

好ましくは、ＦはＦ゛即ちアゾ列、フタロシアニン列、
アントラキノン列、ペリレン列、インジゴ列、チオイン
ジゴ列、ペリノン列、キナクリドン列、ジオキサジン列
、イソインドリン列、イソイソトリノン列、ジケトピロ
ール列またはビロール列、特にアゾ、フタロシアニン、
インジゴ、アントラキノン、ジオキサジンおよびイソイ
ソトリノン列の、酸基含有非金属化染料から誘導された
基である。Preferably, F is an azo series, a phthalocyanine series,
Anthraquinone series, perylene series, indigo series, thioindigo series, perinone series, quinacridone series, dioxazine series, isoindoline series, isoisotrinon series, diketopyrrole series or virole series, especially azo, phthalocyanines,
A group derived from acid group-containing non-metallized dyes of the indigo, anthraquinone, dioxazine and isoisotrinon series.

さらに好ましくは、ＦはＦ　ｌ　＋即ち下記式Ｆ１〜Ｆ
４３の化合物である。More preferably, F is F l +, that is, the following formulas F1 to F
There are 43 compounds.

（式中、 Ｒ９ はクロロ、 ブロモ、 １ アルキル またはＣ アルコキシを表し、 ｍは１． ２また は３を表す。(In the formula, R9 is Chrollo, Bromo, 1 alkyl or C represents alkoxy, m is 1. 2 again represents 3.

） 好ましくは、 存在するいかなる立体障害基も下 ２０ 好ましくは、 ＡはＡ′ 即ち下記のＡ。) Preferably, Any sterically hindering groups present are 20 Preferably, A is A' That is, A below.

〜Ａ　２　ｇか 上式中、Ｒｏは水素またはＣ１，−４アルキル、好まし
くは水素またはメチル、さらに好ましくは水素を表し、
Ｒ＋□はそれぞれ独立にＣＩ−６アルキル、好ましくは
メチルを表し、Ｒ＋＋は共に独立に水素、メチルまたは
エチルを表すかまたは一方の基ＲＩ３がフェニルを表し
、または両方の基ＲＩ２が一緒になって（ＣＨ２）の基
を形成しており、Ｙは弐−ＮＧＯまたは−Ｃｏ−Ｎ−の
基を表す。~A 2 g In the above formula, Ro represents hydrogen or C1,-4 alkyl, preferably hydrogen or methyl, more preferably hydrogen,
R+□ each independently represents CI-6 alkyl, preferably methyl, R++ both independently represent hydrogen, methyl or ethyl, or one radical RI3 represents phenyl, or both radicals RI2 together (CH2) group, and Y represents a -NGO or -Co-N- group.

１ Ａ、　　１，３．５−　　トリー（２”、２’、６”、
６゛−テトラメチルピペリジル−４゛）−トリメシン酸
トリアξド六ｚ　　２．４−ビス−（２’　、２’　、
６’　、６’−テトラメチルピペリジル−４゛−アミノ
）−６−クロロトリアジンＡｓ　　２，４．６−　トリ
ー（２’、２’、６°、６′−テトラメチルピペリジル
−４”−ア亀））＝トリアジンＡ４　ビス−（２°２゛
６°、６”−テトラメチルピペリジル−４゛−アくノカ
ルボニルパラフェニレン）−テレフタル酸ジイミド Ａ、　ビス−（２’、２’、６’、６”−テトラメチル
ピペリジル−４゛）−テレフタル酸アミド Ａ６　２．４−ビス−（２’、２’　、６’　、６’−
テトラメチルピペリジル−４′〜アミノ）−キナゾリン
Ａ？　　２．３−ビス−（２’、２°、６’、６’−テ
トラメチルピペリジル−４゛−アξ）〉−キノフサリン
Ａｅ　　１．４−ビス−（２’、２’、６”、６゛−テ
トラメチルピペリジル−４゛−アミノ）−フタラジン２ Ａ、　　２−クロロ−４，６−ビス−（２’、２’、６
’、６’−テトラメチルピペリジル−４−アミノ）−ビ
ＩＪミジンＡ、Ｉ０２．５−ジクロロ−４，６−ビス＝
（２’、２”、６”、６゛−テトラメチルピペリジル−
４−アミノ）−ビ１ノミジンＡ＋＋２−フルオロ−５−
クロロ−４，６−ビス−（２’、２．６’、６’−テ）
　ラメチルピペリジル−４−アミノ）−ピリミジン Ａ＋ｔ　２，４．６−　　）リ−（２’　、２’　、６
’　、６−チトラメチルピベリジルー４゛−ア藁））−
ビリえジンＡｌｌ　２．４．６−　　）す、−（２’、
２”、６°、６゛−テトラメチルピペリジル−４゛−ア
藁））−５−クロロビＩＪミジン３ Ａ　＋　ｂ Ａ＋ｑ 　ｔ　ｅ ＝２４ Ｃｏ−８１（−Ｒ３ Ａ　２２　　ビス−（１，２，２，６，６−ベンタメチ
ルビペ１ノジルー４）−テレフタル酸アミド Ａ　Ｚ　４　　ビス−（１，２，２，６，６−ペソタメ
チルピペ１ノジルー４）−イソフタル酸アミド ５ 　Ｚ　５ Ｒ１−■−ＣＯＱＣＯ−■−Ｒ１ ｘｅ Ｒ，−Ｃｏ−ＮＨ−Ｃ）−ＮＨ−Ｃｏ−Ｒ１上式中、Ｒ
４は２，２．６．６−チトラメチルピベリジルー４−を
表し、Ｒ４，は前記式（ｂ）の基を表し、Ｒ２はＹが一
′″Ｎ−Ｃ０−：’ｒある前記式（ｃ）の基を表し、Ｒ
５’はＹが−”Ｃ０−Ｎ−である前記式（ｃ）の基を表
し、ここで１を付した原子がピペリジル基に結合してい
るものとし、Ｒ６は前記式（ｄ）の基を表し、Ｒ９は前
記式（ｅ）の基を表す。1 A, 1,3.5-tree (2", 2', 6",
6゛-tetramethylpiperidyl-4゛)-trimesic acid triξdo6z 2.4-bis-(2', 2',
6',6'-tetramethylpiperidyl-4'-amino)-6-chlorotriazine As 2,4.6-tri(2',2',6°,6'-tetramethylpiperidyl-4''-amino) )) = triazine A4 bis-(2°2゛6°, 6''-tetramethylpiperidyl-4゛-acnocarbonylparaphenylene)-terephthalic acid diimide A, bis-(2', 2', 6', 6''-tetramethylpiperidyl-4')-terephthalic acid amide A6 2,4-bis-(2', 2', 6', 6'-
Tetramethylpiperidyl-4'-amino)-quinazoline A? 2.3-bis-(2′,2°,6′,6′-tetramethylpiperidyl-4゛-aξ)〉-quinophsarin Ae 1.4-bis-(2′,2′,6”,6゛-Tetramethylpiperidyl-4゛-amino)-phthalazine 2 A, 2-chloro-4,6-bis-(2', 2', 6
',6'-tetramethylpiperidyl-4-amino)-biIJ midine A, I02.5-dichloro-4,6-bis=
(2', 2", 6", 6'-tetramethylpiperidyl-
4-amino)-bi1 nomidine A++2-fluoro-5-
Chloro-4,6-bis-(2',2.6',6'-te)
lamethylpiperidyl-4-amino)-pyrimidine A+t2,4.6-)ly-(2',2',6
, 6-titramethylpiveridyl-4゛-a straw))-
Viriejin All 2.4.6-)su,-(2',
2", 6°, 6'-tetramethylpiperidyl-4'-a-))-5-chlorobiIJmidine3 A + b A+q t e =24 Co-81(-R3 A 22 bis-(1,2, 2,6,6-bentamethylpipe 1 nozyru 4)-terephthalic acid amide A Z 4 bis-(1,2,2,6,6-pestamethylpipe 1 nojiru 4)-isophthalic acid amide 5 Z 5 R1-■-COQCO-■ -R1 xe R, -Co-NH-C) -NH-Co-R1 In the above formula, R
4 represents 2,2.6.6-titramethylpiveridyl-4-, R4 represents a group of the above formula (b), and R2 represents the above formula in which Y is 1'''N-C0-:'r (c) represents the group R
5' represents the group of the above formula (c) in which Y is -"C0-N-, where the atom with 1 is bonded to the piperidyl group, and R6 represents the group of the above formula (d) and R9 represents a group of the above formula (e).

式Ａ１〜Ａ　ｚ　ｑの化合物の製造は、公知の方法によ
って、好ましくは、対応するアミンを対応するカルボン
酸（またはカルボン酸クロリド）との縮２６ 合によって、または例えば対応するアミンとトリクロロ
トリアジン、ジクロロキナゾリン、ジクロロキノフサリ
ン、ジクロロフタラジン、トリまたはテトラクロロピリ
ミジンとの縮合によって、実施することができる。式（
ａ）〜（ｅ）の基を含む対応する化合物は公知である。The compounds of formulas A1 to Azq are prepared by known methods, preferably by condensation of the corresponding amines with the corresponding carboxylic acids (or carboxylic acid chlorides) or, for example, by condensation of the corresponding amines with trichlorotriazine, This can be carried out by condensation with dichloroquinazoline, dichloroquinophthalin, dichlorophthalazine, tri- or tetrachloropyrimidine. formula(
Corresponding compounds containing groups a) to (e) are known.

新規なピグメントの製造は、適当な染料を塩基性化合物
で公知の方法により塩化することにより実施することが
できる。例えば、製造後に得られた、即ちナトリウム塩
形の酸性染料を、適当な量の鉱酸く例えばＩＩｃＩ）の
存在において、塩基性成分Ａと反応させることにより、
式（ｒ）の塩を得ることができる。The novel pigments can be prepared by salifying suitable dyes with basic compounds by known methods. For example, by reacting the acid dye obtained after manufacture, i.e. in the sodium salt form, with the basic component A in the presence of a suitable amount of a mineral acid (e.g. IIcI),
A salt of formula (r) can be obtained.

式（Ｉ）の化合物は、少量で用いられる場合にも、また
他の有機ピグメントに対して通常の量で用いられる場合
にも、極めて大きい色強度を有する。The compounds of formula (I) have extremely high color intensities both when used in small amounts and in amounts customary for other organic pigments.

通常の使用量は着色されるべき基材の重量の０．０２〜
５％、さらに好ましくは０．０６〜３％である。式（１
）の化合物を用いた着色物は優れた日光堅牢度を示す。The usual amount used is 0.02 to 0.02 of the weight of the substrate to be colored.
5%, more preferably 0.06 to 3%. Formula (1
) shows excellent light fastness.

さらに、式（１）の化合物が適用された基材は、紫外光
、熱および酸化の悪影響に対して優れた安定性を示す。Furthermore, the substrate to which the compound of formula (1) is applied exhibits excellent stability against the adverse effects of ultraviolet light, heat and oxidation.

下記の例は本発明をさらに説明するためのものである。The following examples serve to further illustrate the invention.

例中、部および％は重量で示し、温度は°Ｃで示す。In the examples, parts and percentages are given by weight and temperatures are given in °C.

例１ ａ）　１０．１５部のテレフタル酸ジクロリドを７０部
のトルエン中で攪拌し、室温で３時間で１９．５部のト
リアセトンシア５ンを添加した。得られた懸濁液をさら
に３０部のトルエンで希釈し、還流下に絶えず攪拌しな
がら１８時間沸騰させた。生した沈澱を濾過し、アセト
ンで洗浄し、５０部の水中で攪拌し、水酸化ナトリウム
によりｐｕを約１３とし、再び濾過し、水洗し、真空乾
燥した。得られた白色粉末は３００°以上の温度で融解
する。Example 1 a) 10.15 parts of terephthalic acid dichloride are stirred in 70 parts of toluene and 19.5 parts of triacetone cyanide are added in 3 hours at room temperature. The resulting suspension was further diluted with 30 parts of toluene and boiled under reflux with constant stirring for 18 hours. The resulting precipitate was filtered, washed with acetone, stirred in 50 parts of water, brought to a pu of about 13 with sodium hydroxide, filtered again, washed with water, and dried in vacuo. The white powder obtained melts at temperatures above 300°.

ｂ）　４．８４部の３．４−ジクロロアニリン−６−ス
ルホン酸を１１部の１５％塩酸に溶解し、溶液をＯ〜４
゜に冷却し、６部の４Ｎ　ＮａＮ０□によりジアゾ化し
、過剰のＮａＮ０□をアミノスルホン酸で分解させた。b) Dissolve 4.84 parts of 3,4-dichloroaniline-6-sulfonic acid in 11 parts of 15% hydrochloric acid and bring the solution to O~4
The mixture was cooled to 20°C, diazotized with 6 parts of 4N NaNO□, and excess NaNO□ was decomposed with aminosulfonic acid.

２０部の水中３．４８部の１−フェニル−３−メチル−
５ピラゾロンの溶液および２．２部の３０％水酸化ナト
リウムを、混合物を０〜４°に保持しながら添加した。3.48 parts of 1-phenyl-3-methyl- in 20 parts of water
A solution of 5 pyrazolone and 2.2 parts of 30% sodium hydroxide were added while maintaining the mixture at 0-4°.

添加はゆっくり攪拌下に行った。これを室温で１８時間
攪拌し、攪拌下に６０で２時間加熱し、濾過し、残留物
を水洗した。次に、乾燥し、水に取り、ｐＨを希ＮａＯ
Ｈを用いて約８．５にした。The addition was carried out slowly and with stirring. This was stirred at room temperature for 18 hours, heated under stirring at 60°C for 2 hours, filtered and the residue was washed with water. Then dry, take in water and adjust the pH to dilute NaO
The temperature was adjusted to about 8.5 using H.

ｃ）　４．４２部の上記ａ）の生成物を３０部の水およ
び１．９部の３３％塩酸中の溶液とした。上記ｂ）の混
合物を、攪拌下に、３０分間でゆっくり添加し、安定性
を改良するためにさらにこの混合物に水を添加した。混
合物を６０°に２．５時間加熱し、室温に冷却し、残留
物を濾過し、水洗し、乾燥した。得られた黄オレンジ色
の粉末の融点は３００°以上であった。c) 4.42 parts of the product from a) above were taken up in solution in 30 parts of water and 1.9 parts of 33% hydrochloric acid. The mixture of b) above was added slowly over 30 minutes under stirring and water was further added to the mixture to improve stability. The mixture was heated to 60° for 2.5 hours, cooled to room temperature and the residue was filtered, washed with water and dried. The melting point of the yellow-orange powder obtained was 300° or higher.

例１のそれと同一の方法により、下記式の他のピグメン
トを公知の化合物から製造することができた。By a method identical to that of Example 1, other pigments of the formula below could be prepared from known compounds.

Ｔｌ　−Ａ 式中、記号は表に示した意味を有する。Tl-A In the formula, the symbols have the meanings shown in the table.

着色された基材の色相を表中の最後の欄に示す。The hue of the colored substrate is shown in the last column of the table.

９ 例番号 着色色相 ０ 表菖二とＬｌｌ 例番号 着色色相 適用例Ａ ４部の例Ｉのピグメントを９６部の下記の混合物と共に
ボールミル中で２４時間粉砕した。9 Example No. Colored Hue 0 Table Iris and Lll Example No. Colored Hue Application Example A 4 parts of the pigment of Example I were ground for 24 hours in a ball mill with 96 parts of the following mixture.

５０部のキシレン中３２％の含脂量を有するココアルデ
ヒドメラミン樹脂の６０％溶液、 ３０部のブタノール中５０％メラミン樹脂溶液、１０部
のキシレン、および １０部のエチレングリコールモノエチルエーテル得られ
た分散液をアルミニウムシート上にスプレーし、空気中
で３０分間乾燥し、次いで１２０”で３０分間焼付けし
た。明るい赤味黄色の、極めて良好な日光および耐候堅
牢度を有するフィルムが得られた。A 60% solution of cocoaaldehyde melamine resin with a fat content of 32% in 50 parts of xylene, 30 parts of a 50% melamine resin solution in butanol, 10 parts of xylene, and 10 parts of ethylene glycol monoethyl ether was obtained. The dispersion was sprayed onto an aluminum sheet, dried in air for 30 minutes and then baked at 120'' for 30 minutes. A bright reddish-yellow film with very good sun and weather fastness was obtained.

適用例Ｂ ０．１％の色素着色ＰＶＣシート　（有色ピグメント対
白色ピグメントの比１：５）を下記のようにして製造す
ることができた。Application Example B A 0.1% pigmented PVC sheet (ratio of colored pigments to white pigments 1:5) could be produced as follows.

等量のジオクチルフタレートおよびジブチルフタレート
の混合物１６．５部を、０．０５部の例１のピグメント
および０．２５部の二酸化チタンと混合した。16.5 parts of a mixture of equal amounts of dioctyl phthalate and dibutyl phthalate were mixed with 0.05 part of the pigment of Example 1 and 0.25 part of titanium dioxide.

３３．５部のポリ塩化ビニルを添加した。混合物を２つ
のローラーガンでロールがけして、シートを製造し、こ
れをスパチュラでカットし、再び一緒にロールかけした
。ローラーの一方を４０’に保持し、他方を１４０°に
保持した。最後に、混合物をシートとして取り、ツヤ出
し金属プレートの間で１６００で５分間プレスした。33.5 parts of polyvinyl chloride were added. The mixture was rolled with two roller guns to produce sheets, which were cut with a spatula and rolled together again. One of the rollers was held at 40' and the other at 140°. Finally, the mixture was taken as a sheet and pressed between polished metal plates at 1600 for 5 minutes.

赤味黄色に着色された、高度の明るさおよび極めて良好
なマイグレーションおよび日光堅牢度を有するＰｖＣフ
ォリオが得られた。A reddish-yellow colored PvC folio with a high degree of brightness and very good migration and light fastness was obtained.

例１のピグメントの代わりに、同し量の例２〜５９の生
成物のいずれか１つを用いても適用例ＡおよびＢを繰り
返すことができた。Application examples A and B could also be repeated using, instead of the pigment of example 1, the same amount of any one of the products of examples 2 to 59.

３3

Claims (1)

【特許請求の範囲】 １、下記式（ I ）で示される塩 Ｆ＿ｎ・Ａ（ I ） 上式中、Ｆは１〜４個の酸基を有し、金属を含まないア
ニオン染料の残基を表し、ｎは１〜２を表し、Ａは１〜
４個の立体障害アミン基および少なくともｎ個のアンモ
ニウムまたはインモニウム基を含む基を表す。 ２、ＦがＦ′即ちアゾ列、フタロシアニン列、アントラ
キノン列、ペリレン列、インジゴ列、チオインジゴ列、
ペリノン列、キナクリドン列、ジオキサジン列、イソイ
ンドリン列、イソイソトリノン列、ジケトピロール列ま
たはピロール列、特にアゾ、フタロシアニン、インジゴ
、アントラキノン、ジオキサジンおよびイソイソトリノ
ン列の、酸基含有非金属化染料から誘導された基である
、請求項１記載の化合物。 ３、ＦがＦ″即ち下記式Ｆ＿１〜Ｆ＿４＿３の化合物で
ある、請求項１または２記載の化合物。 Ｆ＿１▲数式、化学式、表等があります▼Ｆ＿２▲数式
、化学式、表等があります▼ Ｆ＿３▲数式、化学式、表等があります▼Ｆ＿４▲数式
、化学式、表等があります▼ Ｆ＿５▲数式、化学式、表等があります▼Ｆ＿６▲数式
、化学式、表等があります▼ Ｆ＿７▲数式、化学式、表等があります▼Ｆ＿８▲数式
、化学式、表等があります▼ Ｆ＿９▲数式、化学式、表等があります▼Ｆ＿１＿０▲
数式、化学式、表等があります▼Ｆ＿１＿１▲数式、化
学式、表等があります▼Ｆ＿１＿２▲数式、化学式、表
等があります▼ Ｆ＿１＿３▲数式、化学式、表等があります▼Ｆ＿１＿
４▲数式、化学式、表等があります▼ Ｆ＿１＿５▲数式、化学式、表等があります▼Ｆ＿１＿
６▲数式、化学式、表等があります▼ Ｆ＿１＿７▲数式、化学式、表等があります▼Ｆ＿１＿
８▲数式、化学式、表等があります▼ Ｆ＿１＿９▲数式、化学式、表等があります▼Ｆ＿２＿
０▲数式、化学式、表等があります▼ Ｆ＿２＿１▲数式、化学式、表等があります▼Ｆ＿２＿
２▲数式、化学式、表等があります▼ Ｆ＿２＿３▲数式、化学式、表等があります▼Ｆ＿２＿
４▲数式、化学式、表等があります▼ Ｆ＿２＿５▲数式、化学式、表等があります▼Ｆ＿２＿
６▲数式、化学式、表等があります▼ Ｆ＿２＿７▲数式、化学式、表等があります▼Ｆ＿２＿
８▲数式、化学式、表等があります▼ Ｆ＿２＿９▲数式、化学式、表等があります▼Ｆ＿３＿
０▲数式、化学式、表等があります▼ Ｆ＿３＿１▲数式、化学式、表等があります▼Ｆ＿３＿
２▲数式、化学式、表等があります▼ （式中、Ｒ＿９はクロロ、ブロモ、Ｃ＿１＿−＿３アル
キルまたはＣ＿１＿−＿４アルコキシを表し、ｍは１、
２または３を表す。） Ｆ＿３＿３▲数式、化学式、表等があります▼Ｆ＿３＿
４▲数式、化学式、表等があります▼Ｆ＿３＿５▲数式
、化学式、表等があります▼Ｆ＿３＿６▲数式、化学式
、表等があります▼Ｆ＿３＿７▲数式、化学式、表等が
あります▼ Ｆ＿３＿８▲数式、化学式、表等があります▼Ｆ＿３＿
９▲数式、化学式、表等があります▼ Ｆ＿４＿０▲数式、化学式、表等があります▼Ｆ＿４＿
１▲数式、化学式、表等があります▼ Ｆ＿４＿２▲数式、化学式、表等があります▼Ｆ＿４＿
３▲数式、化学式、表等があります▼ （ｍは１または２を表す。 ４、ＡがＡ′即ち下記Ａ＿１〜Ａ＿２＿９から選ばれる
化合物から誘導されたカチオン基である、請求項１〜３
のいずれかに記載の化合物。 Ａ＿１　１、３、５−トリ−（２′、２′、６′、６′
−テトラメチルピペリジル−４′）−トリメシン酸トリ
アミドＡ＿２　２、４−ビス−（２′、２′、６′、６
′−テトラメチルピペリジル−４′−アミノ）−６−ク
ロロトリアジンＡ＿３　２、４、６−トリ−（２′、２
′、６′、６′−テトラメチルピペリジル−４′−アミ
ノ）−トリアジン Ａ＿４　ビス−（２′、２′、６′、６′−テトラメチ
ルピペリジル−４′−アミノカルボニルパラフェニレン
）−テレフタル酸ジイミド Ａ＿５　ビス−（２′、２′、６′、６′−テトラメチ
ルピペリジル−４′）−テレフタル酸アミド Ａ＿６　２、４−ビス−（２′、２′、６′、６′−テ
トラメチルピペリジル−４′−アミノ）−キナゾリン Ａ＿７　２、３−ビス−（２′、２′、６′、６′−テ
トラメチルピペリジル−４′−アミノ）−キノクサリン Ａ＿８　１、４−ビス−（２′、２′、６′、６′−テ
トラメチルピペリジル−４′−アミノ）−フタラジン Ａ＿９　２−クロロ−４、６−ビス−（２′、２′、６
′、６′−テトラメチルピペリジル−４′−アミノ）−
ピリミジンＡ＿１＿０　２、５−ジクロロ−４、６−ビ
ス−（２′、２′、６′、６′−テトラメチルピペリジ
ル−４′−アミノ）−ピリミジンＡ＿１＿１　２−フル
オロ−５−クロロ−４、６−ビス−（２′、２′、６′
、６′−テトラメチルピペリジル−４′−アミノ）−ピ
リミジン Ａ＿１＿２　２、４、６−トリ−（２′、２′、６′、
６′−テトラメチルピペリジル−４′−アミノ）−ピリ
ミジン Ａ＿１＿３　２、４、６−トリ−（２′、２′、６′、
６′−テトラメチルピペリジル−４′−アミノ）−５−
クロロピリミジンＡ＿１＿４▲数式、化学式、表等があ
ります▼ Ａ＿１＿５▲数式、化学式、表等があります▼ Ａ＿１＿６▲数式、化学式、表等があります▼ Ａ＿１＿７▲数式、化学式、表等があります▼ Ａ＿１＿８▲数式、化学式、表等があります▼ Ａ＿１＿９▲数式、化学式、表等があります▼ Ａ＿２＿０▲数式、化学式、表等があります▼ Ａ＿２＿１▲数式、化学式、表等があります▼ Ａ＿２＿２▲数式、化学式、表等があります▼ Ａ＿２＿３ビス−（１、２、２、６、６−ペンタメチル
ピペリジル−４）−テレフタル酸アミド Ａ＿２＿４ビス−（１、２、２、６、６−ペンタメチル
ピペリジル−４）−イソフタル酸アミド Ａ＿２＿５▲数式、化学式、表等があります▼ Ａ＿２＿６▲数式、化学式、表等があります▼ Ａ＿２＿７▲数式、化学式、表等があります▼ Ａ＿２＿８▲数式、化学式、表等があります▼ Ａ＿２＿９▲数式、化学式、表等があります▼ 上記においてＲ＿３は２、２、６、６−テトラメチルピ
ペリジル−４−を表し、Ｒ＿４は式（ｂ） ▲数式、化学式、表等があります▼（ｂ） の基を表し、Ｒ＿５は式（ｃ） ▲数式、化学式、表等があります▼（ｃ） （式中、Ｙは−＾＊Ｎ−ＣＯ−を表す） の基を表し、Ｒ＿５′は式（ｃ）においてＹが−＾＊Ｃ
Ｏ−Ｎ−である基を表し、ここで＾＊を付した原子がピ
ペリジル基に結合しているものとし、Ｒ＿６は式（ｄ）
▲数式、化学式、表等があります▼（ｄ） の基を表し、Ｒ＿７は式（ｅ） ▲数式、化学式、表等があります▼（ｅ） の基を表す。 ５、式（ I ）の化合物を基材に適用することを含む、
基材の着色方法。[Claims] 1. Salt F_n・A (I) represented by the following formula (I) In the above formula, F has 1 to 4 acid groups and is a residue of an anionic dye that does not contain metal. , n represents 1 to 2, and A represents 1 to 2.
Represents a group containing four sterically hindered amine groups and at least n ammonium or immonium groups. 2, F is F′, that is, an azo series, a phthalocyanine series, an anthraquinone series, a perylene series, an indigo series, a thioindigo series,
Derived from non-metallized dyes containing acid groups of the perinone series, quinacridone series, dioxazine series, isoindoline series, isoisotrinones series, diketopyrrole series or pyrrole series, in particular of the azo, phthalocyanine, indigo, anthraquinone, dioxazine and isoisotrinon series 2. The compound according to claim 1, which is a 3. The compound according to claim 1 or 2, wherein F is F'', that is, a compound of the following formulas F_1 to F_4_3. There are mathematical formulas, chemical formulas, tables, etc. ▼ F_4 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ F_5 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ F_6 There are ▼F_8▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_9▲There are mathematical formulas, chemical formulas, tables, etc.▼F_1_0▲
There are mathematical formulas, chemical formulas, tables, etc.▼F_1_1▲There are mathematical formulas, chemical formulas, tables, etc.▼F_1_2▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_1_3▲There are mathematical formulas, chemical formulas, tables, etc.▼F_1_
4▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_1_5▲There are mathematical formulas, chemical formulas, tables, etc.▼F_1_
6▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_1_7▲There are mathematical formulas, chemical formulas, tables, etc.▼F_1_
8▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_1_9▲There are mathematical formulas, chemical formulas, tables, etc.▼F_2_
0▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_2_1▲There are mathematical formulas, chemical formulas, tables, etc.▼F_2_
2▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_2_3▲There are mathematical formulas, chemical formulas, tables, etc.▼F_2_
4▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_2_5▲There are mathematical formulas, chemical formulas, tables, etc.▼F_2_
6▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_2_7▲There are mathematical formulas, chemical formulas, tables, etc.▼F_2_
8▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_2_9▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_
0▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_3_1▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_
2▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_9 represents chloro, bromo, C_1_-_3 alkyl or C_1_-_4 alkoxy, m is 1,
Represents 2 or 3. ) F_3_3▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_
4▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_5▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_6▲There are mathematical formulas, chemical formulas, tables, etc.▼F_3_7▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_3_8▲Mathematical formulas, chemical formulas, There are tables etc. ▼F_3_
9▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_4_0▲There are mathematical formulas, chemical formulas, tables, etc.▼F_4_
1▲There are mathematical formulas, chemical formulas, tables, etc.▼ F_4_2▲There are mathematical formulas, chemical formulas, tables, etc.▼F_4_
3▲There are mathematical formulas, chemical formulas, tables, etc.▼ (m represents 1 or 2. 4. Claims 1 to 3, in which A is A', that is, a cationic group derived from a compound selected from A_1 to A_2_9 below.
A compound according to any one of. A_1 1, 3, 5-tri-(2', 2', 6', 6'
-tetramethylpiperidyl-4')-trimesic acid triamide A_2 2,4-bis-(2',2',6',6
'-Tetramethylpiperidyl-4'-amino)-6-chlorotriazine A_3 2,4,6-tri-(2',2
',6',6'-Tetramethylpiperidyl-4'-amino)-triazine A_4 Bis-(2',2',6',6'-tetramethylpiperidyl-4'-aminocarbonylparaphenylene)-terephthalic acid Diimide A_5 Bis-(2',2',6',6'-tetramethylpiperidyl-4')-terephthalic acid amide A_6 2,4-bis-(2',2',6',6'-tetramethyl Piperidyl-4'-amino)-quinazoline A_7 2,3-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-quinoxaline A_8 1,4-bis-(2' , 2', 6', 6'-tetramethylpiperidyl-4'-amino)-phthalazine A_9 2-chloro-4,6-bis-(2', 2', 6
',6'-tetramethylpiperidyl-4'-amino)-
Pyrimidine A_1_0 2,5-dichloro-4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-pyrimidine A_1_1 2-fluoro-5-chloro-4,6 -Bis-(2', 2', 6'
, 6'-tetramethylpiperidyl-4'-amino)-pyrimidine A_1_2 2,4,6-tri-(2',2',6',
6'-tetramethylpiperidyl-4'-amino)-pyrimidine A_1_3 2,4,6-tri-(2',2',6',
6'-tetramethylpiperidyl-4'-amino)-5-
Chloropyrimidine A_1_4 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_1_5 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_1_6 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_1_7 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_1_8 ▲ Mathematical formulas, There are chemical formulas, tables, etc.▼ A_1_9▲There are mathematical formulas, chemical formulas, tables, etc.▼ A_2_0▲There are mathematical formulas, chemical formulas, tables, etc.▼ A_2_1▲There are mathematical formulas, chemical formulas, tables, etc.▼ A_2_2▲There are mathematical formulas, chemical formulas, tables, etc. ▼ A_2_3 Bis-(1,2,2,6,6-pentamethylpiperidyl-4)-terephthalic acid amide A_2_4 Bis-(1,2,2,6,6-pentamethylpiperidyl-4)-isophthalic acid amide A_2_5 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_2_6 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_2_7 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_2_8 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ A_2_9 ▲ Numerical formulas, chemical formulas, tables, etc. etc.▼ In the above, R_3 represents 2,2,6,6-tetramethylpiperidyl-4-, R_4 represents the group of formula (b) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(b), and R_5 represents the group of formula (c) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(c) (In the formula, Y represents -^*N-CO-), and R_5' represents the group where Y is - in formula (c). ^*C
Represents a group that is O-N-, where the atom with ^* is bonded to the piperidyl group, and R_6 is the formula (d)
▲There are mathematical formulas, chemical formulas, tables, etc.▼(d) represents the group, and R_7 represents the group of formula (e) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(e). 5. applying a compound of formula (I) to a substrate,
How to color the base material.
JP2263215A 1989-10-03 1990-10-02 New pigment Expired - Fee Related JP2956907B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3932913,5 1989-10-03
DE3932913 1989-10-03

Publications (2)

Publication Number Publication Date
JPH03126768A true JPH03126768A (en) 1991-05-29
JP2956907B2 JP2956907B2 (en) 1999-10-04

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CH (1) CH680367A5 (en)
DE (1) DE4030520B4 (en)
FR (1) FR2652585B1 (en)
GB (1) GB2236536B (en)
HK (1) HK70795A (en)
IT (1) IT1242001B (en)
SG (1) SG90648G (en)

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FR2652585A1 (en) 1991-04-05
DE4030520A1 (en) 1991-04-11
GB2236536A (en) 1991-04-10
HK70795A (en) 1995-05-19
GB9021440D0 (en) 1990-11-14
IT1242001B (en) 1994-02-02
CH680367A5 (en) 1992-08-14
IT9048328A0 (en) 1990-10-02
GB2236536B (en) 1992-07-22
JP2956907B2 (en) 1999-10-04
IT9048328A1 (en) 1992-04-02
FR2652585B1 (en) 1997-10-17
SG90648G (en) 1995-09-01

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