CN1481416A - 着色塑料或聚合物染料颗粒的制备 - Google Patents
着色塑料或聚合物染料颗粒的制备 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/347—Anthraquinone acridones
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- 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
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Abstract
本发明涉及一种着色塑料或聚合物染料颗粒的制备方法,其特征在于该方法包含将一种高分子量有机材料与一种彩色学方面有效量的至少一种式(1)的染料混合,其中:R1是氢、羟基或基团-NHCO-R6,其中R6是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,R2是氢、羟基或基团W-R7,其中W是-NHCO-或-S-,R7是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,R3是氢,R4是氢或羟基,R5是氢,或R3和R4合在一起形成下式的基团:其中环A和B可独立地进一步带有取代基。
Description
技术领域
本发明涉及着色塑料或聚合物染料颗粒的制备方法。
背景技术
用染料对塑料进行本体染色的各种方法是已知的。但是,已经确定,至今所用的染料不总是完全符合最高的要求,尤其在耐热耐光坚牢度方面。因此,需要有能产生耐光,尤其耐热耐光的坚牢着色性且显示出良好的一般坚牢度的新的着色方法。
现已令人惊奇地发现,本发明的着色方法基本上符合上面指出的标准。
发明内容
因此本发明提供一种着色塑料或聚合物染料颗粒的制备方法,其特征在于该方法包含将一种高分子量有机材料与一种彩色学方面有效量的至少一种式(1)的染料混合:其中:
R1是氢、羟基或基团-NHCO-R6,其中R6是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,
R2是氢、羟基或基团W-R7,其中W是-NHCO-或-S-,R7是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,
R3是氢,
R4是氢或羟基,
R5是氢,或R3和R4合在一起形成下式的基团:其中环A和B可独立地进一步带有取代基。
环A和B的有用的任选取代基包括特别是卤素、C1-C4烷基和C1-C4烷氧基。可以存在1个以上的取代基。
R6和R7定义中的C1-C6烷基包括例如甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、叔戊基(1,1-二甲基丙基)、1,1,3,3-四甲基丁基、己基、1-甲基戊基、新戊基、环戊基、环己基和有关的异构体。
作为苯基上的取代基或作为环A和B上的取代基的C1-C4烷基是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基。
作为环A和B上的取代基的C1-C4烷氧基是例如甲氧基、乙氧基、丙氧基和丁氧基。
卤素是溴、碘以及尤其氯。
W-R7定义中的C1-C6硫烷基是例如甲硫基、乙硫基、丙硫基或丁硫基。
特别优选的是式(2)和(7)的染料。
按照本发明所用的染料是已知的,或可通过通常已知的方法类似于已知化合物制备。
按照本发明使用的式(1)的染料例如可通过下述方法制备,使下式的化合物:式中A、R3、R4和R5各自的定义按式(1)中所述,R8取代基之一是-NH2,其它是R1或R2,在氯磺酸中发生闭环反应生成下式的化合物:随后使其与羰基氯反应生成式(1)的染料。
式(50)的化合物是已知的,或可通过通常已知的方法类似于已知化合物制备。
高分子量有机物质用式(1)的染料进行染色的方法例如可通过用辊磨机或混合或研磨设备将所述染料掺进这些物质中,从而使染料溶解或微细分散在该高分子量物质中。然后用惯常的方式,例如通过压延、压制、挤塑、展涂、纺丝、流延或注塑将高分子量有机材料与掺混的染料一起进行加工,从而使该染了色的材料具有其最终形状。染料的掺混也可在实际加工步骤之前直接进行,例如通过将固体例如粉末状染料与颗粒状或粉末状高分子量有机材料以及任选的其它物质例如各种添加剂同时直接计量加入到挤出机的入口区,在挤出机中混合后立即加工。但是,一般而言,先将染料掺入到高分子量有机材料中是优选的,因为这样可得到更加均匀的染色物质。
通常希望在成形之前将增塑剂加入到高分子量化合物中以便生产出非刚性制品或减少其脆性。有用的增塑剂包括例如磷酸、邻苯二甲酸或癸二酸的酯。在本发明的方法中,增塑剂可在着色剂加入之前或之后加入到聚合物中。为了得到不同的色相,除了式(1)的染料外,还可以往该高分子量有机物质中加入任何所需量的颜料或其它着色剂,以及任选的其它添加剂,例如填料或催干剂。
优选的是尤其纤维形式的着色热塑性塑料。按照本发明可着色的优选的高分子量有机材料一般是介电常数≥2.5的聚合物,尤其聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯甲酯(PMMA)、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈共聚物(SAN)或丙烯腈/丁二烯/苯乙烯(ABS)。特别优选的是聚酯和聚酰胺。更特别优选的是由对苯二甲酸和二醇尤其乙二醇缩聚得到的线型芳族聚酯,或对苯二甲酸与1,4-二(羟甲基)环己烷的缩合产物,例如聚对苯二甲酸乙二醇酯(PET)或聚对苯二甲酸丁二醇酯(PBTP);聚碳酸酯,例如由α,α-二甲基-4,4′-二羟基二苯甲烷与光气形成的聚碳酸酯;或基于聚氯乙烯的聚合物或聚酰胺例如尼龙6或尼龙66。
本发明还提供一种塑料或聚合物染料颗粒的三原色染色方法,其特征在于该方法包含将至少一种式(2)、(3)、(4)、(5)或(6)的蓝染料,至少一种式(7)、(8)、(9)、(10)、 (24) 或的红染料和下式的黄染料掺混到塑料或聚合物染料颗粒中。
式(11)至(26)的染料是已知的,或可通过本身已知的方法类似于已知化合物制备。
三色现象(trichromism)是适当选择的黄或橙染料、红染料和蓝染料的添加的颜色混合物,从而任何所需的可见光谱色相都可通过适当选择各染料组分的含量比来调配。
按照本发明的三原色方法的一个优选实施方案的特征在于式(2)的蓝染料与式(7)的红染料和式(26)的黄染料一起使用。
按照本发明的三原色方法的另一个优选实施方案的特征在于式(2)的蓝染料与式(14)的红染料和式(26)的黄染料一起使用。
按照本发明使用的染料给予上述材料,尤其聚酯和聚酰胺材料以具有良好用户坚牢度,尤其非常好的耐光度的强水平色相。
下列实施例说明本发明。除非另有说明,否则份额和百分率均指重量。温度以摄氏度表示。正象克与立方厘米有关那样,重量份与体积份有关。
实施例1
往反应器中装入145.0重量份浓硫酸和70.0重量份氯磺酸。在25℃加入36.0重量份式(52)的化合物:然后将混合物在25-30℃搅拌2小时。然后将其排放到1500重量份冰水中,抽吸滤出沉淀物,洗涤至中性并干燥。
12.9重量份式(53)的化合物加入到85重量份硝基苯中,将混合物加热到130-140℃。用约30分钟的时间在130-140℃逐滴加入6.6重量份间甲苯甲酰氯在12重量份硝基苯中的溶液。然后将混合物搅拌1小时。将反应混合物冷却至20-40℃,直接或用甲醇稀释后过滤,过滤后的残留物用甲醇和水洗涤,然后干燥。这提供了14.8重量份式(2)的染料:该染料将聚酯染成一种耐光的蓝色调。
实施例2
1200.00g聚酯切片(PET Arnite D04-300,DSM)在130℃预干燥4小时,然后与0.24g式(7)的染料:在每分钟60转的辊筒混合机中混合15分钟直至均匀。所得均匀混合物在25mm直径的双螺杆挤出机(购自Collin,D-85560 Ebersberg)中进行挤出,该挤出机有6个加热区,最高温度275℃,用水骤冷,用Turb Etuve TE 25造粒机(购自MAPAG公司,CH-3001 Bern)造粒,然后在75℃干燥4小时。这提供了红色聚酯切片,具有良好的各方面的坚牢度,尤其非常好的耐光度和耐热耐光度。
实施例3
1200.00g聚酯切片(PET Arnite D04-300,DSM)在130℃预干燥4小时,然后与0.64g式(2)的染料、0.30g式(7)的染料和1.46g式(26)的染料在每分钟60转的辊筒混合机中混合15分钟直至均匀。所得均匀混合物在25mm直径的双螺杆挤出机(购自Collin,D-85560Ebersberg)中进行挤出,该挤出机有6个加热区,最高温度220℃,用水骤冷,用Turb Etuve TE 25造粒机(购自MAPAG公司,CH-3001Bern)造粒,然后在75℃干燥4小时。这提供了红色聚酯切片,具有良好的各方面的坚牢度,尤其非常好的耐光度和耐热耐光度。
实施例4
1200.00g聚酯切片(PET Arnite D04-300,DSM)在130℃预干燥4小时,然后与2.40g式(2)的染料在每分钟60转的辊筒混合机中混合15分钟直至均匀。所得均匀混合物在25mm直径的双螺杆挤出机(购自Collin,D-85560 Ebersberg)中进行挤出,该挤出机有6个加热区,最高温度220℃,用水骤冷,用Turb Etuve TE 25造粒机(购自MAPAG公司,CH-3001 Bern)造粒,然后在75℃干燥4小时。这提供了红色聚酯切片,具有良好的各方面的坚牢度,尤其非常好的耐光度和耐热耐光度。
Claims (5)
1.一种着色塑料或聚合物染料颗粒的制备方法,其特征在于该方法包含将一种高分子量有机材料与一种彩色学方面有效量的至少一种式(1)的染料混合:其中:
R1是氢、羟基或基团-NHCO-R6,其中R6是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,
R2是氢、羟基或基团W-R7,其中W是-NHCO-或-S-,R7是C1-C6烷基或无取代的或被C1-C4烷基-或卤素取代的苯基,
R3是氢,
R4是氢或羟基,
R5是氢,或
R3和R4合在一起形成下式的基团:其中环A和B可独立地进一步带有取代基
4.由权利要求1或2的方法制备的着色塑料或聚合物染料颗粒。
5.按照权利要求1的式(1)的染料用于制备着色塑料或聚合物染料颗粒的用途。
Applications Claiming Priority (2)
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CH25092000 | 2000-12-22 | ||
CH2509/2000 | 2000-12-22 |
Publications (1)
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CN1481416A true CN1481416A (zh) | 2004-03-10 |
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Application Number | Title | Priority Date | Filing Date |
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CNA018209726A Pending CN1481416A (zh) | 2000-12-22 | 2001-12-13 | 着色塑料或聚合物染料颗粒的制备 |
Country Status (9)
Country | Link |
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US (1) | US6923836B2 (zh) |
EP (1) | EP1343840A1 (zh) |
JP (1) | JP3927121B2 (zh) |
KR (1) | KR20040010577A (zh) |
CN (1) | CN1481416A (zh) |
BR (1) | BR0116321A (zh) |
CA (1) | CA2430604A1 (zh) |
MX (1) | MXPA03005623A (zh) |
WO (1) | WO2002051924A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105801887A (zh) * | 2016-04-11 | 2016-07-27 | 浙江纳美新材料股份有限公司 | 一种制备聚合物连续色卡的方法 |
Families Citing this family (4)
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KR20050006132A (ko) * | 2002-03-22 | 2005-01-15 | 시바 스페셜티 케미칼스 홀딩 인크. | 안트라퀴논 염료 |
CN100408640C (zh) * | 2002-03-22 | 2008-08-06 | 西巴特殊化学品控股有限公司 | 蒽醌染料 |
JP2006524282A (ja) | 2003-04-22 | 2006-10-26 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 顔料/染料混合物 |
KR100692787B1 (ko) * | 2006-04-17 | 2007-03-12 | (주)엑셀코리아 | 기능성 화장품 용기 뚜껑 제조 방법 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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US1002066A (en) * | 1911-02-18 | 1911-08-29 | Basf Ag | Vat dye. |
US1690913A (en) * | 1925-10-29 | 1928-11-06 | Grasselli Dyestuff Corp | Manufacture of vat dyestuffs of the anthraquinone-acridone series |
US2031406A (en) * | 1932-01-19 | 1936-02-18 | Gen Aniline Works Inc | Vat dyestuffs of the anthraquinone-2.1(n) benzacridone series |
BE627049A (zh) * | 1962-01-12 | |||
CH401311A (de) * | 1962-03-13 | 1965-10-31 | Ciba Geigy | Verfahren zur Herstellung von wasserunlöslichen, carbonsäureamidgruppenhaltigen Farbstoffen |
DE1278634B (de) * | 1964-02-25 | 1968-09-26 | Basf Ag | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
GB1111895A (en) * | 1966-03-17 | 1968-05-01 | Ici Ltd | Process for the mass coloration of polyesters |
FR1493903A (fr) * | 1965-09-15 | 1967-09-01 | Sandoz Sa | Colorants anthraquinoniques, leur procédé de fabrication et leurs applications |
GB1127704A (en) * | 1966-03-08 | 1968-09-18 | Ici Ltd | Polycyclic dyestuffs containing a 3:4-phthaloylacridone residue |
GB1073367A (en) * | 1966-03-24 | 1967-06-28 | Ici Ltd | Polycyclic dyestuffs |
CH570436A5 (zh) * | 1972-07-07 | 1975-12-15 | Ciba Geigy Ag |
-
2001
- 2001-12-13 JP JP2002553409A patent/JP3927121B2/ja not_active Expired - Fee Related
- 2001-12-13 EP EP01272009A patent/EP1343840A1/en not_active Withdrawn
- 2001-12-13 MX MXPA03005623A patent/MXPA03005623A/es unknown
- 2001-12-13 WO PCT/EP2001/014691 patent/WO2002051924A1/en active Application Filing
- 2001-12-13 BR BR0116321-3A patent/BR0116321A/pt not_active IP Right Cessation
- 2001-12-13 US US10/451,172 patent/US6923836B2/en not_active Expired - Fee Related
- 2001-12-13 CA CA002430604A patent/CA2430604A1/en not_active Abandoned
- 2001-12-13 CN CNA018209726A patent/CN1481416A/zh active Pending
- 2001-12-13 KR KR10-2003-7008128A patent/KR20040010577A/ko not_active Application Discontinuation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105801887A (zh) * | 2016-04-11 | 2016-07-27 | 浙江纳美新材料股份有限公司 | 一种制备聚合物连续色卡的方法 |
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Publication number | Publication date |
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MXPA03005623A (es) | 2003-10-06 |
WO2002051924A1 (en) | 2002-07-04 |
BR0116321A (pt) | 2003-10-14 |
US6923836B2 (en) | 2005-08-02 |
CA2430604A1 (en) | 2002-07-04 |
EP1343840A1 (en) | 2003-09-17 |
KR20040010577A (ko) | 2004-01-31 |
JP3927121B2 (ja) | 2007-06-06 |
JP2004522825A (ja) | 2004-07-29 |
US20040045102A1 (en) | 2004-03-11 |
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