CN1146642C - 适用于光学应用的具有低雾度值的热塑性组合物 - Google Patents
适用于光学应用的具有低雾度值的热塑性组合物 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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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
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Abstract
本发明公开了适用于光学应用的具有低雾度值的热塑性模塑组合物。该组合物含选自以下组分的树脂组分:(i)聚碳酸酯树脂和聚己酸内酯的均相共混物和(ii)共聚(碳酸酯-内酯)嵌段或无规共聚物,以及还含黑素,其用量相对每百份(重量)的树脂组分为0.1-1.0份。
Description
技术领域
本发明涉及热塑性模塑组合物,更具体而言,涉及含有黑素的适用于生产光学透镜的具有低雾度值的组合物。
背景技术
最近数年,人们已经越来越注意到保护眼睛和皮肤不受人工和自然光源发射光的辐射的重要性。例如,认为眼睛长时间地暴露在反射的太阳紫外线辐射中,将导致形成白内障和一般组织损伤。此外,也注意到保护包装材料不受此类辐射以减少辐射可能导致的材料去稳定作用、降解、腐烂或其它不合需要的影响的重要性。
多种商品光学滤光镜致力于应付由这些辐射环境造成的威胁。这样的光学吸收系列制品包括太阳镜、隐形眼镜、航空器和汽车窗口、焊接眼镜和其它。
在太阳镜的情况下,目前采用两种常规类型的材料作为实际的吸收组分。沉积在塑料镜片基底上的金属膜是非常有效的防晒材料,其提供电磁波从紫外线到近红外线波长范围的宽带衰减。然而,这种太阳镜装置有两个缺点。第一是需要除了制造基本塑料镜片以外的制造步骤,和,第二,从后面入射的光和直接反射进眼睛的光引起了新问题,所以需要进一步改进制造方法。
染料和颜料构成第二类常用的光学吸收体。这些分子或聚合成分或是作为薄膜沉积或是分散在塑料基体中。美国专利4 157 892具体描述了一种使吸水塑料着色的方法。这类装置的缺点是染料和颜料通常不能充分吸收超过所有紫外线波长的射线,并且其倾向于光降解。对于有机染料和颜料光降解作用特别普遍。
已知黑素可用作提供紫外线、可见光和近红外线吸收性能以保护眼睛的颜料。相关技术包括美国专利4 698 374,它公开了一种需要固体透明基底和黑素的用于防射线的光学镜片体系。在实施例中,通过黑素前体与单体同时进行自由基聚合将黑素颜料引入镜片体系中。此公开的单体是二甘醇二(烯丙基碳酸酯)、苯乙烯和甲基丙烯酸甲酯。
美国专利5 116 884和5 047 447也是相关技术,它们公开了含黑素的亲水的隐形眼镜。黑素是通过将其粘附在镜片表面或将其掺合在镜片基体中引入镜片中的。美国专利5 036 115公开了基于二甘醇二烯丙基碳酸酯的含黑素的防辐射的眼镜及其制备过程。
发明内容
本发明涉及新的含有聚碳酸酯树脂、聚己酸内酯和黑素的模塑组合物。以低雾气度为特征的本组合物适用于透镜制备和窗用玻璃应用中。此外,本发明体系的抗冲击性能完全比得上聚碳酸酯的性能。这种优越的抗冲击性能使本发明的组合物区别于基于烯丙基树脂和基于玻璃的相应的组合物。
本发明具体涉及热塑性模塑组合物,其包含:
(A)选自以下组分的树脂组分
(i)聚碳酸酯树脂和聚己酸内酯的均相共混物和
(ii)共聚(碳酸酯-内酯)嵌段或无规共聚物,和
(B)黑素,其用量相对每百份(重量)的(A)为0.1-1.0份。
上述的热塑性模塑组合物,其中所说的(ii)含有1-50mol%符合下式结构的单元
本发明的热塑性模塑组合物含有聚碳酸酯树脂(简称“PC”)、聚己酸内酯(简称“PCL”)和黑素。优选地,此组合物含有至少约5%的聚己酸内酯(本文中所有的百分数都是指相对聚碳酸酯和PCL的总重量的百分数)和足够量的能使组合物实际上没有雾气的黑素。更优选地,组合物含有约5至35%的PCL、95至65%的聚碳酸酯和每百份树脂约0.1至1.0份(pphr)黑素。最优选地,组合物含有10至25%的PCL、75至90%的PC和0.1至0.5pphr的黑素。
本发明中的聚己酸内酯是一种聚合的树脂,其重均分子量最大约250 000、优选25 000至150 000和最优选30 000至100 000,其分子结构含有符合下式的单元
合适的PCL是市售的部分结晶的树脂,如来自联合碳化物公司的名为Tone聚合物的P-767和P-787。PCL优选具有减小的粘度(30℃下于100ml苯中用0.2g聚合物测定)即约0.1至1.5,更优选约0.5至0.9。
PCL是通过ε-己内酯的开环反应形成的线型聚酯。
在本发明范围内的芳香族聚碳酸酯是均聚碳酸酯、共聚碳酸酯支链聚碳酸酯和它们的混合物。通常聚碳酸酯的重均分子量为10 000至200 000和优选20 000至80 000,并且它们于300℃按ASTM D-1238的熔体流速为约1至约65g/10min和优选约2至15g/10min。它们可以例如由碳酸衍生物如光气和二羟基化合物以公知的两相界面法通过缩聚制得(参见德国公开说明书2 063 050、2 063 052、1 570703、2 211 956、2 211 957、2 248 817、法国专利1 561 518和H.Schnell的专著“聚碳酸酯化学和物理”(内部科学出版社,纽约,1964),都在此引入作为参考)。
在本文中,适用于制备本发明聚碳酸酯的二羟基化合物符合式(1)或(2)的结构
其中
A表示含1-8个碳原子的亚烷基、含2-8个碳原子的(1,1-)亚烷基(alkylidene)、含5-15个碳原子的环亚烷基、含5-15个碳原子的(1,1-)环亚烷基(cycloalkylidene)、羰基、氧原子、硫原子、-SO-、-SO2-或符合下式结构的基团
e和g都表示数0-1;Z表示F、Cl、Br或C1-C4烷基并且如果一个芳基上有多个Z基团,则它们可以相同或互相不同;d表示0-4的整数和f表示0-3的整数。
二酚化合物中可用于本发明实施中的有对苯二酚、间苯二酚、二(羟基苯基)烷烃、二(羟基苯基)醚、二(羟基苯基)酮、二(羟基苯基)亚砜、二(羟基苯基)硫醚、二(羟基苯基)砜、α,α-二(羟基苯基)二异丙基苯以及它们的核被烷基化的化合物。已有文献描述了这些和其它合适的芳香族二羟基化合物,例如:美国专利3 028356、2 999 835、3 148 172、2 991 273、3 271 367和2 999 846,这些文献都在此引入作为参考。
其它合适的二酚的实例2,2-二(4-羟基苯基)丙烷(双酚A)、2,4-二(4-羟基苯基)-2-甲基丁烷、1,1-二(4-羟基苯基)环己烷、α,α’-二(4-羟基苯基)-p-二异丙基苯、2,2-二(3-甲基-4-羟基苯基)丙烷、2,2-二(3-氯-4-羟基苯基)丙烷、二(3,5-二甲基-4-羟基苯基)甲烷、2,2-二(3,5-二甲基-4-羟基苯基)丙烷、二(3,5-二甲基-4-羟基苯基)硫醚、二(3,5-二甲基-4-羟基苯基)亚砜、二(3,5-二甲基-4-羟基苯基)砜、二羟基二苯甲酮、2,4-二(3,5-二甲基-4-羟基苯基)环己烷、α,α’-二(3,5-二甲基-4-羟基苯基)-p-二异丙基苯、2,2,4-三甲基环己基-1,1-二酚和4,4’-磺酰基二酚。
特别优选的芳香族二酚的实例有是2,2-二(4-羟基苯基)丙烷、2,2-二(3,5-二甲基-4-羟基苯基)丙烷、2,2,4-三甲基环己基-1,1-二苯酚和1,1-二(4-羟基苯基)环己烷。
最优选的二酚是2,2-二(4-羟基苯基)丙烷(双酚A)。
本发明的聚碳酸酯可以在其结构中需要有衍生自一种或多种合适的二酚的单元。
本发明另外的实施方案以下述组合物代表,其中树脂组分含有共聚(碳酸酯-内酯)嵌段或无规共聚物。在本发明的这个实施方案中,共聚物含有1-50mol%的符合下式结构的单元
这种共聚碳酸酯的制备是本领域熟知的。
在本发明的实施中适用的树脂包括酚酞基聚碳酸酯、共聚碳酸酯和三聚碳酸酯,如美国专利3 036 036和4 210 741所描述的,这两篇专利都在此引入作为参考。
也可以通过缩合少量如0.05-2.0mol%(相对二酚)的多羟基化合物将本发明的聚碳酸酯支化。
有关文献已经描述了此类聚碳酸酯,例如德国公开说明书1 570533、2 116 974、2 113 374、英国专利885 442、1 079 821和美国专利3 544 514。以下是一些可以用于此目的的多羟基化合物的例子:间苯三酚、4,6-二甲基-2,4,6-三(4-羟基苯基)庚烷、1,3,5-三(4-羟基苯基)苯、1,1,1-三(4-羟基苯基)乙烷、三(4-羟基苯基)苯基甲烷、2,2-二[4,4-(4,4’-二羟基联苯)]环己基丙烷、2,4-二(4-羟基-1-异亚丙基)酚、2,6-二(2’-二羟基-5’-甲基苄基)-4-甲基酚、2,4-二羟基苯甲酸、2-(4-羟基苯基)-2-(2,4-二羟基苯基)丙烷和1,4-二(-4,4’-二羟基三苯基甲基)苯。一些其它的多官能化合物是2,4-二羟基苯甲酸、苯均三酸、氰尿酰氯和3,3-二(4-羟基苯基)-2-氧代-2,3-二氢吲哚。
除了上述提及的缩聚法以外,其它制备本发明聚碳酸酯的方法是均相缩聚和酯转移。合适的方法在下列文献中有公开,所述文献在此引入作为参考:美国专利3 028 365、2 999 846、3 153 008和2 991273。
优选的用于制备聚碳酸酯的方法是界面缩聚法。
可以使用其它形成本发明聚碳酸酯的合成方法,如美国专利3 912688所公开的,该专利在此引入作为参考。
合适的聚碳酸酯树脂是市售的,例如Makrolon FCR、Makrolon CD2005、Makrolon 2600、Makrolon 2800和Makrolon 3100,它们都是基于均聚碳酸酯树脂的二酚,它们各自的分子量不同,并且其特征在于它们的按ASTM D-1238的熔流指数(MFR)分别为约16.5-24、13-16、7.5-13.0和3.5-6.5g/10min。这些是Pennsylvania,Pittsburgh的Bayer公司的产品。
在本发明的实施中适用的聚碳酸酯树脂是公知的,并且其结构和制备方法都已经公开,例如美国专利3 030 331、3 169 121、3 395119、3 729 447、4 255 556、4 260 731、4 369 303和4 714 746,这些文献都在此引入作为参考。
对于本发明的目的,黑素的定义和分类如名为“黑素”(R.A.Nicolaus,Hermann 1968年出版,115,Boulevard Saint-Germain,Paris,France一书中所述,该书在此全部引入作为参考)。如Nicolaus所定义的,黑素构成一类广泛分布于动物和蔬菜界的颜料。尽管在希腊语中名称黑素意味着黑色,但不是所有作为颜料的黑素都是黑色,而是可以从棕色至黄色不同。可以如下所示将黑素分类:
正常黑素,其衍生自前体酪氨酸(1):
棕黑素,作为其前体其具有酪氨酸和半胱氨酸(2):
异黑素(allomelanins),其含义是其它的黑素,它们是由不含氮的前体、主要是儿茶酚和1,8二羟基萘形成的。从Merck Index(10版,1983)中的827页上的专著No.5629发现更多关于黑素的信息,该文献在此引入作为参考。醌是异黑素合成中常用的中间体。黑素的合成自发发生。此外,也可以工业或在实验室合成黑素。例如在下面的文章中发现合成生产的儿茶酚黑素和DOPA黑素的例子:Froncisz,W.,Sama,T.,Hyde,James S.Arch.生物化学生物物理学“Copper(2+)ion Probe of Metal-ion Binding Sites in MelaninUsing Electron Paramagnetic Resonance Spectroscopy.”I.合成的黑素(1980,202(1),289-303)。此文章在此引入作为参考。Froncisz等人的文章公开了儿茶酚黑素,它是以下述方法生产的:
儿茶酚黑素。用氢氧化铵将15g儿茶酚在3升去离子水中的溶液的pH调节至8,然后将空气鼓泡通过搅拌的溶液,进行4天。加入浓盐酸使pH值为2,将得到的黑素沉淀,接着用稀盐酸洗涤,用去离子水透析几天以除去氢离子和氯离子。通过真空中在P2O5上干燥等份试样并称重估算黑素悬浮液的浓度。通过将10ml 10-3M的铁氰化钾加入30mg黑素中并且保温约10分钟制得氧化的儿茶酚黑素。然后将悬浮液降级使用,用去离子水洗涤两次,悬浮在5ml去离子水中。
可以在美国专利5 047 447和其中给出的文献中发现关于合适的黑素的制备的另外的信息,这些文献都在此引入作为参考。
本发明的组合物的制备是常规的,可以用复配热塑性模塑组合物领域公知的常规设备和常规工艺过程来实施。
本发明的组合物可以用于光学应用和防辐射,通常包括太阳镜和滤器。
具体实施方式
通过下述实施例进一步说明本发明,但不是进行限制,其中,除非特别说明,否则所有的份数和百分数都是以重量计。
实施例
实验
制备本发明所述的组合物并且测定它们的性能。PCL的模制品是不透明的且只含有PCL和黑素的组合物不适用于必需透明的场合。
如下表所示的制得并估算的组合物包含Tone 767,它是联合碳化物公司的PCL产品,特征为重均分子量为50 000g/mol的一种树脂)。聚碳酸酯是Bayer公司的产品Makrolon 2408,它是基于双酚A且熔流指数为约22g/10min的均聚物。下述实施例中所用的黑素是通过儿茶酚在乙腈中氧化制备的儿茶酚黑素。下表总结了结果。
A | B | C | D | |
聚碳酸酯,重量百分数(wt.%) | 100 | 100 | 85 | 85 |
聚己酸内酯wt.% | 0 | 0 | 15 | 15 |
黑素,pphr | 0 | 0.25 | 0 | 0.25 |
熔体流速 | 22.7 | 23.5 | 48.8 | 45.7 |
黄度指数* | 1.95 | 52.26 | 3.92 | 57.92 |
雾度% | 0.37 | 5.01 | 1.01 | 1.89 |
总透光度% | 90.62 | 55.02 | 89.80 | 52.37 |
高速冲击** | 48.2 | 45.4 | 44.5 | 44.6 |
*根据ASTM D 1925,样品厚度75mils。
**"4×1/8"圆盘;高速冲击按ASTM D-3763-86@50%湿度,23℃。
根据ASTM D 1238测定的熔体流速为约20g/10min。
结果表明黑素能有效地使得组合物适用于光学应用。
尽管为了说明的目的,上文已经对本发明进行了详细的描述,但是应当理解,这些详细的描述只是为了此目的,在除了权利要求所限制的不脱离本发明的精神和范围内,本领域技术人员可以由此作出改变。
Claims (10)
1.热塑性模塑组合物,其包含:
(A)选自以下组分的树脂组分
(i)聚碳酸酯树脂和聚己酸内酯的均相共混物和
(ii)共聚(碳酸酯-内酯)嵌段或无规共聚物,和
(B)黑素,其用量相对每百份(重量)的(A)为0.1-1.0份。
2.权利要求1所述的热塑性模塑组合物,其中所说的(ii)含有1-50mol%符合下式结构的单元
3.权利要求1所述的热塑性模塑组合物,其中共混物含有相对聚碳酸酯和聚己酸内酯的总重约5-35%的聚己酸内酯。
4.权利要求3所述的热塑性模塑组合物,其中聚己酸内酯的重均分子量为25 000-150 000。
5.权利要求3所述的热塑性模塑组合物,其中聚碳酸酯的重均分子量为10 000-200 000。
6.权利要求1所述的热塑性模塑组合物,其中黑素是正常黑素。
7.权利要求1所述的热塑性模塑组合物,其中黑素是棕黑素。
8.权利要求1所述的热塑性模塑组合物,其中黑素是儿茶酚黑素。
9.权利要求1所述的热塑性模塑组合物,其中黑素的用量为0.1-0.5pphr。
10.权利要求1所述的热塑性模塑组合物,其中共混物含有相对聚碳酸酯和聚己酸内酯的总重约10-25%的聚己酸内酯。
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CN103465418B (zh) * | 2013-09-10 | 2016-04-13 | 上海康耐特光学股份有限公司 | 一种防蓝光树脂镜片的制造方法及产品 |
CN107298838A (zh) * | 2016-04-15 | 2017-10-27 | 江南大学 | 一种聚碳酸酯组合物及制备方法 |
CN106236723A (zh) * | 2016-09-17 | 2016-12-21 | 佛山市弘泰药物研发有限公司 | 一种罗氟司特口崩片及其制备方法 |
TW201903017A (zh) * | 2017-05-31 | 2019-01-16 | 鴻海精密工業股份有限公司 | 眼用鏡片及其製備方法 |
JOP20200332A1 (ar) * | 2018-06-21 | 2020-12-20 | Steven Baranowitz | مادة مقاومة للصدمات |
JP7402449B2 (ja) * | 2019-08-29 | 2023-12-21 | 国立研究開発法人日本原子力研究開発機構 | 樹脂組成物及び遮光レンズの製造方法 |
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US5116884A (en) * | 1984-06-08 | 1992-05-26 | Photoprotective Technology Incorporated | Melanin hydrophilic contact lenses |
US5112883A (en) * | 1984-06-08 | 1992-05-12 | Photoprotective Technologies Incorporated | Medium incorporating melanin as an absorbing pigment against electromagnetic radiation |
US5047447A (en) * | 1984-06-08 | 1991-09-10 | Photoprotecive Technologies Incorporated | Medium incorporating melanin as an absorbing pigment for protection against electromagnetic radiation |
US5036115A (en) * | 1984-06-08 | 1991-07-30 | Photoprotective Technologies, Inc. | Optical lens system incorporating melanin as an absorbing pigment for protection against electromagnetic radiation |
US4698347A (en) * | 1985-06-10 | 1987-10-06 | Eli Lilly And Company | Octahydro-oxazolo[4,5-g]quinolines derivatives and decahydro quinoline intermediates and their use as dopamine D-2 agonists |
IT1255146B (it) * | 1992-05-08 | 1995-10-20 | Intercast Europ | Melanina sintetica purificata particolarmente per dispositivi ottici abassa diffusione |
US5998520A (en) * | 1997-07-02 | 1999-12-07 | Bayer Corporation | Photochromic compositions having improved fade rate |
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1998
- 1998-12-18 US US09/215,497 patent/US6103777A/en not_active Expired - Fee Related
-
1999
- 1999-12-09 BR BR9916319-5A patent/BR9916319A/pt not_active IP Right Cessation
- 1999-12-09 AU AU21710/00A patent/AU2171000A/en not_active Abandoned
- 1999-12-09 EP EP99966078A patent/EP1165691B1/en not_active Expired - Lifetime
- 1999-12-09 CA CA002355056A patent/CA2355056A1/en not_active Abandoned
- 1999-12-09 JP JP2000589626A patent/JP2002533516A/ja active Pending
- 1999-12-09 ES ES99966078T patent/ES2209548T3/es not_active Expired - Lifetime
- 1999-12-09 DE DE69912006T patent/DE69912006T2/de not_active Expired - Fee Related
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- 1999-12-09 WO PCT/US1999/029193 patent/WO2000037563A1/en not_active Application Discontinuation
- 1999-12-09 CN CNB998145629A patent/CN1146642C/zh not_active Expired - Fee Related
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2002
- 2002-06-27 HK HK02104783.1A patent/HK1043143A1/zh unknown
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EP1165691A1 (en) | 2002-01-02 |
ES2209548T3 (es) | 2004-06-16 |
HK1043143A1 (zh) | 2002-09-06 |
EP1165691B1 (en) | 2003-10-08 |
AU2171000A (en) | 2000-07-12 |
DE69912006T2 (de) | 2004-08-12 |
CA2355056A1 (en) | 2000-06-29 |
BR9916319A (pt) | 2001-08-14 |
JP2002533516A (ja) | 2002-10-08 |
US6103777A (en) | 2000-08-15 |
DE69912006D1 (de) | 2003-11-13 |
KR20010093183A (ko) | 2001-10-27 |
CN1330689A (zh) | 2002-01-09 |
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