CN1600766A - 氟代醇及其用途 - Google Patents

氟代醇及其用途 Download PDF

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CN1600766A
CN1600766A CNA031014704A CN03101470A CN1600766A CN 1600766 A CN1600766 A CN 1600766A CN A031014704 A CNA031014704 A CN A031014704A CN 03101470 A CN03101470 A CN 03101470A CN 1600766 A CN1600766 A CN 1600766A
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吉沢透
高木祥二
安原尚史
横山秦典
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Daikin Industries Ltd
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Abstract

本发明提供一种由下列通式(1)表示的用于制备一种信息记录介质的含有不高于50ppm蒸发残余物的氟代醇：H(CFR1CF2) nCH2OH (1)，其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F。

Description

氟代醇及其用途
本申请为中国专利申请No.99119085.8的分案申请。
技术领域
本发明涉及制备由通式(1)表示的氟代醇的方法：
      H(CFR1CF2)nCH2OH        (1)
(其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F)，所说氟代醇基本上不含杂质，以及所说氟代醇在包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质的制造中的应用。
背景技术
在有关制备H(CF2CF2)nCH2OH(n＝1，2)的技术中，日本未审查专利公告154707/1979和美国专利第2,559,628号中公开了一种调聚物的混合物，即H(CF2CF2)nCH2OH(n最大为12)，可以通过将甲醇与四氟乙烯在叔丁基辛基过氧化物的存在下进行反应而制备。
但是，即使是对用该方法所获得的调聚物的混合物进行蒸馏纯化，仍有几百个ppm数量级的蒸发残余物不能除去，结果当其被用于包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质，如CD-R和DVD-R的制造时，该信息记录介质的质量由于所说蒸发残余物的影响而不很高。
本发明的目的是提供下列通式(1)的一种氟代醇
     H(CFR1CF2)nCH2OH            (1)
(其中n和R1如前面所定义)，该氟代醇基本上不含杂质如蒸发残余物和紫外吸收物质；一种制备所说氟代醇的方法；所说氟代醇作为溶剂在包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质的制造中的应用；以及一种包含有基板和建立在该基板上的适于激光写和/或读的记录层的信息记录介质。
发明内容
本发明涉及下列的1～20项：
1.一种制备由下列通式(1)表示的氟代醇的方法：
      H(CFR1CF2)nCH2OH            (1)
(其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F)，该方法包括将甲醇与四氟乙烯或六氟丙烯在一种自由基源的存在下反应，其中将反应混合物在一种碱存在下或将所说反应混合物与一种碱接触后进行蒸馏。
2.如上述第1项所定义的制备氟代醇的方法，其中所述的碱是一种具有不高于2的pKb值的物质。
3.如上述第1项所定义的制备氟代醇的方法，其中所述的碱是碱金属醇盐或碱金属氢氧化物。
4.如上述第1项所定义的制备氟代醇的方法，其中所述的碱是选自由醇钠、氢氧化钠和氢氧化钾所组成的组中的至少一种。
5.如上述第1项所定义的制备氟代醇的方法，其中通过蒸馏所获得的通式(1)表示的氟代醇
     H(CFR1CF2)nCH2OH           (1)
(其中R1和n如前面所定义)具有不高于50ppm的蒸发残余物。
6.如上述第5项所定义的制备氟代醇的方法，其中通过蒸馏所获得的通式(1)表示的氟代醇
     H(CFR1CF2)nCH2OH           (1)
(其中R1和n如前面所定义)具有不高于25ppm的蒸发残余物。
7.如上述第5项所定义的制备氟代醇的方法，其中通过蒸馏所获得的通式(1)表示的氟代醇
     H(CFR1CF2)nCH2OH           (1)
(其中R1和n如前面所定义)具有不高于10ppm的蒸发残余物。
8.如上述第1项所定义的制备氟代醇的方法，其中的自由基源是选自由反应引发剂，紫外光和热能所组成的组中的至少一种。
9.如上述第8项所定义的制备氟代醇的方法，其中的自由基源为在反应温度下具有约10小时的半衰期的一种反应引发剂。
10.如上述第8项所定义的制备氟代醇的方法，其中的自由基源为一种过氧化物。
11.如上述第8项所定义的制备氟代醇的方法，其中的自由基源为二叔丁基过氧化物、碳酸叔丁基过氧异丙基酯或己酸叔丁基过氧-2-乙基酯。
12.如上述第1项所定义的制备氟代醇的方法，其中一种酸受体与自由基源一起使用。
13.一种由下列通式(1)表示的氟代醇，
      H(CFR1CF2)nCH2OH           (1)
(其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F)，该氟代醇具有不高于50ppm的蒸发残余物。
14.按照上述第13项的氟代醇，该氟代醇的蒸发残余物不高于25ppm。
15.按照上述第13项的氟代醇，该氟代醇的蒸发残余物不高于10ppm。
16.按照上述第13项的氟代醇，该氟代醇在甲醇中的吸收度(190-300nm)不高于0.2abs。
17.按照上述第13项的氟代醇，该氟代醇在甲醇中的吸收度(205nm)不高于0.1abs。
18.按照上述第17项的氟代醇，该氟代醇在甲醇中的吸收度(205nm)不高于-0.2abs。
19.上述第13项的氟代醇用于包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质的制造。
20.包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质，其中的记录层是使用上述第1项所定义的方法制备的下列式(1)的氟代醇
         H(CFR1CF2)nCH2OH             (1)
(其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F)或用上述第13项所定义的下列式(1)的氟代醇
         H(CFR1CF2)nCH2OH             (1)
(其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F)制成的。
在按照本发明的制备方法中，以过量于四氟乙烯或六氟丙烯的量使用甲醇。反应温度为大约40～140℃，反应时间为大约3～12小时，反应压力为大约0.2～1.2MPa。该反应可以在高压反应器如高压釜中进行。该反应***优选用氮气或氩气等惰性气体进行净化。
在反应完成后，可以将甲醇蒸出，并将残余物在碱存在下进一步蒸馏。此外，在反应混合物含有H(CF2CF2)nCH2OH(n≥3)或H(CF(CF3)CF2)nCH2OH(n≥2)杂质的情况下，优选的是将该杂质通过蒸馏预先除去。将含有式(1)的氟代醇
 H(CFR1CF2)nCH2OH           (1)
(其中R1和n如前面所定义)的反应混合物在一种碱存在下进行蒸馏或在该反应混合物与碱接触后进行蒸馏。
加入到上述反应混合物中或与上述混合物接触的碱优选的是具有不高于2的pKb值的碱，这些碱包括碱金属醇盐如甲醇钠、乙醇钠、丙醇钠、叔丁醇钾、乙醇锂等，碱金属氢氧化物如氢氧化钠、氢氧化钾、氢氧化锂等，氢氧化钙，氢氧化铝，氢氧化钡，氢氧化镁和碱石灰。碱的比例为相对于每千克已除去甲醇的反应混合物，碱量为约0.05～1.0摩尔，优选约0.1～0.5摩尔。
所述酸受体包括但不限于碱金属或碱土金属的碳酸盐和碳酸氢盐如碳酸钙、碳酸镁、碳酸钡、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾等，以及氧化钙，氢氧化钙和碱石灰。优选的酸受体是一种在反应过程中能够捕获所形成的酸，如HF，而不会增加反应体系的碱度的物质。
酸受体的使用量没有特别的限定，但基于每摩尔四氟乙烯或六氟丙烯，可以使用约0.001～0.1摩尔的酸受体。
作为自由基源或自由基发生体，可以使用选自由反应引发剂、紫外光和热能所组成的组中的至少一种。当自由基源为紫外光时，可以选择，例如，来自中压或高压汞灯的紫外光。当自由基源为热能时，可以选择，例如在250～300℃之间的温度。反应引发剂包括但不限于过氧化物，并且优选的是使用在反应温度下半衰期为大约10小时的反应引发剂。
优选的自由基源包括过丁基D(二叔丁基过氧化物)，过丁基O(己酸叔丁基过氧化-2-乙基酯)和过丁基I(碳酸叔丁基过氧化异丙基酯)。通常基于每摩尔四氟乙烯或六氟丙烯，可以使用约0.005～0.1摩尔的反应引发剂。
按照本发明而获得的氟代醇中的蒸发残余物的量为50ppm或更少，优选25ppm或更少，更优选10ppm或更少。
蒸发残余物的量可由下列方法测定。即将氟代醇在40℃，5mmHg的条件下蒸发并对残余物秤重，用基于氟代醇如HCF2CF2CH2OH的重量ppm表示。
按照本发明而获得的通式(1)的氟代醇在甲醇中的在205nm处的紫外吸收不高于0.1abs，优选-0.1abs或更低，更优选-0.2abs或更低。在甲醇中的紫外吸收可以使用1毫升通式(1)的氟代醇和3毫升甲醇的混合物作为样品并以甲醇作为参照物进行测量。
按照本发明的氟代醇“基本上”不含杂质是指(i)氟代醇蒸发的残余物的量不高于50ppm，优选不高于25ppm，更优选不高于10ppm和/或(ii)其在甲醇中的紫外吸收(205nm)不高于0.1abs，优选不高于-0.1abs，更优选不高于-0.2abs。
包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质可以通过将染料溶解在含有按照本发明的通式(1)的氟代醇的一种溶剂中，优选含有所说氟代醇的氟系溶剂中，接着进行一系列的常规操作，包括使用所得到的染料溶液涂敷基板并将该涂敷的基板干燥而获得一种包含有染料的记录层而进行制造。上述的染料包括花青染料、酞菁染料、吡喃噁染料、噻喃噁染料、鱼鲨烯噁(squarylium)染料、薁噁(azulenium)染料、靛酚染料、茚并苯胺(indoaniline)染料、三苯甲烷染料、醌染料、铵盐染料、二茚噁(diimmonium)染料和金属配合物染料。用于基板的原料包括塑料如聚碳酸酯、聚甲基丙烯酸甲酯，环氧树脂、无定形聚烯烃、聚酯和聚氯乙烯等，以及玻璃和陶瓷。为了改善表面的光滑度和粘合性或防止记录层脱落，可以在记录层和基板之间涂敷一层底漆或内涂层和/或可以在记录层上形成一层保护层。
按照本发明，可以容易地提供基本上不含杂质的，适用于包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质(光盘如CD-R，DVD-R等)或用于胶片的光敏材料的制造的HCF2CF2CH2OH，H(CF2CF2)2CH2OH和HCF(CF3)CF2CH2OH。
实施本发明的最佳方式
下面的实施例是对本发明的进一步的详细描述。
实施例1
将甲醇(2升)，二叔丁基过氧化物(45克)和碳酸钙(30克)加入到高压釜中。在用氮气将空气排出后，将四氟乙烯以600克/小时的起始速度引入该高压釜中。通过将温度和压力分别控制在125℃和0.8MPa，将反应进行6小时。
冷却后，将反应混合物蒸馏除去甲醇，然后蒸馏H(CF2CF2)nCH2OH(n为2或更高的整数)得到HCF2CF2CH2OH馏份(1.2升)。HCF2CF2CH2OH馏份的蒸馏残余物大约为600ppm并且其吸收(205nm)为2.0abs。毛细管气相色谱/质谱(GC/MS)分析显示含有各种醛类杂质如HCHO、HCF2CF2CHO、HCF2CHFCHO、HCF2CF2CF2CF2CHO、HCF2COOCH2CH＝CHCHO、HCF2CH2COOCH＝CHCHO、HCF2CF2CH(OH)OCH2CHO。
重复上述馏份的蒸馏步骤不会引起所说杂质的量，蒸馏残余物和吸收(205nm)的任何变化。
向所得到的HCF2CF2CH2OH馏份(1升)中加入28％的甲醇钠的甲醇溶液(30克)，并将该混合物在加热下蒸馏得到基本上不含杂质的HCF2CF2CH2OH。由此所获得的HCF2CF2CH2OH的蒸发残余物不高于10ppm，其吸收度(205nm)不高于-0.2abs。上述醛的量低于GC/MS的检出极限。
GC/MS的分析条件如下：
1)柱：液相DB-1301
薄膜厚度：1.00μm
柱尺寸：60m×0.247mm
2)分析条件
氦(He)载气：200kPa
空气：40kPa
H2：50kPa
温度：50℃保持5分钟，再以15℃/分钟的速度升温至220℃保持15分钟
注射室温度：200℃
实施例2
将H(CF2CF2)nCH2OH(n≥2)组分进行分馏以回收H(CF2CF2)2CH2OH组分。如实施例1的方法向该组分中加入甲醇钠，并将该混合物蒸馏得到蒸发残余物不高于25ppm的H(CF2CF2)2CH2OH。
实施例3
按照实施例1的相同的方法进行反应和蒸馏纯化，所不同的是用六氟丙烯代替四氟乙烯，结果得到具有蒸发残余物不高于25ppm和紫外(205nm)吸收不高于0.1abs的HCF(CF3)CF2CH2OH。
实施例4
将如实施例1中所获得的在碱存在下进行蒸馏之前的HCF2CF2CH2OH组分先经过一个碱石灰的柱子以除去HF。结果其气相色谱纯度为99.974％～99.5368％。
当将该低纯度的HCF2CF2CH2OH组分蒸馏时，得到具有蒸发残余物不高于50ppm和紫外(205nm)吸收不高于0.1abs的HCF2CF2CH2OH。

Claims (9)

1.一种由下列通式(1)表示的用于制备一种信息记录介质的具有不高于50ppm的蒸发残余物的氟代醇：
      H(CFR1CF2)nCH2OH             (1)
其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F。
2.按照权利要求1的氟代醇，该氟代醇的蒸发残余物不高于25ppm。
3.按照权利要求1的氟代醇，该氟代醇的蒸发残余物不高于10ppm。
4.按照权利要求1的氟代醇，该氟代醇在甲醇中的190-300nm吸收度不高于0.2abs。
5.按照权利要求1的氟代醇，该氟代醇在甲醇中的205nm吸收度不高于0.1abs。
6.按照权利要求5的氟代醇，该氟代醇在甲醇中的205nm吸收度不高于-0.2abs。
7.将权利要求1的氟代醇用于制造一种信息记录介质的方法，包含：
制备基板；和
建立在该基板上的适于激光写或读的记录层。
8.包含有基板和建立在该基板上的适于激光写和/或读的记录层的一种信息记录介质，其中的记录层是使用
用权利要求1所定义的下列式(1)的氟代醇
          H(CFR1CF2)nCH2OH              (1)
其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F制成的。
9.一种溶剂，其含有由下列通式(1)表示的用于制备一种信息记录介质的具有不高于50ppm的蒸发残余物的氟代醇：
         H(CFR1CF2)nCH2OH    (1)
其中当n＝1时，R1代表F或CF3；当n＝2时，R1代表F。
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