CN1922122A - 组合物、卤代组合物、化学生产和调聚反应方法 - Google Patents
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Abstract
本发明提供了组合物，其可包括：RF (RT) n Q、化学式I(I)、化学式II(II)，和/或RCl (RT) nH。RF基团可具有四个氟原子，RT基团可包括具有一个－CF3侧基的C－2基团，n可以最少是1，R1基团可包括一个碳原子，RCl基团可以是－CCI3，并且Q基团可包括一个或更多的元素周期表中的原子。本发明也提供了调聚反应的方法。
Description
要求优先权
本申请要求于2004年1月30日提出的、标题是“氟官能团、氟组合物、氟组合物的制造方法和材料处理方法”的美国临时专利申请序列号60/540,612的优先权，该美国临时专利申请作为参考结合于此。
技术领域
本公开内容涉及组合物(composition)、卤代组合物、化学生产和调聚反应方法。
背景技术
组合物如表面活性剂、聚合物和聚氨酯具有结合的卤化官能团。当组合物用作材料处理时和当组合物用于提高材料的性能时，这些官能团已被结合以影响组合物的性能。例如，结合卤化官能团的表面活性剂能够被单独用作灭火剂或用在如水成膜泡沫(AFFF)的制剂中。结合卤化官能团的聚合物和/或聚氨酯也已用于材料处理。为了制备这些组合物，能够合成卤化中间体组合物。
概要
本发明提供了组合物，其可包括RF(RT)nQ和/或
和
的一个或两个。这些组合物中，RF基团可具有至少四个氟原子，RT基团可包括至少一个C-2基团，其具有至少一个-CF3侧基，n可以至少是1，R1基团可包括至少一个碳原子，Q基团可包括一个或更多的元素周期表的原子。本发明提供了组合物，其也可包括RCl(RT)nH，RCl基团具有至少一个-CCl3基团。
本发明也提供了调聚反应方法，包括将至少一种含CF3主链物曝露于含氟调聚体以生产调聚物，含氟调聚体至少包括4个氟原子。
附图说明
该图是一个按照本发明例举方面的典型实施方案的系统的图表。
优选实施方案的详细描述
提交本发明公开内容是为了促进美国专利法的立法目的“推动科学和有用技术的进步”(第1条，第8款)。
根据附图，描述了组合物和制造组合物的方法。参看附图，系统10表示制备卤化组合物，包括试剂如主链物2、调聚体4和引发剂6，其被提供给反应器8以形成产品如调聚物9。在例举性实施方案中，系统10可执行调聚反应方法。依照一个实施方案，主链物2可曝露于调聚体4以形成调聚物9。按照另一个实施方案，主链物2可在引发剂6存在下曝露于调聚体4。反应器8也可安排在曝露过程中为试剂提供热量。
主链物2可包括至少一种含CF3化合物。含CF3化合物可具有一个C-2基团，该C-2基团具有至少一个-CF3侧基。在典型实施方案中，主链物2可包含一个链烯烃，例如3，3，3-三氟丙烯(TFP，trifluoropropene)。
调聚体4可包括卤素如氟和/或氯。调聚体4可包括至少四个氟原子并可表示为RFQ和/或RClQ。RF基团可包括至少四个氟原子，Q基团可包括一个或更多的元素周期表中的元素。例如，Q基团可以是H或I，RF基团是(CF3)2CF-和/或-C6F13。RCl基团可包括至少一个-CCl3基团。典型的调聚体可包括(CF3)2CFI、C6F13I、氯仿、HP(O)(OEt)2、BrCFClCF2Br、R-SH(R是一个含碳基团)，和/或MeOH。典型实施方案中，主链物2可包括三氟丙烯，调聚体4可包括(CF3)2CFI，主链物2对调聚体4的摩尔比从约1∶1到约1∶10，1∶4到约4∶1，和/或约2∶1到4∶1。
反应器8可以是任何实验室规模或工业规模的反应器，在特定实施方案中，反应器8可被配置以控制其中试剂的温度。依照典型实施方案，反应器8可用来在试剂曝露的过程中提供一个从约130℃到150℃的温度。
主链物2曝露于调聚体4而产生的调聚物9可包括RF(RT)nQ和/或RCl(RT)nH。RT基团可包括至少一个具有-CF3侧基的C-2基团，例如例如，典型产品包括
和/或
和
两者中的一个或两个，R1包括至少一个碳原子，如-CH2-。
典型实施方案中，n可至少是1，在其它实施方案中n可以是2，并且产品可包括
和/或
中的一种或更多种。
典型实施方案中，主链物三氟丙烯可曝露于调聚体(CF3)2CFI以形成调聚物
经由另一个例子，三氟丙烯可曝露于调聚体C6F13I以形成调聚物
根据另一个实施方案，主链物三氟丙烯也可曝露于调聚体CCl3Z(例如，Z＝H、Br，和/或Cl)以形成调聚物当利用与调聚体相比过量的主链物时，可以形成n至少是2的产品。例如，主链物对调聚体的摩尔比至少是2∶1，可以用来获得n至少是2的产品。例如并只通过实例，至少2摩尔的主链物三氟丙烯可曝露于至少1摩尔的调聚体(CF3)2CFI以形成
和
两者中的一种或两种。
在另外的实施方案中，引发剂6可在试剂曝露过程中提供给反应器8。引发剂6可包括热的、光化学的(UV)、自由基、和/或金属配合物，例如，包括过氧化物如二叔丁基过氧化物。引发剂6也可包括催化剂，例如Cu。例如，引发剂6和调聚体4可提供给反应器8，引发剂6对主链物2的摩尔比介于约0.001到约0.05之间，和/或介于约0.01到0.03之间。
根据典型实施方案，不同的引发剂6和主链物4可用于调聚主链物2，如下面的表1所提及。利用光化学的和/或金属配合物引发剂6的调聚反应可在分批条件下用卡里乌斯管式反应器8进行。利用热的和/或过氧化物引发剂6的调聚反应可在160和/或500cm3的哈斯特洛依合金反应器8中进行。调聚体4(纯的和/或过氧化物溶液)可在约60℃到180℃的温度下作为气体提供，调聚体4[T]0/主链物2[Tx]0的初始摩尔比R0可在0.25到1.5之间变化，反应时间从4到24小时，如下面表1所示。产品混合物可通过气相色谱进行分析，和/或产品可以蒸馏成不同馏分用1H和19F的NMR和/或13C的NMR分析。单基团加成物(n＝1)和双基团加成物(n＝2)产品可被确认，如表1所示。
| 表1三氟丙烯主链物的调聚反应 | |||||||||||
| 试验a | 引发剂d | R0 b | C0 b | T(℃) | tr(hrs) | P(bars)max min | ％主链物转化率 | 气相色谱测得的收率(％)c | |||
| 调聚物 | 单基团加成物(n＝1) | 双基团加成物(n＝2) | |||||||||
| 1 | 热 | 0.50 | - | 160 | 20 | 22 | 17 | 79.2 | 27.6 | 51.9 | 20.5 |
| 2 | 热 | 0.25 | - | 160 | 20 | 39 | 34 | 36.8 | 52.8 | 26.2 | 21 |
| 3 | 热 | 0.50 | - | 180 | 22 | 30 | 11 | 73.4 | 2.4 | 65.9 | 31.2 |
| 4 | Perk | 0.50 | 0.03 | 62 | 20 | 7 | 5 | 79.2 | 23.8 | 35.4 | 40.8 |
| 5 | AIBN | 0.50 | 0.03 | 82 | 18 | 10 | 7 | 79.2 | 17.4 | 38.8 | 42 |
| 6 | TRIG | 0.50 | 0.03 | 134 | 6 | 16 | 0.6 | 89.6 | 3.7 | 19 | 63.8 |
| 7 | DTBP | 050 | 0.03 | 140 | 6 | 17 | 0.2 | 97.9 | 3.7 | 19 | 63.8 |
| 8 | DTBP | 0.50 | 0.03 | 143 | 4 | 19 | 0.8 | 94.3 | 9.6 | 21 | 66.6 |
| 9 | DTBP | 1.4 | 0.03 | 150 | 4 | 13 | 1.1 | 95.2 | 22.5 | 54.4 | 15.7 |
| 10 | DTBP | 0.75 | 0.03 | 145 | 4 | 20 | 3.0 | 93.8 | 6.8 | 34.1 | 49.0 |
| 11 | DTBP | 1.2 | 0.03 | 150 | 4 | 20 | 5.0 | 90.0 | 14.9 | 46.3 | 33.4 |
| 12 | DTBP | 1.4 | 0.03 | 150 | 4 | 21 | 3.5 | 95.0 | 12.6 | 54.1 | 28.6 |
| 13 | DTBP | 1.5 | 0.03 | 150 | 4 | 19 | 5.0 | 95.0 | 24.6 | 43.9 | 28.3 |
a)调聚体在试验Nos 1-9中可以是C6F13I，在试验No 10-13中可以是(CF3)2CFI
b)R0＝[T]0/[Tx]0；C0＝[In]0/[Tx]
c)重TFP调聚物(n＞2)可构成产品其余部分
d)引发剂可以是Perk.16s(t-丁基环己基二碳酸酯)；AIBN；Trig.101(2，5-二(叔丁基过氧)-2，5-二甲基己烷)；和DTBP。
Claims (28)
1.一种组合物，其包含RF(RT)nQ，其中：
RF基团包含至少四个氟原子；
RT基团包含至少一个C-2基团，该C-2基团具有至少一个-CF3侧基；
n至少是1；和
Q基团包含一个或更多的元素周期表中的原子。
2.权利要求1的组合物，其中RF基团包含至少一个-CF3基团。
3.权利要求1的组合物，其中RF基团包含至少两个-CF3基团。
4.权利要求3的组合物，其中RF基团包含-CF(CF3)2。
5.权利要求1的组合物，其中RF基团包含-C6F13。
6.权利要求1的组合物，其中RT基团包含
7.权利要求1的组合物，其中n至少是2并且所述组合物包含
8.权利要求1的组合物，其中n至少是2并且所述组合物包含
9.权利要求1的组合物，其中Q基团包含一种卤素。
10.一种组合物，其包含
和
中的一种或两种，
其中：
RF基团含有至少四个氟原子；
R1基团含有至少一个碳原子；
n至少是1；和
Q基团含有一个或更多的元素周期表中的原子。
11.权利要求10的组合物，其中RF基团包含至少两个-CF3基团。
12.权利要求10的组合物，其中R1基团由-CH2-组成。
13.权利要求10的组合物，其中n等于1并且所述组合物包含
14.权利要求10的组合物，其中Q基团包含至少一种卤素。
15.一种组合物，其包含：
RCl(RT)nH，其中：
RCl基团至少包含-CCl3；
RT基团包含至少一个C-2基团，所述C-2基团具有至少一个-CF3侧基；和
n至少是1。
16.权利要求15的组合物，其中n至少是2并且所述组合物包含
17.权利要求15的组合物，其中n至少是2并且所述组合物包含
18.一种调聚反应方法，该方法包含将至少一种含CF3的主链物曝露于含氟调聚体以生产调聚物，其中含氟调聚体含有至少四个氟原子。
19.权利要求18的方法，其中含CF3的主链物是三氟丙烯。
20.权利要求18的方法，其中含氟调聚体是(CF3)2CFI。
21.权利要求18的方法，其中在引发剂存在的情况下将含CF3的主链物曝露于含氟调聚体。
22.权利要求21的方法，其中引发剂包含一种过氧化物。
23.权利要求22的方法，其中过氧化物包含二叔丁基过氧化物。
24.权利要求22的方法，其中曝露发生在反应器中，并且将引发剂和调聚体提供给反应器，引发剂和调聚体的摩尔比介于约0.001到约0.05之间。
25.权利要求24的方法，其中引发剂和调聚体的摩尔比介于约0.01到约0.03之间。
26.权利要求19的方法，其中曝露发生在反应器中，曝露过程中反应器内的温度为约130℃到约150℃。
27.权利要求18的方法，其中：
含CF3的主链物是三氟丙烯；和
调聚物包含
其中：
RF基团包含至少四个氟原子；
n至少是1；和
Q基团包含一个或更多的元素周期表中的原子。
28.权利要求18的方法，其中：
含CF3的主链物是三氟丙烯；
含氟调聚体是(CF3)2CFI；和
主链物与调聚体的摩尔比是从约2∶1到约4∶1。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54061204P | 2004-01-30 | 2004-01-30 | |
| US60/540,612 | 2004-01-30 | ||
| PCT/US2005/003137 WO2005074593A2 (en) | 2004-01-30 | 2005-01-28 | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1922122A true CN1922122A (zh) | 2007-02-28 |
Family
ID=39099662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA200580003525XA Pending CN1922122A (zh) | 2004-01-30 | 2005-01-28 | 组合物、卤代组合物、化学生产和调聚反应方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20070161537A1 (zh) |
| EP (1) | EP1718721A4 (zh) |
| JP (1) | JP2007526360A (zh) |
| KR (2) | KR20070094981A (zh) |
| CN (1) | CN1922122A (zh) |
| CA (1) | CA2554292A1 (zh) |
| MX (1) | MXPA06008620A (zh) |
| WO (1) | WO2005074593A2 (zh) |
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| KR20080009760A (ko) * | 2004-01-30 | 2008-01-29 | 그레이트 레이크스 케미칼 코퍼레이션 | 조성물 및 할로겐화 조성물 |
| US20070027349A1 (en) * | 2005-07-28 | 2007-02-01 | Stephan Brandstadter | Halogenated Compositions |
| US9168408B2 (en) * | 2010-03-25 | 2015-10-27 | The Chemours Company Fc, Llc | Surfactant composition from polyfluoroalkylsulfonamido alkyl amines |
| EP3638643B1 (en) | 2017-06-12 | 2023-01-18 | Novaliq GmbH | Process for the preparation of semifluorinated alkanes using grignard reagents |
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-
2005
- 2005-01-28 KR KR1020077019246A patent/KR20070094981A/ko not_active Application Discontinuation
- 2005-01-28 MX MXPA06008620A patent/MXPA06008620A/es unknown
- 2005-01-28 CN CNA200580003525XA patent/CN1922122A/zh active Pending
- 2005-01-28 JP JP2006551578A patent/JP2007526360A/ja active Pending
- 2005-01-28 CA CA002554292A patent/CA2554292A1/en not_active Abandoned
- 2005-01-28 EP EP05712545A patent/EP1718721A4/en not_active Withdrawn
- 2005-01-28 US US10/587,323 patent/US20070161537A1/en not_active Abandoned
- 2005-01-28 KR KR1020067015479A patent/KR20060132888A/ko not_active Application Discontinuation
- 2005-01-28 WO PCT/US2005/003137 patent/WO2005074593A2/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| US20070161537A1 (en) | 2007-07-12 |
| WO2005074593A2 (en) | 2005-08-18 |
| EP1718721A2 (en) | 2006-11-08 |
| KR20060132888A (ko) | 2006-12-22 |
| JP2007526360A (ja) | 2007-09-13 |
| CA2554292A1 (en) | 2005-08-18 |
| MXPA06008620A (es) | 2007-03-21 |
| KR20070000463A (ko) | 2007-01-02 |
| KR20070094981A (ko) | 2007-09-27 |
| WO2005074593A3 (en) | 2006-03-16 |
| EP1718721A4 (en) | 2012-08-08 |
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