CN1659175A - 单酰基和二酰基氧化膦的多聚体形式 - Google Patents
单酰基和二酰基氧化膦的多聚体形式 Download PDFInfo
- Publication number
- CN1659175A CN1659175A CN038134772A CN03813477A CN1659175A CN 1659175 A CN1659175 A CN 1659175A CN 038134772 A CN038134772 A CN 038134772A CN 03813477 A CN03813477 A CN 03813477A CN 1659175 A CN1659175 A CN 1659175A
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- Prior art keywords
- general formula
- compound
- phosphine
- acid
- dimer
- Prior art date
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- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 32
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000000539 dimer Substances 0.000 claims abstract description 19
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 54
- -1 MAPO compound Chemical class 0.000 claims description 48
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 18
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- 235000019253 formic acid Nutrition 0.000 claims description 16
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
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Abstract
本发明涉及通式I的BAPO化合物的二聚体和多聚体形式和通式II的MAPO化合物的二聚体和多聚体形式,其中R1、R2、和R3相互独立地是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;Q是2-3价或4价的亚芳基;n是1-4,m是0-2,n+m是2、3或4,条件是R1和R3相互不同。本发明还涉及制备通式I的BAPO化合物的二聚体或多聚体形式和通式II的MAPO化合物的二聚体或多聚体形式的方法,特征在于(n+m)当量的二金属化的膦R1P(M) 2与一当量的二或多甲酸卤化物反应形成通式III的中间体,该中间体III然后再与(n+m)当量的另外的甲酸卤化物(R2-CO-Hal)反应或与卤化物R3-Hal反应。反应产物然后氧化形成通式I或II的氧化膦。
Description
本发明涉及单酰基氧化膦(MAPO)、二酰基氧化膦(BAPO)的新的二聚体和多聚体形式,涉及二酰基氧化膦(BAPO)的新环状形式,涉及它们的制备方法以及在该方法中所获得的作为中间体的新酰基膦化合物。
在欧洲专利公开EP-A 0601413中已经描述了以下通式的单酰基氧化膦二聚体的制备。
该方法特征在于,芳烃-二酰基氯与例如烷氧基-二苯基-膦反应。由于烷氧基-二苯基-膦反应物,所获得的化合物是单酰基氧化膦的对称二聚体形式,即残基R5=R6。关于不对称形式,残基R5或R6中的一个必须是烷氧基。
美国专利公开2001/0031898描述了二酰基氧化膦的单体形式的制备
通过酰卤Ar-CO-X与二金属化的膦RP(M)2反应,随后所获得的产物与一种酰卤反应。BAPO化合物的二聚体形式被美国专利公开2001/0031898中所述化合物的一般定义所包括,但是,它们在该专利公开中没有真正和明确地公开,也没有举例说明其制备。
仍然需要发现制备BAPO和MAPO化合物的二聚体和多聚体的对称和不对称形式以及BAPO化合物环状形式的方法,在MAPO化合物的情况下,依靠所述方法应该具有宽的在磷原子上选择取代基的范围。
一方面,本发明涉及通式I的BAPO化合物的二聚体和多聚体形式
其中
R1是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;
R2是未取代的或取代的C3-C6环烷基或C5-C14芳基;
Q是2-3价或4价的亚芳基;
n是1-4,m是0-2,n+m是2、3或4。
本发明还涉及通式II的MAPO化合物的二聚体和多聚体形式
其中
R1和R3相互独立地是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;
Q是2-3价或4价的亚芳基;
n是1-4,m是0-2,n+m是2、3或4;
条件是R1和R3相互不同。
本发明还涉及制备通式I的BAPO化合物的二聚体或多聚体形式和通式II的MAPO化合物的二聚体或多聚体形式的方法,特征在于(n+m)当量的二金属化的膦R1P(M)2与一当量的二或多甲酸卤化物
反应形成通式III的中间体
该中间体然后再与(n+m)当量的甲酸卤化物(R2-CO-Hal)反应形成通式IV二酰基膦中间体的二聚体或多聚体形式
或与卤化物R3-Hal反应形成通式V单酰基膦中间体的二聚体或多聚体形式
所述的膦IV或V然后被氧化形成通式I或II的氧化膦,其中M是Li、Na或K,和R1、R2和R3;Q、n和m如上文所定义。
通式III的中间体化合物是新的,也是本发明的一部分。因此,本发明还涉及上文所定义的通式III化合物。通式III化合物通过31P-.NMR谱学鉴定,于室温惰性气体下在溶液中稳定存在若干周。
本发明还涉及通式VI和VII的BAPO化合物的环状形式
其中
R1是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;
U是2价的亚芳基,U′是4价的亚芳基。
本发明还涉及制备通式VI的BAPO化合物环状形式的方法,特征在于一当量的二金属化的膦R1P(M)2与一当量的二甲酸卤化物
反应形成通式III’的中间体
该中间体环化,然后氧化形成通式VI的氧化膦,其中R1、M和U如上文所定义。
本发明还涉及制备通式VII的BAPO化合物环状形式的方法,特征在于二当量的二金属化的膦R1P(M)2与一当量的四甲酸卤化物
反应形成通式III”的中间体
该中间体环化,然后氧化形成通式VII的氧化膦,其中R1、M和U’如上文所定义。
优选使用通式I或II的化合物,其中n是1和m是1。
定义
C1-C12烷基是直链的或支链的,例如是C1-C12烷基、C1-C8烷基、C1-C6烷基或C1-C4烷基。实例是甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、庚基、2,4,4-三甲基戊基、2-乙基己基、辛基、壬基、癸基、十一烷基、十二烷基。烷基可被O、S或N(C1-C12烷基)间隔一次或多次。如果所述基团被两个或多个O、S或N(C1-C12烷基)间隔,那么在每种情况下O原子、S原子或N(C1-C12烷基)基团相互之间被至少一个亚甲基分隔。因此O原子、S原子或N(C1-C12烷基)基团不是直接连续的。例如产生的结构单元如-CH2-O-CH3、-CH2CH2-O-CH2CH3、-[CH2CH2O]z-CH3,其中z=1-9、-(CH2CH2O)7CH2CH3、-CH2-CH(CH3)-O-CH2-CH2CH3、-CH2-CH(CH3)-O-CH2-CH3、-CH2SCH3或-CH2-N(CH3)2。
烷基可被C1-C12烷基、C1-C12烷氧基、-S-C1-C12烷基、苯基、苯氧基、-COOC1-C12烷基、-COO-C5-C14芳基或CN单取代或多取代。
此处使用的术语“C1-C12烷氧基”指O-C1-C12烷基,其中烷基如上文所定义。
C3-C6环烷基的实例是环丙基、环丁基、环戊基、环己基。C3-C6环烷基可被C1-C12烷基、C1-C12烷氧基、-S-C1-C12烷基、苯基、苯氧基、-COOC1-C12烷基、-COO-C5-C14芳基或CN取代。实例是2,4,6-三甲基环己基、2,6-二甲基环己基和2,6-二甲氧基环己基。
C5-C14芳基是苯基、萘基、联苯基、蒽基等。
芳基可被卤素、苯基、C1-C12烷基和/或C1-C12烷氧基、-S-C1-C12烷基、CF3、Cl、-N(C1-C12烷基)2或-N(被O中断的C1-C12烷基)2单取代或多取代。
实例是:
Q是由以下的二或多甲酸卤化物,优选氯化物衍生的2-3或4价亚芳基。
通式A的化合物
其中
R是C1-C12烷基、C1-C12烷氧基、C1-C12烷硫基、C5-C14芳基、O-C5-C14芳基、卤素、NH(C1-C12烷基)、N(C1-C12烷基)2、C(O)O(C1-C12烷基)、CO-NH(C1-C12烷基)、CO-N(C1-C12烷基)2或CF3。
可商购的通式A化合物是:
邻苯二甲酸及其衍生物,例如四氟或四氯邻苯二甲酸、3-氟邻苯二甲酸、4-(三氟甲基)邻苯二甲酸、4-氯或4,5-二氯邻苯二甲酸、4-甲基邻苯二甲酸;
苯连三酸、偏苯三酸和1,2,4,5-苯四酸;
间苯二酸及其衍生物,例如四氟间苯二酸、4-溴间苯二酸、4-羟基或5-羟基间苯二酸、5-氨基间苯二酸;
1,3,5-苯三酸、5-甲基-1,3-苯二甲酸;
对苯二酸及其衍生物,例如四氟或四氯对苯二酸、2-溴对苯二酸、2-氨基对苯二酸、2,5-二甲基对苯二酸、2,5-二氯或2,5-二溴对苯二酸。
通式B的化合物
其中R如通式A所定义。
可商购的通式B化合物是1,4,5,8-萘四甲酸或1,4,5,8-萘四甲酸水合物。
通式C化合物
其中R如通式A所定义。
可商购的通式C化合物是2,3-萘二甲酸或1,4-萘二甲酸。
通式D化合物
其中R如通式A所定义,X是键、-O-、-S-、亚甲基、-CH(CH3)-、-C(CH3)2-、-C(CF3)2-、-C(O)-、-S(O)-或-S(O)2-。
可商购的通式D化合物是3,3’,4,4’-二苯甲酮四甲酸、2,3,2’-联苯基三甲酸或4,4’(六氟异亚丙基)邻苯二甲酸。
通式E的化合物
其中R如通式A所定义,Y是H2、O、S或CH2。
可商购的是9-芴酮-2,7-二甲酸
通式F或G的化合物
其中R和Y如上文所定义,W是O、S、CH2或N(C1-C12烷基)。
可商购的是2,7-二叔丁基-9,9-二甲基-4,5-呫吨二甲酸。
通式H、I、J、K、L、M、N或O的化合物
其中
k是1-3,
R如上文所定义,
R’是氢、苯基、C1-C12烷基或C3-C6环烷基,
A选自C5-C14亚芳基、C3-C6环亚烷基或二环亚烷基、直链或支链的任选地被不连续的-O-或-S-原子,或被选自-CO-、-COO-、-OCO-、-O-COO-、亚苯基、C5-C14亚芳基、C3-C6环亚烷基、-CH=CH-、二环亚烷基、亚联苯基、-Si(CH3)2-、-Si(CH3)2-O-Si(CH3)2-或-CF2-中断一次或多次的C2-C24亚烷基。
基团A可被C1-C12烷基、C1-C12烷氧基、-S-C1-C12烷基、苯基、苯氧基、-O-COC1-C12烷基、-O-COC5-C14芳基、-COOC1-C12烷基、-COO-C5-C14芳基、CN、CF3、F或Cl取代。
关于通式VI的BAPO化合物的环状形式
U是由以下的二甲酸卤化物,优选氯化物,U1-U4产生的二价亚芳基
其中R和X如上文所定义。
关于通式VII的BAPO化合物的环状形式
U’是由以下的四甲酸卤化物,优选氯化物,U5和U6衍生的四价亚芳基,
该方法的起始化合物:
金属化的膦R1P(M)2的制备可通过例如适合的卤化磷R1P(Hal)2(其制备是已知的,例如由W.Davies公开在J.Chem.Soc.(1935),462和J.Chem.Soc.(1944),276中)与相应的碱金属反应来进行。适合的金属(M)是锂、钠或钾。锂是优选的。也可使用上述金属的混合物。4-8摩尔当量的碱金属是优选使用的。该反应优选在溶剂中进行。特别地,关于溶剂,可使用在大气压下和室温为液体的醚。实例是二甲醚、乙醚、甲丙醚、1,2-二甲氧基乙烷、双(2-甲氧基乙基)醚、二噁烷或四氢呋喃。优选使用四氢呋喃。反应温度优选为-60℃至+120℃。
制备金属化膦的另一可行的方法是,例如,适合的膦R1P(H)2与相应的碱金属氢化物或烷基锂化合物在排除空气的惰性溶剂中在例如-80℃至+120℃反应。有利地,使用2-4摩尔当量的碱金属氢化物或烷基锂化合物。适合的溶剂是例如上文所述的醚,或惰性溶剂,例如烷烃、环烷烃,或芳族溶剂如甲苯、二甲苯、均三甲基苯。
适合的芳基膦可通过相应的芳基二氯膦[Ar-P-Cl2]、芳基膦酸酯[Ar-P-O(OR’)2]和芳基亚膦酸酯[Ar-P(OR’)2]利用LiAlH4;SiHCl3;Ph2SiH2(Ph=苯基);a)LiH,b)H2O;a)Li/四氢呋喃,b)H2O或a)Na/甲苯,b)H2O还原来制备。上述方法描述在例如US6020528(5-6栏)中。使用LiAlH4的氢化在例如Helv.Chim.Acta 1966,No.96,842中给出。
用作原料的二或多甲酸卤化物是已知的物质,其中一些是可得的。实例如上文所列举。
不能商购的甲酸氯化物可由相应的甲酸起始利用已知的反应来制备。相应的甲酸可根据如下的方法进行制备。
化合物H:通过酸酐与二、三或四官能团醇反应。
适合的酸酐是,例如,邻苯二甲酸酐、苯连三酸酐、偏苯三酸酐、四氟邻苯二甲酸酐或4,5-二氯邻苯二甲酸酐。
化合物J:通过羟基甲酸与二、三或四官能团酯的酯交换反应。
适合的羟基甲酸是,例如,4-羟基邻苯二甲酸、5-羟基间苯二酸、3-羟基或4-羟基苯甲酸或水杨酸。
化合物K:通过氨基甲酸与二、三或四官能团的酰基氯反应
适合的氨基甲酸是,例如,3-氨基或4-氨基邻苯二甲酸、5-氨基间苯二酸、2-氨基对苯二酸、邻氨基苯甲酸、3-氨基或4-氨基苯甲酸。
化合物L、M或N:通过卤素取代的甲酸与二、三或四官能团的醇、胺或硫醇反应
X=O、S、NR’
适合的卤素取代的甲酸是,例如,3-氟或4-氯邻苯二甲酸、2-氟间苯二酸、2-氟或4-氟苯甲酸或4-氯苯甲酸。
化合物O:通过羟基甲酸与二、三或四官能团的氯甲酸酯反应。
适合的羟基甲酸是,例如,4-羟基邻苯二甲酸、5-羟基间苯二酸、3-羟基或4-羟基苯甲酸、水杨酸。
BAPO化合物的环状形式可由以下通式U1的二甲酸氯化物:邻苯二甲酸、四氟邻苯二甲酸、4,5-二氯邻苯二甲酸、4-羟基、3-氟或4-氯邻苯二甲酸;通式U2的2,2-氧基二苯甲酸或联苯甲酸;通式U3的萘-1,8-二甲酸;通式U4的2,3-萘二甲酸起始来制备;或者由以下的四甲酸起始制备:3,3’,4,4’-二苯甲酮四甲酸或4,4’-(六氟异亚丙基)二邻苯二甲酸。
发明方法
该方法通过甲酸卤化物与金属化的膦优选在惰性溶剂如THF、二噁烷或乙醚中在-20至80℃反应来开始。
制备BAPO或MAPO化合物二聚体或多聚体形式的方法的重要特征,包括控制金属化膦与二或多甲酸氯化物的摩尔比。每当量的酰基氯使用约1当量的金属化膦是理想的。为了维持过量的膦,优选甲酸氯化物滴入膦中。每当量的酰基氯使用约0.5当量的金属化膦得到环状二酰基氧化膦。
二或多甲酸氯化物与金属化的膦反应得到通式III结构的中间体。
为了制备MAPO化合物,该中间体用烷基或芳基卤化物处理得到P-烷基化的膦。烷基化试剂缓慢地加入。该反应优选在与得到中间体的第一反应步骤相同的溶剂中和相同的温度进行。
为了制备BAPO化合物,该中间体用另一甲酸卤化物处理得到P-酰基化的膦。酰基化试剂缓慢地加入。该反应优选在与得到中间体的第一反应步骤相同的溶剂中和相同的温度进行。
膦的氧化利用本领域常用的氧化剂来进行。适合的氧化剂是,例如,过氧化氢、空气或纯氧气。
应用
通式I和II的MAPO和BAPO化合物以及通式VI或VII的环状BAPO化合物可被用作烯键式不饱和化合物或包含上述化合物的混合物进行光聚合的光敏引发剂。该应用也可结合其它的光敏引发剂和/或其它的添加剂来进行。
因此,本发明还涉及一种光聚合组合物,包括
(a)至少一种烯键式不饱和的光聚合化合物,和
(b)作为光敏引发剂的至少一种如上文所定义的通式I、II、VI或VII的化合物。
不饱和化合物可含有一个或多个烯双键。它们可以是低分子量的(单体的)和较高分子量的(低聚体的)。含有双键的单体的实例是烷基或羟基烷基丙烯酸酯或甲基丙烯酸酯,例如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、2-乙基己基丙烯酸酯或2-羟基乙基丙烯酸酯、丙烯酸异冰片酯、甲基丙烯酸甲酯或甲基丙烯酸乙酯。也可以是硅或氟改性的树脂,例如硅丙烯酸酯。另外的实例是丙烯腈、丙烯酰胺、甲基丙烯酰胺、N-取代的(甲基)丙烯酰胺、乙烯基酯如乙酸乙烯酯、乙烯基醚如异丁基乙烯醚、苯乙烯、烷基和卤代苯乙烯、N-乙烯基吡咯烷酮、氯乙烯或亚乙烯基二氯。
含有两个或多个双键的单体的实例是二丙烯酸乙二醇酯、二丙烯酸丙二醇酯、二丙烯酸新戊二醇酯、二丙烯酸己二醇酯、或双酚A二丙烯酸酯、4,4’-双(2-丙烯酰氧基乙氧基)联苯基丙烷、三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯或四丙烯酸酯、丙烯酸乙烯酯、二乙烯基苯、琥珀酸二乙烯酯、邻苯二甲酸二烯丙酯、磷酸三烯丙酯、异氰脲酸三烯丙酯或三(2-丙烯酰乙基)异氰脲酸。
较高分子量(低聚的)聚合不饱和化合物的实例是丙烯酸化的环氧树脂、聚氨基甲酸酯、被丙烯酸化或含有乙烯醚或环氧基的聚醚和聚酯。不饱和低聚体另外的实例是大多由马来酸、邻苯二甲酸和一种或多种二醇制备的并具有约500-3000分子量的不饱和聚酯树脂。另外,也可使用乙烯醚单体和低聚体,和含有聚酯、聚氨基甲酸酯、聚醚、聚乙烯醚和环氧主链的马来酸酯封端的低聚体。特别地,如WO90/01512所述的含有乙烯醚基的低聚体和聚合物的组合是非常适合的。但是,乙烯醚和马来酸官能团化的单体的共聚物也是适合的。上述不饱和低聚体可被称作预聚物。
特别适合的化合物的实例是烯键式不饱和羧酸和多元醇或聚环氧化物的酯,和在主链或支链基团中含有烯键式不饱和基团的聚合物,例如不饱和聚酯、聚酰胺和聚氨基甲酸酯及其共聚物,聚酯树脂,聚丁二烯和丁二烯共聚物,聚异戊二烯和异戊二烯共聚物,在支链中含有(甲基)丙烯酸基团的聚合物和共聚物,以及上述一种或多种聚合物的混合物。
不饱和羧酸的实例是丙烯酸、甲基丙烯酸、巴豆酸、衣康酸、肉桂酸、不饱和脂肪酸如亚麻酸或油酸。优选丙烯酸和甲基丙烯酸。
适合的多元醇是芳族多元醇,特别是脂肪族多元醇和环状脂肪族多元醇。芳族多元醇的实例是氢醌、4,4’-二羟基联苯、2,2-二(4-羟基苯基)丙烷,还有线型酚醛清漆和可熔酚醛树脂。聚环氧化物的实例是基于所述多元醇,特别是芳族多元醇和表氯醇的那些聚环氧化物。另外,在聚合物链或侧基中含有羟基的聚合物和共聚物,例如聚乙烯醇及其共聚物或羟基烷基聚甲基丙烯酸酯或其共聚物也适于用作多元醇。另外适合的多元醇是含有羟基末端的酯类低聚物。
脂族多元醇和环状脂族多元醇的实例是含有,优选2-12个碳原子的亚烷基二醇,例如乙二醇、1,2-或1,3-丙二醇、1,2-、1,3-或1,4-丁二醇、戊二醇、己二醇、辛二醇、十二烷二醇、二甘醇、三甘醇、优选200-1500分子量的聚乙二醇、1,3-环戊二醇、1,2-、1,3-或1,4-环己二醇、1,4-二羟基甲基环己烷、甘油、三(β-羟基乙基)胺、三羟甲基乙烷、三羟甲基丙烷、季戊四醇、二季戊四醇和山梨醇。
多元醇可利用一种或不同的不饱和羧酸部分地或完全地酯化,其中部分酯中的自由羟基可被改性,例如用其它的羧酸醚化或酯化。
酯的实例是:
三羟甲基丙烷三丙烯酸酯、三羟甲基乙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、三羟甲基乙烷三甲基丙烯酸酯、丁二醇二甲基丙烯酸酯、三甘醇二甲基丙烯酸酯、四甘醇二丙烯酸酯、季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇二丙烯酸酯、二季戊四醇三丙烯酸酯、二季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇六丙烯酸酯、三季戊四醇八丙烯酸酯、季戊四醇二甲基丙烯酸酯、季戊四醇三甲基丙烯酸酯、二季戊四醇二甲基丙烯酸酯、二季戊四醇四甲基丙烯酸酯、三季戊四醇八甲基丙烯酸酯、季戊四醇二衣康酸酯、二季戊四醇三衣康酸酯、二季戊四醇五衣康酸酯、三季戊四醇六衣康酸酯、乙二醇二丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、1,4-丁二醇二衣康酸酯、山梨醇三丙烯酸酯、山梨醇四丙烯酸酯、季戊四醇改性的三丙烯酸酯、山梨醇四甲基丙烯酸酯、山梨醇五丙烯酸酯、山梨醇六丙烯酸酯、酯低聚物丙烯酸酯和甲基丙烯酸酯、甘油二丙烯酸酯和三丙烯酸酯、1,4-环己烷二丙烯酸酯、分子量为200-1500的聚乙二醇的二丙烯酸酯和二甲基丙烯酸酯、或它们的混合物。
也适合作为组分(a)的是优选含有2-6,特别是2-4个氨基的芳族聚胺、环状脂族聚胺和脂族聚胺的相同或不同的不饱和羧酸的酰胺。上述聚胺的实例是乙二胺、1,2-或1,3-丙二胺、1,2-、1,3-或1,4-丁二胺、1,5-戊二胺、1,6-己二胺、辛二胺、十二烷二胺、1,4-二氨基环己烷、异佛尔酮二胺、苯二胺、联苯二胺、二-β-氨基乙醚、二亚乙基三胺、三亚乙基四胺、二(β-氨基乙氧基)乙烷或二(β-氨基丙氧基)乙烷。另外适合的聚胺是支链上存在或不存在另外氨基的聚合物和共聚物以及含有氨基端基的酰胺低聚物。上述不饱和酰胺的实例是:亚甲基二丙烯酰胺、1,6-亚己基二丙烯酰胺、二亚乙基三胺三甲基丙烯酰胺、二(甲基丙烯酰胺丙氧基)乙烷、β-甲基丙烯酰胺乙基甲基丙烯酸酯、N[(β-羟基乙氧基)乙基]丙烯酰胺。
适合的不饱和聚酯和聚酰胺由例如马来酸和二醇或二胺衍生而来。马来酸可用其它的二羧酸代替。它们可与烯键式不饱和共聚单体如苯乙烯一起使用。聚酯和聚酰胺也可由二羧酸和烯键式不饱和二醇或二胺,特别是由较长链的含有例如6-20个碳原子的化合物衍生而来。聚氨基甲酸酯的实例是由饱和或不饱和的二异氰酸酯和不饱和或饱和的二醇构成。
聚丁二烯和聚异戊二烯及其共聚物是已知的。适合的共聚单体是,例如,烯烃,如乙烯、丙烯、丁烯、己烯、(甲基)丙烯酸酯、丙烯腈、苯乙烯或氯乙烯。在支链中含有(甲基)丙烯酸酯基团的聚合物同样是已知的。它们可以是,例如,基于线型酚醛清漆的环氧树脂与(甲基)丙烯酸的反应产物,乙烯醇的均聚物或共聚物或其用(甲基)丙烯酸酯化的羟基烷基衍生物,或用羟基烷基(甲基)丙烯酸酯酯化的(甲基)丙烯酸酯的均聚物和共聚物。
光聚合的化合物可单独使用或以任一需要的混合物的形式使用。优选使用多元醇(甲基)丙烯酸酯的混合物。
也可向本发明组合物中加入粘合剂;如果光聚合化合物是液体或粘性物质这样做是特别有利的。粘合剂的量基于总固体量可以是,例如5-95%重量,优选10-90%重量,特别优选40-90%重量。因此,粘合剂应根据应用领域和所需要的特性,如在水或有机溶剂体系中的扩展的可能性,对基质的粘性以及对氧的敏感性进行选择。
适合的粘合剂的实例列在美国专利公开2001/0031898中,其公开内容包括在本申请中作为参考。
除了光敏引发剂,光聚合混合物还可含有多种添加剂,如热抑制剂、增加储藏稳定性的化合物、防日光老化剂如列在美国专利公开2001/0031898中的以下的防日光老化剂:2-(2’-羟基苯基)苯并三唑、2-羟基苯甲酮、未取代或取代的苯甲酸的酯、丙烯酸酯、位阻胺、草酰胺、2-(2-羟基苯基)-1,3,5-三嗪、亚磷酸酯和亚膦酸酯。
光聚合混合物还可含有光敏剂,如列在美国专利公开2001/0031898中的以下的光敏剂:
三羟乙基胺、N-甲基二羟乙基胺、对二甲基氨基苯甲酸乙酯或米蚩酮、苯甲酮、噻吨酮,还特别是异丙基噻吨酮、蒽醌和3-酰基香豆素衍生物、三联苯、二苯乙烯甲酮、和3-(芳酰基亚甲基)噻唑啉、樟脑醌、而且还有四溴荧光素、若丹明和四碘荧光素染料。根据预定的用途,另外常用的添加剂是荧光增白剂、填料、颜料,包括白色和彩色颜料、染料、抗净电剂、润湿剂或均化剂。
根据目前的应用领域和该领域所需的特性来选择添加剂。上述的添加剂在本领域是常用的,因此以在本领域常用的量使用。可用的添加剂的具体实例在美国专利公开2001/0031898中给出。
在某些情况下,使用本发明两种或多种光敏引发剂的混合物是有利的。当然,也可以使用与已知光敏引发剂的混合物。
光聚合组合物基于组合物优选含有0.05-20%重量,如0.05-15%重量,优选0.1-5%重量的光敏引发剂。如果使用光敏引发剂的混合物,所述光敏引发剂的量是基于所有加入的光敏引发剂的量。
光聚合组合物可用于多种用途,例如用作印刷油墨,如丝网印刷油墨、橡皮凸版印刷油墨或胶版印刷油墨,用作清漆涂层,用作颜色涂层,用作白色涂层,例如用于木材或金属的,用作粉末涂料,用作油漆,尤其是纸、水、金属或塑料用的,用作日光固化的涂料,用于标记建筑和道路、用于照相还原方法、用于全息记录材料、用于图象记录方法或用于制备利用有机溶剂或含水碱介质显影的印刷板、用于丝网印刷面罩的制备,用作牙齿充填材料,用作粘合剂,用作压敏粘合剂,用作层压树脂,用作光致抗蚀剂,例如抗电性、抗腐蚀性和耐久性,液体并干燥的薄膜二者,用作光结构电介体,和用作电路的焊接阻挡面罩,用作保护层,用于制备任一类型丝网的彩色滤光器或用于制备等离子体显示器和场致发光显示器制备方法中的结构,用于制备光学开关、光学光栅(干涉光栅),用于通过聚集固化(在透明模具中的UV固化)或通过立体平板印刷方法制备三维物体,例如US4575330中所描述,用于制备复合材料(例如可含有玻璃纤维和/或其它纤维以及其它辅助剂的苯乙烯聚酯)和其它的厚涂层材料,用于电子元件的涂层或密封或光学纤维的涂层。该组合物也适于制备光学透镜,如隐形眼镜和菲涅耳透镜,以及制备医疗器械、辅助装置或移植物。
实施例
1.制备二酰基氧化膦二聚体.(BAPO)
[苯基-(2,4,6-三甲基苯甲酰基)膦基]-{2,4,6-三甲基-3-[苯基-(2,4,6-三甲基苯甲酰基)膦烷(phosphinoane)羰基]苯基}甲酮
通式I,R1=苯基,R2=2,4,6-三甲苯基,Q=1,3,5-三甲基苯,n=1,m=1
120ml(0.191mol)丁基锂(buthyllitium)在-20℃滴入到10.0g(0.091mol)苯膦的150ml四氢呋喃溶液中。获得黄色的悬浮液。随后在0℃逐滴地加入用50ml四氢呋喃稀释的11.2g(0.0455mol)的2,4,6-三甲基苯-1,3-二甲酸二氯化物。反应混合物在搅拌下在该温度保持30分钟。随后逐滴地加入16.6g(0.091mol)的2,4,6-三甲基苯甲酰氯并在相同的温度搅拌2小时。随后反应混合物升至室温。溶剂被旋转蒸发。残余物溶解于200ml甲苯中。该溶液用水稀释并分层。10.3g(0.091mol;30%)过氧化氢加入到有机相中。搅拌2小时后,有机相用水和饱和NaHCO3水溶液洗涤,经MgSO4干燥并过滤。蒸发和闪蒸柱色谱法(洗脱剂:己烷/乙酸乙酯3∶1)得到题列化合物,为黄色粘性树脂。
31 P-NMR 8.30ppm
1 H-NMR(ppm)7.72-7.80(m),7.45-7.47(m),6.76(s),6.62-6.67(m),2.11(s),2.05(s),1.96(s)和1.89-1.92(d),在CDCl3中测定。
以下的BAPO可类似地进行制备。
2.制备单酰基氧化膦二聚体.(MAPO)
[3-(苄基异丁基膦烷羰基)-2,4,6-三甲基苯基]-(苄基异丁基膦基)甲酮
通式II,R1=异丁基,R3=苯甲基,Q=1,3,5-三甲基苯,n=1,m=1
120ml(0.191mol)丁基锂在-20℃滴入到8.2g(0.091mol)异丁基膦的150ml四氢呋喃溶液中。随后在0℃逐滴地加入用50ml四氢呋喃稀释的11.2g(0.0455mol)的2,4,6-三甲基苯-1,3-二甲酸二氯化物。反应混合物在搅拌下在该温度保持30分钟。随后逐滴地加入15.56g(0.091mol)的苄基溴并在相同的温度搅拌2小时。随后反应混合物升至室温。溶剂被旋转蒸发。残余物溶解于200ml甲苯中。该溶液用水稀释并分层。10.3g(0.091mol;30%)过氧化氢加入到有机相中。搅拌2小时后,有机相用水和饱和NaHCO3水溶液洗涤,经MgSO4干燥并过滤。蒸发和闪蒸柱色谱法(洗脱剂:己烷/乙酸乙酯3∶1)得到题列化合物,为粘性树脂。
31 P-NMR 40.04ppm
1 H-NMR(ppm)7.13-7.28(m),6.76(s),3.14-3.41(m),2.01-2.0(d),1,60-1.97(m)和0.89-0.95(q),在CDCl3中测定。
以下的MAPO可类似地进行制备。
3.制备环状二酰基氧化膦(BAPO)
2-氧代-2-苯基-2,5-异膦吲哚(isophosphindole)-1,3-二酮
通式VI,R1是苯基,U是间苯二酰基。
120ml(0.191mol)丁基锂在-20℃滴入到10.0g(0.091mol)苯膦的150ml四氢呋喃溶液中。获得黄色的悬浮液。随后在0℃逐滴地加入用50ml四氢呋喃稀释的18.4g(0.091mol)的邻苯二甲酰氯。反应混合物在该温度搅拌30分钟,逐渐地升至室温,同时再搅拌2小时。溶剂用旋转蒸发器蒸发,残余物用200ml甲苯稀释并用水洗涤。10.3g(0.091mol;30%)过氧化氢加入到有机相中。室温2小时后,分出有机相,用水和饱和NaHCO3水溶液洗涤,经MgSO4干燥并过滤。蒸发溶剂和闪蒸色谱法得到题列化合物。
应用实施例
重量(g) 产物 描述
30.0 Ebecryl 605 环氧丙烯酸酯(UCB)
10.0 Ebecryl 7100 氨基丙烯酸酯(UCB)
5.0 Ebecryl 40 丙氧基化的季戊四醇(UCB)
30.0 OTA 480 基于甘油衍生物的丙烯酸酯化
的三官能团化的低聚体(UCB)
24.0 TPGDA 三丙二醇二丙烯酸酯
0.5 Ebecryl 1360 硅六丙烯酸酯
0.5 Dow Corning 57 硅添加剂,Dow Corning
100.0 总的OPV制剂
用基于100%重量制剂的10%和8%浓度来研究光敏引发剂。
为了测定固化速度,制剂施用到白色纸板(400μm)上并暴露在120W/cm输出功率的中压汞灯的UV光下。制剂完全固化和没有径迹时的传送带速度等于固化速度。
结果如表1所示
表1
基质 白色纸板(400μm)
施用设备 (Erichsen)
层厚度 5μm
灯 1m.p.Hg 120W/cm(IST)
固化速度(m/min)
10%光敏引发剂 8%光敏引发剂
实施例1 90 50
实施例1.b 80 10
实施例2 30 15
为了测定光泽,制剂施用到粗纸板(400μm)上并利用120W/cm输出功率的中压汞灯的UV光以10m/min的传送带速度进行固化。样品暴露在TKL40/05型的灯下22小时后测量固化薄膜的光泽。
结果如表2所示
表2
基质 粗纸板
层厚度 100μm
灯 1m.p.Hg 120W/cm(IST),TLK40/05
固化速度 10m/min
设备 光泽:Haze-Gloss(Byk-Gardner)
光泽20°
10%光敏引发剂 8%光敏引发剂
实施例1 80.00 88.00
实施例1.b 88.00
实施例2 88.00 84.00
Claims (10)
2.通式II的MAPO化合物的二聚体和多聚体形式
其中
R1和R3相互独立地是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;
Q是2-3价或4价的亚芳基;
n是1-4,m是0-2,n+m是2、3或4;
条件是R1和R3相互不同。
5.通式VI或VII的BAPO化合物的环状形式
其中
R1是未取代的或取代的C1-C12烷基、苄基、C1-C12烷氧基、C3-C6环烷基或C5-C14芳基;
U是2价的亚芳基和U′是4价的亚芳基。
8.根据权利要求3、6或7中任一项的方法,其中M是Li,该方法在-20至80℃于惰性气氛中进行。
9.根据权利要求1、2或4中任一项的化合物,其中n是1和m是1。
10.光聚合组合物,包括
(a)至少一种烯键式不饱和的光聚合化合物,和
(b)作为光敏引发剂的至少一种如上文所定义的通式I、II、VI或VII的化合物。
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CN108699173B (zh) * | 2016-02-25 | 2021-06-04 | 富士胶片株式会社 | 水性固化性组合物及水溶性光聚合引发剂 |
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TW303379B (zh) * | 1994-03-02 | 1997-04-21 | Ciba Sc Holding Ag | |
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GB2360283B (en) * | 2000-02-08 | 2002-08-21 | Ciba Sc Holding Ag | Monoacylarylphosphines and acylphosphine oxides and sulphides |
GB2365430B (en) | 2000-06-08 | 2002-08-28 | Ciba Sc Holding Ag | Acylphosphine photoinitiators and intermediates |
CA2467576A1 (en) | 2001-11-20 | 2003-05-30 | Jean-Pierre Wolf | Multimer forms of acylphosphines and their derivatives |
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- 2003-06-03 DE DE60322388T patent/DE60322388D1/de not_active Expired - Lifetime
- 2003-06-03 JP JP2004511314A patent/JP2005529167A/ja active Pending
- 2003-06-03 CN CNB038134772A patent/CN1324037C/zh not_active Expired - Fee Related
- 2003-06-03 AT AT03740176T patent/ATE402183T1/de not_active IP Right Cessation
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- 2003-06-03 BR BR0312133-0A patent/BR0312133A/pt not_active Application Discontinuation
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- 2003-06-03 MX MXPA04011923A patent/MXPA04011923A/es not_active Application Discontinuation
- 2003-06-03 KR KR10-2004-7020102A patent/KR20050009744A/ko not_active Application Discontinuation
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CN100402538C (zh) * | 2006-06-28 | 2008-07-16 | 南通优尚化工有限公司 | 大分子型的多酰基氧化膦光引发剂及生产方法 |
CN104487462A (zh) * | 2012-07-24 | 2015-04-01 | 拉姆博松有限公司 | 光聚合方法及用于该光聚合方法的新颖的化合物 |
CN104487462B (zh) * | 2012-07-24 | 2016-11-23 | 拉姆博松有限公司 | 光聚合方法及用于该光聚合方法的新颖的化合物 |
US10273258B2 (en) | 2012-10-01 | 2019-04-30 | Eth Zuerich | Process for the preparation of acylphosphanes |
CN104703995A (zh) * | 2012-10-01 | 2015-06-10 | 瑞士联邦苏黎世技术大学 | 用于制备酰基磷烷的方法 |
CN111116777A (zh) * | 2013-07-08 | 2020-05-08 | Igm集团公司 | 液态双酰基氧化膦光引发剂 |
CN108350109A (zh) * | 2015-11-20 | 2018-07-31 | 富士胶片株式会社 | 光聚合引发剂及其制造方法、聚合性组合物、喷墨记录方法、以及酰基氧化膦化合物 |
US10941307B2 (en) | 2015-11-20 | 2021-03-09 | Fujifilm Corporation | Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound |
CN108350109B (zh) * | 2015-11-20 | 2021-04-27 | 富士胶片株式会社 | 光聚合引发剂及其制造方法、聚合性组合物、喷墨记录方法、以及酰基氧化膦化合物 |
US11898046B2 (en) | 2015-11-20 | 2024-02-13 | Fujifilm Corporation | Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound |
CN114728520A (zh) * | 2019-11-11 | 2022-07-08 | 富士胶片株式会社 | 活性能量射线固化型油墨及图像记录方法 |
CN114728520B (zh) * | 2019-11-11 | 2024-03-08 | 富士胶片株式会社 | 活性能量射线固化型油墨及图像记录方法 |
US11926746B2 (en) | 2019-11-11 | 2024-03-12 | Fujifilm Corporation | Active energy ray-curable ink and image recording method |
Also Published As
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WO2003104245A1 (en) | 2003-12-18 |
CN1324037C (zh) | 2007-07-04 |
AU2003274653A1 (en) | 2003-12-22 |
DE60322388D1 (de) | 2008-09-04 |
EP1511754B1 (en) | 2008-07-23 |
US7196228B2 (en) | 2007-03-27 |
US20050245768A1 (en) | 2005-11-03 |
CA2489246A1 (en) | 2003-12-18 |
KR20050009744A (ko) | 2005-01-25 |
JP2005529167A (ja) | 2005-09-29 |
MXPA04011923A (es) | 2005-03-31 |
EP1511754A1 (en) | 2005-03-09 |
BR0312133A (pt) | 2005-04-05 |
ATE402183T1 (de) | 2008-08-15 |
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