CN101679574A - 包括亚氨基二嗪二酮的辐射交联和热交联聚氨酯体系 - Google Patents
包括亚氨基二嗪二酮的辐射交联和热交联聚氨酯体系 Download PDFInfo
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- CN101679574A CN101679574A CN200880010496A CN200880010496A CN101679574A CN 101679574 A CN101679574 A CN 101679574A CN 200880010496 A CN200880010496 A CN 200880010496A CN 200880010496 A CN200880010496 A CN 200880010496A CN 101679574 A CN101679574 A CN 101679574A
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- ester
- acid
- polyurethane composition
- polymer plastic
- vinylformic acid
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 15
- 238000004132 cross linking Methods 0.000 title abstract description 7
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- 239000000203 mixture Substances 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
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- 230000005855 radiation Effects 0.000 claims abstract description 12
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- BKKVYNMMVYEBGR-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(Br)=C1Br BKKVYNMMVYEBGR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
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- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 4
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
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- 238000001723 curing Methods 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
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- C08G18/7887—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring having two nitrogen atoms in the ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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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- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
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Abstract
本发明涉及通过辐射和热作用交联固化的聚氨酯组合物，及其用于生产全息介质的用途。本发明的聚氨酯组合物包括：A)一种或多种含亚氨基噁二嗪二酮基团的多异氰酸酯，B)一种或多种多官能的异氰酸酯反应性化合物，C)一种或多种具有在暴露于光化辐射时与烯属不饱和化合物进行聚合反应的基团(辐射固化基团)的化合物，D)任选的一种或多种自由基稳定剂和E)一种或多种光引发剂。
Description
相关申请的交叉引用
本申请根据35U.S.C.§119(e)要求了2007年4月11日提交的临时申请序列号No.60/922,989的优先权。
发明领域
本发明涉及通过辐射和热作用交联固化的聚氨酯体系，和它用于生产全息介质的用途。
发明背景
在US 6,743,552中所述的全息介质的生产中，信息被贮存在聚合物层中，该聚合物层主要由基质聚合物和均匀地分布在其中的非常特殊的可聚合单体组成。该基质聚合物可以以聚氨酯为基础。一般来说它从NCO官能化预聚物开始制备，该预聚物用多元醇如聚醚或聚酯交联，其中形成尿烷。
然而，问题是此类全息介质的有效生产需要反应混合物的低粘度，但是另一方面，调整粘度的溶剂是不希望有的。附加的问题是在尿烷化下的固化常常持续太长的时间。
包括多异氰酸酯、多元醇和辐射固化化合物如光化学交联反应性稀释剂的体系在各自情况下从涂料技术的领域中获知(US 4,247,578，DE197 09 560)。所提及的多元醇组分主要是聚醚型或聚酯型多元醇或聚丙烯酸酯多元醇。然而，对于在低粘度下如何实现快速固化的指示则没有给出。
发明概述
本发明的目的是提供聚氨酯体系，它适合于生产全息照相存储介质的存储层，并且它在不含溶剂的状态下，具有较低的粘度和另外快速固化。
现在已发现，当含亚氨基噁二嗪二酮基团的多异氰酸酯用作基质聚合物的构造单元时，精确获得了基质聚合物与不饱和单体的优异相容性。
本发明涉及聚氨酯体系，它包括
A)含有亚氨基噁二嗪二酮基团的多异氰酸酯，
B)多官能的异氰酸酯反应性化合物，
C)具有在暴露于光化辐射时与烯属不饱和化合物进行聚合反应的基团(辐射固化基团)的化合物，
D)任选的自由基稳定剂和
E)光引发剂。
发明详述
在说明书和权利要求中使用的，包括在实施例中所使用的，并且除非另外特意规定，全部的数值可以被读作被词“约”修饰，即使该术语没有特意出现。同时，在这里列举的任何数值范围希望包括包含在其中的全部子范围。
可使用的组分A的多异氰酸酯本身是具有至少一个亚氨基噁二嗪二酮基团的全部NCO官能化化合物。
这些可以是芳族、芳脂族、脂族或脂环族的多异氰酸酯。另外还可以使用不含亚氨基噁二嗪二酮基团的单-、二-、三-或多-异氰酸酯。
此类异氰酸酯的基础是例如亚丁基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、异氟尔酮二异氰酸酯(IPDI)、1，8-二异氰酸根合-4-(异氰酸根合甲基)辛烷、2，2，4-和/或2，4，4-三甲基六亚甲基二异氰酸酯、异构的双(4，4’-异氰酸根合环己基)甲烷和它们的具有任何所需异构体含量的混合物、异氰酸根合甲基-1，8-辛烷二异氰酸酯、1，4-亚环己基二异氰酸酯、异构的环己烷二亚甲基二异氰酸酯、1，4-亚苯基二异氰酸酯、2，4-和/或2，6-甲苯二异氰酸酯、1，5-亚萘基二异氰酸酯、2，4’-或4，4’-二苯甲烷二异氰酸酯和/或三苯基甲烷4，4’，4”-三异氰酸酯是合适的。
具有尿烷、脲、碳化二亚胺、酰脲、异氰脲酸酯、脲基甲酸酯、缩二脲、噁二嗪三酮，脲二酮和/或亚氨基噁二嗪二酮结构的单体二-或三异氰酸酯的衍生物的使用也是可能的。
以上述类型的脂族和/或脂环族二-或三异氰酸酯为基础的多异氰酸酯的使用是优选的。
以组分A)的总量为基础，不含亚氨基噁二嗪二酮基团的异氰酸酯的比例优选不超过90wt％，特别优选不超过50wt％和非常特别优选不超过40wt％。
以六亚甲基二异氰酸酯为基础的含亚氨基噁二嗪二酮基团的多异氰酸酯是特别优选的。
以在本发明的多异氰酸酯中三聚物结构的总量为基础，亚氨基噁二嗪二酮基团的比例优选大于30mol％，特别优选大于35mol％，非常特别优选大于40mol％。
根据EP-A 0 798 299，具有较高亚氨基噁二嗪二酮比例的此类多异氰酸酯可通过相应异氰酸酯单体或不同单体的混合物在特殊催化剂存在下的三聚反应来获得。特别合适的催化剂是具有组成{M[nF-*(HF)m]}的氢(多)氟化物，其中m/n＞0并且M是具有n电荷的阳离子或n-价的有机基团。
组分A)的化合物的NCO基团也可用本领域技术人员通常本身已知的封闭剂来完全地或部分地封闭。
这些的例子是醇、内酰胺、肟、丙二酸酯、乙酰乙酸烷基酯、三唑、酚、咪唑、吡唑和胺，例如丁酮肟、二异丙胺、1，2，4-三唑、二甲基-1，2，4-三唑、咪唑、丙二酸二乙酯、乙酰乙酸乙酯、丙酮肟、3，5-二甲基吡唑、ε-己内酰胺、N-叔丁基苄基胺、环戊酮羧酸乙基酯或这些封闭剂的任何所希望的混合物。
具有平均至少1.5个异氰酸酯反应性基团/每分子的全部多官能化的异氰酸酯反应性化合物能够用于组分B)中。在本发明的上下文中的异氰酸酯反应性基团优选是羟基、氨基或巯基。
合适的多官能化的异氰酸酯反应性化合物是例如聚酯、聚醚、聚碳酸酯、聚(甲基)丙烯酸酯和/或聚氨酯多元醇。
合适的聚酯多元醇是例如线性聚酯二醇或支化的聚酯多元醇，它们按照已知的方式从脂族、脂环族或芳族二-或多羧酸或它们的酸酐与具有≥2的OH官能度的多元醇获得。
此类二-或多羧酸或酸酐的例子是琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、壬烷二甲酸、癸烷二甲酸、对苯二甲酸、间苯二酸、邻苯二甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸或偏苯三酸和酸酐，如邻苯二甲酸酐、偏苯三酸酐或琥珀酸酐、或它们彼此的任何所希望的混合物。
此类合适醇的例子是乙二醇、二-、三-或四甘醇、1，2-丙二醇、二-、三-或四丙二醇、1，3-丙二醇、1，4-丁二醇、1，3-丁二醇、2，3-丁二醇、1，5-戊二醇、1，6-己二醇、2，2-二甲基-1，3-丙二醇、1，4-二羟基环己烷、1，4-二羟甲基环己烷、1，8-辛二醇、1，10-癸二醇、1，12-十二烷二醇、三羟甲基丙烷、甘油或它们彼此的任何所希望的混合物。
聚酯多元醇也能够以天然原料如蓖麻油为基础。对于以内酯的均聚物或共聚物为基础的聚酯多元醇来说，还有可能优选通过内酯或内酯混合物如丁内酯、ε-己内酯和/或甲基-ε-己内酯与例如上述类型的羟基官能化化合物如具有≥2的OH官能度的多元醇的加成反应来获得。
此类聚酯多元醇优选具有400-4000g/mol，特别优选500-2000g/mol的数均摩尔质量。它们的OH官能度优选是1.5-3.5，特别优选1.8-3.0。
合适的聚碳酸酯多元醇按照本身已知的方法通过有机碳酸酯或光气与二醇或二醇混合物反应来获得。
合适的有机碳酸酯是碳酸二甲基、二乙基和二苯基酯。
合适的二醇或二醇混合物包括相对于聚酯链段本身提到的并具有≥2的OH官能度的多元醇，优选1，4-丁二醇、1，6-己二醇和/或3-甲基戊二醇。
此类聚碳酸酯多元醇优选具有400-4000g/mol，特别优选500-2000g/mol的数均摩尔质量。这些多元醇的OH官能度优选是1.8-3.2，特别优选1.9-3.0。
合适的聚醚多醇是环醚与OH-或NH-官能化引发剂分子的加聚物，该加聚物任选具有嵌段结构。
合适的环醚是例如氧化苯乙烯、环氧乙烷、环氧丙烷、四氢呋喃、环氧丁烷、表氯醇和它们的任何所需的混合物。
可以使用的引发剂是相对于聚酯链段本身提到的并具有≥2的OH官能度的多元醇，以及伯或仲胺和氨基醇。
此类聚醚多醇优选具有250-10000g/mol，特别优选500-4000g/mol和非常特别优选600-2000g/mol的数均摩尔质量。该OH官能度优选是1.5-4.0，特别优选1.8-3.0。
另外，具有低分子量(即低于500g/mol的分子量)并且是短链(即含有2-20个碳原子)的脂族、芳脂族或脂环族二-、三-或多官能醇也适合作为组分B)的成分的多官能化的异氰酸酯反应性化合物。
这些可以是例如乙二醇、二甘醇、三甘醇、四甘醇、二丙二醇、三丙二醇、1，2-丙二醇、1，3-丙二醇、1，4-丁二醇、新戊二醇、2-乙基-2-丁基丙二醇、三甲基戊二醇、二乙基辛二醇位置异构体、1，3-丁二醇、环己烷二醇、1，4-环己烷二甲醇、1，6-己二醇、1，2-和1，4-环己烷二醇、氢化双酚A(2，2-双(4-羟基环己基)丙烷)、2，2-二甲基-3-羟丙酸2，2-二甲基-3-羟丙基酯。合适三醇的例子是三羟甲基乙烷、三羟甲基丙烷或甘油。具有更高官能度的合适醇是双三羟甲基丙烷、季戊四醇、二季戊四醇或山梨糖醇。
也合适的是氨基醇，例如乙醇胺、二乙醇胺、2-(N，N-二甲基氨基)乙基胺、N-甲基二乙醇胺、N-甲基二异丙醇胺、N-乙基二乙醇胺、N-乙基二异丙醇胺、N，N′-双(2-羟乙基)-全氢吡嗪、N-甲基双(3-氨基丙基)胺、N-甲基双(2-氨基乙基)胺、N，N′，N”-三甲基二亚乙基三胺、N，N-二甲基氨基乙醇、N，N-二乙基氨基乙醇、1-N，N-二乙基氨基-2-氨基乙烷、1-N，N-二乙基氨基-3-氨基丙烷、2-二甲基氨基甲基-2-甲基-1，3-丙二醇、N-异丙基二乙醇胺、N-丁基-二乙醇胺、N-异丁基二乙醇胺、N-油基二乙醇胺、N-硬脂基二乙醇胺、氧乙基化的椰油脂肪胺、N-烯丙基二乙醇胺、N-甲基二异丙醇胺、N，N-丙基二异丙醇胺、N-丁基二异丙醇胺和/或N-环己基-二异丙醇胺。
在组分C)中，α，β-不饱和羧酸衍生物，如丙烯酸酯、甲基丙烯酸酯、马来酸酯、富马酸酯、马来酰亚胺、丙烯酰胺和此外乙烯基醚、丙烯醚、烯丙基醚和含有二环戊二烯基单元的化合物和烯属不饱和化合物，如苯乙烯、α-甲基苯乙烯、乙烯基甲苯、乙烯基咔唑，烯烃，例如1-辛烯和/或1-癸烯，乙烯基酯，例如从Shell获得的如/或
(甲基)丙烯腈、(甲基)丙烯酰胺、甲基丙烯酸、丙烯酸和它们的任何所需混合物都可以使用。丙烯酸酯和甲基丙烯酸酯是优选的，并且丙烯酸酯是特别优选的。
丙烯酸或甲基丙烯酸的酯泛指丙烯酸酯或甲基丙烯酸酯。可使用的丙烯酸酯和甲基丙烯酸酯的例子是丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸乙氧基乙基酯、甲基丙烯酸乙氧基乙基酯、丙烯酸正丁酯、甲基丙烯酸正丁基酯、丙烯酸叔丁基酯、甲基丙烯酸叔丁基酯、丙烯酸己基酯、甲基丙烯酸己基酯、丙烯酸2-乙基己基酯、甲基丙烯酸2-乙基己基酯、丙烯酸丁氧基乙基酯、甲基丙烯酸丁氧基乙基酯、丙烯酸月桂基酯、甲基丙烯酸月桂酯、丙烯酸异冰片基酯、甲基丙烯酸异冰片基酯、丙烯酸苯基酯、甲基丙烯酸苯基酯、丙烯酸对-氯苯基酯、甲基丙烯酸对-氯苯基酯、丙烯酸对-溴苯基酯、甲基丙烯酸对-溴苯基酯、丙烯酸三氯苯基酯、甲基丙烯酸三氯苯基酯、丙烯酸三溴苯基酯、甲基丙烯酸三溴苯基酯、丙烯酸五氯苯基酯、甲基丙烯酸五氯苯基酯、丙烯酸五溴苯基酯、甲基丙烯酸五溴苯基酯、丙烯酸五溴苄基酯、甲基丙烯酸五溴苄基酯、丙烯酸苯氧基乙基酯、甲基丙烯酸苯氧基乙基酯、丙烯酸苯氧基乙氧基乙基酯、甲基丙烯酸苯氧基乙氧基乙基酯、丙烯酸2-萘基酯、甲基丙烯酸2-萘基酯、丙烯酸1，4-双-(2-硫萘基)-2-丁基酯、甲基丙烯酸1，4-双-(2-硫萘基)-2-丁基酯、双酚A二丙烯酸酯、双酚A二甲基丙烯酸酯、四溴双酚A二丙烯酸酯、四溴双酚A二甲基丙烯酸酯、丙烯酸2，2，2-三氟乙基酯、甲基丙烯酸2，2，2-三氟乙基酯、丙烯酸1，1，1，3，3，3-六氟异丙基酯、甲基丙烯酸1，1，1，3，3，3-六氟异丙基酯、丙烯酸2，2，3，3，3-五氟丙基酯和/或甲基丙烯酸2，2，3，3，3-五氟丙基酯。
也适合作为组分C)的环氧丙烯酸酯能够作为双酚A二缩水甘油醚与(甲基)丙烯酸羟烷基酯和羧酸的反应产物获得，该双酚A二缩水甘油醚首先在路易斯酸的催化下与(甲基)丙烯酸羟烷基酯进行反应，然后该羟基官能化的反应产物通过本领域技术人员已知的方法用羧酸加以酯化。双酚A二缩水甘油醚本身和溴化的变型，例如四溴双酚A二缩水甘油醚(来自Dow Chemical，D.E.R.542)，能够有利地用作双环氧化物。如上所述的全部羟基官能化丙烯酸酯能够用作(甲基)丙烯酸羟烷基酯，尤其是丙烯酸2-羟乙基酯、丙烯酸羟丙基酯、丙烯酸4-羟丁基酯、聚(ε-己内酯)单(甲基)丙烯酸酯和聚(乙二醇)单(甲基)丙烯酸酯。全部单官能羧酸原则上均适合作为该羧酸，尤其具有芳族取代基的那些。丙烷-2，2-二基双[(2，6-二溴-4，1-亚苯基)氧基(2-{[3，3，3-三(4-氯苯基)丙酰基]氧基}丙烷-3，1-二基)氧基乙烷-2，1-二基]二丙烯酸酯已经被证明是这一类型的环氧丙烯酸酯的优选化合物。
适合于组分C)的乙烯基芳族烃是苯乙烯，苯乙烯的卤化衍生物，例如2-氯苯乙烯、3-氯苯乙烯、4-氯苯乙烯、2-溴苯乙烯、3-溴苯乙烯、4-溴苯乙烯、对-(氯甲基)苯乙烯、对-(溴甲基)苯乙烯或1-乙烯基萘、2-乙烯基萘、2-乙烯基蒽、N-乙烯基吡咯烷酮、9-乙烯基蒽、9-乙烯基咔唑或双官能化合物，如二乙烯基苯。乙烯基醚，例如丁基乙烯基醚，也是合适的。
组分C)的优选化合物是9-乙烯基咔唑、乙烯萘、双酚A二丙烯酸酯、四溴双酚A二丙烯酸酯、丙烯酸1，4-双-(2-硫萘基)-2-丁基酯、丙烯酸五溴苯基酯、丙烯酸萘基酯和二丙烯酸丙烷-2，2-二基双[(2，6-二溴-4，1-亚苯基)氧基(2-{[3，3，3-三(4-氯苯基)丙酰基]-氧基}丙烷-3，1-二基)氧基乙烷-2，1-二基]酯。
一种或多种自由基稳定剂用作组分D)。描述在“Methoden derorganischen Chemie[Methods of Organic Chemistry]”(Houben-Weyl)，第4版，XIV/1卷，433及其后各页，Georg Thieme Verlag，Stuttgart 1961中的抑制剂和抗氧化剂是合适的。合适种类的物质是例如酚，如2，6-二叔丁基-4-甲基苯酚、甲酚、氢醌，苄醇，如二苯基甲醇，任选还有醌，例如2，5-二叔丁基氢醌，任选还有芳族胺，如二异丙基胺或吩噻嗪。优选的自由基稳定剂是2，6-二叔丁基-4-甲基苯酚、吩噻嗪和二苯基甲醇。
一种或多种光引发剂用作组分E)。这些通常是能够被光化辐射活化和引发相应的可聚合基团的自由基聚合的引发剂。光引发剂是本身已知的商购化合物，在单分子(类型I)和双分子(类型II)引发剂之间有区别。(类型I)体系是例如芳族酮化合物，例如二苯甲酮，它与叔胺结合，烷基二苯甲酮，4，4’-双(二甲基氨基)二苯甲酮(Michler酮)，蒽酮和卤化二苯甲酮或所述类型的混合物。(类型II)引发剂，如苯偶姻和它的衍生物，苄基缩酮，酰基膦氧化物，例如2，4，6-三甲基苯甲酰基二苯基膦氧化物，双酰基膦氧化物，乙醇酸苯基酯，樟脑醌，α-氨基烷基苯基酮，α，α-二烷氧基乙酰苯，1-[4-(苯硫基)苯基]辛烷-1，2-二酮-2-(O-苯甲酰肟)和α-羟烷基苯基酮，此外是合适的。描述在EP-A 0223587中的并由芳基硼酸铵和一种或多种染料的混合物组成的光引发剂体系也能够用作光引发剂。例如，三苯基己基硼酸四丁基铵、三-(3-氟苯基)己基硼酸四丁基铵和三-(3-氯-4-甲基苯基)己基硼酸四甲基铵适合作为芳基硼酸铵。合适的染料是例如新亚甲基蓝、劳思氏紫、碱性黄、氯化频哪氰醇、若丹明6G、陪花青、乙基紫、维多利亚蓝R、天青石蓝、甲基氮萘红、结晶紫、亮绿、Astrazon橙G、达罗红、派若宁Y、碱性红29、吡喃翁(pyrillium)I、花青、亚甲基蓝和天蓝A。
还有利的是使用这些化合物的混合物。取决于用于固化的辐射源，类型和浓度必须按照本领域技术人员已知的方式与光引发剂相适应。更多细节已描述在例如P.K.T.Oldring(编)，Chemistry &Technology of UV & EB Formulations For Coatings，Inks & Paints，vol.3，1991，SITA Technology，London，61-328页。
优选的光引发剂是2，4，6-三甲基苯甲酰基二苯基膦氧化物、1-[4-(苯硫基)苯基]辛烷-1，2-二酮-2-(O-苯甲酰肟)以及三(3-氟苯基)己基硼酸四丁基铵、三(3-氯-4-甲基苯基)己基硼酸四甲基铵与染料如亚甲基蓝、新亚甲基蓝、天蓝A、吡喃翁I、花青、陪花青、亮绿、结晶紫和劳思氏紫的混合物。
此外，一种或多种催化剂可以用于根据本发明的PU体系中。这些优选催化尿烷形成。胺和金属锡、锌、铁、铋、钼、钴、钙、镁和锆的金属化合物优选适合于这一目的。辛酸锡、辛酸锌、二月桂酸二丁锡、二羧酸二甲基锡、乙酰丙酮酸铁(III)、氯化铁(II)、氯化锌、四烷基铵氢氧化物、碱金属氢氧化物、碱金属醇盐、具有10-20个碳原子和任选的OH侧基的长链脂肪酸的碱金属盐、辛酸铅或叔胺如三乙基胺、三丁基胺、二甲基苄基胺、二环己基甲基胺、二甲基环己基胺、N，N，N′，N’-四甲基二氨基二乙基醚、双(二甲基-氨基丙基)脲、N-甲基-或N-乙基吗啉、N，N’-二吗啉代二乙基醚(DMDEE)、N-环己基吗啉、N，N，N′，N’-四甲基乙二胺、N，N，N′，N’-四甲基丁二胺、N，N，N′，N’-四甲基-1，6-己二胺、五甲基二亚乙基三胺、二甲基哌嗪、N-二甲基氨基乙基哌啶、1，2-二甲基咪唑、N-羟丙基咪唑、1-氮杂双环[2.2.0]辛烷、1，4-二氮杂双环[2.2.2]辛烷(Dabco)、或烷醇胺化合物如三乙醇胺、三异丙醇胺、N-甲基-和N-乙基二乙醇胺、二甲基氨基乙醇、2-(N，N-二甲基氨基乙氧基)乙醇、或N-三(二烷基氨基烷基)六氢三嗪，例如N，N’，N-三(二甲基氨基丙基)-s-六氢三嗪、二氮杂双环壬烷、二氮杂-双环十一烷、1，1，3，3-四甲基胍、1，3，4，6，7，8-六氢-1-甲基-2H-嘧啶并(1，2-a)嘧啶是特别优选的。
特别优选的催化剂是二月桂酸二丁锡、二羧酸二甲基锡、乙酰丙酮酸铁(III)、1，4-二氮杂双环[2.2.2]辛烷、二氮杂双环壬烷、二氮杂双环十一烷、1，1，3，3-四甲基胍和1，3，4，6，7，8-六氢-1-甲基-2H-嘧啶并(1，2-a)嘧啶。
另外，其它助剂和添加剂也可存在于根据本发明的PU体系中。这些是例如溶剂、增塑剂、流平剂、防沫剂或粘合促进剂，以及聚氨酯、热塑性聚合物、低聚物、和具有官能团例如缩醛、环氧化物、氧杂环丁烷、噁唑啉、二氧戊环和/或亲水基团例如盐和/或聚氧化乙烯的其它化合物。
优选使用的溶剂是与根据本发明的2组分配制剂具有良好相容性的易挥发性溶剂，例如乙酸乙酯、乙酸丁酯或丙酮。
具有良好溶解性能、低挥发性和高沸点的液体优选用作增塑剂；这些可以是例如己二酸二异丁酯、己二酸二正丁酯、邻苯二甲酸二丁基酯，非羟基官能化聚醚，例如具有250g/mol到2000g/mol的数均摩尔质量的聚乙二醇二甲基醚或聚丙二醇以及所述化合物的混合物。
也有利的是同时使用一种类型的多种添加剂。当然，也有利的是使用多种类型的多种添加剂。
组分B)-E)和任选的催化剂和助剂和添加剂的混合物通常由以下组分组成：
24.999-99.899wt％的组分B)
0.1-75wt％的组分C)
0-3wt％的组分D)
0.001-5wt％的组分E)
0-4wt％的催化剂
0-50wt％的助剂和添加剂。
混合物优选由以下组分组成：
86.998-97.998wt％的组分B)
2-13wt％的组分C)
0.001-1wt％的组分D)
0.001-1wt％的组分E)
0-2wt％的催化剂
0-15wt％的助剂和添加剂。
混合物同样优选由以下组分组成：
44.8-87.8wt％的组分B)
12.5-55wt％的组分C)
0.1-3wt％的组分D)
0.1-3wt％的组分E)
0-3wt％的催化剂
0-50wt％的助剂和添加剂。
NCO与OH的摩尔比典型地是0.5-2.0，优选0.90-1.25。
根据本发明的PU体系通常通过一种程序来获得，其中首先，除多异氰酸酯A)之外的所有组分彼此混合在一起。这能够通过混合技术领域技术人员本身已知的全部方法和装置来实现，例如搅拌容器或动态和静态混合器。在这一程序中的温度是0-100℃，优选10-80℃，特别优选20-60℃。该混合物能够立即进一步加工或能够作为贮存稳定的中间体贮存，任选几个月。
如果需要，也能够在例如1毫巴的真空下进行脱气。
与多异氰酸酯组分A)的混合是在应用之前不久进行的，它同样地有可能使用通常的混合技术。然而，没有任何死空间或有仅仅小的死空间的装置是优选的。此外，其中混合是在非常短的时间内进行且两种混合组分进行非常剧烈混合的方法是优选的。动态混合器，尤其其中组分A)和B)至E)首先在混合器中彼此接触的那些特别适合于这一目的。该混合能够在0-80℃的温度下，优选在5-50℃，特别优选10-40℃下进行。两种组分A和B的混合物能够任选地也在混合之后在例如1毫巴的真空下脱气，以便除去残留气体和防止在聚合物层中形成气泡。该混合得到澄明的液体配制剂，后者(取决于组成)在室温下几秒到几个小时内固化。
根据本发明的PU体系优选加以调节，使得在室温下的固化在几分钟到1个小时之内开始。在优选的实施方案中，通过在混合之后将配制剂加热到在30-180℃之间，优选40-120℃，特别优选50-100℃之间的温度来加速固化。
紧接着在全部组分的混合之后，根据本发明的聚氨酯体系具有典型地10-100000mPa·s，优选100-20000mPa·s，特别优选200-10000mPa·s，尤其优选500-1500mPa·s的室温粘度，使得它们甚至以无溶剂的形式具有非常良好的加工性能。在具有合适溶剂的溶液中，能够获得小于10000mPa·s，优选小于2000mPa·s，特别优选小于500mPa·s的室温粘度。
以15g的量和具有0.004％的催化剂含量的在4小时内固化的或以0.02％的催化剂含量在小于10分钟固化的体系已证明是有利的。
本发明此外涉及可从根据本发明的PU体系获得的聚合物。
这些优选具有低于-10℃，优选低于-25℃和特别优选低于-40℃的玻璃化转变温度。
根据优选的方法，本发明的配制剂直接在混合之后被施涂于基材上，有可能使用在涂料技术领域的技术人员已知的全部常用方法；尤其，涂料能够通过刮刀涂布、浇铸、刷涂、丝网印刷、喷涂或喷墨式印刷来施涂。
基材可以是塑料、金属、木材、纸、玻璃、陶瓷和包括多种这些材料的复合材料，在优选的实施方案中基材具有片形。
在优选的实施方案中，基材用配制剂的涂布是以连续方法进行的。一般来说，本发明的配制剂作为具有5mm-1μm，优选500μm-5μm，特别优选50μm-8μm和非常特别优选25μm-10μm的厚度的膜被施涂到基材上。
在片材作为基材的情况下，获得柔性、涂布的片材，在连续方法的情况下，该片材能够在固化之后卷起并因此可以贮存几个月。
在另外优选的实施方案中，配制剂被施涂以便它在两面上被透明基材尤其塑料或玻璃覆盖，为此目的配制剂被倾倒在保持在1-2mm，优选1.2-1.8mm，特别优选1.4-1.6mm，尤其1.5mm的准确间距的两个基材之间，并且基材在该准确间距一直保持到配制剂已经完全地固化和不能再流动为止。
用作基材的材料当然能够具有多个层。有可能的是基材由多种不同材料的多个层组成并且同时它另外具有例如涂层，该涂层具有附加性能，如改进的粘合性、增强的疏水性或亲水性能、改进的抗划性、在某些波长范围内的抗反射性能、改进的表面均匀性等等。
由所述方法中的一种获得的材料然后能够用于全息图的记录。为此目的，通过全息摄影术领域技术人员已知的方法引起两个光束在材料中发生干涉(P.Hariharan，Optical Holography，第2版，CambridgeUniversity Press，1996)，由此形成全息图。全息图的曝光能够同时通过连续辐射和通过脉冲辐射来进行。任选还有可能通过在同一种材料中和在同一点上的曝光来产生一个以上的全息图，有可能使用例如全息摄影术领域技术人员已知的角度倍加方法。在全息图曝光之后，材料能够任选也曝光于强烈的宽谱带光源，并且然后就可使用该全息图，无需另外的必需的加工步骤。该全息图能够任选地通过另外的加工步骤来进一步加工，例如转移到另一个基材上，变形，插入模塑，粘合剂粘结到另一个表面上，或被耐划的涂层所覆盖。
由所述方法中的一种生产的全息图能够用于数据存储，用于图像的显示(该图像例如用于人或物体的三维显示和用于人或物体的认证)，用于具有透镜、镜子、滤光器、漫射屏、衍射元件、光波导管和/或掩模的功能的光学元件的生产。
本发明因此另外涉及根据本发明的PU体系在全息介质的生产中的用途，和涉及该全息介质本身。
实施例：
在没有尿烷化催化剂(组分B5)的情况下测量各配制剂的粘度。全部的粘度通过使用锥板粘度计(Anton Paar MCR 51牌，在增大剪切速率10-1000/秒的情况下的粘度)在23℃下测量。
在各情况下固化时间由下列方法测定：
称量15克的没有尿烷化催化剂(组分B5)的各配制剂加入到聚乙烯塑料容器中，并利用合适的混合器完全地混合。其后，尿烷化催化剂(组分B5)被添加进去并且同样地完全混入其中。其后，将金属弓插入混合物中，从混合物中拔出并每隔一定间隔再次插入，直至不再可能从固化混合物中将金属弓拔出为止。固化时间被取作在催化剂添加与发现金属弓不再能够从该材料中拔出之间的时间。
在表中列出的数值表明，本发明的配制剂G和H具有总体最有利的性能组合，其中包括低粘度和短的固化时间。
Claims (9)
1.聚氨酯组合物，包括
A)一种或多种含亚氨基噁二嗪二酮基团的多异氰酸酯，
B)一种或多种多官能的异氰酸酯反应性化合物，
C)一种或多种具有在暴露于光化辐射时与烯属不饱和化合物进行聚合反应的基团(辐射固化基团)的化合物，
D)任选的一种或多种自由基稳定剂和
E)一种或多种光引发剂。
2.根据权利要求1的聚氨酯组合物，其中至少60wt％的组分A的多异氰酸酯是以脂族和/或脂环族二-和/或三异氰酸酯为基础的。
3.根据权利要求1的聚氨酯组合物，其中选自9-乙烯基咔唑、乙烯基萘、双酚A二丙烯酸酯、四溴双酚A二丙烯酸酯、丙烯酸1，4-双(2-硫萘基)-2-丁基酯、丙烯酸五溴苯基酯、丙烯酸萘基酯和二丙烯酸丙烷-2，2-二基双[(2，6-二溴-4，1-亚苯基)氧基(2-{[3，3，3-三(4-氯苯基)丙酰基]氧基}丙烷-3，1-二基)氧基乙烷-2，1-二基]酯中的一种或多种化合物用于C)中。
4.根据权利要求1的聚氨酯组合物，其中NCO与OH基团的摩尔比是0.90到1.25。
5.从根据权利要求1的聚氨酯组合物制备的聚合物塑料。
6.根据权利要求5的聚合物塑料，其中聚合物塑料是层或模塑制品。
7.根据权利要求5或6的聚合物塑料，其中聚合物塑料具有低于-40℃的玻璃化转变温度。
8.包括根据权利要求1的聚氨酯组合物的全息介质。
9.包括根据权利要求5的至少一种聚合物塑料的全息介质。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US92298907P | 2007-04-11 | 2007-04-11 | |
| US60/922,989 | 2007-04-11 | ||
| PCT/EP2008/002466 WO2008125201A1 (en) | 2007-04-11 | 2008-03-28 | Radiation-crosslinking and thermally crosslinking pu systems comprising iminooxadiazinedione |
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| Publication Number | Publication Date |
|---|---|
| CN101679574A true CN101679574A (zh) | 2010-03-24 |
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| CN200880010496A Pending CN101679574A (zh) | 2007-04-11 | 2008-03-28 | 包括亚氨基二嗪二酮的辐射交联和热交联聚氨酯体系 |
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| EP (1) | EP2144942A1 (zh) |
| JP (1) | JP2010523775A (zh) |
| KR (1) | KR20100015468A (zh) |
| CN (1) | CN101679574A (zh) |
| BR (1) | BRPI0809619A2 (zh) |
| CA (1) | CA2683901A1 (zh) |
| IL (1) | IL200713A0 (zh) |
| RU (1) | RU2009141369A (zh) |
| TW (1) | TW200909465A (zh) |
| WO (1) | WO2008125201A1 (zh) |
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| CN111247181A (zh) * | 2017-12-11 | 2020-06-05 | 株式会社Lg化学 | 光聚合物组合物 |
| CN115322622A (zh) * | 2022-08-24 | 2022-11-11 | 山东布瑞特油墨有限公司 | 一种uv固化喷墨材料及其制备方法和应用 |
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- 2008-03-28 WO PCT/EP2008/002466 patent/WO2008125201A1/en active Application Filing
- 2008-03-28 EP EP08734841A patent/EP2144942A1/en not_active Withdrawn
- 2008-03-28 CN CN200880010496A patent/CN101679574A/zh active Pending
- 2008-03-28 KR KR1020097021122A patent/KR20100015468A/ko not_active Application Discontinuation
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| CN111247181A (zh) * | 2017-12-11 | 2020-06-05 | 株式会社Lg化学 | 光聚合物组合物 |
| US11591433B2 (en) | 2017-12-11 | 2023-02-28 | Lg Chem, Ltd. | Photopolymer composition |
| CN111247181B (zh) * | 2017-12-11 | 2023-03-21 | 株式会社Lg化学 | 光聚合物组合物 |
| CN115322622A (zh) * | 2022-08-24 | 2022-11-11 | 山东布瑞特油墨有限公司 | 一种uv固化喷墨材料及其制备方法和应用 |
| CN115322622B (zh) * | 2022-08-24 | 2023-03-31 | 山东布瑞特油墨有限公司 | 一种uv固化喷墨材料及其制备方法和应用 |
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| KR20100015468A (ko) | 2010-02-12 |
| TW200909465A (en) | 2009-03-01 |
| EP2144942A1 (en) | 2010-01-20 |
| IL200713A0 (en) | 2010-05-17 |
| JP2010523775A (ja) | 2010-07-15 |
| RU2009141369A (ru) | 2011-05-20 |
| CA2683901A1 (en) | 2008-10-23 |
| WO2008125201A1 (en) | 2008-10-23 |
| US20080311482A1 (en) | 2008-12-18 |
| BRPI0809619A2 (pt) | 2014-09-16 |
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