CN107074796B - 四氢呋喃衍生物 - Google Patents
四氢呋喃衍生物 Download PDFInfo
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- CN107074796B CN107074796B CN201580056702.4A CN201580056702A CN107074796B CN 107074796 B CN107074796 B CN 107074796B CN 201580056702 A CN201580056702 A CN 201580056702A CN 107074796 B CN107074796 B CN 107074796B
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 36
- 239000011248 coating agent Substances 0.000 claims abstract description 30
- 239000000758 substrate Substances 0.000 claims abstract description 30
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- 239000004033 plastic Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 239000008199 coating composition Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 238000003847 radiation curing Methods 0.000 claims description 13
- 238000001723 curing Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 30
- 239000000049 pigment Substances 0.000 description 25
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 21
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Paints Or Removers (AREA)
- Furan Compounds (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
本发明涉及式(I)的四氢呋喃衍生物,其中基团R1定义为(CH2=CH‑CO‑O‑(CHR3‑CH2‑O)m‑CH2)‑且基团R2定义为(CH2=CH‑CO‑O‑(CHR4‑CH2‑O)n‑CH2)‑,其中基团R3和R4各自独立地为氢或甲基,条件是m和n的总和为0‑20的数。化合物(I)适合涂敷固体基材的表面,尤其是涂敷塑料。
Description
发明领域
本发明涉及适合涂敷固体基材表面,尤其是塑料表面的具有特定结构的四氢呋喃衍生物。
现有技术
EP-A-043,448描述了2,5-二羟甲基四氢呋喃的二甲基丙烯酸酯。根据第4页第13-14行的公开内容,这些化合物为具有高粘度的物质。这些化合物用作在没有氧气存在下硬化的密封剂和/或粘合剂的必要成分。
DE-A-10,2010,044,206描述了一种生产基于丙氧基化甘油的可辐射固化(甲基)丙烯酸酯的方法。首先使(甲基)丙烯酸与三-四丙氧基化甘油反应,然后通过含水萃取从所得反应混合物中除去过量(甲基)丙烯酸。
DE-A-10,2010,044,206描述了一种生产基于丙氧基化甘油的可辐射固化(甲基)丙烯酸酯的方法。首先使(甲基)丙烯酸与2.9-4倍乙氧基化甘油反应,然后通过与至少一种官能度至少为2的芳族或脂族环氧化物反应而从所得反应混合物中除去过量(甲基)丙烯酸。
发明描述
本发明的目的是要提供适合涂敷固体基材,尤其是塑料的表面的物质,其中涂层通过辐射固化,更具体使用UV光固化。固化的涂层,尤其是UV固化的涂料应具有高硬度。
开发的物质尤其应满足所有下面三个标准:
(1)物质自身的粘度应低于500mPas(用Brookfield粘度计在25℃和1000s-1的剪切速率下按照DIN EN ISO 3219/A.3测量)。
(3)对塑料的附着力应为0-2,优选0或1(通过DIN EN ISO 2409划格法测量,其中G值根据学习成绩系统位于0-5范围内,其中0为最好得分且5为最差得分)。
本发明首先提供了式(I)的四氢呋喃衍生物:
其中基团R1具有定义(CH2=CH-CO-O-(CHR3-CH2-O)m-CH2)-且基团R2具有定义(CH2=CH-CO-O-(CHR4-CH2-O)n-CH2)-,其中基团R3和R4相互独立地为氢或甲基,条件是m和n的总和为0-20的数。
因此,化合物(I)的表述为下列结构(A):
根据式(I),取代基R1和R2可以位于由5员环所示基准面的相同侧上或不同侧上。换言之,化合物(I)可以以顺式或反式存在。因此,将这些异构体分别表示为顺式-2,5-R1-R2-四氢呋喃和反式-2,5-R1-R2-四氢呋喃。
在一个实施方案中,m和n的总和为4-15,更具体5-12的数。
化合物(I)本身可以通过化学家已知的所有方法制备。
优选化合物(I)按如下制备:使具有式(B)的2,5-二羟甲基四氢呋喃直接或者在事先乙氧基化和/或丙氧基化之后与丙烯酸反应:
这里的操作优选用过量丙烯酸在有机溶剂,尤其是环己烷或甲基环己烷中,以及在酸性酯化催化剂,更具体甲磺酸、硫酸或对甲苯磺酸存在下进行。
优选使用二醇(B)的工业混合物,其中顺式/反式(摩尔)比尤其位于95:5-5:95范围内。这里特别优选顺式/反式(摩尔)比为95:5-50:50,特别是95:5-80:20。
在酯化结束之后,除去所用溶剂,优选通过蒸馏,尤其是在减压下蒸馏。还除去过量丙烯酸,这可以通过各种方式进行,如通过蒸馏、萃取洗涤或化学方式进行。
若通过萃取洗涤除去过量丙烯酸,则使用下列程序:洗涤使用优选以含水介质萃取进行(就此而言例如比较DE-A-102010044206的相关公开内容)。
若通过清除化学除去过量丙烯酸,则使用下列程序:化学清除优选通过使过量丙烯酸与环氧化物,更具体的是官能度为至少2的环氧化物反应而完成(就此而言例如比较DE-A-10,2010,044204中的相关公开内容)。
本发明的另一主题是包含一种或多种式(I)的四氢呋喃衍生物的涂料组合物:
其中基团R1具有定义(CH2=CH-CO-O-(CHR3-CH2-O)m-CH2)-且基团R2具有定义(CH2=CH-CO-O-(CHR4-CH2-O)n-CH2)-,其中基团R3和R4相互独立地为氢或甲基,条件是m和n的总和为0-20的数。
在一个实施方案中,m和n的总和为4-15的数,更具体为5-12的数。
对于化合物(I)的制备,可以参考就通用说明和优选实施方案二者而言的上述说明。
若如上面观察那样通过清除化学除去过量丙烯酸,则使用下列程序:化学清除优选通过使过量丙烯酸与环氧化物,更具体的是官能度为至少2的环氧化物反应而完成(就此而言例如比较DE-A-10,2010,044204中的相关公开内容)。结果得到一种包含化合物(I)以及还有所得清除产物的组合物。组合物的用途
本发明的另一主题是化合物(I)在涂敷固体基材表面中的用途。这里对于基材本身的性质没有限制。
合适基材的实例例如为纺织品、皮革、金属、塑料、玻璃、木材、纸张或卡纸板。
在一个特别优选实施方案中,所述基材为塑料。
塑料—按照通常的语言用法—以及对于本说明书而言为有机聚合物固体。塑料通常分为三个主要组:热塑性塑料、热固性塑料和弹性体。在一般语言中,“塑料”为通称。塑料通常由有机单体分子或生物聚合物合成或半合成生产。
适合本发明涂料组合物的基材实例是热塑性聚合物,尤其是聚甲基丙烯酸甲酯、聚甲基丙烯酸丁酯、聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚偏二氟乙烯、聚氯乙烯、聚酯、聚烯烃、丙烯腈-乙烯-丙烯-二烯-苯乙烯共聚物(A-EPDM)、聚醚酰亚胺、聚醚酮、聚苯硫醚、聚苯醚或其混合物。
进一步可以提到聚乙烯、聚丙烯、聚苯乙烯、聚丁二烯、聚酯、聚酰胺、聚醚、聚碳酸酯、聚乙烯醇缩醛、聚丙烯腈、聚缩醛、聚乙烯醇、聚乙酸乙烯酯、酚醛树脂、脲树脂、密胺树脂、醇酸树脂、环氧树脂或聚氨酯,其嵌段共聚物或接枝共聚物,以及这些的共混物。
下列塑料可以作为优先合适的塑料提及:丙烯腈-丁二烯-苯乙烯(ABS)、聚丙烯腈/甲基丙烯酸甲酯(AMMA)、丙烯腈-苯乙烯-丙烯酸酯(ASA)、环氧树脂(EP)、发泡聚苯乙烯(EPS)、乙烯-乙酸乙烯酯共聚物(EVA)、高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)、甲基丙烯酸甲酯/丙烯腈/丁二烯/苯乙烯(MABS)、丙烯酸甲酯/丁二烯/苯乙烯共聚物(MBS)、密胺-甲醛树脂(MF)、聚酰胺(PA)、尼龙(PA6)、尼龙(PA66)、聚丙烯腈(PAN)、1,2-聚丁二烯(PB)、聚对苯二甲酸丁二醇酯(PBT)、聚碳酸酯(PC)、聚乙烯(PE)、氯化聚乙烯(PEC)、聚醚醚酮(PEEK)、聚醚酰亚胺(PEI)、聚醚酮(PEK)、聚芳基醚砜(PES)、聚对苯二甲酸乙二醇酯(PET)、苯酚-甲醛树脂(PF)、聚酰亚胺(PI)、聚异丁烯(PIB)、聚甲基丙烯酸甲酯(PMMA)、聚甲醛(POM)、聚丙烯(PP)、聚乙烯硫醚(PPS)、聚苯乙烯(PS)、聚砜(PSU)、聚氨酯(PUR)、聚乙酸乙烯酯(PVAC)、聚乙烯醇(PVAL)、聚氯乙烯(PVC)、聚偏二氯乙烯(PVDC)、苯乙烯-丙烯腈(SAN)、苯乙烯-丁二烯(SB)、脲-甲醛树脂(UF)、不饱和聚酯树脂UP塑料(按照DIN 7728的简码)和脂族聚酮。
特别优选的基材是聚烯烃,如PP(聚丙烯),其可以是全同立构的、间同立构的或无规立构的并且可以未取向或者通过单轴或双轴拉伸取向,SAN(苯乙烯-丙烯腈共聚物),PC(聚碳酸酯),PVC(聚氯乙烯),PMMA(聚甲基丙烯酸甲酯),PBT(聚对苯二甲酸丁二醇酯),PA(聚酰胺),ASA(丙烯腈-苯乙烯-丙烯酸酯共聚物)和ABS(丙烯腈-丁二烯-苯乙烯共聚物),以及还有其物理混合物(共混物)。特别优选PP、SAN、ABS、ASA以及还有ABS或ASA与PA或PBT或PC的共混物。
本发明的另一主题是包含一种或多种化合物(I)的涂料组合物在涂敷固体基材表面中的用途。这里对于基材本身的性质没有限制。在一个特别优选的实施方案中,所述基材是受到上面评述的塑料。
术语“涂料组合物”包括任何种类的施用于待涂敷基材表面并随后固化,任选在事先干燥之后固化的组合物。术语“涂料组合物”尤其包括所有种类的表面涂料。
正如熟练技术人员知晓的那样,“表面涂料”涉及可以为液体或粉状且以薄层薄薄地施用于制品,换言之,待涂敷基材,然后固化的涂料组合物。就此而言,也见下面有关术语“涂敷”的部分。
除了化合物(I)外,本发明的涂料组合物可以进一步包含其他典型涂料添加剂,实例是抗氧化剂、稳定剂、活化剂(促进剂)、填料、颜料、染料、抗静电剂、阻燃剂、增稠剂、触变剂、表面活性剂、粘度改性剂、增塑剂或配位剂。此外,除了化合物(I)外,本发明的涂料组合物还可以包含其他未被式(I)包括的可辐射固化组分。
除了自由基(共)聚合的(共)聚合物外,所考虑的增稠剂是常规有机和无机增稠剂如羟甲基纤维素或膨润土。
可以使用的配位剂例如包括乙二胺乙酸及其盐,以及还有β-二酮。
合适的稳定剂包括典型的UV吸收剂如草酰苯胺类、三嗪类和苯并三唑(后者可以作为牌号由Ciba-购得),以及二苯甲酮类。它们可以单独使用或者与合适的自由基清除剂一起使用,实例是位阻胺如2,2,6,6-四甲基哌啶、2,6-二叔丁基哌啶或其衍生物,例如癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯。稳定剂基于该制剂中存在的固体组分通常以0.1-5.0重量%的量使用。
颜料同样可以包括在涂料组合物中。根据CDChemie Lexikon–1.0版,Stuttgart/New York:Georg Thieme Verlag 1995,参考DIN 55943,颜料为颗粒状“彩色或非彩色的有机或无机着色剂,在应用介质中基本不溶”。“基本不溶”在这里是指在25℃下的溶解度低于1g/1000g应用介质,优选低于0.5g/1000g应用介质,更优选低于0.25g/1000g应用介质,非常优选低于0.1g/1000g应用介质,更具体低于0.05g/1000g应用介质。
若使用颜料,则应确保固化以电子束进行或者使用光引发剂,后者尽管着色,但可以通过引入的辐射活化—例如通过在其中颜料对引入的辐射足够透明的波长范围内显示出显著吸光度的光引发剂。在本发明的一个优选实施方案中,不使用颜料且将该涂料组合物用于透明清漆/透明涂层中。
颜料的实例包括任何所需体系的吸收颜料和/或效应颜料,优选吸收颜料。对颜料组分的数目和选择根本没有限制。它们可以根据需要适应特殊要求,例如所需的感知色。
效应颜料是所有呈现片状结构且给予表面涂层以特定装饰性颜色效果的颜料。效应颜料例如为所有通常可以用于汽车涂饰和工业涂饰的效应赋予颜料。该类效应颜料的实例是纯金属颜料,如铝、铁或铜颜料;干涉颜料,如二氧化钛涂敷云母、氧化铁涂敷云母、混合氧化物涂敷云母(例如用二氧化钛和Fe2O3或二氧化钛和Cr2O3)、金属氧化物涂敷铝或液晶颜料。
赋予颜色的吸收颜料例如为常规且可以用于涂料工业中的有机或无机吸收颜料。有机吸收颜料的实例是偶氮颜料以及酞菁、喹吖啶酮和吡咯并吡咯颜料。无机吸收颜料的实例是氧化铁颜料、二氧化钛和炭黑。
当涂料组合物的固化不是用电子束而是使用UV辐射进行时,优选存在至少一种能够引发烯属不饱和双键(C=C双键)的聚合的光引发剂。
非常一般地,可以使用对熟练技术人员而言适当已知的例如在相关技术出版物和单行本中所述种类的所有光引发剂。
所考虑的那些例如包括:
·单-或二酰基氧化膦,例如2,4,6-三甲基苯甲酰基二苯基氧化膦(来自BASF SE的TPO)、2,4,6-三甲基苯甲酰基苯基次膦酸乙酯(来自BASF SE的TPO L)、二(2,4,6-三甲基苯甲酰基)苯基氧化膦(来自Ciba的819),
·二苯甲酮类、羟基苯乙酮类、苯酰甲酸及其衍生物或这些光引发剂的混合物。实例包括下列:二苯甲酮,苯乙酮,乙酰萘醌,甲基乙基酮,苯戊酮,苯己酮,α-苯基苯丁酮,对吗啉代苯丙酮,二苯并环庚酮,4-吗啉代二苯甲酮,4-吗啉代脱氧苯偶姻,对二乙酰苯,4-氨基二苯甲酮,4’-甲氧基苯乙酮,β-甲基蒽醌,叔丁基蒽醌,蒽醌羧酸酯,苯甲醛,α-四氢萘酮,9-乙酰基菲,2-乙酰基菲,10-噻吨酮,3-乙酰基菲,3-乙酰基吲哚,9-芴酮,2,3-二氢-1-茚酮,1,3,4-三乙酰基苯,噻吨-9-酮,氧杂蒽-9-酮,2,4-二甲基噻吨酮,2,4-二乙基噻吨酮,2,4-二异丙基噻吨酮,2,4-二氯噻吨酮,苯偶姻,苯偶姻异丁基醚,氯代氧杂蒽酮,苯偶姻四氢吡喃基醚,苯偶姻甲基醚,苯偶姻乙基醚,苯偶姻丁基醚,苯偶姻异丙基醚,7H-苯偶姻甲基醚,苯并[de]蒽-7-酮,1-萘甲醛,4,4’-二(二甲氨基)二苯甲酮,4-苯基二苯甲酮,4-氯二苯甲酮,米蚩酮,1-萘乙酮,2-萘乙酮,1-苯甲酰基环己烷-1-醇,2-羟基-2,2-二甲基苯乙酮,2,2-二甲氧基-2-苯基苯乙酮,2,2-二乙氧基-2-苯基苯乙酮,1,1-二氯苯乙酮,1-羟基苯乙酮,苯乙酮缩二甲醇,邻甲氧基二苯甲酮,三苯基膦,三邻甲苯基膦,苯并[a]蒽-7,12-二酮,2,2-二乙氧基苯乙酮,联苯酰缩酮类,如联苯酰缩二甲醇,2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙-1-酮,蒽醌类如2-甲基蒽醌、2-乙基蒽醌、2-叔丁基蒽醌、1-氯蒽醌、2-戊基蒽醌和2,3-丁二酮。
还合适的是苯基乙醛酸酯类型的非泛黄或泛黄光引发剂。
还可以使用不同光引发剂的混合物。典型混合物包括例如2-羟基-2-甲基-1-苯基丙-2-酮和1-羟基环己基苯基酮、二(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮、二苯甲酮和1-羟基环己基苯基酮、二(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦和1-羟基环己基苯基酮、2,4,6-三甲基苯甲酰基二苯基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮、2,4,6-三甲基二苯甲酮和4-甲基二苯甲酮或者2,4,6-三甲基二苯甲酮以及4-甲基二苯甲酮和2,4,6-三甲基苯甲酰基二苯基氧化膦。
合适的光引发剂为:
·2,4,6-三甲基苯甲酰基二苯基氧化膦,
·2,4,6-三甲基苯甲酰基苯基次膦酸乙酯,
·二(2,4,6-三甲基苯甲酰基)苯基氧化膦,
·二苯甲酮,
·1-苯甲酰基环己烷-1-醇,
·2-羟基-2,2-二甲基苯乙酮,和
·2,2-二甲氧基-2-苯基苯乙酮。
涂料组合物基于涂料组合物中存在的可固化组分总量优选以0.05-10重量%,更优选0.1-8重量%,更具体0.2-5重量%的量包含光引发剂。
对于本发明用途通过熟练技术人员已知的常规方法将固体基材的表面用四氢呋喃衍生物(I)涂敷,其中所需四氢呋喃衍生物(I)或包含一种或多种化合物(I)的涂料组合物以所需厚度施用于基材上并至少部分辐射固化。这里优选完全辐射固化。需要的话该操作可以重复一次或多次。对基材的施用可以以已知方式,例如通过喷涂、抹涂、刮涂、刷涂、轧滚、辊涂、浇注、层压、模内涂敷或共挤出,优选通过喷涂和辊涂进行。所用喷涂方法例如可以是压缩空气、无空气或静电喷涂方法。
正如熟练技术人员知晓的那样,辐射固化涉及通过电磁辐射和/或微粒辐射诱发的可聚合化合物的自由基聚合。优选使用UV光或电子束(电子束:150-300keV)。尤其优选波长为200-500nm,更具体为250-400nm的UV光。
优选设定涂层厚度以使得干膜厚度为30-200μm,优选50-150μm。正如熟练技术人员知晓的那样,干膜厚度涉及干燥或固化涂层的层厚。干燥的概念包括蒸发涂料组合物中存在的溶剂,如水或有机溶剂。固化的概念包括交联该涂料组合物。尤其可以强调的是干膜厚度的概念在这里纯粹基于表象应理解为干燥和/或固化涂层所具有的层厚。
需要的话,辐射固化可以在相对高的温度下进行。此时优选温度高于可辐射固化基料的Tg(Tg=玻璃化转变温度)。
辐射固化可以在含氧气氛下或者在惰性气体下进行,优选后者。
除了辐射固化外,可能涉及其他固化机理,例如热固化、水分固化、化学固化和/或氧化固化。
需要的话,若存在两个或更多个叠置施加涂料的涂层,则可以在各涂敷操作之后进行干燥和/或辐射固化。
适合辐射固化的辐射源的实例是低压汞发射器、中压汞发射器和高压发射器,以及还有荧光管、脉冲发射器、金属卤化物灯、激光器、脉冲灯(闪光灯)、卤素灯和电子闪光装置,借此可以在没有光引发剂下辐射固化,或准分子激光发射器。
还可以使用两个或更多个,例如2-4个辐照源来辐射固化。需要的话,这些源还可以各自在不同波长范围发射。
辐照任选还可以在没有氧气存在下,如在惰性气体气氛下进行。合适的惰性气体优选氮气、稀有气体、二氧化碳或燃烧气体。
本发明的另一主题按照上面所作说明是一种通过对固体基材表面施用四氢呋喃衍生物(I)或包含一种或多种化合物(I)的涂料组合物并随后进行辐射固化,更具体借助UV光进行辐射固化而涂敷固体基材表面的方法:
其中基团R1具有定义(CH2=CH-CO-O-(CHR3-CH2-O)m-CH2)-且基团R2具有定义(CH2=CH-CO-O-(CHR4-CH2-O)n-CH2)-,其中基团R3和R4相互独立地为氢或甲基,条件是m和n的总和为0-20的数。
“涂敷”涉及用于将牢固粘结层施用于工件–基材的表面的方法。该施用的层称为涂层。常规涂敷方法在涂料组合物的施用性质上区分为化学、机械、热和热机械方法。在本发明上下文中优选UV固化,其诱发存在于涂料组合物中的化合物(I)的化学交联。
实施例
测量和测试方法
粘度:物质本身的粘度使用Brookfield粘度计在25℃和1000s-1的剪切速率下按照DIN EN ISO 3219/A.3测量。
Erichsen杯突(Ew):Erichsen杯突为涂层弹性的度量。由待测试物质在固体基材表面上施用并通过UV辐射将其固化得到的涂层的Erichsen杯突根据DIN ISO 1520测量。Erichsen杯突以[mm]记录。
附着力(划格法附着力值=G值):对塑料的附着力通过根据DIN EN ISO 2409的划格法测定,其中G值根据学习成绩系统位于0-5的范围内。这里在标尺上0表示为最好得分且5表示最差得分。用于涂敷的塑料为Stamylan。
碘色数:碘色数使用Lange Lico 400仪器按照DIN 6162测量。
所用物质
TBABr:四丁基溴化铵(CAS号1643-19-2)
缩水甘油醚:季戊四醇二/三缩水甘油醚(CAS号30973-88-7),“Ipox CL 16”(来自Ipox)
THF-二醇:2,5-二羟甲基四氢呋喃;顺式/反式摩尔比为90:10的工业混合物。
THF-二醇-5.3PO:7.5mol THF-二醇与39.7mol氧化丙烯的反应产物。制备如下所述进行:在25℃下将995.0g THF-二醇和10.0g固体KOH加入5L反应器中。然后将该反应器用氮气惰性化。将该反应器加热至120℃并计量加入2300g氧化丙烯。反应4小时后将反应器在完全真空下于50℃下抽空30分钟,然后冷却至25℃。产物通过用离子交换材料(Ambosol)和水中和、真空蒸馏和过滤而后处理。所得产物为浅色液体。得到3313.4g产物。所得聚醚具有下列特征:
OH值:260mg KOH/g
粘度(25℃):152mPas
THF-二醇-7EO:7.5mol THF-二醇与52.3mol氧化乙烯的反应产物。在25℃下将990.0g THF-二醇和9.9g固体KOH加入5L反应器中。然后将该反应器用氮气惰性化。将该反应器加热至120℃并计量加入2300g氧化乙烯。反应4小时后将反应器在完全真空下于50℃下抽空30分钟,然后冷却至25℃。产物通过用离子交换材料(Ambosol)和水中和、真空蒸馏和过滤而后处理。所得产物为浅色液体。得到3240.3g产物。所得聚醚具有下列特征:
OH值:272mg KOH/g
粘度(25℃):314mPas
实施例
实施例1
THF-二醇二丙烯酸酯的制备
将115.35g(1.75mol OH)OH值为424mg KOH/g的THF-二醇、143.66g丙烯酸、86.33g环己烷和10.4g甲磺酸70%eq.在由0.26g Kerobit、0.78g甲基氢醌、0.27g次磷酸(50%eq.)和7.8mg吩噻嗪构成的稳定剂混合物存在下合并,该稳定剂混合物以在1.0g丙烯酸中的溶液存在,并将这些组分在90-95℃下酯化。在5小时内实现90%的转化率。然后在减压下除去环己烷和过量丙烯酸至酸值(AN)为4mg KOH/g物质。
粘度:27mPas
碘色数:42
实施例2
THF-二醇-7EO二丙烯酸酯
在500ml三颈烧瓶中将158.86g(0.72mol OH)THF-7EO、59.41g丙烯酸、86.33g甲基环己烷和6.5g浓硫酸在由1.0g Kerobit、4.36g甲基氢醌和4.36g次磷酸(50%eq.)构成的稳定剂混合物存在下合并且将这些组分在101-105℃下酯化。在6.5小时内实现78%的转化率。然后在减压下除去甲基环己烷和过量丙烯酸至酸值(AN)为53mg KOH/g物质。这之后在107-108℃下在TBABr(4g)催化下使用31.7g Ipox CL 16将残留丙烯酸转化成200g粗酯,直到酸值(AN)达到4.0,然后在Seitz K300过滤器上过滤产物。该产物—THF-二醇-7EO二丙烯酸酯和清除产物(即过量丙烯酸与Ipox CL 16反应的产物)的混合物—表征如下:
粘度:340mPas
碘色数:0.9
实施例3
制备THF-二醇-5.3PO二丙烯酸酯
在2000ml三颈烧瓶中将884.76g(4.0mol OH)THF-二醇-5.3PO、315.23g丙烯酸、400g甲基环己烷和8.1g甲磺酸(70%eq.)在由6.0g Kerobit、24.0g甲基氢醌和24.0g次磷酸(50%eq.)构成的稳定剂混合物存在下合并且将这些组分在101-105℃下酯化。在8小时内实现79%的转化率。然后在减压下除去甲基环己烷和过量丙烯酸至酸值(AN)为46mgKOH/g物质。这之后在107-108℃下在TBABr(25.71g)催化下使用155.3g Ipox CL 16将残留丙烯酸转化至AN为3.9,然后在Seitz K300过滤器上过滤产物。产物—THF-二醇-7PO二丙烯酸酯和清除产物(即过量丙烯酸与Ipox CL 16反应的产物)的混合物—按如下表征:
粘度:460mPas
碘色数:0.4
实施例4
THF-二醇-5.3PO二丙烯酸酯的制备
在2000ml三颈烧瓶中将879.51g(4.0mol OH)THF-二醇-5.3PO、320.49g丙烯酸、228g环己烷和75.30g对甲苯磺酸(65%eq.)在由0.86g浓度为31.5重量%的CuCl2水溶液、0.24g甲基氢醌和3g H3PO2构成的稳定剂混合物存在下合并且将这些组分在99℃下酯化。在8小时内实现79%的转化率。将产物通过含水萃取过量丙烯酸、在减压下除去溶剂并随后在Seitz K300过滤器上过滤产物而后处理。产物表征如下:
粘度:70mPas
碘色数:5.2
应用实施例
在下列应用实施例中,使用IST UV系统(系统类型:M-40-2×1-R-TR-SLC-SO-inert;灯1:IST UV灯M400U2HC;灯2:IST UV灯M400U2H)固化涂料组合物:
应用实施例1
测定实施例1的产物的膜性能
将实施例1的产物与基于该产物为5重量%的光引发剂Irgacure 500混合。使用4方向棒施涂器将如此制备的涂料组合物施用于Stamylan,其中该棒涂布器的狭缝宽度为200μm(因此意味着所施涂涂层的湿膜厚度为200μm)。固化在氮气气氛下以1900mJ/cm2的能量输入进行。这之后测定摆杆阻尼(PD)、Erichsen杯突(Ew)和划格法附着力值。所得结果如下:
PD=113s
Ew=1.6mm
划格法附着力值=0
应用实施例2
测定实施例2的产物的膜性能
将实施例2的产物与基于该产物为5重量%的光引发剂Irgacure 500混合。使用4方向棒施涂器将如此制备的涂料组合物施用于Stamylan,其中该棒涂布器的狭缝宽度为200μm(因此意味着所施涂涂层的湿膜厚度为200μm)。固化在氮气气氛下以1900mJ/cm2的能量输入进行。这之后测定摆杆阻尼(PD)、Erichsen杯突(Ew)和划格法附着力值。所得结果如下:
PD=88s
Ew=4.1mm
划格法附着力值=1
应用实施例3
测定实施例3的产物的膜性能
将实施例3的产物与基于该产物为5重量%的光引发剂Irgacure 500混合。使用4方向棒施涂器将如此制备的涂料组合物施用于Stamylan,其中该棒涂布器的狭缝宽度为100μm(因此意味着所施涂涂层的湿膜厚度为100μm)。固化在氮气气氛下以1900mJ/cm2的能量输入进行。这之后测定摆杆阻尼(PD)、Erichsen杯突(Ew)和划格法附着力值。所得结果如下:
PD=123s
Ew=3.3mm
划格法附着力值=1
应用实施例4
测定实施例4的产物的膜性能
将实施例4的产物与基于该产物为5重量%的光引发剂Irgacure 500混合。使用4方向棒施涂器将如此制备的涂料组合物施用于Stamylan,其中该棒涂布器的狭缝宽度为100μm(因此意味着所施涂涂层的湿膜厚度为100μm)。固化在氮气气氛下以1900mJ/cm2的能量输入进行。作为光引发剂加入5%Irgacure 500;用4方向施涂器施用于Stamylan;棒涂布器狭缝宽度100μm(因此意味着所施加涂层的湿膜厚度为100μm);在氮气气氛下以1900mJ/cm2的能量输入固化。这之后测定摆杆阻尼(PD)、Erichsen杯突(Ew)和划格法附着力值。所得结果如下:
PD=141s
Ew=3.1mm
划格法附着力值=0
Claims (10)
4.根据权利要求3的用途,其中所述固体基材为塑料。
6.根据权利要求5的用途,其中所述固体基材为塑料。
8.根据权利要求7的方法,其中所述固体基材为塑料。
9.根据权利要求7的方法,其中所述辐射固化是使用波长为200-500nm的UV光的固化。
10.根据权利要求7的方法,其中所述固体基材为塑料且所述辐射固化是使用波长为250-400nm的UV光的固化。
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US3256254A (en) * | 1962-08-28 | 1966-06-14 | Du Pont | Oxycarbocyclic ester compositions containing aryl peroxides and tertiary aromatic amines, polymerizable in air |
US4341711A (en) * | 1980-06-12 | 1982-07-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Dimethacrylic acid esters of dimethyloltetrahydrofuran and its derivatives |
US6426034B1 (en) * | 2000-10-31 | 2002-07-30 | Lilly Industries, Inc. | Radiation curable coating for thermoplastic substrates |
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US4341711A (en) * | 1980-06-12 | 1982-07-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Dimethacrylic acid esters of dimethyloltetrahydrofuran and its derivatives |
US6426034B1 (en) * | 2000-10-31 | 2002-07-30 | Lilly Industries, Inc. | Radiation curable coating for thermoplastic substrates |
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Title |
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粘合剂的涂覆方式;华兴情报所电子情报室;《表面安装技术设计指南》;19911030;参见第79页第26行—第80页第11行 * |
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