CN101044179A - 基于硫醇－nco固化的涂料组合物 - Google Patents
基于硫醇－nco固化的涂料组合物 Download PDFInfo
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- CN101044179A CN101044179A CNA2005800355120A CN200580035512A CN101044179A CN 101044179 A CN101044179 A CN 101044179A CN A2005800355120 A CNA2005800355120 A CN A2005800355120A CN 200580035512 A CN200580035512 A CN 200580035512A CN 101044179 A CN101044179 A CN 101044179A
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
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- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
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- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
本发明涉及一种包含一种或多种聚硫醇和一种或多种多异氰酸酯和一种潜碱催化剂的涂料组合物，潜碱催化剂可通过湿气活化，其中当量比NCO∶SH为1∶2－2∶1。潜催化剂选自唑烷、醛亚胺、酮亚胺和烯胺。潜催化剂以相对于可固化材料重量至多20％的量存在。该组合物另外包含一种或多种以相对于可固化材料重量至多4％的量的光引发剂。
Description
本发明涉及一种包含一种或多种聚硫醇、一种或多种多异氰酸酯和一种去活化碱催化剂的涂料组合物。
基于聚硫醇和多异氰酸酯的涂料组合物用碱催化剂催化。为防止过早交联，碱催化剂可以为阻塞的或去活化的。WO 01/92362公开了基于硫醇-异氰酸酯使用光潜碱(photolatent base)交联的组合物。为固化这种涂料，新施涂的层需要用合适波长的光化辐射进行照射。因此，这种涂料在大面积涂刷例如车库地面等等时很少使用。此外，表面的某些点可能较难进行照射。在这些隐蔽点上的固化速度低。
本发明的目的是提供一种贮存期长但在整个基底包括隐蔽点上具有快的固化速度的涂料组合物。
本发明的目的用一种包含一种或多种聚硫醇、一种或多种多异氰酸酯和一种去活化碱催化剂的涂料组合物实现，去活化碱催化剂可通过湿气活化。当量比NCO∶SH，即NCO基团的数量相对于SH基团的数量为1∶2-2∶1。
可湿气活化的碱化合物例如唑烷通常与异氰酸酯基团具有反应性。因此，该化合物用作多异氰酸酯交联剂。令人惊讶地发现在硫醇-异氰酸酯交联体系中，这些化合物基本上并不通过异氰酸酯基团连接而是在湿气影响下作为用于硫醇-异氰酸酯交联的催化剂起作用。
唑烷为与湿气反应形成碱的适合化合物，碱能催化SH-NCO反应。适合的唑烷例如碳酸-二-N-乙基-2-异丙基-1，3-唑烷，作为IncozolLV市售；2-(3-庚基)-N-丁基-1，3-oxazolane，作为Incozol2市售，以及氨基甲酸酯双-唑烷，例如作为Hardener OZ市售。另外适合的潜碱化合物为例如烯胺、酮亚胺和醛亚胺。
潜催化剂可以以例如相对于可固化材料的重量至多20％的量存在，例如0.01-6％，如3.5-5％。
在另外的实施方案中，涂料组合物可另外包含一种或多种光引发剂，在光的影响下形成自由基。令人惊讶地发现甚至以厚层施涂的颜料体系中干燥大大加快，约2-20倍。该效果尤其当使用唑烷作催化剂时发生。光引发剂可以例如以相对于可固化材料的重量0.01-2.0％的量存在，例如0.1-1.0％的量。
适合的光引发剂例如为乙基4-(二甲氨基)苯甲酸酯(SpeedcureEPD)、2-(二甲氨基)乙基苯甲酸酯(SpeedcureDMB)、4-苯甲酰-4’-甲基二苯硫(SpeedcureBMS)、2-乙基己基-4-二甲氨基苯甲酸酯(SpeedcureEHA)；1，3，5-三甲基苯甲酰二苯基氧化膦(SpeedcureTPO)，所有可从Lambson得到。在可见日光下使用的光引发剂为例如双(4-环戊二烯-1-基)-双[2，6-二氟-3-(1-氢-吡咯-1-基)-苯基]钛(Irgacure784，Ciba Specialty)。其它适合的光引发剂包括酮如甲基乙基酮、2，3-丁二酮、1-羟基环己基苯基酮、2-羟基-2-甲基-1-苯基丙-1-酮，和芳族酮如苯乙酮、二苯甲酮、4-氨基二苯甲酮、4，4’-二氨基二苯甲酮、4，4’-双(二甲氨基)二苯甲酮、苯戊酮、苯己酮、邻-甲氧基二苯甲酮、α-苯基苯丁酮、γ-苯基苯丁酮、对-吗啉基苯丙酮、二苯并环庚酮、4-吗啉基二苯甲酮、4-甲氧基苯乙酮、对-二乙酰苯、1，3，5-三乙酰苯；苯偶姻化合物，例如苯偶姻、苯偶姻甲基醚和苯偶姻乙基醚、4-吗啉基脱氧苯偶姻；醌和蒽酮化合物，例如对苯二酚、蒽醌、萘醌、二氢苊醌和3-甲基-1，3-重氮-1，9-苯并蒽酮；酚化合物，例如2，4-二硝基酚；膦化合物如三苯基-膦和三-邻-甲苯基膦；偶氮化合物，例如偶氮二异丁腈；噻吨酮化合物包括例如2，4-二乙氧基噻吨酮、异丙基噻吨酮(SpeedcureITX)、1-氯-4-丙氧基噻吨酮(SpeedcureCPTX)和2-氯噻吨酮；以及各种其他化合物，例如苯偶酰、苯甲醛、1-萘甲醛、α-四氢萘酮、2-乙酰菲、3-乙酰菲、9-乙酰-菲、10-硫杂蒽酮、3-乙酰基吲哚、9-芴酮、1-二氢茚酮、9-呫吨酮、9-硫杂蒽酮、7-H-苯[脱]蒽-7-酮、1-萘乙酮和2-萘乙酮。做为选择，光引发剂可以为氧化膦化合物，例如2，4，6-三甲基苯甲酰基二苯基氧化膦(LucirinTPO，来自BASF)或酰基氧化膦化合物，例如单、二或三酰基氧化膦或其混合物。二酰基氧化膦光引发剂的实例为二(2，4，6-三甲基苯甲酰基)-苯基-氧化膦(Irgacure819，来自于Ciba Specialty Chemicals)或二(2，6-二甲氧基-苯甲酰基)-2，4，4-三甲基戊基氧化膦(DMBAPO，Irgacure403，来自于Ciba Specialty Chemicals)。可以使用不同光引发剂的混合物。
作为选择或者另外地可使用一种或多种光潜碱，例如在WO 94/28075和EP-A 0 882 072中公开的光潜碱。适合的光潜碱包括任选用烷基醚或烷基酯基团取代的N-取代的4-(o-硝基苯基)二氢吡啶以及四元有机硼光引发剂。N-取代的4-(o-硝基苯基)二氢吡啶的实例为N-甲基硝苯吡啶(Macromolecules 1998，31，4798)、N-丁基硝苯吡啶、N-丁基2，6-二甲基4-(2-硝基苯基)1，4-二氢吡啶3，5-二羧酸二乙基酯，和根据下式的硝苯吡啶：
即N-甲基-2，6-二甲基4-(4，5-二甲氧基-2-硝基苯基)1，4-二氢吡啶3，5-二羧酸二乙基酯。GB-A-2 307 473中公开了四元有机硼光引发剂的实例，例如
另外适合的可选物为属于α-氨基苯乙酮的光潜碱。可使用的α-氨基苯乙酮实例为4-(甲基硫代苯甲酰基)-1-甲基-1-吗啉乙烷(Ciba SpecialtyChemicals的Irgacure907)、(4-吗啉苯甲酰基)-1-苄基-1-二甲基氨基丙烷(Ciba Specialty Chemicals的Irgacure369)或根据下式的α-氨基苯乙酮：
此外，发现对于这些光加速的湿气固化体系，贮存期可以通过加入无机酸(如硝酸)延长，甚至使用少量，例如0.005-0.05重量％。加入的少量酸几乎不影响固化时间。
适合的聚硫醇可通过含羟基化合物与含硫醇基的酸如3-巯基丙酸、2-巯基丙酸、硫代-水杨酸、巯基琥珀酸、巯基乙酸或巯基丙氨酸反应而制备。适合的含羟基化合物的实例为二醇、三醇和四醇，如1，4-丁二醇、1，6-己二醇、2，2-二甲基-1，3-丙二醇、2-乙基-2-丙基-1，3-丙二醇、1，2-、1，3-和1，4-环己二醇和相应的环己烷二甲醇、1，1，1-三羟甲基丙烷、1，2，3-三羟甲基丙烷和季戊四醇。根据方法制备的化合物实例包括季戊四醇四(3-巯基丙酸酯)、季戊四醇四(2-巯基乙酸酯)、三羟甲基丙烷三(3-巯基丙酸酯)、三羟甲基丙烷三(2-巯基丙酸酯)和三羟甲基丙烷三(2-巯基乙酸酯)。用三羟甲基丙烷三(3-巯基丙酸酯)和季戊四醇四(3-巯基丙酸酯)已取得好的结果。根据方法制备的化合物的另外实例由基于起始多元醇如三羟甲基丙烷的超支化多元醇核和二羟甲基丙酸组成。多元醇随后用3-巯基丙酸和异壬酸酯化。这些方法在EP-A 0 448 224和WO93/17060中有描述。
制备包含聚硫醇的化合物的其他合成法包括：
-芳基或烷基卤化物与NaHS反应以将侧硫醇基分别引入到烷基和芳基化合物中；
-Grignard试剂与硫反应以将侧硫醇基引入结构中；
-根据Michael加成反应、亲核反应、亲电子反应或自由基反应聚硫醇与聚烯烃反应；
-硫醇官能醇与异氰酸酯官能化合物反应，以及
-二硫化物还原。
聚硫醇可例如具有一个或多个羟基并且具有下式的结构：T[(C3H6O)nCH2CHOHCH2SH]3，其中T为三元醇如三羟甲基丙醇或甘油。该化合物的实例为由Henkel市购的商标HenkelCapcure3/800。
作为选择，聚硫醇可例如为具有聚酯树脂、聚氨酯树脂、聚丙烯酸酯树脂或聚醚树脂为主链的树脂。这些异氰酸酯反应性化合物也可包含羟基基团。
聚硫醇可例如为由(a)至少一种聚羧酸或其反应衍生物，(b)至少一种多元醇，和(c)至少一种硫醇官能的羧酸制备的聚酯。聚酯优选具有支化结构。支化聚酯通常通过用多元醇缩合聚羧酸或其反应性衍生物如相应的酸酐或较低基烷基酯得到，反应物至少之一具有至少为3的官能度。适合的聚羧酸或其反应性衍生物的实例为四氢邻苯二甲酸、四氢邻苯二甲酸酐、六氢邻苯二甲酸、六氢邻苯二甲酸酐、甲基六氢邻苯二甲酸、甲基六氢邻苯二甲酸酐、二甲基环己烷二羧酸酯、1，4-环己烷二羧酸、1，3-环己烷二羧酸、邻苯二甲酸、邻苯二甲酸酐、间苯二甲酸、对苯二甲酸、5-叔丁基间苯二甲酸、偏苯三酸酐、马来酸、马来酸酐、富马酸、琥珀酸、琥珀酸酐、十二烯基琥珀酸酐、二甲基琥珀酸酯、戊二酸、己二酸、己二酸二甲酯、壬二酸，以及其混合物。适合的多元醇的实例包括三羟甲基丙烷、三羟甲基乙烷、甘油、1，2，6-己三醇、乙二醇、1，2-丙二醇、1，3-丙二醇、2-甲基丙-1，3-二醇、新戊二醇、2-丁基-2-乙基-1，3-丙二醇、环己烷-1，4-二羟甲基、新戊二醇和羟基新戊酸的单酯、氢化的双酚A、1，5-戊二醇、3-甲基-戊二醇、1，6-己二醇、2，2，4-三甲基戊-1，3-二醇、二羟甲基丙酸、季戊四醇、二-三羟甲基丙烷、二季戊四醇，以及其混合物。适合的硫醇官能的有机酸的实例包括3-巯基丙酸、2-巯基丙酸、硫代-水杨酸、巯基琥珀酸、巯基乙酸、巯基丙氨酸以及其混合物。任选地，一元羧酸和一元醇可用于制备聚酯。优选使用C4-C18一元羧酸和C6-C18一元醇。C4-C18一元羧酸的实例包括新戊酸、己酸、庚酸、辛酸、壬酸、2-乙基己酸、异壬酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、异硬脂酸、硬脂酸、羟基硬脂酸、苯甲酸、4-叔丁基苯甲酸以及其混合物。C6-C18一元醇的实例包括环己醇、2-乙基己醇、硬脂醇和4-叔丁基环己醇。
作为选择，聚硫醇可以为硫醇官能的聚丙烯酸酯。聚丙烯酸酯可衍生于(甲基)丙烯酸单体如(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯，乙烯基衍生物如苯乙烯，以及任选羟基官能的丙烯酸单体如羟基乙基(甲)丙烯酸酯、羟基丙基(甲基)丙烯酸酯、羟基丁基(甲基)丙烯酸酯等等，或其混合物，术语(甲基)丙烯酸酯和(甲基)丙烯酸分别指甲基丙烯酸酯和丙烯酸酯以及甲基丙烯酸和丙烯酸。硫醇基通过二甲基-间-异丙烯基苯甲基异氰酸酯与巯基乙醇的反应产物而引入。作为选择，将甲基丙烯酸缩水甘油酯引入到聚合物中以制备环氧官能的聚丙烯酸酯。环氧基团然后与适合的如上所述的硫醇官能的有机酸反应。聚丙烯酸酯通过常规方法制备，例如通过将适合的单体缓慢加到适合的聚合引发剂如偶氮或过氧引发剂中。
在本发明的涂料组合物中还包括二-、三-或更高硫醇官能的稀释剂如乙烷二硫醇或二-β-巯基-乙基硫化物。优选使用较高分子量硫醇官能的化合物，化合物可通过聚硫醇官能化合物与多异氰酸酯反应得到。
适合的有机多异氰酸酯包括多官能，优选具有2.5-5的平均NCO官能度的游离多异氰酸酯，并且可以为(环)脂族、芳脂族或基本的芳族。有机多异氰酸酯可以为封端的。多异氰酸酯可包括缩二脲、氨基甲酸乙酯、缩脲二酮和异氰脲酸酯衍生物。这些有机多异氰酸酯的实例包括1，6-二异氰酸己烷、异佛尔酮二异氰酸酯、2，4-甲苯二异氰酸酯、2，6-甲苯二异氰酸酯、二苯甲烷-二异氰酸酯、4，4-二(二异氰酸-环己基)甲烷、1，4-二异氰酸丁烷、1，5-二异氰酸-2，2-二甲基戊烷、2，2，4-三甲基-1，6-二异氰酸己烷、1，10-二异氰酸癸烷、4，4-二异氰酸-环己烷、2，4-六氢甲苯二异氰酸酯、2，6-六氢甲苯二异氰酸酯、降莰烷二异氰酸酯、1，3-亚二甲苯基二异氰酸酯、1，4-亚二甲苯基二异氰酸酯、1-异氰酸基-3-(异氰酸甲基)-1-甲基环己烷、间-α，α-α’，α’-四甲基亚二甲苯基二异氰酸酯、上述其衍生物以及其混合物。通常，这些产物在环境温度下为液体并且为广泛市售的。尤其适合的异氰酸酯固化剂为三异氰酸酯和加合物。其实例为1，8-二异氰酸-4-(二异氰酸甲基)辛烷、3摩尔甲苯二异氰酸酯与1摩尔三羟甲基丙烷的加合物、1，6-二异氰酸己烷的异氰脲酸酯三聚物、异佛尔酮二异氰酸酯的异氰脲酸酯三聚物、1，6-二异氰酸己烷的缩脲二酮二聚物、1，6-二异氰酸己烷的缩二脲三聚物、3摩尔间-α，α-α’，α’-四甲基二甲苯二异氰酸酯与1摩尔三羟甲基丙烷的加合物以及其混合物。优选环三聚物(异氰脲酸酯)和1，6-己烷二异氰酸酯和异佛尔酮二异氰酸酯的缩脲二酮。通常这些化合物含有少量其更高同系物。
任选地，包含至少两个羟基官能团的羟基官能化合物可存在于可固化材料中。包含至少两个羟基官能团的羟基官能化合物可选自聚酯多元醇、聚醚多元醇、聚丙烯酸酯多元醇、聚氨酯多元醇、乙酰丁酸纤维素、羟基官能的环氧树脂、醇酸树脂和树枝状多元醇如在WO 93/17060中有描述。还可包括羟基官能的低聚物和单体例如蓖麻油和三羟甲基丙烷。适合的多元醇为丙烯酸酯多元醇，例如来自Nuplex的Setalux1157。
多异氰酸酯可通过任何适当技术与聚硫醇混合。然而，简单的搅拌通常就足够了。有时可以用有机溶剂如乙酸乙酯或1-甲氧基-2-丙基乙酸酯稍微稀释多异氰酸酯以降低其粘度。
涂料组合物在环境温度下的贮存期通常大于四分之一小时，例如多于半小时，高达大约5小时或者甚至更长，取决于使用的催化剂和它们的量以及是否使用封端酸。
根据本发明的组合物可以为含溶剂组合物或无溶剂组合物。由于组合物可以由液体低聚物组成，尤其适合用作高固体组合物或无溶剂组合物。涂料组合物也可以粉末涂料组合物和热溶性涂料组合物使用。优选组合物中的理论挥发性有机物含量(VOC)为少于约450g/l，更优选少于约350g/l，最优选少于约250g/l，或甚至少于100g/l。
涂料组合物可进一步包含其他成分、添加剂或助剂，例如颜料、染料、乳化剂(表面活性剂)、颜料分散助剂、光敏剂、均化剂、防堵孔剂、防沫剂、防流挂剂、热稳定剂、紫外线吸收剂、抗氧化剂和填料。
本发明的涂料组合物可施涂于任何基底。基底可以为例如金属、塑胶、木头、玻璃、陶瓷或某些其他涂层。其他涂层可由本发明的涂料组合物组成或者可以为不同的涂料组合物。本发明的涂料组合物显示出作为地面涂料例如在混凝土地面上，或作为涂料或修补涂料例如作为底漆，或作为车辆如汽车、火车、飞机等的透明涂层的特别实用性。
涂料组合物可通过常规方法例如通过喷枪、刷子或辊施涂，优选喷涂。固化温度通常为0-100℃，例如0-30℃。
本发明另外通过以下实施例说明。在这些实施例中，下面列出的组合物为可用的。
Actilane411 丙烯酸酯，由Akzo Nobel Chemicals市购；
AerosilR972 疏水改性的硅石，由Degussa市购；
AncamineK54 三-(二甲基氨基甲基)苯酚，由Air Products市购；
ASP 600 水合硅酸铝，由Engelhard市购；
AutobasePlus 汽车修补底涂层，由Akzo Nobel Car Refinishes
市购；
Byk306 表面活性剂，由Byk市购；
Colour Black FW2 碳黑，由Degussa市购；
DesmodurDN 多异氰酸酯，由Bayer市购；
DesmodurE14 多异氰酸酯，由Bayer；
Disperbyk110 分散剂，由Byk市购
Hardener OZ 氨基甲酸乙酯二-唑烷，由Bayer市购；
IncozolLV 碳酸-二-N-乙基-2-异丙基-1，3-唑烷，由
Industrial Copolymers Limited市购；
Incozol2 2-(3-庚基)-N-丁基-1，3-oxazolane，由Industrial
Copolymers Limited市购；
Irgacure784 光引发剂，由Ciba Specialty Chemicals市购；
SpeedcureBMS 光引发剂，由Lambson市购；
TipureR902 二氧化钛，由DuPont市购；
TolonateHDT LV 多异氰酸酯，由Rhodia市购；
VestaminA139 醛亚胺，由Degussa-Hüls市购；
ZeeospheresW-210 陶瓷微球，由3M市购。
在实施例中，所有含量以克给出，另外指出的除外。
使用以下测定方法：
贮存期 - 在组分混合之后体系可刷涂的时间；
干燥时间 - 将涂料组合物用拉杆施涂在玻璃板上。层厚为125μm，
温度为20℃。干燥通过BK干燥记录器测试。结果可分
类如下：
阶段1：针的痕量线再次闭合(“开放时间”)；
阶段2：针在不再闭合的油漆中描出直线(“不粘时间”)；
阶段3：针描出凌乱的线(“无尘”)；
阶段4：针未留下划痕(“无划痕时间”)。
粘度 - 使用流变仪(Rheolab MC1，转子：Z2 DIN)测定；静止
15分钟后，以每分钟150转的速度测量粘度1分钟。程
序重复几次。
实施例1
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(TolonateHDT LV)和6％唑烷(Hardener OZ)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为60分钟(在85％的RH下)，此时罐中的粘度为：0.13Pa.s。贮存期为3小时。
实施例2
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(TolonateHDT LV)和6％唑烷(Incozol2)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为20分钟(在85％的RH下)，此时罐中的粘度为：0.25Pa.s。
实施例3
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(TolonateHDT LV)和6％唑烷(IncozolLV)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为80分钟(在85％的RH下)，此时罐中的粘度为：0.10Pa.s。
实施例4
向实施例1的配制剂中加入1％SpeedcureBMS。将试样施涂在板上并且将板用UV-A灯在20cm(UVAHAND-250，35mW/cm2)照射。阶段4的固化时间减少至10分钟。贮存期不因SpeedcureBMS的加入受到影响并且保持在3小时。
实施例5
向实施例1的配制剂中加入1％SpeedcureBMS、10％TiO2(TipureR902-38)和1％有机黑(Colour Black FW2)。将试样施涂在板上并且将板用UV-A灯在20cm照射。阶段4的固化时间减少至20分钟。
实施例6
向实施例1的配制剂中加入1％Irgacure784。将试样施涂在板上并且将板用1000W建筑灯在50cm照射。阶段4的固化时间减少至3分钟。贮存期不因Irgacure784的加入受到影响。
实施例7
向实施例4的配制剂中加入0.03％HNO3。将试样施涂在板上并且将板用UV-A灯在20cm照射。阶段4的固化时间保持在10分钟。贮存期加倍。
实施例8
制备无溶剂双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和1％SpeedcureBMS。第二种组分包含多异氰酸酯(TolonateHDTLV)和2％唑烷(IncozolLV)。将试样施涂在板上并且将板用UV-A灯在20cm照射。阶段4的固化时间为20分钟(在60％RH下)。贮存期为45分钟。
实施例9
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(DesmodurE14，Bayer)和6％唑烷(Hardener OZ)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为1.5小时(在60％RH下)，贮存期为2小时。
实施例10
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(DesmodurDN)和6％唑烷(Hardener OZ)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为1.5小时(在60％RH下)，贮存期为2小时。
实施例11
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯和40％乙酸丁酯。第二种组分包含多异氰酸酯(TolonateHDT LV)和6％酮亚胺(VestaminA139)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为2小时(在60％RH下)，贮存期为2小时。
对比例1
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯、15％乙酸丁酯和0.25％三苯膦。第二种组分包含多异氰酸酯(TolonateHDT LV)和2％丙烯酸酯(Actilane411)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为1.5小时(在20℃和85％RV下)，贮存期为30分钟。
对比例2
制备双组分涂料组合物。第一种组分包含季戊四醇3-巯基丙酸酯、15％乙酸丁酯和0.05％Ancaminek54(Air Products)。第二种组分包含多异氰酸酯(TolonateHDT LV，Rhodia)。
将组分在施涂之前按化学计量混合。阶段4的固化时间为3.0小时(在20℃和85％RV下)，贮存期为20分钟。
实施例12
制备三组分地面涂料，包括硫醇组分A、异氰酸酯组分B和催化剂组分C。组分A包含83重量％季戊四醇四(3-巯基丙酸酯)、16.5重量％TiO2(TipureR 902)和约0.5重量％的聚硅氧烷消泡剂(BykA-525)。组分A中还以任何所需量加入颜料膏。如果使用黑色颜料膏，该膏应含每1重量份(pbw)碳黑(Farbruss FW2)20重量份季戊四醇四(3-巯基丙酸酯)、0.2重量份BykA-525消泡剂和0.04重量份甲基-二-乙醇胺以中和酸性。组分B包含100％1，6-己二异氰酸酯的异氰脲酸酯(TolonateHDT-LV2)。组分C包含120重量份沙、15重量份石英砂和1-4重量％Incozol2。
将组分A和组分B以A∶B＝48∶52的比率混合并施涂在混凝土基底上。随后，将沙组分C撒在新施涂的层上以催化NCO-SH交联。在将沙撒在第一层上之后施涂组分A+B的第二层。
实施例13
制备双组分透明涂层。第一种组分包含季戊四醇3-巯基丙酸酯、0.8重量％(基于固体基料总重量)SpeedcureBMS、14.6重量％(基于固体基料总重量)的乙酸丁酯和降低表面张力的添加剂(Byk306)。
第二种组分包含多异氰酸酯(TolonateHDT LV)、7.7％(基于固体基料总重量)二甲苯和5.2％(基于固体基料总重量)唑烷(Hardener OZ，Bayer)。
将组分在施涂之前按化学计量混合。贮存期为20分钟。使用试样用蓝色(Halcyon Blue M.2c)溶剂基底涂层(AutobasePlus of Akzo Nobel CarRefinishes)在板上施涂透明涂层(约60μm)。晾3分钟后，将这些板用来自4个TL-10R管的UV-A光(菲利普电光：11-13mW/cm2)照射。透明涂层的完全固化时间为14分钟(在45％RH下)。无UV的这些板(隐蔽-固化)的完全固化时间大约为90分钟(在45％RH下)。
实施例14
重复实施例3，而将4％(重量)唑烷加到含溶剂的底涂层中，。底涂层干燥后，使用实施例1的两组分组合物在底涂层上施涂60μm的透明涂层。晾后将板用UV-A光照射。完全固化时间从14分钟加速到9分钟。
实施例15
制备颜料体积浓度PVC为30的双组分UV底漆。第一种组分包含季戊四醇3-巯基丙酸酯、乙酸异丁酯、0.3重量％(基于固体基料总重量)的Disperbyk110、52.8重量％(基于固体基料总重量)的ZeeospheresW-210(来自3M)、AerosilR 972(来自Degussa)和35.9重量％(基于固体基料总重量)的ASP 600(来自Engelhard corp.)。将这些固体原料在溶解器辅助下碾磨在季戊四醇3-巯基丙酸酯和乙酸异丁酯中至20μm。最后，加入0.7重量％(基于固体基料总重量)的Byk306。
第二种组分包含多异氰酸酯(TolonateHDT LV)、二甲苯、5.6重量％(基于固体基料总重量)的唑烷(Hardener OZ，Bayer)和0.7重量％(基于固体基料总重量)的SpeedcureBMS。
将组分在施涂之前混合(当量比SH∶NCO＝100∶125)。贮存期大约为20分钟。涂料组合物用拉杆施涂在镀锡铁皮上。(干燥)层厚度为110-120μm。晾3分钟后，将这些板用UV-A光照射。底漆的完全固化时间为15分钟(在45％RH下)。涂料在60分钟内为好的沙状。这些板无UV(隐蔽-固化)的完全固化时间大约为60分钟(在45％RH下)。3小时后砂磨为合理的。
Claims (10)
1.一种包含一种或多种聚硫醇和一种或多种多异氰酸酯和一种潜碱催化剂的涂料组合物，该潜碱催化剂可通过湿气活化，其中当量比NCO∶SH为1∶2-2∶1。
2.根据权利要求1的涂料组合物，其特征在于所述潜催化剂选自唑烷、醛亚胺、酮亚胺和烯胺。
3.根据权利要求1或2的涂料组合物，其特征在于所述去活化催化剂以相对于可固化材料的重量至多20％的量存在，例如0.01-10重量％或0.9-6重量％。
4.根据前述权利要求中任一项的涂料组合物，其特征在于所述组合物另外包含一种或多种光引发剂。
5.根据权利要求4的涂料组合物，其特征在于所述光引发剂以相对于可固化材料的重量至多4％的量存在，优选0.001-1.2重量％。
6.根据前述权利要求中任一项的涂料组合物，其特征在于所述组合物包含唑烷和光引发剂的组合。
7.根据前述权利要求中任一项的涂料组合物，其特征在于所述组合物包含无机酸，例如硝酸。
8.唑烷和光引发剂的组合在碱催化的涂料组合物中作为催化剂的用途。
9.根据权利要求1-7中任一项的涂料组合物作为汽车修补底漆或作为汽车修补透明涂层的用途。
10.根据权利要求1-7中任一项的涂料组合物作为混凝土地面涂料的用途。
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| AU2001240666B2 (en) * | 2000-03-13 | 2005-06-30 | Akzo Nobel N.V. | Compositions comprising an isocyanate-functional compound, and isocyanate-reactive compound, and a co-catalyst |
| EP1285012B1 (en) * | 2000-05-26 | 2007-01-10 | Akzo Nobel Coatings International B.V. | Photoactivatable coating composition |
| AU2003251678A1 (en) * | 2002-08-13 | 2004-03-11 | Akzo Nobel Coatings International B.V. | Multilayer coating system comprising thiol-funcitonal compounds |
-
2005
- 2005-09-16 PT PT05794612T patent/PT1789464E/pt unknown
- 2005-09-16 UA UAA200704229A patent/UA87704C2/uk unknown
- 2005-09-16 DK DK05794612T patent/DK1789464T3/da active
- 2005-09-16 AT AT05794612T patent/ATE413421T1/de active
- 2005-09-16 WO PCT/EP2005/054628 patent/WO2006030029A1/en active Application Filing
- 2005-09-16 PL PL05794612T patent/PL1789464T3/pl unknown
- 2005-09-16 MX MX2007003197A patent/MX2007003197A/es active IP Right Grant
- 2005-09-16 CA CA2580334A patent/CA2580334C/en not_active Expired - Fee Related
- 2005-09-16 US US11/663,372 patent/US7709555B2/en not_active Expired - Fee Related
- 2005-09-16 EA EA200700657A patent/EA012572B1/ru not_active IP Right Cessation
- 2005-09-16 JP JP2007531756A patent/JP5189363B2/ja not_active Expired - Fee Related
- 2005-09-16 NZ NZ553842A patent/NZ553842A/en not_active IP Right Cessation
- 2005-09-16 CN CN2005800355120A patent/CN101044179B/zh not_active Expired - Fee Related
- 2005-09-16 EP EP05794612A patent/EP1789464B1/en active Active
- 2005-09-16 KR KR1020077008305A patent/KR101167892B1/ko not_active IP Right Cessation
- 2005-09-16 AU AU2005284095A patent/AU2005284095B2/en not_active Ceased
- 2005-09-16 BR BRPI0515462-6A patent/BRPI0515462A/pt not_active IP Right Cessation
- 2005-09-16 DE DE602005010881T patent/DE602005010881D1/de active Active
- 2005-09-16 ES ES05794612T patent/ES2314717T3/es active Active
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2007
- 2007-03-15 IL IL181979A patent/IL181979A/en not_active IP Right Cessation
- 2007-03-27 NO NO20071615A patent/NO20071615L/no not_active Application Discontinuation
- 2007-03-29 MA MA29786A patent/MA28881B1/fr unknown
- 2007-04-16 ZA ZA200703101A patent/ZA200703101B/xx unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101874050A (zh) * | 2007-10-17 | 2010-10-27 | 巴斯夫欧洲公司 | 基于有机金属化合物的光潜催化剂 |
| CN101874050B (zh) * | 2007-10-17 | 2013-10-23 | 巴斯夫欧洲公司 | 基于有机金属化合物的光潜催化剂 |
| CN102224180A (zh) * | 2008-12-02 | 2011-10-19 | Sika技术股份公司 | 含有羟基醛亚胺的聚氨酯组合物 |
| CN102224180B (zh) * | 2008-12-02 | 2014-04-30 | Sika技术股份公司 | 含有羟基醛亚胺的聚氨酯组合物 |
| CN104837815A (zh) * | 2012-12-11 | 2015-08-12 | 阿克佐诺贝尔国际涂料股份有限公司 | 硫醇官能化合物 |
| CN104837815B (zh) * | 2012-12-11 | 2017-07-21 | 阿克佐诺贝尔国际涂料股份有限公司 | 硫醇官能化合物 |
| CN108368190A (zh) * | 2015-12-17 | 2018-08-03 | 三井化学株式会社 | 光固化性树脂组合物、显示元件密封剂、液晶密封剂和液晶显示面板及其制造方法 |
| CN108368190B (zh) * | 2015-12-17 | 2019-12-31 | 三井化学株式会社 | 光固化性树脂组合物、显示元件密封剂、液晶密封剂和液晶显示面板及其制造方法 |
| CN108892763A (zh) * | 2018-05-28 | 2018-11-27 | 岭南师范学院 | 一种聚氨酯二元硫醇预聚物、光敏树脂组合物及其制备方法和应用 |
| CN109705297A (zh) * | 2018-12-05 | 2019-05-03 | 万华化学集团股份有限公司 | 一种温湿响应快发泡型聚氨酯填充泡沫组合物及制备方法和用途 |
| CN109705297B (zh) * | 2018-12-05 | 2021-04-20 | 万华化学集团股份有限公司 | 一种温湿响应快发泡型聚氨酯填充泡沫组合物及制备方法和用途 |
| CN112521573A (zh) * | 2020-11-25 | 2021-03-19 | 山东益丰生化环保股份有限公司 | 一种改性聚硫醇及应用该改性聚硫醇的金属防腐uv涂料 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL181979A0 (en) | 2007-07-04 |
| EP1789464B1 (en) | 2008-11-05 |
| UA87704C2 (uk) | 2009-08-10 |
| DE602005010881D1 (de) | 2008-12-18 |
| ES2314717T3 (es) | 2009-03-16 |
| NO20071615L (no) | 2007-04-16 |
| MX2007003197A (es) | 2007-05-24 |
| JP5189363B2 (ja) | 2013-04-24 |
| EP1789464A1 (en) | 2007-05-30 |
| ATE413421T1 (de) | 2008-11-15 |
| CA2580334A1 (en) | 2006-03-23 |
| KR101167892B1 (ko) | 2012-07-30 |
| AU2005284095B2 (en) | 2011-04-07 |
| US20080194720A1 (en) | 2008-08-14 |
| BRPI0515462A (pt) | 2008-07-22 |
| DK1789464T3 (da) | 2009-03-09 |
| ZA200703101B (en) | 2008-08-27 |
| JP2008513560A (ja) | 2008-05-01 |
| PL1789464T3 (pl) | 2009-04-30 |
| NZ553842A (en) | 2009-09-25 |
| CN101044179B (zh) | 2011-07-06 |
| EA200700657A1 (ru) | 2007-08-31 |
| US7709555B2 (en) | 2010-05-04 |
| KR20070058606A (ko) | 2007-06-08 |
| CA2580334C (en) | 2013-07-02 |
| MA28881B1 (fr) | 2007-09-03 |
| PT1789464E (pt) | 2009-01-23 |
| EA012572B1 (ru) | 2009-10-30 |
| AU2005284095A1 (en) | 2006-03-23 |
| WO2006030029A1 (en) | 2006-03-23 |
| IL181979A (en) | 2013-01-31 |
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