CN109153874A - 含有山梨酸酯和光催化剂的涂料组合物 - Google Patents
含有山梨酸酯和光催化剂的涂料组合物 Download PDFInfo
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- 229940075554 sorbate Drugs 0.000 title claims abstract description 34
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 title claims abstract description 33
- 239000003054 catalyst Substances 0.000 title claims abstract description 27
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- 239000002243 precursor Substances 0.000 claims abstract description 26
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- 239000011324 bead Substances 0.000 claims abstract description 7
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- 230000033116 oxidation-reduction process Effects 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 230000005283 ground state Effects 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 230000005284 excitation Effects 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
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- 150000003254 radicals Chemical class 0.000 claims description 8
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- -1 iodonium hexafluorophosphate Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 4
- 229940075582 sorbic acid Drugs 0.000 claims description 4
- 235000010199 sorbic acid Nutrition 0.000 claims description 4
- 239000004334 sorbic acid Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 2
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- 229920006226 ethylene-acrylic acid Polymers 0.000 claims description 2
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- QXBUYALKJGBACG-UHFFFAOYSA-N 10-methylphenothiazine Chemical compound C1=CC=C2N(C)C3=CC=CC=C3SC2=C1 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
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- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WZHKCFDUDKJGBA-UHFFFAOYSA-N N1CCNCC1.S1C=CC=C1 Chemical compound N1CCNCC1.S1C=CC=C1 WZHKCFDUDKJGBA-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
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- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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Abstract
提供一种组合物，其包含a)稳定的聚合物颗粒水分散体，b)山梨酸酯，c)光催化剂和d)自由基前体。该组合物提供了一种快速增加涂层的柯尼希硬度并减少黄化的方法。
Description
本发明涉及包含山梨酸酯和光催化剂的组合物。该组合物提供了一种加速涂料组合物中山梨酸酯固化同时减少黄化的方法。
全球最近的环境法规正在推动建筑涂料市场对低气味或无气味以及低挥发性有机化学物质(VOC)的材料的需求。平衡VOC与所需的涂料性能属性是一项持续性挑战。
涂料制剂包含低Tg聚合物乳胶，其形成具有很少或不具有聚结剂的膜，或包含借助聚结剂形成膜的高Tg乳胶。含有低Tg聚合物的制剂通常会产生具有柔软和粘性感以及差耐久性的涂层。另一方面，使用高Tg聚合物的制剂需要永久性(非挥发性)聚结剂或挥发性聚结剂；已知永久性聚结剂会不利地影响后续涂料的硬度性能；另一方面，Texanol等挥发性聚结剂可能具有可接受的硬度性能——例如，对于典型的半光涂料，28天的柯尼希硬度为 ——但不利于其挥发性。
低温成膜和膜硬度都可以通过使用反应性聚结剂来实现。例如，WO2007/094922描述了使用双烯丙基不饱和脂肪酸酯作为反应性聚结剂。不幸的是，所述聚结剂不能为随后的涂料产生所需的硬度性能。
一类特别有吸引力的聚结剂是山梨酸的酯(山梨酸酯)，尤其是二山梨酸酯，其具有特别低的VOC。对山梨酸酯的持续关注是获得涂膜的最大膜硬度所需的相对长时间(约28天)。
因此，一个优点是在低VOC聚结剂领域中发现一种方法来加速含有山梨酸酯聚结剂的涂料的固化速率，而不会显着不利地影响涂料中的其它性能。
发明内容
本发明通过提供一种组合物满足了本领域的需要，该组合物包含a)稳定的聚合物颗粒水分散体，b)山梨酸酯，c)光催化剂，其能够通过氧化还原过程产生自由基并具有激发态氧化还原电位在小于-0.2V至不小于-2.5V的范围内，和d)自由基前体，其具有0.5V至-2V范围内的基态氧化还原电位，其中条件是自由基前体的基态电位大于光催化剂的激发态氧化还原电位。该组合物提供了一种快速增加涂层的柯尼希硬度并减少黄化的方法。
具体实施方式
本发明通过提供一种组合物满足了本领域的需要，该组合物包含a)稳定的聚合物颗粒水分散体，b)山梨酸酯，c)光催化剂，其能够通过氧化还原过程产生自由基并具有激发态氧化还原电位在小于-0.2V至不小于-2.5V的范围内，和d)自由基前体，其具有0.5V至-2V范围内的基态氧化还原电位，其中条件是自由基前体的基态电位大于光催化剂的激发态氧化还原电位。
山梨酸的酯，也称为山梨酸酯或山梨酸盐酯，优选在20℃下为液体，并且优选沸点高于250℃。合适的山梨酸酯的实例包括：
优选的山梨酸酯是三甘醇二山梨酸酯和丙二醇单山梨酸酯(两种异构体)，如图所示：
山梨酸酯可以以各种方式制备，例如WO2015/157929A1中描述的那些。
光催化剂(P)能够通过氧化还原过程产生自由基；此外，光催化剂具有小于-0.2V且不小于-2.5V的激发态氧化还原电位(E1/2[P+·/P*])。使用Rehm和Weller方程，激发态还原电位由基态氧化还原电位(通过循环伏安法测量)以及基态和激发态的零振动能级之间的能隙(由最低单线态荧光光谱中的0-0振动跃迁确定)计算。(见Wayne E.Jones，Jr.和MaryeAnne Fox J.Phys.Chem.1994,98,5095-5099)。合适种类的光催化剂的实例包括苝和N-烷基和N-芳基吩噻嗪。优选地，光催化剂是N-苯基吩噻嗪、N-C1-C6-烷基吩噻嗪如N-甲基吩噻嗪、苝或苝衍生物，苝衍生物的特征在于下式之一：
其中Z是O、NH或N-甲基。
本文报道的所有氧化还原电位均参照标准氢电极(SHE)。光催化剂的使用浓度优选为从0.02重量％、更优选0.05重量％和最优选0.1重量％至1重量％、更优选0.5重量％和最优选0.3重量％，这基于山梨酸酯的重量。
自由基前体具有0.5V至-2V范围内的基态氧化还原电位，条件是自由基前体的基态电位大于光催化剂的激发态氧化还原电位。合适的自由基前体类的实例包括具有碳-卤键、氮-卤键、硫-卤键和氧-卤键、硫氰酸酯基或硫代氨基甲酸酯基的化合物。优选的一类自由基前体是α-卤代羰基化合物、α-卤代苄基化合物或碘鎓盐。自由基前体的优选实例是二苯基六氟磷酸碘鎓或α-溴苯基乙酸甲酯：
基于山梨酸酯的重量，自由基前体优选以0.1重量％、更优选0.2重量％、最优选0.5重量％至10重量％、更优选5重量％、最优选2重量％的范围使用。
该组合物还包括稳定的聚合物颗粒水分散体(胶乳)。合适的胶乳包括丙烯酸、苯乙烯-丙烯酸、乙烯基酯-丙烯酸、醇酸树脂和乙烯基酯-聚乙烯胶乳的稳定水分散体。胶乳的固体含量优选在30至60％的范围内，并且聚合物颗粒优选在环境温度下不成膜。
本发明的组合物还有利地包括一种或多种下列组分：颜料如TiO2；流变改性剂；不透明的聚合物；着色剂；填料；分散剂；润湿助剂；抗氧化剂；表面活性剂；共溶剂；额外的聚结剂；消泡剂；防腐剂；流动剂；流平剂；滑爽添加剂；和中和剂。
如以下实施例所示，本发明的组合物提供了一种更快地固化涂层以及具有更少黄化的方法。
实施例
对于本发明的实施例，苝(计算的激发态电位为-1.8V，基于涂料的重量为30ppm)和自由基前体(基于涂料的重量为150ppm)被添加到含有丙二醇单山梨酸酯(Sorbic PO)或三甘醇二山梨酸酯(TEG Disorbate)的涂料组合物中。涂料制剂的组分如表1所示。
表1-Master Gloss涂料制剂
TRITON、TAMOL、ACRYSOL和RHOPLEX为陶氏化学公司(The Dow Chemical Company)或其附属公司的商标。
对比例含有山梨酸酯，但既不含光催化剂也不含自由基前体。α-溴苯基乙酸甲酯(如在Helv.Chim.Acta,1990,73,2225-2241中报道，-1.0V基态氧化还原电位)被用作实施例1的自由基前体，二苯基六氟磷酸碘鎓(0.4V基态氧化还原电位，如在Polym.Chem.,2011,2,1185-1189中报道)被用作实施例2的自由基前体。
根据ASTM D4366方法，使用型号SP0500的TQC摆锤硬度测试仪，完成柯尼希硬度测量。用于柯尼希测量的涂层上用10密耳的刮刀间隙制作在Al基材上。
使用BYK-Gardner颜色引导球分光光度计在作为基材的白色Leneta图表上测量颜色。该工作最感兴趣的颜色参数是来自CIE L*a*b*颜色谱的b*值。b*值表示蓝色和黄色之间的平衡，较大的正数表示更多的黄化。经验法则表明，肉眼可以看到Δb*>0.5的色差。柯尼希硬度的结果如表2所示。
表2-具有和不具有光催化剂/自由基前体的涂层的柯尼希硬度
结果表明，对于含有光催化剂和自由基前体的样品，柯尼希硬度显着增加并且显著更快地实现了最大硬度。
还测量了组合物的固化涂层的黄化程度，如表3所示。
表3-固化涂层的黄化程度
对于含有光催化剂和自由基前体的样品，黄化程度不会显着超过在将涂料施加到基材上的第一天之后观察到的程度。即使在23天之后，对于本发明的实施例观察到的黄化程度也显着小于对比例的测量值(2.8vs.6.8和3.1vs.7.1)；此外，比较例1天后观察到的结果不太明显(2.8vs 3.2和3.1vs 4.1)。
Claims (8)
1.一种组合物，其包含a)稳定的聚合物颗粒水分散体，b)山梨酸酯，c)光催化剂，其能够通过氧化还原过程产生自由基并具有激发态氧化还原电位在小于-0.2V至不小于-2.5V的范围内，和d)自由基前体，其具有0.5V至-2V范围内的基态氧化还原电位，其中条件是所述自由基前体的基态电位大于所述光催化剂的激发态氧化还原电位。
2.根据权利要求1所述的组合物，其中所述稳定的聚合物颗粒水分散体是丙烯酸、苯乙烯-丙烯酸、乙烯基酯-丙烯酸、醇酸树脂或乙烯基酯-聚乙烯胶乳；其中所述山梨酸酯选自：
3.根据权利要求2所述的组合物，其中所述光催化剂是苝、N-C1-C6-烷基吩噻嗪或N-芳基吩噻嗪；以及所述自由基前体是具有碳-卤键、氮-卤键、硫-卤键和氧-卤键、硫氰酸酯基或硫代氨基甲酸酯基的化合物。
4.根据权利要求3所述的组合物，其中所述光催化剂是苝、N-甲基吩噻嗪、N-苯基吩噻嗪，或下式之一的化合物：
其中Z是O、NH或N-甲基；和
其中所述自由基前体是六氟磷酸碘鎓或α-溴苯基乙酸甲酯。
5.根据权利要求4所述的组合物，其中所述光催化剂的浓度基于所述山梨酸酯的重量为0.02-1重量％；其中所述自由基前体的浓度基于所述山梨酸酯的重量为0.1-10重量％。
6.根据权利要求5所述的组合物，其中所述稳定的聚合物颗粒水分散体是丙烯酸或苯乙烯-丙烯酸胶乳，所述光催化剂的浓度基于所述山梨酸酯的重量为0.1-0.5重量％；其中所述自由基前体的浓度基于所述山梨酸酯的重量为0.5-2重量％；并且其中所述山梨酸酯是丙二醇单山梨酸酸酯或三甘醇二山梨酸酯。
7.一种组合物，其包含：
a)稳定的聚合物颗粒水分散体，
b)山梨酸酯，
c)选自N-苯基吩噻嗪、N-甲基吩噻嗪、苝和苝衍生物的光催化剂，苝衍生物的特征在于下式：
其中Z是O、NH或N-甲基，和
d)自由基前体，其是六氟磷酸碘鎓或α-溴苯基乙酸甲酯。
8.根据权利要求7所述的组合物，其中所述山梨酸酯是丙二醇单山梨酸酸酯或三甘醇二山梨酸酯；其中所述光催化剂的浓度基于所述山梨酸酯的重量为0.1-0.5重量％；其中所述光催化剂是N-苯基吩噻嗪、N-甲基吩噻嗪或苝；并且其中所述自由基前体的浓度基于所述山梨酸酯的重量为0.5-2重量％。
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| JP2005179511A (ja) * | 2003-12-19 | 2005-07-07 | Dainippon Ink & Chem Inc | ラジカル重合性塗料組成物 |
| US20080305349A1 (en) * | 2007-06-05 | 2008-12-11 | Sun Chemical Corporation | Energy-curing breathable coatings (combined) |
| WO2015157929A1 (en) * | 2014-04-16 | 2015-10-22 | Dow Global Technologies Llc | Sorbate ester or sorbamide coalescent in coatings formulation |
| US20150361290A1 (en) * | 2014-06-16 | 2015-12-17 | Rohm And Haas Company | Remediation of yellowing in a coatings formulation containing a sorbate ester or a sorbamide coalescent |
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| US7232595B2 (en) * | 2002-11-07 | 2007-06-19 | Corning Incorporated | Device comprising low outgassing photo or electron beam cured rubbery polymer material |
| WO2007094922A2 (en) * | 2006-01-20 | 2007-08-23 | Archer-Daniels-Midland Company | Levulinic acid ester derivatives as reactive plasticizers and coalescent solvents |
| BR112012014890B1 (pt) * | 2009-12-17 | 2019-08-13 | Dsm Ip Assets Bv | Resina líquida curável por radiação para fabricação aditiva compreendendo um fotoiniciador catiônico borato triaril sulfônio, processo para formação de um objetotridimensional e objeto tridimensional compreendendo a resina liquida curável por radiação |
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- 2016-04-08 CN CN201680085792.4A patent/CN109153874A/zh active Pending
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| JP2005179511A (ja) * | 2003-12-19 | 2005-07-07 | Dainippon Ink & Chem Inc | ラジカル重合性塗料組成物 |
| US20080305349A1 (en) * | 2007-06-05 | 2008-12-11 | Sun Chemical Corporation | Energy-curing breathable coatings (combined) |
| WO2015157929A1 (en) * | 2014-04-16 | 2015-10-22 | Dow Global Technologies Llc | Sorbate ester or sorbamide coalescent in coatings formulation |
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| WO2017173646A1 (en) | 2017-10-12 |
| EP3440141A4 (en) | 2019-10-09 |
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