CN101668820A - 含有聚醚的分散和乳化树脂 - Google Patents
含有聚醚的分散和乳化树脂 Download PDFInfo
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- CN101668820A CN101668820A CN200880012824A CN200880012824A CN101668820A CN 101668820 A CN101668820 A CN 101668820A CN 200880012824 A CN200880012824 A CN 200880012824A CN 200880012824 A CN200880012824 A CN 200880012824A CN 101668820 A CN101668820 A CN 101668820A
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- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920006276 ketonic resin Polymers 0.000 description 1
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- 150000002605 large molecules Chemical class 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 239000012860 organic pigment Substances 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229960003351 prussian blue Drugs 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- MLCPSWPIYHDOKG-BUHFOSPRSA-N trans-isoindigo Natural products O=C\1NC2=CC=CC=C2C/1=C1/C2=CC=CC=C2NC1=O MLCPSWPIYHDOKG-BUHFOSPRSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
本发明涉及用于固体的分散树脂,该树脂可通过如下方法获得:将羰基氢化的酮-醛树脂的羟基基团与一种或者多种环氧乙烷类进行部分或者完全反应,以及,如果需要的话,与有机酸和/或无机酸进行后续的完全或部分酯化反应。
Description
技术领域
本发明涉及创新的分散树脂,也涉及它们的制备,还涉及分散固体的用途。
背景技术
为了在液体介质中分散固体(例如,填料、染料或颜料),习惯做法是利用分散剂来实现有效地分散固体,减小分散所需的机械剪切力,同时还能够实现很高的填充度。分散剂可帮助使附聚物破裂,作为表面活性材料,分散剂润湿和/或覆盖在要分散的颗粒表面,并且稳定化这些颗粒以抵抗不需要的再附聚(reagglomeration)。
在涂料、光油(varnish)、印刷油墨,以及其它涂布材料的制备中,分散剂有助于固体,诸如填料和颜料的引入,例如,其作为重要配方组分,是所述体系的外观和物理化学性能的基本决定因素。最优应用方式首先需要的是,这些固体均匀地分散在配置物中,其次是一旦达到分散状态,就被稳定化。
目前有大量不同的物质用作固体的分散剂。除了非常简单的、低分子量的化合物,诸如卵磷脂、脂肪酸及其盐,和烷基酚乙氧基化物(alkylphenolethoxylate)外,更多复杂的、高分子量的化合物也用作分散剂。氨基-官能化(amino-functional)和酰氨基官能化(amido-functional)体系在此处应用尤其广泛。
例如,US-A-4224212、EP-B-0208041、WO-A-00/24503和WO-A-01/21298,描述了基于聚酯-改性的多元胺的分散剂。DE-B-19732251描述了多元胺盐及其作为颜料和填料分散剂的用途。
然而,所述产品的使用,也导致了多种多样的缺点:当它们用在颜料糊状物中时,经常需要高用量含量的分散性添加剂;糊状物可达到的着色水平令人失望地低;糊状物的稳定性不够,由此它们的粘度一致性不够;以及絮凝和附聚现象难以完全避免。在许多情况下,糊状物在储存后缺乏色调一致性,并且缺乏与不同粘合剂之间的相容性。使用已知的分散添加剂在很多情况下会对涂布材料的耐水性和光稳定性产生不利影响,另外它会进一步稳定在生产和加工过程中产生的不需要的泡沫。另外,由于分散树脂在众多稀释介质(letdown vehicles)中缺乏相容性,光泽度常常受到不利影响。
因此,存在不断增长的需求,要求用于固体的分散剂能显示出相对于现有技术水平进一步改进的性能。对于分散剂的要求是,其对多种不同固体能具有很高的稳定作用。
例如,通过更有效的分散剂,才有可能降低高价颜料的使用含量,而不用必须接受着色强度的降低。
另外,糊状物、涂料、光油、印刷油墨和含有染料的其他涂布材料或固体,比如填料和/或颜料的粘度特性,例如,是由所使用的分散剂来严格地共同决定的。这里特定对于分散剂的需求,导致了液体涂料和光油的极低粘度,同时该需求也使得该粘度优选地保留了牛顿粘度行为。
此外,在建筑涂料工业领域,在合适时含有助溶剂的水性颜料糊状物,普遍地在直链丙烯酸酯,苯乙烯-丙烯酸酯或者基于硅酸酯的水性乳液涂料中,并且也用在非极性、长油醇酸树脂基装饰涂料中用于着色。
更适合这一目的的是磷酸酯。
磷酸酯及其作为分散剂的用途是已知的,并且可以在现有技术中找到。例如,US-A-4720514,描述了有利于配置水性颜料分散体的一系列烷基酚乙氧基化物(alkylphenol ethoxylate)的磷酸酯。EP-A-0256427中也描述了相似用途的磷酸酯。另外,DE-A-3542441公开了嵌段共聚物的二磷酸单酯(bisphosphoric monoester)以及它们的盐。同时描述了它们作为分散剂和乳化剂的可能用途,尤其是在农作物保护配方制备中的用途。US-A-4872916描述了基于线型或支化脂肪族的环氧烷烃的磷酸酯作为颜料分散剂的用途。在US-A-3874891中以同样的方式概述了相应的硫酸盐的用途。文献US-A-5130463和US-A-5151218分别报道了基于羟基封端的加聚产物和缩聚产物的磷酸酯,其可用于高填充聚酯模塑化合物,尤其是SMC和BMC配方(SMC,sheet molding compounds=片状模塑化合物;BMC,bulk moldingcompounds=块状模塑化合物)的制备。J.Appl.Polym.Sci.65,2545(1997)中描述了通过Mannich-Moedritzer反应制备的双官能磷酸酯以及其在碳酸钙上的吸附特性。US-A-4456486中描述的主要论题包括脂肪醇和烷氧基化的脂肪醇的酸性或者中性磷酸酯作为处理特定蓝色颜料的试剂的用途。以同样的方式,EP-A-0256427描述了烷氧基化的脂肪醇的磷酸酯用于制备颜料分散体的用途,所述颜料据称适用于水性应用场合。US-A-4720514描述了通过不同结构的烷氧基化磷酸酯制备的颜料分散体。US-A-4698099描述了含有作为其分散剂的单羟基封端聚酯的磷酸酯的颜料分散体。
DE-A-3930687描述了磷酸酯(OH)3-nPO-(OR)n及其盐,其特征在于R代表一个不含有Zerewitinoff氢的脂肪族、脂环族和/或芳香族基团,其含有至少一个醚氧原子(-O-)和至少一个羧酸片段(-COO-)和/或氨酯基团(-NHCOO-),且其平均分子量为200至10,000,脂肪族基团上的一些氢原子可被卤素原子取代;分子中(或每个基团R)中羧酸酯基团和/或氨酯基团数的比例在1∶20至20∶1的范围内,且n代表1或2。同时,特别详细说明的是这些磷酸酯作为分散剂的用途。
上述磷酸酯用于制备乳液聚合物的用途也是已知的,重点放在这些乳液聚合物的快速着色(ready pigmentability)上,特别地包括低凝固物含量的乳液聚合物(DE-A-19810658,JP-A-11-246799,和WO99/46337)。
DE-A-19806964特别描述了基于聚苯乙烯-嵌段-聚环烷氧共聚物的磷酸酯,其自单官能引发剂(starter)醇开始,通过依次加入氧化苯乙烯和环氧烷烃来进行制备。这些磷酸酯的特点包括在其制备过程中使用了至少2mol氧化苯乙烯。同样描述到的是磷酸酯作为颜料和填料分散剂的用途。DE-A-19940797描述了非离子型、嵌段共聚的、含有氧化苯乙烯的聚环氧烷烃作为低泡颜料润湿剂的用途,该嵌段共聚物的特点包括在其制备过程中使用了低于2mol的氧化苯乙烯。
所述已知的磷酸酯具有使其一般说来不能被普遍使用的缺点,因为其常常在分散添加剂和粘合剂之间或者在分散添加剂和周围介质(水或者含溶剂配方)之间缺乏足够的相容性。很大一部分也是由于磷酸酯的化学结构引起的:在水性配方中,优选只使用那些磷酸酯,其在分子中没有另外的可水解的官能团,诸如酯基或者氨酯基团。经常需要加入高含量的分散添加剂,来抑制如下现象:发生团聚;能够达到的填充度令人失望地低;分散体的稳定性且其粘度的一致性常常不充分;絮凝和附聚不能总是避免,并且由此可能存在明显的间隙和流动缺陷和表面缺陷。
在涂料和印刷油墨工业中,含有氧化苯乙烯的嵌段共聚物的应用除去了这些缺点中的一部分。已知的共聚物包括(DE-A-19806964)聚氧化苯乙烯-嵌段-聚环氧烷烃共聚物,其从单官能引发剂醇类开始,通过依次加入至少2mol的氧化苯乙烯和环氧烷烃,且随后经过磷酸化反应来形成相应的磷酸酯。
如我们自己全面的调查结果所显示的,与这些产品共有的一个特性是一定量的残留游离氧化苯乙烯含量。氧化苯乙烯能够导致健康损害。因此,在围绕由化学产品施加的毒理学和环境风险的持续争论中,发展和提供不含有氧化苯乙烯的产品是至关重要的。
发明内容
因此,本发明的目的就是要消除现有技术存在的一个或者多个缺点。本发明一个特别目的是提供用于固体的分散剂,其在广泛基础上显示出提高了的分散性能,并且对包含固体的配方的粘度和流变特性具有积极的影响。
令人吃惊地,目前已发现,上述目标是通过用于固体的新型分散树脂的方式可达到,该树脂可通过如下工艺过程获得,其包括羰基氢化的酮-醛树脂的羟基基团与一种或者多种环氧乙烷类进行的部分或者完全反应,以及,如果需要的话,后续的与有机酸和/或无机酸进行的完全或部分酯化反应。
在羰基-氢化的酮-醛(ketone-aldehyde resin)树脂与一种或多种环氧乙烷类化合物的反应中,并且任选地随后与有机和/或无机酸进行完全或部分酯化,根据本发明,优选使用如通式(I)所示的环氧乙烷类化合物:
其中,R是任选取代的、任选含有杂原子的脂肪族、脂环族、芳族或芳代脂肪族烃基,优选为具有1到10个C原子的烷基或者氢,并且
Ra和Rb可以相同或者不同,并且可以是氢或者是可与环氧乙烷的两个碳原子一起形成5元至8元环,更具体地说是6元环的烷基,并且
e=0或1。
本发明进一步地提供通式(II)的化合物
K-(OX)W (II)
其中,
K是羰基氢化的酮-甲醛树脂,并且
X是氢原子或基团Y,Y=[(C1H21O)a-(CmH2mO)b-(CnH2nO)c-(SO)d-Z],
a、b和c彼此独立地是从0到100,优选5到35,更特别地是10到20的值,前提条件是a+b+c的总和>0,
d等于0到10,优选<5,更特别地是0,
l、m和n彼此独立地为≥2到14,优选2到4,
w是2到15,优选3到12,更特别地是4到12,
SO是氧化苯乙烯,并且
Z是氢和/或选自磺酸类、硫酸类、膦酸类、磷酸类、羧酸类、异氰酸酯类、环氧化物类中的基团,更优选地是磷酸和(甲基)丙烯酸,
其前提条件是基团Y在该分子中至少出现一次。
根据本发明,优选的通式(II)的化合物是那些其中Z是单酯化和/或二酯化磷酸的基团。
本领域技术人员清楚地知道这些化合物可以混合物的形式存在,其分散基本上是按统计学规律控制的。这不仅应用于环氧乙烷基团的分布,而且也应用于酸基团及其酯化,即单酯类、二酯类和三酯类的程度的分布,酯键可以是分子间和/或分子内。在一个特定的实施方案中,环氧乙烷基团也可以以嵌段排列。
本发明还提供了上述反应产物的用途,更具体的说是通式(II)的化合物作为用于固体的分散剂的用途,更具体的说是针对含有粘合剂和不含粘合剂的颜料糊状物、涂布材料、印刷油墨和印刷光油的制备。
本发明还提供了在液体介质中的固体分散体,其包含至少一种上述反应产物和/或通式(II)的化合物。
本发明另外的主题体现在权利要求中。
可以用在反应中的羰基氢化的酮-醛树脂,全部都为已知树脂。
人们已知酮-甲醛树脂很长时间了。其制备工艺在,例如DE3324287、US2540885、US2540886、DE1155909、DD12433、DE1300256和DE1256898中都有描述。
一般地,在制备中,酮和甲醛是在碱的存在下彼此进行反应的。
酮-醛树脂在涂布材料中用作例如成膜添加剂组分,以便改进特定性能,诸如初始干燥速度、光泽度、硬度或者抗划性。由于其相对低的分子量,典型的酮-醛树脂具有低的熔体粘度和溶液粘度,因此其在涂布材料中与其它材料一起用作成膜功能填料。
通过辐射,例如,太阳光,酮-醛树脂的羰基会发生常规的降解反应,例如Norrish类型I或II中的那些[Laue,Plagens,Namen-undSchlagwort-Reaktionen,Teubner Studienbücher,Stuttgart,1995]。
因此,不可能将未改性的酮-醛树脂或者酮树脂应用于外面部分(exterior sector)的高质量应用场合,例如,那些需要高抵抗性能,更具体地说是耐候性和耐热性方面的应用场合。这些缺点可以通过氢化羧基基团来弥补。通过酮-醛树脂的氢化将羰基基团转化成仲醇已经实践了很长一段时间(DE826974、DE870022、JP11-012338、US6222009)。
在含有芳族基团的酮的基础上制备羰基-氢化的酮-醛树脂和环-氢化的酮-醛树脂是同样可行的。这些类型的树脂在DE3334631中有描述。
然而,并没有描述羰基-氢化的酮-醛树脂进行烷氧基化的文献。
根据本发明,特别优选的是,基于甲醛的羰基-氢化的酮-醛树脂,其基本上含有通式(III-a)至(III-c)的结构单元。
其中
R是具有6-14个碳原子的芳族烃基,或者是具有1-12个碳原子的(环-)脂族烃基,
R′=H或者CH2OH,
k=2到15,优选3到12,更优选是4到12,
m=0到13,优选0到9,
l=0到2,
k+l+m的总和在5至15之间,且k>m,优选在5-12之间,这三个结构单元能够交替或无规分布,且该结构单元通过CH2基团直链连接和/或通过CH基团进行支化连接,
所述羰基-氢化的酮-醛树脂通过如下步骤获得
A)在至少一种碱性催化剂和如果需要的话至少一种相转移催化剂的存在下,无溶剂或者使用能与水混溶的有机溶剂,通过将至少一种酮与至少一种醛进行缩合来制备基础树脂(base resin),
并且随后
B)使在A)中获得的酮-醛树脂的羰基与氢在催化剂的存在下,在50至350bar之间,优选100至300bar,更优选150至300bar之间的压力,40至140℃之间,优选50至140℃之间的温度进行连续的、半分批或者分批的氢化反应,其中所述酮-醛树脂在熔融状态下或者在合适溶剂的溶液中。
这些化合物及其制备方法是专利申请DE102006009079.9的主题,该申请在本说明书的优先权日之前没有出版,在此将其通过引用加入。
另外,本发明优选的是基于双-反应活性酮和甲醛的羰基-氢化的酮-醛树脂,其基本上含有通式(IV)的结构单元
其中R’=H、含有1至12个碳原子的脂族烃基或CH2OH,
R1和R2=H、具有1到18碳原子的脂肪族和/或环脂族烃基,
其中,R1和R2可以相同或不同,或者是环脂族环连接(jointcycloaliphatic ring)的一部分,
k=1到15,优选2到12,更优选是3到12,
l=1到13,优选1到9,
m=0到2,
k+l+m的总和在3到15之间,优选4到12之间,三个结构单元可以是交替分布也可以是无规分布,该结构单元可以通过CH2基团直链连接,并且在R1和/或R2=H的情况下,该结构单元也可以通过CH2基团支化连接,
所述酮-醛树脂通过如下步骤获得
A)在至少一种碱性催化剂和,如果需要的话,至少一种相转移催化剂的存在下,无溶剂或者使用一种能与水混溶的有机溶剂,将至少一种酮与至少一种醛进行缩合来制备基础树脂(base resin),
并且随后
B)使酮-醛树脂(A)的羰基与氢在催化剂的存在下,在50至350bar之间,优选100至300bar,更优选150至300bar之间的压力,在40至140℃之间,优选50至140℃之间的温度进行连续的、半分批或者分批的氢化反应,其中所述酮-醛树脂(A)在熔融状态下或者在合适溶剂的溶液中。
这些化合物及其制备方法是专利申请DE102006009080.2的主题,该申请在本说明书的优先权日之前没有出版,在此将其通过引入加入。
环氧烷烃的实例是一种或者多种选自如下的化合物:环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯、十二碳烯氧化物、十四碳烯氧化物、2,3-二甲基环氧乙烷、环戊烯氧化物、1,2-环氧戊烷、2-异丙基环氧乙烷、缩水甘油基甲基醚,缩水甘油基异丙醚、表氯醇、3-甲氧基-2,2-二甲基环氧乙烷、8-氧化二[5.1.0]辛烷(8-oxabicyclo[5.1.0]octane)、2-戊基环氧乙烷、2-甲基-3-苯基环氧乙烷、2,3-环氧丙基苯、2-(4-氟苯基)环氧乙烷和四氢呋喃,以及它们的纯对映异构体对或者对映异构体混合物。
通过环氧烷烃烃彼此之间及其与树脂K之间的比率,可以共同决定诸如,例如,亲水性/疏水性、熔化范围、粘度、硬度等性能。这属于本领域技术人员熟知的规律。
本发明目的所针对的固体原则上可以是任何有机或者无机的固体材料。
这些固体的实施例是颜料、填料、染料、荧光增白剂、陶瓷材料、磁性材料、纳米分散固体、金属、生物杀灭剂、农用化学品,以及以分散体的形式使用的药物。
优选的固体是由,例如,Colour Index,Third Edition,Volume 3;TheSociety of Dyers and Colourists(1982),及其后续修订版中指定的颜料。
颜料的实例是无机颜料,诸如炭黑、二氧化钛、氧化锌、普鲁士蓝、氧化铁、镉硫化物、铬颜料,如铬酸盐、钼酸盐和混合铬酸盐,和铅、锌、钡、钙的硫酸盐,及它们的混合物。无机颜料进一步的实例由H.Endriss在Aktuelle anor-ganische Bunt-Pigmente,Vincentz Verlag,Hanover(1997)一书中给出。
有机颜料的实施例选自偶氮、二偶氮、稠合偶氮、萘酚、金属络合物、硫靛、靛蒽醌、异靛蒽醌、蒽嵌蒽二酮、蒽醌、异二苯并蒽酮、三吩二噁嗪(triphendioxazine)、喹吖啶酮(quinacridone)、二萘嵌苯(perylene)、二酮基吡咯并吡咯(diketopyrrolopyrrole)、酞青颜料。有机颜料更进一步的实例在W.Herbst,K.Hunger的Industrial Organic Pigments,VCH,Weinheim(1993)一书中给出。
进一步优选的固体是填料,诸如滑石、高岭土、硅石、重晶石和石灰;陶瓷材料,诸如氧化铝、硅酸盐、锆氧化物、钛氧化物、氮化硼、氮化硅、碳化硼、混合的硅/铝氮化物、和金属钛酸盐,例如;磁性材料,诸如过渡金属的磁性氧化物,诸如氧化铁、钴-掺杂的氧化铁、和铁酸盐、例如;金属,比如铁、镍、钴、及其合金,例如;以及生物杀灭剂、农用化学品、和药物,诸如杀真菌剂,例如。
用于实现本发明目的的颜料糊状物、涂布材料、印刷油墨和/或印刷光油可以是多种产品中的任何一种。例如,它们可以是含有填料、颜料和/或染料的体系。作为液体介质,它们可以含有有机溶剂和/或水,作为目前已知的,作为目前工艺水平,作为所用粘合剂的功能。另外,也有可以把粘合剂组分,诸如多元醇,例如,作为液体介质。
然而,涂布材料、印刷油墨和/或印刷光油不需要必须含有液相,反而也可以是所谓的粉末涂布材料。
该涂布材料、印刷油墨和/或印刷光油也可以含有常规的现有技术中的添加剂,诸如,例如,润湿剂、流动控制剂或消泡剂等等,并且可以根据现有技术通过多种方法进行固化、交联和/或干燥。
为实现本发明的目的的涂布材料的实例是涂料、光油、印刷油墨,以及其它涂布材料,比如含溶剂的涂布材料和无溶剂的涂布材料、粉末涂布材料、UV固化涂布材料、低固含量、中固含量和高固含量、汽车漆、木材漆、烤漆、2K(双组分)涂布材料、金属涂布材料和调色剂组合物。涂布材料更进一步的实例在Bodo Müller,Ulrich Poth,Lackformulierung undLackrezeptur,Lehrbuch für Ausbildung und Praxis,Vincentz Verlag,Hanover(2003)和P.G.Garrat,,Vincentz Verlag,Hanover(1996)中给出。
为实现本发明目的的印刷油墨和/或印刷光油的实例是溶剂基印刷油墨、柔版印刷油墨、凹版印刷油墨、活版印刷(letterpress)或凸版(relief)油墨、胶印油墨、平版印刷油墨、用于印刷包装的印刷油墨、丝网印刷油墨、用于喷墨打印机的油墨、喷墨油墨(ink-jet ink),和印刷光油,比如叠印光油(overprint varnish)。
印刷油墨配方和/或印刷光油配方的进一步的实例在E.W.Flick,PrintingInk and Overprint Varnish Formulations-Recent Developments,NoyesPublications,Park Ridge NJ,(1990),及其后续版本中给出。
本发明的分散树脂可以用在颜料糊状物、涂布材料、印刷油墨和/或印刷光油中,其重量浓度可以为0.01%到90.0%,优选0.5%到35%,更优选1%到25%。在适当时,它们可以通过与现有技术的润湿剂和分散剂形成混合物的形式来使用。
具体实施方式
实施例:
本发明用下述实施例进行了更详细的说明。
反应物:羰基-氢化的酮-醛树脂
所述羰基-氢化的酮-醛树脂的制备方法如下:
用于进一步氢化的基于苯乙酮和甲醛的基础树脂的制备
将1200g苯乙酮、220g甲醇、0.3g苄基三丁基氯化铵,以及360g的浓度为30%的甲醛水溶液加入到容器中并且搅拌均匀。然后,边搅拌,边加入32g浓度为25%的氢氧化钠水溶液。然后,在80至85℃,在90分钟内,边搅拌边加入655g浓度为30%甲醛水溶液。在回流温度下搅拌5小时后,关闭搅拌器,从树脂相中分离出水相。粗产物用已经加有乙酸的水清洗,洗涤一直持续直到树脂的熔融样品变得透明。此时将树脂通过蒸馏来干燥。
这样得到了1270g浅黄色(pale yellowish)树脂。该树脂透明且脆,其熔点为72℃。加纳尔色数(Gardner color number)为0.8(在乙酸乙酯中为50%)。其可溶于例如,乙酸酯,诸如乙酸丁酯和乙酸乙酯,以及芳烃,诸如甲苯和二甲苯。其不溶于乙醇。甲醛含量是35ppm。该产物称作基础树脂。
基于苯乙酮和甲醛的基础树脂的氢化
羰基-氢化的酮-醛树脂I:
通过加热将300g的基础树脂溶解在700g的异丁醇中。然后,在260bar、120℃,在具有装有100ml的Raney型镍催化剂的催化剂筐的高压釜(来自Parr)中,进行氢化反应。8小时后,将反应混合物通过过滤器从反应器中引导出来。
羰基-氢化的酮-醛树脂II:
将300g的基础树脂溶解在700g的四氢呋喃(水含量约7%)中。然后,在260bar、120℃,在具有装有100ml商业上常用的Ru催化剂(氧化铝上有3%的Ru)催化剂筐的高压釜(来自Parr)中,进行氢化反应。20个小时后,将反应混合物通过过滤器从反应器中导出。
羰基-氢化的酮-醛树脂III:
将基础树脂通过加热溶解在异丁醇中,得到浓度为30%的溶液。氢化反应发生在连续操作的固定床型反应器中,其装有400ml商业上常用的负载在硅石上的铜/铬催化剂。在300bar、130℃,将500ml/h的反应混合物从顶到底通过反应器(滴流模式)。通过外部供应氢气来使压力保持不变。
将实施例I到III中的羰基-氢化的酮-醛树脂溶液在真空中除去溶剂,从而得到相应的羰基-氢化的酮-醛树脂I-III。
羰基-氢化的酮-醛树脂与一种或多种环氧烷烃的反应,以及如果需要的话,与磷酸的完全或部分酯化反应
本发明聚醚的制备在DE10029648中有详细描述。得到的改性聚醚具有如下通式
[U-(SO)e(EO)f(PO)g(BO)h]iP(O)(OH)3-i
其中
U=羰基-氢化的酮-醛树脂,
SO=-CH2-CH(Ph)-O-,其中Ph=苯基,
EO=环氧乙烷,
PO=环氧丙烷,
BO=环氧丁烷。
表1
实施例 | 羰基氢化的酮-醛树脂编号 | e | f | g | h | i |
A1 | I | 4 | 4 | 4 | 0 | 3.0 |
A2 | II | 0 | 20 | 0 | 0 | 0.7 |
A3 | III | 1 | 9 | 0 | 0 | 1.0 |
A4 | I | 3 | 0 | 0 | 2 | 1.0 |
A5 | II | 2 | 0 | 4 | 0 | 3.0 |
A6 | III | 0 | 9 | 0 | 0 | 3.0 |
A7 | I | 4 | 4 | 4 | 0 | 0.3 |
A8 | II | 1 | 5 | 0 | 0 | 1.0 |
A9 | III | 1 | 9 | 0 | 0 | 1.0 |
A10 | I | 3 | 0 | 0 | 2 | 2.5 |
A11 | II | 2 | 0 | 4 | 0 | 1.0 |
A12 | III | 0 | 9 | 0 | 0 | 0.5 |
A13 | I | 4 | 4 | 4 | 0 | 1.0 |
A14 | II | 0 | 20 | 0 | 0 | 0.9 |
A15 | III | 3 | 0 | 0 | 2 | 0.9 |
A16 | II | 0 | 10 | 0 | 0 | 0.9 |
A17 | II | 0 | 9 | 0 | 0 | 3.0 |
A18 | III | 4 | 4 | 4 | 0 | 1.0 |
A19 | I | 1 | 5 | 0 | 0 | 1.0 |
A20 | II | 1 | 9 | 0 | 0 | 1.0 |
A21 | III | 3 | 0 | 0 | 2 | 2.5 |
上面为单体环氧烷烃设置的顺序并不代表对得到的聚醚结构的任何限制,而是代表一种示例性的排列,在这一点上特别指出的是,使用上述单体,聚醚既可形成无规构造也可形成嵌段构造。本领域技术人员熟知,改性或未改性的聚醚可通过磷酸化反应进行制备,并且该反应是无规进行的。i的值代表了聚醚和磷酸酯基团之间的摩尔比率。i值可在0到2.9之间变化。
应用实施例:
作为对比例,使用脂肪酸乙氧基化物B1(Tego Dispers 740W,Tego),带有9mol环氧乙烷的壬基苯酚乙氧基化物B2(Berol 09,Akzo)、相应的单磷酸酯衍生物B3(Berol 733,Akzo),以及用10ml EO乙氧基化的油醇B4(Alkanol 010,Tego)。
用于检验本发明中用作分散添加剂的化合物,以及还有对比化合物的活性的方法步骤如下:
颜料糊状物的制备
为了制备颜料糊状物,将相应的添加剂与水,以及如果合适的话消泡剂混合在一起,随后加入颜料。加入研磨介质(2-3mm的玻璃珠,其体积与颜料糊状物相同)后,在带有空气冷却的Skandex搅拌器中进行分散一小时(无机颜料)或者两小时(有机颜料和炭黑)。
蓝色糊状物的配方
该蓝色糊状物的配制如下(以重量百分比%计量):
45.9%的水,
12.2%的本发明化合物或者对比化合物(基于100%的固体),
1.0%的消泡剂(Tego Foamex 830,Tego Chemie Service GmbH),
40.8%的染料(Heliogenblau 7080,蓝色染料,BASF),
黑色糊状物的配方
该黑色糊状物的配制如下(以重量百分比%计量):
56.9%的水,
15.0%的本发明化合物或者对比化合物(基于100%的固体),
1.0%的消泡剂(Foamex 830,Tego Chemie Service GmbH),
27.0%的颜料(Flammru β101 lamp black,Degussa)。
红色氧化铁的糊状物的配方(以重量百分比%计量):
25.8%的水,
8.1%的本发明化合物或者对比化合物(基于100%的固体),
65.0%的红色氧化铁(Bayferrox 140M,Bayer)。
本发明中颜料糊状物的制备可以用更低浓度的消泡剂(0.8%而不是1.0%)进行,这是由于这些情况下降低的泡沫稳定性。
测试涂料
白色涂料1(水性)
白色涂料2(溶剂型)
以1g颜色糊状物配25g白色涂料的比例,人工混合颜色糊状物与白色涂料,来制备有色涂料。
糊状物稳定性测试
为了测试该糊状物的稳定性,可在两个不同的剪切速率(20l/s和1000l/s)下测定可达到的初始粘度以及在50℃下存储四周后的粘度。
蓝色糊状物
样品 | 粘度/Pas初始在20l/s | 粘度/Pas初始在1000l/s | 粘度/Pas4周后50℃在20l/s | 粘度/Pas4周后50℃在1000l/s |
A1 | 1308 | 150 | 1500 | 203 |
A2 | 1150 | 130 | 1300 | 155 |
A3 | 1201 | 134 | 1380 | 160 |
A4 | 1106 | 120 | 1320 | 140 |
A5 | 1200 | 125 | 1360 | 138 |
A6 | 1170 | 140 | 1290 | 160 |
A7 | 1413 | 200 | 1800 | 250 |
B1 | 1108 | 150 | 1700 | 235 |
B2 | 1723 | 135 | 2500 | 280 |
B3 | 1306 | 130 | 190 | 190 |
B4 | 2062 | 250 | 4000 | 390 |
黑色糊状物
样品 | 粘度/Pas初始在20l/s | 粘度/Pas初始在1000l/s | 粘度/Pas4周后50℃在20l/s | 粘度/Pas4周后50℃在1000l/s |
A1 | 400 | 120 | 420 | 140 |
A2 | 360 | 100 | 380 | 130 |
A3 | 365 | 110 | 380 | 120 |
A4 | 350 | 100 | 385 | 120 |
A5 | 310 | 108 | 340 | 393 |
A6 | 405 | 120 | 420 | 140 |
A7 | 401 | 130 | 509 | 200 |
B1 | 400 | 130 | 508 | 180 |
B2 | 500 | 120 | 680 | 980 |
B3 | 420 | 130 | 740 | 182 |
B4 | 不可制备 |
氧化铁糊状物
样品 | 粘度/Pas初始在20l/s | 粘度/Pas初始在1000l/s | 粘度/Pas4周后50℃在20l/s | 粘度/Pas4周后50℃在1000l/s |
A1 | 790 | 320 | 1000 | 395 |
A2 | 650 | 395 | 903 | 425 |
A3 | 630 | 320 | 870 | 370 |
A4 | 615 | 290 | 820 | 320 |
A5 | 707 | 408 | 900 | 440 |
A6 | 720 | 326 | 890 | 370 |
A7 | 1100 | 500 | 1010 | 700 |
B1 | 1304 | 450 | 无稳定性 | 无稳定性 |
B2 | 1302 | 450 | 无稳定性 | 无稳定性 |
B3 | 1800 | 900 | 4000 | 1300 |
B4 | 900 | 160 | 无稳定性 | 无稳定性 |
本发明所研究的全部类型颜料的颜料糊状物的有效稳定性可容易地通过各种情况下粘度的小幅增长来加以证明,而同时,对比例只有在孤立的情况下才允许制备出稳定的颜料制剂。
分散性能测试
将测试配方涂敷湿膜厚度为200μm;干燥5分钟后,在1/3表面上进行擦除测试。使用X-Rite的XP68分光光度计进行比色测量。
样品 | 色度值L和b | 擦除后的Delta E |
A1 | 65.5 -31.6 | 2.2 |
A2 | 65.2 -32.1 | 2.4 |
A3 | 64.7 -32.3 | 1.9 |
A4 | 65.0 -32.0 | 2.0 |
A5 | 64.6 -32.5 | 1.8 |
A6 | 65.3 -31.9 | 1.9 |
A7 | 65.4 -31.0 | 3.5 |
B1 | 63.7 -33.9 | 0.9 |
B2 | 65.6 -30.6 | 4.3 |
B3 | 65.2 -32.0 | 3.9 |
B4 | 63.9 -31.5 | 5.7 |
样品 | 色度值L,a和b | 擦除后的DeltaE |
A1 | 75.8 13.3 4.5 | 0.4 |
A2 | 75.9 13.1 4.3 | 0.4 |
A3 | 75.8 13.4 4.2 | 0.5 |
A4 | 75.5 13.6 4.5 | 0.3 |
A3 | 75.6 13.5 4.6 | 0.4 |
A6 | 75.7 13.4 4.5 | 0.3 |
A7 | 74.8 13.2 4.0 | 1.3 |
B1 | 75.0 13.0 4.1 | 0.9 |
B2 | 74.9 13.1 4.1 | 1.2 |
B3 | 75.5 13.2 4.2 | 0.7 |
B4 | 75.2 12.9 4.7 | 0.9 |
样品 | 色度值L和b | 擦除后的Delta E |
A1 | 60.3 4.5 | 0.3 |
A2 | 60.4 4.4 | 0.2 |
A3 | 60.4 4.4 | 0.3 |
A4 | 60.6 4.5 | 0.3 |
A5 | 60.5 4.3 | 0.3 |
A6 | 60.2 4.4 | 0.1 |
A7 | 61.1 4.4 | 1.4 |
B1 | 59.1 4.4 | 0.5 |
B2 | 60.3 4.5 | 1.2 |
B3 | 62.3 4.3 | 2.4 |
B4 | 不可用 | 不可用 |
基于F681/blue的醇酸涂料
样品 | 色度值L和b | 擦除后的Delta E |
A1 | 68.0 -29.9 | 1.5 |
A2 | 68.2 -29.7 | 1.5 |
A3 | 66.7 -30.8 | 1.5 |
A4 | 67.3 -29.9 | 1.5 |
A3 | 68.0 -29.5 | 1.5 |
A6 | 67.8 -30.1 | 1.5 |
A7 | 66.5 -28.7 | 1.5 |
B1 | 88.0 -4.0 | 24.7 |
B2 | 67.5 -29.2 | 4.2 |
B3 | 68.8 -28.4 | 4.1 |
B4 | 66.3 -28.6 | 3.1 |
样品 | 色度值L、a和b | 擦除后的DeltaE |
A1 | 76.8 12.3 2.7 | 0.4 |
A2 | 75.9 12.0 2.6 | 0.3 |
A3 | 75.8 12.1 2.8 | 0.4 |
A4 | 75.5 12.2 2.7 | 0.2 |
A3 | 75.6 11.9 2.6 | 0.6 |
A6 | 75.7 11.1 2.7 | 0.3 |
A7 | 74.8 7.9 1.8 | 3.9 |
B1 | 82.0 8.0 0.9 | 2.7 |
B2 | 87.9 2.9 0.1 | 11.5 |
B3 | 79.5 9.2 1.3 | 4.8 |
B4 | 78.2 7.9 1.5 | 5.0 |
基于Alkydal F681/gray的醇酸涂料
样品 | 色度值L和b | 擦除后的Delta E |
A1 | 62.1 6.0 | 0.4 |
A2 | 62.8 6.3 | 0.3 |
A3 | 62.1 5.8 | 0.5 |
A4 | 62.3 6.1 | 0.3 |
A3 | 62.7 6.7 | 0.4 |
A6 | 62.7 6.0 | 0.6 |
A7 | 62.9 6.0 | 0.4 |
B1 | 82.3 4.2 | 8.3 |
B2 | 63.1 6.3 | 1.7 |
B3 | 63.3 6.4 | 1.2 |
B4 | 64.1 6.5 | 1.8 |
由于本发明的分散添加剂,很明显地,可以达到理想的着色强度,同时在所有情况下都可以理想地通过擦除测试。
这也是特别的情况,明显地这样,相比之下,对比例仅仅在孤立的情况下显示出良好的着色强度。特别显著的是基于所有类型颜料的水基和溶剂基体系的优异的delta E擦除值的基础上,用于本发明用途的本发明化合物的优越性。
另一个值得特别强调的特性是显著改善的部分制剂的再分散性,所述部分制剂已经干燥或者开始干燥。另外,它们具有极低的开始干燥或者干透的倾向。由此,粘度、流动特性和极好的计量可能性的必要前提,都显著地得以改善。本发明的颜料制剂具有极高的着色强度和亮度。可以达到很高的颜料浓度。不需要费力地研磨,即可制备颜料浓缩物;这些因素都与极大的经济优势有关。
乳液聚合物制剂的使用实施例
将乳化剂A2溶解在水中,并且使用氨将PH值调节到9。
初始投料:
1.5g 乳化剂A2,
250g 水,
36g 部分原料流1(原料流1:8.5g乳化剂A2,200g水,15g丙烯酰胺(在水中50%浓度),12.5g丙烯酸,242g苯乙烯,237g丙烯酸正丁酯),
5g 部分给料流2(给料流2:2.5g过氧化二硫酸钠(Naperoxodisulfate),98g水)。
在装有锚式搅拌器、回流冷凝器以及2个供料槽的聚合容器中,将初始投料在氮气氛中加热到85℃,并最初聚合15分钟。然后将给料流1计量加入超过2小时,给料流2计量加入超过2.5小时。接着聚合1小时以上。然后将产物通过一个筛目大小为500μm的筛子进行过滤,通过称量发现湿状态的凝结块部份重量比小于0.1%。分散体的固体含量在130mPas的粘度下为48%。
当使用粘合剂来配制涂料时,本发明的用于乳液聚合的这些化合物尤其具有优势,因为这些乳化剂允许在分散体中具有高颜料浓度,并且聚合物的颜料结合力也因此变得很大,其又一次,正如本领域技术人员所熟知的,导致了更高的耐湿磨性。
Claims (15)
1.一种用于固体的分散树脂,该树脂可通过如下方法获得:将羰基氢化的酮-醛树脂的羟基基团与一种或者多种环氧乙烷类进行部分或者完全反应,以及,如果需要的话,与有机酸和/或无机酸进行后续的完全或部分酯化反应。
3.如权利要求2所述的分散树脂,其中R是具有1到10个C原子的烷基。
4.如权利要求2或3所述的分散树脂,其中Ra和Rb是与环氧乙烷的两个碳原子一起形成6元环的烷基。
5.一种如通式(II)所示的分散树脂,
K-(OX)w (II)
其中,
K是羰基氢化的酮-甲醛树脂,并且
X是氢原子或基团Y,Y=[(C1H21O)a-(CmH2mO)b-(CnH2nO)c-(SO)d-Z],
a、b和c彼此独立地是从0到100的值,前提条件是a+b+c的总和>0,
d等于0到10,
l、m和n彼此独立地为≥2到14,
w=K中的OH基团数,是2到15,
SO为氧化苯乙烯,并且
Z是氢和/或选自磺酸类、硫酸类、膦酸类、磷酸类、羧酸类、异氰酸酯类、以及环氧化物中的基团,
前提条件是基团Y在该分子中至少出现一次。
6.如权利要求5所述的分散树脂,其中a、b和c彼此独立地是从5到35的值。
7.如权利要求5到6中至少一项所述的分散树脂,其中d小于5。
8.如权利要求5到6中至少一项所述的分散树脂,其中d为0。
9.如权利要求5到8中至少一项所述的分散树脂,其中l、m和n彼此独立地为2到4。
10.如权利要求5到9中至少一项所述的分散树脂,其中w为3到12。
11.如权利要求5到10中至少一项所述的分散树脂,其中Z选自由磷酸和(甲基)丙烯酸组成的组中的基团。
12.如权利要求5到10中至少一项所述的分散树脂,其中Z是单酯化的或者双酯化的磷酸的基团。
13.一种固体在液态介质中的分散体,其包含如权利要求1到12中至少一项中所述的至少一种分散树脂。
14.如权利要求1到12至少一项中所述的分散树脂的用途,所述分散树脂用作固体的分散剂。
15.如权利要求1到12至少一项中所述的分散树脂的用途,所述分散树脂用于含有粘合剂和不含粘合剂的颜料糊状物、涂布材料、印刷油墨和印刷光油的制备。
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-
2007
- 2007-04-20 DE DE102007018812A patent/DE102007018812A1/de not_active Ceased
-
2008
- 2008-03-27 JP JP2010503444A patent/JP5281638B2/ja not_active Expired - Fee Related
- 2008-03-27 WO PCT/EP2008/053604 patent/WO2008128846A1/de active Application Filing
- 2008-03-27 US US12/596,736 patent/US8420731B2/en not_active Expired - Fee Related
- 2008-03-27 CN CN2008800128243A patent/CN101668820B/zh not_active Expired - Fee Related
- 2008-03-27 EP EP08718254.9A patent/EP2137266B1/de not_active Not-in-force
- 2008-03-27 KR KR1020097021766A patent/KR101461250B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CN101668820B (zh) | 2013-10-23 |
EP2137266B1 (de) | 2014-09-10 |
JP5281638B2 (ja) | 2013-09-04 |
KR101461250B1 (ko) | 2014-11-12 |
US8420731B2 (en) | 2013-04-16 |
EP2137266A1 (de) | 2009-12-30 |
WO2008128846A1 (de) | 2008-10-30 |
JP2010525088A (ja) | 2010-07-22 |
KR20100015688A (ko) | 2010-02-12 |
DE102007018812A1 (de) | 2008-10-23 |
US20100197858A1 (en) | 2010-08-05 |
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