CN102658057A - 一种新型聚氨酯分散剂及其制备方法 - Google Patents
一种新型聚氨酯分散剂及其制备方法 Download PDFInfo
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- CN102658057A CN102658057A CN2012101095813A CN201210109581A CN102658057A CN 102658057 A CN102658057 A CN 102658057A CN 2012101095813 A CN2012101095813 A CN 2012101095813A CN 201210109581 A CN201210109581 A CN 201210109581A CN 102658057 A CN102658057 A CN 102658057A
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- compound
- anhydride
- nitrogen
- hydroxyl
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Abstract
本发明涉及一种新型聚氨酯分散剂及其制备方法，所述聚氨酯分散剂在合成时由含氮杂环化合物封端，所述含氮杂环化合物由酸酐与含一个伯胺和一个仲胺或羟基或巯基的化合物脱水缩合而成，所述缩合后的产物即所述含氮杂环化合物含有一个活泼氢；所述含一个伯胺和一个仲胺或羟基或巯基的化合物的结构式如下：
，其中n=1～5，优选2～4，R1和R2分别为含1～8个碳的烷基，两者或独立，或通过化学键相连形成一个或几个饱和或不饱和的4～8元环，X为N、O或S。
Description
技术领域
本发明涉及一种聚氨酯型分散剂及其制备方法，该分散剂用异氰酸酯多聚体与羟基化合物反应后，最后用自制的新型锚定端基封端。本发明进一步阐述了这种新型锚定端基的制备方法，以及在聚氨酯分散剂中的应用。
背景技术
在液体介质中引入固体颗粒需要强大的机械力，而且，这些固体颗粒分散于液体介质后，由于固体颗粒之间的伦敦力/范德华力引起相互吸引，进而重新聚集，破坏了分散体的稳定，导致先前所做的努力白费。因此，通常通过引入分散剂的方法来改善固体颗粒进入液体介质中的效率和提高分散体的稳定性。
分散剂是一种在分子内同时具有亲油性和亲水性两种相反性质的界面活性剂，其结构的一部分带有极性较大的锚定端基，容易吸附在固体颗粒的表面，另一部分则是极性较低的溶剂化长分子链，与分散介质(树脂或溶剂)有较好的亲和力。因此，分散剂可均一分散那些难溶于液体的无机、有机颜料的固体颗粒，同时也能防止固体颗粒的沉降和凝聚，形成较稳定的悬浮液。
随着有机颜料和碳黑在涂料、油墨以及塑料中的广泛使用，想彻底改善这些颜料在液体中的稳定性，高分子量分散剂成为一种必不可少的添加物，譬如聚丙烯酸酯类、聚氨酯类分散剂等。而其中，聚氨酯类分散剂由于其所具有的特殊聚异氰酸酯核，以及其NCO的高反应活性，能和不同极性的一元醇尾段反应生成位阻链段，因此很容易能得到对有机颜料的稳定性较强，与体系相容性广泛的高分子量分散剂，使得许多高性能的有机颜料的分散稳定不再成为问题。
US4032698提到了一种聚氨酯类分散剂，采用2.5-6个官能度的多异氰酸酯、聚丙烯酸酯一元醇以及锚定端基制备而成，锚定端基为含-SH或-OH或-NH2等反应性基团的碱性反应物，譬如双氰胺、二硝基苯胺、二氨基马来腈、3-氨基-1、2、3-三唑等。
EP154678提到了一种聚氨酯类分散剂，采用多异氰酸酯、羟基化合物以及一种含泽尼维季诺夫(zerewitinoff)活泼氢和至少一个含氮的碱性基团的化合物制备而成。其中作为锚定端基的这种含活泼氢化合物优先采用含-NH(2)的杂环化合物，譬如1-(2-氨乙基)哌嗪，3-氨基-1,2,4-三唑，4-(2-氨乙基)-吡啶等等。
WO97/26984所述的聚氨酯分散剂，除了多异氰酸酯、羟基化合物外，所用的锚定端基为Michael加成反应产物，如含活泼氢的杂环化合物与丙烯酸羟丙(乙)酯，或者含活泼氢杂环化合物与缩水甘油醚的加成产物。
CN200780044910中的聚氨酯分散剂同样采用了由Michael 加成而得的锚定端基，为二烷基胺基烷基胺与含羟基官能团的α,β-不饱和羰基化合物的反应物。
EP2007/05145的聚氨酯分散剂采用了不饱和的单羟基化合物做锚定基团，譬如炔丙醇、糠醇等，最终的产物特征是没有氨值。
上述的聚氨酯分散剂采用了不同类型的锚定端基，能较好地分散无机和部分有机颜料，但对于某些有机颜料，尤其是酞菁类、异吲哚啉类、碳黑等，均存在分散体着色力不强，色浆贮存稳定性不足的缺点。
发明内容
本发明的目的在于提供一种新型聚氨酯分散剂及其制备方法，解决上述现有分散剂存在的问题。具体方案如下：
一种新型聚氨酯化合物，所述聚氨酯化合物在合成时由含氮杂环化合物封端，所述含氮杂环化合物由酸酐与含一个伯胺和一个仲胺或羟基或巯基的化合物脱水缩合而成，所述缩合后的产物即所述含氮杂环化合物含有一个活泼氢；
所述含一个伯胺和一个仲胺或羟基或巯基的化合物的结构式如下：
其中n=1～5，优选2～4，R1和R2分别为含1～8个碳的烷基，两者或独立，或通过化学键相连形成一个或几个饱和或不饱和的4～8元环，X为N、O或S。
上述新型聚氨酯化合物的制备方法，包括如下步骤：首先，在二甲苯和醋酸丁酯混合溶液中，DBTDL（二月桂酸二丁基锡）催化作用下，组分A和组分B在70～80℃中反应，用组分B封闭掉1～95%组分A中的-NCO基团；然后，投入组分C，继续在70～80℃下反应，组分C封闭掉5～80%组分A中的-NCO基团，并且，组分B和组分C封闭的组分A的-NCO总量为30～90%；最后，60℃下保温1小时，用组分D封闭掉组分A中剩余的-NCO；其中，
组分A为一种或多种含2.0到6.0平均官能度的异氰酸酯多聚体；
组分B为聚醚或聚酯或聚丙烯酸酯的一元羟基化合物；
组分C为两官能度的扩链剂；
组分D为含氮杂环化合物。
具体地，举例来说，所述组分A即异氰酸酯多聚体是己二异氰酸酯（HDI）、甲苯二异氰酸酯（TDI）、异佛尔酮二异氰酸酯（IPDI）、4,4′-二苯基甲烷-二异氰酸酯（MDI）、苯二亚甲基二异氰酸酯（XDI）、4,4-二环己基甲烷二异氰酸酯（H12MDI）、丁二异氰酸酯（BDI）、辛二异氰酸酯（ODI）等二异氰酸酯的加成物，优选HDI、TDI、IPDI以及XDI。譬如二异氰酸酯TDI环化反应的五聚体（商品名称Desmodur IL）：
IPDI和TDI的环化自聚体：
这些多异氰酸酯多聚体具有2.0到6.0平均官能度，合适的多聚体均可购自德国Bayer公司或者意大利Sapici公司。
本发明所述的组分B可以是现有技术中任何的一元羟基化合物，优选的是聚醚、聚酯和聚丙烯酸酯一元醇。
一般地，组分B封闭掉组分A中1～90%的-NCO基团，优选地，是封闭组分A中15～60%的-NCO基团。
上述聚酯的一元羟基化合物即聚酯一元醇可以通过小分子一元醇与内酯的开环反应得到。小分子一元醇可以是含4～30个碳原子的现有技术中的任何一种醇，优选4～18个碳，譬如丁醇、戊醇、辛醇、环己醇、油醇、炔丙醇等。内酯可以是β-丙内酯、戊内酯、己内酯以及它们的衍生物。内酯与一元醇的聚合可以通过已知的工艺进行，例如在100～180℃下用对甲苯磺酸或者二丁基二月桂酸锡、四丁氧基锆做催化剂开环反应而得。譬如小分子一元醇与己内酯的开环反应反应方程式如下：
聚酯一元醇也可以通过小分子一元醇与二元醇、二元酸、酸酐缩聚而成，还可以通过小分子一元醇与羟基酸缩聚而成，或者是这两种方法的混合。
聚酯一元醇的数均分子量为300～5000，优选的分子量范围是1000～3000。
上述聚醚的一元羟基化合物即聚醚一元醇优选为烷基端基的聚(C2-4环氧烷基)一元醇，它可以通过小分子一元醇与C2-4环氧烷基单体聚合而得。其中小分子一元醇含1～30个碳，优选是1～10个碳，最优选1～4个碳，可以是甲醇、乙醇、丙醇、丁醇、1-戊醇、1-己醇、1-辛醇、月桂醇、苯甲醇、甲基苯酚、壬基酚、十二烷基苯酚等。C2-4环氧烷基基团的烷基部分可以是线性或含有支链，如环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃或者它们的共聚物。
聚醚一元醇的数均分子量为300～6000，优选的分子量范围是1000～4000。
聚丙烯酸酯一元醇是基于聚(甲基)丙烯酸酯聚合物的一个尾端为羟基的聚合物。这种聚合物可以通过(甲基)丙烯酸酯单体CH2=C(CH3)C(=O)OR在2-巯基乙醇的调聚作用下，用常规引发剂（如AIBN）制备而成。其中的R可以是含1～18个碳的烷基，优选的是1～12个碳，最优选的是1～4个碳。聚丙烯酸酯一元醇制备的反应方程式示例如下：
聚丙烯酸酯一元醇的数均分子量为300～20000，优选的分子量范围是500～10000。
所述聚醚的一元羟基化合物优选为烷基端基的聚(C2-4环氧烷基)一元醇，它可以通过小分子一元醇或者一元羧酸与C2-4环氧烷基单体开环聚合而得。
所述聚丙烯酸酯的一元羟基化合物由(甲基)丙烯酸酯单体CH2=C(CH3)C(=O)OR在2-巯基乙醇的调聚作用下，用常规引发剂制备而成，数均分子量为300～20000，优选的是500～10000。其中R是含1～18个碳的烷基，优选的是1～12个碳，最优选的是1～4个碳。
所述两官能度的扩链剂即组分C是数均分子量为600～2000的二元醇、二元胺或二元羧酸，优选的是聚烷氧基二元醇、聚酯二元醇，其中聚烷氧基二元醇的烷氧基含碳为2-4，可以是聚乙二醇、聚丙二醇、聚四氢呋喃二醇、聚丁烯二醇，优选的是聚乙二醇、聚丙二醇及它们的混合二元醇。组分C封闭掉组分A中5～80%的-NCO基团，更合适的比例是15～30%。B和C封闭掉组分A中-NCO总量的合适比例在30～90%。
所述含氮杂环化合物的制备方法如下：
由摩尔比1：1的酸酐与含一个伯胺和一个仲胺或羟基或巯基的化合物在180～230℃下脱水缩合而成，所述缩合后的产物即所述含氮杂环化合物含有一个活泼氢；
所述含一个伯胺和一个仲胺或羟基或巯基的化合物的结构式如下：
其中n=1～5，优选2～4，R1和R2分别为含1～8个碳的烷基，两者或独立，或通过化学键相连形成一个或几个饱和或不饱和的4～8元环，X为N、O或S。
所述酸酐选自邻苯二甲酸酐、四氢苯酐、甲基四氢苯酐、氯代邻苯二甲酸酐、溴代邻苯二甲酸酐、氟代邻苯二甲酸酐、甲基邻苯二甲酸酐、萘酐或2,3萘二羧酸酐等。
所述含氮杂环化合物是3-(2-氨乙基)吲哚、4-(2-氨基乙基)苯甲醇、1H-咪唑-4-乙胺、4-羟基苯乙胺、2-(2-氨基乙基)苯酚、2-甲基吲哚-3-乙胺、N-乙基乙二胺、N-苯基乙二胺、3-(氨基甲基)吡唑、2-(氨基甲基)吗啉、5-(氨基甲基)吲哚、4-(氨基甲基)苄醇、5-氨基甲基吲唑、2-(2-氨基丙基)吡咯、4-(2-氨基丙基)苯酚、1-(2-氨乙基)哌嗪、4-甲基-5-氨基吲哚、5-氨基异吲哚啉、1-氨基-4-羟基蒽醌、4-氨基苯并咪唑、4-氨基-3-巯基吡啶、2-巯基苯并咪唑或2-(2-氨基乙基)苯酚等。
优选地，此类杂环化合物是4-氨基苯并咪唑、3-(2-氨乙基)吲哚、2-(氨基甲基)吗啉、1-(2-氨乙基)哌嗪等。例如，具有如下结构式：
制备组分D的缩聚反应可以采用文献报道的已知方法。优选的工艺是：按照一定的摩尔比投入酸酐和杂环化合物，在180～230℃之间脱水完成反应，最后用一种或几种极性溶剂的混合物兑稀，譬如异丁醇、丙二醇甲醚、环己酮、MIBK、NMP，得到本发明所述的组分D。
组分D的一种可能的结构式是：
苯酐和3-(2-氨乙基)吲哚反应的脱水缩合物2-((3-吲哚)乙基)异吲哚-1,3-二酮：
组分D的另一种可能的结构式是：
苯酐和1-(2-氨乙基)哌嗪反应的脱水缩合物2-((1-哌嗪)乙基)异吲哚-1,3-二酮：
本发明所述的聚氨酯分散剂主要用于涂料和油墨中颜、填料的分散，任何涂料和油墨中使用的颜填料均适用。譬如金属氧化物颜料如二氧化钛、各种颜色的氧化铁、氧化锌，填料如滑石、高岭土、二氧化硅、重晶石，各种有机颜料如苯并咪唑酮类、偶氮类、喹吖啶酮类、苝系、蒽醌类、异吲哚啉系、DPP系等以及碳黑。
由于本发明所述分散剂基于自制锚定端基的特殊结构，因此对偶氮类、异吲哚啉系以及碳黑等高性能有机颜料的分散和稳定尤其有着非常好的效果，克服了以往聚氨酯类分散剂在分散此类颜料时存在的着色力不强，色浆贮存稳定性差的缺点。
附图说明
图1是实施例2的产物的红外光谱图；
图2是实施例2产物的GPC图谱。
具体实施方式
下面，用实施例来进一步说明本发明内容，但本发明的保护范围并不仅限于实施例。对本领域的技术人员在不背离本发明精神和保护范围的情况下做出的其它的变化和修改，仍包括在本发明保护范围之内。
实施例1
组分B的制备：
聚酯一元醇B1(反应物摩尔比为正辛醇：ε-己内酯=1：14.65，Mn=1800)：在氮气保护下，投入正辛醇(7.24份，0.056mol)、ε-己内酯(92.76份，0.814mol)，搅拌下升温至110℃，投入二丁基二月桂酸锡(DBTDL，0.03份，10%的丁醇溶液)，继续升温到170～180℃保温6hr以上至固体分达标，得到常温下为白色常温蜡状固体，羟值32，此为聚酯一元醇B1，数均分子量1800。
聚酯一元醇B2(异辛醇：ε-己内酯：δ-戊内酯=1：8.67：4.94，Mn=1600)：制备工艺同聚酯一元醇B1的制备方法，得到透明液状物，羟值35，数均分子量1600。
聚丙烯酸酯一元醇B3(MMA：巯基乙醇：AIBN=142：7.25：1，Mn=2000)：
预先准备两个滴加釜，分别装有组分A：甲基丙烯酸甲酯(57份，0.569mol)，组分B：2-巯基乙醇(2.33份，0.029mol)，偶氮二异丁腈(0.67份，0.004mol)和醋酸乙酯(20份)的混合物。在氮气保护下，投入醋酸乙酯(20份)，升温至回流温度，开始滴加组分A，半小时后开始滴加组分B，均200分钟滴完，滴加结束后，继续在80℃左右保温至固体分达标，最后升温至120℃抽真空拔出溶剂，得到全固份样品，浅黄色透明，羟值为27.50，数均分子量2000。
聚醚一元醇B4(MPEG2000，Mn=2000)，B4为市售产品，羟值28，常温白色蜡状固体。
聚醚一元醇B5(丁氧基EO:PO=1：1一元醇，Mn=1000)，B5为市售产品，羟值56，常温无色液体。
组分C的制备：二元醇C1(反应物摩尔比为丁二醇：ε-己内酯：δ-戊内酯=1：5.46：0.94，Mn=800)。在氮气保护下，投入1,4-丁二醇(11.20份，0.124mol)，ε-己内酯(77.22份，0.677mol)，δ-戊内酯(11.58份，0.116mol)，搅拌下升温至130℃，投入四丁氧基锆(0.3份，30%的丁醇溶液)，继续升温到175-180℃保温6hr以上至固体分达标，得到轻微蜡状固体，羟值141，数均分子量800。
二元醇C2(反应物摩尔比为PEG200：ε-己内酯=1：10.53，Mn=1400)：工艺同二元醇C1，得到白色常温蜡状固体，羟值40，数均分子量1400。
二元醇C3(PEG800，Mn=800)：C3为市售产品，羟值140，常温白色蜡状固体。
组分D的制备：
锚定端基D1(反应物摩尔比为邻苯二甲酸酐：4-氨基苯并咪唑=1：1)：在氮气保护下，投入邻苯二甲酸酐(52.66份，0.356mol)，4-氨基苯并咪唑(47.34份，0.356mol)，逐步升温至180℃，保温至酸值恒定，继续升温到220～230℃，保温至酸值小于1，降低温度到80℃，用NMP兑稀至50%，得到浅褐色液体，此为锚定端基D1。
锚定端基D2(反应物摩尔比为邻苯二甲酸酐：3-(2-氨乙基)吲哚=1：1)：工艺同锚定端基D1，用3-(2-氨乙基)吲哚替代4-氨基苯并咪唑，得到固体分为50%的浅褐色液体，此为锚定端基D2。EI MS显示，D1的分子量为259.9。
锚定端基D3(反应物摩尔比为邻苯二甲酸酐：1-(2-氨乙基)哌嗪=1：1)：工艺同锚定端基D1，用1-(2-氨乙基)哌嗪替代4-氨基苯并咪唑，得到固体分为50%的浅褐色液体，此为锚定端基D3。
锚定端基D4(反应物摩尔比为2,3-萘二羧酸酐：2-(氨基甲基)吗啉=1：1)：工艺同锚定端基D1，用2-(氨基甲基)吗啉替代4-氨基苯并咪唑，得到固体分为50%的浅褐色液体，此为锚定端基D4。
聚氨酯分散剂的制备
对比例1：在氮气保护下，投入21.63份Desmodur IL(51% 的醋酸丁酯溶液，拜耳公司产品)、24.52份混合溶剂(二甲苯:醋酸丁酯=4：1)、24.33份聚酯一元醇B1和0.1份的DBTDL（10%的醋酸丁酯溶液），升温到70℃，保温至NCO恒定后，投入1.7份二元醇C1，继续保温至NCO恒定后，投入3.09份4-(2-氨乙基)吡啶和24.72份的丙二醇甲醚醋酸酯（MPA）的混合物，60℃保温1小时后出料。得到固体分40%的有一定粘度的浅黄色透明液体，氨值10.2。
对比例2：在氮气保护下，投入12.2份的Desmodur N(75%的醋酸丁酯：二甲苯=1：1溶液，拜耳公司产品)、22.65份混合溶剂(二甲苯:醋酸丁酯=1：1)、28.75份的聚酯一元醇B2和0.1份的DBTDL（10%的醋酸丁酯溶液），升温到70℃，保温至-NCO的量恒定后，投入1.57份的聚乙二醇800(PEG 800)，继续保温至-NCO的量恒定后，投入12.2份的3-苯并咪唑-1-丙酸-2-羟乙酯(50%的NMP溶液，为苯并咪唑与丙烯酸羟乙酯的Michael加成产物，制备方法可参考现有技术中的成熟工艺)和22.65份MPA的混合物，升温到60℃保温1小时后出料。得到固体分45%的浅黄色透明液体，氨值13.2。
实施例2
聚氨酯的分散剂的制备方法同对比例1，不同的是，分别用Desmodur IL(19.02份)、聚酯一元醇B1(23.38份)、二元醇C1(1.55份)、锚定端基D2(11.10份)代替其中的相应组分，得到固体分40%的有一定粘度的浅黄色透明液体，氨值为3.2。图1为产物的红外光谱图，图2为该产物的GPC图谱，其分析结果如下表1所示：
实施例3
聚氨酯分散剂的制备方法同对比例1，不同的是，分别用Desmodur IL(17.81份)、聚酯一元醇B1(23.75份)、PEG 2000(2.23份)、锚定端基D1(10.39份) 代替其中的组分，得到固体分40%的有一定粘度的浅黄色透明液体，氨值为5.8。
实施例4
聚氨酯分散剂的制备方法同对比例1，不同的是，分别用Desmodur IL(19.66份)、聚酯一元醇B2(22.33份)、PEG 2000(2.21份)、锚定端基D3(11.14份)代替其中的组分，得到固体分40%的有一定粘度的浅黄色透明液体，氨值为12.5。
实施例5
聚氨酯分散剂的制备方法同对比例1，不同的是，分别用Desmodur IL(20.78份)、聚丙烯酸酯一元醇B3(21.76份)、PEG 2000 (1.39份)、锚定端基D2(12.12份)代替其中的组分，得到固体分40%的有一定粘度的浅黄色透明液体，氨值为3.5。
实施例6
聚氨酯分散剂的制备方法同对比例2，不同的是，分别用Desmodur N(11.92份)、聚酯一元醇B2(27.74份)、PEG 1000 (1.53份)、锚定端基D3(13.62份)替代其中的组分，得到固体分45%的浅黄色透明液体，氨值为4.8。
实施例7
聚氨酯分散剂的制备方法同对比例2，不同的是，分别用Desmodur N(13.23份)、聚醚一元醇B5(25.21份)、PEG 2000 (3.53份)、锚定端基D1(12.0份)替代其中的组分，得到固体分45%的浅黄色透明液体，氨值13.3。
实施例8
聚氨酯分散剂的制备方法同对比例2，不同的是，分别用Desmodur HL(15.35份，60%的醋酸丁酯溶液，拜耳公司产品)、聚酯一元醇B1(23.37份)、PEG 800 (1.34份)、锚定端基D2(12.02份)和替代其中的组分，得到固体分40%的浅黄色透明液体，氨值3.8。
实施例9
聚氨酯分散剂的制备方法同对比例2，不同的是，分别用Desmodur HL(13.72份)、聚醚一元醇B4(25.03份)、二元醇C2(1.34份)、锚定端基D3(10.37份)替代其中的组分，得到固体分40%的浅黄色透明液体，氨值4.5。
本发明应用测试数据为评估本发明聚氨酯分散剂的分散性能，制备了相应的颜料浆，评价其色浆降黏及贮存稳定性能，并将颜料浆调入到树脂中，评价其展色能力。具体评价过程和测试结果如下所示。
表2是分别含本发明的聚氨酯分散剂与对比分散剂的颜料浆配方，制备工艺如下：在震荡瓶中依次投入分散剂、1：1的二甲苯和丙二醇甲醚醋酸酯混合溶剂、颜料、树脂后搅拌均匀，最后投入一定量的玻璃珠(直径2～3 mm)，放入震荡机中分散2小时后冷却，即得到颜料浆。
表3是表2中颜料浆的粘度以及在50℃中热稳定性测试数据，如下：
* BROOKFIELD RVDV-I数显粘度计
将上述颜料浆Ⅰ～Ⅵ按照羟基丙烯酸树脂：颜料浆：固化剂：混合溶剂的摩尔比为5：3：2.5：1.5的比例，分别制备了色漆Ⅰ～Ⅵ，制备工艺如下：羟基丙烯酸树脂与颜料浆混合后，用高速搅拌机分散（5000rpm*3min），分散完成后，加入溶剂、固化剂并手搅均匀。上述色漆过滤后，将其用60μm绕丝棒刮涂于聚酯片上，室温干燥。检测色漆聚酯片的20度光泽数据如下：
从上述表3和表4的数据可以明显看出，对比基于传统锚定端基的聚氨酯分散剂，本发明的聚氨酯分散剂由于采用了新型的锚定端基，对颜料的吸附能力有了明显提高，因而颜料浆（Ⅱ、Ⅲ、Ⅴ、Ⅵ）的粘度有了明显的降低，颜料浆在50℃中贮存后的热稳定性有了大幅改善。同时由于锚定端基吸附能力的提高，有助于分散剂能够更好的稳定住研磨过程中被解开的颜料颗粒，更好的克服了由于颜料颗粒之间的伦敦范德华力引起的再聚集现象，因而颜料能被分散到更小的粒径。因此基于本发明之聚氨酯分散剂的色漆20度光泽数据更好，颜料着色力体现的更加充分。
Claims (10)
1.一种新型聚氨酯分散剂，其特征在于，所述聚氨酯化合物在合成时由含氮杂环化合物封端，所述含氮杂环化合物由酸酐与含一个伯胺和一个仲胺或羟基或巯基的化合物脱水缩合而成，所述缩合后的产物即所述含氮杂环化合物含有一个活泼氢；
所述含一个伯胺和一个仲胺或羟基或巯基的化合物的结构式如下：
其中n=1～5；R1和R2分别为含1～8个碳的烷基，虚线连接表示两者或独立，或通过化学键相连形成一个或几个饱和或不饱和的4～8元环，X为N、O或S。
2.权利要求1所述的新型聚氨酯分散剂的制备方法，其特征在于，包括如下步骤：首先，在二甲苯和醋酸丁酯的混合溶液中，DBTDL催化作用下，组分A和组分B在70～80℃中反应，用组分B封闭掉1～90%组分A中的-NCO基团；然后，投入组分C，继续在70～80℃下反应，组分C封闭掉5～80%组分A中的-NCO基团，并且，组分B和组分C封闭的组分A的-NCO总量为30～90%；最后，50～60℃下保温1小时，用组分D封闭掉组分A中剩余的-NCO；其中，
组分A为一种或多种含2.0到6.0平均官能度的异氰酸酯多聚体；
组分B为聚醚或聚酯或聚丙烯酸酯的一元羟基化合物；
组分C为两官能度的扩链剂；
组分D为含氮杂环化合物。
3.根据权利要求2所述的制备方法，其特征在于，所述聚酯的一元羟基化合物可以通过小分子一元醇与内酯的开环得到，也可以通过小分子一元醇与二元醇、二元酸、酸酐缩聚而成，还可以通过小分子一元醇与羟基酸缩聚而成，或者是这两种方法的混合。
4.根据权利要求2所述的制备方法，其特征在于，所述两官能度的扩链剂是数均分子量为600～2000的二元醇、二元胺或二元羧酸。
5.根据权利要求3所述的制备方法，其特征在于，所述聚酯的一元羟基化合物的数均分子量为300～5000，所述聚醚的一元羟基化合物的数均分子量为300～6000。
6.根据权利要求5所述的制备方法，其特征在于，所述聚酯的一元羟基化合物
的数均分子量优选为1000～3000，所述聚醚的一元羟基化合物的数均分子量优选为1000～4000。
7.根据权利要求2所述的制备方法，其特征在于，所述聚丙烯酸酯的一元羟基化合物的制备方法如下：
由(甲基)丙烯酸酯单体CH2=C(CH3)C(=O)OR在2-巯基乙醇的调聚作用下，用常规引发剂制备而成，数均分子量为300～20000，优选的是500-10000，其中R是含1～18个碳的烷基。
8.根据权利要求2所述的制备方法，其特征在于，所述含氮杂环化合物的制备方法如下：
由摩尔比为1：1的酸酐与含一个伯胺和一个仲胺或羟基或巯基的化合物在180～230℃下脱水缩合而成，所述缩合后的产物即所述含氮杂环化合物含有一个活泼氢；
所述含一个伯胺和一个仲胺或羟基或巯基的化合物的结构式如下：
其中n=1～5，R1和R2分别为含1～8个碳的烷基，两者或独立，或通过化学键相连形成一个或几个饱和或不饱和的4～8元环，X为N、O或S。
9.根据权利要求8所述的制备方法，其特征在于，所述酸酐选自邻苯二甲酸酐、四氢苯酐、甲基四氢苯酐、氯代邻苯二甲酸酐、溴代邻苯二甲酸酐、氟代邻苯二甲酸酐、甲基邻苯二甲酸酐、萘酐或2,3萘二羧酸酐。
10.根据权利要求8所述的制备方法，其特征在于，所述含氮杂环化合物是3-(2-氨乙基)吲哚、4-(2-氨基乙基)苯甲醇、1H-咪唑-4-乙胺、4-羟基苯乙胺、2-(2-氨基乙基)苯酚、2-甲基吲哚-3-乙胺、N-乙基乙二胺、N-苯基乙二胺、3-(氨基甲基)吡唑、2-(氨基甲基)吗啉、5-(氨基甲基)吲哚、4-(氨基甲基)苄醇、5-氨基甲基吲唑、2-(2-氨基丙基)吡咯、4-(2-氨基丙基)苯酚、1-(2-氨乙基)哌嗪、4-甲基-5-氨基吲哚、5-氨基异吲哚啉、1-氨基-4-羟基蒽醌、4-氨基苯并咪唑、4-氨基-3-巯基吡啶、2-巯基苯并咪唑或2-(2-氨基乙基)苯酚。
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| WO2013155652A1 (zh) * | 2012-04-16 | 2013-10-24 | Wang Zhijun | 一种聚氨酯分散剂及其制备方法 |
| CN106554468A (zh) * | 2015-09-29 | 2017-04-05 | 北京佰禄士科技有限公司 | 一种活性聚氨酯高分子化合物 |
| CN106554468B (zh) * | 2015-09-29 | 2019-11-12 | 常州领景新材料科技有限公司 | 一种活性聚氨酯高分子化合物 |
| CN106084162A (zh) * | 2016-06-17 | 2016-11-09 | 陈鹏 | 一种带酰胺的聚氨酯衍生物的涂料油墨分散剂及其制备方法 |
| CN106084162B (zh) * | 2016-06-17 | 2018-12-18 | 陈鹏 | 一种带酰胺的聚氨酯衍生物的涂料油墨分散剂及其制备方法 |
| CN108586698A (zh) * | 2018-05-14 | 2018-09-28 | 美瑞新材料股份有限公司 | 一种自润滑热塑性聚氨酯弹性体的制备方法 |
| CN108586698B (zh) * | 2018-05-14 | 2020-12-29 | 美瑞新材料股份有限公司 | 一种自润滑热塑性聚氨酯弹性体的制备方法 |
| CN112724349A (zh) * | 2019-10-28 | 2021-04-30 | 立邦涂料（中国）有限公司 | 新型聚合物及其用途 |
| CN112778488A (zh) * | 2020-12-29 | 2021-05-11 | 江南大学 | 一种反应性支化聚氨酯高分子分散剂的制备方法 |
| CN113403001A (zh) * | 2021-06-02 | 2021-09-17 | 深圳市顾康力化工有限公司 | 一种封闭型异氰酸酯潜伏性固化剂及其制备方法和应用 |
| CN115521428A (zh) * | 2022-09-30 | 2022-12-27 | 苏州欧纳克纳米科技有限公司 | 一种tpu用相容剂及其制备方法 |
| CN115521428B (zh) * | 2022-09-30 | 2023-08-25 | 苏州欧纳克纳米科技有限公司 | 一种tpu用相容剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20150065676A1 (en) | 2015-03-05 |
| WO2013155652A1 (zh) | 2013-10-24 |
| EP2839873A1 (en) | 2015-02-25 |
| CN102658057B (zh) | 2014-09-10 |
| KR20150020277A (ko) | 2015-02-25 |
| JP2015520777A (ja) | 2015-07-23 |
| EP2839873B1 (en) | 2017-01-04 |
| US9670305B2 (en) | 2017-06-06 |
| JP5960343B2 (ja) | 2016-08-02 |
| EP2839873A4 (en) | 2016-02-17 |
| KR101644497B1 (ko) | 2016-08-01 |
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