CN101627067A - 聚胺-聚丙烯酸酯分散剂 - Google Patents
聚胺-聚丙烯酸酯分散剂 Download PDFInfo
- Publication number
- CN101627067A CN101627067A CN200880007030A CN200880007030A CN101627067A CN 101627067 A CN101627067 A CN 101627067A CN 200880007030 A CN200880007030 A CN 200880007030A CN 200880007030 A CN200880007030 A CN 200880007030A CN 101627067 A CN101627067 A CN 101627067A
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- Prior art keywords
- polyamine
- grafting
- adulterant
- polyacrylates
- graft copolymers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 8
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
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- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920003264 Maprenal® Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000498779 Myristica Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
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Abstract
本发明涉及基于聚胺－接枝－聚丙烯酸酯掺合物的液体分散剂、其制备及其在溶剂型体系中的用途，具体涉及通式(1)的聚胺－接枝－聚丙烯酸酯接枝聚合掺合物或通式(1)和Y T－(A1，A2)－Y 1的混合物，其中T是聚胺或聚亚胺，A1是选自酰胺或酰亚胺的桥联键，A2是－N－C－桥联键，Y是通式(2)的丙烯酸酯残基，其中R1和R2独立地为氢或C1－20烷基、芳基、杂芳基、取代的芳基。n为1－1000的数，其中聚胺－接枝－聚丙烯酸酯接枝共聚物掺合物的平均分子量为50000g/mol至150000g/mol且多分散性Mw/Mn大于3。
Description
本发明涉及一种基于聚胺-接枝-聚丙烯酸酯掺合物的液体分散剂，其制备及其在溶剂型体系中的用途。
从US 6573313中已知聚乙烯亚胺-聚甲基丙烯酸甲酯，US 6573313描述了通过乳液自由基聚合方法获得的核壳胶乳的制备，其包括在聚胺的氮原子上产生自由基，然后所述自由基能够引发丙烯酸酯的自由基聚合。产品被建议用作基因递送载体。
用作分散剂的接枝共聚物例如为聚胺-接枝-聚酯或聚胺-接枝-聚醚。专利公开WO00/024503、WO04/078333、WO99/049963、WO94/021368涉及一系列基于PAI的分散剂，其中将由羟基羧酸缩聚获得的接枝链用酸基团封端，通过酸基团与胺基团间的中和反应和酰胺化(amidification)反应将所述接枝链接枝至PAI。该接枝链为非极性。分散剂主要用于非极性溶剂型涂料体系。
专利公开WO01/080987、WO98/019784、US9599947、EP0208041和WO99/055763、US6583213要求保护一系列基于PAI的分散剂，其中接枝链由内酯和/或其衍生物的开环聚合获得。接枝链是用酸基团封端的聚酯，其通过羧酸引发的内酯或烷基取代内酯的开环聚合获得，通过酸基团与胺基团间的中和反应和酰胺化反应将所述接枝链接枝至PAI；或者接枝链是用烯键式不饱和基团封端的聚酯，其通过丙烯酸-2-羟基乙酯引发的内酯开环聚合获得，经由迈克尔加成将所述接枝链接枝至PEI主链。
WO05/010109要求保护一种基于PAI的聚醚液体分散剂。接枝链是用一个酸基团封端的聚醚，其通过琥珀酸酐与CH3-(EO)m-(PO)n-NH2的酯化获得。经由中和反应和酰胺化反应将聚醚链接枝至PAI。该分散剂应用于极性有机或水性涂料体系。
通常，所要求保护的PAI-接枝-聚酯和PAI-接枝-聚醚的接枝链具有高Tg和可结晶性，这限制了它们的用途，例如不可低温应用、储存稳定性不佳等。除此以外，这些分散剂全部通过“接枝至”方法制备，即首先合成接枝侧链，然后将其接枝至PAI主链，从而其制造需要至少两个或更多个步骤。
US2002/143081公开了包含核和壳的两亲型纳米颗粒。用于制造该颗粒的方法包括在水性体系中将乙烯属单体接枝聚合至聚乙烯亚胺。接枝共聚物和聚甲基丙烯酸甲酯均聚物的分子量为500000至1000000。聚合的乙烯属单体的多分散性Mw/Mn为1.5至3。核壳颗粒例如用作药物载体。该文献仅提及所述聚合物在皮革修整、油漆纸(paints paper)和纺织工业中的潜在应用。未具体公开作为分散剂的用途。
本发明一方面提供具有良好储存稳定性的液体分散剂，其能够用于溶剂型体系中的低温应用和低粘度应用。
因此，本发明涉及通式1的一种液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物或通式1和Y的混合物，
T-(A1，A2)-Y 1
其中
T是聚胺或聚亚胺，
A1是选自酰胺
或酰亚胺的桥联键，
A2是-N-C-桥联键，
Y是通式2的丙烯酸酯残基，
其中，
R1和R2独立地为氢或C1-20烷基、芳基、杂芳基、取代的芳基，
n为1-1000的数，并且
其中聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的平均分子量为50 000g/mol至150 000g/mol且多分散性Mw/Mn大于3。
定义
本文使用的术语“接枝共聚物”是指通过所谓的“接枝自”方法制备的共聚物。沿着聚胺主链连接丙烯酸酯基团作为侧基。在将侧链接枝至聚胺主链后进行组装。
液体是指未结晶。
术语“聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物”意指目前可通过自由基聚合(A2＝NC)、迈克尔加成(A2＝N-C)和酯交换(A1＝酰胺或酰亚胺)获得多于一种共聚物。
术语“聚胺”是指每分子包含两个或更多个伯胺基或仲胺基的化合物。聚胺选自MW为100g/mol至100,000g/mol，优选500g/mol至50,000g/mol的聚(C2-6-亚烷基亚胺)、聚乙烯胺、聚烯丙基胺或聚(酰胺-胺)树枝状聚合物。
聚(C2-6-亚烷基亚胺)例如聚丙烯-亚胺或聚乙烯亚胺，优选聚乙烯亚胺。
n优选为5至100。聚丙烯酸酯链(n＞1)可由一种丙烯酸酯单体的均聚获得，或者两种或更多种不同丙烯酸酯单体的无规共聚合获得。
R1优选氢或甲基。
R2优选氢或含有1至20个碳原子的直链或支链烷基链。实例为甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正己基、2-羟基乙基、2-甲氧基乙基、2-乙氧基乙基、冰片基、异冰片基、异癸基、月桂基、肉豆寇基、硬脂基、环己基。
芳基优选苯基、萘基。
取代的芳基优选具有甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正己基、氯的取代基的取代的苯基和取代的萘基。
杂芳基优选冰片基、异冰片基、糠基。
根据权利要求1，优选液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物，其中T是聚乙烯亚胺，R1是氢或甲基且R2是C1-20烷基，并且n是5至100。
方法
通过在有机溶剂中在自由基引发剂的存在下将聚胺与丙烯酸酯单体共聚合制备本发明的聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物，其中：
1.聚胺与丙烯酸酯单体的重量比为1∶5至1∶100；
2.自由基引发剂与丙烯酸酯单体的重量比为1∶5至1∶100；
3.于10℃至200℃的温度下在惰性气体气氛下在一个釜中实施该方法，
4.该方法至少包括：丙烯酸酯与聚胺的酯交换反应以获得聚胺酰胺或聚胺酰亚胺；聚胺与丙烯酸酯单体的迈克尔加成反应以获得聚胺丙烯酸酯；以及聚胺与丙烯酸酯单体的接枝聚合以获得聚胺-接枝-聚丙烯酸酯。
本发明还涉及一种可通过根据以上方法的方法获得的液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物。
丙烯酸酯单体可以以CH2＝CR1COOR2表示，其中R1和R2独立地为氢或烷基、芳基、杂芳基、取代的芳基，例如丙烯酸正丁酯、丙烯酸甲酯、甲基丙烯酸甲酯、甲基丙烯酸异丁酯、丙烯酸叔丁酯、甲基丙烯酸正丁酯、丙烯酸-2-羟基乙酯、甲基丙烯酸-2-羟基乙酯、丙烯酸异冰片酯、甲基丙烯酸异冰片酯、甲基丙烯酸缩水甘油酯、丙烯酸缩水甘油酯、丙烯酸环己酯、甲基丙烯酸环己酯等。
自由基引发剂可以选自2，2’-偶氮-二(异丁腈)(AIBN)、过二硫酸钾、2，2’-偶氮双(脒基丙烷)二盐酸盐和烷基氢过氧化物，例如过氧化苯甲酰、过氧化二叔丁基、过氧化氢叔丁基、氢过氧化枯烯、氢过氧化对异丙基枯烯、萜烷过氧化氢或氢过氧化蒎烷等。
优选2，2’-偶氮-二(异丁腈)。
聚胺与丙烯酸酯单体的重量比为1∶5至1∶50。
自由基引发剂与丙烯酸酯单体的重量比为1∶5至1.50。
重量比决定聚丙烯酸酯结构部分的分子量。
反应温度优选为20℃至120℃。
惰性气体优选为氮气。
以下方案是用于制备聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的代表性反应方案。
酯交换反应可以描述如下：
通过以上示出的酯交换方法获得聚胺酰胺。在自由基引发剂的存在下将聚胺酰胺进一步反应生成通式A的聚胺酰胺-聚丙烯酸酯共聚物，其中R1和R2如上定义。
迈克尔加成可以描述如下：
聚胺与丙烯酸脂的不饱和键的亲核加成生成通式B的聚胺丙烯酸脂，其中R1和R2如上定义。
接枝共聚合可以描述如下：
在接枝自方法中使用聚胺作为大分子引发剂以引发自由基聚合。组装丙烯酸酯链获得通式C的聚胺-接枝-聚丙烯酸酯，其中R1和R2如上定义。
自由基聚合生成聚丙烯酸酯Y。
本发明还涉及一种包含以下化合物的掺合物的液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物，
其中R1和R2以及n如上定义，并且其中聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的平均分子量为50 000g/mol至150 000g/mol且多分散性Mw/Mn大于3。
包含(A+B+C+Y)的掺合物是具有低Tg且未结晶的透明琥珀色液体。使用该掺合物作为分散剂用于所有低温应用。该分散剂可溶于从非极性至极性的宽范围多种有机溶剂中。在应用中，分散剂令人惊讶地显示优异的颜料分散效果，特别是由于分散剂与TPA的良好相容性而用于TPA漆料。因此，颜料浓缩物显示低粘度，这意味着颜料装载量高并由此能够实现高生产力。分散剂显示更少絮凝、更少起粒、高光泽度、更好颜色性质、更低颜料浓缩物粘度、更低稳定储存温度等。涂层显示高光泽度和良好的颜色性质，在醇酸、CAB和TPA漆料体系中实现了明显优于现有技术的性能。
分散剂溶液在较低温度下保持稳定(50％溶液，在＜-15℃下稳定至少两周)，这意味着本发明的产品易于使用，并且能够适用于低温应用。
此外，通过调节丙烯酸酯单体的类型、丙烯酸酯单体与聚胺的比率、自由基引发剂与丙烯酸酯单体的比率和反应条件能够容易地调节玻璃化转变温度、可结晶性和分散剂的极性。
起始材料的可达性
不同分子量的聚乙烯亚胺是Nippon Shukubai的商品。
MW为10,000的聚乙烯胺从Mitsubishi Kasei商购。
MW为10,000的聚烯丙基胺从Nitto Boseki商购。
聚丙烯亚胺树枝状聚合物从DSM Fine Chemicals商购，以及聚(酰胺-胺)树枝状聚合物从Aldrich Chemical Company商购。
丙烯酸酯单体、2，2’-偶氮-二(异丁腈)和过氧化氢叔丁基是通用商品。
用途
聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物能够在广阔应用领域中用作分散剂，所述领域例如涂料、墨水、电子材料，尤其是低温和低粘度应用。
本发明的聚胺-接枝-聚丙烯酸酯用于基于溶剂的体系中，例如用于基于溶剂的有机和无机颜料分散体，例如用于醇酸、CAB(乙酸丁酸纤维)、UV(紫外线)和TPA(热塑性丙烯酸酯)漆料体系，用于通常的工业涂料尤其是汽车涂料，以及用于印刷墨和绘图艺术。
实施例
实施例1
于35℃在氮气下将5.0g的PEI SP-200(MW 10,000)、50.0g的BA、6.3g的AIBN和85mL甲苯的混合物搅拌24小时，然后在60℃下搅拌70小时。然后在真空***中除去甲苯。获得黄色液体产物。
实施例2-64
除了如下表1中所详述的改变聚胺、丙烯酸酯单体、自由基引发剂的类型和量以及反应条件以外，全部以与实施例1类似的方式制备实施例2-64。
表1.
实施例的分子量在下表2中列出。
表2.
| 实施例 | Mn | Mw | Mw/Mn |
| 2 | 8,650 | 42,400 | 4.9 |
| 12 | 21,600 | 83,000 | 3.8 |
| 22 | 18,400 | 81,200 | 4.4 |
| 26 | 10,060 | 52,300 | 5.2 |
| 27 | 9,320 | 45,700 | 4.9 |
| 43 | 13,300 | 42,100 | 3.2 |
| 54 | 14,040 | 63,200 | 4.5 |
| 62 | 10,050 | 55,300 | 5.5 |
Mw：重均分子量
Mn：数均分子量
性能筛选
为了测试所获得样品的分散效果，根据配方1制备不含树脂的颜料浓缩物。在玻璃珠的帮助下将研磨料在Scandex振动器中分散1.5h。然后将研磨料过滤并在室温下储存过夜。用于测试的调稀料(配方2)基于烘漆、CAB底漆和TPA底漆。配方3显示用于烘漆、CAB漆料和TPA漆料的漆料配方。在2000rpm下高速搅拌5分钟以混合漆料制剂，并将其应用于膜厚度为35μm-75μm的聚酯膜上。当制备完成后，剩余漆料用乙酸丁酯1∶1稀释用于倾倒测试(pour-out test)。
首先，根据专利例如WO 9421368、USP 6583213和USP 6599947等合成竞争性级别产品。根据配方1、2和3测试这些产品的性能。结果表明竞争性产品A表现优于其它产品，然后将其作为本文中的代表性分散剂。
配方1.颜料浓缩物的制备
| 成分/颜料浓缩物编号 | 1 | 2 | 3 | |
| 1) | 分散剂(100％固体) | 5.35 | 5.40 | 3.62 |
| 2) | 乙酸1-甲氧基-2-丙基酯(MPA) | 19.65 | 26.60 | 31.38 |
| 3) | 颜料白21 | 75.00 | ||
| 4) | 颜料黑7(特黑100) | 18.00 | ||
| 5) | 颜料蓝15:2 | 15.00 | ||
| 6) | 3.0mm玻璃珠 | 100.0 | 100.0 | 100.0 |
| 总计(g) | 200.0 | 150.0 | 150.0 |
配方2.调稀料体系
Vialkyd AC 451：醇酸树脂，UCB
Maprenal MF 650：三聚氰胺树脂，Degussa
CAB-531：从Eastman Chemical商购的乙酸丁酸纤维材料
Uracron CR 226 XB：DSM涂料树脂Uracron CR，OH丙烯酸系
Uramex MF 821：DSM涂料树脂Uramex(氨基)
Paraloid B66：热塑性丙烯酸酯，Rohm Haas
配方3.CAB和烘漆料
| 编码 | 1 | 2 | 3 |
| 调稀料(配方2a或2b) | 9.0 | 7.5 | 7.0 |
| PC白(配方1中第2号) | - | 2.0 | 3.0 |
| PC彩色(配方1中第4-6号) | 1.0 | 0.5 | - |
| 总计/g | 10.0 | 10.0 | 10.0 |
根据配方1、2和3测试表1中实施例1-64的性能。观察到颜料浓缩物流动性良好并且它们的粘度相当于或低于竞争性产品A。用Thermo-Haake RheoStress 600设备在CR模式下测量颜料浓缩物的流变学行为。表3列出了颜料浓缩物的起始粘度(η0)和动态粘度(ηt)。根据粘度曲线，颜料白浓缩物(PW 21)是牛顿流动，而颜料黑浓缩物(特黑-100)是假塑性流动。颜料蓝浓缩物(PB 15:2)是具有触变性的塑性流动，但是在低剪切应力可以容易地流动(T，表3)下。
表3.颜料浓缩物的流变学数据
根据USP6583213的实施例9制备竞争性产品A。
(丙烯酸-2-羟基乙酯-ε-己内酯-，.δ.-戊内酯(1∶8∶8)PEI(13∶1)
对烘漆料、CAB漆料和特别是TPA漆料进行测试，分散剂的性能整体上非常良好，具有令人满意的结果，例如高光泽度(在60°下平均超过80)、无起粒、无刮擦、着色强度良好等(表4)。
表4.TPA漆料体系的分散效果
结果说明：s＝起粒；1＝无起粒，5＝大量起粒
在溶解性测试中，首先将样品溶解于多种溶剂中使其浓度为50％(w/w)，然后分别在25℃和-15℃下保持一个月。很明显本发明的分散剂与竞争性产品相比溶解性改善(表5)。这表明本发明的样品可结晶性更低，并且它们在各种溶剂体系中的相容性优于竞争性产品A。
表5.样品在各种溶剂中的溶解性(50％，w/w)
结果说明：+：溶解性良好，并且溶液澄清；
+-：溶解性中等，并且部分结晶；
-：溶解度差，并且全部结晶。
Claims (6)
1.通式1的液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物或通式1和Y的混合物，
T-(A1，A2)-Y 1
其中
T是聚胺或聚亚胺，
A1是选自酰胺
或酰亚胺
的桥联键，
A2是-N-C-桥联键，
Y是通式2的丙烯酸酯残基，
其中，
R1和R2独立地为氢或C1-20烷基、芳基、杂芳基、取代的芳基，
n为1-1000的数，
其中所述聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的平均分子量为50 000g/mol至150 000g/mol且多分散性Mw/Mn大于3。
2.如权利要求1所述的聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物，其中T是聚乙烯亚胺，R1是氢或甲基且R2是C1-20烷基，并且n为5至100。
3.一种制备权利要求1所定义的聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的方法，其通过在有机溶剂中在自由基引发剂的存在下将聚胺与丙烯酸酯单体共聚合，其中：
1.聚胺与丙烯酸酯单体的重量比为1∶5至1∶100；
2.自由基引发剂与丙烯酸酯单体的重量比为1∶5至1∶100；
3.于10℃至200℃的温度在惰性气体气氛下在一个釜中实施所述方法，
4.所述方法至少包括：所述丙烯酸酯与所述聚胺的酯交换反应以获得聚胺酰胺或聚胺酰亚胺；聚胺与丙烯酸酯单体的迈克尔加成反应以获得聚胺丙烯酸酯；以及聚胺与丙烯酸酯单体的接枝聚合以获得聚胺-接枝-聚丙烯酸酯。
4.通过权利要求3所述的方法获得的液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物。
5.一种液体聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物，其包含以下化合物的掺合物：
其中R1和R2以及n如权利要求1或2所定义，并且其中所述聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物的平均分子量为50 000g/mol至150 000g/mol且多分散性Mw/Mn大于3。
6.权利要求1所述的聚胺-接枝-聚丙烯酸酯接枝共聚物掺合物作为分散剂的用途。
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| PCT/EP2008/052214 WO2008107326A1 (en) | 2007-03-05 | 2008-02-25 | Polyamine-polyacrylate dispersant |
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| EP (1) | EP2115023B1 (zh) |
| JP (1) | JP5602434B2 (zh) |
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| CN110903438A (zh) * | 2019-12-19 | 2020-03-24 | 上海晨光文具股份有限公司 | 一种用于油墨体系的水性分散剂及其制备方法 |
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- 2008-02-25 US US12/528,495 patent/US8344074B2/en active Active
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| CN105517697A (zh) * | 2013-09-06 | 2016-04-20 | 路博润先进材料公司 | 多酸多碱接枝共聚物分散剂 |
| CN105517697B (zh) * | 2013-09-06 | 2017-12-08 | 路博润先进材料公司 | 多酸多碱接枝共聚物分散剂 |
| CN105849211A (zh) * | 2013-11-04 | 2016-08-10 | 路博润先进材料公司 | 具有稠合芳族酰亚胺结合团的丙烯酸分散剂 |
| CN105849211B (zh) * | 2013-11-04 | 2022-01-21 | 路博润先进材料公司 | 具有稠合芳族酰亚胺结合团的丙烯酸分散剂 |
| CN110903438A (zh) * | 2019-12-19 | 2020-03-24 | 上海晨光文具股份有限公司 | 一种用于油墨体系的水性分散剂及其制备方法 |
| CN111704222A (zh) * | 2020-07-27 | 2020-09-25 | 重庆工商大学 | 一种通过预水解强化酯类絮凝剂絮凝能力的方法 |
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| JP5602434B2 (ja) | 2014-10-08 |
| JP2010520342A (ja) | 2010-06-10 |
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| US20100280183A1 (en) | 2010-11-04 |
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