CN101175559B - 分散剂及其组合物 - Google Patents
分散剂及其组合物 Download PDFInfo
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- CN101175559B CN101175559B CN200680016200XA CN200680016200A CN101175559B CN 101175559 B CN101175559 B CN 101175559B CN 200680016200X A CN200680016200X A CN 200680016200XA CN 200680016200 A CN200680016200 A CN 200680016200A CN 101175559 B CN101175559 B CN 101175559B
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- Prior art keywords
- acid
- residue
- anhydride
- group
- composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 58
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 28
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- 150000003839 salts Chemical class 0.000 claims abstract description 18
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
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- 150000008065 acid anhydrides Chemical class 0.000 claims description 17
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 11
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- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 108090000623 proteins and genes Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 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
- 125000001544 thienyl group Chemical group 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
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- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
- LXNOENXQFNYMGT-UHFFFAOYSA-N xi-5-Hydroxydodecanoic acid Chemical compound CCCCCCCC(O)CCCC(O)=O LXNOENXQFNYMGT-UHFFFAOYSA-N 0.000 description 1
- 229940032912 zephiran Drugs 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
-
- 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
-
- 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
-
- 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
- C09D11/10—Printing inks based on artificial resins
-
- 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
-
- 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
- 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
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
Abstract
本发明提供了式(1):E-O-(Y)x-T-NR′-A-Z-W0-v的分散剂及其盐,其中E是R或R-NR′-T-;R是H或C1-50-任选取代烃基;R′是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基,或C1-8-任选取代烃基;Y是C2-4-亚烷氧基;T是C2-4亚烷基;A是二元酸或其酐的残基;Z是聚胺和/或聚亚胺的残基;W是氧化物、脲或二元酸或其酐的残基;x为2至90;且v代表整数变量。本发明进一步提供了包含微粒固体、有机介质和/或水和分散剂的组合物。
Description
交叉引用
本申请要求2005年5月12日提交的临时申请系列号No.60/680,347的优先权。
技术领域
本发明涉及新型分散剂;和包含所述分散剂、微粒固体和有机介质的组合物。本发明进一步涉及分散剂在油墨、磨料(millbases)、塑料和漆料之类的介质中的应用。
背景技术
油墨、漆料、磨料和塑料之类的许多制剂需要有效的分散剂以使微粒固体均匀分布在有机介质中。有机介质可以从极性到非极性有机介质不等。含有末端碱性基,例如聚(低碳亚烷基)亚胺链的分散剂是公知的并通常通过聚亚胺与含有末端酸基的聚酯链的反应制备,该反应产生酰胺和盐形式的混合物。
美国专利4,224,212公开了包含由具有至少8个碳原子的羟基羧酸与聚(低碳亚烷基)亚胺反应生成的聚酯的分散剂。该分散剂在非极性介质,例如脂族溶剂和塑料中是有效的。但是,该分散剂在极性介质中具有有限的性能。
欧洲专利申请EP 208041 A公开了含有由ε-己内酯与聚(低碳亚烷基)亚胺反应生成的聚酯的分散剂。该分散剂在更极性的介质,例如酮和酯中特别有效。但是,该分散剂在非极性介质中具有有限的性能。
美国专利4,865,621公开了包含二元酸酐、聚氧化烯单胺和数均分子量最多为1343的烃基多胺的反应产物的发动机燃料组合物。
但是,美国专利申请60/637937和PCT申请WO 05/010109A公开了在极性和非极性有机介质中具有可接受的性能的分散剂。但是,该分散剂具有在降低的色度(有色漆料稀释到白色底漆中)中的差的抗 絮凝性和/或在介质例如磨料和漆料中的储存稳定性。
因此,分散剂在极性和非极性有机介质中都具有可接受的性能且所述分散剂具有可接受的抗絮凝性和/或储存稳定性是有利的。
发明内容
已经发现,某些分散剂表现出优异的在多种有机介质,特别是极性有机介质并包括水中分散微粒固体的能力。
因此,根据本发明,提供了包含式(1)的化合物及其盐的分散剂:
E-O-(Y)x-T-NR′-A-Z-W0-v
式(1)
其中
E是R或R-NR′-T-;
R是H或C1-50-任选取代烃基;
R′是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基,或C1-8-任选取代烃基;
Y是C2-4-亚烷氧基;
T是C2-4亚烷基;
A是二元酸或其酐的残基;
Z是聚胺和/或聚亚胺的残基;
W是氧化物、脲或二元酸或其酐的残基;
x为2至90;且
(0-v)是指0至v的值,其中v代表Z中不带基团E-O-(Y)x-T-NR′-A-的氨基和/或亚氨基的最大可得数量。
在一个实施方案中,本发明进一步提供包含微粒固体、有机介质和/或水和式(1)的化合物及其盐的组合物。
发明详述
本发明提供了如上定义的分散剂和/或组合物。
在一个实施方案中,基团E-O-(Y)x-T-NR′-A-包括基团R-O-(Y)x-T-NR′-A-、R-NR′-T-O-(Y)x-T-NR′-A-、或其混合物。
由于Z是聚胺和/或聚亚胺的残基,在一个实施方案中可能有2 个或2个以上E-O-(Y)x-T-NR′-A-基团连接到Z上,且这些可以相同或不同。
在一个实施方案中,聚氧化烯残基源自二胺,提供了分散剂和/或包含微粒固体、有机介质和式(1a)的化合物的组合物:
R-NR′-T-O-(Y)x-T-NR′-A-Z-W0-v
式(1a)
其中
R是C1-50-任选取代烃基;或R是R”C=O(酰基,其中R”是烷基或芳基);或是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基;
R′是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基,或C1-8-任选取代烃基;或环氧化物的残基;
Y是C2-4-亚烷氧基;
T是C2-4亚烷基;
A是二元酸或其酐的残基;
Z是聚胺和/或聚亚胺的残基;
W是氧化物、脲或二元酸或其酐的残基;
x为2至90;且
v代表Z中不含基团R-NR′-T-O-(Y)x-T-NR′-A-的氨基和/或亚氨基的最大可得数量。
在一个实施方案中,聚氧化烯残基源自单胺,提供了分散剂和/或包含微粒固体、有机介质和式(1b)的化合物的组合物:
R-O-(Y)x-T-NR′-A-Z-W0-v
式(1b)
其中
R是H或C1-50-任选取代烃基,或R是R”C=O(酰基,其中R”是烷基或芳基);或任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基;
R′是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基, 或环氧化物的残基,或C1-8-任选取代烃基;
Y是C2-4-亚烷氧基;
T是C2-4亚烷基;
A是二元酸或其酐的残基;
Z是聚胺和/或聚亚胺的残基;
W是氧化物、脲或二元酸或其酐的残基;
x为2至90;且
v代表Z中不含基团R-O-(Y)x-T-NR′-A-的氨基和/或亚氨基的最大可得数量。
在一个实施方案中,R是烃基,包括芳基、芳烷基、烷芳基、环烷基或烷基,它们可以是直链或支链的,或其混合物。在一个实施方案中,R是包括萘基或苯基的芳基。在一个实施方案中,R是包括2-苯乙基或苄基的芳烷基。在一个实施方案中,R是包括辛基苯基或壬基苯基的烷芳基。在一个实施方案中,R是环烷基,包括C3-8-环烷基,例如环丙基或环己基。
R可以是任选支化的烷基,例如C1-36或C1-30任选支化的烷基。基团RO-由此可以是甲醇、乙醇、正丙醇、正丁醇、正己醇、正辛醇、正癸醇、正十二醇、正十四醇、正十六醇、正十八醇、异丙醇、异丁醇、叔丁醇、2-乙基丁醇、2-乙基己醇、3-庚醇、3,5,5-三甲基己醇、3,7-二甲基辛醇和所谓的Guerbet醇之类的醇的残基。Guerbet醇可以以商品名IsofolTM(购自Condea GmbH)购得,包括其混合物。Guerbet醇的具体例子是IsofolTM 12、14T、16、18T、18E、20、24、28、32、32T和36。
在一个实施方案中,R是C1-6-烷基,在另一实施方案中,R是C1-4-烷基,例如甲基。当R是取代烃基时,取代基可以是C1-10-烷氧基、羰基、磺酰基、氨甲酰基、氨磺酰基、卤素、腈、脲基、氨基甲酸酯或酯(即-COO-或-OCO-)。通常R是未取代的。
基团R′包括(甲基)丙烯酸酯、(甲基)丙烯酰胺的残基或其混合物。这种类型的化合物可以购得。具体例子包括(甲基)丙烯酸烷基酯,例 如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸丁酯、丙烯酸己酯、丙烯酸异辛酯、丙烯酸月桂酯、丙烯酸甲氧基乙酯、丙烯酸苯氧基乙酯、丙烯酸十八烷基酯、任选季铵化的丙烯酸二甲基氨基乙酯、任选季铵化的丙烯酸二乙基氨基乙酯、丙烯酸羟乙酯、丙烯酸羟丙酯或其混合物。季铵化抗衡离子包括卤素离子、氢氧根、烷基硫酸根,例如甲基硫酸根,或其混合物。在一个实施方案中,上述丙烯酸酯的甲基丙烯酸酯对等物也是可用的。
当R是环氧化物的残基时,R可以与上文定义的R或与R′相同。
同样,基团R′也可以是诸如环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯或其混合物之类的环氧化物的残基。同样,基团R′也可以是由卤代烷、卤代芳烷(例如苄基氯)制成的C1-8烃基。在一个实施方案中,R′是任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或C1-8-任选取代烃基。在一个实施方案中,R′不是环氧化物的残基。在一个实施方案中,如前文中对R所公开的那样,R″含有不超过30个碳原子。
在一个实施方案中,R”可以是直链或支链的、饱和或不饱和的任选取代羧酸,例如甲氧基乙酸、丙酸、丁酸、己酸、辛酸、月桂酸、十二烷酸、硬脂酸、2-乙基丁酸、2-乙基己酸、2-丁基辛酸、2-己基癸酸、2-辛基癸酸和2-癸基十四烷酸的残基。这种类型的支链烷基羧酸也可以以商品名IsocarbTM(购自Condea GmbH)购得,具体例子是IsocarbTM 12、16、20、28、32、34T和36。
当R”被取代时,取代基可以是-个或更多醚基团或两个或更多醚基团。因此,R”-CO-可以是AkypoTM羧酸(购自Kao Chem GmbH)的残基。具体例子是AkypoTM LF1、AkypoTM LF2、AkypoTM RLM 25、Akypo TM RLM 45 CA、AkypoTM RO 20 VG和Akypo TM RO 50VG。
当Y是C3-4-亚烷氧基且(Y)x所示的链含有亚乙氧基(-CH2CH2O-)时,(Y)x的结构可以是无规或嵌段的。在一个实施方案中,(Y)x的结构为嵌段。在一个实施方案中,Y上的亚乙氧基单元的数量为0。各个Y可以是-CH2CH2CH2CH2O-、-CH2CH(CH3)O-或-CH2-CH(CH2-CH3)-O-。
在一个实施方案中,式(1和/或1a)的化合物可以是,Y为-CH3CH(CH3)O-基团,且该链可以表示为含有至多75%亚乙氧重复单元的(Y)x。T包括C3-4-亚烷基且在一个实施方案中是-CH2CH(CH3)-。当Y是-CH2CH(CH3)O-时,T也可以是-CH2CH(CH3)-。在数个实施方案中T可以是C3-4-亚烷基、或-CH2CH(CH3)-或-CH2CH2CH2-。
基团R-O-(Y)x-T-NR′-可以包括聚环氧烷单烷基醚单胺的残基或其混合物。这种类型的化合物可以作为JeffamineTM M系列单胺购自Huntsman Corporation。JeffamineTM胺的具体例子是M-600(9,0,600)、M-1000(3,18,1000)、M-2005(32,2,2000)和M-2070(10,31,2000)。括号中的数字分别是环氧丙烷、环氧乙烷的大致重复单元数和数均分子量。
基团RNR′-T-O-(Y)X-T-NR′-可以是聚环氧烷二胺或其混合物的残基。这种类型的化合物可以作为JeffamineTM D或ED系列的二胺购自Huntsman Corporation。JeffamineTM二胺的具体例子是D-230(3,0,230)、D-400(6,0,400)、D-2000(33,0,2000)、D-4000(68,0,4000)、ED-600(3.6,9,600)、ED-900(2.5,15.5,900)和ED2003(6,39,2000)。括号中的数字分别是环氧丙烷、环氧乙烷的大致重复单元数和数均分子量。
当Z是聚胺的残基时,聚胺的例子包括聚乙烯胺、亚烷基多胺(通常由二氯乙烷和乙二胺和/或氨制成)或聚烯丙胺。可以从NittoBoseki购得不同分子量的聚烯丙胺和聚(N-烷基)烯丙胺。可以从Mitsubishi Kasei购得不同分子量的聚乙烯胺。
当Z是聚亚胺或其混合物的残基时,聚亚胺可以是聚(C2-6-亚烷基亚胺)。具体例子包括聚乙烯亚胺(PEI)。聚亚胺可以是线型或尤其是支化的。线型聚乙烯亚胺可以如Takeo Saegusa等人,在Macromolecules,1972,第5卷,第4470页中所述通过聚(N-酰基)烯化亚胺的水解制备。可以从BASF和Nippon Shokubai购得不同分子量的支化聚乙烯亚胺。聚丙烯亚胺树枝状聚合物可购自DSM FineChemicals,聚(酰氨基胺)树枝状聚合物可作为“Starburst”树枝状 聚合物购自Aldrich Chemical Company。
聚胺混合物的其它可用的类型是由上述聚胺混合物的汽提生成的那些,从而作为残余物留下通常被称作“聚胺残渣(polyaminebottoms)”的物质。一般而言,亚烷基多胺残渣可以以少于2重量%,通常少于1重量%的材料在低于大约200℃下沸腾为特征。获自DowChemical Company of Freeport,Texas的名为“E-100”的这类亚乙基多胺残渣的典型样品在15.6℃下具有1.0168的比重,33.15重量%的氮,和在40℃下121厘沲的粘度。这种样品的气相色谱分析含有大约0.93%“轻馏分”(最可能是DETA)、0.72%TETA、21.74%四亚乙基五胺和76.61%五亚乙基六胺和更高(按重量计算)。这些亚烷基多胺残渣包括环状缩合产物,例如哌嗪和二亚乙基三胺或三亚乙基四胺的更高级类似物。
在一个实施方案中,聚胺或聚亚胺的数均分子量为300至650,000;500至600,000;600至100,000;或1200至70,000。在聚乙烯亚胺的情况下,在一个实施方案中,数均分子量不小于600,不小于1200,或不小于1800。
A所代表的二元酸的残基可以源自式HOOC-B-COOH的任何二元酸或其酐,其中B是直接键或含有1至20个碳原子的二价有机部分。B可以是任选被取代的芳族、杂芳族、脂环族或脂族。当B是含有2个或更多碳原子的脂族时,其可以是直链或支链的,饱和或不饱和的。在一个实施方案中,B是未取代的。在数个实施方案中,B含有不超过12个,或不超过8个碳原子。
当B是芳族时,其包括亚苯基;当B是脂环族时,其包括亚环己基,当B是脂族时,其包括亚烷基。合适的二元酸或更高级酸的例子包括对苯二甲酸、四氢邻苯二甲酸、甲基四氢邻苯二甲酸、六氢邻苯二甲酸、甲基六氢邻苯二甲酸、偏苯三酸、C1-20-烯基或烷基丁二酸,尤其是马来酸、丙二酸、丁二酸和邻苯二甲酸。
在一个实施方案中,对于A和/或W,合适的二元酸可以选自马来酸、丙二酸、丁二酸、邻苯二甲酸、马来酸酐、戊二酸酐、丁二酸酐 和邻苯二甲酸酐。在数个实施方案中,合适的酐包括戊二酸酐、丁二酸酐、邻苯二甲酸酐,或其混合物。
可以使用二元酸或其酐的混合物。因此,A可以是一种或一种以上的不同二元酸或酐的残基。但是,在一个实施方案中,A是单种二元酸或酐的残基。类似地,W可以是一种或一种以上的不同二元酸或酐的残基。在一个实施方案中,W是单种二元酸或酐的残基。在一个实施方案中,A和W都是相同二元酸或酐的残基。在一个实施方案中,A和W都是不同二元酸或酐的残基。在一个实施方案中,A和/或W是丁二酸酐的残基。
当W是氧化物的残基时,Z中不带基团E-O-(Y)x-T-NR′-A-的任何氨基或亚氨基可以通过与氧(包括空气)或过氧化物,例如过氧化氢或过硫酸铵的反应转化成N-氧化物。在一个实施方案中,式1的化合物可以用氧化剂(见上文)后处理以将部分和/或所有氨基转化成N-氧化物。
类似地,当W是脲的残基时,Z中与脲反应的游离氨基和/或亚氨基的数量可以在宽限度内变化,直至达到不带基团E-O-(Y)x-T-NR′-A-的氨基或亚氨基的最大数量。
在一个实施方案中,W是二元酸或酐的残基,且Z中大部分(至少50%,或至少75%,或至少90%至99%)不带基团E-O-(Y)x-T-NR′-A-的游离氨基或亚氨基与W所代表的二元酸或酐反应。
在一个实施方案中,Z所代表的聚胺或聚亚胺带有2个或更多基团E-O-(Y)x-T-NR′-A-。这些基团可以相同或不同。这种类型的分散剂可以方便地表示成式(2):
式(2)
其中
X-*-*-X代表聚胺和/或聚亚胺;
Q是链E-O-(Y)x-T-NR′-A-;且
q为2至2000。
在一个实施方案中,Z所代表的聚胺或聚亚胺带有两个或更多不同的聚合物链并表示为式2a:
式2a
其中
X-*-*-X和Q如上定义;且
Q1代表式R1-G-(M)m-的聚酯和/或聚酰胺链;
R1是氢或C1-50-任选取代烃基;
G是二价键或羰基;
M是一种或多种氨基羧酸、一种或多种羟基羧酸、一种或多种羟基羧酸内酯、或其混合物的残基;
q和s是大于0的正整数,在一个实施方案中q+s为2至2000;且
m是2至100的正整数。在一个实施方案中,q与s的比率为6∶1至1∶6。
在一个实施方案中,G是羰基且R1-G-是C1-50-任选取代烃基羧酸,尤其是C1-50-任选取代脂族酸的残基,其中脂族基团可以是饱和或不饱和的,直链或支链的。
在一个实施方案中,如之前对R所公开的那样,R1含有不超过30个碳原子。R1-CO-也可以是直链或支链的,饱和或不饱和的任选取代羧酸,例如甲氧基乙酸、丙酸、丁酸、己酸、辛酸、月桂酸、十二烷酸、硬脂酸、2-乙基丁酸、2-乙基己酸、2-丁基辛酸、2-己基癸酸、2-辛基癸酸和2-癸基十四烷酸的残基。这种类型的支链烷基羧酸也可以以商品名IsocarbTM(购自Condea GmbH)购得,具体例子是IsocarbTM 12、16、20、28、32、34T和36。
当R1被取代时,取代基可以是一个或更多醚基团或两个或更多醚基团。因此,R1-CO-可以是AkypoTM羧酸(购自Kao Chem GmbH)的残 基。具体例子是AkypoTM LF1、AkypoTM LF2、AkypoTM RLM 25、AkypoTM RLM45 CA、AkypoTM RO 20VG和AkypoTM RO 50VG。
可产生M的氨基羧酸包括氨基-C2-20-亚烷(烯)基羧酸或氨基C1-20-亚烷基羧酸。在一个实施方案中,亚烷(烯)基含有不超过12个碳原子。具体例子是11-氨基十一烷酸、6-氨基己酸、4-氨基丁酸、β-丙氨酸或肌氨酸。
可产生M的羟基羧酸包括羟基-C2-20-亚烯基羧酸或羟基-C1-20-亚烷基羧酸。合适的羟基羧酸的具体例子是蓖麻油酸、12-羟基硬脂酸、6-羟基己酸、5-羟基戊酸、12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸、4-羟基癸酸、10-羟基十一烷酸、乳酸或羟基乙酸。
M也可以衍生自内酯,例如β-丙内酯,任选C1-6烷基取代的ε-己内酯和任选C1-6烷基取代的δ-戊内酯。ε-己内酯和/或δ-戊内酯的取代基的具体例子包括7-甲基-、3-甲基-、5-甲基-、6-甲基-、4-甲基-、5-四丁基-、4,4,6-三甲基-和4,6,6-三甲基。
如上所述,分散剂可以以盐形式存在。当分散剂含有羧酸基团时,盐可以是碱金属,例如锂、钾或钠的盐。或者,该盐可以用氨、胺或季铵阳离子形成。胺的例子是甲胺、二乙胺、乙醇胺、二乙醇胺、己胺、2-乙基己胺和十八烷基胺。季铵阳离子可以是季铵阳离子或苄烷铵阳离子。在一个实施方案中,季铵阳离子含有一个或两个含6至20个碳原子的烷基。季铵阳离子的例子是四乙基铵、N-十八烷基-N,N,N-三甲基铵、N,N-双十二烷基N,N-二甲基铵、N-苄基-N,N,N-三甲基铵和N-苄基-N-十八烷基-N,N-二甲基铵阳离子。
在一个实施方案中,含有羧酸基团的分散剂是游离酸形式。
式1的分散剂(其中v是0)可以是有色酸的盐形式。有色酸可以是任何阴离子型染料,例如每分子平均含有0.5至3个磺酸基的磺化或羧化铜或镍酞菁,或含有磺酸和/或羧酸基的双偶氮染料。
当v是0时,Z中的一些不带基团E-O-(Y)x-T-NR′-A-的胺/亚胺基团可以通过与酸或季铵化试剂反应来转化成取代铵基。为此合适的试剂包括无机强酸,例如盐酸、乙酸、硫酸、烷基磺酸、硫酸氢烷基 酯盐、或芳基磺酸。季铵化试剂包括硫酸二甲酯、苄基氯、氯甲烷、溴甲烷、碘甲烷、和丙烷(或丁烷)磺内酯之类的化合物。
式(1)的化合物可以通过本领域已知的任何方法制造。在与聚胺和/或聚亚胺反应之前可以通过美国专利4,713,487和EP 73545中所述的方法制备式(1)的前体。与聚胺和/或聚亚胺的反应在一个实施方案中在100℃至200℃进行。在这些条件下,反应产生酰胺和盐形式的混合物,而非只有盐形式。
涉及二元酸或其酐的反应通常在对反应物为惰性的有机稀释剂存在下进行。在一个实施方案中,有机稀释剂是反应物的溶剂。有机稀释剂可以是芳族或脂族的,包括卤化衍生物。例子是甲苯、氯苯、庚烷和石油醚馏出物。通常,反应在不存在有机稀释剂的情况下进行。
当W是氧化物的残基时,Z中不带基团E-O-(Y)x-T-NR′-A-的氨基和/或亚胺基团的数量可以在宽限度内变化。通过使含有游离氨基和/或亚氨基的分散剂与氧化性化合物,例如氧(或空气)或过氧化物,例如过氧化氢或过硫酸铵反应,容易地制备这类分散剂。类似地,当W是脲的残基时,通过使Z中不带基团E-O-(Y)x-T-NR′-A-的任何游离氨基和/或亚氨基与脲反应,也可以容易地制备这类分散剂。在一个实施方案中,反应在惰性气氛中在80℃至140℃之间进行。
在W是二元酸或其酐的残基的具体情况下,Z中大部分不带基团E-O-(Y)x-T-NR′-A-的氨基和/或亚氨基与该二元酸或酐反应。
该组合物中存在的微粒固体可以是在有机介质中基本不溶的任何无机或有机固体材料。在一个实施方案中,微粒固体是颜料。
合适的固体的例子是用于溶剂油墨的颜料;用于漆料和塑料的颜料、增量剂和填料;分散染料;用于溶剂染料浴、油墨和其它溶剂应用系统的光学增亮剂和织物助剂;用于油基和反相乳液钻探泥浆的固体;干洗流体中的污垢和固体粒子;微粒陶瓷材料;磁性材料和磁记录介质;用于复合材料的纤维,例如玻璃、钢、碳和硼,和作为在有机介质中的分散体施用的杀微生物剂、农业化学品和药品。
在一个实施方案中,固体是来自如Colour Index第三版(1971) 和随后的再版及其附录中的名为“颜料”的章节中所述的任何公认颜料类型的有机颜料。有机颜料的例子是来自偶氮、双偶氮、缩合偶氮、硫靛、阴丹酮、异阴丹酮、二苯并[cd,jk]芘-5,10-二酮、蒽醌、异二苯并蒽醌、三吩二嗪(triphendioxazine)、喹吖啶酮和酞菁系列,尤其是铜酞菁及其核卤化衍生物,以及酸性、碱性和煤染料的色淀的那些。炭黑,尽管严格说来是无机的,在其分散性能方面表现得更像有机颜料。在一个实施方案中,有机颜料是酞菁,尤其是铜酞菁、单偶氮、双偶氮、阴丹酮、anthranthrones、喹吖啶酮和炭黑。
无机固体包括:增量剂和填料,例如滑石、高岭土、二氧化硅、重晶石和白垩;微粒陶瓷材料,例如氧化铝、二氧化硅、氧化锆、二氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合硅-铝氮化物、和金属钛酸盐;微粒磁性材料,例如过渡金属,尤其是铁和铬的磁性氧化物,例如γ-Fe2O3、Fe3O4和掺钴氧化铁、氧化钙、铁氧体,尤其是钡铁氧体;和金属粒子,尤其是金属铁、镍、钴、铜及其合金。
其它可用的固体材料包括农业化学品,例如杀真菌剂、flutriafen、多菌灵、百菌清和代森锰锌。
本发明的组合物中存在的有机介质在一个实施方案中是塑料,在另一实施方案中是有机液体。有机液体可以是非极性或极性有机液体。与有机液体结合的术语“极性”是指如Crowley等人的名为“A ThreeDimensional Approach to Solubility”的文章,在Journal of PaintTechnology,卷38,1996,第269页中所述,有机液体能够形成中等至强的键。这类有机液体通常具有如上述文章中所定义的5或更大的氢键数。
合适的极性有机液体的例子是胺、醚,尤其是低碳烷基醚、有机酸、酯、酮、二醇、醇和酰胺。在Ibert Mellan的名为“Compatibilityand Solubility”的书(1968年Noyes Development Corporation出版)第39-40页上的表2.14中给出了这类中等强度的氢键合液体的许多具体例子,这些液体都落在本文所用的术语“极性有机液体”的范围内。
在一个实施方案中,极性有机液体是二烷基酮、链烷羧酸的烷基酯和链烷醇,尤其是含有最多(包括)总共6个碳原子的这类液体。极性有机液体的例子包括二烷基和环烷基酮,例如丙酮、甲乙酮、二乙酮、二异丙酮、甲基异丁基酮、二异丁基酮、甲基异戊基酮、甲基正戊基酮和环己酮;烷基酯,例如乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、甲酸乙酯、丙酸甲酯、丙基乙酸甲氧酯和丁酸乙酯;二醇和二醇酯和醚,例如乙二醇、2-乙氧基乙醇、3-甲氧基丙基丙醇、3-乙氧基丙基丙醇、乙酸2-丁氧基乙酯、乙酸3-甲氧基丙酯、乙酸3-乙氧基丙酯和乙酸2-乙氧基乙酯;链烷醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇和异丁醇,和二烷基和环醚,例如二乙醚和四氢呋喃。在一个实施方案中,溶剂是链烷醇、链烷羧酸和链烷羧酸酯。在一个实施方案中,本发明适用于在水性介质中基本不溶的有机液体。此外,本领域技术人员会认识到,在有机液体中可以存在少量水性介质(例如二醇、二醇醚、二醇酯和醇),只要整个有机液体在水性介质中基本不溶。
可以用作极性有机液体的有机液体的例子是成膜树脂,例如适用于制备在漆料和油墨之类的各种应用中使用的油墨、漆料和芯片的那些。这类树脂的例子包括聚酰胺,例如VersamidTM和WolfamidTM,和纤维素醚,例如乙基纤维素和乙基羟乙基纤维素、硝基纤维素和乙酸丁酸纤维素树脂,包括其混合物。漆料树脂的例子包括短油醇酸/三聚氰胺-甲醛、聚酯/三聚氰胺-甲醛、热固性丙烯酸/三聚氰胺-甲醛、长油醇酸、聚醚多元醇、和多介质树脂,例如丙烯酸和脲/醛。
有机液体可以是多元醇,也就是具有两个或更多羟基的有机液体。在一个实施方案中,多元醇包括α-Ω二醇或α-Ω二醇乙氧基化物。
在一个实施方案中,非极性有机液体是含脂族基团、芳族基团或其混合物的化合物。非极性有机液体包括非卤化芳烃(例如甲苯和二甲苯)、卤化芳烃(例如氯苯、二氯苯、氯甲苯)、非卤化脂族烃(例如完全和部分饱和的含有6或更多碳原子的直链和支链脂族烃)、卤化脂族烃(例如二氯甲烷、四氯化碳、氯仿、三氯乙烷)和天然非极 性有机物(例如植物油、葵花油、亚麻籽油、萜烯和甘油酯)。
在一个实施方案中,有机液体包含总有机液体的至少0.1重量%,或1重量%或更多的极性有机液体。有机液体任选进一步包含水。在一个实施方案中,有机液体无水。
当有机液体含有水时,存在的量在数个实施方案中不超过有机液体量的70重量%,或不超过50重量%,或不超过40重量%。
塑料可以是热固性树脂或热塑性树脂。本发明中可用的热固性树脂包括在加热、催化、或经受紫外线辐射时产生化学反应并变得相对不熔的树脂。热固性树脂中的典型反应包括氧化或不饱和双键、涉及环氧基/胺、环氧基/羰基、环氧基/羟基、多异氰酸酯/羟基、氨基树脂/羟基部分的反应、自由基反应或聚丙烯酸酯、阳离子聚合或环氧树脂和乙烯基醚、缩合或硅烷醇。
在热固性体系中广泛使用具有羟基官能的聚合物(通常为多元醇)与氨基树脂或多异氰酸酯交联。多元醇包括丙烯酸多元醇、醇酸多元醇、聚酯多元醇、聚醚多元醇和聚氨酯多元醇。典型的氨基树脂包括三聚氰胺甲醛树脂、苯并胍胺甲醛树脂、脲醛树脂和甘脲甲醛树脂。多异氰酸酯是具有两个或更多异氰酸酯基团的树脂,包括单体型脂族二异氰酸酯、单体型芳族二异氰酸酯及其聚合物。典型的脂族二异氰酸酯包括1,6-亚己基二异氰酸酯、异佛尔酮二异氰酸酯和氢化二苯甲烷二异氰酸酯。典型的芳族二异氰酸酯包括甲苯二异氰酸酯和联苯甲烷二异氰酸酯。
在一个实施方案中,热塑性树脂包括聚烯烃、聚酯、聚酰胺、聚碳酸酯、聚氨酯、聚苯乙烯类、聚(甲基)丙烯酸酯、纤维素和纤维素衍生物。所述组合物可以以许多方式制备,但熔体混合和干固体掺合是典型方法。
如果需要,该组合物可以含有其它成分,例如树脂(在这些还没有构成有机介质的情况下)、连接料、流化剂、抗沉降剂、增塑剂、表面活性剂、防沫剂、流变改性剂、匀平剂、光泽改进剂和防腐剂。
该组合物通常含有1至95重量%的微粒固体,确切量取决于固体 性质,量取决于固体性质和固体与极性有机液体的相对密度。例如,固体是有机材料,例如有机颜料时的组合物在一个实施方案中含有15至60重量%固体,而固体是无机材料,例如无机颜料、填料或增量剂时的组合物在一个实施方案中含有组合物总重量的40至90重量%的固体。
该组合物可以通过已知用于制备分散体的任何传统方法制备。因此,固体、有机介质和分散剂可以以任意顺序混合,随后例如通过球磨、珠磨、卵石研磨或塑炼(plasticmilling)对该混合物进行机械处理以将固体粒子降至适当的尺寸,直至形成分散体。或者,固体可以独立地或与有机介质或分散剂混合地处理以降低其粒度,随后添加其它成分并搅拌该混合物以提供组合物。
本发明的组合物特别适用于液体分散体。在一个实施方案中,这类分散体组合物包含:
(a)0.5至30份微粒固体;
(b)0.5至30份式(1)的化合物;和
(c)40至99份有机液体和/或水;其中所有份数均按重量计且量(a)+(b)+(c)=100。
在一个实施方案中,组分a)包含0.5至30份颜料,这类分散体可用作(液体)油墨、漆料和磨料。
如果需要干形式的包含微粒固体和式(1)的分散剂的组合物,则有机液体通常是挥发性的,从而容易通过简单分离方式,例如蒸发从微粒固体中去除。在一个实施方案中,该组合物包含有机液体。
如果干组合物基本上由式(1)的分散剂和微粒固体构成,则其通常含有微粒固体重量的至少0.2%,至少0.5%或至少1.0%的式(1)的分散剂。在一个实施方案中,干组合物含有微粒固体重量的不超过100%,不超过50%,不超过20%,或不超过10%的式(1)的分散剂。
如上所公开,本发明的组合物适用于制备磨料,其中将微粒固体在有机液体中在式(1)的化合物及其盐存在下研磨。
因此,根据本发明的再一方面,提供了包含微粒固体、有机液体 和式(1)的化合物及其盐的磨料。
通常,磨料含有磨料总重量的20至70重量%的微粒固体。在一个实施方案中,微粒固体不少于磨料的10重量%或不少于20重量%。这类磨料可以任选含有在研磨之前或之后添加的连接料。
连接料是能够在有机液体挥发时粘合组合物的聚合材料。
连接料是聚合材料,包括天然和合成材料。在一个实施方案中,连接料包括聚(甲基)丙烯酸酯、聚苯乙烯类、聚酯、聚氨酯、醇酸树脂、多糖,例如纤维素,和天然蛋白质,例如酪蛋白。在一个实施方案中,连接料在组合物中以微粒固体量的大于100%,大于200%,大于300%,或大于400%存在。
磨料中任选的连接料的量可以在宽限度内变化,但通常不少于磨料的连续/液相的10重量%,通常不少于20重量%。在一个实施方案中,连接料的量不超过磨料的连续/液相的50重量%,或不超过40重量%。
磨料中分散剂的量取决于微粒固体的量,但通常为磨料的0.5至5重量%。
由本发明的组合物制成的分散体和磨料特别适合用在涂料和漆料,尤其是高固含量漆料;油墨,尤其是苯胺油墨、凹印油墨和丝网印刷油墨;非水陶瓷工艺,尤其是带涂、刮刀、挤出和注射成型工艺;复合材料、化妆品、连接料和塑料中。
如上所述,式(1)和(1a)的许多分散剂是新的。因此,根据本发明的另一方面,提供了包含微粒固体、有机液体、连接料和式(1)、(1a)和(1b)的化合物及其盐的漆料或油墨。
根据本发明的再一方面,提供了式(1)、(1a)和(1b)的化合物及其盐,其中Z是数均分子量不小于1500的聚胺和/或聚亚胺且其中(0-v)为0,例如该式不包括添加的氧化物、脲或二元酸或酐(W)。
通过下列实施例进一步例证本发明,其中除非另行指明,所有量均按重量份计。
实施例
实施例1
中间体1:1∶1聚醚胺∶丙烯酸2-羟乙酯的合成
将丙烯酸2-羟乙酯(5.25克,45.2毫摩尔,购自Aldrich)、2,6-二叔丁基-4-甲酚(0.005克)和大约MW 1650的聚醚胺C12-C15混合脂肪醇封端聚丙氧基化物胺(100克,45.2毫摩尔,如US 5,094,667中制备,75重量%活性物)在70℃在空气气氛中搅拌4小时以产生透明的黄色液体(105克),IR表明不存在烯键。
中间体2:1∶1∶1聚醚胺∶丙烯酸2-羟乙酯∶琥珀酸酐的合成
将中间体1(50克,20.4毫摩尔)和琥珀酸酐(2.04克,20.4毫摩尔,购自Aldrich批号31081-050)在80℃在氮气氛下搅拌18小时,产生透明黄色液体(52克),IR表明不存在酐基团且存在羰基酰胺(1659cm-1)。混合物的酸值测得为24.4毫克KOH/克。
分散剂1
将聚乙烯亚胺SP200(3.6克,1毫摩尔,购自Nippon Shokubai MW10000)在80℃在氮气氛下添加到搅拌的中间体2(52克,20毫摩尔)中。在15分钟后,将整个混合物在120℃在氮气氛下搅拌6小时以产生粘性琥珀色胶质物(55克)。该混合物的酸值测得为19.4毫克KOH/克。分离20克该产物。
分散剂2
将分散剂1的混合物在120℃在氮气氛下进一步加热6小时以产生粘性琥珀色胶质物(35克)。该混合物的酸值测得为17.2毫克KOH/克。
实施例2-11
重复中间体1的方法,只是使用下表1中所示的原材料代替实施例1中所用的聚醚胺和丙烯酸2-羟乙酯。聚醚胺与丙烯酸酯的摩尔比为1∶1。使用下表中标出的材料准备实施例2-11。
实施例 | 中间体 | 聚醚胺 | 丙烯酸酯 |
2 | 3 | Jeffamine M2005 | 2-HEA |
3 | 4 | C12-C15聚丙氧基化物胺MW 1650 | MeOPEG Ac |
4 | 5 | MeOPEG 350聚丙氧基化物胺MW 1420 | 2-HEA |
5 | 6 | Jeffamine M2005 | 2-DMAEA |
6 | 7 | MeOPEG 350聚丙氧基化物胺MW 1420 | 2-DMAEA |
7 | 8 | MeOPEG 350聚丙氧基化物胺MW 1800 | EGMEA |
8 | 9 | Jeffamine M2005 | DEGMEA |
9 | 10 | C12-C15聚丙氧基化物胺MW 1650 | DEAEA |
10 | 11 | C12-C15聚丙氧基化物胺MW 1650 | DMAPA |
11 | 12 | C12-C15聚丙氧基化物胺MW 1650 | DMAPMA |
表1的脚注
2-HEA是丙烯酸2-羟乙酯,购自Aldrich
MeOPEG Ac是聚乙二醇甲基醚丙烯酸酯,大约Mn454,购自Aldrich
2-DMAEA是丙烯酸2-二甲基氨基乙酯,购自Aldrich
EGMEA是乙二醇甲基醚丙烯酸酯,购自Aldrich
DEGMEA是二乙二醇甲基乙基丙烯酸酯,购自Aldrich
DEAEA是丙烯酸2-二乙基氨基乙酯,购自Aldrich
DMAPA是丙烯酸3-二甲基氨基丙酯
DMAPMA是3-二甲基氨基丙基甲基丙烯酰胺
实施例12-21
重复中间体2的方法,只是使用下表2中所示的原材料代替实施例1中所用的中间体1。下面显示了组分的摩尔比。
实施例 | 中间体 | 中间体*** | 酐 | 摩尔比 |
12 | 13 | 3 | SUCCA | 1∶1 |
13 | 14 | 4 | SUCCA | 1∶1 |
14 | 15 | 5 | SUCCA | 1∶1 |
15 | 16 | 6 | SUCCA | 1∶1 |
16 | 17 | 7 | SUCCA | 1∶1 |
17 | 18 | 8 | SUCCA | 1∶1 |
18 | 19 | 9 | SUCCA | 1∶1 |
19 | 20 | 10 | SUCCA | 1∶1 |
20 | 21 | 11 | SUCCA | 1∶1 |
21 | 22 | 12 | SUCCA | 1∶1 |
表2的脚注
中间体***与SUCCA反应形成分散剂
SUCCA是琥珀酸酐,购自Aldrich
实施例22-36
重复分散剂1和2的方法,只是使用下表3中所示的原材料代替实施例1中所用的中间体2和聚乙烯亚胺SP200。组分的重量比显示在下表中。
实施例 | 分散剂 | 中间体 | PEI | 重量比* | 酸值(毫克KOH/克) |
22 | 3 | 3 | SP200 | 11∶1 | 16.1 |
23 | 4 | 4 | SP200 | 11∶1 | 28 |
24 | 5 | 5 | SP200 | 11∶1 | 15.5 |
25 | 6 | 6 | SP200 | 11∶1 | 23.2 |
26 | 7 | 5 | SP200 | 17∶1 | 30 |
27 | 8 | 8 | SP075 | 11∶1 | 27 |
28 | 9 | 1 | SP200 | 11∶1 | 16.3 |
29 | 10 | 8 | SP200 | 17∶1 | 22 |
30 | 11 | 7 | SP050 | 15∶1 | 19.5 |
31 | 12 | 9 | SP030 | 9∶1 | 17.6 |
32 | 13 | 10 | PAA05 | 10∶1 | 12.5 |
33 | 14 | 11 | SP075 | 5∶1 | 17 |
34 | 15 | 12 | SP200 | 13∶1 | 15.7 |
35 | 16 | 6 | SP200 | 11∶1 | 12 |
36 | 17 | 6 | SP200 | 17∶1 | 8 |
[0179] 表3的脚注
重量比*是中间体与PEI的重量比。
SP030、SP050和SP075是Mn分别为3000、5000和7500的聚乙烯亚胺,购自Nippon Shokubai
PAA 05是MW 5000的聚烯丙胺,购自Nitto Boseki Co Ltd.
对比例1是如US 4,645,611中所述用月桂酸封端并与聚乙烯亚胺反应的聚(ε-己内酯)。
对比例2是不存在分散剂的情况下制成的磨料。
对比例3是按照与分散剂1或2相同的方法制成的相同物质,只是不使用丙烯酸2-羟乙酯。
磨料的制备
使用各种分散剂(实施例1、2和37-47)和对比例1和2制备一系列品红磨料。通过将分散剂(0.45克)溶解在7.55克4∶1比率的MPA∶丁醇(MPA=甲氧基丙基乙酸酯)溶剂混合物中,制备该磨料。添加玻璃珠(3毫米,17份)和Monolite Rubine 3B(购自Heubach 2.0份)并将混合物在水平摇动器上摇动16小时。然后使用A至E的任意等级(好至差)评测所得分散体的流动性。所得研磨等级为:
实施例 | 分散剂 | 研磨等级 |
1 | 1 | C |
1 | 2 | C |
37 | 3 | B/C |
38 | 4 | C/D |
39 | 5 | C |
40 | 6 | B |
41 | 7 | B/C |
42 | 8 | B |
43 | 9 | C |
44 | 10 | B/C |
45 | 11 | B/C |
46 | 13 | C/D |
47 | 17 | C |
- | 对比例1 | C/D |
- | 对比例2 | E |
[0189] 絮凝试验
通过将含有分散剂(1或2)或对比例3的磨料(着色剂)与聚酯白漆掺合以进行1/10有色/白色稀释(reduction),制备实施例。漆料含有10克聚酯白漆、大约4.1克着色剂和2克二甲苯。然后为均匀性,将漆料在Skandex磨中掺合10分钟,然后在实验室辊上掺合20分钟。然后在Automatic K-Bar涂布机(使用K-Bar No.4)上测试掺合漆,在涂布的黑/白卡片上制备并排的下拉线(drawdowns)。使实施例风干至少30分钟,然后在150℃炉中放置20分钟。使用设定在20°和60°视角的光泽计测量图案的光泽度(反映絮凝变化)。所得结果概括如下:
实施例 | 光泽60° | 光泽20° | 絮凝变化 |
分散剂1 | 90.1 | 69.3 | 1.18 |
分散剂2 | 89.7 | 70.6 | 0.8 |
对比例3** | 91.9 | 75.2 | 15.58 |
**对比例3具有差的分离和指擦性(finger rub)。
本文所用的术语“烃基取代基”或“烃基”以本领域技术人员公知的其普通含义使用。具体地,其是指具有直接连接到分子其余部分上的碳原子并主要具有烃性质的基团。烃基的例子包括:
(i)烃取代基,即,脂族(例如烷基或烯基)、脂环族(例如环烷基、环烯基)取代基,和芳族、脂族和脂环族取代的芳族取代基,以及环状取代基,其中该环经由该分子的另一部分完成(例如,两个取代基一起构成环);
(ii)取代烃取代基,即,含有非烃基团的取代基,该非烃基团在本发明中不改变取代基的主要烃性质(例如卤素(尤其是氯基和氟基)、羟基、烷氧基、巯基、烷基巯基、硝基、亚硝基和硫氧基);
(iii)杂取代基,即在具有主要烃性质的同时,在本发明中,在本来由碳原子构成的环或链中含有非碳基团的取代基。杂原子包括硫、 氧、氮并包括取代基,如吡啶基、呋喃基、噻吩基和咪唑基。一般而言,对烃基中的每10个碳原子,存在不多于2个,或不多于1个非烃取代基;通常,在烃基中没有非烃取代基。
上文引用的每一文献经此引用并入本文。除了在实施例中,或在另行明确指出的地方外,本说明书中指定材料量、反应条件、分子量、碳原子数等的所有数量均被理解为用词语“大约”修饰。除非另行指明,本文引用的每一化学品或组分应该解释为商品级材料,其可能含有异构体、副产物、衍生物和通常认为在商品级中存在的其它这类材料。但是,除非另行指明,排除商品材料中通常存在的任何溶剂或稀释油来表示每一化学组分的量。要理解的是,本文所列的上限和下限量、范围和比率界限可以独立地结合。类似地,本发明的每一元素的范围和量可以与任何其它元素的范围或量一起使用。
Claims (15)
1.包含式(1)的化合物及其盐的分散剂:
E-O-(Y)x-T-NR′-A-Z-W0-v
式(1)
其中,2个以上E-O-(Y)X-T-NR′-A-基团连接到Z上,且这些基团相同或不同,
E是R或R-NR′-T-;
R是H或C1-50-烃基;
R′是(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基,或C1-8-烃基;
Y是C2-4-亚烷氧基;
T是C2-4亚烷基;
A是源自式HOOC-B-COOH的任何二元酸或其酐的残基,其中B是直接键或含有1至20个碳原子的二价有机部分;
Z是聚胺和/或聚亚胺的残基,其中该聚胺是聚乙烯胺、亚烷基多胺或聚烯丙胺和该聚亚胺是聚(C2-6-亚烷基亚胺);
W是通过与氧、过氧化氢或过硫酸铵反应得到的氧化物的残基、脲的残基或选自马来酸、丙二酸、丁二酸和邻苯二甲酸、马来酸酐、戊二酸酐、丁二酸酐和邻苯二甲酸酐的二元酸或其酐的残基;
x为2至90;且
(0-v)是指0至v的值,其中v代表Z中不带基团E-O-(Y)x-T-NR′-A-的氨基和/或亚氨基的最大可得数量。
2.如权利要求1所述的分散剂,其中Y是C3-4-亚烷氧基。
3.如权利要求1所述的分散剂,其中Y是C3-4-亚烷氧基且(Y)x所示的链为-CH2CH2CH2CH2O-、-CH2CH(CH3)O-或-CH2-CH(CH2-CH3)-O-。
4.如权利要求1所述的分散剂,其中W是独立地源自马来酸、丙二酸、丁二酸和邻苯二甲酸、马来酸酐、戊二酸酐、丁二酸酐和邻苯二甲酸酐的残基。
5.如权利要求1所述的分散剂,其中Z所代表的基团是聚乙烯亚胺。
6.包含微粒固体、有机介质和/或水和式(1)的化合物及其盐的组合物:
E-O-(Y)x-T-NR′-A-Z-W0-v
式(1)
其中,2个以上E-O-(Y)X-T-NR′-A-基团连接到Z上,且这些基团相同或不同,
E是R或R-NR′-T-;
R是H或C1-50-烃基;
R′是(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或环氧化物的残基,或C1-8-烃基;
Y是C2-4-亚烷氧基;
T是C2-4亚烷基;
A是源自式HOOC-B-COOH的任何二元酸或其酐的残基,其中B是直接键或含有1至20个碳原子的二价有机部分;
Z是聚胺和/或聚亚胺的残基,其中该聚胺是聚乙烯胺、亚烷基多胺或聚烯丙胺和该聚亚胺是聚(C2-6-亚烷基亚胺);
W是通过与氧、过氧化氢或过硫酸铵反应得到的氧化物的残基、脲的残基、或选自马来酸、丙二酸、丁二酸和邻苯二甲酸、马来酸酐、戊二酸酐、丁二酸酐和邻苯二甲酸酐的二元酸或其酐的残基;
x为2至90;且
v代表Z中不带基团E-O-(Y)x-T-NR′-A-的氨基和/或亚氨基的最大可得数量。
7.如权利要求6所述的组合物,其中有机介质是有机液体或塑料。
8.如权利要求7所述的组合物,其中有机液体包含总有机液体的至少0.1重量%的极性有机液体。
9.如权利要求6所述的组合物,其中微粒固体是颜料。
10.如权利要求6的组合物,是漆料或油墨形式,其中所述有机介质和/或水包含有机液体。
11.如权利要求6的组合物,是磨料形式,其中所述有机介质和/或水包含有机液体。
12.如权利要求6所述的组合物,其中Y为C3-4-亚烷氧基。
13.如权利要求6所述的组合物,其中Y是C3-4-亚烷氧基且(Y)x所示的链为-CH2CH2CH2CH2O-、-CH2CH(CH3)O-或-CH2-CH(CH2-CH3)-O-。
14.如权利要求6所述的组合物,其中W是独立地源自马来酸、丙二酸、丁二酸和邻苯二甲酸、马来酸酐、戊二酸酐、丁二酸酐和邻苯二甲酸酐的残基。
15.如权利要求6所述的组合物,其中Z所代表的基团是聚乙烯亚胺。
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Publication number | Priority date | Publication date | Assignee | Title |
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US8263700B2 (en) * | 2010-06-01 | 2012-09-11 | Ppg Industries Ohio, Inc. | Pigment dispersions, related coating compositions and coated substrates |
JP5575594B2 (ja) * | 2010-09-17 | 2014-08-20 | 富士フイルム株式会社 | インク組成物、インクセットおよび画像形成方法 |
IT1404805B1 (it) | 2011-02-10 | 2013-11-29 | Lamberti Spa | Disperdenti |
EP2495271B1 (en) * | 2011-03-04 | 2014-04-23 | 3M Innovative Properties Co. | Polyether hybrid epoxy curatives |
TWI643884B (zh) | 2013-09-06 | 2018-12-11 | 盧伯利索先進材料有限公司 | 多元酸多元鹼接枝共聚物分散劑 |
EP3230037B1 (en) | 2014-12-09 | 2020-04-08 | Lubrizol Advanced Materials, Inc. | Additive to prevent phase separation of low profile additive in unsaturated thermoset polyester compositions |
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CA3076315A1 (en) | 2017-09-19 | 2019-03-28 | Lubrizol Advanced Materials, Inc. | Multi-amine polyester dispersant made via an anhydride intermediate |
CN110437372A (zh) * | 2018-05-03 | 2019-11-12 | 史增谦 | 碳纳米管分散剂及其制备方法和应用 |
WO2020055691A1 (en) | 2018-09-10 | 2020-03-19 | Lubrizol Advanced Materials, Inc. | Multi-amine polyester dispersant and method of making |
BR112021018079A2 (pt) | 2019-03-14 | 2021-11-23 | Lubrizol Advanced Mat Inc | Dispersante, e, método de preparação de um dispersante |
US11981831B2 (en) | 2019-03-14 | 2024-05-14 | Lubrizol Advanced Materials, Inc. | Multi-amine dispersant made via an anhydride intermediate |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0359034A1 (en) * | 1988-08-31 | 1990-03-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Dispersant for nonaqueous systems |
CN1322228A (zh) * | 1998-10-06 | 2001-11-14 | 纳幕尔杜邦公司 | 具有改进稳定性的分散体 |
CN1374881A (zh) * | 1999-09-18 | 2002-10-16 | 艾夫西亚有限公司 | 聚酯分散剂 |
CN1531457A (zh) * | 2001-04-20 | 2004-09-22 | 分散剂 | |
WO2005010109A2 (en) * | 2003-07-18 | 2005-02-03 | The Lubrizol Corporation | Compositions |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4224212A (en) | 1977-07-15 | 1980-09-23 | Imperial Chemical Industries Limited | Dispersing agents, dispersions containing these agents and paints and inks made from the dispersions |
NL8104025A (nl) | 1981-08-29 | 1983-03-16 | Stamicarbon | Werkwijze voor de bereiding van ethercarboxylaten. |
GB8402801D0 (en) | 1984-02-02 | 1984-03-07 | Ici Plc | Dispersion |
EP0208041B1 (en) | 1985-01-22 | 1991-05-15 | Imperial Chemical Industries Plc | Dispersant containing composition |
US4713487A (en) | 1985-06-06 | 1987-12-15 | Kao Corporation | Ether carboxylates and process for preparing same |
JPH062222B2 (ja) * | 1988-11-07 | 1994-01-12 | 第一工業製薬株式会社 | 分散剤 |
US4865621A (en) * | 1989-01-27 | 1989-09-12 | Texaco Inc. | Ori-inhibited and deposit-resistant motor fuel composition |
GB9622783D0 (en) * | 1996-11-01 | 1997-01-08 | Zeneca Ltd | Dispersants |
JPH11293173A (ja) * | 1998-04-06 | 1999-10-26 | Nippon Shokubai Co Ltd | 印刷画像耐水性向上剤およびその用途 |
NL1013105C2 (nl) * | 1999-09-21 | 2001-03-22 | Dsm Nv | Vlamdovend mengsel. |
GB0009798D0 (en) * | 2000-04-20 | 2000-06-07 | Avecia Ltd | Dispersants |
AU2001256552A1 (en) * | 2000-06-09 | 2001-12-17 | Avecia Limited | Thickeners |
GB0107183D0 (en) * | 2001-03-22 | 2001-05-09 | Avecia Ltd | Paint compositions |
US7442327B2 (en) * | 2003-03-05 | 2008-10-28 | The Lubrizol Corporation | Use of dispersions in making electronic devices |
US7045580B2 (en) * | 2003-10-20 | 2006-05-16 | The Lubrizol Corporation | Oil-in-water emulsifiers |
DE10356341A1 (de) * | 2003-11-28 | 2005-06-23 | Bayer Chemicals Ag | Alkoxylierte Polyalkylenimine mit anionischen Gruppen und ihre Verwendung |
CN101065447B (zh) * | 2004-12-21 | 2012-07-18 | 路博润有限公司 | 组合物 |
EP1957189B1 (en) * | 2005-12-06 | 2011-10-19 | Lubrizol Limited | Novel dispersant and compositions thereof |
WO2007102911A2 (en) * | 2005-12-15 | 2007-09-13 | Lubrizol Limited | Novel dispersant and compositions thereof |
-
2006
- 2006-05-01 KR KR1020077029088A patent/KR101314784B1/ko active IP Right Grant
- 2006-05-01 CN CN200680016200XA patent/CN101175559B/zh active Active
- 2006-05-01 WO PCT/US2006/016737 patent/WO2006124264A1/en active Application Filing
- 2006-05-01 ES ES06752052.8T patent/ES2482143T3/es active Active
- 2006-05-01 EP EP06752052.8A patent/EP1879689B1/en active Active
- 2006-05-01 JP JP2008511164A patent/JP5015144B2/ja active Active
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0359034A1 (en) * | 1988-08-31 | 1990-03-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Dispersant for nonaqueous systems |
CN1322228A (zh) * | 1998-10-06 | 2001-11-14 | 纳幕尔杜邦公司 | 具有改进稳定性的分散体 |
CN1374881A (zh) * | 1999-09-18 | 2002-10-16 | 艾夫西亚有限公司 | 聚酯分散剂 |
CN1531457A (zh) * | 2001-04-20 | 2004-09-22 | 分散剂 | |
WO2005010109A2 (en) * | 2003-07-18 | 2005-02-03 | The Lubrizol Corporation | Compositions |
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ES2482143T3 (es) | 2014-08-01 |
US20090131555A1 (en) | 2009-05-21 |
JP5015144B2 (ja) | 2012-08-29 |
JP2008540764A (ja) | 2008-11-20 |
CN101175559A (zh) | 2008-05-07 |
US8168713B2 (en) | 2012-05-01 |
EP1879689B1 (en) | 2014-07-09 |
KR20080016632A (ko) | 2008-02-21 |
KR101314784B1 (ko) | 2013-10-08 |
WO2006124264A1 (en) | 2006-11-23 |
EP1879689A1 (en) | 2008-01-23 |
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