CN1377388A - 用于塑料应用的脱水山梨醇酯处理的颜料 - Google Patents
用于塑料应用的脱水山梨醇酯处理的颜料 Download PDFInfo
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- CN1377388A CN1377388A CN00813761A CN00813761A CN1377388A CN 1377388 A CN1377388 A CN 1377388A CN 00813761 A CN00813761 A CN 00813761A CN 00813761 A CN00813761 A CN 00813761A CN 1377388 A CN1377388 A CN 1377388A
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- 239000000049 pigment Substances 0.000 title claims abstract description 40
- -1 Sorbitan ester Chemical class 0.000 title abstract description 34
- 229920003023 plastic Polymers 0.000 title description 6
- 239000004033 plastic Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000000654 additive Substances 0.000 claims abstract description 9
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 5
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 229910052788 barium Inorganic materials 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 4
- 229910052742 iron Inorganic materials 0.000 claims abstract description 4
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 4
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 4
- 150000003624 transition metals Chemical class 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
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- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 claims description 12
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
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- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- 229940035048 sorbitan monostearate Drugs 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
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- 125000001544 thienyl group Chemical group 0.000 claims description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001768 cations Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000004800 polyvinyl chloride Substances 0.000 description 11
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 8
- 239000004902 Softening Agent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229940035044 sorbitan monolaurate Drugs 0.000 description 5
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 5
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 5
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 4
- 229940038384 octadecane Drugs 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 239000011347 resin Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000004147 Sorbitan trioleate Substances 0.000 description 3
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 3
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- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 3
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
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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
- 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
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B67/0072—Preparations with anionic dyes or reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
组合物、它的制备方法和用途,以及脱水山梨醇酯I作为改进着色强度和分散性的添加剂的用途。所述组合物含有:(a)1-20%,优选1-10%重量的式(I)的脱水山梨醇酯,其中R1和R2彼此独立表示C1-C20烷基或C2-C20链烯基,和(b)99-80%,优选99-90%重量的式(II)或式(III)的金属或铵色淀的单偶氮颜料,其中R3、R4、R5、R6、R7和R8彼此独立表示氢、C1-C20烷基、C1-C20烷氧基、C2-C20链烯基、C1-C20烷硫基、C1-C20烷氧羰基、羟基C1-C4烷氧基、苯基、苄基、苯硫基、氟、氯、溴、碘、-CN、-NO2、-CF3、-COR9、-COOR9、-CONR9R10、-SO2R9、-SO2NR9R10、-NR9NR10,其中R9和R10各彼此独立为氢、-OH、C1-4烷基或苯基,R3、R4、R5、R6、R7和R8中的至少一个为-COOH或-SO3H,M可以是NH4 +,或者碱金属、碱土金属如Na、K、Mg、Ca、Sr、Ba的阳离子,或者过渡金属如Mn、Co、Ni、Cu、Fe或Al的阳离子。
Description
本发明涉及一种组合物、该组合物的制备方法和它的用途,以及脱水山梨醇酯I作为改进着色强度和分散性能的添加剂的用途,所述组合物含有:
(a)1-20%,优选1-10%重量的式I的脱水山梨醇酯其中R1和R2彼此独立表示C1-C20烷基或C2-C20链烯基,和
(b)99-80%,优选99-90%重量的式II或式III的金属或铵色淀的单偶氮颜料 其中R3、R4、R5、R6、R7和R8彼此独立表示氢、C1-C20烷基、C1-C20烷氧基、C2-C20链烯基、C1-C20烷硫基(alkylthiol)、C1-C20烷氧羰基、羟基C1-C4烷氧基、苯基、苄基、苯硫基、氟、氯、溴、碘、-CN、-NO2、-CF3、-COR9、-COOR9、-CONR9R10、-SO2R9、-SO2NR9R10、-NR9NR10,其中R9和R10各彼此独立为氢、-OH、C1-4烷基或苯基,R3、R4、R5、R6、R7和R8中的至少一个为-COOH或-SO3H,M可以是NH4 +,或者碱金属、碱土金属如Na、K、Mg、Ca、Sr、Ba的阳离子,或者过渡金属如Mn、Co、Ni、Cu、Fe或Al的阳离子。
WO 9851160描述了一种颜料或染料组合物,该组合物含2-10%重量颜料或染料、3-30%重量聚氧乙烯脱水山梨糖醇脂肪酸酯、1-10%重量另一种脱水山梨糖醇脂肪酸酯和分散剂。
JP-A2 10204243描述了具有改进的聚合物颜色分散性的1,1-二氯乙烯基聚合物组合物,该组合物含所述聚合物、30%重量颜料红208、2%重量脱水山梨醇三油酸酯和其他添加剂。
US 4,177,082描述了无粉尘、易于分散的颜料或染料颗粒,其中用羟乙基纤维素、胺、脱水山梨糖醇三硬脂酸酯和邻苯二甲酸二环己酯的混合物在升高的温度下对颜料进行处理,之后调节pH,最后与聚合物如聚氯乙烯(“PVC”)或聚乙烯(“PE”)混合。
JP-A2 50101427描述了含颜料、PVC、二酚衍生物和聚乙二醇脱水山梨糖醇单月桂酸酯的组合物。根据该文件,双酚A的加入对于良好的分散性是必要的。
但是,上述组合物的分散性和着色强度都不足以满足今天的需求。而且,在所有的情况下,颜料和添加剂,尤其是脱水山梨糖醇脂肪酸酯同时混合在一起。此外,仅由颜料和脱水山梨糖醇脂肪酸酯组成的组合物是未知的,总是需要使用其他添加剂。
因此,本发明的目的是提供具有改进的着色强度和分散性能的、由金属或铵色淀的单偶氮颜料组成的组合物。特别是,本发明的目的是通过加入适当的添加剂来改进颜料黄191∶1的着色强度和分散性能。此外,本发明的组合物应当被用在与食品相关(contact)的应用中。
因此,发现了以上定义的组合物。
对本领域技术人员来说,金属或铵色淀的单偶氮颜料如颜料黄61、颜料黄62∶1、颜料黄100、颜料黄133、颜料黄168、颜料黄169、颜料黄183(如BASF的PaliotolYellow K-2270)、颜料黄190(如Hoechst的PV Fast yellow HGR)和颜料黄191∶1是众所周知的,例如可以从Herbst/Hunger,“Industrielle Organische Pigmente”,第2版,VCH 1995,240-243页得知。
本发明优选的实施方案涉及基本上由下述物质组成的组合物:
(a)1-10%重量脱水山梨醇酯I,优选其中R1=R2=C8-C20烷基或
C8-C20链烯基,和
(b)99-90%重量化合物II或化合物III,优选其中R3、R4、R5、R6、
R7和R8彼此独立表示氢、甲基、甲氧基、氟、氯、溴、碘、
-NO2、-CF3、-COOR9、-SO2R9,其中优选R9表示氢或-OH,
更优选R3、R4、R5、R6、R7和R8中的至少一个彼此独立表
示-COOH或-SO3H,其中M表示铵或Ca、Sr或Al的阳离子。
本发明的另一种优选的实施方案涉及基本上由下述物质组成的组合物:
(a)1-10%重量的脱水山梨醇酯I,其中R1表示正十一烷基,和
特别优选的实施方案涉及由下述物质组成的组合物:
(a)95%重量式IIIa的单偶氮衍生物,和
(b)5%重量脱水山梨糖醇单月桂酸酯。
另一特别优选的实施方案涉及由下述物质组成的组合物:
(b)5%重量脱水山梨糖醇单硬脂酸酯。
C1-C20烷基表示甲基、乙基、正-、异-丙基、正-、异-、仲-、叔-丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基,优选C8-C20烷基如正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基;
C1-C4烷基表示甲基、乙基、正-、异-丙基、正-、异-、仲-、叔-丁基;
C1-C20烷氧基表示甲氧基、乙氧基、正-、异-丙氧基、正-、异-、仲-、叔-丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基、正壬氧基、正癸氧基、正十一烷氧基、正十二烷氧基、正十三烷氧基、正十四烷氧基、正十五烷氧基、正十六烷氧基、正十七烷氧基、正-十八烷氧基、正十九烷氧基、正二十烷氧基;
C2-C20链烯基表示乙烯基、正-、异-丙烯基、正-、异-、仲-、叔-丁烯基、正戊烯基、正己烯基、正庚烯基、正辛烯基、正壬烯基、正癸烯基、正十一烯基、正十二烯基、正十三烯基、正十四烯基、正十五烯基、正十六烯基、正十七烯基、正十八烯基、正十九烯基、正二十烯基;
C1-C20烷硫基表示甲硫基、乙硫基、正-、异-丙硫基、正-、异-、仲-、叔-丁硫基、正戊硫基、正己硫基、正庚硫基、正辛硫基、正壬硫基、正癸硫基、正十一烷硫基、正十二烷硫基、正十三烷硫基、正十四烷硫基、正十五烷硫基、正十六烷硫基、正十七烷硫基、正-十八烷硫基、正十九烷硫基、正二十烷硫基;
C1-C20烷氧羰基表示甲氧羰基、乙氧羰基、正-、异-丙氧羰基、正-、异-、仲-、叔-丁氧羰基、正戊氧羰基、正己氧羰基、正庚氧羰基、正辛氧羰基、正壬氧羰基、正癸氧羰基、正十一烷氧羰基、正十二烷氧羰基、正十三烷氧羰基、正十四烷氧羰基、正十五烷氧羰基、正十六烷氧羰基、正十七烷氧羰基、正十八烷氧羰基、正十九烷氧羰基、正二十烷氧羰基;
羟基C1-C4烷氧基表示羟基甲氧基、羟基乙氧基、羟基-正-丙氧基、羟基-异-丙氧基、羟基-正-丁氧基、羟基-异-丁氧基、羟基-仲-丁氧基、羟基-叔-丁氧基;
M可以是NH4 +,或者碱金属、碱土金属如Na、K、Mg、Ca、Sr、Ba的阳离子,或者过渡金属如Mn、Co、Ni、Cu、Fe或Al的阳离子。
本发明的另一种实施方案是制备本发明的组合物的方法,其中
(a)将式II或III的颜料、脱水山梨醇酯I和水的混合物加热至
70-100℃的温度,优选至回流1-60分钟,然后
(b)将得到的混合物冷却至30-70℃的温度,之后
(c)从液体部分分离固体部分,
(d)在50-90℃的温度下干燥得到的固体部分,和
(e)任选将由此干燥的颜料组合物过筛至所需的粒径。
另一种优选的实施方案涉及制备本发明的组合物的方法,其特征在于:
(a)使式IV的氨基化合物与亚硝酸钠反应,
反应,
(c)向(b)中得到的反应混合物中,或者在反应步骤(a)和/或(b)之
一期间加入有效量的金属盐或铵盐MX,其中X表示阴离子,
(d)向(b)中得到的反应混合物中,或者在反应步骤(a)和/或(b)之
一期间加入脱水山梨醇酯I。
通用的合成方法对于本领域技术人员来说是已知的,例如从US5,151,505得知。
本发明的另一个实施方案涉及对高分子量有机物质(通常具有103-107g/mol的分子量)着色的方法,该方法是通过本领域已知的方法掺入本发明的组合物。高分子量有机物质可以使用下述物质,如生物高分子和塑料材料,包括纤维。
可以用本发明的组合物着色的适当的高分子量有机物质的实例有:乙烯基聚合物,例如聚苯乙烯、聚-α-甲基苯乙烯、聚对甲基苯乙烯、聚对羟基苯乙烯、聚对羟基苯基苯乙烯、聚甲基丙烯酸甲酯和聚丙烯酰胺以及相应的甲基丙烯酸化合物、聚马来酸甲酯、聚丙烯腈、聚甲基丙烯腈、聚氯乙烯、聚氟乙烯、聚偏1,1-二氯乙烯、聚偏1,1-二氟乙烯、聚乙酸乙烯酯、聚甲基乙烯基醚和聚丁基乙烯基醚;衍生自马来酰亚胺和/或马来酸酐的聚合物,例如马来酸酐与苯乙烯的共聚物;聚乙烯基吡咯烷酮;ABS;ASA;聚酰胺;聚酰亚胺;聚酰胺酰亚胺;聚砜;聚醚砜;聚苯醚;聚氨基甲酸酯;聚脲;聚碳酸酯;聚亚芳基;聚亚芳基硫醚;聚环氧化物;聚烯烃如聚乙烯和聚丙烯;聚链二烯;生物高分子和它的衍生物例如纤维素、纤维素醚和酯,如乙基纤维素、硝基纤维素、乙酸纤维素和丁酸纤维素、淀粉、甲壳质、脱乙酰壳多糖、明胶、玉米蛋白;天然树脂;合成树脂如醇酸树脂、丙烯酸树脂、酚醛树脂、环氧树脂、氨基甲醛树脂如脲/甲醛树脂和三聚氰胺/甲醛树脂;硫化橡胶;酪蛋白;硅氧烷和有机硅树脂;橡胶,氯化橡胶;以及被用作例如油漆体系的粘结剂的聚合物,例如衍生自C1-C6醛如甲醛和乙醛的线型酚醛清漆,以及双核或单核,优选单核酚,如果需要,所述酚可以被一个或两个C1-C9烷基、一个或两个卤原子或一个苯环取代,其例子有邻-、间-或对甲酚、二甲苯、对叔丁基苯酚、邻-、间-或对-壬基苯酚、对氯苯酚或对苯基苯酚,或者具有超过一个酚基的化合物如间苯二酚、双(4-羟苯基)甲烷或2,2-双(4-羟苯基)丙烷;以及所述物质的适当的混合物。
特别优选的高分子量有机物质,特别是用于制备油漆体系、油墨或墨水的高分子量有机物质的例子有纤维素醚和酯,如乙基纤维素、硝基纤维素、乙酸纤维素和丁酸纤维素,天然树脂或合成树脂(聚合或缩合树脂)如氨基塑料,特别是脲/甲醛和三聚氰胺/甲醛树脂、醇酸树脂、酚醛塑料、聚碳酸酯、聚烯烃、聚苯乙烯、聚氯乙烯、聚酰胺、聚氨基甲酸酯、聚酯、ABS、ASA、聚苯醚、硫化橡胶、酪蛋白、硅氧烷和有机硅树脂以及它们彼此之间的可能的混合物。
在本发明特别优选的实施方案中,本发明的组合物被用来对聚氯乙烯、聚酰胺,特别是聚烯烃如聚乙烯和聚丙烯进行本体着色。
根据到目前为止所做的观察,根据最终用途的要求,可以以任意所需的量将本发明的组合物加入到待着色的物质中。在高分子量有机物质的情况下,例如基于被着色的高分子量有机物质的总重量,可以以0.01-40%,优选0.01-5%重量的量使用根据本发明制备的组合物。
因此,本发明的另一个实施方案涉及一种组合物,该组合物含有:
(a)基于被着色的高分子有机物质的总重量,0.01-50%,优选
0.01-5%,特别优选0.01-2%重量的本发明的组合物,和
(b)基于被着色的高分子有机物质的总重量,99.99-50%,优选
99.99-95%,特别优选99.99-98%重量的高分子有机物质,和
(c)如果需要,基于(a)和(b)的总重量,有效量例如0-50%重量的
常规添加剂,如流变学改良剂、分散剂、填料、油漆辅助剂、
催干剂、增塑剂、紫外线稳定剂和/或其他颜料或相应的前体。
为了生产非脆性的模制品或减小它们的脆性,可以在模塑之前向高分子量有机物质中加入所谓的增塑剂。增塑剂可以是例如磷酸、邻苯二甲酸和癸二酸的酯。可以在用本发明的组合物将高分子量有机物质着色之前、之中或之后入所述增塑剂。
为了得到不同的色调,可以以所需的量有利地将本发明的组合物用于与填料、透明和不透明白色、有色和/或黑色颜料以及常规闪光颜料的混合物中。
本发明的又一个实施方案涉及使用本发明的组合物制备分散体和相应的含本发明组合物的分散体的方法。
除了优选的聚合分散剂,或为了代替优选的聚合分散剂,可以将表面活性剂用作分散剂。它们可以是阴离子型、非离子型或两性表面活性剂。非聚合分散剂和一些聚合分散剂的详细目录公开在Manufacturing Confection Publishing Co.,(1990)110-129页,McCutcheon′s Functional Materials,北美版的分散剂部分。
对于高分子量有机物质的着色而言,通常使用辊炼机、混合设备或研磨设备将本发明组合物,任选以母炼胶的形式与高分子量有机物质混合。通常随后通过常规方法,例如砑光、压模、挤出、铺展、铸塑或注射成型使着色物质成为需要的最终形式。为了制备非刚性塑模或减少它们的脆性,经常要求在成型之前将所谓的增塑剂掺入到高分子量有机物质中。可以被用作这类增塑剂的化合物的例子有磷酸、邻苯二甲酸或癸二酸的酯。可以在将本发明组合物掺入到聚合物中之前或之后加入增塑剂。为了获得不同的色调,除了本发明的组合物外,也可以以所需量向所述高分子量有机物质中加入填料或其他着色组分,例如白色、有色或黑色颜料。
本发明的又一个实施方案涉及脱水山梨醇酯I作为改进金属或铵色淀的单偶氮颜料,优选颜料II或III的着色强度和分散性的添加剂的应用。
用本发明组合物着色的塑料和纤维表现出极好的着色强度,分散在其中的颜料表现出极好的分散性。
实施例
实施例1:在50℃,向水(500ml)中加入1-氨基-3-氯-4-甲基苯磺酸(46.5g)和氨(作为33%水溶液,14.5g)。将该混合物搅拌30分钟。加入活性炭(0.3g,由Quimir生产的Actibon C)、无定形硅石(0.6g,来自Johns-Manville的Celite J2),再搅拌15分钟。然后将混合物过滤,用水(60ml)洗涤滤渣,通过加入冰将由此得到的合并的滤液冷却至20℃。加入浓缩的含水HCl(41.3g)。通过加入亚硝酸钠(14.6g)使由此得到的淤浆重氮化。
在另一个容器中,向水(630ml)中加入1-(3′-磺基苯基)-4-甲基吡唑啉-2-酮(58.6g),进行搅拌以形成悬浮液。然后在10分钟内加入上述得到的重氮化溶液,通过加入浓的氨水溶液将pH调节至6.8。将淤浆搅拌30分钟。之后,加入在水(50ml)中的脱水山梨糖醇单月桂酸酯(2.5g),将混合物加热至回流5分钟。接下来,通过加入冰将淤浆冷却至70℃,过滤,并将得到的残余物在70℃干燥。将由此得到的干燥产品用250μm的筛子过筛,得到粉末状的颜料组合物。
实施例2:除使用脱水山梨糖醇单月桂酸酯(3.0g)和脱水山梨糖醇单棕榈酸酯(2.0g)外,重复实施例1。
实施例3a:将实施例1的组合物研磨8分钟,加入到低密度聚乙烯(来自Micropol,熔体流动指数为7,颜料/LDPE比例为0.3%重量)中。
实施例3b:除将实施例1的产品和TiO2研磨,加入到聚氯乙烯(来自EVC的Evipol,颜料/PVC比例为0.1%重量,TiO2/实施例1的颜料为10∶1)中外,重复实施例3a。
使用分光光度计(来自Datacolor)评估由此着色的高分子量有机物质的着色强度。在通过用显微镜观察着色的高分子量有机物质之后,通过视觉评估分散性能(分散性)。采用下述等级来进行视觉评估:1=极轻微地增加,2=轻微增加,3=轻微至中度增加,4=中度增加,5=中度至高度增加,其中将在×25放大率下每单位面积可见的聚集体的评估数的降低作为分散性的增加。结果概括在下表中。
实施例4:除使用实施例2的组合物外,重复实施例3。
对照实施例1:除使用颜料黄191∶1(来自Ciba Specialty Chemicals的CROMOPHTHAL YELLOW HRP)外,重复实施例3。表:
样品 | 在LDPE中的着色强度 | 在PVC中的分散性 |
实施例3 | 116 | 3 |
实施例4 | 118 | 3 |
对照实施例1 | 100 | 0 |
实施例5:在60℃,将4-氨基-3-硝基苯磺酸(31.6g)的铵盐溶解在水(125ml)中。加入在水(15ml)中的乙二胺四乙酸(0.38g)。加入浓HCl(27ml,浓度36%),通过加入冰将混合物的温度降至0℃。通过加入在水(30ml)中的亚硝酸钠(7.6g),将由此得到的淤浆重氮化至精确的终点。在重氮化期间将温度维持在5-7℃,在偶合前立即将温度降至0℃。
在另一个容器中,对N-乙酰乙酰邻氯代苯胺(23.4g)、47%重量氢氧化钠水溶液(9ml)和水(170ml)进行搅拌形成溶液。加入乙酸钠(4.7g)和碳酸钙(6.8g)。通过加入冰将混合物冷却至5℃。加入冷却的(5℃)冰醋酸(9.2g)在水(170ml)中的溶液,直到pH达到7.0。将由此得到的淤浆搅拌1小时。
在pH4.6-4.8的条件下,在1小时内向N-酰苯胺淤浆中加入重氮化溶液。用稀的NaOH溶液进行pH调节。将得到的黄色淤浆再搅拌1小时。加入脱水山梨糖醇单月桂酸酯(0.5g),通过喷汽将淤浆加热至85℃。通过加入冰将淤浆冷却至70℃,过滤,并在70℃下干燥。将由此得到的干燥颜料用250μm的筛子过筛,得到粉末状的颜料组合物。
实施例6:除加入脱水山梨糖醇单硬脂酸酯(2.5g)外,实施例6与实施例5完全相同。
实施例7:除加入脱水山梨醇三油酸酯(1.5g)外,实施例7与实施例5完全相同。
实施例8:除加入脱水山梨醇三油酸酯(2.5g)外,实施例8与实施例5完全相同。
实施例9-12:将实施例5-8的颜料制剂分散在聚氯乙烯中。此外,将除加入脱水山梨醇表面活性剂外,按与实施例5-8几乎相同的方式在实验室中制备的IRGALITEYellow WGP分散在相同的塑料中用于对照。在用显微镜观察塑料后,通过视觉评估分散体。采用下述等级来进行视觉评估:1=极轻微地增加,2=轻微增加,3=轻微至中度增加,4=中度增加,5=中度至高度增加。所有评估都对照未处理过的标准来进行。
样品 在PVC中的分散体
对照 0
实施例5 +3
实施例6 +3
实施例7 +3
实施例8 +3
Claims (8)
1.组合物,它含有:
(a)1-20%,优选1-10%重量的式I的脱水山梨醇酯其中R1和R2彼此独立表示C1-C20烷基或C2-C20链烯基,和
(b)99-80%,优选99-90%重量的式II或式III的金属或铵色淀的单
偶氮颜料其中R3、R4、R5、R6、R7和R8彼此独立表示氢、C1-C20烷基、C1-C20烷氧基、C2-C20链烯基、C1-C20烷硫基、C1-C20烷氧羰基、羟基C1-C4烷氧基、苯基、苄基、苯硫基、氟、氯、溴、碘、-CN、-NO2、-CF3、-COR9、-COOR9、-CONR9R10、-SO2R9、-SO2NR9R10、-NR9NR10,其中R9和R10各彼此独立为氢、-OH、C1-4烷基或苯基,R3、R4、R5、R6、R7和R8中的至少一个为-COOH或-SO3H,和M可以是NH4 +,或者碱金属、碱土金属如Na、K、Mg、Ca、Sr、Ba的阳离子,或者过渡金属如Mn、Co、Ni、Cu、Fe或Al的阳离子。
2.制备权利要求1的组合物的方法,其特征在于:
(a)将式II或III的颜料、脱水山梨醇酯I和水的混合物加热至
70-100℃的温度,优选至回流1-60分钟,然后
(b)将得到的混合物冷却至30-70℃的温度,之后
(c)从液体部分分离固体部分,
(d)在50-90℃的温度下干燥得到的固体部分,和
(e)任选将由此干燥的颜料组合物过筛至所需的粒径。
3.权利要求1的组合物用于将高分子量有机物质着色的用途。
4.含有权利要求1的组合物的高分子量有机物质。
5.权利要求1的组合物,它可以根据权利要求2获得。
6.脱水山梨醇酯I作为改进金属或铵色淀的单偶氮颜料的着色强度和分散性的添加剂的用途。
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JP4802510B2 (ja) * | 2004-11-30 | 2011-10-26 | Dic株式会社 | ジスアゾ顔料組成物及びその製造方法 |
EP2046897B1 (en) * | 2006-07-28 | 2011-10-19 | Inxel Trademark & Patents SAGL | Coating of inorganic pigments with aldehyde or ketone resins |
DE102007036126B4 (de) | 2007-08-01 | 2019-01-24 | Clariant International Ltd. | Neues Phenylpyrazolon-Farbmittel, Verfahren zu seiner Herstellung und seine Verwendung |
US8236198B2 (en) * | 2008-10-06 | 2012-08-07 | Xerox Corporation | Fluorescent nanoscale particles |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2340767A1 (de) | 1973-08-11 | 1975-02-27 | Bayer Ag | Azopigmente |
GB1563969A (en) | 1977-03-18 | 1980-04-02 | Ciba Geigy Ag | Pigment compositions |
GB2009204B (en) | 1977-10-15 | 1982-08-18 | Ciba Geigy Ag | Granulation of pegments |
GB2008601B (en) | 1977-11-18 | 1982-04-07 | Ciba Geigy Ag | Pigment composition |
DE3318073A1 (de) | 1983-05-18 | 1984-11-22 | Basf Ag, 6700 Ludwigshafen | Pyrazolonazofarbstoffe |
DE3784362D1 (de) | 1986-03-10 | 1993-04-08 | Ciba Geigy Ag | Neue aminsalze von azoverbindungen. |
DE3833226A1 (de) | 1988-09-30 | 1990-04-05 | Hoechst Ag | Monoazopigment, verfahren zu seiner herstellung und seine verwendung |
JPH0463878A (ja) * | 1990-06-30 | 1992-02-28 | Pentel Kk | 水性インキ |
JP2993096B2 (ja) * | 1990-10-24 | 1999-12-20 | セイコーエプソン株式会社 | インクジェットプリンタ用インク |
JPH04356568A (ja) * | 1991-06-03 | 1992-12-10 | Seiko Epson Corp | インクジェットプリンタ用インク |
DE4229442A1 (de) | 1992-09-03 | 1994-03-10 | Henkel Kgaa | Dispergiermittel |
SE9701828L (sv) | 1997-05-16 | 1998-11-16 | Tripasin Ab | Pigment/färgämneskomposition för infärgning av kollageninnehållande korvskinn samt användning därav |
-
1999
- 1999-10-04 GB GBGB9923233.2A patent/GB9923233D0/en not_active Ceased
-
2000
- 2000-09-19 US US09/664,812 patent/US6440206B1/en not_active Expired - Lifetime
- 2000-09-26 KR KR1020027004316A patent/KR20020065890A/ko active IP Right Grant
- 2000-09-26 BR BR0014471-1A patent/BR0014471A/pt not_active IP Right Cessation
- 2000-09-26 AU AU76596/00A patent/AU7659600A/en not_active Abandoned
- 2000-09-26 JP JP2001528494A patent/JP2003511508A/ja active Pending
- 2000-09-26 EP EP00966074A patent/EP1218450A1/en not_active Withdrawn
- 2000-09-26 WO PCT/EP2000/009375 patent/WO2001025335A1/en not_active Application Discontinuation
- 2000-09-26 CN CN00813761A patent/CN1377388A/zh active Pending
- 2000-09-26 CA CA002387221A patent/CA2387221A1/en not_active Abandoned
Also Published As
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JP2003511508A (ja) | 2003-03-25 |
US6440206B1 (en) | 2002-08-27 |
CA2387221A1 (en) | 2001-04-12 |
WO2001025335A1 (en) | 2001-04-12 |
KR20020065890A (ko) | 2002-08-14 |
GB9923233D0 (en) | 1999-12-08 |
EP1218450A1 (en) | 2002-07-03 |
AU7659600A (en) | 2001-05-10 |
BR0014471A (pt) | 2002-06-11 |
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