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Polymers and other groups attached to pigment and subsequent reactions

A technology of polymers and pigments, which is applied in the treatment of dyed high-molecular organic compounds, dyed low-molecular organic compounds, and applications. It can solve the problems of carbon black lacking functional groups, difficult polymers and acetylene black surface grafting, etc.

Inactive Publication Date: 2003-03-05
CABOT CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods are not easy to surface graft polymers and acetylene black on the furnace, because these carbon blacks usually lack specific functional groups

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-11

[0043] Reaction Scheme 1 shows the sequence of the two-step reactions of Examples 1-11, wherein the first chemical group containing the electrophile (A) is first attached to the pigment surface, followed by the second chemical group containing the nucleophile (Z). Two chemical groups (polymer or other species) are added in the next step. The diagrams below are illustrative only and not limiting of the invention. Table 1 above lists examples of A-Z.

[0044] Reaction 1

[0045] Examples are given below for A = (2-sulfatoethyl)-sulfone (2SES), carboxylic acid and acyl azide, Z = alcohol and amine.

[0046] Equation 2 exemplarily describes the mechanism of 2SES.

[0047] Reaction 2

[0048] The (2-sulfoethyl)sulfone (2SES) functionality is an alkylating agent precursor and, therefore, it is an electrophile. Base-catalyzed elimination of the 2SES group leads to the formation of vinyl sulfones, which can then react with amines, alcohols, and thiols. Many useful compou...

Embodiment A

[0049] Embodiment A-D-2 Connection of SES

[0050] In the examples below, the 2SES group was attached to the pigment by diazotization of aminophenyl-(2-sulfatoethyl)sulfone (APSES) as shown in Reaction Scheme 3 below. Thus, the first chemical group can undergo subsequent reactions with several nucleophilic polymers. Reaction 3

[0051] APSES APSES-treated pigments

[0052] These modified pigments were prepared according to the following general procedure. The results are shown in Table 2 below.

[0053] Carbon black and APSES were mixed in distilled water in a ProcessAll mixer according to the specific levels listed in the table below. The mixture was heated at 50-55°C and mixed at 300 RPM for 10 minutes. To this was added 25% (by weight of ingredients) sodium nitrite (see Table 2 below for amounts) and an additional 50 ml of distilled water over 10-15 minutes. The resulting mixture was heated at 60°C for 2 hours. The contents were diluted by dilution with wate...

Embodiment 1-7

[0055] Examples 1-7: Reaction of APSES-treated pigments with polyamines (A=2SES; Z=amine):

[0056] These modified pigments were prepared according to the following general procedure.

[0057] A 10-15% solids dispersion of APSES-treated carbon black was added dropwise with vigorous stirring for 1 hour at room temperature to give polyethyleneimine (1-10 molar excess of polymer over electrophile functionality) in Solution in distilled water (the volume of which corresponds to the volume of the dispersion). The resulting mixture was then stirred for 18-48 hours. The crude product thus obtained was purified by membrane diafiltration with 10 volumes of 0.1 M NaOH followed by 10 volumes of distilled water. The resulting purified product had the following physical and printing properties.

[0058] Example

[0059] *Molar ratio = moles of polymer per mole of sodium present on the surface of carbon black; PEHA = pentaethylene hexamine; PEI() = polyethyleneimine (average MW...

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Abstract

A method of making a modified pigment by reacting a first chemical group and a second chemical group to form a pigment having attached a third chemical group. The first chemical group includes at least one nucleophile and the second chemical group includes at least one electrophile, or vice versa. Resulting modified pigments, and ink compositions containing such pigments, are also described.

Description

technical field [0001] The present invention relates to pigments and chemical groups attached to pigments. More specifically, the present invention relates to improved methods of attaching various types of chemical groups, such as polymers, to pigments. Background technique [0002] Methods for grafting polymers to the surface of carbon blacks, such as channel blacks, containing specific surface groups such as phenolic and carboxyl groups have long existed. However, these methods are not easy to surface graft polymers and acetylene black on the furnace, because these carbon blacks usually lack specific functional groups. The advantage of the method described here is that the polymer can be surface grafted to the surface of carbon black regardless of the original functional groups. [0003] It has now been found that pigments having polymers grafted onto the surface of the pigments provide improved performance when used in inkjet inks. These materials enable printed images...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B41J2/01B41M5/00C09B67/00C09B69/00C09B69/10C09C1/56C09C3/08C09C3/10C09D11/00
CPCC01P2006/12C09C3/10C09D11/322C01P2004/50C01P2004/51C01P2004/60C01P2006/60C09C3/08C09C1/56C09D11/324
Inventor 保罗·S·帕隆博柯蒂斯·E·亚当斯
Owner CABOT CORP
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