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.
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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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