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Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release DISPERSE SYSTEMS AND DISPERSANTS - Dispersants (Rudolf Heusch, Karl Reizlein) 5.1.2. Formaldehyde Condensation Products Table (4) summarizes important dispersants produced by condensation of aromatic compounds with formaldehyde. The following describes a typical production of a dispersant of this category. With suitable variations it can be applied to a number of products formed by condensation with formaldehyde [50-00-0]. [70] , [71] , [72] , [73] , [74] , [75] , [76] , [77] , [78] , [79] Naphthalene (200 parts) is reacted with 200 parts of 98 % sulfuric acid for 5 h at 160 – 165 °C in an iron tank. After the solution has been cooled to 80 °C, the mixture is diluted with 90 parts of water in a lead-lined stirring vessel. Then 107 parts of a 30 % formaldehyde solution are added and the mixture is stirred for 20 h at ca. 80 °C. Toward the end of this period, the mixture is gradually heated to 100 °C. Neutralization is carried out at 20 – 25 °C with ca. 165 – 180 parts of a 25 % ammonia solution. The neutralization product is then filtered and, if necessary, dried in a vacuum drum drier [80]. Numerous variations of this synthesis are possible, and a wide range of aromatic compounds and their derivatives can react with aldehydes, ketones, and compounds that eliminate aldehyde groups. The following three typical examples supplement those listed in Table (4): 1) Dispersants produced by condensation of aromatic sulfonic acids and benzyl chloride [100-44-7] or benzoin [119-53-9] [81] 2) Dispersants produced by condensation of various alkylarylsulfonic acids with a halogen arylsulfonic acid [82] 3) Dispersants produced by condensation of sulfonated phenols, 2-naphthols, etc. with formaldehyde and various nitrogen compounds [83] Finally, special processes have been developed for improving the quality of dispersants or for adapting them to special applications [57]. Thus, the following specific products can be prepared: Products with low sulfate content [84] Low-foam, alkali-resistant sulfomethylation products obtained from mono- and polynuclear phenols [85] Thermostable condensation products [86] Low-foam condensation products obtained from diphenyl derivatives [73] Ethoxylated and sulfated condensation products obtained from alkylphenols and formaldehyde [87] Thermostable sulfomethylation products [88] Phenol – formaldehyde condensation products containing sulfonic groups and having improved dispersive action [89] Products that have no reducing action on sensitive dyes Almost colorless sulfomethylation products that are also suitable for optical brighteners [85] , [90] Dispersants that do not stain fibers [87] , [91] Postcondensed products with improved dispersive properties [92] Phenol – formaldehyde – hydrogen sulfite condensation products that contain nitrogen and are low in alkali concentration Commercial polysulfonate products are listed as follows [69]. Condensed sulfonates: Avolan IS (Bayer); CHT dispersants SMS (CHT); Dispersant EB (PUC-FMC); Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release © Wiley-VCH. Weinheim. Germany. Page: 1

Formaldehyde Condensation Products

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  • Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic ReleaseDISPERSE SYSTEMS AND DISPERSANTS - Dispersants (Rudolf Heusch, Karl Reizlein)

    5.1.2. Formaldehyde Condensation Products

    Table (4) summarizes important dispersants produced by condensation of aromatic compounds with formaldehyde. The following describes a typical production of a dispersant of this category. With suitable variations it can be applied to a number of products formed by condensation with formaldehyde [50-00-0]. [70], [71], [72], [73], [74], [75], [76], [77], [78], [79]

    Naphthalene (200 parts) is reacted with 200 parts of 98% sulfuric acid for 5 h at 160165 C in an iron tank. After the solution has been cooled to 80 C, the mixture is diluted with 90 parts of water in a lead-lined stirring vessel. Then 107 parts of a 30% formaldehyde solution are added and the mixture is stirred for 20 h at ca. 80 C. Toward the end of this period, the mixture is gradually heated to 100 C. Neutralization is carried out at 2025 C with ca. 165180 parts of a 25% ammonia solution. The neutralization product is then filtered and, if necessary, dried in a vacuum drum drier [80].

    Numerous variations of this synthesis are possible, and a wide range of aromatic compounds and their derivatives can react with aldehydes, ketones, and compounds that eliminate aldehyde groups. The following three typical examples supplement those listed in Table (4):1) Dispersants produced by condensation of aromatic sulfonic acids and benzyl chloride [100-44-7] or

    benzoin [119-53-9] [81]2) Dispersants produced by condensation of various alkylarylsulfonic acids with a halogen arylsulfonic

    acid [82]3) Dispersants produced by condensation of sulfonated phenols, 2-naphthols, etc. with formaldehyde and

    various nitrogen compounds [83]Finally, special processes have been developed for improving the quality of dispersants or for adapting them to special applications [57]. Thus, the following specific products can be prepared:

    Products with low sulfate content [84]Low-foam, alkali-resistant sulfomethylation products obtained from mono- and polynuclear phenols [85]Thermostable condensation products [86]Low-foam condensation products obtained from diphenyl derivatives [73]Ethoxylated and sulfated condensation products obtained from alkylphenols and formaldehyde [87]Thermostable sulfomethylation products [88]Phenolformaldehyde condensation products containing sulfonic groups and having improved dispersive action [89]Products that have no reducing action on sensitive dyesAlmost colorless sulfomethylation products that are also suitable for optical brighteners [85], [90]Dispersants that do not stain fibers [87], [91]Postcondensed products with improved dispersive properties [92]Phenolformaldehydehydrogen sulfite condensation products that contain nitrogen and are low in alkali concentration

    Commercial polysulfonate products are listed as follows [69].Condensed sulfonates: Avolan IS (Bayer); CHT dispersants SMS (CHT); Dispersant EB (PUC-FMC);

    Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release Wiley-VCH. Weinheim. Germany.Page: 1

  • Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic ReleaseDISPERSE SYSTEMS AND DISPERSANTS - Dispersants (Rudolf Heusch, Karl Reizlein)

    Dupramin DS (AKZO); Dyapanol (Yorkshire); Irgasol DAM (Ciba-Geigy); Lyocol O, Lyocol RD, Lyogen PN (Sandoz); Matexil DA-AC (ICI); Osimol DPA (Grnau); Setamol WS (BASF); Solegal A, P (Hoechst).Liquids: Tamol NH, NNO, NOP (BASF); Tanede DPA (Tanatex); Texamol WS (ACNA); Vultamol (BASF); Wotamol WS (VEB Wolfen); Baykanol PQ, Baykanol LS, Dispersant SS, Dispersant 523 (Bayer); Melmeny (SKW Trostberg), Lissatan AC (ICI); Demol N (Bayer, Japan).

    These important dispersants find applications in the following fields [93]:1) Milling additives and dispersants for pigments and dyes2) Dispersants and plasticizers in the building industry3) Dispersants for polishing and abrasive powders4) Stabilizing agents for resin glue emulsions, e.g., Tamol NOP (BASF)5) Auxiliary agents in the emulsion polymerization of synthetic rubber6) Dispersants for fillers, pigments, and vulcanizing agents in natural and synthetic rubber latices7) Boiling-temperature degreasing agents to which Tamol N brands (BASF) have been added to improve

    the stability of the solution and increase its dirt-suspending power

    Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, 2002 Electronic Release Wiley-VCH. Weinheim. Germany.Page: 2