Reaction Schemes

A1 Starting Materials (Section 2.1)

  1. 3,3′- or 3,3′,5,5′-Substituted 4,4′-diaminodiphenyls (Section 2.1.1):
    Figure depicting a chemical reaction, where 3,3'- or 3,3'-5,5'-substituted 4,4'-diaminodiphenyls.
  2. Acetoacetic acid arylides (Section 2.1.2):
    Figure depicting the chemical reaction for acetoacetic acid arylides.
  3. 2-Naphthol, 2-hydroxy-3-naphthoic acid and Naphthol AS (Section 2.1.2.2):
    Figure depicting the chemical reactions for 2-Naphthol, 2-hydroxy-3-naphthoic acid and naphthol AS.

A2 Synthesis of Hydrazone Pigments (Section 2.2)

  1. Diazotization (Section 2.2.1):

    Preceding equilibria for the formation of XNO (XCl, Br, NO2, HSO4):

    Figure depicting the reactions for preceding equilibria for the formation of XNO (XCl, Br, NO2, HSO4).

    Diazotization (Ar: aromatic group):

    Figure depicting the chemical reactions for diazotization, where Ar stands for aromatic group.

    Side reaction in the presence of an excess of −OH:

    Figure depicting the side reaction in the presence of an excess of -OH.

    Decomposition (thermal):

    Figure depicting a chemical reaction for thermal decomposition.
  2. Coupling (RH = coupling component) (Section 2.2.2):
    Figure depicting an example of coupling reaction.

    Side reaction in the case of acid deficiency (esp. with weak amines):

    Figure depicting a side reaction in the case of acid deficiency to form diazoamino compound.

A3 Monohydrazone Yellow and Monohydrazone Orange Pigments (Section 2.3)

  1. Non-laked monohydrazone yellow and orange pigments:
    A chemical reaction depicting the formation of non-laked monohydrazone yellow and orange pigments.
  2. Monohydrazone yellow and orange pigment lakes (Section 2.3):
    Figure depicting the chemical reaction for the formation of monohydrazone yellow and orange pigment lakes.

A4 Dihydrazone Pigments (Section 2.4)

  1. Diarylide yellow pigments (Section 2.4.1):
    Figure depicting the chemical reaction for the formation of diarylide yellow pigments.
  2. Bisacetoacetarylide pigments (Section 2.4.2):
    Figure depicting the chemical reaction for the formation of bisacetoacetarylide pigments.
  3. Dihydrazonepyrazolone pigments (Section 2.4.3):
    Figure depicting the chemical reaction for the formation of dihydrazonepyrazolone pigments.

A5 ß-Naphthol Pigments (Section 2.5)

Figure depicting the chemical reaction for the formation of β-naphthol pigments.

A6 Naphthol AS Pigments (Section 2.6)

Figure depicting the chemical reaction for the formation of naphthol as AS pigments.

A7 Red Hydrazone Pigment Lakes (Section 2.7)

  1. ß-Naphthol pigment lakes (Section 2.7.1):
    Figure depicting the chemical reaction for the formation of β-Naphthol pigment lakes.
  2. BONA pigment lakes (Section 2.7.2):
    Figure depicting the chemical reaction for the formation of BONA pigment lakes.
  3. Naphthol AS pigment lakes (Section 2.7.3):
    Figure depicting the chemical reaction for the formation of naphthol AS pigment lakes
  4. Naphthalene sulfonic acid pigment lakes (Section 2.7.4):
    1. Coupling in the 1-position:
      Figure depicting the chemical reaction for the formation of naphthalene sulfonic acid pigment lakes by coupling in the 1-position.
    2. Coupling in the 7-position:
      Figure depicting the chemical reaction for the formation of naphthalene sulfonic acid pigment lakes by coupling in the 7-position.

A8 Benzimidazolone Pigments (Section 2.8)

Figure depicting the chemical reaction for the formation of benzimidazolone pigments.

A9 Dihydrazone Condensation Pigments (Section 2.9)

  1. Yellow pigments:

    Type 1:

    Figure depicting the chemical reaction for the formation of dihydrazone condensation pigments (yellow pigments: type 1).

    Type 2:

    Figure depicting the chemical reaction for the formation of dihydrazone condensation pigments (yellow pigments: type 2).
  2. Red pigments:
    Figure depicting the chemical reaction for the formation of dihydrazone condensation pigments (red pigments).

A10 Phthalocyanine Pigments (Section 3.1)

  1. Phthalonitrile process (Section 3.1.2.1):
    Figure depicting the chemical reaction for the formation of phthalocyanine pigments by phthalonitrile process.
  2. Phthalic anhydride/urea process (Section 3.1.2.2):
    Figure depicting the chemical reaction for the formation of phthalocyanine pigments by phthalic anhydride/urea process.

A11 Quinacridone Pigments (Section 3.2)

  1. Thermal ring closure (Section 3.2.1.1):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by thermal ring closure.
  2. Acidic ring closure (Section 3.2.1.2):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by acidic ring closure.
  3. Dihalo-terephthalic acid process (Section 3.2.1.3):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by dihalo-terephthalic acid process.
  4. Hydroquinone process (Section 3.2.1.4):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by hydroquinone process.
  5. Substituted quinacridone pigments (Section 3.2.1.5):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by substituted quinacridone pigments.
  6. Quinacridone quinone synthesis (Section 3.2.1.6):
    Figure depicting the chemical reaction for the formation of quinacridone pigments by quinacridone quinone synthesis.

A12 Perylene and Perinone Pigments (Section 3.4)

Naphthalene tetracarboxylic acid dianhydride:

Figure depicting the chemical reaction for the formation of perylene and perinone pigments.

A13 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5)

Figure depicting the chemical reaction for the formation of diketopyrrolopyrrole (DPP) pigments.

A14 Indigo, Thioindigo and Thiazine Indigo Pigments (Section 3.6)

  1. Thioindigo Pigments (Section 3.6.2)
    Figure depicting the chemical reaction for the formation of thioindigo pigments.
  2. Thiazine Indigo Pigments (Section 3.6.3)
    Figure depicting the chemical reaction for the formation of thiazine indigo pigments.

A15 Various Polycyclic Pigments Derived from Anthraquinone (Section 3.7)

Heterocyclic Anthraquinone Pigments (Section 3.7.3)

  1. Anthrapyrimidine (Section 3.7.3.1):
    Figure depicting the chemical reaction for anthrapyrimidine derived from anthraquinone.
  2. Indanthrone and Flavanthrone Pigments (Section 3.7.3.2):

Indanthrone:

Figure depicting the chemical reaction for indanthrone pigments derived from anthraquinone.

Flavanthrone:

Figure depicting the chemical reaction for flavanthrone pigments derived from anthraquinone.

Polycarbocyclic Anthraquinone Pigments (Section 3.7.4)

  1. Pyranthrone pigments (Section 3.7.4.1):
    Figure depicting the chemical reaction for the sythesis of pyranthrone pigments.
  2. Anthanthrone pigments (Section 3.7.4.2):
    Figure depicting the chemical reaction for the sythesis of anthanthrone pigments.
  3. Isoviolanthrone pigments (Section 3.7.4.3):
    Figure depicting the chemical reaction for the sythesis of isoviolanthrone pigments.
  4. Violanthrone Pigments (Section 3.7.4.4):
    Figure depicting the chemical reaction for the sythesis of violanthrone pigments.

A16 Dioxazine Pigments (Section 3.8)

Figure depicting the chemical reaction for the sythesis of dioxazine pigments.

A17 Quinophthalone Pigments (Section 3.9)

Figure depicting the chemical reaction for the sythesis of quinophthalone pigments by basic route and pigment synthesis.

A18 Isoindolinone and Isoindoline Pigments (Section 3.10)

  1. Azomethine type: tetrachloroisoindolinone pigments:
    Figure depicting the chemical reaction for the sythesis of azomethine type: tetrachloroisoindolinone pigments.

    Dainippon ink process:

    Figure depicting the chemical reaction for dainippon ink process.
  2. Methine type: isoindoline pigments:
    Figure depicting the chemical reaction for the sythesis of methine type: isoindoline pigments.

A19 Triarylcarbonium Pigments (Section 4.1)

  1. Inner salts of sulfonic acids (Section 4.1.1):
    Figure depicting the chemical reaction for the sythesis of inner salts of sulfonic acids.
  2. Dye salts with complex anions (Section 4.1.2):

Triphenylmethane and diphenylnaphthylmethane derivatives:

Figure depicting the chemical reaction for the sythesis of dye salts with complex anions.

Replacing DMA in the above scheme by N,N-diethylaniline and 1-N,N-ethylnaphthylamine, resp., affords Victoria Blue types:

figure

Phenylxanthene derivatives:

Figure depicting the chemical reaction for the sythesis of phenylxanthene derivatives.

Benzothiazolium derivatives:

Figure depicting the chemical reaction for the sythesis of benzothiazolium derivatives.

A20 Metal Complex Pigments (Section 4.2)

  1. Azo metal complexes (Section 4.2.1.1):

    Pigment Green 10:

    Figure depicting the chemical reaction for the sythesis of azo metal complexes.

    Complexes of azo-barbituric acid:

    Figure depicting the chemical reaction for the sythesis of complexes of azo-barbituric acid.
  2. Azomethine metal complexes (Section 4.2.1.2):

    From aromatic o-hydroxy aldehydes:

    Figure depicting the chemical reaction for the formation of azomethine metal complexes from aromatic o-hydroxy aldehydes.

    From diimino-butyric acid anilides:

    Figure depicting the chemical reaction for the formation of azomethine metal complexes from diimino-butyric acid anilides.

    From isoindolinones:

    Figure depicting the chemical reaction for the formation of azomethine metal complexes from isoindolinones.
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