Stabilizers for Photographic Silver Halide Emulsions

by Fischer, Gunther

• ISBN13: 9780306479052
• ISBN10: 0306479052
• Format: Hardcover
• Copyright: 2004-04-30
• Publisher: Plenum Pub Corp

Summary

This monograph will appeal both to industrial chemists and academics. The book is addressed to industrial chemists in the photographic industry as well as scientists in relevant research institutes, but also to any chemist or advanced student interested in this field. It is not, however, a textbook. Important organic-chemical (heterocyclic) and physicochemical topics (adsorption), for example, are given much attention. One main focus will be the chemistry of stabilizers (structure, relevant chemical and physicochemical properties, mechanism of action); the other main focus relates to the practical application of these substances for stabilization, sensitization, and other purposes. Especially valuable will be the analysis of the large patent output of the photographic industry.

Table of Contents

Foreword	xix
Preface	xxi
Abbreviations	xxiii
1. Emulsion Stability and Stabilization	1	(4)
1.1. Aging and Fog Formation	1	(1)
1.2. Stabilization and Fog Prevention	2	(3)
2. General Survey of Relevant Publications	5	(8)
2.1. Scope and Limitations	5	(1)
2.2. Reviews	5	(2)
2.3. Original Articles	7	(1)
2.4. Patents	7	(6)
3. Heterocyclic Stabilizers and Antifogging Agents	13	(68)
3.1. Introduction	13	(1)
3.2. Heterocyclic Structures	14	(18)
3.2.1. Tetraazaindenes and Related Compounds	14	(4)
3.2.1.1. History, Nomenclature	14	(2)
3.2.1.2. Photographic Studies	16	(1)
3.2.1.3. Patents	17	(1)
3.2.2. Other OH-NH-Acidic Compounds, Purines	18	(1)
3.2.2.1. Tautomeric Hydroxyazoles and -azines	18	(1)
3.2.2.2. Purines	19	(1)
3.2.3. NH-Acidic Compounds	19	(2)
3.2.3.1. General Aspects of Azoles	19	(2)
3.2.3.2. Benzotriazoles	21	(1)
3.2.3.3. Other Azoles	21	(1)
3.2.3.4. Binuclear Heterocyclic Systems	21	(1)
3.2.4. Nuclear-Nitrogen Substituted Compounds	21	(1)
3.2.5. Mercapto Compounds	22	(4)
3.2.5.1. General Aspects	22	(1)
3.2.5.2. General and Partial Structures	23	(1)
3.2.5.3. Tetrazoles	24	(1)
3.2.5.4. Other Mercaptoazoles	24	(2)
3.2.5.5. Azines	26	(1)
3.2.5.6. Binuclear Heterocyclic Systems	26	(1)
3.2.6. Thioxo Compounds	26	(1)
3.2.7. Thioethers	27	(1)
3.2.8. Quaternary Ammonium Salts	27	(1)
3.2.9. Various Heterocyclic Compounds	28	(4)
3.2.9.1 Amines and Hydroxylamines	28	(2)
3.2.9.2 Special Azole and Azine Derivatives	30	(1)
3.2.9.3 Binuclear Heterocyclic Systems	30	(1)
3.2.9.4 Sulfenamides and Sulfur-Containing Heterocyclic Systems	31	(1)
3.3. Relevant Physico-Chemical and Physical Properties	32	(23)
3.3.1. Influence on Photographic Properties	32	(1)
3.3.2. Acidity	32	(3)
3.3.2.1. Dissociation and its Determination	32	(2)
3.3.2.2. Azaindenes and Benzazoles	34	(1)
3.3.2.3. Mercaptoazoles	35	(1)
3.3.2.4. Tautomerism	35	(1)
3.3.3. Reactivity against Silver Ions	35	(4)
3.3.3.1. Silver-Salt Solubilities and their Determination	35	(1)
3.3.3.2. Silver Salts of Azaindenes, Purines, and Benzazoles	36	(1)
3.3.3.3. The Structures of TAI Silver Salts and Complexes	37	(1)
3.3.3.4. Silver Salts of Mercaptoazoles	38	(1)
3.3.3.5. Silver Complexes of Mercaptoazoles	38	(1)
3.3.3.6. Silver Complexes of Non-Acidic Compounds	38	(1)
3.3.3.7. Applications	38	(1)
3.3.4. Adsorption	39	(10)
3.3.4.1. The Adsorption State on Silver Halides	39	(3)
3.3.4.2. The Adsorption State on Silver and Silver Sulfide	42	(1)
3.3.4.3. The Determination of the Adsorbability	42	(2)
3.3.4.4. Quantitative Results	44	(1)
3.3.4.5. Parameters Influencing Adsorbability	44	(1)
3.3.4.6. Adsorption of Azaindenes and Azoles	45	(3)
3.3.4.7. Adsorption of Mercaptoazoles	48	(1)
3.3.4.8. Applications	49	(1)
3.3.5. Influence on Physical Grain Properties	49	(1)
3.3.5.1. Electronic and Ionic Properties	49	(1)
3.3.5.2. Influence on Electronic Properties	49	(1)
3.3.5.3. Influence on Ionic Properties	50	(1)
3.3.5.4. Other Measuring Methods	50	(1)
3.3.6. Redox Properties	50	(1)
3.3.7. Hydrophilicity and Hydrophobicity	51	(1)
3.3.8. Diffusion	52	(3)
3.3.8.1. Diffusibility and Diffusion Resistance	52	(1)
3.3.8.2. Determination of Diffusibility	52	(1)
3.3.8.3. Rendering Stabilizers Diffusion-Resistant	53	(1)
3.3.8.4. Diffusion Rates	53	(2)
3.4. Analytics, Toxicology, and Environmental Behavior	55	(2)
3.4.1. Analytics	55	(1)
3.4.2. Toxicology	56	(1)
3.4.3. Environmental Behavior	56	(1)
3.5. Mechanisms of Stabilization	57	(11)
3.5.1. The State of Discussion around 1970	57	(1)
3.5.1.1. Birr's Mechanistic Conclusions	57	(1)
3.5.1.2. Agreement and Contradiction	57	(1)
3.5.1.3. Subsequent Developments	58	(1)
3.5.2. Russian Studies on the Significance of Physico-Chemical Properties	59	(1)
3.5.2.1. Acidity, Silver-Bonding, and Adsorption	59	(1)
3.5.2.2. Dipole Properties	60	(1)
3.5.3. Interactions of Stabilizers with Metallic Silver (Ewa)	61	(1)
3.5.3.1. Influence on Metallic Silver Activity	61	(1)
3.5.3.2. Semiconductor Properties	61	(1)
3.5.3.3. Stabilizers and Colloidal Silver	62	(1)
3.5.4. The Oxidation Potential of Stabilizers (Tani)	62	(1)
3.5.5. The Complexation Theory (Cash)	63	(3)
3.5.5.1. The Silver Complex of Tetraazaindene	63	(2)
3.5.5.2. The Chelated Surface Complex	65	(1)
3.5.5.3. The Kinetic Analysis of Stabilization	65	(1)
3.5.5.4. The Molecular Mechanism of Stabilization	66	(1)
3.5.5.5. Discussion	66	(1)
3.5.6. Recent Developments: Interactions with Interstitial Silver Ions and Effects on Digestion	66	(2)
3.5.6.1. Bases	66	(1)
3.5.6.2. Interactions with Interstitial Silver Ions	67	(1)
3.5.6.3. Stabilization in Relation to Digestion	67	(1)
3.5.6.4. Further Contributions	67	(1)
3.6. Interactions of Stabilizers with Sensitization Processes	68	(11)
3.6.1. Main Topics	68	(1)
3.6.2. Stabilizers as Sulfur Sensitization Modifiers	68	(1)
3.6.3. Competitive Adsorption with Spectral Sensitizers	69	(1)
3.6.4. Potentiation	69	(1)
3.6.5. Supersensitization by Non-Acidic Compounds	70	(2)
3.6.5.1. Definition	70	(1)
3.6.5.2. Mechanisms	71	(1)
3.6.5.3. Photographic Studies	72	(1)
3.6.5.4. Applications	72	(1)
3.6.6. Chemical Sensitization and Supersensitization by Acidic Compounds	72	(7)
3.6.6.1. Sensitizing Effects of Classic Stabilizers (Tani)	72	(1)
3.6.6.2. Tani's Proposed Mechanism	73	(3)
3.6.6.3. The Insulation Theory of Supersensitization (Shapiro)	76	(1)
3.6.6.4. Further Experimental Contributions	77	(1)
3.6.6.5. Applications	78	(1)
3.7. Other Uses	79	(2)
3.7.1. Photography	79	(1)
3.7.2. Corrosion Inhibition	80	(1)
4. Phenolic Species	81	(22)
4.1. Introduction	81	(1)
4.2. Structures	82	(10)
4.2.1. General and Partial Structures	82	(1)
4.2.2. Monohydric Phenols	83	(1)
4.2.3. Pyrocatechols	83	(1)
4.2.4. Resorcinols	84	(1)
4.2.5. Hydroquinones	84	(4)
4.2.5.1. Alkyl Derivatives	84	(2)
4.2.5.2. Hydrophilic and Amino Derivatives	86	(1)
4.2.5.3. Other Derivatives	87	(1)
4.2.6. Trihydric Phenols	88	(1)
4.2.7. Monohydric Aminophenols	88	(1)
4.2.8. Non-Phenolic Antioxidants and ODS Compounds	89	(3)
4.2.8.1. Oxygen Containing Functionalities	89	(1)
4.2.8.2. Hydrazines and Related Compounds	89	(2)
4.2.8.3. Competing Couplers	91	(1)
4.3. Functions and Relevant Properties	92	(7)
4.3.1. Modes of Action	92	(1)
4.3.2. Mechanisms of Oxidized Developer Scavenging	93	(2)
4.3.3. Oxidation Potential, Reactivity, and Substance Stability	95	(3)
4.3.3.1. Oxidation Potentials	95	(1)
4.3.3.2. The Determination of the Scavenger Reactivity	95	(2)
4.3.3.3. Scavenger Stability	97	(1)
4.3.3.4. Influences of the Structure	97	(1)
4.3.3.5. Competition with Couplers	98	(1)
4.3.4. Diffusion Resistance and Dispersability	98	(1)
4.3.5. Further Properties	99	(1)
4.3.5.1. Physico-Chemical Properties	99	(1)
4.3.5.2. Toxicology and Environmental Behavior	99	(1)
4.4. Applications	99	(4)
4.4.1. Scavengers in Emulsion Layers and Non-Photosensitive Layers	99	(1)
4.4.2. Combinations of Phenolic and Related Compounds	100	(1)
4.4.3. Combinations with Other Additives	101	(1)
4.4.4. Phenols in Color Image Stabilization Processes	101	(1)
4.4.4.1. Color Image Stabilizers	101	(1)
4.4.4.2. ODS-Type Compounds as Color Image Stabilizers	101	(1)
4.4.4.3. Interactions of ODS with Color Image Stabilization Processes	102	(1)
4.4.5. Other Special Uses	102	(1)
5. Aliphatic and Non-Phenolic Aromatic Compounds	103	(24)
5.1. Introduction	103	(1)
5.2. Structures	103	(15)
5.2.1. Hydrocarbons and Halo Compounds	103	(2)
5.2.2. Compounds Bearing Oxygen Functionalities	105	(1)
5.2.2.1. Alkanols and Ethers	105	(1)
5.2.2.2. Carbonyl and Carboxyl Compounds	105	(1)
5.2.3. Nitrogen-Containing Species	106	(4)
5.2.3.1. Amines	106	(1)
5.2.3.2. Amino Acid and Carbamic Acid Derivatives	107	(1)
5.2.3.3. Quaternary Ammonium Salts	108	(1)
5.2.3.4. Other Nitrogen Functionalities	109	(1)
5.2.4. Phosphorus-Containing and Analogous Compounds	110	(1)
5.2.5. Sulfur-Containing Species	111	(7)
5.2.5.1. Mercaptanes, Thioethers, and Related Compounds	111	(2)
5.2.5.2. Di- and Polysulfides	113	(1)
5.2.5.3. Sulfur-Containing Amino Acid and Carbamic Acid Derivatives	114	(1)
5.2.5.4. Sulfur Oxygen Acid Derivatives and Related Compounds	115	(3)
5.3. Relevant Properties and Mechanisms	118	(6)
5.3.1. Formation of Silver Salts and Complexes	118	(2)
5.3.2. Transformations of Sulfur Compounds	120	(1)
5.3.3. Redox and Sulfur-Acceptor Properties	121	(2)
5.3.3.1. Oxidants	121	(1)
5.3.3.2. Sulfinic Acid Salts	122	(1)
5.3.4. Further Properties	123	(4)
5.3.4.1. Physico-Chemical Properties	123	(1)
5.3.4.2. Analytics and Toxicology	123	(1)
5.4. Other Photographic Uses	124	(3)
6. Miscellaneous Compounds and Methods	127	(16)
6.1. Species Containing Group VI Sulfur Analogs	127	(2)
6.1.1. Selenium Compounds	127	(1)
6.1.2. Tellurium Compounds	127	(2)
6.2. Methine Dyes	129	(1)
6.2.1. Blue Sensitizers	129	(1)
6.2.2. Other Methine Dyes	130	(1)
6.3. Polymers	130	(7)
6.3.1. Natural Polymers and Derivatives	130	(1)
6.3.2. Synthetic Polymers	131	(2)
6.3.2.1. Vinyl-Type Polymers	131	(1)
6.3.2.2. Acrylate-Type Polymers	132	(1)
6.3.2.3. Other Polymeric Species	133	(1)
6.3.3. Polymers Bearing Specific Stabilizer Moieties	133	(4)
6.3.3.1. Heterocyclic Stabilizer Species	133	(1)
6.3.3.2. Phenolic and Related Species	134	(2)
6.3.3.3. Syntheses of Polymer-Fixed Stabilizers	136	(1)
6.3.3.4. Fixing Stabilizers to Gelatin	136	(1)
6.4. Inorganic Compounds	137	(1)
6.4.1. Compounds of Subgroup Elements	137	(1)
6.4.2. Compounds of Main-Group Elements	138	(1)
6.5. Coordination Compounds of Organic Ligands	138	(2)
6.6. Other Stabilization Methods	140	(3)
6.6.1. Control of pH and pAg Values	140	(1)
6.6.2. Miscellaneous Methods	141	(2)
7. The Moment of Incorporating Stabilizers	143	(16)
7.1. Introduction	143	(1)
7.2. Precipitation and Physical Ripening	143	(4)
7.2.1. Grain Growth Inhibition	143	(1)
7.2.2. Grain Habit Modification	144	(3)
7.2.3. Stabilization and Fog Prevention	147	(1)
7.3 Digestion	147	(3)
7.3.1. Chemical Ripening Inhibition	147	(1)
7.3.2. Stabilization and Fog Prevention	148	(2)
7.4. Coating	150	(3)
7.4.1. Development Inhibition	150	(2)
7.4.2. Stabilization and Fog Prevention	152	(1)
7.5. Processing Solutions	153	(6)
7.5.1. Development Inhibition	153	(1)
7.5.2. Stabilizers (Tetraazaindenes)	154	(1)
7.5.3. Antifoggants	155	(4)
8. Methods of Incorporation	159	(6)
8.1. Solution	159	(1)
8.2. Dispersion	159	(2)
8.2.1. Liquid-Liquid Dispersion	159	(2)
8.2.2. Solid-Liquid Dispersion	161	(1)
8.3. Special Methods of Diffusion-Resistant Incorporation	161	(1)
8.4. Other Incorporation Methods	162	(1)
8.5. Addition to Non-Photosensitive Layers	163	(2)
9. Masked Antifoggants and Stabilizers	165	(38)
9.1. General Structures and Effects	165	(3)
9.1.1. Structures	165	(1)
9.1.2. Trends of the Patent Applications	166	(1)
9.1.3. Modes of Action	167	(1)
9.2. Acyl Derivatives	168	(9)
9.2.1. Hydrolyzable Heterocyclic Thiolesters and N-Acyl Derivatives	168	(3)
9.2.2. Hydrolysis Rate and Photographic Activity of Acyl Derivatives	171	(2)
9.2.3. Derivatives Cleavable by Intramolecular Nucleophilic Displacement	173	(2)
9.2.4. Aliphatic and Aromatic Thiolesters	175	(2)
9.3. Alkyl and Aryl Derivatives	177	(12)
9.3.1. Survey	177	(1)
9.3.2. Derivatives Cleavable by β-Elimination	177	(1)
9.3.3. Hydroxybenzyl Derivatives	177	(2)
9.3.4. Heterocyclylmethyl Compounds	179	(3)
9.3.5. Other Functionalized Methyl Derivatives	182	(1)
9.3.6. Nitroaryl Derivatives	183	(2)
9.3.7. Other Masked Heterocyclic Antifoggants	185	(1)
9.3.8. Kinetics and Rate of Cleavage of Alkyl-Type Masked Antifoggants	186	(3)
9.4. Heterocyclic Disulfides	189	(2)
9.4.1. Di-(1-phenyl-5-tetrazolyl) Disulfides	189	(1)
9.4.2. Other Disulfides	190	(1)
9.5. Benzothiazolium Salts	191	(3)
9.5.1. Chemical Behavior	191	(1)
9.5.2. Photographic Applications	192	(1)
9.5.3. Use of Cleavage Products	193	(1)
9.6. Demasking by Cyclization and Ring Transformation	194	(1)
9.7. Salts and Adducts of Antifoggants	194	(3)
9.7.1. Ion Pairs formed with Inorganic and Organic Ions	194	(2)
9.7.2. Heavy Metal Salts	196	(1)
9.7.3. Adducts	197	(1)
9.8. Masked Phenolic and Non-Phenolic ODS Compounds	197	(1)
9.9. Special Conditions and Applications	197	(6)
9.9.1. Influences on Cleavage Kinetics	197	(3)
9.9.2. Incorporation	200	(1)
9.9.3. Application	200	(3)
10. Imagewise Release from DIR Compounds	203	(1)
10.1. Introduction	203	(1)
10.2. DIR Compounds without Color Coupler Properties	204	(1)
10.2.1. Release by Coupling Reactions at Active Methylene or Methine Groups	204	(2)
10.2.2. Release by Redox Reactions	206	(1)
10.2.2.1. DIR Hydroquinones and Other DIR Phenols	206	(2)
10.2.2.2. DIR Hydrazides	208	(1)
10.2.2.3. Other DIR Compounds	209	(2)
10.2.3. Specific Properties and Applications	211	(1)
10.3. DIR Couplers and Related Functional Couplers	212	(1)
10.3.1. Conventional DIR Couplers	212	(2)
10.3.2. Timing-DIR (DIAR) Couplers	214	(3)
10.3.3. Super-DIR Couplers	217	(1)
10.3.4. DIRR Couplers	217	(1)
10.3.5. ODSR Couplers	217	(2)
10.3.6. UDIR Couplers	219	(2)
11. Stabilization of Special Emulsions, Materials, Processes, and Properties	221	(1)
11.1. Materials Containing Little or No Gelatin	221	(1)
11.2. Special Emulsions	222	(1)
11.2.1. Emulsions having Specific Grain Size	222	(1)
11.2.2. Emulsions having Defined Crystal Habit	222	(1)
11.2.3. Emulsions having Special Grain Composition	223	(1)
11.2.3.1. Silver Chloride and Silver Chlorobromide Emulsions	223	(1)
11.2.3.2. High-Silver Iodide Emulsions	224	(1)
11.2.3.3. Core-Shell Emulsions	225	(1)
11.2.3.4. Converted Emulsions	225	(1)
11.2.4. High-Speed Emulsions	225	(1)
11.3. Special Materials	226	(1)
11.3.1. Reprographic and Related Materials	226	(1)
11.3.1.1. Lith Material	226	(1)
11.3.1.2. Material with Incorporated Contrast Promoters	227	(1)
11.3.1.3. High-Speed Negative-Type Material	228	(1)
11.3.1.4. High-Contrast Material for Low-pH Development	228	(1)
11.3.1.5. Material with Incorporated Inhibitors	229	(1)
11.3.1.6. Scan Films	229	(1)
11.3.1.7. Other Materials	230	(1)
11.3.2. Radiographic Materials	230	(1)
11.3.3. Scientific and Technological Materials	231	(1)
11.3.4. Other Black-and-White Materials	232	(1)
11.3.5. Color Materials	232	(2)
11.3.6. Direct-Positive Materials	234	(1)
11.4. Special Processes	235	(1)
11.5. Stabilization of Speed and Gradient	236	(3)
12. Application in the Presence of Other Constituents and Additives	239	(1)
12.1. Introduction	239	(1)
12.2. Support	239	(1)
12.2.1. Film	239	(1)
12.2.1.1. Cellulose Esters	239	(1)
12.2.1.2. Polyester	239	(1)
12.2.2. Paper	240	(1)
12.3. Gelatin	241	(1)
12.4. Speed-Increasing Additives	242	(1)
12.4.1. Chemical Sensitizers for Digestion	242	(1)
12.4.2. Development Accelerators	243	(1)
12.4.3. Spectral Sensitizers	244	(1)
12.5. Color Couplers	245	(2)
12.6. Developing Agents	247	(1)
12.7. Additives Influencing Physical and Mechanical Properties	248	(1)
12.7.1. Hardening Agents	248	(1)
12.7.2. Other Relevant Additives and Layers	249	(1)
12.8. Influences of Stabilizers and Development Inhibitors	250	(1)
13. Applications under Certain Environmental Conditions	251	(1)
13.1. Introduction	251	(1)
13.2. Physical Influences, Humidity, and Oxygen	251	(1)
13.2.1. Pressure	251	(1)
13.2.1.1. Causes and Effects	251	(1)
13.2.1.2. Agents Improving Pressure Resistance	252	(2)
13.2.1.3. Agents Preventing Pressure Desensitization or Pressure Fog	254	(1)
13.2.2. Temperature, Humidity, and Oxygen Concentration	255	(1)
13.2.2.1. Test Conditions	255	(1)
13.2.2.2. Temperature	256	(1)
13.2.2.3. Humidity	256	(2)
13.2.2.4. Temperature and Humidity	258	(2)
13.2.2.5. Oxygen, Inert Gases, and Vacuum	260	(1)
13.2.3. Light and Ionizing Radiation	260	(1)
13.3. Microorganisms	261	(2)
13.4. Chemical Agents	263	(1)
13.4.1. Influences of Packaging	263	(1)
13.4.2. Formaldehyde	264	(2)
13.4.3. Other Gases and Vapors	266	(1)
13.4.4. Nonvolatile Species	267	(1)
13.5. Influences of Processing	268	(1)
13.5.1. High-Temperature, Rapid, and Machine Processing	268	(1)
13.5.1.1. General Conditions, Reports	268	(1)
13.5.1.2. Patents	269	(3)
13.5.1.3. Processing of Special Materials	272	(1)
13.5.1.4. Exchangeable Processing	272	(1)
13.5.2. Processing under Safelight, Room-, and Daylight	273	(1)
13.5.2.1. Safelight	273	(1)
13.5.2.2. Room- and Daylight	274	(1)
13.5.3. Processing under Ecologically Safe Conditions	274	(1)
13.5.3.1. Benzyl Alcohol-Free Processing	274	(1)
13.5.3.2. Water-Saving Processing	275	(1)
13.5.3.3. Low-Replenishment Processing	276	(1)
13.5.4. Processing Stability	276	(1)
13.5.4.1. General Means	276	(1)
13.5.4.2. Processing Parameter Latitude	277	(1)
13.5.4.3. Processing Bath Quality	278	(3)
14. Applications to Prevent Special Kinds of Fog	281	(1)
14.1. Yellow Fog, Aerial Fog	281	(1)
14.1.1. Yellow Fog	281	(1)
14.1.2. Aerial Fog	282	(1)
14.2. Bleach Fog	282	(1)
14.3. Contact Fog	283	(1)
14.4. Other Kinds of Fog and Defects	283	(2)
15. Other Special Use	285	(1)
15.1. Stabilization of the Latent Image	285	(4)
15.2. Spot Prevention	289	(2)
15.3. Antibronzing	291	(1)
15.4. Toning	292	(5)
16. Concluding Remarks	297	(2)
Appendix: Toxicity of Stabilizers and Related Addenda	299	(2)
References	301	(1)
General Reviews of Stabilization and Other Photographic Topics	301	(3)
References to Chapters 1-16	304	(20)
Patents	324	(35)
Conference List	359	(2)
Indices	361	(1)
Author Index	361	(4)
Company and Institution Index	365	(2)
Subject Index	367