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Abstract 17

제1장 서론 19

제2장 이론적 배경 21

2-1. 안료 21

2-1-1. 안료의 정의 21

2-1-2. 안료의 색상 21

2-1-3. 안료의 역사 23

2-1-4. 안료의 용도 25

2-1-5. 안료의 종류 27

2-1-5-1. 유기 안료 27

2-1-5-2. 무기 안료 28

2-1-5-3. 레이크 안료 30

2-1-6. 안료 특성 32

2-1-7. 가공 안료 40

2-1-8. 안료의 규제 43

2-2. Diarylide pigment 46

2-2-1. Pigment Yellow 83 49

2-3. Isoindonoline pigment 49

2-3-1. Pigment Yellow 139 55

2-4. Benzimidazolone pigment 55

2-4-1. Pigment Yellow 180 60

2-5. 안료의 분산 62

2-5-1. 분산제 62

2-5-2. 유도체 66

2-5-3. 표면처리 68

2-6. Autocalve 71

참고문헌 73

제3장 Diarylide계 안료의 분산 유도체를 이용한 합성 및 분산 거동 79

3-1. 서론 79

3-2. 실험 81

3-2-1. 시약 및 측정 81

3-2-2. 합성 82

3-2-2-1. 디아조 수용액 82

3-2-2-2. 커플러 수용액 82

3-2-2-3. 커플링 반응 85

3-2-2-4. 결정화 공정 85

3-3. 결과 및 고찰 86

3-3-1. 구조 분석 86

3-3-2. 반응 온도 효과 88

3-3-3. 반응 pH 효과 91

3-3-4. 전구체 효과 91

3-3-5. 결정화 온도 효과 97

3-4. 상업화 가능성 101

3-6. 결론 106

참고문헌 107

제4장 Isoindoline계 안료의 분산 유도체 도입에 따른 합성 및 결정화 특성에 관한 연구 109

4-1. 서론 109

4-2. 실험 111

4-2-1. 시약 및 측정 111

4-2-2. 합성 112

4-2-2-1. 1,3-diiminoisoindoline의 합성 112

4-2-2-2. Isoindoline 유도체의 합성 113

4-2-2-3. Isoindoline 화합물의 합성 116

4-3. 결과 및 고찰 117

4-3-1. 구조 분석 117

4-3-2. 반응 온도 효과 117

4-3-3. 결정화 온도 효과 122

4-3-4. 결정화 시간 효과 122

4-3-5. Isoindoline 유도체 효과 126

4-4. 상업화 가능성 132

4-5. 결론 136

참고문헌 137

제5장 Benzimidazolone계 안료의 수열 합성 및 용매를 처리를 통한 결정화에 관한 연구 140

5-1. 서론 140

5-2. 실험 142

5-2-1. 시약 및 측정 142

5-2-2. Benzimidazolone 화합물의 합성 144

5-2-2-1. 디아조 수용액 144

5-2-2-2. 커플러 수용액 144

5-2-2-3. 커플링 반응 146

5-2-2-4. 결정화 공정 146

5-3. 결과 및 고찰 147

5-3-1. 구조 분석 147

5-3-2. 커플링 반응 온도 효과 150

5-3-3. 결정화 온도 효과 153

5-3-4. 용매별 결정화 효과 157

5-3-5. 용매량별 결정화 효과 161

5-5. 상업화 가능성 164

5-6. 결론 170

참고문헌 171

제6장 총괄 결론 174

List of Tables

Table 2-1. Commercially Available Diarylide Yellow Pigments 47

Table 2-2. Tetrachloroisoindolinone of Azo Methine Type Structure 53

Table 2-3. Isoindoline Pigments of Methine Type Structures 54

Table 2-4. Commercially Available Beznimidazolone Yellow and Orange Pigments 58

Table 2-5. Commercially Available Beznimidazolone Red and Brown Pigments 59

Table 3-1. Color Difference and Particle Size of Sample Synthesized by Coupling Reaction with dimethyl-5-aminoiso-phthalate 3 ㏖% and then Crystallized for 1 h at 120 ℃ 105

Table 4-1. FT-IR Data of Various Isoindoline Derivatives 119

Table 4-2. Color Difference and Zeta Potential of Isoindoline Compound Samples Crystallized at 120 ℃ for 1 h 121

Table 4-3. Color Difference of Isoindoline Compound Samples Synthesized at Crystallized for 1 h at Various Temperature 124

Table 4-4. Color Difference of Isoindoline Compound Samples Synthesized with Various Isoindoline Derivatives, and then Crystallized for 1 h at 120 ℃ 131

Table 4-5. Color Difference and Particle Size of Sample Synthesized by Coupling Reaction with Dimethyl-5-arninoiso-phthalate 3 ㏖%, then Crystallized for 1 h at 120 ℃ 135

Table 5-1. Color Difference of Benzimidazolone Compound Samples Prepared by Coupling Reaction and then Crystallized for 1h at Various Temperature 156

Table 5-2. Color Difference and Strength of Benzimidazolone Compound Samples after Treated at Various Solvent at 120 ℃ 160

Table 5-3. Turbiscan Data and Viscosity of Benzimidazolone Compound Samples after Treated at Various DMSO Amount at 120 ℃ 160

Table 5-4. Color Difference and Particle Size of Sample Prepared by Solvent-Treatment at 120 ℃ 169

List of Figures

Figure 2-1. The structure illustration of aluminume lake pigment yellow 104. 31

Figure 2-2. Mechanisms in the dispersion process. 38

Figure 2-3. Replaced pigment surface of air and water by the resin. 39

Figure 2-4. Inclined stack of pigment yellow 83 molecules. 48

Figure 2-5. Structure illustration of pigment yellow 83. 50

Figure 2-6. The common structure of isoindoline ring. 51

Figure 2-7. Illustrations of azomethine type and disazomethine type isoindoline pigment. 52

Figure 2-8. Structure illustration of pigment yellow 139. 56

Figure 2-9. The two commercially relevant coupling components for beznimidazolone pigments. 57

Figure 2-10. Structure illustration of pigment yellow 180. 61

Figure 2-11. Various type of polymer and copolymer at steric stablization. 63

Figure 2-12. Schemiatic ㏖ecular structure of dispersants. 64

Figure 2-13. Unstable state polymeric chains in the dispersion process. 65

Figure 2-14. Scharatic of imprwed dispersion of phtalocyanine by phthalocyanine derivative. 67

Figure 2-15. Illustration of electrical double layer in particle. 69

Figure 2-16. The two main forces acting on charged particles in a solution. 70

Figure 2-17. Schematic diagram of the stirred autoclave reactor. 72

Figure 3-1. Synthetic procedure of diarylide compound. 83

Figure 3-2. FT-IR spectrum data of diarylide compound sample prepared by coupling reaction. 87

Figure 3-3. Particle size distribution of diarylide compound samples prepared by coupler solution of various temperatures 89

Figure 3-4. Zeta potential and turbiscan result of diarylide compound prepared by coupler solution of various temperature. 90

Figure 3-5. Zeta potential and turbiscan result of diarylide compound samples prepared by coupling reaction in different pH from coupler solution. 93

Figure 3-6. Zeta potential and turbiscan results of diarylide compound samples prepared by coupling reaction at various kind of dispersing precursors 94

Figure 3-7. Particle size distributions of diarylide compound samples prepared by coupling reaction from various addition of dispersing precursors 95

Figure 3-8. Zeta potential and turbiscan result of diarylide compound samples prepared by coupling reaction at various addition of dispersing precursors. 96

Figure 3-9. FE-SEM pictures of diarylide compound samples prepared by coupling reaction at various crystallization temperatures 98

Figure 3-10. Zeta potential and turbiscan results of diarylide compound samples prepared by coupling reaction at various crystallization temperatures. 99

Figure 3-11. UV-Vis spectra of diarylide compound samples prepared by coupling reaction at various crystallization temperatures. 100

Figure 3-12. FE-SEM pictures of sample synthesized by coupling reaction with dimethyl-5-aminoiso-phthalate 3 ㏖% and then crystallized for 1 h at 120 ℃ 102

Figure 3-13. XRD patterns of sample synthesized by coupling reaction with dimethyl-5-aminoiso-phthalate 3 ㏖% and then crystallized for 1 h at 120 ℃ 103

Figure 3-14. Color test of sample synthesized by coupling reaction with dimethyl-5-aminoiso-phthalate 3 ㏖% and then crystallized for 1 h at 120 ℃ 104

Figure 4-1. Synthetic procedure of isoindoline compound. 114

Figure 4-2. TEM pictures of isoindoline compound samples synthesized for 30 min at (a) 0℃, (b) 20 ℃, (c) 40 ℃, and (d) 60 ℃, and then crystallized at 120 ℃ for 1 h 120

Figure 4-3. Zeta potential and average particle size of isoindoline compound samples crystallized for 1 h at various temperature. 123

Figure 4-4. Zeta potential and average particle size of isoindoline compound samples crystallized for various time at 120℃ 125

Figure 4-5. Zeta potential and average particle size of isoindoline compound samples synthesized with various isoindoline derivatives, and then crystallized for 1 h at 120 ℃ 128

Figure 4-6. Color changes (△E) of isoindoline compound samples synthesized with various isoindoline derivatives, and then crystallized for 1 h at 120℃ 129

Figure 4-7. UV-Vis spectra of isoindoline compound samples synthesized with various isoindoline derivatives, and then crystallized for 1 h at 120℃ 130

Figure 4-8. FE-SEM pictures of sample synthesized by coupling reaction with dimethyl-5-aminoiso-phthalate 3 ㏖%, then crystallized for 1 h at 120 ℃ 133

Figure 4-9. Color test of sample synthesized by coupling reaction with dimethyl-5-aminoiso-phthalate 3 ㏖%, then crystallized for 1 h at 120 ℃ 134

Figure 5-1. Synthetic procedure of benzimidazolone compound. 145

Figure 5-2. FT-IR spectrum of benzimidazolone compound sample prepared by coupling reaction. 148

Figure 5-3. XRD data of benzimidazolone compound sample prepared by coupling reaction at 80 ℃ for 1 h from coupler solution 149

Figure 5-4. Intensity ratio and average particle size of benzimidazolone compound samples synthesised at various coupling reaction temperatures. 151

Figure 5-5. Turbiscan data and color strength of benzimidazolone compound samples synthesised at various coupling reaction temperatures. 152

Figure 5-6. Intensity ratio and average particle size of benzimidazolone compound samples prepared by coupling reaction and then crystallized for 1 h at various temperatures. 154

Figure 5-7. Turbiscan data and color strength of benzimidazolone compound samples prepared by coupling reaction and then crystallized for 1 h at various temperatures. 155

Figure 5-8. FE-SEM and TEM images of benzimidazolone compound samples prepared by solvent-treatment with various solvents at 120 ℃ 158

Figure 5-9. Intensity ratio and turbiscan data of benzimidazolone compound samples prepared by solvent-treatment with various solvents at 120℃ 159

Figure 5-10. Intensity ratio and average particle size of benzimidazolone compound samples prepared by solvent-treatment with various DMSO, distilled water ratio at 120 ℃ 162

Figure 5-11. FE-SEM images of samples prepared by solvent-treatment at 120 ℃ 165

Figure 5-12. XRD patterns of sample prepared by solvent -treatment at 120 ℃ 166

Figure 5-13. Color test of samples prepared by solvent-treatment at 120 ℃ 167

Figure 5-14. Thermal stability of samples prepared by solvent-treatment at 120 ℃ 168

List of Schemes

Scheme 3-1. Schematic illustration of the mechanism for diarylide compound in the coupling reaction synthesis. 84

Scheme 4-1. The synthesis of 1,3-diiminoisoindoline and various isoindoline derivatives 115

초록보기

 The diarylide pigment yellow 83 (P.Y. 83), which is bright reddish yellow color with superior lightfastness and solvent resistance, has been used in the field of high grade printing inks and painting application. Isoindoline pigment yellow 139 (P.Y.139), which is reddish yellow with high thermal resistance, has been used in the field of high grade industrial paints including original automobile and automotive refinishes and metal deco of plastic. Also, benzimidazolone pigment yellow 180 (P.Y.180), which is a greenish yellow with high performance of heat resistance, solvent resistance, and acid and alkali resistance, has been widely used in the fields of ink, paint, plastics, toner, and color filter, etc.

In this study, diarylide sample was synthesized at various pH, reaction and crystallization temperature by the synthetic scheme applied the coupling reaction with diarylide precursors. Isoindoline sample was synthesized at various condition from 1, 3—diiminoisoindoline precursor with addition of isoindoline derivatives, and then crystallized at various conditions in autoclave. Finally benzimidazolone sample was synthesized at various coupling reaction temperature, and then it was crystallized at different temperature and solvent in autoclave.

The chemical and crystalline structure of sample were analyzed by means of FT IR spectrometer and X-ray diffraction. The color properties were analyzed by the means of color-difference meter and UV-Vis spectrometer. The shape and size of particles and dispersion stability were analyzed by the means of field emission scanning electron microscope and turbiscan.

The various compound pigments of vivid color were synthesized successfully by the control of several factors such as pH, coupler solution temperature, different composition and addition of dispersion precursor, and crystallization temperature in the process of coupling synthesis. Color of samples was selectively controlled and its dispersion was enhanced by the introduction of dispersive derivatives. Finally, desired properties were obtained by the use of suitable solvent under the crystallization process.

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