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3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester coupling agent and synthetic method thereof

A technology of hydroxyl-terminated straight-chain alkane diol and naphthoic acid is applied in the field of a new type of diazonium flake coupling agent - 3-hydroxy-2-naphthoic acid diester and its synthesis, which can solve the problem of aging and darkening in bright areas, light Density quality deterioration, color tone is not bright and other problems, to achieve the effect of improving photosensitive performance, photosensitive speed, easy to use

Inactive Publication Date: 2014-04-23
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Different coupling agents have great influence on the color, photosensitivity, and stability of diazo flake dyes. Most of the existing coupling agents have disadvantages such as dull color tone, slow ammonia smoke development, and weak anti-exposure ability. After the film is exposed to light, the quality of optical density will gradually deteriorate, that is, the brown color in the dark area will be gradually bleached by ultraviolet light, and the bright area will also gradually age and darken. The good effect of the past, the service life is also affected
In order to solve these technical problems, many scientific and technological workers have conducted a lot of research and have not found an ideal solution.

Method used

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  • 3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester coupling agent and synthetic method thereof
  • 3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester coupling agent and synthetic method thereof
  • 3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester coupling agent and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 3-hydroxy-2-naphthoic acid (10 g, 53 mmol), ethylene glycol (1.65 g, 26.5 mmol) into 55 mL toluene, about 1 mL trifluoromethanesulfonic acid (about 10 mmol), 110-120°C Reflux and split water for 5 h. After most of the solvent was evaporated, it was cooled and filtered. The filter cake was washed with hot sodium bicarbonate solution, washed with water until neutral, dried, mixed with tetrahydrofuran and toluene, and recrystallized to obtain 9.2 g of light yellow powder with a melting point of 172-175 ° C and a purity of more than 98 %, yield 86%.

[0023] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 10.30(s, 2H), 8.54 (s, 2H), 7.82–7.80 (m, 2H), 7.71-7.69 (m, 2H), 7.54-7.50 (m, 2H), 7.35-7.28 (m, 4H), 4.86 ppm (s, 4H); 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) 164.21, 156.96, 139.83, 133.77, 129.92, 129.12, 128.17, 126.38, 124.74, 113.82, 111.74, 63.25. elemental analysis calcd (%) for C 24 h 18 o 6 : C 71.64, H 4.51; found: C 71.45, H 4.75. MS (EI, m / z) 402.41.

[0024]...

Embodiment 2

[0027] Add 3-hydroxy-2-naphthoic acid (10 g, 53 mmol), 1,3-propanediol (2.02 g, 26.5 mmol) into 55 mL of toluene, about 1 mL of trifluoromethanesulfonic acid (about 10 mmol), 110- Reflux at 120°C for 6 h. Evaporate most of the solvent, then cool and filter, wash the filter cake with hot sodium bicarbonate solution, wash with water until neutral, dry, mix and recrystallize with tetrahydrofuran and acetone to obtain 8.6 g of yellow powder, melting point 130-133 ° C, purity greater than 98% , yield 77.8%.

[0028] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 10.30(s, 2H), 8.54 (s, 2H), 7.82–7.80 (m, 2H), 7.71-7.69 (m, 2H), 7.54-7.50 (m, 2H), 7.35-7.28 (m, 4H), 4.35-4.21 ppm (m, 4H), 2.41-2.37 ppm (m, 2H); 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) 164.21, 156.96, 139.83, 133.77, 129.92, 129.12, 128.17, 126.38, 124.74, 113.82, 111.74, 61.15, 27.64. elemental analysis for calcd (%) 25 h 20 o 6 : C 72.10, H 4.84; found: C 72.13, H 4.81. MS (EI, m / z) 416.44.

[0029] Take 0.5 g 3-hydroxy-...

Embodiment 3

[0032] Add 3-hydroxy-2-naphthoic acid (10 g, 53 mmol), 1,4-butanediol (2.4 g, 26.5 mmol) into 40 mL of chlorobenzene, about 1 mL of p-toluenesulfonic acid (about 10 mmol), Reflux at 130-140°C and divide water for 7 hours. After most of the solvent was evaporated, it was cooled and filtered. The filter cake was washed with hot sodium bicarbonate solution, washed with water until neutral, dried, mixed with tetrahydrofuran, methanol and acetone, and recrystallized to obtain 7.4 g of bright yellow powder with a melting point of 152-154 °C and a purity of Greater than 98%, the yield is 64.7%.

[0033] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 10.30(s, 2H), 8.54 (s, 2H), 7.82–7.80 (m, 2H), 7.71-7.69 (m, 2H), 7.54-7.50 (m, 2H), 7.35-7.28 (m, 4H), 4.35-4.21 ppm (m, 4H), 1.86-1.83 ppm (m, 4H); 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) 164.21, 156.96, 139.83, 133.77, 129.92, 129.12, 128.17, 126.38, 124.74, 113.82, 111.74, 64.55, 25.14. elemental analysis for calcd (%) 26 h 22 o 6 : C 72.5...

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Abstract

The invention discloses novel 3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester and a synthetic method thereof, belonging to the organic synthesis field. The 3-hydroxyl-2-naphthoic acid (1,n-alkylene glycol) diester is shown as the description; the synthetic method comprises the steps of carrying out esterification reaction on 3-hydroxyl-2-naphthoic acid and hydroxyl-terminated straight-chain alkane glycol in the presence of a dehydrating agent. The novel diazo coupling agent is of a double-naphthalene structure, and therefore, the coupling agent has an electron donating effect and good stability. The novel diazo coupling agent has the advantages of obviously improving the photosensitive property, achieving high photosensitive speed up to 15-20 seconds, having capability of generating a pure brown image, having good stability and convenience in use without combination of other stabilizers and coupling agents.

Description

technical field [0001] The invention relates to a new type of diazo coupler-3-hydroxy-2-naphthoic acid (1,n-alkanediol) diester and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] With the development of science and technology and the continuous improvement of the level of processing and manufacturing, the application of diazo tablets is becoming more and more extensive. At the earliest, it was only used for printing and dyeing and duplication and copying of some drawings and graphics. It was later applied to the manufacture of circuit graphics, solder mask graphics and screens, as well as the aerospace, aviation, electronics and processing fields of the modern defense industry. Judging from the current development speed, it will have a broader application prospect. [0003] Different coupling agents have great influence on the color, photosensitivity, and stability of diazo flake dyes. Most of the existing coupling ag...

Claims

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Application Information

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IPC IPC(8): C07C69/94C07C67/08G03F7/016
CPCC07C67/08C07C69/94
Inventor 郭利兵周鸿燕左国强崔海燕刘鹏举刘铁良周庆祥侯益民
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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