Granted Patent B2

US 12,404,233 · App. 17/786,765 · Granted Sep 2, 2025

Inventors: Eriko Sato (Tokushima, JP); Noriaki Shiina (Tokushima, JP); Kazuki Tsubokura (Tokushima, JP); Mifuyu Ueno (Tokushima, JP)

Assignee: OTSUKA CHEMICAL CO., LTD.

C07C247/10C07B2200/13

Abstract

Claims (16)

1. Crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising a peak of maximum intensity at an angle of diffraction (2θ) of 6.9±0.2°.

2. The crystals according to claim 1 , wherein the crystals have a melting point of 151° C. or more.

3. Crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising characteristic peaks at least at angles of diffraction (2θ) of 6.9±0.2°, 14.5±0.2°, 15.5±0.2°, 19.1±0.2°, 23.4±0.2°, 24.1±0.2°, 27.9±0.2° and 28.8±0.2°.

4. Crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising a peak of maximum intensity at an angle of diffraction (2θ) of 11.4±0.2° and/or 25.2±0.2°.

5. The crystals according to claim 4 , wherein the crystals have a melting point of 151° C. or more.

6. Crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising characteristic peaks at least at angles of diffraction (2θ) of 11.2±0.2°, 11.4±0.2°, 13.5±0.2°, 15.5±0.2°, 15.8±0.2°, 16.3±0.2°, 18.4±0.2°, 21.6±0.2°, 22.0±0.2°, 25.2±0.2° and 26.3±0.2°.

7. Crystals comprising crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising a peak of maximum intensity at an angle of diffraction (2θ) of 6.9±0.2° and crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising a peak of maximum intensity at an angle of diffraction (2θ) of 11.4±0.2° and/or 25.2±0.2°.

8. The crystals according to claim 7 , wherein a ratio of the intensity of the peak at an angle of diffraction (2θ) of 11.4±0.2° to that of the peak at an angle of diffraction (2θ) of 6.9±0.2° is 1:99 to 10:90.

9. Crystals comprising crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising characteristic peaks at least at angles of diffraction (2θ) of 6.9±0.2°, 14.5±0.2°, 15.5±0.2°, 19.1±0.2°, 23.4±0.2°, 24.1±0.2°, 27.9±0.2° and 28.8±0.2° and crystals of 3-hydroxy-N′-(1,3-dimethylbutylidene)-2-naphthoic acid hydrazide having an X-ray powder diffraction pattern comprising characteristic peaks at least at angles of diffraction (2θ) of 11.2±0.2°, 11.4±0.2°, 13.5±0.2°, 15.5±0.2°, 15.8±0.2°, 16.3±0.2°, 18.4±0.2°, 21.6±0.2°, 22.0±0.2°, 25.2±0.2° and 26.3±0.2°.

10. The crystals according to claim 9 , wherein a ratio of the intensity of the peak at an angle of diffraction (2θ) of 11.4±0.2° to that of the peak at an angle of diffraction (2θ) of 6.9±0.2° is 1:99 to 10:90.

11. A rubber additive comprising the crystals according to claim 1 .

12. A rubber additive comprising the crystals according to claim 4 .

13. A rubber composition comprising the rubber additive according to claim 11 .

14. A rubber composition comprising the rubber additive according to claim 12 .

15. A tire comprising the rubber composition according to claim 13 .

16. A tire comprising the rubber composition according to claim 14 .

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (21)