Additives to prevent degradation of cyclic alkene derivatives

• US 7,985,350 B2
• Filed: 12/21/2010
• Issued: 07/26/2011
• Est. Priority Date: 09/12/2005
• Status: Active Grant

• Current Assignee: Fujifilm Electronic Materials USA Incorporated (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Electronic Materials USA Incorporated (Fujifilm Holdings Corporation)
• Inventors: Chagolla, John L., Teff, Daniel J.
• Primary Examiner(s): Anthony; Joseph D
• Application Number:
  US12/974,090
• Publication Number:
  US 20110091651A1
• Time in Patent Office: 217 Days
• Field of Search: 443/12, 444/42, 444/43, 444/45, 44/6, 252/182.29
• US Class Current: 252/182.29
• CPC Class Codes: C07C 13/20 with a cyclohexene ring
• CPC Class Codes: C07C 13/21 Menthadienes
• CPC Class Codes: C07C 13/23 with a cyclohexadiene ring
• CPC Class Codes: C07C 13/39 with a bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C07C 13/42 with a bicycloheptene ring structure
• CPC Class Codes: C07C 13/43 substituted by unsaturated acyclic hydrocarbon
• CPC Class Codes: C07C 13/61 with a bridged indene ring, e.g. dicyclopentadiene
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2602/42 the bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C07C 2603/68 Dicyclopentadienes; Hydrogenated dicyclopentadienes
• CPC Class Codes: C07C 39/04 Phenol
• CPC Class Codes: C07C 39/06 Alkylated phenols
• CPC Class Codes: C07C 7/20 Use of additives, e.g. for stabilisation
• CPC Class Codes: C09K 15/08 containing a phenol or quinone moiety
• CPC Class Codes: C23C 16/401 containing silicon
• CPC Class Codes: C23C 16/448 characterised by the method used for generating reactive gas streams, e.g. by evaporation or sublimation of precursor materials
• CPC Class Codes: H10K 71/15 characterised by the solvent used

Abstract

This disclosure relates to compositions that include (a) at least one substituted or unsubstituted cyclic alkene, and (b) an antioxidant composition including at least one compound of Formula (I):

R¹ through R⁴ in Formula (I) are described in the specification.

Claims

1. A composition, comprising:

(a) at least one substituted or unsubstituted cyclic alkene, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

2. The composition of claim 1, wherein one of R¹ through R⁴ is methyl, ethyl, methoxy, or ethoxy.

3. The composition of claim 2, wherein at least one of the remaining R¹ through R⁴ is H.

4. The composition of claim 2, wherein all of the remaining R¹ through R⁴ are H.

5. The composition of claim 1, wherein R² or R³ is methyl or methoxy.

6. The composition of claim 5, wherein at least one of the remaining R¹ through R⁴ are H.

7. The composition of claim 1, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

8. The composition of claim 1, wherein the antioxidant composition comprises 3-methoxy-1,2-dihydroxybenzene.

9. The composition of claim 1, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

10. The composition of claim 1, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

11. The composition of claim 1, wherein the composition comprises a cyclic alkene having the general formula C_nH_2n−

2x−

yR_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 4 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and 1≦

x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

2x, and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

12. The composition of claim 1, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 5 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

(2x+2), and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

13. The composition of claim 1, wherein the cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 7 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

(2x+4), each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent.

14. The composition of claim 1, wherein the cyclic alkene is at least one compound selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene.

15. A composition, consisting essentially of:

(a) at least one substituted or unsubstituted cyclic alkene having the general formula C_nH<sub>2n−

2x−

y</sub>R_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 4 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and 1≦

x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

2x, and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

16. The composition of claim 15, wherein one of R¹ through R⁴ is methyl, ethyl, methoxy, or ethoxy.

17. The composition of claim 16, wherein at least one of the remaining R¹ through R⁴ is H.

18. The composition of claim 16, wherein all of the remaining R¹ through R⁴ are H.

19. The composition of claim 15, wherein R² or R³ is methyl or methoxy.

20. The composition of claim 19, wherein at least one of the remaining R¹ through R⁴ are H.

21. The composition of claim 15, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

22. The composition of claim 15, wherein the antioxidant composition comprises 3-methoxy-1,2-dihydroxybenzene.

23. The composition of claim 15, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

24. The composition of claim 15, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

25. The composition of claim 15, wherein the cyclic alkene is at least one compound selected from the group consisting of dipentene, limonene, terpinolene, phellandrene, alpha-terpinene, and gamma-terpinene.

26. The composition of claim 15, wherein at least one of R¹ through R⁴ is not H, or if one of R¹ through R⁴ is t-butyl, at least one of the remaining R¹ through R⁴ is not H.

27. A composition, consisting essentially of:

(a) at least one substituted or unsubstituted cyclic alkene having the general formula C_nH<sub>2n−

(2x+2)−

y</sub>R_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 5 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

(2x+2), and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent, and

(b) an antioxidant composition comprising at least one compound of Formula (I),

28. The composition of claim 27, wherein one of R¹ through R⁴ is methyl, ethyl, methoxy, or ethoxy.

29. The composition of claim 27, wherein at least one of the remaining R¹ through R⁴ is H.

30. The composition of claim 28, wherein all of the remaining R¹ through R⁴ are H.

31. The composition of claim 27, wherein R² or R³ is methyl or methoxy.

32. The composition of claim 31, wherein at least one of the remaining R¹ through R⁴ are H.

33. The composition of claim 27, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

34. The composition of claim 27, wherein the antioxidant composition comprises 3-methoxy-1,2-dihydroxybenzene.

35. The composition of claim 27, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

36. The composition of claim 27, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

37. The composition of claim 27, wherein the cyclic alkene is at least one compound selected from the group consisting of alpha-pinene, 3-carene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene.

38. The composition of claim 27, wherein at least one of R¹ through R⁴ is not H, or if one of R¹ through R⁴ is t-butyl, at least one of the remaining R¹ through R⁴ is not H.

39. A composition, comprising:

(a) a cyclic alkene selected from the group consisting of dipentene, phellandrene, dicyclopentadiene, alpha-terpinene, gamma-terpinene, limonene, alpha-pinene, 3-carene, terpinolene, norbornene, norbornadiene, 5-vinyl-2-norbornene, and 5-ethylidene-2-norbornene, and

(b) an antioxidant composition comprising 4-methyl-1,2-dihydroxybenzene or 3-methoxy-1,2-dihydroxybenzene.

40. The composition of claim 39, wherein the antioxidant composition comprises 4-methyl-1,2-dihydroxybenzene.

41. The composition of claim 39, wherein the antioxidant composition is present in a concentration between about 1 ppm and about 200 ppm.

42. The composition of claim 39, wherein the antioxidant composition is present in a concentration between about 50 ppm and about 150 ppm.

43. A composition, comprising:

(a) a substituted or unsubstituted cyclic alkene having the general formula C_nH<sub>2n−

(2x+2)−

y</sub>R_y, in which n is the number of carbons in the primary cyclic structure and is an integer from 5 to 18, x is the number of unsaturated sites in the primary cyclic structure and is an integer and x≦

n/2, y is the number of substituents, R, on the primary cyclic structure and is an integer and 0≦

y≦

2n−

(2x+2), and each R independently is C₁-C₁₈ linear alkyl, C₃-C₁₈ branched alkyl, C₂-C₁₈ unsaturated alkyl, C₃-C₁₈ cyclic alkyl, C₁-C₁₈ linear alkoxy, C₃-C₁₈ branched alkoxy, C₂-C₁₈ unsaturated alkoxy, C₃-C₁₈ cyclic alkoxy, substituted or unsubstituted aryl, or substituted silicon containing substituent, and

(b) an antioxidant composition comprising at least one compound of Formula (I),