Additives to prevent degradation of cyclic alkene derivatives

• US 7,883,639 B2
• Filed: 09/12/2006
• Issued: 02/08/2011
• Est. Priority Date: 09/12/2005
• Status: Expired due to Fees

• 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 DAVID
• Application Number:
  US11/519,524
• Publication Number:
  US 20070057234A1
• Time in Patent Office: 1,610 Days
• Field of Search: 443/12, 444/42, 444/43, 444/45, 252/182.29
• US Class Current: 252/182.29
• CPC Class Codes: C07C 13/64 with a bridged ring system
• 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

Abstract

A stabilized cyclic alkene composition comprising one or more cyclic alkenes, and at least one antioxidant compound having the formula (I),

wherein R¹ through R⁵ can each independently be H, OH, C₁-C₈ linear, branched, or cyclic alkyl, C₁-C₈ linear, branched, or cyclic alkoxy or substituted or unsubstituted aryl, and wherein the antioxidant compound is present in an amount between 1 ppm and 200 ppm, and wherein said composition is purged with at least one inert gas after said composition is introduced to a container intended for storage or shipping of said composition. A method for forming a layer of carbon-doped silicon oxide on a substrate, which uses the stabilized alkene composition and a silicon containing compound.

Claims

1. A stabilized cyclic alkene composition comprising:

one or more cyclic alkenes, and

at least one antioxidant compound of formula (I),

2. The composition of claim 1, wherein said gas is at least one gas selected from the group consisting of:

helium, nitrogen, carbon monoxide and carbon dioxide.

3. The composition of claim 1, wherein said antioxidant compound is at least one compound selected form the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tertbutylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, 1,2-dihydroxybenzene, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT), 1,3-dihydroxybenzene, hydroquinone, 3,4,5-trimethoxyphenol, 3-ethoxy-4-methylphenol, 4-propoxyphenol, 4-butoxyphenol, 2,4-dicyclohexyl-5-methylphenol, and 6-tert-butyl-1,2-dihydroxybenzene.

4. The composition of claim 3, wherein said antioxidant compound is at least one compound selected from the group consisting of:

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

5. The composition of claim 1, wherein said antioxidant composition is present in an amount between about 1 ppm to about 100 ppm.

6. The composition of claim 1, wherein said antioxidant composition is present in an amount between about 100 ppm to 200 ppm.

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

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer wherein 1≦

x≦

n/2, y is an integer wherein 0≦

y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

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

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

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

(2x+4)−

yR_y, where n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+4), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

10. The composition of claim 1, wherein said 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.

11. The composition of claim 1, wherein said 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-2norbornene, and 5-ethylidene-2-norbornene, and wherein said antioxidant compound is at least one compound selected from the group consisting of;

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

12. A method for stabilizing a cyclic alkene, the method comprising adding at least one antioxidant compound of formula (I),

13. The method of claim 12, wherein said gas is at least one gas selected from the group consisting of helium, nitrogen, carbon monoxide and carbon dioxide.

14. The method of claim 12, wherein said antioxidant compound is at least one compound selected form the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tertbutylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, 1,2-dihydroxybenzene, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT), 1,3-dihydroxybenzene, hydroquinone, 3,4,5-trimethoxyphenol, 3-ethoxy-4-methylphenol, 4-propoxyphenol, 4-butoxyphenol, 2,4-dicyclohexyl-5-methylphenol, and 6-tert-butyl-1,2-dihydroxybenzene.

15. The method of claim 14, wherein said antioxidant compound is at least one compound selected from the group consisting of:

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

16. The method of claim 12, wherein said cyclic alkene has the general formula C_nH_2n−

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer wherein 1≦

x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

17. The method of claim 12, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

18. The method of claim 12, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, where n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

(2x+4), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

19. The method of claim 12, wherein said 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.

20. The method of claim 12, wherein said 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, and wherein said antioxidant compound is at least one compound selected from the group consisting of 4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

21. A stabilized cyclic alkene composition consisting essentially of:

one or more cyclic alkenes, and

at least one antioxidant compound of formula (I),

22. The composition of claim 21 wherein said gas is at least one gas selected from the group consisting of:

nitrogen and carbon dioxide.

23. The composition of claim 21, wherein said antioxidant compound is at least one compound selected form the group consisting of phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tertbutylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, 1,2-dihydroxybenzene, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT), 1,3-dihydroxybenzene, hydroquinone, 3,4,5-trimethoxyphenol, 3-ethoxy-4-methylphenol, 4-propoxyphenol, 4-butoxyphenol, 2,4-dicyclohexyl-5-methylphenol, and 6-tert-butyl-1,2-dihydroxybenzene.

24. The composition of claim 23, wherein said antioxidant compound is at least one compound selected from the group consisting of:

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

25. The composition of claim 21, wherein said antioxidant composition is present in an amount between about 1 ppm to about 100 ppm.

26. The composition of claim 21, wherein said antioxidant composition is present in an amount between about 100 ppm to 200 ppm.

27. The composition of claim 21, wherein said cyclic alkene has the general formula C_nH_2n−

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer wherein 1≦

x≦

n/2, y is an integer wherein 0≦

y≦

2n−

2x, and R is at least one component selected from the group consisting of C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

28. The composition of claim 21, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

29. The composition of claim 21, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, where n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

y≦

2n−

(2x+4), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

30. A stabilized cyclic alkene composition comprising:

one or more cyclic alkenes, and

at least one antioxidant compound selected from the group consisting of 2-(benzyloxy)phenol, 4-benzyloxyphenol, 4-benzyl-2,6-di-tert-butylphenol, 2-(2-butenyl)phenol, 2-(4-methylbenzyl)phenol, and 2,4,6-tris-benzyloxyphenol,

wherein said composition is purged with at least one gas selected from the group consisting of;

helium, neon, argon, krypton, xenon, radon, nitrogen, carbon monoxide and carbon dioxide, after said composition is introduced to a container intended for storage or shipping of said composition.

31. A method of forming a layer of carbon-doped silicon oxide on a substrate, the method comprising the steps of:

providing a cyclic alkene composition, a first silicon containing compound, and a substrate; and

forming the layer of the carbon-doped silicon oxide on the substrate, wherein said cyclic alkene composition comprises;

one or more cyclic alkenes; and

at least one antioxidant compound of Formula (I);

32. The method of claim 31, further comprising the steps of:

providing said cyclic alkene composition in said first container, said first silicon containing compound in a second container, a film deposition tool, a film deposition chamber within said film deposition tool, and a stream of carrier gas to sweep said cyclic alkene composition and said first silicon containing compound through a connecting means into the film deposition chamber, wherein said substrate is disposed within said film deposition chamber of said film deposition tool;

connecting said first and second containers to said film deposition chamber within said film deposition tool;

introducing vapors of said cyclic alkene composition and said first silicon containing compound into said carrier gas stream; and

transporting said vapors of said cyclic alkene composition and said first silicon containing compound into said film deposition chamber.

33. The method of claim 31, wherein said cyclic alkene has the general formula C_nH_2n−

2x−

yR_y, wherein n is an integer from 4 to 18, x is an integer wherein 1≦

x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

2x, and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated, or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated, or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

34. The method of claim 31, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+2)−

yR_y, wherein n is an integer from 5 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

(2x+2), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

35. The method of claim 31, wherein said cyclic alkene has the general formula C_nH_2n−

(2x+4)−

yR_y, where n is an integer from 7 to 18, x is an integer wherein x≦

n/2, y is an integer wherein 0≦

Y≦

2n−

(2x+4), and R is at least one component selected from the group consisting of;

C₁-C₁₈ linear, branched, unsaturated or cyclic alkyl, C₁-C₁₈ linear, branched, unsaturated or cyclic alkoxy, substituted or unsubstituted aryl, or a substituted silicon containing substituent.

36. The method of claim 31, wherein said 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.

37. The method of claim 31, wherein said antioxidant compound is at least one compound selected form the group consisting of:

phenol, 4-methylphenol, 3-methylphenol, 2-methylphenol, 4-ethylphenol, 4-propylphenol, 4-isopropylphenol, 4-butylphenol, 4-sec-butylphenol, 4-iso-butylphenol, 4-tertbutylphenol, 4-methoxyphenol, 3-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 2-(1-methylbutyl)phenol, 2-tert-butyl-6-methylphenol, 1,2-dihydroxybenzene, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT), 1,3-dihydroxybenzene, hydroquinone, 3,4,5-trimethoxyphenol, 3-ethoxy-4-methylphenol, 4-propoxyphenol, 4-butoxyphenol, 2,4-dicyclohexyl-5-methylphenol, and 6-tert-butyl-1,2-dihydroxybenzene.

38. The method of claim 37, wherein said antioxidant compound is at least one compound selected from the group consisting of:

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

39. The method of claim 31, wherein said 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-2norbornene, and 5-ethylidene-2-norbornene, and wherein said antioxidant compound is at least one compound selected from the group consisting of;

4-methoxyphenol, 1,2-dihydroxybenzene, 6-tert-butyl-1,2-dihydroxybenzene, and 2,6-di-tert-butyl-4-methylphenol.

40. The method of claim 31, further comprising providing a second silicon containing compound different from the first silicon containing compound.