Glass articles with low-friction coatings

• US 9,775,775 B2
• Filed: 07/29/2015
• Issued: 10/03/2017
• Est. Priority Date: 02/28/2012
• Status: Active Grant

• Current Assignee: Corning Incorporated
• Original Assignee: Corning Incorporated
• Inventors: Fadeev, Andrei Gennadyevich, Chang, Theresa, Bookbinder, Dana Craig, Pal, Santona, Saha, Chandan Kumar, DeMartino, Steven Edward, Timmons, Christopher Lee, Peanasky, John Stephen
• Primary Examiner(s): Higgins, Gerard
• Application Number:
  US14/812,902
• Publication Number:
  US 20150329416A1
• Time in Patent Office: 797 Days
• Field of Search: 428 347, 428212, 428426, 428429, 428435, 2065243, 524600
• CPC Class Codes: A61J 1/1468 Containers characterised by specific material properties
• CPC Class Codes: B65D 23/0821 consisting mainly of polymeric materials B65D23/0828 takes precedence
• CPC Class Codes: C03C 17/005 Coating the outside
• CPC Class Codes: C03C 17/30 with silicon-containing compounds
• CPC Class Codes: C03C 17/32 with synthetic or natural resins C03C17/30 takes precedence
• CPC Class Codes: C03C 17/42 at least one coating of an organic material and at least one non-metal coating
• CPC Class Codes: C03C 21/002 to perform ion-exchange between alkali ions C03C21/005 takes precedence
• CPC Class Codes: C03C 2217/78 Coatings specially designed to be durable, e.g. scratch-resistant
• CPC Class Codes: C03C 2218/111 by dipping, immersion
• CPC Class Codes: Y10T 428/1321 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/24926 including ceramic, glass, porcelain or quartz layer
• CPC Class Codes: Y10T 428/24942 including components having same physical characteristic in differing degree
• CPC Class Codes: Y10T 428/265 1 mil or less
• CPC Class Codes: Y10T 428/31612 As silicone, silane or siloxane
• CPC Class Codes: Y10T 428/31623 Next to polyamide or polyimide

Abstract

Coated pharmaceutical packages are disclosed. In embodiments, a coated pharmaceutical package includes a glass body comprising a first surface. A low-friction coating may be positioned on at least a portion of the first surface of the glass body. The low-friction coating may include a polymer chemical composition. A light transmission through the coated pharmaceutical package may be greater than or equal to about 55% of a light transmission through an uncoated pharmaceutical package for wavelengths from about 400 nm to about 700 nm. The low-friction coating may have a mass loss of less than about 5% of its mass when heated from a temperature of 150° C. to 350° C. at a ramp rate of about 10° C./minute.

Claims

1. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from a borosilicate glass composition and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising;

a polymer selected from the group consisting of polyimides, fluoropolymers, silsesquioxane-based polymers, and silicone resins; and

a coupling agent layer disposed between the polymer and the first surface of the glass body,

wherein the coefficient of friction of the portion of the coated pharmaceutical package with the low-friction coating is at least 20% less than a coefficient of friction of a surface of an uncoated pharmaceutical package formed from the same glass composition.

2. The coated pharmaceutical package of claim 1, wherein a thickness of the low friction coating is less than or equal to 1 μ

m.

3. The coated pharmaceutical package of claim 1, wherein a thickness of the low friction coating is less than or equal to 100 nm.

4. The coated pharmaceutical package of claim 1, wherein

the coupling agent layer comprises a coupling agent;

and

wherein the low-friction coating comprises a polymer layer positioned over the coupling agent layer, the polymer layer comprising the polymer.

5. The coated pharmaceutical package of claim 4, wherein the coupling agent comprises at least one of:

a first silane, a hydrolysate thereof, or an oligomer thereof;

or

a chemical formed from the oligomerization of at least the first silane and a second silane, wherein the first silane and the second silane are different.

6. The coated pharmaceutical package of claim 5, wherein the first silane is an aromatic silane.

7. The coated pharmaceutical package of claim 1, wherein the coupling agent layer comprises a silsesquioxane comprising an aromatic moiety and an amine moiety.

8. The coated pharmaceutical package of claim 1, wherein the coupling agent layer comprises at least one of:

a mixture of a first silane and a second silane;

or

a chemical formed from the oligomerization of at least the first silane and the second silane, wherein the first silane and the second silane are different.

9. The coated pharmaceutical package of claim 8, wherein the first silane is an aromatic silane.

10. The coated pharmaceutical package of claim 1, wherein the polymer is a polyimide.

11. The coated pharmaceutical package of claim 1, wherein the coated pharmaceutical package is thermally stable at a temperature of at least about 260°

C. for 30 minutes.

12. The coated pharmaceutical package of claim 1, wherein the glass body comprises ion-exchanged glass.

13. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising;

a polymer selected from the group consisting of polyimides, fluoropolymers, silsesquioxane-based polymers, and silicone resins; and

a coupling agent comprising at least one of;

a first silane, a hydrolysate thereof, or an oligomer thereof, wherein the first silane is an aromatic silane;

or

a chemical formed from the oligomerization of at least the first silane and a second silane,

wherein;

the first silane and the second silane are different;

a light transmission through the coated pharmaceutical package is greater than or equal to about 55% of a light transmission through an uncoated pharmaceutical package for wavelengths from about 400 nm to about 700 nm; and

the low-friction coating has a mass loss of less than about 5% of its mass when heated from a temperature of 150°

C. to 350°

C. at a ramp rate of about 10°

C./minute.

14. The coated pharmaceutical package of claim 13, wherein a thickness of the low friction coating is less than or equal to 1 μ

m.

15. The coated pharmaceutical package of claim 13, wherein a thickness of the low friction coating is less than or equal to 100 nm.

16. The coated pharmaceutical package of claim 13, wherein the low-friction coating comprises:

a coupling agent layer positioned on the first surface of the glass body, the coupling agent layer comprising the coupling agent; and

a polymer layer positioned over the coupling agent layer, the polymer layer comprising the polymer.

17. The coated pharmaceutical package of claim 13, wherein the first silane is selected from the group consisting of aminophenyl alkoxysilanes, aminophenyl acyloxysilanes, aminophenyl halosilanes, 3-(m-aminophenoxy)propyl alkoxysilanes, 3-(m-aminophenoxy)propyl acyloxysilanes, 3-(m-aminophenoxy)propyl halosilanes, N-phenylaminopropyl alkoxysilanes, N-phenylaminopropyl acyloxysilanes, N-phenylaminopropyl halosilanes, (chloromethyl)phenyl alkoxysilanes, (chloromethyl)phenyl acyloxysilanes, and (chloromethyl)phenyl halosilanes.

18. The coated pharmaceutical package of claim 13, wherein the coupling agent comprises at least one of:

a mixture of the first silane and the second silane, wherein the second silane is an aliphatic silane;

or

a chemical formed from the oligomerization of at least the first silane and the second silane.

19. The coated pharmaceutical package of claim 18, wherein a molar ratio of the first silane to the second silane is from about 0.1:

1 to about 10;

1.

20. The coated pharmaceutical package of claim 18, wherein the first silane is an aromatic alkoxysilane comprising at least one amine moiety and the second silane is an aliphatic alkoxysilane comprising at least one amine moiety.

21. The coated pharmaceutical package of claim 18, wherein the first silane is selected from the group consisting of aminophenyl alkoxysilanes, aminophenyl acyloxysilanes, aminophenyl halosilanes, 3-(m-aminophenoxy)propyl alkoxysilanes, 3-(m-aminophenoxy)propyl acyloxysilanes, 3-(m-aminophenoxy)propyl halosilanes, N-phenylaminopropyl alkoxysilanes, N-phenylaminopropyl acyloxysilanes, N-phenylaminopropyl halosilanes, (chloromethyl)phenyl alkoxysilanes, (chloromethyl)phenyl acyloxysilanes, (chloromethyl)phenyl halosilanes, hydrolysates thereof, and oligomers thereof, and the second silane is selected from the group consisting of aminophenyl alkoxysilanes, aminophenyl acyloxysilanes, aminophenyl halosilanes, 3-(m-aminophenoxy)propyl alkoxysilanes, 3-(m-aminophenoxy)propyl acyloxysilanes, 3-(m-aminophenoxy)propyl halosilanes, N-phenylaminopropyl alkoxysilanes, N-phenylaminopropyl acyloxysilanes, N-phenylaminopropyl halosilanes, (chloromethyl)phenyl alkoxysilanes, (chloromethyl)phenyl acyloxysilanes, (chloromethyl)phenyl halosilanes, hydrolysates thereof, and oligomers thereof.

22. The coated pharmaceutical package of claim 18, wherein the first silane comprises at least one amine moiety and the second silane comprises at least one amine moiety.

23. The coated pharmaceutical package of claim 18, wherein the first silane is aminophenyltrimethoxy silane and the second silane is 3-aminopropyltrimethoxy silane.

24. The coated pharmaceutical package of claim 13, wherein the polymer is a polyimide formed from the polymerization of:

at least one monomer comprising at least two amine moieties; and

at least one monomer comprising at least two anhydride moieties and having a benzophenone structure.

25. The coated pharmaceutical package of claim 24, wherein the at least one monomer comprises at least two anhydride moieties is benzophenone-3,3′

,4,4′

-tetracarboxylic dianhydride.

26. The coated pharmaceutical package of claim 13, wherein the polymer is a polyimide formed from the polymerization of at least:

a first monomer, the first monomer comprising at least two amine moieties;

a second monomer, the second monomer comprising at least two amine moieties; and

a third monomer, the third monomer comprising at least two anhydride moieties;

wherein the first monomer is different than the second monomer.

27. The coated pharmaceutical package of claim 13, wherein the glass body is formed from a borosilicate glass composition.

28. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from a borosilicate glass composition and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising a polymer, wherein;

a light transmission through the coated pharmaceutical package is greater than or equal to about 55% of a light transmission through an uncoated pharmaceutical package for wavelengths from about 400 nm to about 700 nm; and

the low-friction coating has a mass loss of less than about 5% of its mass when heated from a temperature of 150°

C. to 350°

C. at a ramp rate of about 10°

C./minute, wherein the polymer is a polyimide.

29. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from an alkali aluminosilicate glass having a Class HGA 1 hydrolytic resistance when tested according to the ISO 720-1985 testing standard and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising;

a polymer selected from the group consisting of polyimides, fluoropolymers, silsesquioxane-based polymers, and silicone resins; and

a coupling agent layer disposed between the polymer and the first surface of the glass body, wherein the coefficient of friction of the portion of the coated pharmaceutical package with the low-friction coating is at least 20% less than a coefficient of friction of a surface of an uncoated pharmaceutical package formed from the same glass composition.

30. The coated pharmaceutical package of claim 29, wherein a thickness of the low friction coating is less than or equal to 1 μ

m.

31. The coated pharmaceutical package of claim 29, wherein a thickness of the low friction coating is less than or equal to 100 nm.

32. The coated pharmaceutical package of claim 29, wherein the coupling agent layer comprises a coupling agent.

33. The coated pharmaceutical package of claim 32, wherein the

coupling agent layer is positioned on the first surface of the glass body, the coupling agent layer comprising the coupling agent;

and

a polymer layer positioned over the coupling agent layer, the polymer layer comprising the polymer.

34. The coated pharmaceutical package of claim 33, wherein the coupling agent comprises at least one of:

a first silane, a hydrolysate thereof, or an oligomer thereof;

or

a chemical formed from the oligomerization of at least the first silane and a second silane, wherein the first silane and the second silane are different.

35. The coated pharmaceutical package of claim 34, wherein the first silane is an aromatic silane.

36. The coated pharmaceutical package of claim 32, wherein the coupling agent comprises a silsesquioxane comprising an aromatic moiety and an amine moiety.

37. The coated pharmaceutical package of claim 32, wherein the coupling agent comprises at least one of:

a mixture of a first silane and a second silane;

or

a chemical formed from the oligomerization of at least the first silane and the second silane, wherein the first silane and the second silane are different.

38. The coated pharmaceutical package of claim 37, wherein the first silane is an aromatic silane.

39. The coated pharmaceutical package of claim 29, wherein the polymer is a polyimide.

40. The coated pharmaceutical package of claim 29, wherein the coated pharmaceutical package is thermally stable at a temperature of at least about 260°

C. for 30 minutes.

41. The coated pharmaceutical package of claim 29, wherein the glass body comprises ion-exchanged glass.

42. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from an alkali aluminosilicate glass having a Class HGA 1 hydrolytic resistance when tested according to the ISO 720-1985 testing standard and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising a polymer, wherein;

a light transmission through the coated pharmaceutical package is greater than or equal to about 55% of a light transmission through an uncoated pharmaceutical package for wavelengths from about 400 nm to about 700 nm; and

the low-friction coating has a mass loss of less than about 5% of its mass when heated from a temperature of 150°

C. to 350°

C. at a ramp rate of about 10°

C./minute, wherein the polymer is a polyimide.

43. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from a borosilicate glass composition and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising a polyimide.

44. A coated pharmaceutical package comprising:

a glass body comprising a first surface and a second surface opposite the first surface, wherein the glass body is a glass container formed from an alkali aluminosilicate glass having a Class HGA 1 hydrolytic resistance when tested according to the ISO 720-1985 testing standard and the first surface is an exterior surface of the glass container; and

a low-friction coating positioned on at least a portion of the first surface of the glass body, the low-friction coating comprising a polyimide.