Bis-propyl amine analog and composition

• US 20040152017A1
• Filed: 11/17/2003
• Published: 08/05/2004
• Est. Priority Date: 06/17/2002
• Status: Abandoned Application

• Current Assignee: Anthony A. Saglimbeni, Chris Philips, Ewell Cook, Mike Cunningham, Peter Miller, Rakesh Vig, Richard H. Selinfreund, Scott Gerger
• Original Assignee: Anthony A. Saglimbeni, Chris Philips, Ewell Cook, Mike Cunningham, Peter Miller, Rakesh Vig, Richard H. Selinfreund, Scott Gerger
• Inventors: Miller, Peter, Cook, Ewell, Vig, Rakesh, Selinfreund, Richard H., Philips, Chris, Cunningham, Mike, Saglimbeni, Anthony A., Gerger, Scott
• Application Number:
  US10/715,244
• Publication Number:
  US 20040152017A1
• Time in Patent Office: Days
• US Class Current: 430/270.15
• CPC Class Codes: C07D 279/18 [b, e]-condensed with two six-membered rings
• CPC Class Codes: C09B 21/00 Thiazine dyes
• CPC Class Codes: G11B 20/00086 Circuits for prevention of unauthorised reproduction or copying, e.g. piracy indicating unauthorised use of record carriers in general G11B23/28; scrambling for television signal recording H04N5/913; network architectures or network protocols for network security H04L63/00; cryptographic mechanisms or cryptographic arrangements for secret or secure communication H04L9/00
• CPC Class Codes: G11B 20/00094 involving measures which result in a restriction to authorised record carriers
• CPC Class Codes: G11B 20/00173 wherein the origin of the content is checked, e.g. determining whether the content has originally been retrieved from a legal disc copy or another trusted source
• CPC Class Codes: G11B 20/00608 wherein the material that the record carrier is made of is altered, e.g. adding reactive dyes that alter the optical properties of a disc after prolonged exposure to light or air
• CPC Class Codes: G11B 20/00927 wherein said defects or errors are generated on purpose, e.g. intended scratches
• CPC Class Codes: G11B 23/282 Limited play
• CPC Class Codes: G11B 7/244 comprising organic materials only
• CPC Class Codes: G11B 7/245 containing a polymeric component
• CPC Class Codes: G11B 7/2534 polycarbonates [PC]
• CPC Class Codes: G11B 7/258 of reflective layers

Abstract

Copy-protected optical medium utilizing a composition comprising a transient optical state change security materials capable of changing optical state when exposed to a wavelength of about 630 nm to about 660 nm and an electron transfer agent.

Claims

1. A method for fabricating an optical medium readable by an optical reader, said method comprising the steps of:

(a) molding a substrate so as to have a first major surface with information pits and information lands thereon and a second major surface that is relatively planar;

(b) applying a transient optical state change security material capable of converting from a first optical state to a second optical state upon exposure to the laser of said optical reader to at least a position of said first major surface;

(c) applying a reflective material over the first major surface so as to cover said information pits and information lands;

wherein the transient optical state change security material comprises [7-(dipropylamino)phenothiazin-3-ylidene]dipropylamine.

2. [7-(dipropylamino)phenothiazin-3-ylidene]dipropylamine.

3. A compound of the formula:

4. A composition comprising:

a transient optical state change security material capable of existing in a first unactivated state and a second activated state on said first or second major surface, said transient optical state security material comprising a compound of formula I;

where R₆, R₇, R₈, and R₉ are alkylamino and R₁, R₂, R₃, R₄ and R₅ are selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, thioalkoxy, alkylamino, nitro, amino and halogen; and

X is selected from the group consisting of Cl, Br, I, Chlorate, Mesylate, Tosylate, triflate, ethoxylate, methoxylate and any other anion, and

an electron transfer agent.

5. The composition of claim 4 wherein the compound of formula I is [7-(dipropylamino)phenothiazin-3-ylidene]dipropyl-amine.

6. The composition of claim 4 wherein the electron transfer agent is selected from the group consisting of:

triethanol amine, diethanol amine, TMG, DMEA, DEMEA, TMED, EDTA, Bis-Tris, p-tolylimido diethanol, N-tert-butyldiethanol amine, 4-morpholine ethanol, 1,4-bis-2-hydroxyethyl piperazine, bicine, BES, 3-Pyrrolidino-1,2-propanediol, 1-Amino-3,3-diethoxypropane, (S)-3-tert-Butylamino-1,2-propanediol, DL-Isoproterenol sulfate dihydrate, N,N-Bis(2-hydroxyethyl)-3-methoxyaniline, 1,1′

-[[3-(Dimethylamino)propyl] imino]bis-2-propanol, Triethanolamine Ethoxylate, 2,2′

-(4-Methylphenylimino)diethanol, Triisopropanolamine, 2-[[2-[2-(dimethylamino)ethoxy]ethyl]methylamino] ethanol, Triethanolamine Hydrochloride, N-phenyldiethanolamine, 1-[N,N-Bis(2-hydroxyethyl) amino]-2-propanol, N-t-Butyldiethanolamine, N-Butyldiethanolamine, 3-Morpholino-1,2-propanediol, N,N-Bis(2-hydroxyethyl)ethylenediamine, 3-(Diethylamino)-1,2-propane-diol, 4-(3-hydroxypropyl)morpholine, N-Ethyldiethanolamine, 4-(2-Hydroxyethyl)-morpholine, N-Methyldiethanolamine, 3-morphonlino-1,2-propanediol, 3-diisopropyl-amino-1,2-propanediol, 3-(dimethylamino)-1,2-propanediol, 3-piperidino-1,2-propanediol, 3-(diethylamino)-1,2-propanediol, dropropizine.

7. The composition of claim 6 wherein the compound of formula I is [7-(dipropylamino)phenothiazin-3-ylidene]dipropyl-amine.

8. The composition of claim 4 further comprising a polymer.

9. The composition of claim 8 wherein the polymer is selected from the group consisting of:

polyHEMA and hydrolysed PVA.

10. The composition of claim 4 wherein the electron transfer agent is chemically linked to a polymeric structure.

11. The composition of claim 10 wherein the electron transfer agent-polymer has a molecular weight in the range of about 50-100 KD.

12. The composition of claim 11 wherein the electron transfer agent-polymer is soluble in methoxy propanol.

13. The composition of claim 10 wherein the electron transfer agent is chemically linked to the polymer via a bis(2-hydroxyethyl) amino functionality.

14. An optical medium comprising the compound [7-(dipropylamino)phenothiazin-3-ylidene]dipropyl-amine wherein the compound when applied to the optical medium it is detectable on said optical medium by an optical reader producing a wavelength of from about 630 nm to about 660 nm by a transient change in optical state from an initial optical state to a second optical state.

15. The optical medium of claim 14 wherein the compound is associated with an optical data deformation in a manner such that the read of the optical data deformation is different when the compound is in its initial optical state and its second optical state.

16. A method for authenticating an optical medium having a number of data deformations thereon, said method comprising the steps of:

(1) providing for a complementary data state onto a portion of said optical medium;

(2) detecting said complementary data state on said portion of said optical medium.

(3) authenticating said optical medium upon detection of said complementary data state on said portion of said optical medium;

wherein the complementary data state is produced using a transient optical state security material comprising [7-(dipropylamino)phenothiazin-3-ylidene]dipropyl-amine.

17. The method of claim 16 wherein said complementary data state entails a change from one valid data state to a different valid data state.

18. The method of claim 16 wherein said complementary data state entails a change from one erroneous data state to a different erroneous data state.

19. The method of claim 16 wherein said complementary data state entails a change from a valid data state to an erroneous data state.

20. The method of claim 16 wherein said complementary data state entails a change from an erroneous data state to a valid data state.

21. An optical disc comprising a compound of formula:

22. An optical disc comprising a composition having:

an electron transfer agent; and

a dye capable of being reduced by said electron transfer agent and activated by a wavelength of between about 630 nm to about 660 nm to convert from one optical state to a second optical state.

23. The optical disc of claim 22 wherein the electron transfer agent is selected from the group consisting of:

triethanol amine, diethanol amine, TMG, DMEA, DEMEA, TMED, EDTA, Bis-Tris, p-tolylimido di ethanol, N-tert-butyldiethanol amine, 4-morpho line ethanol, 1,4-bis-2-hydroxyethyl piperazine, bicine, BES, 3-Pyrrolidino-1,2-propanediol, 1-Amino-3,3-diethoxypropane, (S)-3-tert-Butylamino-1,2-propanediol, DL-Isoproterenol sulfate dihydrate, N,N-Bis(2-hydroxyethyl)-3-methoxyaniline, 1,1 ′

-[[3-(Dimethylamino)propyl] imino]bis-2-propanol, Triethanolamine Ethoxylate, 2,2′

-(4-Methylphenylimino)diethanol, Triisopropanolamine, 2-[[2-[2-(dimethylamino)ethoxy]ethyl]methylamino] ethanol, Triethanolamine Hydrochloride, N-phenyldiethanolamine, 1-[N,N-Bis(2-hydroxyethyl) amino]-2-propanol, N-t-Butyldiethanolamine, N-Butyldiethanolamine, 3-Morpholino-1,2-propanediol, N,N-Bis(2-hydroxyethyl)ethylenediamine, 3-(Diethylamino)-1,2-propane-diol, 4-(3-hydroxypropyl)morpholine, N-Ethyldiethanolamine, 4-(2-Hydroxyethyl)-morpholine, N-Methyldiethanolamine, 3-morphonlino-1,2-propanediol, 3-diisopropyl -amino-1,2-propanediol, 3-(dimethylamino)-1,2-propanediol, 3-piperidino-1,2-propanediol, 3-(diethylamino)-1,2-propanediol, dropropizine.

24. The optical disc of claim 22 wherein the molecules of said dye of said composition do not substantially aggregate together.