Surface modified adsorbents and use thereof

• US 20060086366A1
• Filed: 10/19/2005
• Published: 04/27/2006
• Est. Priority Date: 10/25/2004
• Status: Active Grant

• Current Assignee: Philip Morris USA Incorporated (Altria Group, Inc.)
• Original Assignee: Philip Morris USA Incorporated (Altria Group, Inc.)
• Inventors: Koller, Kent B., Xue, Lixin L.
• Granted Patent: US 7,832,412 B2
• Time in Patent Office: Days
• US Class Current: 131/202
• CPC Class Codes: A24D 3/14 of organic materials as additive of ion exchange materials A24D3/12
• CPC Class Codes: A24D 3/16 of inorganic materials
• CPC Class Codes: A24D 3/163 Carbon

Abstract

A surface-modified adsorbent comprises a reagent on a porous carrier. Preferred porous carriers are adsorbent carbons such as activated carbon, silica gels, aluminas, polyester resins, zeolites or zeolite-like materials, and mixtures thereof. An exemplary porous carrier is activated carbon comprising at least about 80% micropores and having an average particle size from about 6 mesh to about 300 mesh or an average particle size from about 0.2 mm to about 1 mm. The reagent preferably comprises 1 to 80% or 3 to 10% by weight of the adsorbent. Preferred reagents are 2-hydroxymethylpiperidine (2-HMP) or a 2-HMP analogues such as 2-(2-piperidine)ethanol (2-PE), N-piperidineethanol (N-PE), 2-(4-piperidine)ethanol (4-PE), 3-hydroxypiperidine hydrochloride (3-HPH), 4-hydroxypiperidine (4-HP), 3-N-piperidinyl-1,2-propanediol (3-PDP), 2-amino-1-phenylethanol (2-APE), 2-(N-anilino)ethanol (2-AE), and S-(−)2-phenylglycinol (2-PG). Surface modified adsorbents can be incorporated into cigarettes, preferably in an amount effective to reduce the concentration of one or more constituents of cigarette smoke.

Claims

1. A surface-modified adsorbent comprising a reagent incorporated in a porous carrier, wherein the reagent comprises 2-HMP or an analogue thereof.

2. The adsorbent of claim 1, wherein the porous carrier is selected from the group consisting of adsorbent carbon, activated carbon, silica gel, alumina, polyester resins, zeolites or zeolite-like materials, and mixtures thereof.

3. The adsorbent of claim 1, wherein the porous carrier is activated carbon (a) wherein the activated carbon comprises at least about 80% micropores;

(b) the activated carbon has an average particle size from about 6 mesh to about 300 mesh and/or (c) the activated carbon has an average particle size from about 0.2 mm to about 1 mm.

4. The adsorbent of claim 1, wherein the reagent comprises 1 to 80% or 3 to 10% by weight of the adsorbent.

5. The adsorbent of claim 1, wherein the reagent comprises 2-hydroxymethylpiperidine (2-HMP) or a 2-HMP analogue selected from the group consisting of 2-(2-piperidine)ethanol (2-PE), N-piperidineethanol (N-PE), 2-(4-piperidine)ethanol (4-PE), 3-hydroxypiperidine hydrochloride (3-HPH), 4-hydroxypiperidine (4-HP), 3-N-piperidinyl-1,2-propanediol (3-PDP), 2-amino-1-phenylethanol (2-APE), 2-(N-anilino)ethanol (2-AE), and S-(−

)2-phenylglycinol (2-PG).

6. The adsorbent of claim 1, wherein the reagent is incorporated in the carrier in an amount effective to reduce the concentration in mainstream tobacco smoke of one or more of carbon dioxide, hydrogen cyanide, ethane, 1,3-butadiene, isoprene, cyclohexadiene, 1,3-cyclohexadiene, methyl cyclopentadiene, formaldehyde, acetaldehyde, acrolein, acetone, diacetyl, methyl ethyl ketone, cyclopentanone, benzene, toluene, acrylonitrile, methyl furan, 2,5 dimethyl furan, hydrogen sulfide, methyl mecaptan, propene, propadiene, carbonyl sulfide, propionaldehyde, butyraldehyde, methanol, and 1-methylpyrrole.

7. The adsorbent of claim 1, wherein the reagent is incorporated in the carrier in an amount effective to reduce the concentration of hydrogen cyanide, 1,3-butadiene, formaldehyde, acetaldehyde, acrolein, diacetyl, acrylonitrile, and hydrogen sulfide in mainstream tobacco smoke by at least 90%.

8. A cigarette comprising a reagent incorporated in a porous carrier, wherein the reagent comprises 2-HMP or an analogue thereof.

9. The cigarette of claim 8, wherein the porous carrier is selected from the group consisting of adsorbent carbon, activated carbon, silica gel, alumina, polyester resins, zeolite or zeolite-like materials, and mixtures thereof.

10. The cigarette of claim 8, wherein the porous carrier comprises activated carbon having (a) at least about 80% micropores;

(b) an average particle size from about 6 mesh to about 300 mesh and/or (c) an average particle size from about 0.2 mm to about 1 mm.

11. The cigarette of claim 8, wherein the reagent comprises 1 to 80% or 3 to 10% by weight of the adsorbent.

12. The cigarette of claim 8, wherein the porous carrier comprises beads located in a filter component of the cigarette.

13. The cigarette of claim 8, wherein the reagent is incorporated in the carrier in an amount effective to reduce the concentration in mainstream tobacco smoke of one or more of carbon dioxide, hydrogen cyanide, ethane, 1,3-butadiene, isoprene, cyclohexadiene, 1,3-cyclohexadiene, methyl cyclopentadiene, formaldehyde, acetaldehyde, acrolein, acetone, diacetyl, methyl ethyl ketone, cyclopentanone, benzene, toluene, acrylonitrile, methyl furan, 2,5 dimethyl furan, hydrogen sulfide, methyl mecaptan, propene, propadiene, carbonyl sulfide, propionaldehyde, butyraldehyde, methanol, and 1-methylpyrrole.

14. The cigarette of claim 8, wherein the reagent is incorporated in the carrier in an amount effective to reduce the concentration of hydrogen cyanide, 1,3-butadiene, formaldehyde, acetaldehyde, acrolein, diacetyl, acrylonitrile, and hydrogen sulfide in mainstream tobacco smoke by at least 90%.

15. A cigarette filter including a surface-modified adsorbent, the surface modified adsorbent comprising a reagent incorporated in a porous carrier, wherein the reagent comprises 2-HMP or an analogue thereof.

16. The cigarette filter of claim 15, wherein the porous carrier is selected from the group consisting of adsorbent carbon, activated carbon, silica gel, alumina, polyester resins, zeolites or zeolite-like materials, and mixtures thereof.

17. The cigarette filter of claim 16, wherein the porous carrier is activated carbon (a) wherein the activated carbon comprises at least about 80% micropores;

(b) the activated carbon has an average particle size from about 6 mesh to about 300 mesh and/or (c) the activated carbon has an average particle size from about 0.2 mm to about 1 mm.

18. The cigarette filter of claim 15, wherein the reagent comprises 1 to 80% or 3 to 10% by weight of the adsorbent.

19. The cigarette filter of claim 15, wherein the reagent comprises 2-hydroxymethylpiperidine (2-HMP) or a 2-HMP analogue selected from the group consisting of 2-(2-piperidine)ethanol, N-piperidineethanol, 2-(4-piperidine)ethanol, 3-hydroxypiperidine hydrochloride, 4-hydroxypiperidine, 3-N-piperidinyl-1,2-propanediol, 2-amino-1-phenylethanol, 2-(N-anilino)ethanol, and S-(−

)2-phenylglycinol.

20. The cigarette filter of claim 15, wherein the reagent is present in an amount effective to reduce the concentration in mainstream tobacco smoke of one or more of carbon dioxide, hydrogen cyanide, ethane, 1,3-butadiene, isoprene, cyclohexadiene, 1,3-cyclohexadiene, methyl cyclopentadiene, formaldehyde, acetaldehyde, acrolein, acetone, diacetyl, methyl ethyl ketone, cyclopentanone, benzene, toluene, acrylonitrile, methyl furan, 2,5 dimethyl furan, hydrogen sulfide, methyl mecaptan, propene, propadiene, carbonyl sulfide, propionaldehyde, butyraldehyde, methanol, and 1-methylpyrrole.

21. The cigarette filter of claim 15, wherein the reagent is incorporated in the carrier in an amount effective to reduce the concentration of hydrogen cyanide, 1,3-butadiene, formaldehyde, acetaldehyde, acrolein, diacetyl, acrylonitrile, and hydrogen sulfide in mainstream tobacco smoke by at least 90%.

22. The cigarette filter of claim 15, wherein the filter comprises a plug-space-plug configuration and the surface-modified adsorbent is incorporated in the space between the plugs.