Surface modified adsorbents and use thereof

• US 7,832,412 B2
• Filed: 10/19/2005
• Issued: 11/16/2010
• 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.
• Primary Examiner(s): Wyrozebski; Kat
• Assistant Examiner(s): DODDS, SCOTT
• Application Number:
  US11/252,772
• Publication Number:
  US 20060086366A1
• Time in Patent Office: 1,854 Days
• Field of Search: 131/334, 131/207, 131/331, 131360-368, 502/400, 502/417
• US Class Current: 131/334
• 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. Preferred reagents are 2-hydroxymethylpiperidine (2-HMP) or a 2-HMP analogue. 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 smoking article comprising a surface-modified adsorbent comprising a reagent incorporated in a porous carrier, wherein the reagent comprises an analogue of 2-hydroxymethylpiperidine 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), in an amount effective to reduce constituents of mainstream tobacco smoke and ranging from 1 to 80% by weight of the adsorbent.

2. The smoking article 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 smoking article of claim 1, wherein the porous carrier is activated carbon wherein:

(a) the activated carbon comprises at least about 80% micropores; and

either (b) the activated carbon has an average particle size from about 6 mesh to about 300 mesh;

or (c) the activated carbon has an average particle size from about 0.2 mm to about 1 mm.

4. The smoking article 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-methyl pyrrole.

5. The smoking article 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%.

6. The smoking article of claim 1, wherein the reagent is present in an amount of 3 to 10% by weight of the adsorbent.

7. A cigarette comprising a reagent incorporated in a porous carrier, wherein the reagent comprises an analogue of 2-hydroxymethylpiperidine (2-HMP) selected from the group consisting of 2-(2-piperidine)ethanol (2-PE), N-peridineethanol (N-PE), 2-(4-N-piperidine)ethanol (4-PE), 3-hydroxypiperidine hydrochloride (3-HPH), 4-hydroxyeridine (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-phenylqlycinol (2-PG), in an amount effective to reduce constituents of mainstream tobacco smoke and ranging from 1 to 80% by weight of the adsorbent.

8. The cigarette of claim 7, 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.

9. The cigarette of claim 7, wherein the porous carrier comprises activated carbon having:

(a) at least about 80% micropores; and

either (b) an average particle size from about 6 mesh to about 300 mesh;

or (c) an average particle size from about 0.2 mm to about 1 mm.

10. The cigarette of claim 7, wherein the porous carrier comprises beads located in a filter component of the cigarette.

11. The cigarette of claim 7, 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-methyl pyrrole.

12. The cigarette of claim 7, 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%.

13. The cigarette of claim 7, wherein the reagent is present in an amount of 3 to 10% by weight of the adsorbent.

14. A cigarette filter including a surface-modified adsorbent, the surface modified adsorbent comprising a reagent incorporated in a porous carrier, wherein the reagent comprises an analogue of 2-hydroxymethylpiperidine 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-phenlethanol (2-APE), 2-(N-anilino)ethanol (2-AE), and S-(−

)2-phenylglycinol (2-PG), in an amount effective to reduce constituents of mainstream tobacco smoke and ranging from 1 to 80% by weight of the adsorbent.

15. The cigarette filter of claim 14, 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.

16. The cigarette filter of claim 15, wherein the porous carrier is activated carbon wherein:

(a) 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;

(c) the activated carbon has an average particle size from about 0.2 mm to about 1 mm;

or a combination of two or more of (a), (b), and (c).

17. The cigarette filter of claim 14, 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-methyl pyrrole.

18. The cigarette filter of claim 14, 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%.

19. The cigarette filter of claim 14, wherein the filter comprises a plug-space-plug configuration and the surface-modified adsorbent is incorporated in the space between the plugs.

20. The cigarette filter of claim 14, wherein the reagent is present in an amount of 3 to 10% by weight of the adsorbent.