Granted Patent
B2
US 12,702,631 · App. 19/230,165 · Granted Aug 11, 2026
Oral care compositions comprising hops beta acids and fluoride ions
Inventors:
Arif Ali Baig (Mason, OH); Tammy Baker (Cincinnati, OH); Aaron Reed Biesbrock (Maineville, OH); Samuel James St. John (Cincinnati, OH)
Assignee:
The Procter & Gamble Company
A61K8/27A61K8/20A61K8/21A61K8/24A61K8/35A61K8/362A61K8/365A61K8/44A61K8/731A61K8/8147A61K8/97A61K8/9789A61K36/3486A61Q11/00A61K2800/28A61K2800/30A61K2800/48A61K2800/74A61K2800/92
View Patent ↗
Loading inventors, assignments & file history…
Abstract
Oral care compositions with an anticaries or anticavity effect. Oral care compositions that have an extract from a species in the Humulus family and an anticaries drug, such as a fluoride ion source. Oral care compositions have fluoride and hops beta acid, such as from an extract from Humulus lupulus . Oral care compositions have a fluoride ion source and a hops beta acid derived from an extract of Humulus lupulus.
Claims (18)
1 . An oral care composition comprising:
(a) hops extract comprising hops beta acid and hops alpha acid, wherein the hops extract comprises greater than 0% to less than 5%, by weight of the hops extract, of the hops alpha acids, wherein the oral care composition comprises about 0.01% to about 10%, by weight of the composition, of the hops beta acid, and wherein the hops beta acid comprises only non-hydrogenated hops beta acids; and
(b) about 0.01% to about 10%, by weight of the composition, of fluoride, wherein the oral care composition has a pH of greater than 7.
2 . The oral care composition of claim 1 , further comprising about 10% to about 50%, by weight of the composition, of a calcium ion source.
3 . The oral care composition of claim 2 , further comprising about 1% to about 20%, by weight of the composition, of a buffering agent, wherein the buffering agent comprises a conjugate acid of the calcium ion source.
4 . The oral care composition of claim 3 , wherein the calcium ion source comprises calcium carbonate and the conjugate acid of the calcium ion source comprises a bicarbonate anion.
5 . The oral care composition of claim 1 , further comprising a calcium abrasive.
6 . The oral care composition of claim 5 , wherein the calcium abrasive comprises calcium carbonate.
7 . The oral care composition of claim 1 , wherein the composition is free of silica.
8 . The oral care composition of claim 1 , wherein the hops beta acid comprises lupulone, colupulone, adlupulone, or combinations thereof.
9 . The oral composition of claim 1 , wherein the fluoride is selected from the group consisting of sodium fluoride, sodium monofluorophosphate, amine fluoride, indium fluoride, and combinations thereof.
10 . The oral care composition of claim 1 , further comprising about 0.01% to about 10%, by weight of the composition, of an antibacterial agent comprising a metal ion source.
11 . The oral care composition of claim 10 , wherein the metal ion source comprises tin, zinc, or combinations thereof.
12 . The oral care composition of claim 10 , wherein the metal ion source comprises the tin, and the tin comprises stannous chloride.
13 . The oral care composition of claim 1 , further comprising potassium nitrate.
14 . The oral care composition of claim 1 , further comprising an amino acid.
15 . The oral care composition of claim 14 , wherein the amino acid comprises glycine, alanine, valine, isoleucine, tryptophan, phenylalanine, proline, methionine, leucine, serine, threonine, tyrosine, asparagine, glutamine, cysteine, citrulline, aspartic acid, glutamic acid, lysine, arginine, histidine, or combinations thereof.
16 . The oral care composition of claim 1 , further comprising about 0.01% to about 20%, by weight of the composition, of a thickening system, wherein the thickening system comprises polyacrylic acid, cellulose, a cellulose derivative, xanthan gum, a carrageenan, or combinations thereof.
Continuity (11)
Provisional Application
62994893
· Mar 26, 2020
Provisional Application
62985451
· Mar 5, 2020
Provisional Application
62972111
· Feb 10, 2020
Provisional Application
62972109
· Feb 10, 2020
Provisional Application
62943940
· Dec 5, 2019
Provisional Application
62907733
· Sep 30, 2019
Provisional Application
62907736
· Sep 30, 2019
Provisional Application
62907735
· Sep 30, 2019
Related Publication
20250295565A1
· Sep 25, 2025
References Cited (248)
US 2723217A
· Gershon
· 1955
[cited by applicant]
US 3431339A
· Gyarmathy et al.
· 1969
[cited by applicant]
US 3471613A
· Gagolski
· 1969
[cited by applicant]
US 3624120A
· Yetter
· 1971
[cited by applicant]
US 3639570A
· Grand
· 1972
[cited by applicant]
US 3914404A
· Langer
· 1975
[cited by applicant]
US 3925556A
· Bauman
· 1975
[cited by applicant]
US 3932603A
· Haas
· 1976
[cited by applicant]
US 3953605A
· Bauman
· 1976
[cited by applicant]
US 3956479A
· Bauman
· 1976
[cited by applicant]
US 3985869A
· Yoshimura
· 1976
[cited by applicant]
US 4022880A
· Vinson
· 1977
[cited by applicant]
US 4042680A
· Muhler
· 1977
[cited by applicant]
US 4048299A
· Litchfield
· 1977
[cited by applicant]
US 4088752A
· Muhlemann
· 1978
[cited by applicant]
US 4108981A
· Muhler
· 1978
[cited by applicant]
US 4132773A
· Best
· 1979
[cited by applicant]
US 4154813A
· Kleinberg
· 1979
[cited by applicant]
US 4166073A
· Bauman
· 1979
[cited by applicant]
US 4235875A
· Abramo
· 1980
[cited by applicant]
US 4416867A
· Ritchey et al.
· 1983
[cited by applicant]
US 4435381A
· Flagg
· 1984
[cited by applicant]
US 4438093A
· Shimada
· 1984
[cited by applicant]
US 4618489A
· Pollock
· 1986
[cited by applicant]
US 4737359A
· Eigen
· 1988
[cited by applicant]
US 4976954A
· Kleber
· 1990
[cited by applicant]
US 5064640A
· Kleber
· 1991
[cited by applicant]
US 5281410A
· Lukacovic
· 1994
[cited by applicant]
US 5370863A
· Barney
· 1994
[cited by applicant]
US 5525330A
· Gaffar
· 1996
[cited by applicant]
US 5531982A
· Gaffar
· 1996
[cited by applicant]
US 5534243A
· Dixon, Jr.
· 1996
[cited by applicant]
US 5741487A
· Asai
· 1998
[cited by applicant]
US 5762911A
· Kleinberg
· 1998
[cited by applicant]
US 5770588A
· Mcnamara
· 1998
[cited by applicant]
US 5961958A
· Homola
· 1999
[cited by applicant]
US 6129907A
· Sreenivasan
· 2000
[cited by applicant]
US 6136298A
· Gaffar
· 2000
[cited by applicant]
US 6165447A
· Trivedi
· 2000
[cited by applicant]
US 6180599B1
· Min
· 2001
[cited by applicant]
US 6207138B1
· Zhang
· 2001
[cited by applicant]
US 6241974B1
· White, Jr. et al.
· 2001
[cited by applicant]
US 6471946B1
· Takatsuka et al.
· 2002
[cited by applicant]
US 6475537B1
· King et al.
· 2002
[cited by applicant]
US 6521216B1
· Glandorf et al.
· 2003
[cited by applicant]
US 6607711B2
· Pedersen
· 2003
[cited by applicant]
US 6846478B1
· Doyle et al.
· 2005
[cited by applicant]
US 7910139B2
· Bombardelli
· 2011
[cited by applicant]
US 7910140B2
· Wilson
· 2011
[cited by applicant]
US 8071136B2
· Kuhrts
· 2011
[cited by applicant]
US 8283135B2
· Doyle
· 2012
[cited by applicant]
US 8652495B2
· Porter
· 2014
[cited by applicant]
US 8691190B2
· Haught
· 2014
[cited by applicant]
US 8900644B2
· Trivedi
· 2014
[cited by applicant]
US 9119879B2
· Du-thumm
· 2015
[cited by applicant]
US 9192589B2
· Subramanyam
· 2015
[cited by applicant]
US 9532932B2
· Prencipe
· 2017
[cited by applicant]
US 9855200B2
· Campbell et al.
· 2018
[cited by applicant]
US 9883995B2
· Prencipe
· 2018
[cited by applicant]
US 20030003059A1
· Dana
· 2003
[cited by applicant]
US 20030003069A1
· Carson et al.
· 2003
[cited by applicant]
US 20030095931A1
· Stier
· 2003
[cited by applicant]
US 20030157145A1
· Kalili
· 2003
[cited by applicant]
US 20030165442A1
· Baig
· 2003
[cited by applicant]
US 20040037790A1
· Watanabe
· 2004
[cited by applicant]
US 20040042978A1
· Embro
· 2004
[cited by applicant]
US 20040057908A1
· Bowen
· 2004
[cited by applicant]
US 20040175480A1
· Seman et al.
· 2004
[cited by applicant]
US 20060134020A1
· Robinson et al.
· 2006
[cited by applicant]
US 20060198849A1
· Paau
· 2006
[cited by applicant]
US 20070092456A1
· Inaba
· 2007
[cited by applicant]
US 20080003186A1
· Imai
· 2008
[cited by applicant]
US 20080193531A1
· Hermelin
· 2008
[cited by applicant]
US 20080219964A1
· Keefe et al.
· 2008
[cited by applicant]
US 20090186090A1
· Zaidel
· 2009
[cited by applicant]
US 20090202450A1
· Prencipe
· 2009
[cited by applicant]
US 20100316580A1
· Kohli
· 2010
[cited by applicant]
US 20100322987A1
· Robinson
· 2010
[cited by applicant]
US 20100330003A1
· Robinson
· 2010
[cited by applicant]
US 20110039927A1
· Madsen et al.
· 2011
[cited by applicant]
US 20110052509A1
· Subramanyam
· 2011
[cited by applicant]
US 20120237455A1
· Trivedi et al.
· 2012
[cited by applicant]
US 20120237456A1
· Trivedi et al.
· 2012
[cited by applicant]
US 20120244086A1
· Trivedi et al.
· 2012
[cited by applicant]
US 20120244087A1
· Trivedi et al.
· 2012
[cited by applicant]
US 20130142736A1
· Robinson
· 2013
[cited by applicant]
US 20150297477A1
· Poth
· 2015
[cited by applicant]
US 20150297500A1
· Robinson
· 2015
[cited by applicant]
US 20150313813A1
· Rege
· 2015
[cited by applicant]
US 20160250122A1
· Lin et al.
· 2016
[cited by applicant]
US 20160324738A1
· Baig
· 2016
[cited by applicant]
US 20160324741A1
· Baig
· 2016
[cited by applicant]
US 20170319444A1
· Dehghan
· 2017
[cited by applicant]
US 20180072944A1
· Shi
· 2018
[cited by applicant]
US 20210093528A1
· St. John et al.
· 2021
[cited by applicant]
US 20210093549A1
· Baig et al.
· 2021
[cited by applicant]
US 20210093551A1
· Baig et al.
· 2021
[cited by applicant]
US 20220304918A1
· Baig et al.
· 2022
[cited by applicant]
US 20220304919A1
· St. John
· 2022
[cited by applicant]
US 20220313595A1
· Baig et al.
· 2022
[cited by applicant]
US 20230293401A1
· Baig
· 2023
[cited by applicant]
US 20240299264A1
· Baig
· 2024
[cited by applicant]
US 20240382396A1
· Baig
· 2024
[cited by applicant]
US 20250009617A1
· St. John et al.
· 2025
[cited by applicant]
CN 101123943A
· 2008
[cited by applicant]
CN 102811698A
· 2012
[cited by applicant]
CN 106075545A
· 2016
[cited by applicant]
CN 106029175A
· 2016
[cited by applicant]
CN 106309215A
· 2017
[cited by applicant]
CN 106309629A
· 2017
[cited by applicant]
CN 106389138A
· 2017
[cited by applicant]
CN 106937921A
· 2017
[cited by applicant]
CN 107468587A
· 2017
[cited by applicant]
CN 108938544A
· 2018
[cited by applicant]
EP 0311260B1
· 1994
[cited by applicant]
EP 0875238A2
· 1998
[cited by applicant]
EP 0740932B1
· 2002
[cited by applicant]
EP 1185237B1
· 2003
[cited by applicant]
EP 1200053B1
· 2005
[cited by applicant]
EP 1203575B1
· 2010
[cited by applicant]
EP 1843741B1
· 2013
[cited by applicant]
EP 2753292B1
· 2018
[cited by applicant]
GB 1115370A
· 1968
[cited by applicant]
GB 1130566A
· 1968
[cited by applicant]
GB 1355233A
· 1974
[cited by applicant]
JP S5326331A
· 1978
[cited by applicant]
JP S63211219A
· 1988
[cited by applicant]
JP 2001504083A
· 2001
[cited by applicant]
JP 2001258502A
· 2001
[cited by applicant]
JP 2008143870A
· 2008
[cited by applicant]
JP 2009514789A
· 2009
[cited by applicant]
JP 4347161B2
· 2009
[cited by applicant]
JP 2011063556A
· 2011
[cited by applicant]
JP 2011088939A
· 2011
[cited by applicant]
JP 2013512905A
· 2013
[cited by applicant]
JP 2013523730A
· 2013
[cited by applicant]
JP 2014221781A
· 2014
[cited by applicant]
JP 2015521604A
· 2015
[cited by applicant]
JP 2015155438A
· 2015
[cited by applicant]
JP 2016516777A
· 2016
[cited by applicant]
JP 2018091028A
· 2018
[cited by applicant]
JP 2019052186A
· 2019
[cited by applicant]
KR 20110133194A
· 2011
[cited by applicant]
WO 9107163A1
· 1991
[cited by applicant]
WO 9909842A1
· 1999
[cited by applicant]
WO 0110401A1
· 2001
[cited by applicant]
WO 2006027248A2
· 2006
[cited by applicant]
WO 2006040189A1
· 2006
[cited by applicant]
WO 2007012080A3
· 2007
[cited by applicant]
WO 2007061796A2
· 2007
[cited by applicant]
WO 2008041055A1
· 2008
[cited by applicant]
WO 2008065875A1
· 2008
[cited by applicant]
WO 2011053291A1
· 2011
[cited by applicant]
WO 2012057739A1
· 2012
[cited by applicant]
WO 2012087288A2
· 2012
[cited by applicant]
WO 2015171836A1
· 2015
[cited by applicant]
WO 2015171837A1
· 2015
[cited by applicant]
WO 2019183888A1
· 2019
[cited by applicant]
WO 2022067140A1
· 2022
[cited by applicant]
WO 2022067141A1
· 2022
[cited by applicant]
WO 2022067142A1
· 2022
[cited by applicant]
“BetaBio 45%”, XP055755137, Retrieved from the Internet:URL:https://www.hopsteiner.com/wp-content/uploads/2019/07/25_09_BetaBio-45.pdf; Jul. 1, 2019, 3 pages.
[cited by applicant]
“GNPD—Maximum Bio-Active Super Fresh Toothpaste”, XP0551 86450, Retrieved from the Internet: URL: http://www.gnpd.com/sinatra/recordpage/2337697/from_search/IQ5ZuZM2pG/, Mar. 1, 2014, 2 Pages.
[cited by applicant]
0ral Care, Honeywell Fine Chemicals, Retrieved from URL: https://www.additiveschemicals-honeywell.com/finechemicals/applications/personal-care/oral-care/, Nov. 30, 2020, pp. 1-3.
[cited by applicant]
PCT Search Report and Written Opinion for PCT/US2020/070597 dated Dec. 14, 2020, 13 pages.
[cited by applicant]
Agarwal et al., “Prevention of Dental Caries-Measures beyond Fluoride.”, In Journal of Oral Hygiene & Health, vol. 2, Issue 1, Mar. 3, 2014, 6 Pages.
[cited by applicant]
Akande, O.O. et al., “A Laboratory Evaluation of the Efficacy of a Herbal Dentifrice on Dental Caries in the Rat”, African J of Bio Res, vol. 7, 2004, pp. 89-92.
[cited by applicant]
All Office Actions: U.S. Appl. No. 18/418,609, filed Jan. 22, 2024; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/037,766, filed Sep. 30, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/037,773, filed Sep. 30, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/037,776, filed Sep. 30, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/037,780, filed Sep. 30, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/037,789, filed Sep. 30, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/116,389, filed Dec. 9, 2020; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/704,023, filed Mar. 25, 2022; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/704,027, filed Mar. 25, 2022; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 17/704,028, filed Mar. 25, 2022; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 18/322,652, filed May 24, 2023. See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 18/322,979, filed May 24, 2023. See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 18/655,468, filed May 6, 2024; See Patent Center.
[cited by applicant]
All Office Actions; U.S. Appl. No. 18/788,266, filed Jul. 30, 2024; See Patent Center.
[cited by applicant]
Anbar, M. et al. “Organic Polymeric Polyphosphonates as Potential Preventive Agents of Dental Caries: In Vivo Experiments”, J. Dent Res, vol. 53(5), 1974, pp. 1240-1244.
[cited by applicant]
Barth Haas Isohop technical data sheet, Rev. 7, approved on Jul. 4, 2022, 3 pages.
[cited by applicant]
Bhattacharya et al., “Inhibition of
[cited by applicant]
Bogdanova et al. “Antibiofilm activity of bioactive hop compounds humulone, lupulone and xanthohumol toward susceptible and resistant staphylococci”, Research in Microbiology Journal, vol. 169, Issue 3, Apr. 2018, pp. 1…
[cited by applicant]
Colgate, “What are the Signs and Symptoms of Gingivitis?”, Online retrieved from ““https://www.colgate.com/en-us/oral-health/gum-disease/what-is-gingivitis-signs-and-symptoms” target=”_blank“https://www.colgate.com/en-u…
[cited by applicant]
Comprehensive Separation and Structural Analyses of Polyphenolsand Related Compounds from Bracts of Hops, XP 55753130A1 Journal of Agricultural and food chemistry, Yoshihisa Tanaka, Year, 2014, pp. 2198-2206.
[cited by applicant]
Database GNPD [Online] Mintel, anonymous: “Regular Mouth Wash”, XP055753124, Retrieved from www.gnpd.com, Database accession No. 10441104 abstract, Feb. 5, 2009, pp. 1-3.
[cited by applicant]
Database GNPD [Online] Mintel, anonymous: “Strawberry Milk Flavoured Anti-Cavity Toothpaste for Kids”, XP055755176, Database accession No. 4757005; Apr. 18, 2017, p. 1-3.
[cited by applicant]
Database GNPD [Online] Mintel, anonymous: “Whitening Tooth Powder”, XP055755184, Database accession No. 1777364 abstract, Apr. 23, 2012, pp. 1-4.
[cited by applicant]
Database GNPD [Online] Miintel, anonymous: “Daily Toothpaste!”, XP055755179, Database accession No. 3287031 Abstract, Jul. 14, 2015, pp. 1-3.
[cited by applicant]
Database WPI, Week 201807, Feb. 1, 2008 (Feb. 1, 2008), Thomson Scientific, London, GB; AN 2017-88895Q XP002801332, & CN 107485599 A (Univ Southwest) Dec. 19, 2017, pp. 4-8.
[cited by applicant]
Gaffar, Abdul et al. “Effects of Editempa on Dental Calculus and Caries Formation in Vivo”, Calcif Tissue Int 35,1983, pp. 362-365.
[cited by applicant]
Harris, G., “Amino Acids and Peptides of Hops and Wort: I. Techniques and new compounds.”, Journal of the Institute of Brewing, vol. 58, 1952, pp. 417-428.
[cited by applicant]
Hopsteiner Store, XP 93067800A1, Consent to Cookies & Data processing, URL Link; https;//lwww.hopsteiner-shopde/en/about-hopsteiner, No Known Date, 3 pgs.
[cited by applicant]
Hopsteiner, Beta Bio45%, XP55753265A1, No Known date, 3 Pages.
[cited by applicant]
Jason Tetro, “The Secret to Better Teeth Found in Beer Breweries”, Under the Microscope, Retrieved from the Internet: URL: https://www.popsci.com/blog-network/under-microscope/secret-better-teeth-found-beer-breweries/, …
[cited by applicant]
Knowde, “Hopsteiner Beta Bio 45% Hops Extract-Anti-Microbial Agent”, Online retrieved from “www.knowde.comstoreshopsteinerproducts”, Feb. 16, 2021, 07 pages.
[cited by applicant]
Mckenna Francine: “German Inventions in Everyday Use”, XP055773018, Retrieved from the Internet: URL:https://www.germanpulse.com/2012/05/08/german-inventions-in-everyday-use/[retrieved on Feb. 5, 2021] the whole documen…
[cited by applicant]
Meyer et al. “Quantifying Drug Combination Synergy along Potency and Efficacy Axes”, Retrieved from Internet: https://pubmed.ncbi.nlm.nih.gov/30797775/, Feb. 27, 2019, 46 Pages.
[cited by applicant]
Muhlemann, HR et al. “Reduction of Plaque and Gingivitis by Stannous Fluoride Stabilized with Amine Fluoride”, Caries Research 15:2 , 1981,1 page.
[cited by applicant]
Roger Stevens, “The Chemistry of Hop Constituents”, Brewing Industry Research Foundation, Mar. 31, 1966, pp. 19-71.
[cited by applicant]
Rotgans, J et al. “The Effect of Brushing with a Toothpaste Containing Amyloglucosidase and Glucose Oxidase on Dental Caries in Rats”, Caries Res. 13, 1979, pp. 150-153.
[cited by applicant]
Sharma, Siddharth et al. “Laboratory Evaluation of the Efficacy of Formulated Polyherbal Toothpaste “Oralis S” on Dental Caries in Rats”, IJPRAS, vol. 3(2), 2014, pp. 47-50.
[cited by applicant]
Simpson et al., “Factors Affecting Antibacterial Activity of Hop Compounds and Their Derivatives”, Journal of Applied Bacteriology, vol. 72, 1992, pp. 327-334.
[cited by applicant]
Spirit Dental, “A Step-by-Step Guide to Proper Teeth Brushing”, Online retrieved from“https://spiritdental.com/blog/categories/dental-health/a-step-by-step-guide-to-proper-teeth-brushing”, 2019; 02 pages.
[cited by applicant]
Spiritdental.com_ A Step-by-Step Guide to Proper Teeth Brushing, “www.spiritdental.com”, Published online Jul. 18, 2019, 5 Pages.
[cited by applicant]
Stookey, G. K. et al. “Animal Caries Models For Evaluating Fluoride Dentifrices” Adv. Dent. Res 9(3), Nov. 1995, pp. 198-207.
[cited by applicant]
Sullivan, RJ et al. “Development of an enhanced anticaries efficacy dual component dentifrice containing sodium fluoride and dicalcium phosphate dihydrate” Am J. Dent , 14 Spec No. 3A-11A, May 2001, pp. 1-2.
[cited by applicant]
Wang et al., “Glycine inhibits the LPS-induced increase in cytosolic Ca2+ concentration and TNF α production in cardiomyocytes by activating a glycine receptor”, Retrieved from: https://doi.org/10.1038/aps.2009.106, Jul…
[cited by applicant]
Xiang, et al., “Penetration and Bactericidal Efficacy of Two Oral Care Products in an Oral Biofilm Model”, Am J Dent, vol. 31, Issue1, Feb. 2018, 07 pages.
[cited by applicant]
Yang et al. “Relation between chemotaxis and consumption of amino acids in bacteria”, Molecular Microbiology 96, 2015, pp. 1272-1282.
[cited by applicant]
EPO Search Report and Opinion for 25199823.3 dated Jan. 22, 2026, 09 pages.
[cited by applicant]