CA1254149A - Stabilizing of cinnamic aldehyde-containing flavors with terpenes and sesqueterpenes and propylene glycol and dipropylene glycol - Google Patents

Stabilizing of cinnamic aldehyde-containing flavors with terpenes and sesqueterpenes and propylene glycol and dipropylene glycol

Info

Publication number: CA1254149A
Authority: CA; Canada
Prior art keywords: cinnamic aldehyde; dentifrice; dental cream; dental; weight
Prior art date: 1984-02-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000473837A

Other languages

English (en)

French (fr)

Inventor

Robert J. Steltenkamp

Miriam L. Douglass

Gerard E. Natarelli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Colgate Palmolive Co

Original Assignee

Colgate Palmolive Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-02-09

Filing date

1985-02-08

Publication date

1989-05-16

1984-02-09 Priority claimed from US06/578,457 external-priority patent/US4562064A/en

1984-02-10 Priority claimed from US06/578,942 external-priority patent/US4547361A/en

1985-02-08 Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co

1989-05-16 Application granted granted Critical

1989-05-16 Publication of CA1254149A publication Critical patent/CA1254149A/en

Status Expired legal-status Critical Current

Links

DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title claims abstract description 129
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 title claims abstract description 120
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 title claims abstract description 120
229940117916 cinnamic aldehyde Drugs 0.000 title claims abstract description 120
AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 title claims abstract description 117
239000000796 flavoring agent Substances 0.000 title claims abstract description 86
150000003505 terpenes Chemical class 0.000 title claims abstract description 43
235000007586 terpenes Nutrition 0.000 title claims abstract description 43
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 title claims abstract description 19
235000019634 flavors Nutrition 0.000 title claims description 83
230000000087 stabilizing effect Effects 0.000 title description 2
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims abstract description 84
239000000203 mixture Substances 0.000 claims abstract description 74
239000000551 dentifrice Substances 0.000 claims abstract description 53
229940087305 limonene Drugs 0.000 claims abstract description 43
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WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims abstract description 35
229940043350 citral Drugs 0.000 claims abstract description 35
238000002845 discoloration Methods 0.000 claims abstract description 35
WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims abstract description 35
238000009472 formulation Methods 0.000 claims abstract description 25
229930004725 sesquiterpene Natural products 0.000 claims abstract description 23
150000004354 sesquiterpene derivatives Chemical class 0.000 claims abstract description 23
230000032683 aging Effects 0.000 claims abstract description 21
150000001299 aldehydes Chemical class 0.000 claims abstract description 19
239000003381 stabilizer Substances 0.000 claims abstract description 14
UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical class CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 claims abstract description 12
JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 claims abstract description 8
239000007800 oxidant agent Substances 0.000 claims abstract description 8
235000016639 Syzygium aromaticum Nutrition 0.000 claims abstract description 7
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239000000341 volatile oil Substances 0.000 claims abstract description 7
VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Chemical class CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 claims abstract description 6
JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 claims abstract description 4
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 18
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239000002324 mouth wash Substances 0.000 claims description 14
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NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
239000004408 titanium dioxide Substances 0.000 claims description 9
239000003112 inhibitor Substances 0.000 claims description 8
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NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 claims description 5
FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 claims description 5
NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 claims description 5
NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 claims description 5
229940117948 caryophyllene Drugs 0.000 claims description 5
125000000396 limonene group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 18
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235000013355 food flavoring agent Nutrition 0.000 abstract description 3
235000019499 Citrus oil Nutrition 0.000 abstract description 2
239000010500 citrus oil Substances 0.000 abstract description 2
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235000013772 propylene glycol Nutrition 0.000 description 35
229960004063 propylene glycol Drugs 0.000 description 35
238000004383 yellowing Methods 0.000 description 33
-1 poly(oxyethylene) Polymers 0.000 description 22
235000011187 glycerol Nutrition 0.000 description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 12
235000013599 spices Nutrition 0.000 description 12
239000004615 ingredient Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
239000003981 vehicle Substances 0.000 description 10
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 9
230000007935 neutral effect Effects 0.000 description 9
235000019333 sodium laurylsulphate Nutrition 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
230000009467 reduction Effects 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
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229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000000600 sorbitol Substances 0.000 description 7
235000010356 sorbitol Nutrition 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003599 detergent Substances 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 6
239000003349 gelling agent Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 6
235000010234 sodium benzoate Nutrition 0.000 description 6
239000004299 sodium benzoate Substances 0.000 description 6
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 6
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 6
XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 5
238000006701 autoxidation reaction Methods 0.000 description 5
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AXCXHFKZHDEKTP-UHFFFAOYSA-N 3-(4-methoxyphenyl)prop-2-enal Chemical compound COC1=CC=C(C=CC=O)C=C1 AXCXHFKZHDEKTP-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
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238000006243 chemical reaction Methods 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 4
238000006735 epoxidation reaction Methods 0.000 description 4
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
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235000019739 Dicalciumphosphate Nutrition 0.000 description 3
239000005770 Eugenol Substances 0.000 description 3
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UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
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150000001336 alkenes Chemical class 0.000 description 3
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125000002947 alkylene group Chemical group 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 3
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
235000019501 Lemon oil Nutrition 0.000 description 1
BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 1
229910000503 Na-aluminosilicate Inorganic materials 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical compound CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 1
239000004965 Silica aerogel Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000003082 abrasive agent Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000012443 analytical study Methods 0.000 description 1
229940011037 anethole Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
229940043256 calcium pyrophosphate Drugs 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
XFWJKVMFIVXPKK-UHFFFAOYSA-N calcium;oxido(oxo)alumane Chemical compound [Ca+2].[O-][Al]=O.[O-][Al]=O XFWJKVMFIVXPKK-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
229930002875 chlorophyll Natural products 0.000 description 1
235000019804 chlorophyll Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
239000010630 cinnamon oil Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910002026 crystalline silica Inorganic materials 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
235000019821 dicalcium diphosphate Nutrition 0.000 description 1
UMGSFZGNYYDQSL-UHFFFAOYSA-H disodium;tin(4+);hexafluoride Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[Na+].[Na+].[Sn+4] UMGSFZGNYYDQSL-UHFFFAOYSA-H 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229960005150 glycerol Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
229930007453 limonene-1,2-epoxide Natural products 0.000 description 1
CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 description 1
KBDSLGBFQAGHBE-MSGMIQHVSA-N limonin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@@H]2[C@]34COC(=O)C[C@@H]3OC2(C)C)C=COC=1 KBDSLGBFQAGHBE-MSGMIQHVSA-N 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
229960002261 magnesium phosphate Drugs 0.000 description 1
229910000157 magnesium phosphate Inorganic materials 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000005935 nucleophilic addition reaction Methods 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
CKRORYDHXIRZCH-UHFFFAOYSA-N phosphoric acid;dihydrate Chemical compound O.O.OP(O)(O)=O CKRORYDHXIRZCH-UHFFFAOYSA-N 0.000 description 1
239000000467 phytic acid Substances 0.000 description 1
229940068041 phytic acid Drugs 0.000 description 1
235000002949 phytic acid Nutrition 0.000 description 1
229960000502 poloxamer Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
108700004121 sarkosyl Proteins 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003760 tallow Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
229940117960 vanillin Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Birds (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Oral & Maxillofacial Surgery (AREA)
Cosmetics (AREA)

CA000473837A 1984-02-09 1985-02-08 Stabilizing of cinnamic aldehyde-containing flavors with terpenes and sesqueterpenes and propylene glycol and dipropylene glycol Expired CA1254149A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US578,457		1984-02-09
US06/578,457 US4562064A (en)	1984-02-09	1984-02-09	Stabilizing of cinnamic aldehyde-containing flavors with terpenes and sesqueterpenes
US06/578,942 US4547361A (en)	1984-02-10	1984-02-10	Stabilizing of cinnamic aldehyde-containing flavors with propylene glycol and dipropylene glycol
US578,942		1990-09-07

Publications (1)

Publication Number	Publication Date
CA1254149A true CA1254149A (en)	1989-05-16

Family

ID=27077506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000473837A Expired CA1254149A (en)	1984-02-09	1985-02-08	Stabilizing of cinnamic aldehyde-containing flavors with terpenes and sesqueterpenes and propylene glycol and dipropylene glycol

Country Status (16)

Country	Link
AT (1)	AT388664B (de)
AU (1)	AU573307B2 (de)
BE (1)	BE901690A (de)
BR (1)	BR8500529A (de)
CA (1)	CA1254149A (de)
CH (1)	CH668359A5 (de)
DE (1)	DE3502830A1 (de)
DK (1)	DK53585A (de)
ES (1)	ES8700929A1 (de)
FR (1)	FR2559387B1 (de)
GB (1)	GB2153679B (de)
IT (1)	IT1184263B (de)
MX (1)	MX163219B (de)
NL (1)	NL8500359A (de)
PH (1)	PH21607A (de)
PT (1)	PT79930B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4514617A (en) *	1983-01-19	1985-04-30	Haim Amit	Two-stage electric water heater
DE19754282A1 (de) *	1997-12-08	1999-06-10	Henkel Kgaa	Kosmetische Mittel
IL135220A0 (en) *	2000-03-22	2001-05-20	Simcha Wolnerman Joseph	A composition containing an extract of a citrus fruit
US9591852B2 (en)	2009-11-23	2017-03-14	Mcneil-Ppc, Inc.	Biofilm disruptive compositions
CN116120159A (zh) *	2023-03-03	2023-05-16	无锡江大百泰科技有限公司	一种肉桂醛的提取方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3562385A (en) *	1968-12-23	1971-02-09	Merck & Co Inc	Dental antiplaque and anticalculus compositions
US3671630A (en) *	1970-08-17	1972-06-20	Lever Brothers Ltd	Halogenated phenolic germicidal compositions containing terpene color stabilizers
AU463173B2 (en) *	1971-01-20	1975-07-17	Warner-Lambert Company	Reodorant compositions
US3864472A (en) *	1972-11-06	1975-02-04	Colgate Palmolive Co	Clear lemon-flavored mouthwash
US3867557A (en) *	1973-04-19	1975-02-18	Procter & Gamble	Compositions of matter containing paramethoxycinnamaldehyde as a flavoring agent and sweetener
US3928560A (en) *	1973-04-19	1975-12-23	Procter & Gamble	Compositions of matter containing paramethoxycinnamaldehyde as a flavoring agent and sweetener
LU68016A1 (de) *	1973-07-13	1975-04-11
US4001438A (en) *	1974-10-15	1977-01-04	International Flavors & Fragrances Inc	Flavor composition for use in orally utilizable compositions
US4132771A (en) *	1977-08-24	1979-01-02	Schreiber Ronald S	Warm two tone flavored dentifrice
US4187287A (en) *	1977-08-24	1980-02-05	Colgate Palmolive Company	Warm two tone flavored dentifrice
US4198394A (en) *	1978-07-25	1980-04-15	Faunce Frank R	Sodium dihydrogen phosphate enhanced dentifrice composition
FR2440189A1 (fr) *	1978-11-01	1980-05-30	Unilever Nv	Produits a usage buccal contenant un germicide cationique de gout amer, avec un arome masquant, et leur preparation
US4242323A (en) *	1979-08-22	1980-12-30	Vlock D G	Plaque inhibiting oral composition
GB2082062B (en) *	1980-08-19	1984-07-11	Colgate Palmolive Co	Dentifrices containing xanthan and guar gum
JPS595109A (ja) *	1982-06-30	1984-01-12	Lion Corp	口腔用組成物
US4420471A (en) *	1983-01-10	1983-12-13	Lever Brothers Company	Citrus flavored mouthwash formulation method

1985
- 1985-01-29 DE DE19853502830 patent/DE3502830A1/de not_active Withdrawn
- 1985-02-05 CH CH522/85A patent/CH668359A5/de not_active IP Right Cessation
- 1985-02-05 AT AT0033085A patent/AT388664B/de not_active IP Right Cessation
- 1985-02-06 PT PT79930A patent/PT79930B/pt unknown
- 1985-02-06 BR BR8500529A patent/BR8500529A/pt unknown
- 1985-02-06 DK DK53585A patent/DK53585A/da not_active Application Discontinuation
- 1985-02-07 PH PH31826A patent/PH21607A/en unknown
- 1985-02-07 MX MX204266A patent/MX163219B/es unknown
- 1985-02-08 NL NL8500359A patent/NL8500359A/nl not_active Application Discontinuation
- 1985-02-08 IT IT47658/85A patent/IT1184263B/it active
- 1985-02-08 AU AU38566/85A patent/AU573307B2/en not_active Ceased
- 1985-02-08 ES ES540246A patent/ES8700929A1/es not_active Expired
- 1985-02-08 FR FR858501812A patent/FR2559387B1/fr not_active Expired
- 1985-02-08 BE BE0/214481A patent/BE901690A/fr not_active IP Right Cessation
- 1985-02-08 CA CA000473837A patent/CA1254149A/en not_active Expired
- 1985-02-11 GB GB08503470A patent/GB2153679B/en not_active Expired

Also Published As

Publication number	Publication date
NL8500359A (nl)	1985-09-02
FR2559387B1 (fr)	1989-04-28
DK53585A (da)	1985-08-10
ES540246A0 (es)	1986-11-16
ES8700929A1 (es)	1986-11-16
IT1184263B (it)	1987-10-22
AT388664B (de)	1989-08-10
FR2559387A1 (fr)	1985-08-16
GB2153679B (en)	1987-11-18
DK53585D0 (da)	1985-02-06
GB2153679A (en)	1985-08-29
GB8503470D0 (en)	1985-03-13
PT79930B (en)	1986-11-12
PT79930A (en)	1985-03-01
DE3502830A1 (de)	1985-08-14
BE901690A (fr)	1985-08-08
MX163219B (es)	1992-03-11
AU573307B2 (en)	1988-06-02
BR8500529A (pt)	1985-09-24
AU3856685A (en)	1985-08-15
PH21607A (en)	1987-12-11
IT8547658A0 (it)	1985-02-08
ATA33085A (de)	1989-01-15
CH668359A5 (de)	1988-12-30

Legal Events

Date	Code	Title	Description
2006-05-16	MKEX	Expiry

Publication	Publication Date	Title
US4547361A (en)	1985-10-15	Stabilizing of cinnamic aldehyde-containing flavors with propylene glycol and dipropylene glycol
US4465661A (en)	1984-08-14	Oral product having improved taste
US4130636A (en)	1978-12-19	Dentifrice
US4465662A (en)	1984-08-14	Oral compositions of tranexamic acid and carvone
US4370314A (en)	1983-01-25	Oral composition containing antibacterial agent
US4071615A (en)	1978-01-31	Flavored dentifrice
US3925543A (en)	1975-12-09	Antibacterial oral compositions containing preservative-antioxidants
US4132772A (en)	1979-01-02	Dentifrice
US3887701A (en)	1975-06-03	Antibacterial oral compositions containing preservative-antioxidants
JPH0239485B2 (de)	1990-09-05
EP0288420A1 (de)	1988-10-26	Stabiles, Wasserstoffperoxid enthaltendes Zahngel
EP0331617A1 (de)	1989-09-06	Nichtauslaufende gestreifte Zahnpasta
CA1155398A (en)	1983-10-18	Tranexamic compound with folic acid as oral composition
JPH022857B2 (de)	1990-01-19
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