WO1993020167A1 - Acidic activated bleaching compositon - Google Patents
Acidic activated bleaching compositon Download PDFInfo
- Publication number
- WO1993020167A1 WO1993020167A1 PCT/US1993/002944 US9302944W WO9320167A1 WO 1993020167 A1 WO1993020167 A1 WO 1993020167A1 US 9302944 W US9302944 W US 9302944W WO 9320167 A1 WO9320167 A1 WO 9320167A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- hydrogen peroxide
- compositions
- organic peracid
- peracid precursor
- Prior art date
Links
- 238000004061 bleaching Methods 0.000 title claims abstract description 12
- 230000002378 acidificating effect Effects 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 70
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002243 precursor Substances 0.000 claims abstract description 21
- 150000004967 organic peroxy acids Chemical class 0.000 claims abstract description 16
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000001087 glyceryl triacetate Substances 0.000 claims description 7
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 7
- 229960002622 triacetin Drugs 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- -1 ethylene glycol diesters Chemical class 0.000 claims description 4
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 3
- 239000004348 Glyceryl diacetate Substances 0.000 claims description 2
- 235000019443 glyceryl diacetate Nutrition 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000002314 glycerols Chemical class 0.000 abstract description 2
- 150000002334 glycols Chemical class 0.000 abstract description 2
- 150000004965 peroxy acids Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 239000012190 activator Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000005402 stannate group Chemical group 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000009897 hydrogen peroxide bleaching Methods 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3947—Liquid compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/391—Oxygen-containing compounds
Definitions
- the present invention relates to bleaching compositions, mainly for use in laundry applications.
- the compositions according to the present invention which comprise hydrogen peroxide as well as peracid precursors, are stable upon storage.
- hydrogen peroxide bleach activators have been developed and have been extensively described in the art. These activators are mainly transition metals or peracid precursors. Peracid precursors react with hydrogen peroxide to yield peracids. Peracids are the "activated" bleaching compounds which are efficient at low temperatures.
- a bleaching composition comprising hydrogen peroxide, an organic peracid precursor selected from a specific class, e.g. glycol and glycerin esters, and by formulating said composition in a narrow, acidic pH range.
- the mildly acidic pH range allows for adequate chemical stability of both the hydrogen peroxide and the organic peracid precursor.
- the activation of hydrogen peroxide trough the formation of a peracid is enhanced by the pH raise which occurs upon dilution in the wash water, especially when a detergent composition bringing further alkalinity is also present in the wash water.
- Glycol esters have been often described as solvents in detergent and bleaching compositions. Such compositions are described for instance in US 3 956 159. These compositions have a pH of 6.5 and above.
- J 62252500 discloses bleaching compositions which comprise a bleach activator, including triacetin. These compositions are formulated at neutral or weakly basic pH.
- Bleaching compositions for various applications comprising triacetin are also disclosed in J62001792, J62001794 J 62001796, and J61Q42600 (abstracts).
- compositions according to the present invention are clear aqueous bleaching compositions comprising hydrogen peroxide as well as an organic peracid precursor, characterized in that the compositions have a pH in the range of from about 3.5 to about 6, and that the organic peracid precursor is a compound according to the formula:
- R 1# R 2 , R 3 are independently selected from -H, -OH, -C-0-R 4 or -0-C-R 4 where R ⁇ is
- compositions according to the present invention are clear aqueous liquid compositions which comprise hydrogen peroxide.
- the compositions according to the present invention comprise from about 0.5 % to about 20 % by weight of the total composition of hydrogen peroxide, more preferably from about 2 % to about 15 %, most preferably from about 4 % to about 9%.
- compositions according to the present invention further comprise a specific organic peracid precursor according to the formula:
- R ⁇ , R , R 3 are independently selected from -H, -OH, -C-0-R 4 or -0-C-R 4 where R 4 is
- Preferred such peracid precursors for use in the compositions according to the present invention are selected from ethylene glycol diesters, triacetin and diacetin, or mixtures thereof. Particularly preferred compounds are triacetin and ethylene glycol diacetate. Tributyrin also displays excellent stability in the compositions according to the present invention but is less preferred because it is less soluble in the compositions according to the present invention.
- compositions according to the present invention typically comprise from about 1 % to about 15 % by weight of the total composition of such an organic peracid precursor, or mixtures thereof.
- the desired amount of organic peracid precursor can also be defined in relation to the amount of hydrogen peroxide in the composition. Accordingly, the compositions according to the present invention preferably comprise from about 0.1 to about 2 moles of organic peracid precursor per mole of hydrogen peroxide.
- compositions according to the present invention have a pH in the range of from about 3.5 to about 6, most preferably from about 3.5 to about 5, most preferably about 4.
- the pH of the composition can be adjusted and buffered with such chemicals as organic and inorganic acids which are stable to oxidation, citric acid, sulphuric acid, sodium hydroxide, ammonia and amines.
- Preferred buffer for use in the compositions according to the present invention is citric acid. It is essential that the pH of the composition remains within the above range as said range is critical to ensure adequate chemical stability of the hydrogen peroxide and of the specific organic peracid precursors used in the compositions according to the present invention.
- compositions according to the present invention may comprise surfactants.
- Preferred surfactants for use herein are well known anionic surfactants such as alkyl benzene sulphonates and alkyl sulfates, and/or nonionic surfactants such as ethoxylated a ⁇ d/or propoxylated alcohols. All surfactants for use herein must be resistant to oxidation by peracids and hydrogen peroxide, and are preferably water-soluble.
- the compositions according to the present invention can comprise from 0% to about 30% by weight of the total composition of surfactants, preferably from about 0.5 % to about 15 %, most preferably from about 2 % to 8 %.
- compositions according to the present invention may further comprise peroxide stabilizers such as stannates, 8-hydroxyquinoline, pyrophosphates and phosphonates.
- Chelating agents may also be useful in the context of the present invention; suitable chelants include EDTA, NTA and DETPA, picolinic and dipicolinic acids and amino polyphosphonates, although some of these are poorly environmentally compatible.
- Radical scavengers can also be used herein, such as butylated hydroxy toluene and other hindered hydroxy benzenes, or sodium benzoate. Butylated hydroxy toluene is a highly preferred ingredient as it has been observed that it stabilizes the peracid precursors according to the present invention, as well as hydrogen peroxide.
- compositions according to the present invention can also comprise such optional ingredients as whitening agents, dyes, builders, thickeners, hydrotropes, perfumes, all of which need to be compatible with the mildly acidic pH and the oxidizing environment of the compositions according to the present invention.
- compositions according to the present invention are further illustrated in the following examples.
- compositions are made by mixing together the listed ingredients in the listed proportions.
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU39399/93A AU668936B2 (en) | 1992-04-03 | 1993-03-29 | Acidic activated bleaching compositon |
| JP5517617A JPH07505437A (ja) | 1992-04-03 | 1993-03-29 | 酸性活性化漂白組成物 |
| BR9306183A BR9306183A (pt) | 1992-04-03 | 1993-03-29 | Composiçao alvejante ativada ácida |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19920200961 EP0563460B1 (en) | 1992-04-03 | 1992-04-03 | Acidic activated bleaching composition |
| EP92200961.8 | 1992-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993020167A1 true WO1993020167A1 (en) | 1993-10-14 |
Family
ID=8210529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1993/002944 WO1993020167A1 (en) | 1992-04-03 | 1993-03-29 | Acidic activated bleaching compositon |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0563460B1 (cs) |
| JP (1) | JPH07505437A (cs) |
| CN (1) | CN1078254A (cs) |
| AU (1) | AU668936B2 (cs) |
| BR (1) | BR9306183A (cs) |
| DE (1) | DE69226072T2 (cs) |
| ES (1) | ES2118105T3 (cs) |
| IE (1) | IE930263A1 (cs) |
| TW (1) | TW299351B (cs) |
| WO (1) | WO1993020167A1 (cs) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753138A (en) * | 1993-06-24 | 1998-05-19 | The Procter & Gamble Company | Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations |
| US5879409A (en) * | 1996-02-23 | 1999-03-09 | The Procter & Gamble Company | Bleach additive and bleaching compositions having glycine anhydride activators |
| US6221341B1 (en) * | 1997-11-19 | 2001-04-24 | Oraceutical Llc | Tooth whitening compositions |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995004127A1 (en) * | 1993-08-03 | 1995-02-09 | The Procter & Gamble Company | A process of cleaning carpets using active oxygen compounds in an acidic aqueous medium |
| GB9600159D0 (en) * | 1996-01-05 | 1996-03-06 | Warwick Int Group | Process for bleaching or disinfecting a substrate |
| US7919122B2 (en) | 2003-04-02 | 2011-04-05 | Kao Corporation | Composition for production of a sterilizer and a process for producing organic peracid |
| ES2306838T3 (es) * | 2003-07-08 | 2008-11-16 | THE PROCTER & GAMBLE COMPANY | Composicion activadora liquida. |
| AU2009291795B2 (en) * | 2008-09-10 | 2014-01-09 | Danisco Us Inc. | Enzymatic textile bleaching compositions and methods of use thereof |
| US8546449B2 (en) | 2011-03-24 | 2013-10-01 | Enviro Tech Chemical Services, Inc. | Methods and compositions for the generation of peracetic acid on site at the point-of-use |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956159A (en) * | 1974-11-25 | 1976-05-11 | The Procter & Gamble Company | Stable concentrated liquid peroxygen bleach composition |
| JPS6142600A (ja) * | 1984-08-06 | 1986-03-01 | 花王株式会社 | カビ取り剤組成物 |
| JPS621796A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS621794A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS621792A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS62252500A (ja) * | 1986-04-25 | 1987-11-04 | 花王株式会社 | 漂白剤組成物 |
| US4800038A (en) * | 1988-01-21 | 1989-01-24 | Colgate-Palmolive Company | Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners |
| US5047168A (en) * | 1988-01-21 | 1991-09-10 | Colgate-Palmolive Co. | Sugar ethers as bleach stable detergency boosters |
| US5151212A (en) * | 1990-03-21 | 1992-09-29 | The Belzak Corporation | Peroxygen compound activation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3465334D1 (en) * | 1983-04-14 | 1987-09-17 | Interox Chemicals Ltd | Peroxygen compounds |
-
1992
- 1992-04-03 EP EP19920200961 patent/EP0563460B1/en not_active Expired - Lifetime
- 1992-04-03 ES ES92200961T patent/ES2118105T3/es not_active Expired - Lifetime
- 1992-04-03 DE DE1992626072 patent/DE69226072T2/de not_active Expired - Fee Related
-
1993
- 1993-03-29 AU AU39399/93A patent/AU668936B2/en not_active Ceased
- 1993-03-29 JP JP5517617A patent/JPH07505437A/ja active Pending
- 1993-03-29 BR BR9306183A patent/BR9306183A/pt not_active Application Discontinuation
- 1993-03-29 WO PCT/US1993/002944 patent/WO1993020167A1/en active Application Filing
- 1993-04-02 IE IE930263A patent/IE930263A1/en not_active IP Right Cessation
- 1993-04-03 CN CN 93105485 patent/CN1078254A/zh active Pending
- 1993-05-03 TW TW82103446A patent/TW299351B/zh active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956159A (en) * | 1974-11-25 | 1976-05-11 | The Procter & Gamble Company | Stable concentrated liquid peroxygen bleach composition |
| JPS6142600A (ja) * | 1984-08-06 | 1986-03-01 | 花王株式会社 | カビ取り剤組成物 |
| JPS621796A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS621794A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS621792A (ja) * | 1985-06-28 | 1987-01-07 | 花王株式会社 | 漂白剤組成物 |
| JPS62252500A (ja) * | 1986-04-25 | 1987-11-04 | 花王株式会社 | 漂白剤組成物 |
| US4800038A (en) * | 1988-01-21 | 1989-01-24 | Colgate-Palmolive Company | Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners |
| US5047168A (en) * | 1988-01-21 | 1991-09-10 | Colgate-Palmolive Co. | Sugar ethers as bleach stable detergency boosters |
| US5151212A (en) * | 1990-03-21 | 1992-09-29 | The Belzak Corporation | Peroxygen compound activation |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753138A (en) * | 1993-06-24 | 1998-05-19 | The Procter & Gamble Company | Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations |
| US5879409A (en) * | 1996-02-23 | 1999-03-09 | The Procter & Gamble Company | Bleach additive and bleaching compositions having glycine anhydride activators |
| US6221341B1 (en) * | 1997-11-19 | 2001-04-24 | Oraceutical Llc | Tooth whitening compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| TW299351B (cs) | 1997-03-01 |
| IE930263A1 (en) | 1993-10-06 |
| ES2118105T3 (es) | 1998-09-16 |
| AU3939993A (en) | 1993-11-08 |
| CN1078254A (zh) | 1993-11-10 |
| AU668936B2 (en) | 1996-05-23 |
| EP0563460A1 (en) | 1993-10-06 |
| DE69226072T2 (de) | 1999-02-25 |
| EP0563460B1 (en) | 1998-07-01 |
| JPH07505437A (ja) | 1995-06-15 |
| DE69226072D1 (de) | 1998-08-06 |
| BR9306183A (pt) | 1998-06-23 |
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