EP0837124B1 - Fluorescent whitening agent formulation - Google Patents
Fluorescent whitening agent formulation Download PDFInfo
- Publication number
- EP0837124B1 EP0837124B1 EP97810741A EP97810741A EP0837124B1 EP 0837124 B1 EP0837124 B1 EP 0837124B1 EP 97810741 A EP97810741 A EP 97810741A EP 97810741 A EP97810741 A EP 97810741A EP 0837124 B1 EP0837124 B1 EP 0837124B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formulation according
- formulation
- formula
- compound
- alkyl
- Prior art date
- 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 - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 87
- 238000009472 formulation Methods 0.000 title claims description 68
- 239000006081 fluorescent whitening agent Substances 0.000 title claims description 40
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 37
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
- 239000003599 detergent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 13
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000004435 Oxo alcohol Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000000129 anionic group Chemical group 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- -1 methoxy, phenoxy Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 3
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 14
- 239000012669 liquid formulation Substances 0.000 description 13
- 239000008367 deionised water Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000002002 slurry Substances 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 0 *c1cccc(C=Cc2ccc(C3C=CC(C=Cc4cccc(*)c4)=CC3)cc2)c1 Chemical compound *c1cccc(C=Cc2ccc(C3C=CC(C=Cc4cccc(*)c4)=CC3)cc2)c1 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- PQSMEVPHTJECDZ-UHFFFAOYSA-N 2,3-dimethylheptan-2-ol Chemical compound CCCCC(C)C(C)(C)O PQSMEVPHTJECDZ-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- 239000004439 Isononyl alcohol Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 239000010457 zeolite Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/825—Mixtures of compounds all of which are non-ionic
- C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
-
- 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
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0063—Photo- activating compounds
-
- 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
- C11D3/40—Dyes ; Pigments
- C11D3/42—Brightening agents ; Blueing agents
-
- 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
- C11D3/43—Solvents
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- the present invention relates to a fluorescent whitening agent formulation and, in particular, to a liquid fluorescent whitening agent formulation comprising a solution of a fluorescent whitening agent in a specific type of nonionic surfactant.
- aqueous slurry containing the various components of the detergent composition, including a fluorescent whitening agent.
- the detergent manufacturers prefer to use the fluorescent whitening agent component in the form of a liquid formulation, in order to facilitate the incorporation of the fluorescent whitening agent into the slurry to be spray-dried.
- fluorescent whitening agents are often supplied to the detergent manufacturers in the form of an aqueous slurry.
- Such aqueous slurries of fluorescent whitening agent usually contain large amounts of water, which must be removed during subsequent spray drying, and are often beset by problems, such as the formation of clumps during spray-drying, as well as instability to sedimentation on storage.
- liquid formulations of fluorescent whitening agents which use organic solvents and are substantially anhydrous (e.g. FR-A-2654123, EP-A-0703293). These liquid formulations, however, are usually highly viscous and need to be incorporated into the detergent powder by means of special mixing techniques.
- US-A-3,953,380 discloses liquid detergent compositions comprising fluorescent whitening agent at 0,5-5%, 40-75% non-ionic detergent and 5-35% water.
- anionic fluorescent whitening agents are soluble in a mixture comprising a predominant amount of a certain type of nonionic surfactant and a lesser amount of water, to provide stable, clear solutions of low viscosity.
- the present invention provides a liquid fluorescent whitening agent formulation which is a solution having a viscosity of 50 to 5000 mPas, preferably 100 to 3500 mPas, especially 100 to 1000 mPas and which comprises:
- m is 1, 3 or 4 and, when m is 1, R is a C 8 -C 18 -alkyl residue or a C 8 -C 18 -alkylcarboxy residue; when m is 3, R is the residue of trimethylolpropane from which the three hydroxy groups have been removed; and when m is 4, R is the residue of pentaerythritol residue from which the four hydroxy groups have been removed; R 1 is hydrogen, methyl or ethyl; and n is a number ranging from 1 to 40.
- the viscosity of the liquid fluorescent whitening agent formulation according to the present invention is determined at a shear force of 100/s and at a temperature of 25°C. ⁇ 1°C.
- Preferred anionic fluorescent whitening agents for use in the present invention are those having either of the formulae: or in which R 2 and R 3 , independently, are OH, NH 2 , O-C 1 -C 4 -alkyl, O-aryl, NH-C 1 -C 4 -alkyl, N(C 1 -C 4 -alkyl) 2 , N(C 1 -C 4 -alkyl)(C 1 -C 4 -hydroxyalkyl), N(C 1 -C 4 -hydroxyalkyl) 2 , NH-aryl, morpholino, S-C 1 -C 4 -alkyl(aryl), Cl or OH; R 4 is H, SO 3 M, O-C 1 -C 4 -alkyl, CN, Cl, COO-C 1 -C 4 -alkyl, or CON(C 1 -C 4 -alkyl) 2 ; M is H, Li, Na, K, Ca, Mg, ammonium,
- C 1 -C 4 -alkyl groups are, e.g., methyl, ethyl, n-propyl, isopropyl and n-butyl, especially methyl.
- Aryl groups are, e.g., naphthyl or, especially, phenyl.
- Preferred compounds of formula (2) are those in which R 2 and R 3 , independently, are methoxy, phenoxy, NH 2 , NH-methyl, N(methyl) 2 , N(methyl)(hydroxyethyl), NH-ethyl, N(hydroxyethyl) 2 , NH-phenyl, morpholino, S-methyl(phenyl), Cl or OH.
- Preferred compounds of formula (3) are those in which R 4 is H or Cl and p is 1.
- a mixture of two or more anionic fluorescent whitening agents may be used as component a) of the formulation according to the present invention.
- Component b) of the formulation according to the present invention is water.
- water may be used together with one or more polar co-solvents such as an alkylene glycol, e.g. ethylene glycol or 1,2-propylene glycol, or a polyalkylene glycol, especially polyethylene glycol or polypropylene glycol.
- polar co-solvents such as an alkylene glycol, e.g. ethylene glycol or 1,2-propylene glycol, or a polyalkylene glycol, especially polyethylene glycol or polypropylene glycol.
- the amount of any co-solvent preferably ranges from 0-15% by weight, based on the total weight of the formulation.
- the radical R in the compounds of formula (1), when m is 1, is derived from a C 8 -C 18 -alkyl monoalcohol.
- monoalcohols include naturally-occuring monoalcohols such as lauryl alcohol, myristyl alcohol, cetyl alcohol and stearyl alcohol, as well as synthetic alcohols such as 2-ethylhexanol, 1,1,3,3-tetramethylbutanol, octan-2-ol, isononyl alcohol, trimethylhexanol, trimethylnonyl alcohol, n-decanol, C 9 -C 13 -oxoalcohols, tridecyl alcohol, isodecyl alcohol or C 8 -C 18 -linear primary alcohols.
- Such C 8 -C 18 -linear primary alcohols are commercially available under the trade name Alfols, typical examples being Alfol (8-10), Alfol (9-11), Alfol (10-14), Alfol (12-13) and Alfol (16-18).
- Alfol is a registered trade mark.
- Preferred examples of compounds of formula (1) in which m is 1 include, e.g., polyadducts of 3-20 moles of ethylene oxide with 1 mole of a C 8 -C 18 -alkyl monoalcohol. Especially interesting are polyadducts of 3-20 moles of ethylene oxide with 1 mole of a C 11 -C 13 -oxoalcohol and polyadducts of 8-20 moles of ethylene oxide with 1 mole of a C 12 -C 14 -fatty alcohol.
- the radical R in the compounds of formula (1 ), when m is 2, is derived from a C 2 -C 4 alkylene glycol residue from which the two hydroxy groups have been removed. Examples of such C 2 -C 4 alkylene glycols include ethylene glycol, n-butylene glycol and, especially propylene glycol.
- Preferred examples of compounds of formula (1) in which m is 2 include, e.g., polyadducts of 2-20 moles of ethylene oxide with 1 mole of a C 2 -C 4 alkylene glycols, preferably polyethylene glycol ethers of propylene glycol, in particular those having the formula: in which x and y are each an integer within the range of from 1 to 10, preferably within the range of from 1 to 5, the sum of x and y preferably being about 10.
- the alkyl radical R in the compounds of formula (1), when m is 3, is derived from trimethylolpropane.
- Preferred examples of compounds of formula (1) in which m is 3 include polyadducts of 3-20 moles of ethylene oxide with 1 mole of trimethylolpropane. Especially interesting are polyadducts of 7-20 moles of ethylene oxide with 1 mole of trimethylolpropane.
- the alkyl radical R in the compounds of formula (1), when m is 4, is derived from pentaerythritol.
- Preferred examples of compounds of formula (1) in which m is 4 include polyadducts of 4-20 moles of ethylene oxide with 1 mole of pentaerythritol. Especially interesting are polyadducts of 5-20 moles of ethylene oxide with 1 mole of pentaerythritol.
- Mixtures of two or more of the compounds of formula (1) may be used as component c) of the formulation according to the present invention.
- the compounds of formula (2) to (12) are known and may be obtained by known methods.
- Optional auxiliaries which may be present in the formulation of the present invention include stabilisers which are effective in adjusting the flow properties of the formulation, anti-foam agents, alkaline agents, fabric softeners, anti-redeposition agents, antioxidants, auxiliary builders such as polyacrylic acid and fragrances.
- stabilisers examples include, e.g., kaolin, an Mg/Al silicate, especially bentonite, montmorillonite, a zeolite or a highly dispersed silicic acid.
- the formulation of the present invention may be produced by mixing fluorescent whitening agent, solvent and the compound of formula (1) together with any optional auxiliaries, and homogenising the the mixture so obtained, preferably at an elevated temperature, e.g. at 40-100°C. Mixing is conveniently effected by a suitable stirring device.
- the resulting formulation is normally a clear and stable solution. On occasion, however, it may be necessary to filter the formulation in order to remove minor amounts of Insoluble components.
- the formulation of the present invention is particularly suitable for incorporation into a dry detergent composition, conveniently by adding the required amount of the formulation of the present invention to a dry detergent composition and then homogenising the mixture so obtained.
- the formulation of the present invention may also be used, however, for the production of liquid detergents by adding the required amount of the formulation of the present invention to a liquid detergent composition and then homogenising the mixture so obtained.
- the suspension so obtained is heated, with stirring, to an internal temperature of 70-80°C. After 4-5 hours, an almost clear solution is obtained which contains less than 1% by weight of undissolved components.
- the solution is cooled to 40-50°C. and filtered.
- a clear yellow solution is obtained having an active substance content of 15% by weight, a water content of 25% by weight and a viscosity of 462 mPas.
- Example cpd. (10) presscake % by wt. water % by wt. parts of EO in adduct adduct % by weight Appearance of product at 25°C Viscosity mPas 2 30 15 9 55 slightly opalescent 505
- Example 2 Using the procedure described in Example 1, a liquid formulation is obtained which is a clear solution at 25°C. and has a viscosity of 397 mPas.
- Example 2 Using the procedure described in Example 1, a liquid formulation is obtained which is a clear solution at 25°C. and has a viscosity of 434 mPas.
- Example 2 Using the procedure described in Example 1, a liquid formulation is obtained which is a clear solution at 25°C. and has a viscosity of 550 mPas.
- Example 2 Using the procedure described in Example 1, a liquid formulation is obtained which is a clear solution at 25°C. and has a viscosity of 540 mPas.
- Example 7 Using the procedure described in Example 1, a liquid formulation (Example 7) is obtained which is a clear solution at 25°C. and has a viscosity of 1600 mPas.
- Example 11 Using the procedure described in Example 1, a liquid formulation (Example 11) is obtained which, after filtration, is a clear solution at 25°C. and has a viscosity of 732 mPas.
- Example 13 Using the procedure described in Example 1, a liquid formulation (Example 13; viscosity 807 mPas) is obtained which, after filtration, is a clear solution at 25°C.
- Example 15 Using the procedure described in Example 1, a liquid formulation (Example 15; viscosity less than 500 mPas) is obtained which is a clear solution at 25°C.
- Example 18 Using the procedure described in Example 1, a liquid formulation (Example 18; viscosity less than 500 mPas) is obtained which is a clear solution at 25°C.
- the suspension so obtained is heated, with stirring, to an internal temperature of 70-80°C. After 4-5 hours, an almost clear solution is obtained which contains less than 1% by weight of undissolved components.
- the solution is cooled to 50-60°C. and filtered.
- a clear yellow solution is obtained having an active substance content of 15% by weight, a water content of 25% by weight and a viscosity of 3000 mPas. The solution remains clear after standing for 2 days.
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- Chemical & Material Sciences (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)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9621421 | 1996-10-15 | ||
GB9621421A GB2318360A (en) | 1996-10-15 | 1996-10-15 | Fluorescent whitening agent formulation |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0837124A2 EP0837124A2 (en) | 1998-04-22 |
EP0837124A3 EP0837124A3 (en) | 1999-01-20 |
EP0837124B1 true EP0837124B1 (en) | 2003-12-03 |
Family
ID=10801404
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97810741A Expired - Lifetime EP0837124B1 (en) | 1996-10-15 | 1997-10-06 | Fluorescent whitening agent formulation |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0837124B1 (pt) |
JP (1) | JPH10152695A (pt) |
KR (1) | KR100503774B1 (pt) |
CN (1) | CN1165606C (pt) |
AU (1) | AU732991B2 (pt) |
BR (1) | BR9705030A (pt) |
DE (1) | DE69726544T2 (pt) |
ES (1) | ES2210486T3 (pt) |
GB (1) | GB2318360A (pt) |
ID (1) | ID18528A (pt) |
MX (1) | MX9707800A (pt) |
TW (1) | TW400379B (pt) |
ZA (1) | ZA979178B (pt) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA02000200A (es) | 1999-08-16 | 2002-06-21 | Ciba Sc Holding Ag | Formulacion de agente blanqueador fluorescente liquido. |
DE60308485T2 (de) * | 2002-02-25 | 2007-09-06 | Ciba Speciality Chemicals Holding Inc. | Prozess zum behandeln von textilen fasermaterialien |
AU2004274657A1 (en) * | 2003-09-19 | 2005-03-31 | Ciba Specialty Chemicals Holding Inc. | Aqueous solutions of fluorescent whitening agents |
KR100689260B1 (ko) * | 2005-05-24 | 2007-03-02 | 삼원산업주식회사 | 항산화성 스틸벤계 형광증백제 및 이의 합성방법 |
KR101421622B1 (ko) * | 2012-06-29 | 2014-07-23 | 삼원산업주식회사 | 항산화성 스틸벤계 형광증백의 합성방법 |
JP2017509774A (ja) * | 2014-01-20 | 2017-04-06 | ザ プロクター アンド ギャンブル カンパニー | 蛍光増白剤プレミックス |
CN104862120A (zh) * | 2015-04-09 | 2015-08-26 | 广州立白企业集团有限公司 | 一种洗涤剂用荧光增白剂水溶液的制备方法 |
CN105238099B (zh) * | 2015-10-12 | 2017-07-07 | 山西青山化工有限公司 | 一种增白皂用液体荧光增白剂及其制备方法 |
CN106087384A (zh) * | 2016-06-21 | 2016-11-09 | 太仓市东明化工有限公司 | 一种织物用耐水型荧光增白剂 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3953380A (en) * | 1970-10-28 | 1976-04-27 | Colgate-Palmolive Company | Liquid detergent |
US4298490A (en) * | 1978-12-22 | 1981-11-03 | Ciba-Geigy Corporation | Process for the production of washing powders of stabilized or enhanced appearance which contain fluorescent whitening agents |
US4661287A (en) * | 1983-10-05 | 1987-04-28 | Colgate-Palmolive Company | Stable soil release promoting enzymatic liquid detergent composition |
US4764302A (en) * | 1986-10-21 | 1988-08-16 | The Clorox Company | Thickening system for incorporating fluorescent whitening agents |
DE3878550D1 (de) * | 1987-11-27 | 1993-03-25 | Ciba Geigy Ag | Aufhellerdispersion. |
US5149463A (en) * | 1989-04-21 | 1992-09-22 | The Clorox Company | Thickened acidic liquid composition with sulfonate fwa useful as a bleaching agent vehicle |
EP0427670A1 (de) * | 1989-11-07 | 1991-05-15 | Ciba-Geigy Ag | Flüssigwaschmittel |
IT1237754B (it) * | 1989-11-08 | 1993-06-17 | Sigma Prodotti Chimici Srl | Composizione liquida di candeggiante ottico. |
CH682748A5 (de) * | 1991-11-07 | 1993-11-15 | Ciba Geigy Ag | Lagerstabile Formulierung von optischen Aufhellermischungen. |
KR0161894B1 (ko) * | 1991-11-08 | 1999-01-15 | 구자홍 | 스크롤 압축기 |
MY109837A (en) * | 1992-06-30 | 1997-08-30 | Ciba Specialty Chemicals Holding Inc | Hydrates of the disodium salt or dipotassium salt of 4, 4''-bis (2-sulfostyryl)bipheny] |
CH686959A5 (de) * | 1992-12-22 | 1996-08-15 | Ciba Geigy Ag | Lagerstabile Formulierung von optischen Aufhellern. |
US5425898A (en) * | 1993-09-27 | 1995-06-20 | The Clorox Company | Thickening system for incorporating fluorescent whitening agents |
GB9323250D0 (en) * | 1993-11-11 | 1994-01-05 | Unilever Plc | Process for the production of a detergent composition |
JPH07286198A (ja) * | 1994-04-15 | 1995-10-31 | Lion Corp | 粒状ノニオン洗剤組成物の製造方法 |
IT1270004B (it) * | 1994-09-23 | 1997-04-16 | 3V Sigma Spa | "formulazioni di candeggianti ottici" |
GB9509291D0 (en) * | 1995-05-06 | 1995-06-28 | Ciba Geigy Ag | Formulations |
-
1996
- 1996-10-15 GB GB9621421A patent/GB2318360A/en not_active Withdrawn
-
1997
- 1997-08-30 TW TW086112472A patent/TW400379B/zh not_active IP Right Cessation
- 1997-10-06 ES ES97810741T patent/ES2210486T3/es not_active Expired - Lifetime
- 1997-10-06 DE DE69726544T patent/DE69726544T2/de not_active Expired - Fee Related
- 1997-10-06 EP EP97810741A patent/EP0837124B1/en not_active Expired - Lifetime
- 1997-10-10 MX MX9707800A patent/MX9707800A/es active IP Right Grant
- 1997-10-14 AU AU41000/97A patent/AU732991B2/en not_active Ceased
- 1997-10-14 KR KR1019970052433A patent/KR100503774B1/ko not_active IP Right Cessation
- 1997-10-14 CN CNB971204411A patent/CN1165606C/zh not_active Expired - Fee Related
- 1997-10-14 BR BR9705030A patent/BR9705030A/pt not_active IP Right Cessation
- 1997-10-14 ZA ZA9709178A patent/ZA979178B/xx unknown
- 1997-10-14 ID IDP973434A patent/ID18528A/id unknown
- 1997-10-15 JP JP9280987A patent/JPH10152695A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
GB2318360A (en) | 1998-04-22 |
CN1165606C (zh) | 2004-09-08 |
JPH10152695A (ja) | 1998-06-09 |
KR19980032785A (ko) | 1998-07-25 |
BR9705030A (pt) | 1999-06-15 |
ES2210486T3 (es) | 2004-07-01 |
EP0837124A3 (en) | 1999-01-20 |
ZA979178B (en) | 1998-04-15 |
ID18528A (id) | 1998-04-16 |
DE69726544D1 (de) | 2004-01-15 |
AU4100097A (en) | 1998-04-23 |
AU732991B2 (en) | 2001-05-03 |
CN1179466A (zh) | 1998-04-22 |
DE69726544T2 (de) | 2004-09-30 |
TW400379B (en) | 2000-08-01 |
MX9707800A (es) | 1998-04-30 |
GB9621421D0 (en) | 1996-12-04 |
EP0837124A2 (en) | 1998-04-22 |
KR100503774B1 (ko) | 2005-10-13 |
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