WO2000011256A1 - Aqueous compositions of uv-active agents, their production and use - Google Patents

Aqueous compositions of uv-active agents, their production and use Download PDF

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Publication number
WO2000011256A1
WO2000011256A1 PCT/IB1999/001466 IB9901466W WO0011256A1 WO 2000011256 A1 WO2000011256 A1 WO 2000011256A1 IB 9901466 W IB9901466 W IB 9901466W WO 0011256 A1 WO0011256 A1 WO 0011256A1
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WO
WIPO (PCT)
Prior art keywords
ionogenic
alkyl
advantageously
aqueous
aqueous dispersion
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.)
Ceased
Application number
PCT/IB1999/001466
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English (en)
French (fr)
Inventor
Jürg Heller
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.)
Clariant International Ltd
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
Clariant Finance BVI Ltd
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.)
Filing date
Publication date
Application filed by Clariant International Ltd, Clariant Finance BVI Ltd filed Critical Clariant International Ltd
Priority to DE69923984T priority Critical patent/DE69923984T2/de
Priority to AT99936928T priority patent/ATE290117T1/de
Priority to JP2000566501A priority patent/JP2002523561A/ja
Priority to EP99936928A priority patent/EP1115937B1/en
Priority to BRPI9913241-9A priority patent/BR9913241B1/pt
Priority to US09/763,506 priority patent/US6723256B1/en
Priority to ES99936928T priority patent/ES2238845T3/es
Publication of WO2000011256A1 publication Critical patent/WO2000011256A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • Textile material which is used in an environment in which ultraviolet (UV) light acts on the textile mate ⁇ al, especially UV light filtering through glass, as for the interior fittings m automobiles (carpets, belts, trim and seat covers), shop windows or glass-enclosed verandas (wall-to-wall carpets), are advantageously finished with a UV absorber in order that the fibres, especially synthetic and semisynthetic fibres, and the dyeings too to some extent, may be protected against the damaging action of the UV rays
  • a preferred procedure for textile mate ⁇ al used m an environment with filtered UV light involves applying the UV absorbers to the substrate, m particular to the fabrics or to the yarns, together with the respective dyes
  • Examples of technically preferred methods are batch methods, very particularly those in which the treatment liquors are subjected to a pronounced dynamic stress, for example for piece goods (particularly m rope or tube form) the dyemg m jet dyemg machines or for yarns the dyemg in the form of cheeses, or continuous methods whereby
  • EP-A-468921, 474595 and 490819 desc ⁇ be certain aqueous UV-absorber dispersions containing UV- absorbers and anionic surface active compounds or non-ionogenic and anionic surface active compounds and also such dispersions additionally containing a polysaccharide or a linear polymeric compound as a stabiliser and/or thickening agent.
  • EP-A-328485 describes aqueous dispersions of certain dyes, optical brighteners or UV-absorbers containing, besides dispersant, an alkylene-bisamide defoamer and m some examples also a linear polymer (polyvinyl alcohol or a propyleneoxide/- ethyleneoxide 3000 blockpolymer) or a polysaccharide.
  • EP-A-44995 desc ⁇ bes aqueous dispersions of optical brighteners containing a grafted polymer of certain vinyhc monomers
  • the invention relates to the defined compositions, their production and their use
  • the invention accordingly provides aqueous dispersions (U) containing.
  • (B x ) a non-ionogenic polyme ⁇ c hydrophilic dispersant or a mixture of such dispersants and (B ⁇ ) a non-ionogenic or anionic vinyl-polymeric hydrophilic thickener or a mixture of such thickeners.
  • the UV-hght-absorbing textile treatment agents (A) are UV-active agents, I e their fundamental property is the absorbing of UV light, whether to convert it at least partially into visible wavelengths, as in the case of optical brighteners, or to convert it at least partially mto other energy forms or other wavelengths, as is the case with typical UV absorbers.
  • the UV-active agents (A) are in particular
  • UV absorbers or (A 2 ) optical brighteners are in particular those which are dispersible in water m a manner known per se, i.e. with the aid of dispersants aqueous dispersions of (A) may be prepared which can then be used in accordance with the particular intended purpose.
  • Suitable UV absorbers (A]) include generally known substances as are usually employed for the UV- absorbmg finishing of synthetic and semisynthetic textile fibres from an aqueous dispersion, chiefly those of the benzophenone, t ⁇ azine or benzot ⁇ azole series, in particular phenols which bear a substituent of the t ⁇ azine, benzoyl or benzot ⁇ azole series in ortho-position relative to the hydroxyl group and which may bear further substituents, in particular non-chromopho ⁇ c and non-water- solublihzing substituents.
  • Suitable UV absorbers of the benzophenone series include generally 2-hydroxybenzophenones in which the two benzene rings may optionally be substituted with substituents customary in UV absorbers in particular with non-chromopho ⁇ c and non-water-solubilizmg substituents, for example with hydroxyl, alkyl, alkoxy, aryl, aryloxy, aralkoxy or halogen, aryl (in aryl, aryloxy and aralkoxy) being naphthyl or preferably phenyl, the alkyl and alkoxy radicals containing for example 1 to 4 carbon atoms, phenyl as aryl optionally being further substituted with alkyl, halogen and/or alkoxy, and halogen signifying preferably chlorine, and the alkoxy bridge in aralkoxy containing e.g. 1 or 2 carbon atoms.
  • Ri signifies hydrogen, hydroxyl, phenoxy, aralkoxy or . ⁇ -alkoxy
  • R 2 signifies hydrogen, halogen or C -alkyl
  • R signifies hydrogen or hydroxyl
  • R4 signifies hydrogen, hydroxyl, phenoxy, aralkoxy or C -alkoxy
  • R 5 signifies hydrogen or C 1 ⁇ -alkyl
  • R ⁇ signifies hydrogen or and X signifies a hydrocarbon b ⁇ dge member having 2 to 12 carbon atoms or hydroxyalkylene
  • R 2 , R 3 and R stand each preferably for hydrogen
  • R t preferably stands for hydrogen, hydroxyl, phenoxy or C
  • the two substituents R 5 and R Q are advantageously in the positions ortho and para to the carbonyl group.
  • R 5 and also R Q signify hydrogen
  • X stands for hydroxyalkylene, it advantageously contains at least 3 carbon atoms and the hydroxyl group is advantageously not attached to the first or last carbon atom of the b ⁇ dge.
  • X may e.g stand for 1 ,4-phenylene, 1 ,4- naphthylene or C 2-4 -alkylene or also for 2-hydroxy-l,3-propylene.
  • Suitable UV-absorbers of the t ⁇ azme series include in general 2-(2'-hydroxyphenyl)-s-t ⁇ az ⁇ nes in which the positions 4 and 6 are substituted with hydrocarbon radicals which in turn may be further substituted, in which case the substituents are neither chromophoric nor water-solubihzing
  • the hydrocarbon radicals in 4-pos ⁇ t ⁇ on and in 6-pos ⁇ t ⁇ on are for example aryl, alkyl or aralkyl, aryl standing e g. for naphthyl or preferably phenyl, aralkyl standing preferably for benzyl and alkyl containing e g 1 to 18 carbon atoms.
  • the substituents occurring on phenyl rings are for example hydroxyl, halogen, low molecular weight alkyl, alkoxy or alkylthio, and the substituents occu ⁇ ing on the alkyl radicals are for example hydroxyl, low molecular weight alkoxy, alkylthio or dialkylamino
  • 2-(2'-hydroxyphenyl)-s-t ⁇ az ⁇ nes of the following formula
  • R 7 signifies hydroxyl, halogen
  • R 8 signifies C I-lg -alkyl, which is optionally substituted with hydroxyl, halogen, C ]-4 -alkoxy, or d ⁇ -(C 1-4 -alkyl)-am ⁇ no, or phenyl, which is optionally substituted with hydroxyl, halogen, C -alkyl or C -alkoxy
  • R 9 signifies C ]-t 8 -alkyl, which is optionally substituted with hydroxyl, halogen, C -alkoxy, C ⁇ _ -alkylth ⁇ o or d ⁇ -(C ⁇ _ 4 -alkyl)-am ⁇ no, or phenyl, which is optionally substituted with hydroxyl, halogen, C -alkyl or C -alkoxy
  • m signifies 0, 1 or 2.
  • alkyl radicals which occur may be linear or, if they contain three or more carbon atoms, may also be branched or, if they contain six or more carbon atoms, may also be cyclic.
  • R 7 stands preferably for chlorine or C )-4 -alkyl.
  • m signifies 2
  • the two R 7 substituents may have equal or different significances, m which latter case it is preferable for the second R 7 to signify methyl.
  • one R 7 is preferably in para-position relative to the 2-pos ⁇ t ⁇ oned hydroxyl group.
  • Suitable UV absorbers of the benzot ⁇ azole se ⁇ es include generally 2-(2'-hydroxyphenyl)-benzo- t ⁇ azoles wherein the two benzene rings may optionally be substituted in particular with substituents customary in UV absorbers, in particular non-chromopho ⁇ c and non-water-solubihzing substituents, e.g.
  • Rio signifies C ⁇ . ]2 -alkyl, C,. 5 -alkoxy, aryl, aralkyl, (C
  • alkyl radicals which occur may be linear or, if they contain three or more carbon atoms, may also be branched or, if they contain six or more carbon atoms, may also be cyclic.
  • Aralkyl stands preferably for benzyl.
  • Halogen stands preferably for chlorine.
  • the position 6 is preferably unsubstituted; m the benzot ⁇ azole ring, the positions 4 and 7 are preferably unsubstituted
  • UV absorbers of the benzot ⁇ azole series conform to the formula
  • R' signifies hydrogen, C ⁇ _ 5 -alkyl, C ⁇ _ 5 -alkoxy, (C]_ 5 -alkoxy)-carbonyl or chlorine,
  • R" signifies hydrogen or chlorine
  • R' signifies hydrogen, C M2 -alkyl, phenyl, (C ⁇ . 5 -alkyl)-phenyl, benzyl or chlorine,
  • R" signifies hydrogen, hydroxyl, C ⁇ . 5 -alkyl, C). 5 -alkoxy or chlorine, and Rio' signifies Ci. ⁇ -alkyl, C ⁇ _ 5 -alkoxy, phenyl, (C ⁇ 5 -alkyl)-phenyl, benzyl, (C ⁇ _ 5 -alkoxy)- -carbonyl or chlo ⁇ ne,
  • Ro signifies C ⁇ _ 5 -alkyl, C). 5 -alkoxy or chlorine, preferably C ⁇ _ 5 -alkyl,
  • Ro' signifies hydrogen, chlo ⁇ ne, C ⁇ -alkyl or C ⁇ . 5 -alkoxy, preferably hydrogen or C ⁇ _ 5 -alkyl
  • R " signifies hydrogen, chlo ⁇ ne, .s-alkyl or C ⁇ _ 5 -alkoxy, preferably hydrogen, chlorine or methyl.
  • Useful optical brighteners (A 2 ) are generally l nown substances of the type usually employed for the optical brightening of synthetic and semisynthetic textile fibres from an aqueous dispersion, in particular those of the coumarin, naphthalimide, benzoxazole, stilbene, bisstyrylbenzene, thiophene or pyrene series and which may bear any substituents usual in the case of optical b ⁇ ghteners, especially non-chromopho ⁇ c and non-water-solubihzing substituents.
  • Suitable optical b ⁇ ghteners (A 2 ) are for example those of the following formulae (V) to (XI)
  • Ri 2 signifies C ⁇ -alkyl and R i3 signifies hydrogen or C ⁇ -alkoxy
  • R signifies hydrogen, chlo ⁇ ne or C ⁇ _ -alkyl
  • Ri 5 signifies hydrogen or Ci ⁇ t -alkyl
  • Y signifies a radical of the formula
  • R ]6 signifies hydrogen or C 1- -alkyl
  • R 17 signifies hydrogen, chlorine or
  • Rig signifies -CN, (C 1- -alkoxy)-carbonyl, phenyl or a radical of the formula
  • R 2 o signifies -CN or (C ⁇ - -alkoxy)-carbonyl
  • R 2 ⁇ signifies hydrogen, chlorine, -CN or C ⁇ _ -alkyl
  • R 22 signifies 1-pyrazolyl which is substituted with chlorine or C M -alkyl in position 3 or 4, or signifies phenyl and R 23 signifies 2-t ⁇ azolyl or 1-pyrazolyl which are substituted with C ⁇ . -alkyl and/or phenyl or signifies 2-naphthot ⁇ azolyl,
  • R 2 signifies C 1- -alkyl and R 25 signifies C ⁇ _ 4 -alkyl
  • the dispersant system (B) is used for dispersing the UV-active textile treatment agents (A) in water to obtain dispersions (U) having the above-indicated properties. It contains the polymeric components (B x ) and (B ⁇ ) and may optionally cotam further surfactants and/or auxiha ⁇ es, especially
  • the non-ionogenic dispersants B x are hydrophilic. They are in particular polymers containing a polyme ⁇ c lipophihc base structure and hydrophilic polyethylene glycol ether chains.
  • they are polycondensates of phenolic compounds with formaldehyde to form corresponding novolaks in which the polyethylene glycol ether chains can be introduced before or after the polycondensation and may, if desired, be partly or wholly capped by alkylation Suitable starting phenols are unsubstituted phenol or phenol substituted with lower alkyl or alkoxy, alkyl preferably being methyl or ethyl and alkoxy is preferably being methoxy.
  • the positions ortho and para relative to the hydroxyl group are advantageously unsubstituted; when the phenol thus bears such a substituent, this is preferably in position meta to the hydroxyl group; when the phenol bears two substituents, these are preferably in the two m-positions
  • phenol, m-cresol, 3-ethylphenol, 3-methoxyphenol and 3,5- dimethylphenol of which unsubstituted phenol is preferred
  • the phenolic compounds may be oxyethylated with ethylene oxide before or also after the condensation with formaldehyde
  • the condensation with formaldehyde is advantageously carried out using such a molar ratio of formaldehyde/phenolic compound as to produce a crosslinked polymer, for example a molar ratio of formaldehyde/phenolic compound of > 1.2/1, preferably m the range from 1.4/1 to 2 5/1, particularly preferably 1.6/1 to 2.3/1
  • This capping in particular the ethe ⁇ fication, may be earned out partially or completely, preferably to an extent of not less than 80 mol-%, especially not less than 95 mol-%, particularly preferably exhaustively
  • the oxyethylation (whether before or after the formaldehyde condensation) is advantageously earned on to such a degree that the product (B x ) has a distinctly hydrophilic character in that the HLB is advantageously ⁇ 16; the HLB is particularly > 8, preferably > 10, particularly preferably in the range from 12 to 16
  • the thickeners (B ⁇ ) are hydrophilic polymers of vinyl compounds; they have an anionic or non- lonogenic character and may optionally be crosslinked.
  • the anionic polymers (B ⁇ ) are preferably carboxyl-contaimng polymers. As thickeners (B ⁇ ) chiefly the following may be mentioned
  • (B Y2 ) a non-ionogenic (co)polymer essentially free from hydrogen bonded to hetero atoms and (B Y3 ) a polyvinyl alcohol or a mixture of two or more thereof.
  • the copolymers (B Y] ) are carboxyl-contaimng and crosslinked. They may be prepared in a manner conventional per se, by copolyme ⁇ zation of corresponding monomers which contain an ethylenic double bond, of which at least a portion are carboxyl-contaimng monomers and at least a portion is a crosshnking comonomer Non-ionogenic comonomers may also have been incorporated in the polymer, if desired
  • the carboxyl-contaimng monomers are advantageously carboxyl-contaimng monomers which contain at least two carboxyl groups and 4 to 6 carbon atoms and are preferably used as anhydride, especially as cyclic dicarboxyhc anhydride, for example itaconic acid or especially maleic acid or respectively its anhydride.
  • the monomers or comonomers prefe ⁇ ed for preparing (B Y1 ) are in particular
  • (B Y12 ) at least one monoethylenically unsaturated non-ionogenic comonomer and (B Y)3 ) a crosshnking comonomer, and (B ⁇ ) is preferably a copolymer of (B Y n), (B Y!2 ) and (B Y ⁇ 3 ).
  • comonomers (B Y]2 ) are chiefly suitable low molecular weight compounds, especially alkyl (meth)acrylates wherein alkyl advantageously contains 1 to 4 carbon atoms and preferably is methyl or ethyl, alkyl vinyl ethers wherein alkyl advantageously contains 1 to 4 carbon atoms and is preferably methyl, vinyl esters of low molecular weight aliphatic carboxyhc acids, in particular of those having 2 to 4 carbon atoms, chiefly vinyl acetate or vinyl propionate, and/or vinylpy ⁇ ohdone
  • crosshnking comonomers are suitable especially non-ionogenic compounds which contain at least two mutually unconjugated ethylenic double bonds, advantageously at least two terminal double bonds, for example N,N'-methylened ⁇ acrylam ⁇ de, ⁇ , ⁇ -alkaned ⁇ anes having 5 to 12 carbon atoms or divinyl ethers of ⁇ , ⁇ -alkaned ⁇ ols having for example 2 to 12 carbon atoms in the alkane moiety or of polyethylene glycols, or also divinylbenzene.
  • the ⁇ , ⁇ - alkanedienes are prefe ⁇ ed.
  • the molar ratio (B YU )/(B Y12 )/(B Y i 3 ) is advantageously in the range of 1/(0.2-3)7(0.0001-0.01), preferably 1/(0.5- 1.8)7(0.0004-0.004), particularly preferably 1/(0.8-1.2)7(0.0004-0.001).
  • the copolymers (B Y) ) are known or can be prepared analogously to known methods, expediently in the presence of a suitable initiator of free-radical polyme ⁇ zation [e.g. azobisisobutyronit ⁇ le, benzoyl peroxide, acetylbenzoyl peroxide, di-t.butyl peroxide, t.butyl peroxypivalate, azob ⁇ s-(2,4-d ⁇ methyl- valeronit ⁇ le), for example in concentrations of from 0.001 to 1 %] and advantageously in the presence of a suitable aprotic solvent, for example benzene, toluene, xylene, acetone, methyl ethyl ketone, methylene chloride, cyclohexane and/or ethyl acetate; it is particularly advantageous to use a mixture of cyclohexane and ethyl acetate.
  • the polymerization is advantageously carried out at temperatures in the range from 50 to 100°C, preferably in the range from 60 to 80°C.
  • the production of the polymer is advantageously earned out in such a way that crosshnking takes place lntramolecularly at least to some extent, especially in such a way that the linear sequence of the monomers forms loops m the course of the polymerization owing to the copolyme ⁇ zed crosshnking monomer (B Y]3 )
  • the carboxyl- contaimng monomer, especially (B Y n) is advantageously used in the form of the anhydride, especially maleic anhydride, the polymer (B Y ⁇ ') prepared therefrom still contains the anhydride groups
  • This polymer (B ⁇ ,') may, after completion of the polymerization and removal of the solvent, be hydrolyzed to the carboxyl-contaimng polymer (B Y) ) in salt form. In a prefe ⁇ ed process,
  • the polymers (B Y) ') and (B Y] ) may be produced for example by the process described in US 5024779, the content of this US Patent is incorporated herein by reference
  • Thickeners (B Y2 ) are chiefly thickeners which are essentially linear and essentially free from hydrogen attached to hetero atoms, in particular free from hydroxyl groups and -CONH groups Suitable monomers are in particular vinyl compounds which contain cyclic or disubstituted amide groups or which contain ester groups.
  • the thickeners (B Y2 ) are for example polyvmylpy ⁇ ohdones (having for example an average molecular weight in the range from 10000 to 200000) or preferably copolymers of
  • Suitable (B Y22 ) are in particular vinyl acetate and preferably vinyl propionate.
  • the molar ratio of (B ⁇ 2 i) : (B ⁇ 22 ) 1S f° r example in the range from 10: 1 to 1: 10, preferably 5:1 to 1 :3, especially 4: 1 to 1 : 1
  • the molecular weight is advantageously in such a range that the polymer is swellable, for example in the range from 5000 to 5000000, advantageously 20000 to 2000000, preferably 100000 to 1500000
  • Such copolymers are generally known or preparable analogously to known methods
  • (B Y3 ) are suitable generally polyvmyl alcohols and copolymers thereof with vinyl acetate comonomers or partial hydrolysates of co ⁇ esponding polyvmyl acetates.
  • (B Y3 ) is a polyvinyl alcohol whose 4 % aqueous solution has a viscosity (to DIN 53015) at 20°C which is for example in the range from 2.5 to 70 cP, advantageously 2.5 to 40 cP, preferably 2.5 to 30 cP.
  • the weight ratio of (B X )/(B Y ) is advantageously in the range from 0.01/1 to 10/1, preferably 0 05/1 to 4/1, especially 0.1/1 to 1/1; the weight ratio of (B X )/(A) is advantageously within the range from 1/100 to 80/100, preferably 2/100 to 20/100, especially 3/100 to 10/100; and the weight ratio of (B Y )/(A) is advantageously in the range from 0.1/100 to 120/100, preferably 0.2/100 to 60/100, especially 0 5/100 to 40/100.
  • (B ⁇ ) there may be used one or more of the components (B Y
  • the weight ratio of (B Y) )/(A) is advantageously in the range from 0.05/100 to 0.5/100, preferably 0.1/100 to 1.3/100; when (B Y2 ) is used, the weight ratio of (B Y2 )/(A) is advantageously m the range from 1/100 to 30/100, advantageously 2/100 to 20/100; when (B Y3 ) is used, the weight ratio of (B Y3 )/(A) is advantageously in the range from 2/100 to 120/100, preferably 5/100 to 50/100, the weight ratio of (B Y3 )/(A) being advantageously in the range from 2/100 to 35/100 if also at least one of (B Y1 ) and (B Y2 ) is present.
  • the surfactants (B z ) are surfactants which are suitable for supporting the dispersing effect of (B x ) in the presence of (B ⁇ ) and optionally (B w ), they are distinctly hydrophilic and also encompass such surfactants as are known in the art for example as wetting agents, detergents or emulsifiers.
  • (B z ) comprises
  • any amon-active surfactants of high hydrophihcity in particular compounds of distinctly anionic character which contain at least one lipophihc radical, in particular at least one lipophihc hydrocarbon radical, and at least one distinctly anionic group (sulpho group, phosphoric acid group or carboxyl group), the lipophihc hydrocarbon radical advantageously containing at least 9 carbon atoms, for example 9 to 30 carbon atoms
  • the lipophihc hydrocarbon radical advantageously containing at least 9 carbon atoms, for example 9 to 30 carbon atoms
  • condensation products of formaldehyde with sulphonated aromatic compounds for example sulphonated naphthalene, mono- or d ⁇ -(C 1- _alkyl)-naphthalene, biphenyl, diphenyl ether, ditolyl ether, phenol, C ⁇ -4 -alkylphenol and/or co ⁇ espondmg sulphones
  • sulphonated aromatic compounds for example sulphonated naphthalene, mono- or d ⁇ -(C 1- _alkyl)-naphthalene, biphenyl, diphenyl ether, ditolyl ether, phenol, C ⁇ -4 -alkylphenol and/or co ⁇ espondmg sulphones
  • hgninsulphonate optionally in a mixture with dihydroxydiphenyl sulphone, hgninsulphonates
  • C( 2 24 -alkyl sulphonates particularly n- or ⁇ so-C ⁇ 2 .
  • 24 -alkyl sulphonates sulphonation products of paraffins (prepared for example by sulphochlorination or sulphoxidation), of ⁇ -olefins, of alkylbenzenes and of unsaturated fatty acids,
  • the anionic surfactants are advantageously present, at least partly, in the form of salts, chiefly in the form of alkali metal salts (preferably sodium or potassium salts) or ammonium salts It is possible to use single compounds or also mixtures of compounds, including especially technical grade mixtures
  • non-ionogenic surfactants (B Z2 ) there may be employed distinctly hydrophilic surfactants, especially those which act as cosurfactants to (B Z1 )
  • hydrophilic surfactants especially those which act as cosurfactants to (B Z1 )
  • Generally known substances are suitable, p ⁇ ncipally those containing 9 to 30, preferably 12 to 24, carbon atoms in the lipophihc moiety and whose hydrophilic moieties contain ethylene glycol radicals, glycerol radicals and/or sorbitan radicals
  • ethylene glycol radicals glycerol radicals and/or sorbitan radicals
  • adducts of ethylene oxide to fatty alcohols including for example oxo alcohols), alkylphenols, di- or tnstyrylphenols or fatty acid N,N-d ⁇ ethanolam ⁇ de or diisopropanolamide; fatty acid monoesters of polyethylene glycols.
  • Polypropylene glycol chains may occasionally also occur in the molecule as lipophihc radicals, and accordingly the non-ionogenic surfactants used can also comprise block copolymers which contain propyleneoxy and ethyleneoxy units, and also optionally styreneoxy and/or butyleneoxy units (for example those known under the designation "Pluronic").
  • the HLB value of the non-ionogenic surfactants (B Z2 ) is advantageously > 8, preferably > 10, m particular in the range from 12 to 18, preferably 12 to 15, while those having an HLB value > 15, preferably > 16, may also be used as protective colloids.
  • the surfactants (B z ) are advantageously chosen so that they will assist and/or complete the dispersing effect of (B x ) in the presence of (B ⁇ ) and optionally (Bw)- Of the surfactants (B z ), the anionic ones are preferred, especially the aliphatic hydrocarbon sulphonates (B Z ⁇ ').
  • At least one anionic surfactant (B Z ⁇ ) is employed, optionally in the presence of a cosurfactant (B Z2 ).
  • the weight ratio of (B Z ⁇ )/(B z2 ) is for example m the range from 30/70 to 100/0
  • there are not employed any non-ionogenic surfactants (B Z2 ) or only minor amounts thereof are employed, for example 0 to 40 %, preferably 0 to 20 %, of (B Z2 ), based on (B Z ⁇ ).
  • the weight ratio of (B Z2 )/(B Z) ) is advantageously 1/100 to 40/100, preferably 5/100 to 20/100.
  • the employed or respectively suitable amount of (B Z ) can vary widely, especially depending on the kind and amount of the other components (B x ), (B ⁇ ) and any dispersing auxiliary (B w ) optionally added.
  • the amount of (B Z ) may be 2 to 70 % by weight of (B), preferably 5 to 50 % by weight of (B).
  • Dispersing auxiliaries (B w ) may optionally be employed in addition in order that the dispersing effect of (B x ) and optionally (B Z ) in the presence of (B ⁇ ) may be sustained and/or the appearance of the dispersion improved.
  • polyme ⁇ c protective colloids (B W ⁇ ) may be employed which differ from the abovementioned polymers; preferably (B W ⁇ ) is at least one non-ionogenic and/or anionic protective colloid.
  • Suitable polymenc protective colloids (B W ⁇ ) include known substances which - in contrast to the surface-active protective colloids of high hydrophihcity mentioned above under (B Z2 ) - have the character of polymers capable of forming a protective sheath around the dispersed colloid particles
  • the addition of a protective colloid (B W ⁇ ) may optionally also additionally influence the storage and transport stability of (U).
  • polysaccha ⁇ des polysaccharide derivatives, (co)poly(meth)acryhc acids and also protective colloids which are also useful as thickening substances, for example polyethylene glycols having for example an average molecular weight m the range from 200 to 10000, chiefly 300 to 6000, xanthan gum, cellulose gum, guar gum, dext ⁇ ns, gum arable, carboxymethylcellulose and acrylic-modified polysaccha ⁇ des
  • the acid groups particularly the carboxyhc acid groups, are at least partly present in the form of salts (so that the respective products are water-soluble), for example as alkali metal salts (chiefly sodium salts).
  • protective colloids B W ⁇
  • they are advantageously used in such amounts that the viscosity of the aqueous concentrated dispersion is ⁇ 1000 mPa-s, especially
  • the weight ratio of (B WI )/(A) is for example in the range from 1/100 to 200/100, preferably 2/100 to 150/100
  • (B W ) may be any wetting agent known per se, preferably at least one non-ionogenic or anionic wetting agent
  • non-ionogenic wetting agents come generally into consideration surfactants of the abovementioned categories which, however, have a co ⁇ espondingly lower HLB value or contain a co ⁇ espondingly lower number of added ethyleneoxy units
  • anionic wetting agents there may be mentioned e g mono- and dialkyl esters of sulphosuccmic acid
  • the anionic groups, analogously as described above for (B Z] ) may advantageously be present as alkali metal salts or ammonium salts
  • wetting agents (B W2 ) are possible; however, very effective dispersions can be prepared even without such wetting agents If a wetting agent is used, the weight ratio of (B W2 )/(A) is for example
  • solubihzers (B W3 ) may be used, in particular non-ionogenic solubihzers, for example mono-, di- or ohgoethylene glycols or their mono- or d ⁇ -(C -alkyl) ethers or glycerol
  • a solubihzer (B W ) may optionally be used. However, very good dispersions can be prepared even without solubihzer If a solubihzer is used, the weight ratio of (B W3 )/(A) is advantageously ⁇ 10/100, for example in the range from 1/100 to 8/100.
  • the dispersing system may, if desired, include still further surfactants and dispersing auxiliaries, but preferably it contains no further components in addition to the abovementioned (B x ) and (B ⁇ ) and optionally (B Z ) and/or (B w )
  • (B) consists essentially of the mentioned (B ) and (B ⁇ ) and optionally (B z ) and/or (B w )
  • the weight ratio of the total components (B x ) + (B ⁇ ) + (B z ) to (A) is advantageously in the range from 5/100 to 150/100, preferably 6/100 to 80/100, particularly preferably 10/100 to 70/100.
  • the weight ratio of the total dispersing system (B) to (A) is for example in the range from 5/100 to 250/100, advantageously in the range from 10/100 to 150/100, preferably 20/100 to 150/100
  • the weight ratio of the total dispersing system (B) to (A) is for example in the range from 5/100 to 80/100, advantageously in the range from 10/100 to 60/100, preferably 15/100 to 50/100
  • the products (A) and (B) may be used in pu ⁇ fied or unpu ⁇ fied form, i.e. the aqueous dispersions (U) may optionally also include
  • the aqueous dispersions (U) may optionally include further additives, especially
  • composition additives (D) at least one formulation additive and/or (E) at least one agent for setting the pH.
  • the further formulation additives (D) may optionally be used, for example to further adapt the properties of the dispersions (U) to particular requirements or wishes concerning transport, storage and/or use.
  • Such additives are m particular at least one of the following:
  • defoamers are suitable as (Di), for example paraffins or mineral oils in dispersed form, sihcone defoamers, silica, ethylenebisstearamide and/or mixtures of two or more thereof
  • Commercially available products may be used in particular.
  • the amounts of defoamer which can be used in the compositions of the invention are in the ranges conventional per seand are m general dependent on the nature and amount of the surfactants. In general, very small amounts of defoamer are sufficient, e g ⁇ 1 % by weight, especially 0.01 to 0 4 % by weight, based on the entire aqueous composition (U)
  • components (D 2 ) are suitable in general known substances, essentially fungi- or bacte ⁇ ostatic substances and or microbicides, as are commercially available, and the concentrations used may conform to those recommended for each, for example ⁇ 1 % by weight, particularly 0.01 to 0 4 % by weight, based on the entire aqueous dispersion (U).
  • a component (D 3 ) may also be employed (D 3 ) is advantageously a disperse dye of the type usable in general for shading disperse brighteners
  • Disperse dyes are a generally known category of dyes and are known in the art and extensively described in the technical literature, for example in the Colour Index Suitable components (D 3 ) include any disperse dyes which possess a colour suitable for shading optical brighteners, for example blue, violet and red disperse dyes.
  • the pH of the dispersion may e.g. be set to values in the range from 3.5 to 8, preferably 4 to 7.
  • Prefe ⁇ ed aqueous dispersions (U) of the invention are those which consist essentially of (A), (B) and water and optionally at least one of the components (C), (D) and (E).
  • the (A) content of the concentrated aqueous dispersions (U) is for example in the range from 2 to 50 % by weight, advantageously 5 to 45 % by weight, preferably 10 to 40 % by weight.
  • the water content of the concentrated aqueous dispersions (U) of the invention is advantageously in the range from 90 to 30 %, preferably 70 to 33 %, by weight.
  • the dispersions (U) of the invention can be produced as described above, in particular with grinding, wherein with the aid of suitable mills, for example ball mills or bead mills (glass or porcelain beads), the dispersed particles may be ground to a particle size of the desired fineness, and, if desired, a portion of the components, particularly of the water-soluble or else water-thmnable components, particularly for example (B W ⁇ ), (B ), (D 2 ) and/or (D 3 ), may also not be mixed in until after the grinding.
  • suitable mills for example ball mills or bead mills (glass or porcelain beads
  • suitable mills for example ball mills or bead mills (glass or porcelain beads
  • the dispersed particles may be ground to a particle size of the desired fineness, and, if desired, a portion of the components, particularly of the water-soluble or else water-thmnable components, particularly for example (B W ⁇ ), (B ), (D 2 ) and/or (D 3 ), may also
  • the average particle size of the dispersed particles in the dispersions (U) of the invention is advantageously in the range from 0.05 to 10 ⁇ m, preferably 0.2 to 6 ⁇ m, particularly preferably 0.4 to 4 ⁇ m
  • the dispersions are filtered through a suitable sieve or a suitable filter in such a way that the dispersed particles are not larger than 20 ⁇ m, preferably not larger than 10 ⁇ m, particularly preferably not larger than 6 ⁇ m
  • the amount of water employed is m principle freely choosable; advantageously, sufficient water is added for the dispersion to be stinable and pourable or respectively pumpable.
  • the amount of water present in the dispersion is advantageously such that the concentration of (A) in (U) is e.g. 2 to 50 % by weight, preferably 5 to 45 % by weight
  • More dilute dispersions are e.g. application liquors and stock dispersions which may optionally also contain further application-dictated additives Concentrated to dilute dispersions may thus be produced, e.g. those having an (A) content in the range from 0.01 to 50 % by weight.
  • the (A) concentrations are e.g.
  • m stock dispersions e.g. 0.1 to 20 % by weight, preferably from 0.5 to 10 % by weight, in concentrated dispersions e g. 5 to 45 % by weight, preferably 10 to 40 % by weight
  • the concentrated dispersions (U) are a particular aspect of the invention
  • the aqueous dispersions (U) prepared as described herein, even the concentrated ones, are surprisingly stable and flowable (in particular liquid).
  • the concentrated dispersions have in particular a viscosity which is ⁇ 1000 mPa-s; preferably, they have a viscosity in the range from 20 to 300 mPa-s, preferably 50 to 200 mPa-s, so that they are also efficiently pumpable. They may be handled, stored and/or transported and also be used directly for metered addition, so as they have been prepared. They are notable for surprisingly good stability in storage and transport.
  • the dispersions (U) of the invention serve for the co ⁇ esponding UV-active finishing of textile matenal, in particular textile material which can be dyed with disperse dyes or optically brightened with disperse brighteners.
  • Suitable textile matenal includes m particular textile mate ⁇ al composed of synthetic and semisynthetic materials, chiefly of polyester, polyamides, polyurethanes and cellulose acetates, and also of fibre blends comprising such synthetic or semisynthetic materials (e.g polyester/cotton, polyester/viscose, polyester/cotton/elastane).
  • the textile material may be in any desirable processed state suitable for the particular application, for example in the form of loose fibres filaments, yarns, hanks, wovens, knits, carpets, ready-made and half-ready-made goods.
  • Particular preference is given to using the dispersions (U) of the invention in the HT dyeing of yarns, which are wound on packages, especially in the form of cheeses, or in the optical brightening by the HT or thermosol processes
  • the dispersions (U) of the invention are highly compatible with disperse dyes (F) and, when (A) is a UV absorber (A)), are advantageously formulated together with a suitable disperse dye (F) to form an aqueous liquor which includes both the disperse dye (F) and the UV absorber (A,)
  • the disperse dye (F) may be any desired disperse dye or disperse dye mixture as are otherwise used for dyeing synthetic or semisynthetic textile material. Disperse dyes are generally known and extensively described in the technical literature, for example in the Colour Index under the heading "Disperse Dyes".
  • Disperse dyes are generally formulated with suitable dispersants in order that they may be dispersed in the dyeing liquor; the dispersants used for this purpose are usually anionic and optionally non-ionogenic dispersants, for example such as described under (Bi). Disperse dyes formulated in this way customarily include 30 to 60 % of dye and about 70 to 40 % by weight of dispersant besides, optionally, traces of by-products.
  • (A) is an optical bnghtener (A 2 )
  • (A 2 ) When (A) is an optical bnghtener (A 2 ), generally either no dyes will be employed at all or dyes will be employed as described under (D 3 ) for shading.
  • concentrations of dyes (F) m the respective liquor may vary within wide limits, depending on the substrate, the choice of dyeing method and the choice of depth of shade.
  • concentration of (U) in the liquor is generally dependent on the nature and the content of (A) and on the desired UV-active effect Concentrations are employed, for example, such that the concentration of (A]) based on the substrate is in the range from 0.1 to 4 % by weight, preferably 0.2 to 2 % by weight.
  • the concentration of (A 2 ) based on the substrate is advantageously chosen so as to obtain a good white effect and may also vary according to substrate, application method and constitution of (A 2 ); it is for example within the range from 0.01 to 4 %, advantageously 0.05 to 3 %, preferably 0.1 to 2 %, by weight
  • the liquor pH is advantageously in the distinctly acidic to nearly neutral range, for example in the pH range from 4 to 6.5, preferably 5 to 6.
  • the liquors may be applied to the textile material by conventional methods, for example by exhaust processes or impregnation processes, and at appropriate suitable liquor lengths and temperature conditions
  • the liquors may be applied to the substrate by customary methods, e.g. by padding, dipping or spraying, and the impregnated substrate, optionally after intermediate drying, may then be thermofixed at elevated temperature, e.g. in the range from 150 to 220°C, in which case a suitable fixation temperature can be chosen according to the material (for polyester e.g. from 160 to 220°C, for other synthetic fibres and for semisynthetic fibres e.g.
  • hquor-to-goods ratios in the range from 2:1 to 100: 1, usually 3: 1 to 60: 1.
  • hquor-to-goods ratios of 4: 1 to 40: 1, m particular 5: 1 to 20: 1, are prefe ⁇ ed; the temperatures may also vary as desired m the respectively suitable ranges, for example from 95 to 180°C, HT conditions being prefe ⁇ ed, e.g. the range from 105 to 180°C, preferably > 125°C, e.g. in the range from 125 to 135°C.
  • the packages are immersed into the liquor or have the liquor poured over them and then the liquor is pumped through the cheese (from in to out or vice versa or also alternately) for the entire dyeing time.
  • the temperature is slowly raised, for example at a rate of 0.5 to 5°C per minute, preferably 1 to 4°C per minute, until the desired dyeing temperature (HT conditions) is reached, at which dyemg may be ca ⁇ ied out e.g. for 20 to 60 minutes, and then it is brought back down slowly, for example at a rate of 1 to 10°C per minute, preferably 2 to 6°C per minute.
  • the overpressure upstream of the package may be for example in the range from 0.02 to 0.5 bar, preferably 0 5 to 0 2 bar, while - using the dispersions (U) of the invention, especially the prefe ⁇ ed ones - practically no pressure buildup takes place during the entire dyeing or brightening operation.
  • the dispersions (U) of the invention are very stable to the destabilizing action of high shearing forces as may occur in particular application processes, especially for example in cheeses and in jet dyeing machines (dye-jets), and are therefore particularly suitable for such processes. They are also stable to any l ⁇ egular action of high temperatures as may occur on the treated substrate, for example in the course of the drying and/or thermofixmg after an impregnation process, and are therefore also particularly suitable for such application processes (i.e. impregnating and thermofixmg).
  • the table herembelow lists the percentage composition of further aqueous dispersions of the invention which are preparable similarly to Example 1.
  • the numbers reported for each component are percentages in the respective aqueous dispersion.
  • B ⁇ 3A polyvmyl alcohol having residual acetyl content of 10 7 % (viscosity of 4 % aqueous solution at 20°C 4 cP - according to DIN 53015)
  • B Y3 B polyvmyl alcohol having residual acetyl content of 10 7 % (viscosity of 4 % aqueous solution at 20°C 8 cP - according to DIN 53015)
  • This cheese is dyed with the below-mentioned dyes in a liquor circulation machine (for example Colorstar from Zeltex AG, Switzerland)
  • the liquor yarn ratio is 10 1
  • the water hardness is 1 l°dH (German degrees of hardness)
  • the dyes used are
  • a polyester/cotton blend fabnc is padded with an aqueous brightening liquor containing 0 8 to 4 g/1 of the dispersion according to Example 1 and 0 2 g/1 of the adduct of 6 mol of ethylene oxide to 1 mol of t ⁇ decyl alcohol to a wet pick-up of 70 % based on the weight of the dry substrate, then pred ⁇ ed for 2 minutes at 130°C and thermosoled for 30 minutes at 180°C By this the polyester portion of the blend fabric is satisfactorily optically brightened
  • the cotton portion can then, in a second process step, in a manner conventional per se, under alkaline conditions, be simultaneously optically brightened with an optical bnghtener of the bist ⁇ azinylamino- stilbenedisulphomc acid se ⁇ es and bleached with hydrogen peroxide in the presence of a peroxide bleach liquor stabilizer (wet pick-up 70 %, 90 minutes' hot dwell at 95°C, then hot and cold rinse and finally drying)
  • a peroxide bleach liquor stabilizer wet pick-up 70 %, 90 minutes' hot dwell at 95°C, then hot and cold rinse and finally drying
  • Polyester fabric is optically b ⁇ ghtened in a jet at a liquor/substrate ratio of 5 1 to 10 1 with an aqueous liquor containing (based on the substrate) 0 1-1 5 % of the dispersion of Example 2 and 0 5 % of condensation product of naphthalenesulphomc acid and formaldehyde 5/4 (as sodium salt), pH 5 5 (set with acetic acid) using the following temperature profile 30 minutes' heating from 40 to 130°C, treating at 130°C for 30 minutes, thereafter hot nnse, then cooling, unloading and drying This provides very uniform optical b ⁇ ghtenmgs
  • a polyester fabric is padded with an aqueous b ⁇ ghtening liquor containing 2 to 15 g/1 of the dispersion of Example 2 and 0 2 g/1 of the adduct of 6 mol of ethylene oxide to 1 mol of t ⁇ decyl alcohol, up to a wet pick-up of 80 % based on the weight of the dry substrate, then pred ⁇ ed at 130°C for 2 minutes and thermosoled at 170°C for 30 seconds
  • the polyester fabric is satisfactorily optically brightened

Landscapes

  • Textile Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Detergent Compositions (AREA)
  • Coloring (AREA)
  • Treatment Of Fiber Materials (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Colloid Chemistry (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
PCT/IB1999/001466 1998-08-25 1999-08-24 Aqueous compositions of uv-active agents, their production and use Ceased WO2000011256A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE69923984T DE69923984T2 (de) 1998-08-25 1999-08-24 Wässriges präparat eines uv-aktiven mittels und seine herstellung sowie seine verwendung
AT99936928T ATE290117T1 (de) 1998-08-25 1999-08-24 Wässriges präparat eines uv-aktiven mittels und seine herstellung sowie seine verwendung
JP2000566501A JP2002523561A (ja) 1998-08-25 1999-08-24 Ｕｖ活性剤の水性組成物、その製造及び使用
EP99936928A EP1115937B1 (en) 1998-08-25 1999-08-24 Aqueous compositions of uv-active agents, their production and use
BRPI9913241-9A BR9913241B1 (pt) 1998-08-25 1999-08-24 dispersço aquosa contendo absorvedor de luz uv e uso da mesma.
US09/763,506 US6723256B1 (en) 1998-08-25 1999-08-24 Aqueous compositions of a UV-active agents, their production and use
ES99936928T ES2238845T3 (es) 1998-08-25 1999-08-24 Composiciones acuosas de agentes activos frente a la luz uv, su produccion y uso.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP98810840.3 1998-08-25
EP98810840 1998-08-25
EP99810474 1999-06-01
EP99810474.9 1999-06-01

Publications (1)

Publication Number Publication Date
WO2000011256A1 true WO2000011256A1 (en) 2000-03-02

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PCT/IB1999/001466 Ceased WO2000011256A1 (en) 1998-08-25 1999-08-24 Aqueous compositions of uv-active agents, their production and use

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PCT/IB1999/001467 Ceased WO2000011257A1 (en) 1998-08-25 1999-08-24 Aqueous compositions of uv-active agents, their production and use

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EP (2) EP1115938B1 (enExample)
JP (2) JP4638034B2 (enExample)
KR (2) KR100607533B1 (enExample)
AT (2) ATE290117T1 (enExample)
BR (2) BR9913241B1 (enExample)
DE (2) DE69908619T2 (enExample)
DK (1) DK1115938T3 (enExample)
ES (2) ES2238845T3 (enExample)
WO (2) WO2000011257A1 (enExample)

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KR100607533B1 (ko) * 1998-08-25 2006-08-02 클라리언트 파이넌스 (비브이아이)리미티드 자외선-활성제의 수성 조성물, 이의 제조방법 및 용도
US7184886B1 (en) * 2001-12-21 2007-02-27 Garmin Ltd. Navigation system, method and device with detour algorithm
US7527656B2 (en) * 2005-06-30 2009-05-05 Huntsman International Llc Process for the thermal and photochemical stabilization of dyed polyamide fiber material
GB0600644D0 (en) * 2006-01-13 2006-02-22 Unilever Plc Care composition
US20070224135A1 (en) * 2006-03-24 2007-09-27 Xianbin Liu Stable aqueous suspension concentrate for delivery of UV-labile water-insoluble biocides
EP2052021A1 (en) * 2006-08-08 2009-04-29 Clariant International Ltd. Aqueous solutions of optical brighteners
EP2220288B1 (en) * 2007-12-14 2012-02-08 Unilever N.V. Process for treatment of a fabric
DE102013006763B4 (de) * 2013-04-19 2020-12-31 Adient Luxembourg Holding S.À R.L. Verfahren zum Herstellen von bedruckten Textilien für Kraftfahrzeuge
CN108755177A (zh) * 2018-06-04 2018-11-06 安徽恒益纺织科技有限公司 一种用于棉麻纤维织物分散染料的分散助剂
KR102697074B1 (ko) * 2022-06-09 2024-08-22 효성티앤씨 주식회사 형광 탄성사 및 그 제조방법

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EP0468921A1 (de) * 1990-07-23 1992-01-29 Ciba-Geigy Ag Wässrige Dispersion schwerlöslicher UV-Absorber

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EP0225287A1 (de) * 1985-11-25 1987-06-10 Ciba-Geigy Ag Lagerstabile Präparate von in Wasser unlöslichen bis schwerlöslichen Feststoffen
EP0321393A1 (de) * 1987-11-27 1989-06-21 Ciba-Geigy Ag Aufhellerdispersion
EP0468921A1 (de) * 1990-07-23 1992-01-29 Ciba-Geigy Ag Wässrige Dispersion schwerlöslicher UV-Absorber

Also Published As

Publication number Publication date
US6780827B1 (en) 2004-08-24
DE69923984D1 (de) 2005-04-07
WO2000011257A1 (en) 2000-03-02
DE69923984T2 (de) 2005-07-28
DK1115938T3 (da) 2003-09-08
ATE242351T1 (de) 2003-06-15
JP2002523562A (ja) 2002-07-30
KR100607534B1 (ko) 2006-08-02
DE69908619T2 (de) 2004-05-13
BR9913241A (pt) 2001-05-15
KR100607533B1 (ko) 2006-08-02
JP4638034B2 (ja) 2011-02-23
ATE290117T1 (de) 2005-03-15
BR9913241B1 (pt) 2008-11-18
ES2207962T3 (es) 2004-06-01
EP1115938B1 (en) 2003-06-04
JP2002523561A (ja) 2002-07-30
ES2238845T3 (es) 2005-09-01
EP1115937A1 (en) 2001-07-18
BR9913179B1 (pt) 2008-11-18
US6723256B1 (en) 2004-04-20
KR20010072941A (ko) 2001-07-31
EP1115937B1 (en) 2005-03-02
BR9913179A (pt) 2001-05-15
DE69908619D1 (de) 2003-07-10
EP1115938A1 (en) 2001-07-18
KR20010072947A (ko) 2001-07-31

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