GB2187746A - Hydroxyphenyl benzotriazole UV light absorber aqueous dispersions and their use in dyeing processes - Google Patents

Hydroxyphenyl benzotriazole UV light absorber aqueous dispersions and their use in dyeing processes Download PDF

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Publication number
GB2187746A
GB2187746A GB08705901A GB8705901A GB2187746A GB 2187746 A GB2187746 A GB 2187746A GB 08705901 A GB08705901 A GB 08705901A GB 8705901 A GB8705901 A GB 8705901A GB 2187746 A GB2187746 A GB 2187746A
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Prior art keywords
substrate
composition according
composition
percentages
water
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GB08705901A
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GB8705901D0 (en
GB2187746B (en
Inventor
Hermann Gilgen
Wolfgang Groebke
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Sandoz AG
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Sandoz AG
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Publication of GB2187746A publication Critical patent/GB2187746A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2461/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Materials Engineering (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paints Or Removers (AREA)

Abstract

Stable dispersions comprise 20 to 45% of an insoluble or sparingly soluble U.V. absorber of the 2-(2'-hydroxyphenyl)benztriazole series having an average particle size of less than 5 mu m; 7 to 15% of a dispersing agent that is a substantially salt-free condensation product of sulphonated tolylether and formaldehyde; and 40 to 73% water; the percentages being by weight of the total composition. These compositions are suitable for applying U.V. absorbers of the benztriazole series to a substrate in the form of a dispersion in water. They may be added to dye baths containing disperse dyes to give products with good light fastness.

Description

SPECIFICATION Improvements in or relating to organic compounds The invention relates to compositions of water-insoluble or very sparingly soluble U.V. absorbers that are stable to storage.
The problem with water-insoluble or very sparingly soluble U.V absorbers, particularly of the 2-(2'-hydroxyphenyl)benztriazole series, is that they tend to be difficult to disperse in water. To date, it has not been possible to produce concentrates of such U.V. absorbers that are stable for any length of time. For example, it is possible to form an aqueous dispersion of such U.V.
absorbers after 90 hours or more of milling. However, after a short time the dispersion breaks up forming a clear aqueous phase with practically no U.V. absorber and a gelatinous precipitate, which after a few days is so compact that it cannot be stirred or shaken to reform the dispersion.
To alleviate this problem there is provided. according to the invention a composition comprising: 20 to 45% of an insoluble or sparingly soluble U.V. absorber of the 2-(2'-hydroxyphenyl)benztri azole series having an average particle size of less than 5 item; 7 to 15% of a dispersing agent that is a substantially salt-free condensation product of sulphonated tolylether and formaldehyde; and 40 to 73% water; the percentages being by weight of the total composition.
Compositions according to the invention may include one or more of the following: (a) 0.5 to 1.5% of a solubilising agent (b) 0.1 to 0.2% of a buffer (c) 0.8 to 2% of a nonionic surfactant; and (d) 0.1 to 0.3% of an antifouling agent.
Preferred dispersing agents are those commercially available, (for example Baykanol SL) as described in US Patent 4,386,037, especially Example 15. The contents and preferences of this Patent are incorporated herewith by reference. The preferred amount of formaldehyde used per mol of sulphonated tolylether is from 0.2 to 3 moles.
Preferred U.V. absorbers of the 2-(2'-hydroxyphenyl)benztriazole series are those described in Japanese Kokai 56-31084 and Swiss Patent 494,060.-The Kokai and the Swiss Patent are incorporated herein by reference.
Preferably the average particle size of the U.V absorbers used in a composition according to the invention is less than 1 Xtm.
Preferred non-ionic surfactants are addition products of Ca l2 alkylphenol (preferably nonylphenol) and ethylene oxide and/or propylene oxide. Preferably the ratio of phenol to alkylene oxide is 1:1 to 1:10.
Preferred solubilising agents are addition products of poly-Cl 4alkylene glycols (preferably polypropylene or polyethylene glycol) with propylene oxide and/or ethylene oxide. More preferably the solubilising agents are the addition products of polypropylene- glycol and propylene oxide and ethylene oxide, most preferably having a molecular weight of the polyoxypropylene part of 1500 to 2500 and 40 to 60% polyoxyethylene units, particularly preferred being "Pluronic" type products.
Preferred antifouling agents are fungicides for example Giv Gard, a commercially available product.
Preferably the buffer is a phosphoric acid (e.g. orthophosphoric acid).
Preferred compositions according to the invention comprise 25 to 40% of 2-2-(2'-hydroxy-3'-tert.butyl-5'-methyl-phenyl)-5-chlorobenztriazole; 8 to 12% of salt-free condensation product of ditolylethersulphonate and formaldehyde; 0.8 to 1.2% of the addition product of polypropylene glycol, propyleneoxide and ethyleneox ide having a molecular weight of the polyoxypropylene part of 1700 to 2300; and 40 to 60% polyoxyethylene units in the polymer; 0.12 to 0.18% of a phosphoric acid; and 1.0 to 1.5% of the addition product of a C1 ,2alkylphenol and a C2 3alkyleneoxide; and 45 to 65% demineralised -water; the percentages being by weight of the total composition, Preferably the pH of a composition according to the invention is between 4.5 and 5.8,-more preferably 5.0 to 5.5.
Compositions according to the invention are useful for use in dyeing; padding or printing processes preferably in a concentration of 0.5 to 2.0% based on the weight of substrate to be treated.
Compositions according to the invention have excellent stability to storage.
Compositions according to the invention are -also suitable as aftertreatment compositions beingapplied by padding, printing or exhaustion techniques as a 0.5 to 2.0% dispersion in water.
Further, according to the invention there is provided a process for dyeing a substrate comprising applying to the substrate 0.1 to 5% of a dye (preferably a disperse dye) 0.1 to 5% of a composition according to the invention [the percentages being by weight of the- substrate being dyed] preferably in an aqueous medium in a liquor to goods ratio of 10:1 to 60:1.
Substrates dyed with disperse dyes and a U.V. absorber according to the invention show excellent light fastness properties.
The average particle size can be measured by placing a sample on a microscope on which ascale has been superimposed.
The invention will now be illustrated by the following Examples in which all parts and percentages are by weight and all temperatures are in C.
Example 1 The following are mixed together in a vessel 40 parts of 21(2'-hydroxy-3'-tert.butyl-5'-methyl phenyl)-5-chlorobenztriazole 10 parts of a commercially available condensation product (salt-free) of ditolylether sulphonate and formaldehyde (Baykanol SL); 0.25 parts of a fungicide (Giv Gard) 1 part of a commercially available product of 9 moles ethyleneoxide and 1 mol nonylphenol; and 1 part of commercially available Pluronic P 75 (from BASF/Wyandotte Corp.) [the addition product -of propylene-glycol and propylene oxide followed by the further reaction with ethylene oxide; the product having a molecular weight for- the polyoxypropylene part of 2050 (approx.) and having about 50% polyoxyethylene units in the polymer] in -40 parts of demineralised water.
To this mixture is then added about 0.15 parts of ortho phosphoric acid to bring the pH to 5 to 5.5. The mixture is then milled in a bead mill with silicoquarzite-beads until the average size of the particles of the- U.V. absorber is less than 1 um, which occurs after about 30 minutes.
The resulting dispersion is filtered from the silicoquarzite beads, the beads are washed with 7.6 parts of water and the filtrate and water- with which the beads have been washed are added together.
The- resulting concentrate is stable as a dispersion for a number -of months even at temperatures above 50"C.
Examples 2 and 3 Example 1 is repeated using 40 parts of 2-(2'-hydroxy-5'-methylphenyl)benztriazole (Example 2) and 40 parts of 2-(2'-hydroxy-3',5'-di-tert.butyl)benztriazole instead of 40 parts of 2-(2'-hydroxy-3'-tert. butyl-5'-methylphenyl)-5-chlorobenztriazole.
Application Example A dyebath is made up of the following: 1.5 parts of C.l. Disperse Red 74 1.5 parts of the dispersion of Example 1; and 197 parts of dernineralised water.
The pH is brought to 5 by the addition of ammonium sulphate/formic acid in a ratio of 10:1.
This bath is warmed to 60" in a dyeing autoclave and 100 parts of a polyester fabric (of sufficient quality for use in automobile upholstery) is then added, the autoclave is closed and the circulåting bath is heated to 135". Dyeing is carried out at 135" for 20 minutes after which the bath is cooled to 80" and the dyed substrate is removed from the bath. It is then washed, reductively cleared, washed again and dried. The light fastness of the dyed fabric is substantially better than that dyed without the benztriazole present.
Instead of usig 1.5 parts of the dispersion of Example 1, Application Example can be repeated using 1.5 parts of the dispersion of Example 2 or 3.

Claims (8)

1. A composition comprising 20 to 45% of an insoluble or sparingly soluble U.V. absorber of the 2-(2'-hydroxyphenyl)benztri azole series having an average particle size of less than 5 ,um; 7 to 15% of a dispersing agent that is a substantially salt-free condensation product of sulphonated tolylether and formaldehyde; and 40 to 73% water; the percentages being by weight of the total composition.
2. A composition according to Claim 1 comprising additionally one or more of the following: (a) 0.5 to 1.5% of a solubilising agent (b) 0.1 to 0.2% of a buffer (c) 0.8 to 2% of a nonionic surfactant; and (d) 0.1 to 0.3% of an antifouling agent.
3. A composition according to Claim 1 or Claim 2 in which the particle size of the U.V.
absorber is less than 1 ,um.
4. A composition according to Claim 1 comprising 25 to 40% 25 to 40% of 2-(2'-hydroxy-3'-tert.butyl-5'-methyl-phenyl)-5-chlorobenztriazole; 8 to 12% of a salt-free condensation product of ditolylethersulphonate and formaldehyde; 0.8 to 1.2% of the addition product of polypropylene glycol, propyleneoxide and ethyleneox ide having a molecular weight of the polyoxypropylene part of 1700 to 2300; and 40 to 60% polyoxyethylene units in the polymer; 0.12 to 0.18% of a phosphoric acid; and
1.0 to 1.5% of the addition product of a C, l2alkylphenol and a C23alkyleneoxide; and 45 to 65% demineralised water; the percentages being by weight of the total composition.
5. A composition substantially as herein described with reference to any one of Examples 1 to 3.
6. A process for dyeing a substrate comprising applying to that substrate 0.1 to 5% of a dye and 0.1 to 5% of a composition according to Cla;;n 1, the percentages being based on the substrate to be dyed.
7. A substrate to which a composition according to any one of Claims 1 to 5 has been applied.
8. A process substantially as herein described with reference to the Application Example.
GB8705901A 1986-03-15 1987-03-12 Aqueous dispersions of benztriazolyl light stabilisers Expired GB2187746B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE3608687 1986-03-15

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GB8705901D0 GB8705901D0 (en) 1987-04-15
GB2187746A true GB2187746A (en) 1987-09-16
GB2187746B GB2187746B (en) 1989-11-15

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GB8705901A Expired GB2187746B (en) 1986-03-15 1987-03-12 Aqueous dispersions of benztriazolyl light stabilisers

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JP (1) JPS62223383A (en)
KR (1) KR870008992A (en)
BR (1) BR8701161A (en)
CH (1) CH672137A5 (en)
ES (1) ES2007602A6 (en)
FR (1) FR2595730B1 (en)
GB (1) GB2187746B (en)
HK (1) HK79592A (en)
IT (1) IT1216797B (en)
ZA (1) ZA871858B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354174A1 (en) * 1988-07-01 1990-02-07 Ciba-Geigy Ag Stable aqueous composition for modifying light fastness
US5009669A (en) * 1988-05-31 1991-04-23 Ciba-Geigy Corporation Aqueous dispensions of 2-(2'-hydroxyphenyl)benzotriazoles
US5360559A (en) * 1990-03-02 1994-11-01 Ciba-Geigy Corporation Modified ligninsulfonates as dispersing agents for benzoltriazole ultra-violet absorbing agents
WO1997003242A1 (en) * 1995-07-12 1997-01-30 Clariant Finance (Bvi) Limited U.v. absorber compositions
GB2308847A (en) * 1995-12-21 1997-07-09 Clariant Finance Bvi Ltd Compositions comprising UV absorbers
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions
US6391065B1 (en) 1995-11-03 2002-05-21 Boehme Filatex, Inc. UV light absorber composition and method of improving the lightfastness of dyed textiles
EP1466956A1 (en) * 2003-04-07 2004-10-13 Clariant International Ltd. Highly concentrated, storage stable aqueous dispersions for stabilizing lacquers and glazes
WO2005059239A2 (en) * 2003-12-11 2005-06-30 Ciba Specialty Chemicals Holding Inc. Mixture of dispersing agents

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4241088A1 (en) * 1991-12-14 1993-06-17 Sandoz Ag
JP5084143B2 (en) * 2005-02-14 2012-11-28 株式会社Ａｄｅｋａ Light stabilizer emulsion composition
JP5202883B2 (en) * 2007-06-26 2013-06-05 日本乳化剤株式会社 Emulsion for preventing yellowing

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2453146A1 (en) * 1974-11-08 1976-05-13 Sandoz Ag Improving light fastness of colour on polypropylene - using known u.v. -absorbing cpds
JPS5631084A (en) * 1979-08-21 1981-03-28 Toyo Boseki Dispersing composition
JPS5682830A (en) * 1979-12-10 1981-07-06 Toyobo Co Ltd Dispersion composition
CH660828GA3 (en) * 1980-03-28 1987-05-29
JPS599287A (en) * 1982-07-08 1984-01-18 住友化学工業株式会社 Dyeing of hydrophobic fiber
JPS59216979A (en) * 1983-05-18 1984-12-07 三洋化成工業株式会社 Treating agent for fiber
CH677167B5 (en) * 1985-05-08 1991-10-31 Sandoz Ag

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5009669A (en) * 1988-05-31 1991-04-23 Ciba-Geigy Corporation Aqueous dispensions of 2-(2'-hydroxyphenyl)benzotriazoles
EP0354174A1 (en) * 1988-07-01 1990-02-07 Ciba-Geigy Ag Stable aqueous composition for modifying light fastness
US5360559A (en) * 1990-03-02 1994-11-01 Ciba-Geigy Corporation Modified ligninsulfonates as dispersing agents for benzoltriazole ultra-violet absorbing agents
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions
WO1997003242A1 (en) * 1995-07-12 1997-01-30 Clariant Finance (Bvi) Limited U.v. absorber compositions
US6391065B1 (en) 1995-11-03 2002-05-21 Boehme Filatex, Inc. UV light absorber composition and method of improving the lightfastness of dyed textiles
GB2308847A (en) * 1995-12-21 1997-07-09 Clariant Finance Bvi Ltd Compositions comprising UV absorbers
EP1466956A1 (en) * 2003-04-07 2004-10-13 Clariant International Ltd. Highly concentrated, storage stable aqueous dispersions for stabilizing lacquers and glazes
WO2004090069A1 (en) * 2003-04-07 2004-10-21 Clariant International Ltd Highly concentrated, storage stable aqueous dispersions for stabilising coatings and glazes
CN100406537C (en) * 2003-04-07 2008-07-30 克莱里安特财务(Bvi)有限公司 Highly concentrated, storage stable aqueous dispersions for stabilizing lacquers and glazes
WO2005059239A2 (en) * 2003-12-11 2005-06-30 Ciba Specialty Chemicals Holding Inc. Mixture of dispersing agents
WO2005059239A3 (en) * 2003-12-11 2005-10-13 Ciba Sc Holding Ag Mixture of dispersing agents
US8491671B2 (en) 2003-12-11 2013-07-23 Huntsman International Llc Mixture of dispersing agents

Also Published As

Publication number Publication date
KR870008992A (en) 1987-10-22
JPS62223383A (en) 1987-10-01
CH672137A5 (en) 1989-10-31
ZA871858B (en) 1988-10-26
BR8701161A (en) 1988-01-12
FR2595730B1 (en) 1989-12-01
ES2007602A6 (en) 1989-07-01
IT1216797B (en) 1990-03-14
HK79592A (en) 1992-10-23
IT8747701A0 (en) 1987-03-10
GB8705901D0 (en) 1987-04-15
FR2595730A1 (en) 1987-09-18
GB2187746B (en) 1989-11-15

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Effective date: 19960312