WO2007017430A1 - Infrared ray-absorbing fibers - Google Patents

Infrared ray-absorbing fibers Download PDF

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Publication number
WO2007017430A1
WO2007017430A1 PCT/EP2006/064946 EP2006064946W WO2007017430A1 WO 2007017430 A1 WO2007017430 A1 WO 2007017430A1 EP 2006064946 W EP2006064946 W EP 2006064946W WO 2007017430 A1 WO2007017430 A1 WO 2007017430A1
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Prior art keywords
fibres
formula
cellulose
phthalocyanine dye
dyed
Prior art date
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PCT/EP2006/064946
Other languages
French (fr)
Inventor
Véronique Hall-Goulle
Original Assignee
Huntsman Advanced Materials (Switzerland) Gmbh
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
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Publication of WO2007017430A1 publication Critical patent/WO2007017430A1/en

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    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • D06P1/26—Phthalocyanine dyes
    • 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
    • D06P1/004—Dyeing with phototropic dyes; Obtaining camouflage effects
    • 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
    • D06P1/38—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 reactive dyes

Definitions

  • the invention relates to the use of fibres dyed or printed with a specific phthalocyanine dye for the production of camouflage equipment.
  • camouflage The purpose of camouflage is to adapt clothing and military objects to their natural surroundings. Textile materials for military purpose usually are made of synthetic fibres, like polyester or polyamide, or mixed cellulose/synthetic fibres and are generally dyed in yellowish-beige, medium brown, grey, green or olive-coloured hues. With regard to an effective camouflage, it is necessary to defeat infrared imaging systems by making it difficult for the device to discriminate between the potential target object and its background. In order to avoid contrasts and to break outlines, clothes should exhibit 10-50 % reflectance in 700-1200 nm range, depending on shade.
  • the present invention relates to the use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1) or (2)
  • R 1 and R 2 independently of the other denote hydrogen, Ci-C 2O alkyl or Ci-C 2O alkyl interrupted by one or more oxygen or sulphur atoms, X represents oxygen or sulphur, and R 3 is Ci-C 2O alkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl, for the production of camouflage equipment.
  • Preferred compounds of formula (1) are those wherein R 1 is hydrogen and R 2 denotes CrC 12 alkyl Or -(CH 2 CH 2 O) n -CH 3 , wherein n is a number from 1 to 5.
  • Particularly preferred dyes are the compounds of formula (1), wherein R 1 is hydrogen and R 2 denotes d-C 8 alkyl.
  • Preferred compounds of formula (2) are those wherein R 3 denotes C r C 12 alkyl.
  • phthalocyanine dyes of formula (1a) and (2a) are especially preferred.
  • R 1 , R 2 and R 3 are as defined above.
  • the most preferred phthalocyanine dyes are the compounds of formula (101) and (102)
  • the phthalocyanine dyes of formula (1) and (2) can advantageously be combined with other dyes or pigments.
  • the term "camouflage equipment” includes all articles intended for camouflage purposes, preferably for military purposes, which can be prepared from polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing any of these fibres. Such articles may be, for example, clothes, luggage, coverings for hiding vehicles or buildings, parachutes, artificial floors, panelings inside vehicles or buildings etc.
  • phthalocyanine dyes of formula (1) or (2) or dye mixtures containing phthalocyanine dyes of formula (1) or (2) to the fibre materials can be effected in accordance with known colouring methods, for example with the thermosol process for dyeing or conventional printing processes.
  • the said fibre materials can be in a variety of processing forms, e.g. in the form of woven or knitted fabrics.
  • the dye is ground so that its particle size is on average from 0.1 to 10 microns. Grinding can be carried out in the presence of dispersants.
  • the dried dye is ground together with a dispersant or kneaded into a paste form together with a dispersant. It can be used in liquid form as dispersion or it can be dried in vacuo by atomisation. After adding water, the resulting preparations can be used to prepare printing pastes and dyebaths.
  • the customary thickeners will be used, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • modified or unmodified natural products for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • Polyester or polyamide fibre materials can be dyed in the thermosol process from an aqueous dispersion in the presence of customary additives, preferably at temperatures of from 80 to 180 0 C.
  • a further object of the invention is the use of polyamide fibres or polyester fibres dyed with a phthalocyanine dye of formula (1) or (2) according to claim 1 in the thermosol process for the production of camouflage equipment.
  • Phthalocyanine dyes of formula (1) or (2) are suitable for the mass-colouration of plastics, too.
  • the colouring of polyesters and polyamides with the phthalocyanine dyes of formula (1) or (2) can be carried out, for example, by mixing such a dye into those substrates using roll mills, mixing apparatus or grinding apparatus, with the result that the dye is dissolved or finely dispersed in the high molecular weight material.
  • the high molecular weight organic material with the admixed dye is then processed using processes known per se, for example calendering, compression moulding, extrusion, coating, spinning, casting or injection moulding, whereby the coloured material acquires its final form.
  • the admixing of the dye is carried out immediately prior to the actual processing step, by continuously feeding a solid dye (for example in powder form) and, at the same time, a granulated or pulverulent high molecular weight organic material, and optionally also additional ingredients, e.g. additives, directly into the intake zone of an extruder, where mixing takes place just before processing.
  • a solid dye for example in powder form
  • additional ingredients e.g. additives
  • the invention further relates to the use of polyamide fibres or polyester fibres mass-coloured with a phthalocyanine dye of formula (1 ) or (2) according to claim 1 for the production of camouflage equipment.
  • a further object of the invention is the use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres printed with a phthalocyanine dye of formula (1) or (2) as defined above.
  • Cellulose or mixed cellulose/synthetic fibres can advantageously be dyed with phthalocyanine dyes of formula (1) or (2) or dye mixtures containing phthalocyanine dyes of formula (1) or (2) according to the process described in WO 2005/024123, hereby incorporated by reference.
  • the invention therefore further relates to the use of cellulose or mixed cellulose/synthetic fibres which were treated in any sequence with water, a water-soluble organic solvent having a boiling point >150 0 C and a phthalocyanine dye of formula (1) or (2) as defined in claim 1 for the production of camouflage equipment.
  • a further object of the invention is the camouflage equipment prepared by dyeing or printing polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1) or (2) to claim 1.
  • Geropon T77 wetting agent
  • Surfinol DF58 antifoam agent
  • Zirconium beads (diameter 0.6 to 1 mm) are then added to the above-obtained dispersion in a glass bottle tightly closed. The bottle is then placed in a Scandex apparatus and thereby agitated for 4 hours. The thus obtained fine dispersion is then filtered on a conventional B ⁇ chner funnel to provide the final dye dispersion.
  • the amount of added deionised water can vary as a function of the viscosity of the dye dispersion and/or of the printing paste.
  • the printing paste is applied in a classical way on the textile (PES/CO 67/33) through a screen. After drying at 90 0 C, the textile is thermofixed at 220 0 C for 1 minute.
  • the thus obtained printed fabric exhibits a very good light fastness, wash fastness, fastness to bleaching with hypochlorite (ISO 105-N01) and wet rubbing fastness.
  • the resulting printed textile has the following IR reflection spectrum:
  • Example 1 is repeated by using the same amount of dye of formula (102) instead of dye of formula (101).
  • the thus obtained printed fabric exhibits a very good light fastness, wash fastness, fastness to bleaching with hypochlorite (ISO 105-N01) and wet rubbing fastness.
  • the resulting printed textile has the following IR reflection spectrum:

Abstract

The invention relates to the use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a specific phthalocyanine dye for the production of camouflage equipment.

Description

Infrared Ray-absorbing Fibers
The invention relates to the use of fibres dyed or printed with a specific phthalocyanine dye for the production of camouflage equipment.
The purpose of camouflage is to adapt clothing and military objects to their natural surroundings. Textile materials for military purpose usually are made of synthetic fibres, like polyester or polyamide, or mixed cellulose/synthetic fibres and are generally dyed in yellowish-beige, medium brown, grey, green or olive-coloured hues. With regard to an effective camouflage, it is necessary to defeat infrared imaging systems by making it difficult for the device to discriminate between the potential target object and its background. In order to avoid contrasts and to break outlines, clothes should exhibit 10-50 % reflectance in 700-1200 nm range, depending on shade. Accordingly, there is a need for dyestuffs suitable for dyeing synthetic or mixed cellulose/synthetic fibres which, alone or in combination with other dyes, allow combined visual and infrared camouflage. At the same time, a high fastness level is stipulated, especially with regard to lightfastness and washfastness.
It has now surprisingly been found that certain specific phthalocyanine dyes meet the criteria given above to a considerable degree.
The present invention relates to the use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1) or (2)
(1).
Figure imgf000002_0001
wherein R1 and R2 independently of the other denote hydrogen, Ci-C2Oalkyl or Ci-C2Oalkyl interrupted by one or more oxygen or sulphur atoms, X represents oxygen or sulphur, and R3 is Ci-C2Oalkyl, C5-C30aryl or C6-C36aralkyl, for the production of camouflage equipment.
The compounds of formulae (1) and (2) are known and either commercially available or can be prepared according to known processes.
Preferred compounds of formula (1) are those wherein R1 is hydrogen and R2 denotes CrC12alkyl Or -(CH2CH2O)n-CH3, wherein n is a number from 1 to 5.
Particularly preferred dyes are the compounds of formula (1), wherein R1 is hydrogen and R2 denotes d-C8alkyl.
Preferred compounds of formula (2) are those wherein R3 denotes CrC12alkyl.
Especially preferred are the phthalocyanine dyes of formula (1a) and (2a),
Figure imgf000004_0001
Figure imgf000004_0002
wherein R1, R2 and R3 are as defined above.
The most preferred phthalocyanine dyes are the compounds of formula (101) and (102)
Figure imgf000004_0003
In order to attain specific hues or colour nuances, the phthalocyanine dyes of formula (1) and (2) can advantageously be combined with other dyes or pigments. The term "camouflage equipment" includes all articles intended for camouflage purposes, preferably for military purposes, which can be prepared from polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing any of these fibres. Such articles may be, for example, clothes, luggage, coverings for hiding vehicles or buildings, parachutes, artificial floors, panelings inside vehicles or buildings etc.
The application of the phthalocyanine dyes of formula (1) or (2) or dye mixtures containing phthalocyanine dyes of formula (1) or (2) to the fibre materials can be effected in accordance with known colouring methods, for example with the thermosol process for dyeing or conventional printing processes.
In such processes, the said fibre materials can be in a variety of processing forms, e.g. in the form of woven or knitted fabrics.
It is advantageous to convert the dyes of formula (1 ) or (2) or dye mixtures containing one of these dyes into a dye preparation prior to use. For this purpose, the dye is ground so that its particle size is on average from 0.1 to 10 microns. Grinding can be carried out in the presence of dispersants. For example, the dried dye is ground together with a dispersant or kneaded into a paste form together with a dispersant. It can be used in liquid form as dispersion or it can be dried in vacuo by atomisation. After adding water, the resulting preparations can be used to prepare printing pastes and dyebaths.
For printing, the customary thickeners will be used, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
Polyester or polyamide fibre materials can be dyed in the thermosol process from an aqueous dispersion in the presence of customary additives, preferably at temperatures of from 80 to 1800C.
Accordingly, a further object of the invention is the use of polyamide fibres or polyester fibres dyed with a phthalocyanine dye of formula (1) or (2) according to claim 1 in the thermosol process for the production of camouflage equipment.
Phthalocyanine dyes of formula (1) or (2) are suitable for the mass-colouration of plastics, too. Hence, the colouring of polyesters and polyamides with the phthalocyanine dyes of formula (1) or (2) can be carried out, for example, by mixing such a dye into those substrates using roll mills, mixing apparatus or grinding apparatus, with the result that the dye is dissolved or finely dispersed in the high molecular weight material. The high molecular weight organic material with the admixed dye is then processed using processes known per se, for example calendering, compression moulding, extrusion, coating, spinning, casting or injection moulding, whereby the coloured material acquires its final form. It is also possible for the admixing of the dye to be carried out immediately prior to the actual processing step, by continuously feeding a solid dye (for example in powder form) and, at the same time, a granulated or pulverulent high molecular weight organic material, and optionally also additional ingredients, e.g. additives, directly into the intake zone of an extruder, where mixing takes place just before processing. In general, however, it is preferable for the dye to be mixed into the high molecular weight organic material beforehand, because more even colouration of the substrates can be obtained.
It is also possible, in order to achieve different shades of colour, to add to the high molecular weight organic materials, in addition to the phthalocyanine dye of formula (1) or (2), also further pigments or other colorants in any desired amounts, optionally together with further additives, e.g. fillers or siccatives.
The invention further relates to the use of polyamide fibres or polyester fibres mass-coloured with a phthalocyanine dye of formula (1 ) or (2) according to claim 1 for the production of camouflage equipment.
A further object of the invention is the use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres printed with a phthalocyanine dye of formula (1) or (2) as defined above.
Several attempts have been made to develop efficient processes for printing or dyeing mixed cellulose/synthetic fibres, for example polyester-cotton blends. Two fundamentally different approaches were taken:
Processes using one class of dye only and processes using mixtures of two classes of dyes. Usually reactive dyes or vat dyes are combined with disperse dyes. However, the use of such dye mixtures is associated with several drawbacks and it is hardly possible to obtain the same colour and depth on the two fibres by this method.
Processes for dyeing cellulose fibres or blends of cellulose fibres and synthetic fibres with a single disperse dye have also been described. However, the top requirements with respect to light fastness and wash fastness in most cases have not been met.
Cellulose or mixed cellulose/synthetic fibres can advantageously be dyed with phthalocyanine dyes of formula (1) or (2) or dye mixtures containing phthalocyanine dyes of formula (1) or (2) according to the process described in WO 2005/024123, hereby incorporated by reference.
The invention therefore further relates to the use of cellulose or mixed cellulose/synthetic fibres which were treated in any sequence with water, a water-soluble organic solvent having a boiling point >150 0C and a phthalocyanine dye of formula (1) or (2) as defined in claim 1 for the production of camouflage equipment.
A further object of the invention is the camouflage equipment prepared by dyeing or printing polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1) or (2) to claim 1.
The following non-limitative Examples illustrate the invention in more detail.
Application Examples:
Example 1
1. Preparation of the Dispersion The dye of formula (101 ) is dispersed according to the following formulation:
• 29,2% dye
• 7.3% 1 ,2-propylenglykol (solvent)
• 3.7% Lutensol AT25 (dispersant)
• 0.8% Geropon T77 (wetting agent) • 0.1% Surfinol DF58 (antifoam agent)
• 0.4% Proxel GXL (antimicrobial)
• 58.5% deionised water
Zirconium beads (diameter 0.6 to 1 mm) are then added to the above-obtained dispersion in a glass bottle tightly closed. The bottle is then placed in a Scandex apparatus and thereby agitated for 4 hours. The thus obtained fine dispersion is then filtered on a conventional Bϋchner funnel to provide the final dye dispersion.
2. Preparation of the Printing paste A typical run consists in the preparation of a mother paste, to which a quantity of the dye dispersion and water will be subsequently added.
- Mother paste:
• 84.2% deionised water • 0.8% NH4OH (28%)
• 0.4% Alcoprint PA-NS
• 9.9% PEG400
• 2.3% Alcoprint PSC
• 2.4% Alcoprint PTP
- Printing paste
• 33.3% deionised water
• 60.1 % mother paste
• 6.6% dye dispersion The amount of added deionised water can vary as a function of the viscosity of the dye dispersion and/or of the printing paste.
3. Printing
The printing paste is applied in a classical way on the textile (PES/CO 67/33) through a screen. After drying at 900C, the textile is thermofixed at 2200C for 1 minute.
After a brief cold rinse, a 30 minutes wash at 800C is performed in a bath containing:
• 2g/L carbonate
• 1g/L Calgon
• 1g/L UItravon JU
4. Tests
The thus obtained printed fabric exhibits a very good light fastness, wash fastness, fastness to bleaching with hypochlorite (ISO 105-N01) and wet rubbing fastness.
The resulting printed textile has the following IR reflection spectrum:
Figure imgf000009_0001
Example 2:
Example 1 is repeated by using the same amount of dye of formula (102) instead of dye of formula (101).
The thus obtained printed fabric exhibits a very good light fastness, wash fastness, fastness to bleaching with hypochlorite (ISO 105-N01) and wet rubbing fastness.
The resulting printed textile has the following IR reflection spectrum:
Figure imgf000010_0001

Claims

Claims
1. Use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1 ) or (2)
Figure imgf000011_0001
Figure imgf000011_0002
wherein R1 and R2 independently of the other denote hydrogen, Ci-C2Oalkyl or Ci-C2Oalkyl interrupted by one or more oxygen or sulphur atoms,
X represents oxygen or sulphur, and
R3 is Ci-C2Oalkyl, C5-C30aryl or C6-C36aralkyl, for the production of camouflage equipment.
2. Use of fibres according to claim 1 dyed or printed with a phthalocyanine dye of formula (1), wherein R1 is hydrogen and R2 denotes CrC12alkyl Or -(CH2CH2O)n-CH3, wherein n is a number from 1 to 5.
3. Use of fibres according to claim 1 dyed or printed with a phthalocyanine dye of formula (1), wherein R1 is hydrogen and R2 denotes d-C8alkyl.
4. Use of fibres according to claim 1 dyed or printed with a phthalocyanine dye of formula (2), wherein R3 denotes CrCi2alkyl.
5. Use of fibres according to claim 1 dyed or printed with a phthalocyanine dye of formula (1a) or (2a),
Figure imgf000012_0001
Figure imgf000012_0002
wherein R1, R2 and R3 are as defined in claim 1.
6. Use of fibres according to claim 1 dyed or printed with a phthalocyanine dye of formula (101) or (102),
Figure imgf000013_0001
7. Use of polyamide fibres or polyester fibres dyed with a phthalocyanine dye of formula (1) or (2) according to claim 1 in the thermosol process for the production of camouflage equipment.
8. Use of polyamide fibres or polyester fibres mass-coloured with a phthalocyanine dye of formula (1) or (2) according to claim 1 for the production of camouflage equipment.
9. Use of polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres printed with a phthalocyanine dye of formula (1) or (2) according to claim 1 for the production of camouflage equipment.
10. Use of cellulose or mixed cellulose/synthetic fibres which were treated in any sequence with water, a water-soluble organic solvent having a boiling point >150 0C and a phthalocyanine dye of formula (1) or (2) as defined in claim 1 for the production of camouflage equipment.
11. Camouflage equipment prepared by dyeing or printing polyamide fibres, polyester fibres, cellulose fibres or mixed fibres containing polyamide fibres, polyester fibres or cellulose fibres dyed or printed with a phthalocyanine dye of formula (1) or (2) as defined above.
PCT/EP2006/064946 2005-08-11 2006-08-02 Infrared ray-absorbing fibers WO2007017430A1 (en)

Applications Claiming Priority (2)

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EP05107380 2005-08-11
EP05107380.7 2005-08-11

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE6609396U (en) * 1966-05-13 1972-05-10 Eltro Gmbh FABRIC WEB FOR THE MANUFACTURE OF INFRARED CAMOUFLAGE NETS AND tarpaulins.
US4095940A (en) * 1972-01-05 1978-06-20 Hoechst Aktiengesellschaft Process for the production of camouflage dyeings and prints
DE10204829C1 (en) * 2002-02-06 2003-07-17 Gerd Hugo Flat structural metal panel, useful as roof or wall element of airport, military or agricultural building, e.g. cattle shed or store, has anticorrosion reflective and reflective outer and anticorrosion and low emission inner coatings
WO2005024123A2 (en) * 2003-09-08 2005-03-17 Ciba Specialty Chemicals Holding Inc. Process for printing or dyeing cellulose/polyester mixed fibres

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE6609396U (en) * 1966-05-13 1972-05-10 Eltro Gmbh FABRIC WEB FOR THE MANUFACTURE OF INFRARED CAMOUFLAGE NETS AND tarpaulins.
US4095940A (en) * 1972-01-05 1978-06-20 Hoechst Aktiengesellschaft Process for the production of camouflage dyeings and prints
DE10204829C1 (en) * 2002-02-06 2003-07-17 Gerd Hugo Flat structural metal panel, useful as roof or wall element of airport, military or agricultural building, e.g. cattle shed or store, has anticorrosion reflective and reflective outer and anticorrosion and low emission inner coatings
WO2005024123A2 (en) * 2003-09-08 2005-03-17 Ciba Specialty Chemicals Holding Inc. Process for printing or dyeing cellulose/polyester mixed fibres

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