GB2305941A - Discharge printing paste based on thiourea dioxide, aliphatic amine and soluble metal salt and use thereof in textile printing - Google Patents

Discharge printing paste based on thiourea dioxide, aliphatic amine and soluble metal salt and use thereof in textile printing Download PDF

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Publication number
GB2305941A
GB2305941A GB9520148A GB9520148A GB2305941A GB 2305941 A GB2305941 A GB 2305941A GB 9520148 A GB9520148 A GB 9520148A GB 9520148 A GB9520148 A GB 9520148A GB 2305941 A GB2305941 A GB 2305941A
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United Kingdom
Prior art keywords
fabric
printing
printing paste
thiourea dioxide
metal salt
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GB9520148A
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GB9520148D0 (en
GB2305941B (en
Inventor
Ian Durham Rattee
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WACE UK Ltd
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WACE UK Ltd
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Publication date
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Priority to GB9520148A priority Critical patent/GB2305941B/en
Publication of GB9520148D0 publication Critical patent/GB9520148D0/en
Priority to US08/725,697 priority patent/US5846266A/en
Publication of GB2305941A publication Critical patent/GB2305941A/en
Application granted granted Critical
Publication of GB2305941B publication Critical patent/GB2305941B/en
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • 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
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • 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
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6491—(Thio)urea or (cyclic) derivatives
    • 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
    • D06P1/653—Nitrogen-free carboxylic acids or their salts
    • D06P1/6533—Aliphatic, araliphatic or cycloaliphatic
    • 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
    • D06P1/673—Inorganic compounds
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/67341—Salts or hydroxides of elements different from the alkaline or alkaline-earth metals or with anions containing those elements
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/15—Locally discharging the 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/15—Locally discharging the dyes
    • D06P5/158—Locally discharging the dyes with other compounds

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)

Abstract

By using printing pastes containing thiourea dioxide together with ammonia/aliphatic amine and a soluble metal salt, fabric discharge printing processes may be developed which have the advantage of decorating fabric webs, garments or garment panels effectively, even in dry heat conditions, whilst avoiding contamination of such fabrics with undesirable residues, particularly formaldehyde. A process of decorating dyed fabric comprises the steps of: applying such a printing paste to desired image areas to form a design on the fabric (the thiourea dioxide in the printing paste being capable of reacting with the dye in the fabric at least substantially to destroy its colour and subjecting the applied paste to a treatment for fixing the design in the fabric, such as dry heating or steam treatment. Such printing pastes are also claimed per se.

Description

IMPROVEMENTS IN TEXTILE PRINTING This invention relates to the printing of fabrics and improvements therein.
There are many occasions in which it is desired to produce a pattern or design on fabrics other than by weaving or knitting a pattern or design into them by using threads of different colours. The method by which this aim is most often achieved is by the use of a printing process of one kind or another.
An important variant of textile printing is the process of discharge printing whereby a suitably dyed fabric is printed with a suitable printing ink which contains a chemical (or chemicals) capable of destroying the chromogenic system of the dyes under appropriate conditions, usually heating or steaming. This destruction of the ground colour of the fabric provides a coloured fabric with a design of substantially uncoloured material. In an important variant of the process the printing ink additionally may contain colouring materials which are resistant to the chromogen destroying reactions of discharging and also a means of fixing such colouring materials to the fabric under the physical conditions of discharging. Such so-called "illuminated" discharge prints generally are produced using vat dyes or resin bonded pigments as colouring materials.
It is observed that throughout this specification the term "colouring materials" is used to indicate a pigment or a dyestuff which will give a coloured effect, and the term is used to include both black and white as well as spectral colours. The chemicals used substantially to destroy the colouring materials in discharge printing processes will hereinafter be referred to as "discharging agents1'.
A variety of procedures are known for achieving discharge printing of fabrics.
Discharge printing processes have been described in which a dyed fabric, usually cotton or some other cellulosic or substantially cellulosic material, is printed with a colouring material containing a discharging agent and dried. At this stage, little or no discharge effect may be seen. The dried print is then steamed at, typically, 102-1040C for several minutes, during which time the discharge reactions proceed. The fabric is then washed off, dried and processed further if required.
EP-A-0036252 describes a process of decorating dyed fabric which is printed with a first colouring material containing a discharging agent and then dried to fix it to the fabric. A second colouring material is also applied, before or after the first. The first prevents some of the dye in the second from becoming fixed to the fabric. It is necessary to wash off the fabric to remove such dye as has been prevented from fixing, before the effects of the process are visible.
EP-A-0416888 describes a process of decorating a dyed fabric where the fabric is printed with a colouring material which contains a discharging agent and also an unusually high concentration of humectant. The fabric is heated between impermeable layers at a high enough temperature to produce localised superheated steam from the water in the printing ink to promote the discharge reactions. This procedure has the advantage that the heat treatment is shorter and produces the discharge design within a short time of printing, thus allowing early inspection of the print quality. Printing ink formulations can also be devised for this procedure which permit the final washing off stage to be optional.
A further discharge printing process is where the dyed fabric is printed with a specially formulated discharge ink containing pigments and pigment bonding agents, urea or a substituted urea and a discharging agent formulated so that the discharge effect is produced during a simple drying and baking operation designed to fix the pigment.
Typical conditions for this kind of procedure may be provided by an oven operating at 190-2000C with a treatment time of 1-2 minutes. This procedure requires no steaming or washing off and is particularly advantageous for printing garments or garment panels, socalled "unit printing", as distinct from the printing of continuous web fabric which normally utilises any of the other above described procedures.
In the discharge printing of fabrics, for example cellulosic or substantially cellulosic fabrics, two kinds of discharging agents are typically used, both designed to effect destruction of the ground shade dye chromogen by reduction reactions. The most favoured are the metal salts of formaldehyde-sulphoxylic acid, of general formula M(SO2.CH2.OH)N, where M is a metal cation and N is the valency of the metal cation. These compounds are generally produced by reaction of formaldehyde with the appropriate metal sulphite, followed by reduction. Zinc, sodium and calcium salts are typically used. The zinc salt is particularly useful, especially when illuminated prints are to be produced since zinc formaldehydesulphoxylate has an acid reaction favourable to the curing of the acrylic binding agents generally used in such a process.Furthermore, reduction under mildly acid conditions generally favours the production of more weakly coloured degradation products from the discharge reactions than is obtained when using the alkaline sodium or calcium salts.
However, a serious disadvantage of using these discharging agents is that during the discharge reaction formaldehyde is liberated. While some of it escapes into the atmosphere, a high proportion is retained by the fabric. This residue of formaldehyde is readily removed by a washing off stage during fabric processing, but if the fabric is insufficiently washed after the printing process or washing off is omitted as, for example, during the procedure typically used in the so-called "unit printing" process described above, then significant amounts of formaldehyde, perhaps as much as 2000-3000 parts per million, will be present on the fabric.
Formaldehyde is a known carcinogen and irritant and accordingly, fabric bearing such a residue may represent a health hazard or provide a skin sensitisation problem to those coming into contact with the fabric, such as those who work with the fabric to make garments or the first wearer of a garment made from the fabric.
An alternative, but less frequently used, discharging agent is thiourea dioxide which re-arranges under alkaline conditions to form formamidine sulphinic acid.
This, like zinc formaldehyde-sulphoxylate, breaks down during the discharge printing process to the highly reactive sulphoxylic acid, but neither contains nor produces any formaldehyde. However, because it has been generally regarded as an alkaline discharging agent producing, as a consequence, coloured discharge products, thiourea dioxide has limited use in discharge printing.
In addition, it has been possible to use thiourea dioxide effectively only on processes involving steaming, as such conditions have, until now, been found necessary for the releasing of the active reaction products. Consequently, it has not been possible to use thiourea dioxide in procedures which do not utilise steam, such as the "unit printing" procedure described above, notwithstanding the fact that it offers, potentially at least, a valuable alternative to zinc formaldehyde sulphoxylate because it leaves no formaldehyde containing residues on the unwashed printed fabric. The present invention addresses this problem by providing a formaldehyde free discharging agent which is effective in both dry heat and steam conditions.
According to the present invention there is provided a process of decorating dyed fabrics comprising the steps of: applying a printing paste to desired image areas to form a design in the fabric, the printing paste containing at least one reagent capable of reacting with the dye in the fabric at least substantially to destroy its colour, the or one of the reagents being thiourea dioxide, and subjecting the applied paste to a treatment for fixing the design in the fabric, characterised in that the printing paste also contains at least one aliphatic amine or ammonia compound, together with at least one soluble metal salt. Preferably the soluble metal salt is a zinc or calcium salt, zinc being the most preferable.
Such a discharge printing paste which contains, in addition to thiourea dioxide, an aliphatic amine or ammonia and a soluble zinc salt, can be used for the effective production of discharge effects under dry heat conditions as well as in procedures requiring steam treatment.
Instead of ammonia, a variety of aliphatic amines may be used such as mono-ethanolamine, di-ethanolamine, triethanolamine, mono-isopropanolamine and diisopropanolamine, but it is preferred to use monoethanolamine as this is found to yield discharge products which are less coloured. The amount of amine present should be such that, in the absence of the zinc salt and the thiourea dioxide, the pH exceeds 10.2. However, it is not necessary that the amine should be added before the zinc salt or thiourea dioxide for the effect to be produced.
The effect is produced by any water soluble zinc salt such as zinc chloride, sulphate, nitrate or acetate. The latter is preferred due to its weaker acid reaction and less deleterious effect than the other zinc salts on thickening agents normally present to provide an ink of printable viscosity.
Preferably the printing paste contains agents for assisting the colour destroying reaction of the fabric dye and discharging agent, such as acids, alkalis, reduction catalysts and the like.
Depending on the effect desired, the printing paste may contain colouring materials which are chemically stable to the discharging agent(s), and which are capable of being fixed to the fabric during the process of the present invention. To assist this fixation, agents may be present such as resin binders which are capable of polymerising to bind the colouring materials to the fabric. Acrylic or polyurethane resin emulsions have been found to be most suitable for this purpose.
Catalysts which promote the curing of the binder or binders may also be present in the printing paste.
Alternatively, discharge printed or decolorised image areas on the fabric may be overprinted with colouring materials to produce a design in a second printing step.
Other agents may be present in the discharge inks produced in accordance with the present invention to assist the printing process or enhance the properties of the printed fabrics. Examples include thickening agents, softening agents, flame proofing additives, wetting agents, and cross-linking agents.
The thickening agents may be derived from polyacrylic acid, polyurethanes, emulsified white spirit, materials derived from cellulose, guar gums, other carbohydrates or any other suitable material. Binding agents may be selected from the wide variety of binding agents available for the production of pigment prints on textiles as is the case also with regard to flame proofing or softening agents. Cross-linking agents include the condensation products of formaldehyde with urea, urea derivatives, melamine or triazones, as well as glyoxal and 2,2'-dimethoxy ethanol.
An example of a typical formulation and procedure in accordance with the present invention is given below: A printing paste is prepared containing (parts by weight): Acrylic polymer aqueous emulsion (Alcoprint PBA ex Allied Colloids Plc) 18.0 Urea 12.0 Hydroxymethyl cellulose (2.5% by weight aqueous Solution) 14.0 White Spirit (as a 70% by weight aqueous emulsion) 49.5 Mono-ethanolamine 1.5 Zinc Acetate 5.0 Copper Phthalocyanine (as an aqueous dispersion) 5.0 Thiourea dioxide 6.0 Alcoprint is a Registered Trade Mark.
A knitted garment panel dyed to a red shade using Remazol (Registered Trade Mark) Brilliant Red 3B (ex Hoechst UK Ltd) is screen printed with a design using the above ink and then passed down a drying/curing oven operating at 2000C with a total heating time of 2 minutes. The red shade is destroyed to leave a bright blue decoration which is fast to washing. If the mono-ethanolamine or the zinc acetate is omitted from the above recipe, the red shade is very poorly discharged and the decoration is of a dull and unsatisfactory shade.
If the printed areas of the fabric are tested for free formaldehyde using any of the standard tests approved by the British Standards Institute, the ISO or other recognised authority, the formaldehyde content is found to below, < 100 parts per million.

Claims (8)

1. A process of decorating dyed fabric comprising the steps of: applying a printing paste to desired image areas to form a design on the fabric, the printing paste containing at least one reagent capable of reacting with the dye in the fabric at least substantially to destroy its colour, the or one of the reagents being thiourea dioxide, and subjecting the applied paste to a treatment for fixing the design in the fabric, characterised in that the printing paste also contains at least one aliphatic amine or ammonia compound together with at least one soluble metal salt.
2. A process according to Claim 1 wherein the or one metal salt is a zinc or calcium salt.
3. A process as claimed in Claim 1 or 2 wherein the treatment for fixing the design in the fabric comprises a dry heat treatment.
4. A process as claimed in any one of the preceding Claims wherein the or one aliphatic amine is selected from a group comprising mono-ethanolamine, di-ethanolamine, tri-ethanolamine and di isopropanolamine.
5. A process as claimed in any of one of the preceding Claims wherein the or one of the soluble metal salts is selected from the group comprising zinc chloride, zinc sulphate, zinc nitrate or zinc acetate.
6. A process as claimed in any preceding Claim wherein the printing paste comprises colouring materials and means for fixing the colouring materials in the fabric.
7. A process as claimed in any preceding claim wherein the printing paste comprises at least one agent for assisting the colour-destroying reaction and/or at least one agent for improving the properties of the fabric.
8. A printing paste for use in a process as claimed in any preceding claim wherein the paste comprises thiourea dioxide together with an aliphatic amine/ammonia and a soluble metal salt.
GB9520148A 1995-10-03 1995-10-03 Discharge printing paste based on thiourea dioxide, aliphatic amine and soluble metal salt and use thereof in textile printing Expired - Lifetime GB2305941B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB9520148A GB2305941B (en) 1995-10-03 1995-10-03 Discharge printing paste based on thiourea dioxide, aliphatic amine and soluble metal salt and use thereof in textile printing
US08/725,697 US5846266A (en) 1995-10-03 1996-10-03 Fabric printing

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9520148A GB2305941B (en) 1995-10-03 1995-10-03 Discharge printing paste based on thiourea dioxide, aliphatic amine and soluble metal salt and use thereof in textile printing

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GB9520148D0 GB9520148D0 (en) 1995-12-06
GB2305941A true GB2305941A (en) 1997-04-23
GB2305941B GB2305941B (en) 1999-03-17

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2310867B (en) * 1996-03-06 2000-06-14 Wace Uk Ltd Printing paste for discharge printing based on thiourea dioxide and calcium, magnesium or zinc hydroxide
WO2015118285A1 (en) 2014-02-10 2015-08-13 Sericol Limited Printing ink
EP3971248A1 (en) * 2020-09-22 2022-03-23 CHT Germany GmbH Formaldehyde-free printing ink for printing onto fabrics

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115029945A (en) * 2022-05-30 2022-09-09 江苏泰慕士针纺科技股份有限公司 Color stripping process of deep color knitted fabric

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1026236A (en) * 1964-02-25 1966-04-14 Hardman & Holden Ltd Improvements relating to the discharge printing of textile fabrics
US4400174A (en) * 1981-04-04 1983-08-23 Basf Aktiengesellschaft Process for printing on synthetic fibers: reducing agent and alkoxylated amine for discharge
JPH0196297A (en) * 1987-10-09 1989-04-14 Lion Corp Bleaching agent composition
JPH0196298A (en) * 1987-10-09 1989-04-14 Lion Corp Bleaching agent composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1026236A (en) * 1964-02-25 1966-04-14 Hardman & Holden Ltd Improvements relating to the discharge printing of textile fabrics
US4400174A (en) * 1981-04-04 1983-08-23 Basf Aktiengesellschaft Process for printing on synthetic fibers: reducing agent and alkoxylated amine for discharge
JPH0196297A (en) * 1987-10-09 1989-04-14 Lion Corp Bleaching agent composition
JPH0196298A (en) * 1987-10-09 1989-04-14 Lion Corp Bleaching agent composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
WPI Abstract Accession No 89-155166/21 & JP 01 096 297 A [1989] *
WPI Abstract Accession No 89-155167/21 & JP 01 096 298 A [1989] *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2310867B (en) * 1996-03-06 2000-06-14 Wace Uk Ltd Printing paste for discharge printing based on thiourea dioxide and calcium, magnesium or zinc hydroxide
WO2015118285A1 (en) 2014-02-10 2015-08-13 Sericol Limited Printing ink
EP3971248A1 (en) * 2020-09-22 2022-03-23 CHT Germany GmbH Formaldehyde-free printing ink for printing onto fabrics
WO2022063716A1 (en) * 2020-09-22 2022-03-31 CHT Germany GmbH Formaldehyde-free printing ink for printing onto fabrics

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Publication number Publication date
GB9520148D0 (en) 1995-12-06
GB2305941B (en) 1999-03-17

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Expiry date: 20151002