GB2036809A - Transfer Printing - Google Patents
Transfer Printing Download PDFInfo
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- GB2036809A GB2036809A GB7847771A GB7847771A GB2036809A GB 2036809 A GB2036809 A GB 2036809A GB 7847771 A GB7847771 A GB 7847771A GB 7847771 A GB7847771 A GB 7847771A GB 2036809 A GB2036809 A GB 2036809A
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3643—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from quinolines or hydrogenated quinolines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0829—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-CN)(-alkenylene/-alkynylene-CN)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3686—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and oxygen as heteroatom
-
- 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
- D06P5/003—Transfer printing
- D06P5/004—Transfer printing using subliming dyes
- D06P5/006—Transfer printing using subliming dyes using specified dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
A transfer printing sheet comprises a non-textile support bearing a disperse azo dye having the formula: <IMAGE> wherein R1 represents 0 to 4 substituents, which may be the same or different, selected from alkyl radicals having from 1 to 4 carbon atoms, alkoxy radicals having from 1 to 4 carbon atoms, F, Cl, Br, I, -CHF2, -CF3, -CN, -COOR2, -NO2, - SO2F, -SO2CHF2, -SO2CF3, -SR2 and -OR2, wherein R2 is methyl or ethyl; and A represents an aniline, tetrahydroquinoline or benzomorpholine coupling component. Polyamides and polyesters are printed with the above transfers.
Description
SPECIFICATION
Transfer Printing
This invention relates to materials for use in transfer printing, and to methods thereof.
Some techniques of transfer printing are described in an article by D. Burtonshaw, International
Dyer and Textile Printer, 335-340, 1 971. In the most widely used technique, which is the one to which the present invention relates, a dye capable of sublimation is applied to a non-textile support such as paper or other suitable medium, and the dye is transferred by the action of heat to a contiguous material.
In accordance with the present invention, there is provided a transfer printing sheet which comprises a non-textile support bearing a disperse azo dye having the formula:
wherein R1 represents 0 to 4 substituents, which may be the same or different, selected from alkyl radicals having from 1 to 4 carbon atoms, alkoxy radicals having from 1 to 4 carbon atoms, F, CI, Br, I, -CHF2, -CF3, -CN, -COOR2, -NO2, -SO2F, -SO2CHF2, -SO2CF3, -SR2 and -OR2, wherein
R2 is methyl or ethyl;
and A represents an aniline, tetrahydroquinoline or benzomorpholine coupling component.
Preferably R1 represents CI, -CF3 or -NO2.
Preferred aniline coupling components have the formula:
wherein R3 and R4 are individually selected from hydrogen; alkyl radicals having from 1 to 4 carbon atoms, which may be substituted with halogen or cyano; and alkenyl radicals having from 1 to 4 carbon atoms; and R5 and R, are individually selected from hydrogen, alkyl radicals having from 1 to 4 carbon atoms, alkoxy radicals having from 1 to 3 carbon atoms; acetamido or trifluoroacetamidoi
More preferably, R3 and R4 are individually selected from the alkyl and alkenyl radicals specified above; R5 is selected from the alkyl and alkoxy radicals specified above; and Re is selected from the alkyl and alkoxy radicals specified.above, and triflornacetamido.
Most preferably, R3 and R4 are individually selected from alkyl radicals having from 1 to 4 carbon atoms.
Preferred tetrahydroquinoline coupling components have the formula
wherein R7 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms (and which may be substituted with halogen, cyano, hydroxy, CH3COO- or C2H5COO-), or an alkenyl radical having from 1 to 4 carbon atoms; R8 to R13 are selected from hydrogen or methyl; and R14 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, acetamido or trifluoroacetamido.
More preferably, R, is an alkyl radical having from 1 to 4 carbon atoms, and R14 is an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, or trifluoroacetamido.
Most preferably, R7 and R14 are alkyl groups having from 1 to 4 carbon atoms.
Preferred benzomorpholine coupling components have the formula:
wherein R15 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, acetamido or trifluoroacetamido; and R16 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms (and which may be substituted with halogen, cyano, hydroxy, CH3COO- or C2H5COO-), or an alkenyl radical having from 1 to 4 carbon atoms.
Preferably the dye is in a binder, for example a suitable synthetic, semisynthetic or natural resin.
Cellulose esters and ethers may be used as binders.
The non-textile support may be paper, e.g. paper of low porosity, or metal, e.g. an aluminium foil, or a plastics film. All of these supports may be attached to another support on the non-dye-bearing side.
The dye may be applied in a printing ink by the flexographic, gravure, letterpress, silk screen or lithographic process. The dye will usually, although not necessarily, be applied in an imagewise distribution. More than one dye may be applied to the support.
Any conventional printing ink formulation may be used. Examples of suitable printing ink formulations will be found in "Printing Inks", A. Williams, Noyes Data Corporation (USA) 1972, and "Printing Ink Manual", The Society of British Printing Ink Manufacturers, Heffer, Cambridge, 1969.
Also according to the present invention there is provided a method of transfer printing a fabric or film of a polyamide or polyester, which comprises placing the dye-bearing side of a transfer printing sheet as defined above in contact with the fabric or film and subjecting the sheet and fabric or film to heat to transfer at least some of the dye from the sheet to the fabric or film.
The transfer of the dye may take place at atmospheric pressure or reduced or increased pressure, or under vacuum, and at a temperature of 1 800C to 2300C. The pressure between the sheet and fabric or film may be, for example, up to 10 kilopascals. Higher pressures may be used. Apparatus is commercially available for performing transfer printing.
Also according to the present invention, there is provided a fabric or film of a polyamide or polyester which has been transfer printed by a method as defined above.
Also according to the present invention, there is provided a printing ink containing a disperse azo dye having the above formula, preferably in a binder.
The materials and methods of the present invention may be used to apply a dye or dyes to various polyamides and polyesters. The polymers may be in the form of coatings on other substrates, e.g.
metal, leather, cotton or wool. The polymers may be in the form of woven, knitted, bonded or laminated fabrics, or pile fabrics, e.g. carpets.
The dyes carried by the transfer printing sheets of the present invention have good volatility in transfer printing, and give strong bright bluish-red to greenish-blue shades on polyamides and polyesters. These shades have good fastness to light and to wet treatments. Dyes having halogen and trifluoromethyl substituents on the benzoisothiazole structure can be used to obtain strong reddishblue shades on polyamides and polyesters, with particularly good wet fastness on polyamide fabrics.
Dyes for use in the invention can be prepared by conventional diazotisation procedures, such as the following.
Example 1
Sodium nitrite (0.72 g) was added slowly with stirring to concentrated sulphuric acid (5 ml), and the temperature was allowed to rise to 70cm. The mixture was cooled to 0--5 OC, and 10 ml of a mixture of propionic and acetic acids (1:5 by volume) was added drop by drop while the temperature was kept below 1 50C. The mixture was cooled to below 50C while 3-amino-5-nitro-2,1benzoisothiazole (1.95 g) was added in portions, followed by the addition drop by drop of another 10 ml of the mixture of propionic and acetic acids. Diazotisation was allowed to proceed for two hours, the reaction mixture being stirred and kept below 50C, and then a little urea was added to remove excess nitrosylsulphuric acid. The diazonium solution was slowly added to a solution of N,N-diethyl-mtoluidine (1.65 g) in acetic acid (10 ml) at less than 10 C. Coupling was allowed to proceed for30 minutes, and then the mixture was poured into ice-water. The solid dye was filtered off, washed with water, and dried.
Examples 2 to 7
By the procedure of Example 1, dyes were prepared from the following diazo components and couplers.
Example Diazo Component Coupler
2 3-amino-2,1-benzoisothiazole N,N-diethylaniline
3 3-amino-2,1 -benzoisothiazole N,N-diethyl-m-toluidine
4 3-amino-5-nitro-2,1 -benzoiso- 3-chloro-N,N-diethyl
thiazole aniline
5 3-amino-5-chloro-2,1-benzoiso- N,N-dipropyl-m
thiazole toluidine
6 3-amino-5-chloro-2,1 -benzoiso- N-butyl-2,5-dimethyl
thiazole aniline
7 3-amino-6-trifluoromethyl-2,1- N,N-diethyl-m-ethyl
benzoisothiazole aniline
Each of the dyes from Examples 1 to 7 was made up into a printing ink by ball milling it for 48 hours in a 9:1 mixture of ethanol and ethylene glycol, using ethyl cellulose (Hercules N-7 grade) as a binder.
The resulting inks were printed on to flexographic heat transfer paper, using roller coating bars.
The samples of printed paper were used for transfer printing on to nylon fabric at 2000C for 30 seconds, and on to polyester fabric at 210 C for 30 seconds. The resulting prints had good strength and good fastness to light and to wet treatments. The dye of Example 1 was greenish blue; the dyes of
Examples 2 and 3 were bluish red; the dye of Example 4 was blue; and the dyes of Examples 5, 6 and 7 were reddish blue.
Examples 8 to 43
By the procedure of Example 1, dyes conforming to the following general formula were prepared:
Example No. R1 R5 R6 Colour
8 5-CI H -CH3 Reddish blue
9 5-CF3 H -CH3 Blue
10 5-CI H -CH3 Blue
6-CF3
11 7-CF3 H -CH3 Blue
12 7-CI H -CH3 Reddish blue
13 5-CI H -CH3 Blue
7-CF3
14 5-NO2 H -CH3 Greenish blue
7-Br
15 5-CI -OCH3 -OCH3 Greenish blue
16 5-CF3 -OCH3 -OCH3 Greenish blue
17 5-CI -OCH3 -OCH3 Greenish blue
6-CF3
18 7-CF3 -OCH3 -OCH3 Greenish blue
19 7-CI -OCH3 -OCH3 Greenish blue
20 5-CI -OCH3 -OCH3 Greenish blue
7-CF3
Example No.R, R5 R, Colour
21 5-NO2 -OCH3 -OCH3 Greenish blue
7-Br
22 5-Cl -OCH3 -CH3 Blue
23 5-CF3 -OCH3 -CH3 Greenish blue
24 5-Cl -OCH3 -CH3 Greenish blue
6-CF3
25 7-CF3 -OCH3 -CH3 Greenish blue
26 7-Cl -OCH3 -CH3 Greenish blue
27 5-Cl -OCH3 -CH3 Greenish blue
7-CF3
28 5-NO2 -OCH3 -CH3 Greenish blue
7-Br
29 5-CI -OCH3 -NHCOCH3 Greenish blue
30 5-CF3 -OCH3 -NHCOCH3 Greenish blue
31 5-CI -OCH3 -NHCOCH3 Greenish blue
6-CF3
32 7-CF3 -OCH3 -NHCOCH3 Greenish blue
33 7-CI -OCH3 -NHCOCH3 Greenish blue
34 5-CI -OCH3 -NHCOCH3 Greenish blue
7-CF3
35 5-NO2 -OCH3 -NHCOCH3 Greenish blue
7-Br
36 5-CI -OCH3 -NHCOCH3 Greenish blue
37 5-CF3 -OCH3 -NHCOCH3 Greenish blue
38 5-CI OCH3 -NHCOCH3 Greenish blue
6-CF3
39 7-CF3 -OCH3 -NHCOCH3 Greenish blue
40 7-Cl -OCH3 -NHCOCH3 Greenish blue
41 5-Cl -OCH3 -NHCOCH3 Greenish blue
7-CF3
42 5-NO2 -OCH3 -NHCOCH3 Greenish blue
7-Br
43 5-CF3 H -NHCOCH3 Blue
Examples 44-48
By the procedure of Example 1, dyes conforming to the following general formula were prepared.
Example
No. R1 R5 R6 R3 R4 Colour
44 7-CF3 H -CH3 -C2H4CN -C2H4CN Reddish
blue
45 7-CF3 -OCH3 -OCH3 -C2H4CN -C2H4CN Blue
46 4-CF3 -OCH3 -CH3 H -C2H4OH Reddish
Blue
47 5-Cl H -CH3 -C2H4CN -C2H4CN Blue
7-CF3
48 4-CF3 -OCH3 -OCH3 -C2H4OH -C2H4OH Greenish
6-CF3 blue
Examples 49 to 62
By the procedure of Example 1, dyes conforming to the following general formula were prepared.
Example No. R@ R@@ Colour
49 5-Cl H Blue
50 5-CF3 H Blue
51 5-CI H Blue
6-CF3
52 7-CF3 H Blue
53 7-Cl H Blue
54 5-Cl H Blue
7-CF3
55 5-NO2 H Blue
7-Br
56 5-Cl -CH3 Blue
57 5-CF3 -CH3 Greenish blue
58 5-CI -CH3 Greenish blue
6-CF3
59 7-CF3 -CH3 Blue
Example No. R1 R14 Colour
60 7-CI -CH3 Blue
61 5-CI -CH3 Greenish blue
7-CF3
62 5-NO2 -CH3 Greenish blue
7-Br 'Examples 63-65 By the procedure of Example 1, dyes conforming to the following general formula were prepared.
Example No. R@ R@ R@ R14 Colour
63 5-CF3 -C2H4NHCOCH3 -CH3 -CH3 Greenish blue
64 5-CF3 -C2H4OH H -NHCOCH3 Blue
65 5-CI -C2H4OH H -CH3 Blue
6-CF3
Example 66
By the procedure of Example 1, a blue dye having the following formula was prepared.
All these dyes can be used in accordance with the invention.
Claims (29)
1. A transfer printing sheet which comprises a non-textile support bearing a disperse azo dye having the formula:
wherein R1 represents 0 to 4 substituents, which may be the same or different, selected from alkyl radicals having from 1 to 4 carbon atoms. alkoxy radicals having from 1 to 4 carbon atoms, F,Cl,Br,I.
-CHF2, -CF3,-CN,-COOR2,-NO2, -SO2F, -SO2CHF2, -SO2CF3, -SR2 and -OR2, wherein R2 is methyl or ethyl; and A represents an aniline, tetrahydroquinoline or benzomorpholine coupling component.
2. A sheet as claimed in Claim 1, wherein R, is selected from Cl, -CF3 and -NO2.
3. A sheet as claimed in Claim 1 or 2, wherein A is an aniline coupling component having the formula:
wherein R3 and R4 are individually selected from hydrogen; alkyl radicals having from 1 to 4 carbon atoms, which may be substituted with halogen or cyano; and alkenyl radicals having from 1 to 4 carbon atoms; and R5 and R6 are individually selected from hydrogen, alkyl radicals having from 1 to 4 carbon atoms, alkoxy radicals having from 1 to 3 carbon atoms; acetamido or trifluoroacetamido.
4. A sheet as claimed in Claim 3, wherein R3 and R4 are individually selected from the alkyl and alkenyl radicals specified therein; R5 is selected from the alkyl and alkoxy radicals specified therein; and
R6 is selected from the alkyl and alkoxy radicals specified therein, and trifluoroacetamido.
5. A sheet as claimed in Claim 4, wherein R3 and R4 are individually selected from alkyl radicals having from 1 to 4 carbon atoms.
6. A sheet as claimed in Claim 1 or 2, wherein A is a tetrahydroquinoline coupling component having the formula:
wherein R7 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms (and which may be substituted with halogen, cyano, hydroxy, CH3COO- or C2H5COO-), or an alkenyl radical having from 1 to 4 carbon atoms; R8 to R13 are selected from hydrogen or methyl; and Ra4 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, acetamido or trifluoroacetamido.
7. A sheet as claimed in Claim 6, wherein R7 is an alkyl radical having from 1 to 4 carbon atoms, and R14 is an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, or trifluoroacetamido.
8. A sheet as claimed in Claim 7, wherein R7 and R14 are alkyl groups having from 1 to 4 carbon atoms.
9. A sheet as claimed in Claim 1 or 2, wherein A is a benzomorpholine coupling component having the formula:
wherein R15 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 3 carbon atoms, acetamido or trifluoroacetamido; and R16 is hydrogen, an alkyl radical having from 1 to 4 carbon atoms (and which may be substituted with halogen, cyano, hydroxy, CH3COO- or C2H5COO-), or an alkenyl radical having from 1 to 4 carbon atoms.
10. A sheet as claimed in any one of Claims 1 to 9, wherein the dye is in a binder.
11. A sheet as claimed in any one of Claims 1 to 10, wherein the support is paper.
12. A sheet as claimed in Claim 1 and substantially as hereinbefore described.
1 3. A method of transfer printing a fabric or film of a polyamide or polyester, which comprises placing the dye-bearing side of a transfer printing sheet as claimed in Claim 1 in contact with the fabric or film and subjecting the sheet and fabric or film to heat to transfer at least some of the dye from the sheet to the fabric or film.
14. A method as claimed in Claim 13, wherein the sheet is as claimed in Claim 2.
15. A method as claimed in Claim 13, wherein the sheet is as claimed in Claim 3, 4 or 5.
1 6. A method as claimed in Claim 13, wherein the sheet is as claimed in Claim 6, 7 or d.
1 7. A method as claimed in Claim 13, wherein the sheet is as claimed in Claim 9.
18. A method as claimed in Claim 13, wherein the sheet is as claimed in Claim 10 or 11.
19. A method as claimed in any one of Claims 13 to 18, wherein transfer is effected at a temperature of 1 800C to 2300C.
20. A method as claimed in Claim 13 and substantially as hereinbefore described.
21. A fabric or film of a polyamide or polyester which has been transfer printed by a method as claimed in Claim 13.
22. A fabric or film of a polyamide or polyester which has been transfer printed by a method as claimed in any one of Claims 14 to 1 9.
23. A transfer printing ink containing a disperse azo dye having the formula set out in Claim 1.
24. A printing ink as claimed in Claim 23, wherein R, in the dye formula is as claimed in Claim 2.
25. A printing ink as claimed in Claim 23 or 24, wherein A in the dye formula is as claimed in
Claim 3, 4 or 5.
26. A printing ink as claimed in Claim 23 or 24, wherein A in the dye formula is as claimed in
Claim 6,7or8.
27. A printing ink as claimed in Claim 23 or 24, wherein A in the dye formula is as claimed in
Claim 9.
28. A printing ink as claimed in any one of Claims 23 to 27, also containing a binder.
29. A printing ink as claimed in Claim 23 and substantially as hereinbefore described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7847771A GB2036809B (en) | 1978-12-08 | 1978-12-08 | Transfer printing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7847771A GB2036809B (en) | 1978-12-08 | 1978-12-08 | Transfer printing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2036809A true GB2036809A (en) | 1980-07-02 |
| GB2036809B GB2036809B (en) | 1982-08-25 |
Family
ID=10501608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7847771A Expired GB2036809B (en) | 1978-12-08 | 1978-12-08 | Transfer printing |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2036809B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0216483A1 (en) * | 1985-08-27 | 1987-04-01 | Zeneca Limited | Thermal transfer printing |
| US4681932A (en) * | 1984-07-07 | 1987-07-21 | Bayer Aktiengesellschaft | Benzoisothiazole azo dyestuffs |
| EP0227095A3 (en) * | 1985-12-24 | 1988-07-27 | Eastman Kodak Company | Magenta dye-donor element used in thermal dye transfer |
| EP0235939A3 (en) * | 1986-02-28 | 1989-05-03 | Imperial Chemical Industries Plc | Thermal transfer printing |
| US4874392A (en) * | 1986-08-01 | 1989-10-17 | Sandoz Ltd. | Monoazo dyes having a substituted 1,4-phenylene coupling component radical having one C8-14 alkyl group or moiety |
| US5234887A (en) * | 1986-02-28 | 1993-08-10 | Imperial Chemical Industries Plc | Thermal transfer printing |
| US5691458A (en) * | 1996-09-18 | 1997-11-25 | Polaroid Corporation | Benzoisothiazole azo dyes |
| CN104087016A (en) * | 2014-06-05 | 2014-10-08 | 浙江龙盛集团股份有限公司 | A disperse dyestuff composition, a disperse dyestuff product and applications of the product |
-
1978
- 1978-12-08 GB GB7847771A patent/GB2036809B/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4681932A (en) * | 1984-07-07 | 1987-07-21 | Bayer Aktiengesellschaft | Benzoisothiazole azo dyestuffs |
| US4773915A (en) * | 1984-07-07 | 1988-09-27 | Bayer Aktiengesellschaft | Benzisothiazole azo dye for synthetic fibers |
| EP0216483A1 (en) * | 1985-08-27 | 1987-04-01 | Zeneca Limited | Thermal transfer printing |
| US4764178A (en) * | 1985-08-27 | 1988-08-16 | Imperial Chemical Industries Plc | Thermal transfer printing: hetero-aromatic azo dye |
| USRE36357E (en) * | 1985-08-27 | 1999-10-26 | Imperial Chemical Industries Plc | Thermal transfer printing: hetero-aromatic azo dye |
| EP0227095A3 (en) * | 1985-12-24 | 1988-07-27 | Eastman Kodak Company | Magenta dye-donor element used in thermal dye transfer |
| EP0235939A3 (en) * | 1986-02-28 | 1989-05-03 | Imperial Chemical Industries Plc | Thermal transfer printing |
| US5234887A (en) * | 1986-02-28 | 1993-08-10 | Imperial Chemical Industries Plc | Thermal transfer printing |
| US4874392A (en) * | 1986-08-01 | 1989-10-17 | Sandoz Ltd. | Monoazo dyes having a substituted 1,4-phenylene coupling component radical having one C8-14 alkyl group or moiety |
| US5691458A (en) * | 1996-09-18 | 1997-11-25 | Polaroid Corporation | Benzoisothiazole azo dyes |
| CN104087016A (en) * | 2014-06-05 | 2014-10-08 | 浙江龙盛集团股份有限公司 | A disperse dyestuff composition, a disperse dyestuff product and applications of the product |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2036809B (en) | 1982-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |