US3186787A - Process for dyeing or printing shaped structures of linear aromatic poly- esters, especially polyethylene ter- ephthalates - Google Patents
Process for dyeing or printing shaped structures of linear aromatic poly- esters, especially polyethylene ter- ephthalates Download PDFInfo
- Publication number
- US3186787A US3186787A US3186787DA US3186787A US 3186787 A US3186787 A US 3186787A US 3186787D A US3186787D A US 3186787DA US 3186787 A US3186787 A US 3186787A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- esters
- ephthalates
- shaped structures
- aromatic poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000004043 dyeing Methods 0.000 title claims description 16
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims description 10
- 125000003118 aryl group Chemical group 0.000 title description 4
- 229920000728 polyester Polymers 0.000 title description 4
- 239000002657 fibrous material Substances 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 239000000969 carrier Substances 0.000 description 14
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 polyethylene terephthalate Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N 2-Phenylphenol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 238000009998 heat setting Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-Methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-Anisic acid Chemical class COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Definitions
- the dyeing is carried out in the presence of a carrier 7 at a temperature within the range of about 95 to 105 C. and preferably about 100 C. or, by the high temperature process, in the absence of a carrier at a temperature within the range of about 12 to 140 C. and
- Printing is advantageously carried out by applying the dispersed dyestuff to the shaped structures by printing and subjecting the printed shaped structure to a short dry heat treatment at a high temperature, for example, of about 200 C.
- the dyeings or prints produced according to the process of the present invention may be after-treated in an alkaline reducing bath which may contain, for example, sodium dithionite, sodium hydroxide and a detergent.
- the dyestufi shows a good affinity to structures of aromatic polyesters and a good ability of building up, even when dyeing at 100 C. in the presence of carriers.
- the dyeings obtained are distinguished by their excellent fastness to light and their very god fastness to thermo-fixation.
- Example 1 100 grams of yarn of polyethylene terephthalate are treated for 90 minutes at a goods-to-liquor ratio of 3,185,787 Patented June 1, 1965 ice 1:30 in a bath of 100 C. containing 0.8 gram of the disazo-dyestufi of phenol-(4 azo 1)-benzene-(4 azo 4)- phenol in a finely divided form and 4 grams per liter of a carrier based on o-phenyl phenol.
- the goods are soaped and then subjected to an after-treatment for 15 minutes at to C. in a reducing bath containing per liter 2 grams of sodium dithionite 2 ml. of sodium hydroxide solution of 38 B6. and 0.5 to 1 gram of a non-ionic synthetic detergenttpolyglycol ether) in order to improve their fastness to rubbing.
- a reddish yellow dyeing possessing a very good fastness to light and to thermofixation.
- Example 2 25 grams of a fabric of polyethylene terephthalate are printed with a printing paste containing per kilogram 50 grams of the disazo-dyestufi of phenol-(4 azo 1)-benzene- (4 azo 4)-phenol, 200 grams of narka rubber, 50 grams of napththoldiglycol ether and 700 grams of water. The goods are then dried, fixed for 30 seconds at 200 C. and finally subjected to an after-treatment in a reducing bath as described in Example 1. There is obtained a yellow print possessing good fastness properties.
- a process for dyeing and printing fibrous materials of polyethylene terephthalates which comprises applying to said materials at about to 140 C. from an aqueous dispersion the disazo dyestufi phenol-(4 azo 1)-benzene- (4 azo 4)-phenol of the formula 2.
Description
United States Patent of Germany No Drawing. Filed Dec. 17, 1962, Ser. No. 244,933
Claims priority, application Germany, Dec. 27, 1961, 4 Claims. (c1. 3-41 The dyeing is carried out in the presence of a carrier 7 at a temperature within the range of about 95 to 105 C. and preferably about 100 C. or, by the high temperature process, in the absence ofa carrier at a temperature within the range of about 12 to 140 C. and
preferably between about 125 and 130 C. Printing is advantageously carried out by applying the dispersed dyestuff to the shaped structures by printing and subjecting the printed shaped structure to a short dry heat treatment at a high temperature, for example, of about 200 C.
As carriers which are suitable for the process of the present invention there may be used, for example, o or p-phenyl phenol, salicylic acid esters, methyl salicylic acid esters, mono-, diand trichlorobenzenes, benzoic acid and methyl naphthalene. In order to improve the fastness to abrasion, the dyeings or prints produced according to the process of the present invention may be after-treated in an alkaline reducing bath which may contain, for example, sodium dithionite, sodium hydroxide and a detergent.
The dyestufi shows a good affinity to structures of aromatic polyesters and a good ability of building up, even when dyeing at 100 C. in the presence of carriers. The dyeings obtained are distinguished by their excellent fastness to light and their very god fastness to thermo-fixation.
The following examples serve to illustrate the invention but they are not intended to limit it thereto, the parts being by weight unless otherwise stated and the relationship of parts by weight to parts by volume being the same as that of the kilogram'to the liter.
Example 1 100 grams of yarn of polyethylene terephthalate are treated for 90 minutes at a goods-to-liquor ratio of 3,185,787 Patented June 1, 1965 ice 1:30 in a bath of 100 C. containing 0.8 gram of the disazo-dyestufi of phenol-(4 azo 1)-benzene-(4 azo 4)- phenol in a finely divided form and 4 grams per liter of a carrier based on o-phenyl phenol. The goods are soaped and then subjected to an after-treatment for 15 minutes at to C. in a reducing bath containing per liter 2 grams of sodium dithionite 2 ml. of sodium hydroxide solution of 38 B6. and 0.5 to 1 gram of a non-ionic synthetic detergenttpolyglycol ether) in order to improve their fastness to rubbing. There is obtained a reddish yellow dyeing possessing a very good fastness to light and to thermofixation.
Example 2 25 grams of a fabric of polyethylene terephthalate are printed with a printing paste containing per kilogram 50 grams of the disazo-dyestufi of phenol-(4 azo 1)-benzene- (4 azo 4)-phenol, 200 grams of narka rubber, 50 grams of napththoldiglycol ether and 700 grams of water. The goods are then dried, fixed for 30 seconds at 200 C. and finally subjected to an after-treatment in a reducing bath as described in Example 1. There is obtained a yellow print possessing good fastness properties.
We claim:
1. A process for dyeing and printing fibrous materials of polyethylene terephthalates, which comprises applying to said materials at about to 140 C. from an aqueous dispersion the disazo dyestufi phenol-(4 azo 1)-benzene- (4 azo 4)-phenol of the formula 2. The process as claimed in claim 1, wherein the dyeing is carried out in the presence of a carrier at a temperature between about 95 and C.
3. The process as claimed in claim 1, wherein the dyeing is carried out in the absence of a carrier at a temperature between about and C.
4. The process as claimed in claim 1, wherein the printed fibrous materials are exposed to a short dry heat treatment at about 200 C.
References Cited by the Examiner UNITED STATES PATENTS 2,663,612 12/53 Gibson.
2,881,045 4/59" Mecco et a1.
2,926,987 3/60 Freyermuth et a1.
2,934,397 4/60 Landerl.
3,096,140 7/63 Gaetani' 8/41 NORMAN G. TORCHIN, Primary Examiner.
Claims (1)
1. A PROCESS FOR DYEING AND PRINTING FIBROUS MATERIALS OF POLYETHYLENE TEREPHTHALATES, WHICH COMPRISES APPLYING TO SAID MATERIALS AT ABOUT 95 TO 140*C. FROM AN AQUEOUS DISPERSION THE DISAZO DYESTUFF PHENOL-(4 AZO 1)-BENZENE(4 AZO 4)-PHENOL OF THE FORMULA
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3186787A true US3186787A (en) | 1965-06-01 |
Family
ID=3457469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3186787D Expired - Lifetime US3186787A (en) | Process for dyeing or printing shaped structures of linear aromatic poly- esters, especially polyethylene ter- ephthalates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3186787A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3421829A (en) * | 1963-06-21 | 1969-01-14 | Ici Ltd | Process for colouring aromatic polyester and cellulose acetate textile materials with water-insoluble disazo dyestuffs |
| US3523935A (en) * | 1966-12-05 | 1970-08-11 | Gaf Corp | Disazo dyestuff containing m-cresol coupling components |
| US3997522A (en) * | 1969-05-31 | 1976-12-14 | Bayer Aktiengesellschaft | Disazo dyestuffs |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663612A (en) * | 1950-05-10 | 1953-12-22 | Du Pont | Process for coloring hydrophobic fiber |
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| US2926987A (en) * | 1956-04-30 | 1960-03-01 | Gen Aniline & Film Corp | Preparation of phenylphenol dyeing assistant compositions |
| US2934397A (en) * | 1955-10-26 | 1960-04-26 | Du Pont | Process for dyeing polyester fiber |
| US3096140A (en) * | 1959-04-16 | 1963-07-02 | Acna | Process for dyeing polyolefins |
-
0
- US US3186787D patent/US3186787A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663612A (en) * | 1950-05-10 | 1953-12-22 | Du Pont | Process for coloring hydrophobic fiber |
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| US2934397A (en) * | 1955-10-26 | 1960-04-26 | Du Pont | Process for dyeing polyester fiber |
| US2926987A (en) * | 1956-04-30 | 1960-03-01 | Gen Aniline & Film Corp | Preparation of phenylphenol dyeing assistant compositions |
| US3096140A (en) * | 1959-04-16 | 1963-07-02 | Acna | Process for dyeing polyolefins |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3421829A (en) * | 1963-06-21 | 1969-01-14 | Ici Ltd | Process for colouring aromatic polyester and cellulose acetate textile materials with water-insoluble disazo dyestuffs |
| US3523935A (en) * | 1966-12-05 | 1970-08-11 | Gaf Corp | Disazo dyestuff containing m-cresol coupling components |
| US3997522A (en) * | 1969-05-31 | 1976-12-14 | Bayer Aktiengesellschaft | Disazo dyestuffs |
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