US2916345A - Process for dyeing articles of polyeth- - Google Patents
Process for dyeing articles of polyeth- Download PDFInfo
- Publication number
- US2916345A US2916345A US2916345DA US2916345A US 2916345 A US2916345 A US 2916345A US 2916345D A US2916345D A US 2916345DA US 2916345 A US2916345 A US 2916345A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- carbonic acid
- polyeth
- articles
- disperse
- 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
- 238000004043 dyeing Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 18
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 18
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 16
- -1 POLYETHYLENE TEREPHTHALATE Polymers 0.000 claims description 16
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 12
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 10
- ROORDVPLFPIABK-UHFFFAOYSA-N Diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000003946 cyclohexylamines Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- HQZQYLGYCXEDHR-UHFFFAOYSA-M (2-methylphenyl) carbonate Chemical compound CC1=CC=CC=C1OC([O-])=O HQZQYLGYCXEDHR-UHFFFAOYSA-M 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 2
- 229940045714 Alkyl sulfonate alkylating agents Drugs 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N Methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- ABNXSTDXTPHERT-UHFFFAOYSA-N OC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)C1=CC=C(C=C1)C)N Chemical compound OC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)C1=CC=C(C=C1)C)N ABNXSTDXTPHERT-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000004651 carbonic acid esters Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TWBKZBJAVASNII-UHFFFAOYSA-N pentadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCS(O)(=O)=O TWBKZBJAVASNII-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
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
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl 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
- D06P1/0004—General aspects of dyeing
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
-
- 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
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl 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
- D06P1/653—Nitrogen-free carboxylic acids or their salts
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
-
- 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
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
Definitions
- the present invention relates to the dyeing of articles of polyesters or cellulose triacetate; more particularly it concerns a process for dyeing articles of polyesters or cellulose triacetate in an aqueous medium with disperse dyestuifs at boiling temperature. According to the invention this process is carried out in the presence of arylesters of carbonic acid.
- aryl esters of carbonic acid there are particularly suitable the phenyl esters such as diphenyl carbonate and their derivatives substituted in the benzene nucleus, e.g. by alkyl radicals or halogen atoms, such as o-tolyl carbonate, and the mixture of the various cresyl carbonates melting at about 55 C.
- aryl esters of carbonic acid are generally solid and water-insoluble, provision must be made so that they are present in the dyebath in the dispersed state.
- a solution of the carbonic acid esters in hot alcohol may be added to the dyebath containing a dispersing agent for the esters.
- Suitable dispersing agents are, for example, the sodium salt of dinaphthylmethane disulfonic acid as well as high molecular weight alkyl sulfates or alkyl sulfonates in the form of their water-soluble sodium or cyclohexylamine salts.
- aryl esters of carbonic acid required for carrying out the process of the present invention may readily be established by preliminary experiments in each case; quantities of l to grams per litre of the dyebath are generally sufiicient, depending on the desired depth of the dyeing. In general, the aryl esters of carbonic acid having a melting point below 100 C. are to be preferred.
- the process according to the invention enables filaments, fibres, foils and other articles of polyesters, for example those of the polyethylene terephthalate class, or of cellulose triacetate, to be dyed in very deep shades with a substantial acceleration of the dyestufi absorption.
- esters of aromatic carboxylic acids and aliphatic or aromatic alcohols such as benzoic Patented Dec. 8, 1959 "ice acid methyl ester, salicylic acid methyl ester or benzoic acid benzyl ester, which have previously been proposed as dyeing accelerators
- the aryl esters of carbonic acid exhibit a substantially greater activity. Moreover, they improve in most cases the light fastness of the dyeings.
- Example 1 Polyester fibres of polyethylene terephthalate are dyed at 98 C. in an aqueous bath having a liquor-to-goods ratio of 40:1 and containing per litre 0.75 gram of the disperse dyestulf 1-hydroxy-4-(p-tolyl)-amino-anthraquinone, 4 grams of diphenyl carbonate and 2 grams of the sodium salt of dinaphthylmethane disulfonic acid. The dyeing period is about 2 hours. A deep blue shade of very good light-fastness is thus obtained.
- Example 2 Fibres of cellulose triacetate are introduced at a liquor-to-goods ratio of 40:1 into a bath containing per litres 0.75 gram of the disperse dyestufi 1-amino-4-hydroxy-Z-bromo-anthraquinone, 5 grams of diphenyl carbonate and 1 gram of the cyclohexylamine salt of pentadecyl sulfonic acid. The dyeing is carried out in conventional manner at 96-98 C. for 2 hours yielding a deep red shade which is very fast to light.
- a process for dyeing articles made from a member of the group consisting of polyethylene terephthalate and cellulose triacetate which comprises contacting said articles in an aqueous medium at boiling temperature with disperse dyestuffs in the presence of dispersed aryl esters of carbonic acid.
- a process for dyeing an article made from polyethylene terephthalate which comprises contacting said article in an aqueous medium at boiling temperature with a disperse dyestuif in the presence of dispersed diphenyl carbonate.
- a process for dyeing an article made from cellulose triacetate which comprises contacting said article in an aqueous medium at boiling temperature with a disperse dyestuti in the presence of dispersed diphenyl carbonate.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
PROCESS FOR DYEING ARTICLES OF POLYETH- YLENE TEREPHTHALATE OR CELLULOSE TRI- ACETATE Walter Hees, Koln-Hohenberg, Germany, assignor to Farbenfabriken Bayer Aktiengesellschaft, Leverknsen, Germany, a corporation of Germany Application December 19, 1957 Serial No. 703,738
Claims priority, application Germany January 24, 1957 4 Claims. (Cl. 8-36) No Drawing.
The present invention relates to the dyeing of articles of polyesters or cellulose triacetate; more particularly it concerns a process for dyeing articles of polyesters or cellulose triacetate in an aqueous medium with disperse dyestuifs at boiling temperature. According to the invention this process is carried out in the presence of arylesters of carbonic acid.
As aryl esters of carbonic acid there are particularly suitable the phenyl esters such as diphenyl carbonate and their derivatives substituted in the benzene nucleus, e.g. by alkyl radicals or halogen atoms, such as o-tolyl carbonate, and the mixture of the various cresyl carbonates melting at about 55 C.
Since the aforesaid aryl esters of carbonic acid are generally solid and water-insoluble, provision must be made so that they are present in the dyebath in the dispersed state. For this purpose a solution of the carbonic acid esters in hot alcohol may be added to the dyebath containing a dispersing agent for the esters. Suitable dispersing agents are, for example, the sodium salt of dinaphthylmethane disulfonic acid as well as high molecular weight alkyl sulfates or alkyl sulfonates in the form of their water-soluble sodium or cyclohexylamine salts.
The quantities of aryl esters of carbonic acid required for carrying out the process of the present invention may readily be established by preliminary experiments in each case; quantities of l to grams per litre of the dyebath are generally sufiicient, depending on the desired depth of the dyeing. In general, the aryl esters of carbonic acid having a melting point below 100 C. are to be preferred.
The process according to the invention enables filaments, fibres, foils and other articles of polyesters, for example those of the polyethylene terephthalate class, or of cellulose triacetate, to be dyed in very deep shades with a substantial acceleration of the dyestufi absorption. Compared with the esters of aromatic carboxylic acids and aliphatic or aromatic alcohols such as benzoic Patented Dec. 8, 1959 "ice acid methyl ester, salicylic acid methyl ester or benzoic acid benzyl ester, which have previously been proposed as dyeing accelerators, the aryl esters of carbonic acid exhibit a substantially greater activity. Moreover, they improve in most cases the light fastness of the dyeings.
As disperse dyestuffs, there may be used the dyestuffs known under this designation (cf. for example Diserens, Die neuesten Fortschritte in der Anwendung der Farbstotle, vol. 2, second edition (1949), pages 254-259).
The following examples serve to illustrate the invention without, however, limiting the scope thereof.
Example 1 Polyester fibres of polyethylene terephthalate are dyed at 98 C. in an aqueous bath having a liquor-to-goods ratio of 40:1 and containing per litre 0.75 gram of the disperse dyestulf 1-hydroxy-4-(p-tolyl)-amino-anthraquinone, 4 grams of diphenyl carbonate and 2 grams of the sodium salt of dinaphthylmethane disulfonic acid. The dyeing period is about 2 hours. A deep blue shade of very good light-fastness is thus obtained.
Example 2 Fibres of cellulose triacetate are introduced at a liquor-to-goods ratio of 40:1 into a bath containing per litres 0.75 gram of the disperse dyestufi 1-amino-4-hydroxy-Z-bromo-anthraquinone, 5 grams of diphenyl carbonate and 1 gram of the cyclohexylamine salt of pentadecyl sulfonic acid. The dyeing is carried out in conventional manner at 96-98 C. for 2 hours yielding a deep red shade which is very fast to light.
I claim:
1. A process for dyeing articles made from a member of the group consisting of polyethylene terephthalate and cellulose triacetate which comprises contacting said articles in an aqueous medium at boiling temperature with disperse dyestuffs in the presence of dispersed aryl esters of carbonic acid.
2. A process according to claim 1 wherein diphenyl carbonate is applied as aryl ester of carbonic acid.
3. A process for dyeing an article made from polyethylene terephthalate which comprises contacting said article in an aqueous medium at boiling temperature with a disperse dyestuif in the presence of dispersed diphenyl carbonate.
4. A process for dyeing an article made from cellulose triacetate which comprises contacting said article in an aqueous medium at boiling temperature with a disperse dyestuti in the presence of dispersed diphenyl carbonate.
References Cited in the file of this patent Man Made Textiles for March 1956, pp. 72, 74.
Claims (1)
1. A PROCESS FOR DYEING ARTICLES MADE FROM A MEMBER OF THE GROUP CONSISTING OF POLYETHYLENE TEREPHTHALATE AND CELLULOSE TRIACETATE WHICH COMPRISES CONTACTING SAID AR TICLES IN AN AQUEOUS MEDIUM AT BOILING TEMPERATURE WITH DISPERSE DYESTUFFS IN TH PRESENCE OF DISPERSED ARYL ESTERS OF CARBONIC ACID.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2916345A true US2916345A (en) | 1959-12-08 |
Family
ID=3448903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2916345D Expired - Lifetime US2916345A (en) | Process for dyeing articles of polyeth- |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2916345A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098691A (en) * | 1961-02-17 | 1963-07-23 | Du Pont | Dyeing of polyester fiber |
| US3148934A (en) * | 1961-06-05 | 1964-09-15 | Dow Chemical Co | Process for dyeing polyester articles |
| US3256198A (en) * | 1963-04-22 | 1966-06-14 | Monsanto Co | Compositions containing an oxygen releasing compound and an organic carbonate |
| US3272750A (en) * | 1962-05-07 | 1966-09-13 | Lever Brothers Ltd | Process and composition containing an oxygen releasing compound and an organic carbonate |
-
0
- US US2916345D patent/US2916345A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3098691A (en) * | 1961-02-17 | 1963-07-23 | Du Pont | Dyeing of polyester fiber |
| US3148934A (en) * | 1961-06-05 | 1964-09-15 | Dow Chemical Co | Process for dyeing polyester articles |
| US3272750A (en) * | 1962-05-07 | 1966-09-13 | Lever Brothers Ltd | Process and composition containing an oxygen releasing compound and an organic carbonate |
| US3256198A (en) * | 1963-04-22 | 1966-06-14 | Monsanto Co | Compositions containing an oxygen releasing compound and an organic carbonate |
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