GB1007820A - Improvements in and relating to sulfophenoxyalkoxy-aromatic dicarboxylic acids, salts and esters and dyeable polyesters - Google Patents
Improvements in and relating to sulfophenoxyalkoxy-aromatic dicarboxylic acids, salts and esters and dyeable polyestersInfo
- Publication number
- GB1007820A GB1007820A GB4093062A GB4093062A GB1007820A GB 1007820 A GB1007820 A GB 1007820A GB 4093062 A GB4093062 A GB 4093062A GB 4093062 A GB4093062 A GB 4093062A GB 1007820 A GB1007820 A GB 1007820A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- phenoxy
- acid
- terephthalate
- ester
- 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
Links
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
-
- 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
- D06P3/36—Material containing ester groups using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a dyeable linear polyester which is a condensation product of an aromatic dicarboxylic acid or dialkyl ester thereof with a diol, such as an acrclic or alicyclic aliphatic glycol, an aromatic diol, an aliphatic-aromatic diol, or a diester thereof, and from 0.1 to 10 mole per cent, based on the total amount of dicarboxylic acid compounds present, of a sulphonated compound of the formula <FORM:1007820/C3/1> wherein M designates an alkali metal atom, n is an integer from 1 to 12, Ar is an arenyl radical, and R is a hydrogen atom or an alkyl radical having 1 to 8 carbon atoms. Linear polyesters may also be made from a hydrocarboxylic acid or ester thereof with a sulphonated compound as above, or by the partial replacement of a diol or aromatic dicarboxylic acid or ester with a hydroxycarboxylic acid or ester in the above polyesters. A monofunctional aromatic acid or ester can also be added as a molecular weight regulator. Illustrative of molecular weight regulators which can also serve as dye-assistants are compounds of the formula <FORM:1007820/C3/2> according to Specification No. 40928/62. In Examples (3) to (8) describe the preparation of polyesters from dimethyl terephthalate, ethylene glycol and dimethyl 5-(2-[4-(sodiumsulpho) phenoxy]ethoxy)-isophthalate; (9) includes also methyl (2 - [sodiumsulpho]phenoxy) acetate ; (10) includes methyl benzoate; (11) uses dimethyl 2-(5-[4-potassiumsulpho-phenoxy]-pentoxy) terephthalate; (12) is as in (11) but includes methyl 6-(4-[sodiumsulpho[phenoxy) hexanoate; and (13) describes a polyester from dimethyl terephthalate, dimethyl isophthalate, dimethyl 2-(5-[4-lithiumsulpho-phenoxy]pentoxy) terephthalate and 1,4 - cyclohexanedimethanol. Polyesterification is effected in the presence of the usual catalysts and, possibly, titanium dioxide. The polyesters may be melt-spun to form filaments and yarns which can be woven into fabrics and dyed by conventional techniques.ALSO:The invention comprises compounds of the formula <FORM:1007820/C2/1> in which X is an -SO3H or -SO3M radical, wherein M is an alkali metal, n is an integer from 1 to 12, Ar is an arenyl radical, i.e. a trivalent aromatic hydrocarbon radical, such as a phenenyl or naphthenyl radical, and R is a hydrogen atom or an alkyl radical having 1 to 8 carbon atoms. The novel compounds may be made by reacting a phenoxyalkoxyphthalic acid or ester of the formula above where X is hydrogen, and Ar, n and R are as above, with a sulphonating agent comprised of a mixture of sulphuric acid and acetic anhydride, at a temperature of from -15 DEG to 50 DEG C. The acid or ester is preferably introduced into the sulphonating agent in solution in an inert solvent, such as methylene dichloride, ethylene dichloride or ethyl acetate. The sulphonated phenoxy alkoxyphthalic acid or ester can be reacted with an alkali metal hydroxide or lakoxide or an alkali metal salt of an acid weaker than sulphonic acid, such as acetic or benzoic, to form the corresponding alkali metal sulphonate. The phenoxyalkoxyphthalic acids and esters, used as starting materials, may be obtained by the reaction of a phenoxyalkyl halide with an alkali metal dicarboxy or dicarbalkoxy phenolate, in a solvent such as ethanol, N,N-dimethylformamide or dioxane at a temperature of from 20 DEG to 100 DEG C. Examples describe the preparation of (1) dimethyl 5 - (2 - phenoxy - ethoxy) isophthalate, its sulphonation to dimethyl 5-(2-[4-sulphophenoxy] ethoxy) isophthalate and sodium salt formation; dibutyl 5-(2-[4-potassiumsulpho) phenoxy] ethoxy) isophthalate; (2) dimethyl 2 - (5 - phenoxypentoxy) - terephthalate, its sulphonation to dimethyl 2-(5-[4-sulphophenoxy] pentoxy) terephthalate and its conversion to dimethyl 2-(5-[4-(potassiumsulpho) phenoxy] pentoxy) terephthalate and the corresponding lithium salt; diethyl 2-(8-[4-(sodiumsulpho) phenoxy] octoxy) terephthalate.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US149206A US3077492A (en) | 1961-11-01 | 1961-11-01 | (sulfophenoxy)alkoxy-substituted aromatic dicarboxylic acids and derivatives thereof |
US149205A US3164566A (en) | 1961-11-01 | 1961-11-01 | Dyeable linear polyesters modified by a metallosulfophenoxyalkoxy-substituted aromatic dicarboxylic acid or ester |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1007820A true GB1007820A (en) | 1965-10-22 |
Family
ID=26846547
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4093062A Expired GB1007820A (en) | 1961-11-01 | 1962-10-30 | Improvements in and relating to sulfophenoxyalkoxy-aromatic dicarboxylic acids, salts and esters and dyeable polyesters |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE663865A (en) |
DE (1) | DE1545091A1 (en) |
GB (1) | GB1007820A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0056172A2 (en) * | 1981-01-09 | 1982-07-21 | FISONS plc | Phenoxy- and thiophenoxy compounds, methods for their preparation and pharmaceutical formulations containing them |
-
1962
- 1962-10-30 DE DE19621545091 patent/DE1545091A1/en active Pending
- 1962-10-30 GB GB4093062A patent/GB1007820A/en not_active Expired
-
1965
- 1965-05-13 BE BE663865D patent/BE663865A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0056172A2 (en) * | 1981-01-09 | 1982-07-21 | FISONS plc | Phenoxy- and thiophenoxy compounds, methods for their preparation and pharmaceutical formulations containing them |
EP0056172A3 (en) * | 1981-01-09 | 1982-09-29 | Fisons Plc | Phenoxy- and thiophenoxy compounds, methods for their preparation and pharmaceutical formulations containing them |
Also Published As
Publication number | Publication date |
---|---|
BE663865A (en) | 1965-09-01 |
DE1545091A1 (en) | 1970-01-02 |
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