US2225589A - Process for the refining of textiles - Google Patents
Process for the refining of textiles Download PDFInfo
- Publication number
- US2225589A US2225589A US136636A US13663637A US2225589A US 2225589 A US2225589 A US 2225589A US 136636 A US136636 A US 136636A US 13663637 A US13663637 A US 13663637A US 2225589 A US2225589 A US 2225589A
- Authority
- US
- United States
- Prior art keywords
- water
- succinic acid
- radicle
- anhydride
- acid
- 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
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
Definitions
- This invention relates to the refining of tex: tiles.
- fibres of regenerated cellulose or cellulose esters I or cellulose ethers by incorporating into the textiles by chemical means the radicles of the water repelling fatty acids originally contained in the natural fibres, but which have been eliminated during the preliminary treatment thereof.
- the properties to be imparted to the textiles can likewise be attained by the incorporation of the radicles of dibasic carboxylic acids forming inner anhydrides and containing saturated or unsaturated open or cyclic carbon chains of at least 7 carbon atoms and especially of at least 9 carbon atoms.
- succinic acid and octadecenyl succinic acid are suitable for the purpose of this invention, the anhydrides of these acids being obtainable for example by condensing the corresponding olefines, such as isononylene, isododecylene, pentadecylene and octadecylene with maleic anhydride (compare French Patent No. 801,919).
- the radicles of succinic acids substituted in at least one methylene group by at least one aralkyl radicle such as 'ymethyl-'y-phenylpyrotartaric acid and -phenyl- 'y' -dimethylpyrotartaric acid, anhydrides of Suecinic acids of this type being obtainable for ex- Applicatlon April 13, 1937, Serial In Germany April 18, 1936 ample by the process of the co-pending application Ser. No.
- the chemical incorporation of the acid radicles into the textiles proceeds in the manner known per se, that is to say, the fibres are subjected to esterification by means of the said acid radicles under mild reaction conditions.
- esterification it suifices generally to treat the textiles, such as for example artificial fibres of regenerated cellulose or cotton materials at a temperature over about 30 C. and especially from about to about C. with a solution of an anhydride of the type of acid indicated in a suitable solvent which .is inert under the reaction conditions such as carbon tetrachloride, chloroform, acetone, esters of organic acids, for example ethyl acetate, butyl acetate etc.
- the degree of the hydrophobe action can be increased by subjecting the fibres treated in the manner described before after allowing the excess solution to drain oil to an after-heating over about C. and especially from about to about C.
- the salt formation can be carried out in the manner known per se, as for example, by the interaction of the acid groups with bases, such as especially bases of polyvalent metals, for example calcium hydroxide, zinc oxide, aluminium hydroxide, cerium oxide or with metal salts and especially salts of polyvalent metals of weak acids, such as calcium bicarbonate, aluminium formate, zinc acetate, furthermore for example in such a manner that there is first formed with the carboxyl group a water-sensitive salt, for ex Particularly good results are produced by saltformation with polyvalent metals, such as calcium, zinc, aluminium, cerium and lead.
- bases such as especially bases of polyvalent metals, for example calcium hydroxide, zinc oxide, aluminium hydroxide, cerium oxide or with metal salts and especially salts of polyvalent metals of weak acids, such as calcium bicarbonate, aluminium formate, zinc acetate, furthermore for example in such a manner that there is first formed with the carboxyl group a water-sensitive salt, for ex Particularly good results are produced by salt
- Example 1 Dyed cotton material is treated for a short time at a temperature of C. with a solution consisting of 5 gms. of the anhydride of dodecenyl succinic acid per litre of carbon tetrachloride and subjected for an hour at a temperature of 120 C. after vaporising the solvent. In this manner a very good waterproof effect is attained, which even withstands. boiling with soap and sodium carbonate for half an hour.
- Example 2- Cotton materials which are frequentlywashed. for example, materials for wind jackets, are dipped for a short time in a solution of 5 gins, oi the anhydride of isononenyl succinic acid per litre of benzin'e and squeezed out. After removing the solvent the goods are hung in a drying chamber at 120 C. for an hour. In this manner a fabric is obtained with very good water repellent propertieswhich are maintained after repeated washing by boiling.
- Emmple 3 Cotton fabric is treated for 15 minutes at C. with a 0.6% solution of isopentadecenyl succinic acid anhydride in carbon tetrachloride. The material is then beaten until air dry and rinsed with well water comprising 0.04% calcium bicarbonate per litre for 5 minutes at 80 0., dried over night and on the next day again rinsed for 5 minutes at 80 C. with the same well water.
- well water comprising 0.04% calcium bicarbonate per litre for 5 minutes at 80 0.
- the calcium bicarbonate present in the well water causes the formation of the calcium salt with the free carboxyl groups in'the fabric.
- the fabric when tested by the standard method, shows a water pressure number of 105 mm., whereas the water pressure number of the untreated fabric is, practically zero.
- Example 4 In the same manner as in Example 1 cotton fabric is treated with a 0.6% carbon tetrachloride solution of a substituted succinic acid anhydride obtained by condensation of triisopropyl benzene with maleic acid anhydride. The material is rinsed with well water as in Example 1 and dried.
- Example 5 An artificial silk fabric consisting of regenerated cellulose is treated with a 0.6% carbon tetrachloride solution of n-octadecenyl-succinic acid anhydride for about 15 minutes at 65 C.
- Example 6 The fabric is treatedwith n-octadecenyl succinic acid anhydride as in Example 5. After rinsing in dilute sodium carbonate solution, in- -10 stead ofthe treatment in a zinc chloride bath a treatment in an alum bath is carried out.
- g 1 Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one bydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated'in this manner 10 to an after-treatment with an agent forming a water-insoluble salt with the free carboxylic acid groups on the fibre.
- Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one bydrocarbon radicle of at least 9 carbonatoms, and
- Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated in this manner to an after-treatment with an aqueous solution of calcium bicarbonate.
- Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in 45 at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated in this manner to an after-treatment with an agent forming a water-sensitive salt with the free carboxylic acid groups on the fibre, and then converting this salt with a corresponding different salt into a waterinsoluble salt.
- Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms and subjecting the material treated in this manner to an after-treatment with an alkali carbonate solution, and then treating the alkali salt formed with a polyvalent metal salt solution.
- Material selected from the group consisting of water-repellent cotton and water-repellent artificial regenerated cellulose fibres which contain a radicle of succinic acid substituted in at least one methylene group by at least one hydro- 1 carbon radicle of at least 9 carbon atoms, one 75 carboxylic group of that acid being in the form of a water-insoluble salt radicle.
- a refined water-repellent cotton fabric containing the radicle of isopentadecenyl succinic acid, one carboxylic acid group of which is in the form of a calcium salt radicle.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
-succinic acids substituted Patented Dec. 17, 1940 UNITED STATES PATENT OFFICE PROCESS F OR THE REFINING OF TEXTILES the-Main, Germany No Drawing.
13 Claims.
This invention relates to the refining of tex: tiles.
It is already known to refine natural or artificial textiles, such as for example, cotton, wool,
fibres of regenerated cellulose or cellulose esters I or cellulose ethers by incorporating into the textiles by chemical means the radicles of the water repelling fatty acids originally contained in the natural fibres, but which have been eliminated during the preliminary treatment thereof.
In accordance with the present invention it, is now no longer necessary to be restrictedfor this purpose to the incorporation of fatty acid radicles and moreover, the properties to be imparted to the textiles can likewise be attained by the incorporation of the radicles of dibasic carboxylic acids forming inner anhydrides and containing saturated or unsaturated open or cyclic carbon chains of at least 7 carbon atoms and especially of at least 9 carbon atoms.
Among the acid radicles of the kind specified are particularly adapted for use in the present invention the radicles of succinic acids substituted in at least one methylene group by a hydrocarbon radicle of at least 7 carbon atoms for example by at least one saturated alkyl radi= cle of at least 7 carbon atoms and especially 9 carbon atoms, such as heptyl succinic acid, octyl succinic acid and especially isononyl succinic acid, isododecyl succinic acid and pentadecyl succinic acid, the anhydrides of these acids being obtainable for example in accordance with the co-pending application Ser. No. 733,126, filed June 29, 1934, by condensing saturated hydrocarbons, such as heptane, octane and especially isononane, isododecane and pentadecane with maleic anhydride. Furthermore the radicles of in at least one methylene group by at least one unsaturated alkyl radicle of at least 7 carbon atoms and especially 9 carbon atoms, such as isononenyl succinic acid, isododecenyl succinic acid, pentadecenyl,
succinic acid and octadecenyl succinic acid are suitable for the purpose of this invention, the anhydrides of these acids being obtainable for example by condensing the corresponding olefines, such as isononylene, isododecylene, pentadecylene and octadecylene with maleic anhydride (compare French Patent No. 801,919). Finally are to be mentioned the radicles of succinic acids substituted in at least one methylene group by at least one aralkyl radicle, such as 'ymethyl-'y-phenylpyrotartaric acid and -phenyl- 'y' -dimethylpyrotartaric acid, anhydrides of Suecinic acids of this type being obtainable for ex- Applicatlon April 13, 1937, Serial In Germany April 18, 1936 ample by the process of the co-pending application Ser. No. 733,126 by condensing aliphatic hydrocarbons substituted by an aromatic radicle, such as toluene, ethyl benzene, diethyl benzene, propyl benzene and isopropyl benzene, diisopropyl benzene, triisopropyl benzene, terahydronaphthalene etc. with maleic acid anhydride.
The chemical incorporation of the acid radicles into the textiles proceeds in the manner known per se, that is to say, the fibres are subjected to esterification by means of the said acid radicles under mild reaction conditions. For attaining esterification it suifices generally to treat the textiles, such as for example artificial fibres of regenerated cellulose or cotton materials at a temperature over about 30 C. and especially from about to about C. with a solution of an anhydride of the type of acid indicated in a suitable solvent which .is inert under the reaction conditions such as carbon tetrachloride, chloroform, acetone, esters of organic acids, for example ethyl acetate, butyl acetate etc. I
The degree of the hydrophobe action can be increased by subjecting the fibres treated in the manner described before after allowing the excess solution to drain oil to an after-heating over about C. and especially from about to about C.
Furthermore it has been found that by the esterification of the fibres at a temperature up to about 70 C. in the manner described above only one carboxyl group of the dibasic carboxylic acids is esterified with the textile fibre while the other carboxyl group remains free and that even at the after-treatment at a temperature up to about 130 C. still part of the carboxyl acid groups remain in a free condition. It has now been found that the hydrophobe qualities of the textile materials treated in the manner described before can be improved considerably by subjecting them to an after-treatment with a salt forming agent whereby the free carboxyl groups are combined with a base which is so selected that the capacity for taking up water is still further reduced.
The salt formation can be carried out in the manner known per se, as for example, by the interaction of the acid groups with bases, such as especially bases of polyvalent metals, for example calcium hydroxide, zinc oxide, aluminium hydroxide, cerium oxide or with metal salts and especially salts of polyvalent metals of weak acids, such as calcium bicarbonate, aluminium formate, zinc acetate, furthermore for example in such a manner that there is first formed with the carboxyl group a water-sensitive salt, for ex Particularly good results are produced by saltformation with polyvalent metals, such as calcium, zinc, aluminium, cerium and lead.
The following examples will illustrate the invention without being restricted thereto:
Example 1 Dyed cotton material is treated for a short time at a temperature of C. with a solution consisting of 5 gms. of the anhydride of dodecenyl succinic acid per litre of carbon tetrachloride and subjected for an hour at a temperature of 120 C. after vaporising the solvent. In this manner a very good waterproof effect is attained, which even withstands. boiling with soap and sodium carbonate for half an hour.
Example 2- Cotton materials which are frequentlywashed. for example, materials for wind jackets, are dipped for a short time in a solution of 5 gins, oi the anhydride of isononenyl succinic acid per litre of benzin'e and squeezed out. After removing the solvent the goods are hung in a drying chamber at 120 C. for an hour. In this manner a fabric is obtained with very good water repellent propertieswhich are maintained after repeated washing by boiling.
Emmple 3 Cotton fabric is treated for 15 minutes at C. with a 0.6% solution of isopentadecenyl succinic acid anhydride in carbon tetrachloride. The material is then beaten until air dry and rinsed with well water comprising 0.04% calcium bicarbonate per litre for 5 minutes at 80 0., dried over night and on the next day again rinsed for 5 minutes at 80 C. with the same well water. By this means the calcium bicarbonate present in the well water causes the formation of the calcium salt with the free carboxyl groups in'the fabric.
After drying, the fabric, when tested by the standard method, shows a water pressure number of 105 mm., whereas the water pressure number of the untreated fabric is, practically zero.
Example 4 In the same manner as in Example 1 cotton fabric is treated with a 0.6% carbon tetrachloride solution of a substituted succinic acid anhydride obtained by condensation of triisopropyl benzene with maleic acid anhydride. The material is rinsed with well water as in Example 1 and dried.
Example 5 An artificial silk fabric consisting of regenerated cellulose is treated with a 0.6% carbon tetrachloride solution of n-octadecenyl-succinic acid anhydride for about 15 minutes at 65 C.
and after heating air dry, treated for 5 minutes with a dilute aqueous 3% sodium carbonate solution at C. The material is then introduced for 5 minutes into an aqueous zinc chloride sosublecting the material treated in this manner to assaesa lution heated to80 C. After squeezing out and drying there is obtained on sprinkling the material with water a moisture absorption of 36%. whereas the untreated fabric tested in a similar manner takes up of moisture.
Example 6 The fabric is treatedwith n-octadecenyl succinic acid anhydride as in Example 5. After rinsing in dilute sodium carbonate solution, in- -10 stead ofthe treatment in a zinc chloride bath a treatment in an alum bath is carried out.
We claim:
g 1. Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one bydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated'in this manner 10 to an after-treatment with an agent forming a water-insoluble salt with the free carboxylic acid groups on the fibre.
2. Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one bydrocarbon radicle of at least 9 carbonatoms, and
an after-treatment with an aqueous solution of a weak acid salt of a polyvalent metal.
3. Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated in this manner to an after-treatment with an aqueous solution of calcium bicarbonate.
4. Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in 45 at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms, and subjecting the material treated in this manner to an after-treatment with an agent forming a water-sensitive salt with the free carboxylic acid groups on the fibre, and then converting this salt with a corresponding different salt into a waterinsoluble salt.
5. Process which comprises esterifying material selected from the group consisting of cotton and artificial regenerated cellulose fibres with an inner anhydride of a succinic acid substituted in at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms and subjecting the material treated in this manner to an after-treatment with an alkali carbonate solution, and then treating the alkali salt formed with a polyvalent metal salt solution.
,6. Refined water-repellent textiles which con tain the radicle of a dibasic carboxylic acid capable of forming an inner anhydride and having a carbon chain of at least 7 carbon atoms, one car boxylic acid group of which is in the form of a water-insoluble salt radicle.
7. Material selected from the group consisting of water-repellent cotton and water-repellent artificial regenerated cellulose fibres which contain a radicle of succinic acid substituted in at least one methylene group by at least one hydro- 1 carbon radicle of at least 9 carbon atoms, one 75 carboxylic group of that acid being in the form of a water-insoluble salt radicle.
8. Material selected from the group consisting of water-repellent cotton and water-repellent artificial regenerated cellulose fibres, which contain a radicle of succinic acid substituted in at least one methylene group by at least one hydrocarbon radicle of at least 9 carbon atoms, one carboxylic group of that acid being in the form of a calcium salt radicle.
9. A refined water-repellent cotton fabric containing the radicle of isopentadecenyl succinic acid, one carboxylic acid group of which is in the form of a calcium salt radicle.
10:A' refined water-repellent regenerated cellulosic fabric, which contains the radicle of noctadecenyl succinic acid, one carboxylic acid group of which is in the form of a zinc salt radicle.
11. The process which comprises chemically reacting cotton fabrics at 65 C. with a solution 01' 12. The process which comprises chemically reacting regenerated cellulose fabrics at a temperature of 65 C. with a solution of n-octadecenyl succinic acid anhydride in carbon tetrachloride,
- for a suflicient period of time and concentration 5 of anhydride to render the fabrics water-repellent, drying the fabrics, then treating the fabrics with an aqueous sodium carbonate. solution at a temperature of 80 C. and then with an aqueous zinc chloride solution at the same temperature, 10 to thereby increasethe water-repellency of the treated fabrics.
13. The process which comprises chemically reacting a textile with an inner'anhydride of a dibasic carboxylic acid having a carbon chain of at 15 least 7 carbon atoms at a concentration of anhydride, temperature and for a period of time sumcient to render the fabrics water-repellent, subjecting thetextile treated in this manner to an aftertreatment with an agent forming a go water-insoluble salt with the free carboxylic acid groups on the fiber to increase the water repellency of the fabrics.
HANS HAUSSMANN. 25 OSWAL'D MEISSNER. WALTER PINKERNELLE. HELMUT ZINKE.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2225589X | 1936-04-18 | ||
GB21617/36A GB479753A (en) | 1936-04-18 | 1936-08-05 | Process for refining textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
US2225589A true US2225589A (en) | 1940-12-17 |
Family
ID=32070949
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US136636A Expired - Lifetime US2225589A (en) | 1936-04-18 | 1937-04-13 | Process for the refining of textiles |
Country Status (3)
Country | Link |
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US (1) | US2225589A (en) |
FR (1) | FR820562A (en) |
GB (1) | GB479753A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2448153A (en) * | 1946-09-10 | 1948-08-31 | Us Agriculture | Process of making cotton textiles water-absorbent and rotresistant |
US2486720A (en) * | 1945-12-22 | 1949-11-01 | Callaway Mills Co | Adhesion of rubber to fibrous materials |
US2550697A (en) * | 1946-05-08 | 1951-05-01 | Bancroft & Sons Co J | Cloth water bag |
US2613206A (en) * | 1949-12-14 | 1952-10-07 | Nat Starch Products Inc | Free-flowing starch esters |
US2661349A (en) * | 1949-02-18 | 1953-12-01 | Nat Starch Products Inc | Polysaccharide derivatives of substituted dicarboxylic acids |
US2980491A (en) * | 1955-06-15 | 1961-04-18 | Segal Leon | Textile fibers comprising perfluoroalkanoyl esters of cellulose and process of making the same |
US3097051A (en) * | 1958-11-18 | 1963-07-09 | Ricardo H Wade | Cellulose ester anhydrides in fiber form |
GB2469181A (en) * | 2009-03-31 | 2010-10-06 | Acetylated Fibres Ltd | Treatment of a natural cellulosic fibre with an anhydride |
-
1936
- 1936-08-05 GB GB21617/36A patent/GB479753A/en not_active Expired
-
1937
- 1937-04-13 US US136636A patent/US2225589A/en not_active Expired - Lifetime
- 1937-04-13 FR FR820562D patent/FR820562A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2486720A (en) * | 1945-12-22 | 1949-11-01 | Callaway Mills Co | Adhesion of rubber to fibrous materials |
US2550697A (en) * | 1946-05-08 | 1951-05-01 | Bancroft & Sons Co J | Cloth water bag |
US2448153A (en) * | 1946-09-10 | 1948-08-31 | Us Agriculture | Process of making cotton textiles water-absorbent and rotresistant |
US2661349A (en) * | 1949-02-18 | 1953-12-01 | Nat Starch Products Inc | Polysaccharide derivatives of substituted dicarboxylic acids |
US2613206A (en) * | 1949-12-14 | 1952-10-07 | Nat Starch Products Inc | Free-flowing starch esters |
US2980491A (en) * | 1955-06-15 | 1961-04-18 | Segal Leon | Textile fibers comprising perfluoroalkanoyl esters of cellulose and process of making the same |
US3097051A (en) * | 1958-11-18 | 1963-07-09 | Ricardo H Wade | Cellulose ester anhydrides in fiber form |
GB2469181A (en) * | 2009-03-31 | 2010-10-06 | Acetylated Fibres Ltd | Treatment of a natural cellulosic fibre with an anhydride |
Also Published As
Publication number | Publication date |
---|---|
GB479753A (en) | 1938-02-07 |
FR820562A (en) | 1937-11-15 |
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