US2803607A - Nu-substituted polyacrylamide sizing material composition and method - Google Patents
Nu-substituted polyacrylamide sizing material composition and method Download PDFInfo
- Publication number
- US2803607A US2803607A US357907A US35790753A US2803607A US 2803607 A US2803607 A US 2803607A US 357907 A US357907 A US 357907A US 35790753 A US35790753 A US 35790753A US 2803607 A US2803607 A US 2803607A
- Authority
- US
- United States
- Prior art keywords
- sizing
- sizing material
- substituted
- yarns
- alkylene
- 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
- 239000000203 mixture Substances 0.000 title claims description 4
- 238000004513 sizing Methods 0.000 title description 20
- 239000000463 material Substances 0.000 title description 8
- 238000000034 method Methods 0.000 title description 7
- 229920002401 polyacrylamide Polymers 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 239000003292 glue Substances 0.000 claims description 5
- 229920001353 Dextrin Polymers 0.000 claims description 4
- 239000004375 Dextrin Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 229920003086 cellulose ether Polymers 0.000 claims description 4
- 235000019425 dextrin Nutrition 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 description 9
- 229920002994 synthetic fiber Polymers 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 241000360590 Erythrites Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/05—Cellulose or derivatives thereof
- D06M15/09—Cellulose ethers
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/11—Starch or derivatives thereof
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
- D06M15/29—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing a N-methylol group or an etherified N-methylol group; containing a N-aminomethylene group; containing a N-sulfidomethylene group
Definitions
- the present invention relates to new sizing material and to a process of sizing yarns of artificial fibers, particularly synthetic fibers.
- yarns of artificial fibers are sized by treating them with aqueous solutions of polymerization products of amides of unsaturated fatty acids of low molecular weight, which polymerization products have been rendered water soluble by the action of alkylene oxides or their functional derivatives.
- Suitable polymerization products of amides of unsaturated fatty acids of low molecular weight are particularly the polyacrylamides and their N-substituted derivatives, which carry at least one member selected from the group consisting of hydrogen and hydroxy alkyl attached to the nitrogen atom.
- the amides are rendered water soluble by the reaction with alkylene oxides, especially ethylene oxide or its functional derivatives, such as halohydrins or a,a-halogeno-hydroxyether, for instance as described in U. S. application Ser. No. 337,218, filed February 16, 1953, which will be assigned to the same assignee.
- the fibrous material to be treated 'with the sizing material of the present invention may consist, for instance, of polymerizates, polyesters, polyamides, polyaddition prod ucts or of cellulose acetate.
- the necessary amounts of the sizing material and the suitable concentrations of the aqueous solutions to be applied may easily be found out by preliminary tests.
- the sizing material of the present invention may be applied in relatively dilute aqueous solutions.
- the invention thus obviates the troublesome sticking of the fibers during the sizing procedure. Furthermore the danger of an electrostatic charge no longer exists. This constitutes a considerable advantage over the sizing agents prepared from polyvinyl alcohol or acrylic acid esters which may give rise to charges up to 10,000 volts.
- the sizing material may also be used in combination with water soluble waxlike substances, which are obtainable, for instance, by the reaction of polyvalent alcohols, such as hexanetriol, trimethylol propane, or penta-v erythrite, with alkylene oxides, preferably ethylene oxide.
- polyvalent alcohols such as hexanetriol, trimethylol propane, or penta-v erythrite
- Example 1 An aqueous solution containing per liter grams of the water soluble product obtained from ethylene oxide and polyacrylamide in the molecular ratio of 16 to 1 according to Example 1 of U. S. application Ser. No. 337,218, is used to size a caprolactam warp having a setting of 50 threads of the metrical number 225 per centimeter, on a sizing machine. After drying at about 80-100" C. a yarn of very good closeness is obtained. The electrostatic charge of the warp, if occurring at all during the sizing operation, is negligible.
- Example 2 An aqueous solution containing per liter 80 grams of the water soluble product obtainedfrom ethylene oxide and polyacrylamide in the molecular ratio of 16 to 1 according to Example 1 of U. S. application Ser. No. 337,- 218, and in addition thereto 20 grams of animal glue and 5 grams of the reaction product of 1550 parts by weight of ethylene oxide and 50 parts by weight of trimethylol propane is used to size a warp consisting of polyacrylonitrile yarns having a setting of 45 threads of the metrical number per centimeter. After drying at 80 C. a yarn of very good closeness is obtained.
- a sizing composition for artificial fibers containing (a) a water soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula R(--OR)-nOH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxide and n is an integer of at least 1 and (b) at least one member of the group consisting of starch, dextrin, glue, sugar, salts of cellulose ether carboxylic acids and wax-like substances obtained by the action of ethylene oxide on polyvalent alcohols.
- a process of sizing yarns of artificial fibers which comprises treating said yarns with an aqueous solution of a water-soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula --R-(OR)--nOH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxide and rt is an integer of at least 1.
- a process of sizing yarns of artificial fibers which comprises treating said yarns with an aqueous solution of a water-soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula --R--(-OR-)1.OH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxidc and n is an integer of at least 1 and at least one member of the group consisting of starch, dextrin, glue, sugar, salts of cellulose ether carboxylic acids and wax-like substances obtained by the action of ethylene oxide on polyvalent alcohols.
- a process of sizing yarns of polycaprolactam fibers which comprises treating said yarns with an aqueous solution" of a water-soluble N-substituted honiopolyarcrylamide; wherein said N-substituents"are-thoseof the-forresidue of an alpha, beta-alkylene epoxide and n is an integer of at least 1.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
United States Patent N-SUBSTITUTED POLYACRYLAMIDE SIZING MA- TERIAL COMPOSITION AND METHOD No Drawing. Application May 27, 1953, Serial No. 357,907
Claims priority, application Germany May 29, 1952 5 Claims. (Cl. 260-8) The present invention relates to new sizing material and to a process of sizing yarns of artificial fibers, particularly synthetic fibers.
In accordance with the invention yarns of artificial fibers, especially synthetic fibers are sized by treating them with aqueous solutions of polymerization products of amides of unsaturated fatty acids of low molecular weight, which polymerization products have been rendered water soluble by the action of alkylene oxides or their functional derivatives.
Suitable polymerization products of amides of unsaturated fatty acids of low molecular weight, which have been rendered water soluble as aforesaid, are particularly the polyacrylamides and their N-substituted derivatives, which carry at least one member selected from the group consisting of hydrogen and hydroxy alkyl attached to the nitrogen atom. The amides are rendered water soluble by the reaction with alkylene oxides, especially ethylene oxide or its functional derivatives, such as halohydrins or a,a-halogeno-hydroxyether, for instance as described in U. S. application Ser. No. 337,218, filed February 16, 1953, which will be assigned to the same assignee. The fibrous material to be treated 'with the sizing material of the present invention may consist, for instance, of polymerizates, polyesters, polyamides, polyaddition prod ucts or of cellulose acetate.
The necessary amounts of the sizing material and the suitable concentrations of the aqueous solutions to be applied may easily be found out by preliminary tests.
Whereas the sizing materials heretofore used for artificial fibers, particularly for synthetic fibers, have to be applied in comparatively concentrated aqueous solutions, the sizing material of the present invention may be applied in relatively dilute aqueous solutions. The invention thus obviates the troublesome sticking of the fibers during the sizing procedure. Furthermore the danger of an electrostatic charge no longer exists. This constitutes a considerable advantage over the sizing agents prepared from polyvinyl alcohol or acrylic acid esters which may give rise to charges up to 10,000 volts. It is further within the scope of the present invention to increase the activity of the new sizing material by the addition of small amounts of water soluble film forming substances, such as starch, dextrin, glue, sugar or salts of cellulose ether carboxylic acids. These substances simultaneously enhance the stiffness of the sized yarns.
The sizing material may also be used in combination with water soluble waxlike substances, which are obtainable, for instance, by the reaction of polyvalent alcohols, such as hexanetriol, trimethylol propane, or penta-v erythrite, with alkylene oxides, preferably ethylene oxide.
These substances give rise to an excellent smoothness of the sized yarns and help to eliminate the danger of an electrostatic charge of the yarns during sizing and spinning.
The following examples serve to illustrate the present invention without, however, limiting the scope thereof.
Example 1 An aqueous solution containing per liter grams of the water soluble product obtained from ethylene oxide and polyacrylamide in the molecular ratio of 16 to 1 according to Example 1 of U. S. application Ser. No. 337,218, is used to size a caprolactam warp having a setting of 50 threads of the metrical number 225 per centimeter, on a sizing machine. After drying at about 80-100" C. a yarn of very good closeness is obtained. The electrostatic charge of the warp, if occurring at all during the sizing operation, is negligible.
Example 2 An aqueous solution containing per liter 80 grams of the water soluble product obtainedfrom ethylene oxide and polyacrylamide in the molecular ratio of 16 to 1 according to Example 1 of U. S. application Ser. No. 337,- 218, and in addition thereto 20 grams of animal glue and 5 grams of the reaction product of 1550 parts by weight of ethylene oxide and 50 parts by weight of trimethylol propane is used to size a warp consisting of polyacrylonitrile yarns having a setting of 45 threads of the metrical number per centimeter. After drying at 80 C. a yarn of very good closeness is obtained.
The electrostatic charge of the warp, if occurring at all during the sizing operation, is negligible.
We claim:
1. A sizing composition for artificial fibers containing (a) a water soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula R(--OR)-nOH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxide and n is an integer of at least 1 and (b) at least one member of the group consisting of starch, dextrin, glue, sugar, salts of cellulose ether carboxylic acids and wax-like substances obtained by the action of ethylene oxide on polyvalent alcohols.
2. A process of sizing yarns of artificial fibers which comprises treating said yarns with an aqueous solution of a water-soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula --R-(OR)--nOH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxide and rt is an integer of at least 1. r
3. A process of sizing yarns of artificial fibers which comprises treating said yarns with an aqueous solution of a water-soluble N-substituted homopolyacrylamide, wherein said N-substituents are those of the formula --R--(-OR-)1.OH, wherein R is the alkylene residue of an alpha, beta-alkylene epoxidc and n is an integer of at least 1 and at least one member of the group consisting of starch, dextrin, glue, sugar, salts of cellulose ether carboxylic acids and wax-like substances obtained by the action of ethylene oxide on polyvalent alcohols.
4. A process of sizing yarns of polycaprolactam fibers which comprises treating said yarns with an aqueous solution" of a water-soluble N-substituted honiopolyarcrylamide; wherein said N-substituents"are-thoseof the-forresidue of an alpha, beta-alkylene epoxide and n is an integer of at least 1.
, 4. References Cited in the file of this patent UNITED STATES PATENTS 1,976,679 Fikentscher et a1 Oct. 9, 1934 2,470,081 Thurston et a1. May 10, 1949 2,593,888 Jones Apr. 22, 1952 FOREIGN PATENTS 111,911 Sweden i; Oct. 13, 1942 OTHER REFERENCES Mitchell et a1.: Organic Analysis, vol. I, pp. 127 and 128,, Interscience, 1953.
Claims (1)
1. A SIZING COMPOSITION FOR ARTIFICIAL FIBERS CONTAINING (A) A WATER SOLUBLE N-SUBSTITUTED HOMOPOLYACRYLAMIDE, WHEREIN SAID N-SUBSTITUENTS ARE THOSE OF THE FORMULA -R-(-OR-)-NOH, WHEREIN R IS THE ALKYLENE RESIDUE OF AN ALPHA, BETA-ALKYLENE EPOXIDE AND N IS AN INTEGER OF AT LEAST 1 AND (B) AT LEAST ONE MEMBER OF THE GROUP CONSISTING OF STARCH, DEXTRIN, GLUE, SUGAR, SALT OF CELLULOSE ETHER CARBOXYLIC ACIDS AND WAX-LIKE SUBSTANCES OBTAINED BY THE ACTION OF ETHYLENE OXIDE ON POLYVALENT ALCOHOLS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE739201X | 1952-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2803607A true US2803607A (en) | 1957-08-20 |
Family
ID=6642986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US357907A Expired - Lifetime US2803607A (en) | 1952-05-29 | 1953-05-27 | Nu-substituted polyacrylamide sizing material composition and method |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2803607A (en) |
| GB (1) | GB739201A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875100A (en) * | 1957-10-16 | 1959-02-24 | Dow Chemical Co | Finish for cellulosic textile materials |
| US2875099A (en) * | 1957-10-16 | 1959-02-24 | Dow Chemical Co | Finish for polyester textile materials |
| US3016333A (en) * | 1958-10-31 | 1962-01-09 | American Cyanamid Co | Method of treating hair with hydroxyether amides of polyacrylic acids |
| US3051588A (en) * | 1959-04-10 | 1962-08-28 | Johnson & Johnson | Product and method of manufacture |
| US3284232A (en) * | 1961-04-21 | 1966-11-08 | Eastman Kodak Co | Shaped objects of a crystalline polyester coated with a hydrophilic polymer composition |
| US3309222A (en) * | 1963-12-09 | 1967-03-14 | Eastman Kodak Co | Polyesters or polycarbonates coated with cured unsaturated polyester resins containing nitrogen |
| EP0208426A3 (en) * | 1985-06-28 | 1987-05-20 | Springs Industries Inc. | Method of durably sizing textile yarns, sizing composition and durably sized yarns produced therefrom |
| US5445655A (en) * | 1993-03-02 | 1995-08-29 | Ciba-Geigy Corporation | Auxiliary for textile wet finishing processes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1188032B (en) * | 1961-04-27 | 1965-03-04 | Bayer Ag | Process for appearing synthetic organic fiber material |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1976679A (en) * | 1930-05-26 | 1934-10-09 | Ig Farbenindustrie Ag | Production of dispersions |
| US2470081A (en) * | 1946-06-18 | 1949-05-10 | American Cyanamid Co | Alkylene oxide condensation products of dimerized fatty acid alylol amides |
| US2593888A (en) * | 1945-10-16 | 1952-04-22 | Gen Aniline & Film Corp | Production of hydroxyalkyl amides of acrylic acids |
-
1953
- 1953-05-27 US US357907A patent/US2803607A/en not_active Expired - Lifetime
- 1953-05-28 GB GB14931/53A patent/GB739201A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1976679A (en) * | 1930-05-26 | 1934-10-09 | Ig Farbenindustrie Ag | Production of dispersions |
| US2593888A (en) * | 1945-10-16 | 1952-04-22 | Gen Aniline & Film Corp | Production of hydroxyalkyl amides of acrylic acids |
| US2470081A (en) * | 1946-06-18 | 1949-05-10 | American Cyanamid Co | Alkylene oxide condensation products of dimerized fatty acid alylol amides |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875100A (en) * | 1957-10-16 | 1959-02-24 | Dow Chemical Co | Finish for cellulosic textile materials |
| US2875099A (en) * | 1957-10-16 | 1959-02-24 | Dow Chemical Co | Finish for polyester textile materials |
| US3016333A (en) * | 1958-10-31 | 1962-01-09 | American Cyanamid Co | Method of treating hair with hydroxyether amides of polyacrylic acids |
| US3051588A (en) * | 1959-04-10 | 1962-08-28 | Johnson & Johnson | Product and method of manufacture |
| US3284232A (en) * | 1961-04-21 | 1966-11-08 | Eastman Kodak Co | Shaped objects of a crystalline polyester coated with a hydrophilic polymer composition |
| US3309222A (en) * | 1963-12-09 | 1967-03-14 | Eastman Kodak Co | Polyesters or polycarbonates coated with cured unsaturated polyester resins containing nitrogen |
| EP0208426A3 (en) * | 1985-06-28 | 1987-05-20 | Springs Industries Inc. | Method of durably sizing textile yarns, sizing composition and durably sized yarns produced therefrom |
| US4756714A (en) * | 1985-06-28 | 1988-07-12 | Springs Industries, Inc. | Method of durably sizing textile yarns, durable sizing composition, and durably sized yarns and fabrics produced therefrom |
| US5445655A (en) * | 1993-03-02 | 1995-08-29 | Ciba-Geigy Corporation | Auxiliary for textile wet finishing processes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB739201A (en) | 1955-10-26 |
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