US2746880A - Adhesive cotton article and method of making same - Google Patents

Adhesive cotton article and method of making same Download PDF

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US2746880A
US2746880A US310904A US31090452A US2746880A US 2746880 A US2746880 A US 2746880A US 310904 A US310904 A US 310904A US 31090452 A US31090452 A US 31090452A US 2746880 A US2746880 A US 2746880A
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yarn
dextran
cotton
ether
adhesive
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US310904A
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George L Deniston
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Commonwealth Engineering Company of Ohio
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating 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
    • D06M15/03Polysaccharides or derivatives thereof
    • D06M15/11Starch or derivatives thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06BTREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B17/00Storing of textile materials in association with the treatment of the materials by liquids, gases or vapours
    • D06B17/005Storing of textile materials in association with the treatment of the materials by liquids, gases or vapours in helical form
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2971Impregnation

Definitions

  • Dextran is a water soluble colloidal material produced by the action of microorganisms on sucrose bearing materials and may be converted into dextran ethers and esters as described in U, S. Patents 2,344,179, 2,203,702 and 2,385,553.
  • This invention contemplates the provision of a novel process for the impregnation and coating of cotton materials with dextran and its derivatives.
  • the invention contemplates the provision of a new product wherein cotton provides a strength core and material impregnated therein and coated thereon provides an outer shell resistant to ordinary chemical attack but which may be rendered sufficiently tacky by selected solvents for the seeming of good adhesions in many materials of commerce.
  • cotton in the form of a thread, yarn or fabric is treated with dextran, dissolved in a solvent, to secure penetration of the dextran into the fibers, and thereafter the dextran bearing cotton is treated with an alkylating agent in an alkaline solution and then subjected to a heating step to form a product resistant to chemical action but selectively attacked by particular solvents.
  • An additional feature of the process is the substantial elimination of residual stretch therefrom by the heating of the composite body under tensive conditions.
  • the alkylating agent for the dextran which is utilized to substitute or add an alkyl group into the dextran, may include: the organic halides such as methyl, ethyl, propyl; isopropyl or benzyl halides; the alkyl sulphates such as diethyl sulphate; tri-ethyl phosphate; and aryl sulfonic alkyl esters such as the ethyl ester of p-toluene sulfonic acid.
  • the organic halides such as methyl, ethyl, propyl
  • isopropyl or benzyl halides such as diethyl sulphate
  • tri-ethyl phosphate tri-ethyl phosphate
  • aryl sulfonic alkyl esters such as the ethyl ester of p-toluene sulfonic acid.
  • the alkylating agent is employed in alkaline solution this alkali is preferably sodium or potassium hydroxide, sodium carbonate or an organic alkali.
  • T he product of the process of invention may comprise, for example, a destretcied yarn having the cotton core surrounded by the benzyl ether of dextran which is insoluble in and substantially unaffected by H2O, alkalis, mineral acids, and the lower aliphatic alcohols, but which when treated with acetone, dioxane, benzene or toluene atent becomes tacky.
  • this destretched yarn has a particular utility in power transmission belt structures where it may be laminated with rubber and cured thereto.
  • a fabric treated by the process of invention attains qualities suitable for lamination with resinous materials.
  • Figure 2 is a view of the grooved roller in Figure 1;
  • Figure 3 is a partial plan view of the apparatus of Figure 1;
  • Figure 4 is a plan view of the grooved tapered roller shown in the oven of Figure 1.
  • FIG. 1 a tank or vat 1 containing a dextran solution 2, the solution containing by weight approrimately 40% dextran of any molecular weight, 55% water and about 5% of sodium hydroxide.
  • a cotton yarn 3 is shown passing continuously from bobbin 4, mounted on roll 5, into the solution 2 Where it is guided between rolls 6 and '1', which are adapted to be driven independently by means not shown at speeds differing by about 30%, the roll 7 having the greater velocity.
  • the rolls 6 and 7 are multi-grooved as shown in Figure 2 in order that the time of passage of the yarn through the solution may be readily controlled, by utilization of a selected number of grooves for particular size yarns.
  • the yarn is shown in Figure l as passing from solution 2 over roll 8 into bath 9 containing alkaline aralkyl halide solution 19 having by weight approximately 30% of benzyl chloride, 9% of sodium hydroxide and 61% water.
  • the wetted and impregnated yarn 3 passes over rolls 20 and 21 which are grooved similarly to rolls 6 and 7 and after a multi pass through the solution, as more clearly shown in Figure 3, enters a heated oven 12 over roller 31.
  • a hollow conical die 13 is positioned between bath 9 and oven 12 to remove any excess material present on the yarn before it passes to the heating operation,
  • the oven 12 is provided with grooved rollers 14, 15, roller 15 being driven at a speed about 30% in excess of that of roller 14, and the roller 15 having grooves of progressively ( Figure 4) increasing diameter, from end 16 to end 17, to facilitate the destretching of the yarn. After curing the yarn is wound up on coil 18 mounted on stand 19.
  • the yarn When impregnating and coating the yarn is passed through bath 2 under tension if desired although the same is not necessary but does assist in the ultimate de-stretching of the yarn and the dextran pick up is somewhat greater if tension is employed.
  • the dextran and aralkyl halide initiate a reaction which is completed in oven heater 112 at temperatures of about to C.
  • the finished product has substantially no stretch retained therein and due to the coating resists moisture thus preventing shrinkage effects from occurring in the yarn rendering the product particularly useful where constant yarn length under varying humidity conditions is essential. Since the productis also resistant to alcohols, the mineral acids, and alkalis, it may be employed under conditions where such resistance is beneficial.
  • the degree of impregnation of the yarn may be controlled by controlling the solution concentrations particularly the dextran. Furthermore a coating may be applied over the yarn to completely sheath the same by utilizing viscous solution.
  • Example 11 The apparatus described in connection with Example I may be readily modified to permit the coating of a cotton fabric with an ethyl dextran which is resistant to water, the mineral acids, and alkalis, but soluble in the alcohols.
  • the dextran may in this instance be solved in a weak sodium hydroxide, and an efiicient mixture would contain:
  • the fixing solution may contain:
  • An adhesive yarn consisting of a cotton core impregnated and coated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
  • Au adhesive yarn consisting of a cotton core irnpregnated and coated with an ethyl ether of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
  • An adhesive yarn consisting of a cotton core impregnated and coated with a benzyl ether of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
  • a fabric comprising adhesive yarns consisting of a cotton core coated and impregnated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially nonstretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the fabric.
  • a power transmission belt comprising yarns con-sisting of a cotton core coated and impregnated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the belt.
  • a power transmission belt comprising yarns consisting of a cotton core coated and impregnated with a benzyl ether of dextran, said core being set in substantial- 1y non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the belt.
  • the method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextran-impregnated cotton yarn with an aqueous alkaline solution of an etherifying agent selected from the group consisting of alkylating and aralkylating agents, heating the impregnated yarn to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with a solvent for the dextran ether to activate the ether to adhesive condition.
  • an etherifying agent selected from the group consisting of alkylating and aralkylating agents
  • the method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of C. to C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with acetone to activate the ether to adhesive condition.
  • the method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with dioxane to activate the ether to adhesive condition.
  • the method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etheritying agent and the dextran in situ in the yarn, and thereafter treating the yarn with benzene to activate the ether to adhesive condition.
  • the method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with toluene to activate the ether to adhesive condition.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

May 22, 1956 G. 1.. DENISTON ADHESIVE COTTON ARTICLE AND METHOD OF MAKING SAME Original Filed Aug. 14, 1951 INVENTOR GEORGE L. DENISTON ATTORNEYS ADHESIVE @GTTUN ARTHILE AND METHGD GF MAKING George L. Deniston, Dayton, (lhio, assignor to The (loinmonwealth Engineering Company of @hio, Dayton, @hio, a corporation of @hio Original application August 114, 1951, Serial No. 241,740, now Patent No. greases, dated Aprii 19, 1955. Di vided and this appiication September 22, 1952, Serial No. 3319304 12 Claims. (Q3. 117--63) This invention relates to a process of treating cotton threads, yarns and fabrics with dextran and its derivatives and to the products produced thereby.
This application is a division of application Serial No. 241,740, filed August 14, 1951, now U. S. Patent Serial No. 2,706,690, and assigned to the same assignee as the present invention.
Dextran is a water soluble colloidal material produced by the action of microorganisms on sucrose bearing materials and may be converted into dextran ethers and esters as described in U, S. Patents 2,344,179, 2,203,702 and 2,385,553.
This invention contemplates the provision of a novel process for the impregnation and coating of cotton materials with dextran and its derivatives.
The invention contemplates the provision of a new product wherein cotton provides a strength core and material impregnated therein and coated thereon provides an outer shell resistant to ordinary chemical attack but which may be rendered sufficiently tacky by selected solvents for the seeming of good adhesions in many materials of commerce.
More particularly, in the process of invention cotton in the form of a thread, yarn or fabric is treated with dextran, dissolved in a solvent, to secure penetration of the dextran into the fibers, and thereafter the dextran bearing cotton is treated with an alkylating agent in an alkaline solution and then subjected to a heating step to form a product resistant to chemical action but selectively attacked by particular solvents. An additional feature of the process, particularly as related to commercial yarn and fabrics as used in rubber and plastic industries, is the substantial elimination of residual stretch therefrom by the heating of the composite body under tensive conditions.
While i prefer to use a combination of sodium hydroxide and water as the dextran solvent, due to the efficiency of this combination the effecting of a swelling of the cotton fibers to thereby permit maximum penetration of the dextran, other solvents, e. g. water alone, water and sodium carbonate, a dilute acetic acid solution or dilute solutions of the mineral acids such as HCl and H2804 may suitably be employed.
The alkylating agent for the dextran, which is utilized to substitute or add an alkyl group into the dextran, may include: the organic halides such as methyl, ethyl, propyl; isopropyl or benzyl halides; the alkyl sulphates such as diethyl sulphate; tri-ethyl phosphate; and aryl sulfonic alkyl esters such as the ethyl ester of p-toluene sulfonic acid.
The alkylating agent is employed in alkaline solution this alkali is preferably sodium or potassium hydroxide, sodium carbonate or an organic alkali.
T he product of the process of invention may comprise, for example, a destretcied yarn having the cotton core surrounded by the benzyl ether of dextran which is insoluble in and substantially unaffected by H2O, alkalis, mineral acids, and the lower aliphatic alcohols, but which when treated with acetone, dioxane, benzene or toluene atent becomes tacky. Thus this destretched yarn has a particular utility in power transmission belt structures where it may be laminated with rubber and cured thereto. Similarly a fabric treated by the process of invention attains qualities suitable for lamination with resinous materials.
The invention will be more fully understood by reference to the following specific examples and the drawing wherein:
Figure l of invention;
Figure 2 is a view of the grooved roller in Figure 1;
Figure 3 is a partial plan view of the apparatus of Figure 1; and
Figure 4 is a plan view of the grooved tapered roller shown in the oven of Figure 1.
illustrates the apparatus used in the process Example I There is shown in Figure 1 a tank or vat 1 containing a dextran solution 2, the solution containing by weight approrimately 40% dextran of any molecular weight, 55% water and about 5% of sodium hydroxide. A cotton yarn 3 is shown passing continuously from bobbin 4, mounted on roll 5, into the solution 2 Where it is guided between rolls 6 and '1', which are adapted to be driven independently by means not shown at speeds differing by about 30%, the roll 7 having the greater velocity. The rolls 6 and 7 are multi-grooved as shown in Figure 2 in order that the time of passage of the yarn through the solution may be readily controlled, by utilization of a selected number of grooves for particular size yarns.
The yarn is shown in Figure l as passing from solution 2 over roll 8 into bath 9 containing alkaline aralkyl halide solution 19 having by weight approximately 30% of benzyl chloride, 9% of sodium hydroxide and 61% water. The wetted and impregnated yarn 3 passes over rolls 20 and 21 which are grooved similarly to rolls 6 and 7 and after a multi pass through the solution, as more clearly shown in Figure 3, enters a heated oven 12 over roller 31. A hollow conical die 13 is positioned between bath 9 and oven 12 to remove any excess material present on the yarn before it passes to the heating operation,
The oven 12 is provided with grooved rollers 14, 15, roller 15 being driven at a speed about 30% in excess of that of roller 14, and the roller 15 having grooves of progressively (Figure 4) increasing diameter, from end 16 to end 17, to facilitate the destretching of the yarn. After curing the yarn is wound up on coil 18 mounted on stand 19.
When impregnating and coating the yarn is passed through bath 2 under tension if desired although the same is not necessary but does assist in the ultimate de-stretching of the yarn and the dextran pick up is somewhat greater if tension is employed. In solution 10 the dextran and aralkyl halide initiate a reaction which is completed in oven heater 112 at temperatures of about to C.
The finished product has substantially no stretch retained therein and due to the coating resists moisture thus preventing shrinkage effects from occurring in the yarn rendering the product particularly useful where constant yarn length under varying humidity conditions is essential. Since the productis also resistant to alcohols, the mineral acids, and alkalis, it may be employed under conditions where such resistance is beneficial.
it will be clear from the foregoing that the degree of impregnation of the yarn may be controlled by controlling the solution concentrations particularly the dextran. Furthermore a coating may be applied over the yarn to completely sheath the same by utilizing viscous solution.
Example 11 The apparatus described in connection with Example I may be readily modified to permit the coating of a cotton fabric with an ethyl dextran which is resistant to water, the mineral acids, and alkalis, but soluble in the alcohols.
The dextran may in this instance be solved in a weak sodium hydroxide, and an efiicient mixture would contain:
50% dextran 40% water sodium hydroxide The fixing solution may contain:
50% (ii-ethyl sulphate 30% water sodium hydroxide The procedure is essentially the same as set forth in Example I, the heating temperature however being of the order of 100115 C.
It will be understood that while there have been given herein certain specific examples of the practice of this invention, it is not intended thereby to have this invention limited to or circumscribed by the specific details of materials, proportions or conditions herein specified, in view of the fact that this invention may be modified according to individual preference or conditions Without necessarily departing from the spirit of this disclosure and the scope of the appended claims.
I claim:
1. An adhesive yarn consisting of a cotton core impregnated and coated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
2. Au adhesive yarn consisting of a cotton core irnpregnated and coated with an ethyl ether of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
3. An adhesive yarn consisting of a cotton core impregnated and coated with a benzyl ether of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as a result of solvent treatment thereof in situ in the yarn.
4. A fabric comprising adhesive yarns consisting of a cotton core coated and impregnated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially nonstretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the fabric.
5. A power transmission belt comprising yarns con-sisting of a cotton core coated and impregnated with a substance selected from the group consisting of alkyl and aralkyl ethers of dextran, said core being set in substantially non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the belt.
6. A power transmission belt comprising yarns consisting of a cotton core coated and impregnated with a benzyl ether of dextran, said core being set in substantial- 1y non-stretchable condition by the dextran ether, and said ether being in adhesive condition in and on the core as the result of solvent treatment thereof in situ in the belt.
7. The method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextran-impregnated cotton yarn with an aqueous alkaline solution of an etherifying agent selected from the group consisting of alkylating and aralkylating agents, heating the impregnated yarn to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with a solvent for the dextran ether to activate the ether to adhesive condition.
8. The method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of C. to C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with acetone to activate the ether to adhesive condition.
9. The method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with dioxane to activate the ether to adhesive condition.
10. The method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etheritying agent and the dextran in situ in the yarn, and thereafter treating the yarn with benzene to activate the ether to adhesive condition.
11. The method of producing an adhesive cotton yarn which comprises treating a cotton yarn with an aqueous alkaline solution of dextran, then treating the dextranimpregnated cotton yarn with an aqueous alkaline solution of a benzyl ether of dextran, heating the impregnated yarn to a temperature of 130 C. to 140 C. to complete reaction between the etherifying agent and the dextran in situ in the yarn, and thereafter treating the yarn with toluene to activate the ether to adhesive condition.
12. The method of claim 7 in which the treatment with the aqueous solution of the etherifying agent is performed while the yarn is under tension.
References Cited in the file of this patent UNITED STATES PATENTS 148,319 Newton Mar. 10, 1874 2,126,936 Wall Aug. 16, 1938 2,203,705 Stahly et al. June 11, 1940 2,236,386 Stahly et al. Mar. 25, 1941 2,344,179 Stahly Mar. 14, 1944 2,486,399 Gagarine Nov. 1, 1949 2.503,624 Luaces Apr. 11, 1950

Claims (1)

  1. 7. THE METHOD OF PRODUCING AN ADHESIVE COTTON YARN WHICH COMPRISES TREATING A COTTON YARN WITH AN AQUEOUS ALKALINE SOLUTION OF DEXTRAN, THEN TREATING THE DEXTRAN-IMPREGNATED COTTON YARN WITH AN AQUEOUS ALKALINE SOLUTION OF AN ETHERIFYING AGENT SELECTED FROM THE GROUP CONSISTING OF ALKYLATING AND ARALKYLATING AGENTS, HEATING THE IMPREGNATED YARN TO COMPLETE REACTION BETWEEN THE ETHERIFYING AGENT AND THE DEXTRAN IN SITU IN THE YARN, AND THEREAFTER TREATING THE YARN WITH A SOLVENT FOR THE DEXTRAN ETHER TO ACTIVATE THE ETHER TO ADHESIVE CONDITION.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3066996A (en) * 1955-09-06 1962-12-04 Ohio Commw Eng Co Process and composition for stabilizing and vat dyeing regenerated cellulose textiles employing formaldehyde and water-soluble dextran

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US148319A (en) * 1874-03-10 Improvement in sizing cloths
US2126936A (en) * 1936-03-23 1938-08-16 Kali Mfg Company Textile finishing material
US2203705A (en) * 1938-02-26 1940-06-11 Commw Engineering Corp Soluble benzyl ether of dextran
US2236386A (en) * 1938-11-04 1941-03-25 Commw Engineering Corp Organic solvent soluble benzyl ether of dextran
US2344179A (en) * 1939-11-24 1944-03-14 Chemical Developments Corp Ethyl ether of dextran
US2486399A (en) * 1947-10-28 1949-11-01 Dan River Mills Inc Polymeric polyhydric alcohol condensation products and treatment of cellulosic textiles therewith
US2503624A (en) * 1946-02-08 1950-04-11 New Wrinkle Inc Dextran base wrinkle drying compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US148319A (en) * 1874-03-10 Improvement in sizing cloths
US2126936A (en) * 1936-03-23 1938-08-16 Kali Mfg Company Textile finishing material
US2203705A (en) * 1938-02-26 1940-06-11 Commw Engineering Corp Soluble benzyl ether of dextran
US2236386A (en) * 1938-11-04 1941-03-25 Commw Engineering Corp Organic solvent soluble benzyl ether of dextran
US2344179A (en) * 1939-11-24 1944-03-14 Chemical Developments Corp Ethyl ether of dextran
US2503624A (en) * 1946-02-08 1950-04-11 New Wrinkle Inc Dextran base wrinkle drying compositions
US2486399A (en) * 1947-10-28 1949-11-01 Dan River Mills Inc Polymeric polyhydric alcohol condensation products and treatment of cellulosic textiles therewith

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3066996A (en) * 1955-09-06 1962-12-04 Ohio Commw Eng Co Process and composition for stabilizing and vat dyeing regenerated cellulose textiles employing formaldehyde and water-soluble dextran

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