[go: up one dir, main page]

US2593466A - Viscose spinning solution - Google Patents

Viscose spinning solution Download PDF

Info

Publication number
US2593466A
US2593466A US39194A US3919448A US2593466A US 2593466 A US2593466 A US 2593466A US 39194 A US39194 A US 39194A US 3919448 A US3919448 A US 3919448A US 2593466 A US2593466 A US 2593466A
Authority
US
United States
Prior art keywords
viscose
amine
reaction
weight
amines
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
Application number
US39194A
Inventor
Robert D Maclaurin
William O Israel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Industrial Rayon Corp
Original Assignee
Industrial Rayon Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Industrial Rayon Corp filed Critical Industrial Rayon Corp
Priority to US39194A priority Critical patent/US2593466A/en
Application granted granted Critical
Publication of US2593466A publication Critical patent/US2593466A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

  • the present invention has for its object a new and improved viscose solution for use in the production of such yarn as well as a process by which such viscose solutions and produced.
  • viscose spinning solutions In the preparation of viscose spinning solutions the viscose is customarily filtered one or more times through various fine cloth media before it is extruded into a coagulating bath. Difficulty however is frequently encountered in producing viscose solutions that are free of minute undispersed and undissolved particles which clog the pores of the filter media prematurely or pass through the pores and later clog the orifices of spinnerets thereby resulting in yarns of low strength and poor uniformity. Such extraneous particles may consist of resinous materials found in wood pulp undissolved or partially dissolved cellulose xanthate gels and semisolids, etc.
  • crustationj inhibiting agent employed in a co- 1 agulating bath.
  • alkylene oxides which are particularly suitable in forming the amine-alkylene oxide reaction products employed in the present invention are ethylene and propylene oxide.
  • Advantageous results are derived where the aminealkylene oxide compounds employed represent the reaction of between about 12 and 100 moles of an alkylene oxide per mole amine and with particular advantage where the moles of alkylene oxide per mole of amine are between about 14 and 75 and preferably between about 18 and 60.
  • the above defined primary or secondary amines or mixtures thereof which are reacted with an alkylene oxide may if desired contain other substitutents in addition to the alkyl and alkenyl radicals specified such as, for example, aryl radicals or other amine radicals. In the latter situation there may be mentioned the mono-, di-, trietc. amines. Examples of various typical amines which may be reacted to produce the amine derivatives employed in the present invention will appear later in the specification:
  • the amine reactants having alkyl or alkenyl radicals containing more than 6 carbon atoms are preferred such as for example oxide compounds made from mixtures of amines having a mean molecular weight of at least about 175 or 185 and more advantageouslyof at least about 200.
  • oxide compounds made from mixtures of amines having a mean molecular weight of at least about 175 or 185 and more advantageouslyof at least about 200.
  • mixtures of amines may be used as starting materials in which at least about mole percent of the amines have radicalscontaining from 12 to 18 carbon atoms and in addition thereto either 20 mole percent containing from 14 to 18 carbon atoms or the amine mixture having a mean molecular weight of about 175.
  • Particularly advantageous results are derived where 80 mole percent of the amine mixtures have radicals containing '14 to 18 carbon atoms or in addition 20 molepercent containing from 16 to 18 carbon atoms.
  • alkylene oxide reaction product may be added if desired at one or more of the viscose preparation stages such as, for example, (a) to a chemically prepared wood pulp which has been refined for the manufacture of viscose, prior to or during the shredding of the alkali cellulose, (c)
  • Example 1 534 parts of normal primary octadecenylamine is mixed with 5 parts of a 50% aqueous sodium dissolving step, and (d) to dissolved cellulose xanthate (viscose) before or after filtration or both. Particularly advantageous results are derived where the reaction product is added to and admixed with a viscose solution prior to filtration.
  • the compounds useful in practicing the invention may, in general, be prepared in the following manner.
  • a weighed quantity of one or more of the amines mentioned is mixed with a small amount of an alkaline catalyst such as, for example, about 0.5 to 2%, by weight, sodium hydroxide in the form of a solid or of a 50% aqueous solution.
  • an alkaline catalyst such as, for example, about 0.5 to 2%, by weight, sodium hydroxide in the form of a solid or of a 50% aqueous solution.
  • alkali or alkaline earth metal catalysts may be used in the place of sodium hydroxide, such as for example, potassium hydroxide or the alkali metal alcoholates, e. g. sodium methylate.
  • the mixture is introduced into a pressure resistant vessel such as an autoclave which is equipped with suitable agitating, heating and cooling means. The contents of the autoclave are then heated while stirring to an initial reaction temperature of from about 100 C.
  • an alkaline oxide such as, for example, ethylene or propylene oxide is then introduced into the autoclave preferably through a suitable meter while the mixture is agitated.
  • the rate of addition of the alkylene oxide depends among other things upon the efficiency of the means for dissipating the heat of the reaction.
  • the duration of the reaction may extend over a period of from 1 to 3 hours or more depending among other things upon the amount and character of each of the reactants. 'I'he'temperature during the reaction is preferably maintained at about 125 C. and the pressure is not permitted to exceed about 200 pounds per square inch.
  • the temperature control and agitation of the contents of the autoclave is continued until the reaction is complete as is indicated by a gradual drop in pressure and by a rapid decrease in temperature.
  • the contents of the autoclave may then be discharged and permitted to cool to room temperature.
  • the reaction products are all soluble in water or alcohol and also in various aqueous acid or alkalineliquids.
  • the character of the reaction product may range from a viscous liquid to a semisolid or solid.
  • a quantity of the amine-alkylene oxide reaction product which is dissolved in a suitable solvent such .as for example Water is added to andmixed with viscose forming materials at one or more of hydroxide solution as a catalyst and placed in an autoclave where it is heated to an initial reaction temperature of C. while stirring the mixture. Then 1056 parts of ethylene oxide is gradually introduced into the autoclave over a period of one hour and forty minutes and the temperature is permitted to rise to about 144 C.
  • the reaction product thus formed is a brownish waxy solid which is soluble in water and represents the reaction of about 12 moles of ethylene oxide per mole of amine.
  • a suitable quantity of the reaction product is dissolved in water to make up a 30%, by weight, stock solution and the stock solution gradually added to and mixed With a filtered viscose spinning solution until the viscose contains, about 0.05%, by weight, of the reaction product based on the weight of the viscose, the viscose containing about 8% cellulose and about 6.5% sodium hydroxide.
  • the viscose spinning solution prepared in' this manner is clear and transparent, and when extruded into a coagulating bath containing, by weight, about 10% sulfuric acid, 20% sodium sulfate and 1% zinc sulfate, does not clog the spinneret orifices after prolonged continuous periods of spinning.
  • the yarn produced is desirably uniform in appearance and strength.
  • Example 2 The procedure of Example 1 is followed with the exception that 2112 parts of ethylene oxide is introduced into the autoclave over a period of about 2 /2 hours.
  • the reaction product representing the reaction of about 24 moles of ethylene oxide per mole of amine is similar to the product of "Example 1 both in'character and in its'eifectiveness with the exception that only about 0.025%, by weight, of the product is incorporated in the viscose.
  • Example 3 The procedure of Example 1 is followed with the exception -that 267. parts of the octadecenylamine is reacted with 1180 parts of propylene oxide, the latter being introduced over a period of 3 to 4 hours.
  • the initial reaction temperature is about C. and the temperature is not permitted to rise above about C. while the .pressure is not permitted to rise above about 85 pounds per square inch.
  • Th reaction product is similar in character and effectiveness to that of Example 1 and represents the reaction of about 20 moles of propylene oxide per mole of the amine.
  • Example 4 5 parts of a 50% sodium hydroxide solution is mixed with 71 parts of secondary dodecyl amine and 215 parts of normal primary octadecyl amine and the mixture placed in an autoclave where it is heated to an initial reaction temperature of 130 C. while stirring the mixture. Then 1320 parts of ethylene oxide is gradually introduced into the autoclave over a period of about 2 hours andthe temperature is permitted to rise toabout 150 C. while the maximum pressure attained is about 150- pounds per square inch; After all of the ethylene oxide has been introduced and the reaction is completed as is indicated by a gradual decrease in pressure to zero gauge, the material is evacuated from the autoclave and permitted to cool to room, temperature.
  • the reaction produce formed is a brown waxy solid which is soluble in water and represents the reaction of about 30 moles of ethylene oxide per mean'mole of the mixture of amines having a mean molecular weight of about 286.
  • An aqueous solution of the resulting reaction product is prepared and incorporated in a viscose solution in the manner and under the conditions of Example 1 with the I Example 5 5 parts of a 50% aqueous sodium hydroxide solution as a catalyst is mixed with the following normal primary amines; 133 parts of octadecadienyl amine; 48 parts of hexadecyl' amine, 21 parts of tetradecyl amine, and, 37 parts of. dodecyl amine.
  • the mixture is then placed in an autoclave where it is heated to an initial reaction temperature of about 130 C. while stirring the mixture. Then 1760 parts of ethylene oxide is gradually introduced into the autoclave'over a period of about 2 /2 hours and the temperature is permitted to rise to about 160 C. while the maximum pressure attained is about 150 pounds per square inch. After all of the ethylene oxide has been introduced and the reaction is completed as indicated by a gradual decrease in pressure to zero gauge, the material is evacuated from the autoclave and permitted to. cool to room temperature.
  • the reaction product formed is a waxy solid. which is solublein. Water and represents thereaction of about 40 moles. of ethylene oxide per mean mole of the mixture of amines having a, mean. molecular Weight. of about. 240.
  • the resulting reaction. product is dissolved in water to form an aqueous solution containing about 30%, by weight, of the product and. this. solution is gradually added to and mixed with a freshly prepared viscose solution prior to the filtration thereof.
  • the composition of the viscose is the same as that described in Example 1.
  • a sufllcient quantity of the reaction product is added to form a viscose solution containing about 0.05%, by weight, of the product based on the weight of the viscose.
  • the viscose solution prepared. in this manner results in longer periods of continuous viscose filtration and also in a filtered viscose spinning solution which is clear, trans-,
  • the yarn produced is desirably uniform and has improved strength.
  • 5 parts of a 50% aqueous sodium hydroxide solution as a catalyst is mixed with the following normal primary amines; 5 parts of hexyl amine, 6 parts of octylamine, 16 parts decylamine, 83 parts of dodecylamine, 43 parts of tetradecylamine and 40 parts of octadecylamine.
  • the mixture is then reacted with 2200 parts of ethylene oxide in the manner and under the conditions described in Example 5.
  • the reac-- tion product represents the reaction of about 50 moles of ethylene oxide with one mean mole of the mixture of amines having a mean molecular weight of about19l.
  • a quantity of the reaction product is dissolved in water to form a 30%, by weight, aqueous stock solution and the stock solution is gradually added to and mixed with a viscose solution of the composition described in Example 1.
  • the addition is made both before filtration and after filtration of the viscose in quantities sufiicient to form a filtered viscose spinning: solution containing about 0.04%, by weight, of the reaction product.
  • Example 7 The procedure of Example 5 is followed with the exception that 2640 parts of ethylene oxide is introduced into the autoclave over a period of about 3% hours and reacted with the following normal primary amines; 8 parts of decylamine, 28 parts of dodeoylamine, 85 parts of tetradecylamine, 72 parts of hexadecylamine and 27 parts of octadecenylamine'.
  • the product represents the reaction of about'60 moles of ethylene oxide with one mean mole of the mixture of amines having a mean molecular weight of about 220.
  • Example 8 The procedure in this example is the same as that set forth in Example 7 with the exception that 3520 parts of ethylene oxide is introduced into the autoclave over a period of about 4 /2 hours to produce a reaction product having about moles of ethylene oxide per mean mole of th mixture of amines.
  • Example 9 The procedure of Example 5 is followed with the exception that the following mixture of primary normal amines are reacted; 24 parts of hexadecylamine, 27 parts of octadecylamine, 80 parts of octadecenylamine, and 133 parts of octadecadienyl amine.
  • the resulting reaction product which is incorporated in the viscose represents the reaction of about 40 moles of ethylene oxide per mean mole, the amine mixture having a mean molecular weight of about 264.
  • Example 10 A suitable quantity of the amine-ethylene oxide reaction product of Example 9 was dissolved in water to form a 50%, by weight, aqueous solution and the aqueous solution sprayed onto a batch. of alkali cellulose (soda cellulose) prior to the shredding operation.
  • the quantity of the reaction product employed is sufficient to form a shreddedv alkali cellulose containing about 0.8%, by weight, of the reaction product based on the weight'of the cellulose.
  • Example 11 The procedure of Example is followed with the exception that the aqueous solution of the amine-ethylene oxide reaction product is gradually introduced into a cellulose xanthate dissolving vessel and mixed with the cellulose xanthate crumbs and the aqueous caustic soda solvent therefor, prior to the completion of the dissolv ing step.
  • a sufiicient quantity of the reaction product is employed to form a viscose containing about 0.08%, by weight, of the reaction product.
  • the results obtained are similar to those of Example 10 as regards the filtration of the viscose, the uniformity and clarity of the filtered viscose, and character of the yarn product.
  • Example 12 treated wood pulp containing about 0.2%, by.
  • tlie'amine-' alkylene oxide reaction product may, if desired, be employed in the preparation of various types of viscose solutions; such as'for example those containing and those not containing delustering materials such as for example finely divided and dispersed particles of titanium dioxide, waxes, oils, etc.
  • delustering materials such as for example finely divided and dispersed particles of titanium dioxide, waxes, oils, etc.
  • the incorporation of the amine-alkylene oxide reaction product may with advantage improve the degree, stability, and uniformity of the dispersion of the delustering particles in the viscose.
  • the amine derivatives may be added to and incorporated in chemically prepared cellulose such as wood pulp,'cotton, etc. prior to the formation of alkali cellulose therefrom, or, if desired, they may be addedto' the alkali cellulose. In either situation it is found advantageous to incorporate between about 0.01 and 1.0%, by weight, of the amine derivatives, based on the weight of the bone dry cellulose and with particular advantage" between about 0.05 and 0.8%.
  • the amounts added at the several stages of viscose preparation may be such as to form a viscose solution containing between about 0.01 and 0.2%, by weight, of the amine derivative based on the weight of the viscose solution.
  • amines which may be reacted with an alkylene oxide to produce the products useful in the present invention may include normal monoamines of the aliphatic series such as hexylamine, heptylamine, octylamine, nonylamine,
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed by the reaction of at least about 12 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; at least about mole percent of said mixture of amines containing from 12 to 18 carbon atoms.
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms, at least about 80 mole percent of said mixture of amines containing from 6 to 18 carbon atoms, at least about 80 mole percent of said mixture of amines containing from 14 to 18 carbon atoms. 7
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; at least about 80 mole percent of said mixture of amines containing from 14 to 18 carbon atoms and at least about 20 mole percent containing from 16 to 18 carbon atoms.
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 14 and 75 moles of an ethylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting' of alkyl and alkenyl amines containing from 6 to 18 carbon atoms, said mixture of amines having a mean molecular weight of at least about 200 and atleast about 70 mole percent of said mixture of amines containing from 16 to 18 carbon atoms.
  • a viscose spinning solution having incorpo-;' rated therein between about 0.01 and 0.2%; by weight, of a product formed from the reactionof; between about 12 and 100 moles of ethylene ox" e" with one mole of normal primary octadecylamifie.
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of ethylene oxide with one mole of normal primary octa decenylamine.
  • a viscose spinning solution having incorpoi rated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of ethylene oxide sisting of alkyl and alkenyl amines containing.
  • composition comprising a product formed by the reaction of between about 12' and 100 moles of an alkylene oxide with one mole of a 10 primary aliphatic amine selected from the group consisting of alkyl and alkenyl amines containing from 12 to 18 carbons atoms.
  • a viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; said mixture of amines having a mean molecular weight of at least about 185.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)

Description

Patented Apr. 22, 1952 viscose, SPINNING SOLUTION Robert D. MacLaurin and William 0. Israel, Lakewood, Ohio, assignors to Industrial Rayon Corporation, Cleveland, Ohio,
Delaware a corporation oit No Drawing Application July 16, 1948,
' 7 Serial No. 39,194
l The present invention has for its object a new and improved viscose solution for use in the production of such yarn as well as a process by which such viscose solutions and produced.
In the preparation of viscose spinning solutions the viscose is customarily filtered one or more times through various fine cloth media before it is extruded into a coagulating bath. Difficulty however is frequently encountered in producing viscose solutions that are free of minute undispersed and undissolved particles which clog the pores of the filter media prematurely or pass through the pores and later clog the orifices of spinnerets thereby resulting in yarns of low strength and poor uniformity. Such extraneous particles may consist of resinous materials found in wood pulp undissolved or partially dissolved cellulose xanthate gels and semisolids, etc. The presence of such particles in a filtered viscose solution is usually evidenced by the lack of transparency and high turbidity of the spinning solution. In some situations even relatively large sized particles in the form of fluid semisolids or gel-like substances successively slip throughjthe pores of the filter media. In addition such particles upon standing in a stored and filtered viscose solution may tend to agglomerateand as a result further increase the difficulties mentioned.
In order to eliminate one or more of the difficulties mentioned there have been proposed heretofore the incorporation of various organic surface-active compounds at one or more of the stages of-viscose production. In general however such additives have not been entirely successful for one or more of the following reasons, i. e., they may be unstable in the caustic soda solutions encountered in the various stages of viscose prepartion; they may tend to lose their dispersing power in viscose on standing during the normal viscose storage and ripening periods; their dispersing powers may be too low, thus requiring yarn may be the incorporation of excessive amounts which may patible with and reduce the efiicienc'y of th. in-
crustationj inhibiting agent employed in a co- 1 agulating bath.
In accordance with the present invention it has been found that the above mentioned difficulties may be obviated and that an improved viscose spinning solution inay be produced by incorporat- 13 Claims. (Cl. 106165) ing into the viscose at any stage of its preparation a product formed from the reaction of at least about 12 moles of an alkylene oxide with one mole of a primary or secondary aliphatic amine or mixtures thereof, the amines being alkyl or alkenyl amines containing from 6 to 18 carbon atoms.
Among the alkylene oxides which are particularly suitable in forming the amine-alkylene oxide reaction products employed in the present invention are ethylene and propylene oxide. Advantageous results are derived where the aminealkylene oxide compounds employed represent the reaction of between about 12 and 100 moles of an alkylene oxide per mole amine and with particular advantage where the moles of alkylene oxide per mole of amine are between about 14 and 75 and preferably between about 18 and 60. a
The above defined primary or secondary amines or mixtures thereof which are reacted with an alkylene oxide may if desired contain other substitutents in addition to the alkyl and alkenyl radicals specified such as, for example, aryl radicals or other amine radicals. In the latter situation there may be mentioned the mono-, di-, trietc. amines. Examples of various typical amines which may be reacted to produce the amine derivatives employed in the present invention will appear later in the specification:
In general the amine reactants having alkyl or alkenyl radicals containing more than 6 carbon atoms are preferred such as for example oxide compounds made from mixtures of amines having a mean molecular weight of at least about 175 or 185 and more advantageouslyof at least about 200. With similar advantage mixtures of amines may be used as starting materials in which at least about mole percent of the amines have radicalscontaining from 12 to 18 carbon atoms and in addition thereto either 20 mole percent containing from 14 to 18 carbon atoms or the amine mixture having a mean molecular weight of about 175. Particularly advantageous results are derived where 80 mole percent of the amine mixtures have radicals containing '14 to 18 carbon atoms or in addition 20 molepercent containing from 16 to 18 carbon atoms.
Similar advantages are derived where the amine mixture has a mean molecular weight of at least 185 and mole percent thereof have In practicing the present invention the amine:
alkylene oxide reaction product may be added if desired at one or more of the viscose preparation stages such as, for example, (a) to a chemically prepared wood pulp which has been refined for the manufacture of viscose, prior to or during the shredding of the alkali cellulose, (c)
to cellulose xanthate crumbs before or during the 4 the stages of the viscose preparation so as to form a viscose spinning solution containing for example between about 0.01 and 0.2%, by weight, of the reaction product based on the weight of the viscose. w
' The following specific examples in which parts by weight are given will serve to illustrate the present invention, although it will be understood that the invention is not limited to the specific conditions set forth.
Example 1 534 parts of normal primary octadecenylamine is mixed with 5 parts of a 50% aqueous sodium dissolving step, and (d) to dissolved cellulose xanthate (viscose) before or after filtration or both. Particularly advantageous results are derived where the reaction product is added to and admixed with a viscose solution prior to filtration.
The compounds useful in practicing the invention may, in general, be prepared in the following manner. A weighed quantity of one or more of the amines mentioned is mixed with a small amount of an alkaline catalyst such as, for example, about 0.5 to 2%, by weight, sodium hydroxide in the form of a solid or of a 50% aqueous solution. Other alkali or alkaline earth metal catalysts may be used in the place of sodium hydroxide, such as for example, potassium hydroxide or the alkali metal alcoholates, e. g. sodium methylate. The mixture is introduced into a pressure resistant vessel such as an autoclave which is equipped with suitable agitating, heating and cooling means. The contents of the autoclave are then heated while stirring to an initial reaction temperature of from about 100 C. to about 200 C., the range between about 125 C. to about 150 C. being preferred to facilitate the control of the reaction. After the initial reaction temperature is attained a weighed amount of an alkaline oxide such as, for example, ethylene or propylene oxide is then introduced into the autoclave preferably through a suitable meter while the mixture is agitated. The rate of addition of the alkylene oxide depends among other things upon the efficiency of the means for dissipating the heat of the reaction. The duration of the reaction may extend over a period of from 1 to 3 hours or more depending among other things upon the amount and character of each of the reactants. 'I'he'temperature during the reaction is preferably maintained at about 125 C. and the pressure is not permitted to exceed about 200 pounds per square inch. After all of the alkylene oxide has been introduced the temperature control and agitation of the contents of the autoclave is continued until the reaction is complete as is indicated by a gradual drop in pressure and by a rapid decrease in temperature. The contents of the autoclave may then be discharged and permitted to cool to room temperature. The reaction products are all soluble in water or alcohol and also in various aqueous acid or alkalineliquids.
Depending upon the character and molecular weight of the amine or mixture of amines and upon the number of moles of alkylene oxide which are reacted the character of the reaction product may range from a viscous liquid to a semisolid or solid. In practicing the present invention a quantity of the amine-alkylene oxide reaction product which is dissolved in a suitable solvent such .as for example Water is added to andmixed with viscose forming materials at one or more of hydroxide solution as a catalyst and placed in an autoclave where it is heated to an initial reaction temperature of C. while stirring the mixture. Then 1056 parts of ethylene oxide is gradually introduced into the autoclave over a period of one hour and forty minutes and the temperature is permitted to rise to about 144 C. while the maximum pressure attained is about 100 pounds per square inch. After all of the ethylene oxide has been introduced and the reaction is completed as is indicated by a gradual decrease in pressure to zero gauge, the material is evacuated from the autoclave and permitted to cool to room temperature. The reaction product thus formed is a brownish waxy solid which is soluble in water and represents the reaction of about 12 moles of ethylene oxide per mole of amine.
A suitable quantity of the reaction product is dissolved in water to make up a 30%, by weight, stock solution and the stock solution gradually added to and mixed With a filtered viscose spinning solution until the viscose contains, about 0.05%, by weight, of the reaction product based on the weight of the viscose, the viscose containing about 8% cellulose and about 6.5% sodium hydroxide. The viscose spinning solution prepared in' this manner is clear and transparent, and when extruded into a coagulating bath containing, by weight, about 10% sulfuric acid, 20% sodium sulfate and 1% zinc sulfate, does not clog the spinneret orifices after prolonged continuous periods of spinning. In addition the presence of the amine reactionproduct in the viscose and in the coagulating bath inhibits the formation of 'incrustations on the spinneret face and on other devices operatively associated with the coagulating bath liquid. The yarn produced is desirably uniform in appearance and strength.
Example 2 The procedure of Example 1 is followed with the exception that 2112 parts of ethylene oxide is introduced into the autoclave over a period of about 2 /2 hours. The reaction product representing the reaction of about 24 moles of ethylene oxide per mole of amine is similar to the product of "Example 1 both in'character and in its'eifectiveness with the exception that only about 0.025%, by weight, of the product is incorporated in the viscose.
Example 3 The procedure of Example 1 is followed with the exception -that 267. parts of the octadecenylamine is reacted with 1180 parts of propylene oxide, the latter being introduced over a period of 3 to 4 hours. The initial reaction temperature is about C. and the temperature is not permitted to rise above about C. while the .pressure is not permitted to rise above about 85 pounds per square inch. Th reaction product is similar in character and effectiveness to that of Example 1 and represents the reaction of about 20 moles of propylene oxide per mole of the amine.
Example 4 5 parts of a 50% sodium hydroxide solution is mixed with 71 parts of secondary dodecyl amine and 215 parts of normal primary octadecyl amine and the mixture placed in an autoclave where it is heated to an initial reaction temperature of 130 C. while stirring the mixture. Then 1320 parts of ethylene oxide is gradually introduced into the autoclave over a period of about 2 hours andthe temperature is permitted to rise toabout 150 C. while the maximum pressure attained is about 150- pounds per square inch; After all of the ethylene oxide has been introduced and the reaction is completed as is indicated by a gradual decrease in pressure to zero gauge, the material is evacuated from the autoclave and permitted to cool to room, temperature. The reaction produce formed is a brown waxy solid which is soluble in water and represents the reaction of about 30 moles of ethylene oxide per mean'mole of the mixture of amines having a mean molecular weight of about 286. An aqueous solution of the resulting reaction product is prepared and incorporated in a viscose solution in the manner and under the conditions of Example 1 with the I Example 5 5 parts of a 50% aqueous sodium hydroxide solution as a catalyst is mixed with the following normal primary amines; 133 parts of octadecadienyl amine; 48 parts of hexadecyl' amine, 21 parts of tetradecyl amine, and, 37 parts of. dodecyl amine. The mixture is then placed in an autoclave where it is heated to an initial reaction temperature of about 130 C. while stirring the mixture. Then 1760 parts of ethylene oxide is gradually introduced into the autoclave'over a period of about 2 /2 hours and the temperature is permitted to rise to about 160 C. while the maximum pressure attained is about 150 pounds per square inch. After all of the ethylene oxide has been introduced and the reaction is completed as indicated by a gradual decrease in pressure to zero gauge, the material is evacuated from the autoclave and permitted to. cool to room temperature. The reaction product formed is a waxy solid. which is solublein. Water and represents thereaction of about 40 moles. of ethylene oxide per mean mole of the mixture of amines having a, mean. molecular Weight. of about. 240. The resulting reaction. product is dissolved in water to form an aqueous solution containing about 30%, by weight, of the product and. this. solution is gradually added to and mixed with a freshly prepared viscose solution prior to the filtration thereof. The composition of the viscose is the same as that described in Example 1. A sufllcient quantity of the reaction product is added to form a viscose solution containing about 0.05%, by weight, of the product based on the weight of the viscose. The viscose solution prepared. in this manner results in longer periods of continuous viscose filtration and also in a filtered viscose spinning solution which is clear, trans-,
parent. The yarn produced is desirably uniform and has improved strength.
Example 6.
5 parts of a 50% aqueous sodium hydroxide solution as a catalyst is mixed with the following normal primary amines; 5 parts of hexyl amine, 6 parts of octylamine, 16 parts decylamine, 83 parts of dodecylamine, 43 parts of tetradecylamine and 40 parts of octadecylamine. The mixture is then reacted with 2200 parts of ethylene oxide in the manner and under the conditions described in Example 5. The reac-- tion product represents the reaction of about 50 moles of ethylene oxide with one mean mole of the mixture of amines having a mean molecular weight of about19l.
A quantity of the reaction product is dissolved in water to form a 30%, by weight, aqueous stock solution and the stock solution is gradually added to and mixed with a viscose solution of the composition described in Example 1. The addition is made both before filtration and after filtration of the viscose in quantities sufiicient to form a filtered viscose spinning: solution containing about 0.04%, by weight, of the reaction product.
Example 7 The procedure of Example 5 is followed with the exception that 2640 parts of ethylene oxide is introduced into the autoclave over a period of about 3% hours and reacted with the following normal primary amines; 8 parts of decylamine, 28 parts of dodeoylamine, 85 parts of tetradecylamine, 72 parts of hexadecylamine and 27 parts of octadecenylamine'. The product represents the reaction of about'60 moles of ethylene oxide with one mean mole of the mixture of amines having a mean molecular weight of about 220.
Example 8 The procedure in this example is the same as that set forth in Example 7 with the exception that 3520 parts of ethylene oxide is introduced into the autoclave over a period of about 4 /2 hours to produce a reaction product having about moles of ethylene oxide per mean mole of th mixture of amines.
Example 9 The procedure of Example 5 is followed with the exception that the following mixture of primary normal amines are reacted; 24 parts of hexadecylamine, 27 parts of octadecylamine, 80 parts of octadecenylamine, and 133 parts of octadecadienyl amine. The resulting reaction product which is incorporated in the viscose represents the reaction of about 40 moles of ethylene oxide per mean mole, the amine mixture having a mean molecular weight of about 264.
Example 10 A suitable quantity of the amine-ethylene oxide reaction product of Example 9 was dissolved in water to form a 50%, by weight, aqueous solution and the aqueous solution sprayed onto a batch. of alkali cellulose (soda cellulose) prior to the shredding operation. The quantity of the reaction product employed is sufficient to form a shreddedv alkali cellulose containing about 0.8%, by weight, of the reaction product based on the weight'of the cellulose. By preparing viscose in this-manner a finer and more uniformly shredded alkali cellulose is obtained which in turn permits a more uniform and more complete xanthation of the alkali cellulose and dissolution of the cellulose xanthate into viscose. In addition more rapid, and more prolonged periods of continuous viscose filtration are achieved and a clear and transparent viscose results which may be spun into yarn of desirable uniformity and strength.
Example 11 The procedure of Example is followed with the exception that the aqueous solution of the amine-ethylene oxide reaction product is gradually introduced into a cellulose xanthate dissolving vessel and mixed with the cellulose xanthate crumbs and the aqueous caustic soda solvent therefor, prior to the completion of the dissolv ing step. A sufiicient quantity of the reaction product is employed to form a viscose containing about 0.08%, by weight, of the reaction product. The results obtained are similar to those of Example 10 as regards the filtration of the viscose, the uniformity and clarity of the filtered viscose, and character of the yarn product.
Example 12 treated wood pulp containing about 0.2%, by.
weight, of the reaction product based on the weight of the bone dry cellulose. tered viscose solution prepared from the above treated wood pulp is then added a suflicient quantity of the 50% aqueous solution of the amine derivative to form a viscose containing about 0.05%, by weight, of the amine derivative based on the weight of the viscose. The results obtained are similar to those described in Example 10.
In practicing the present invention tlie'amine-' alkylene oxide reaction product may, if desired, be employed in the preparation of various types of viscose solutions; such as'for example those containing and those not containing delustering materials such as for example finely divided and dispersed particles of titanium dioxide, waxes, oils, etc. Under certain conditions the incorporation of the amine-alkylene oxide reaction product may with advantage improve the degree, stability, and uniformity of the dispersion of the delustering particles in the viscose.
As previously stated the amine derivatives may be added to and incorporated in chemically prepared cellulose such as wood pulp,'cotton, etc. prior to the formation of alkali cellulose therefrom, or, if desired, they may be addedto' the alkali cellulose. In either situation it is found advantageous to incorporate between about 0.01 and 1.0%, by weight, of the amine derivatives, based on the weight of the bone dry cellulose and with particular advantage" between about 0.05 and 0.8%.
Further advantages are however derived where relatively small amounts of the amine derivatives are added both at some point before the xanthation step and also after the dissolution of the cellulose xanthate into viscose. Advantageously the amounts added at the several stages of viscose preparation may be such as to form a viscose solution containing between about 0.01 and 0.2%, by weight, of the amine derivative based on the weight of the viscose solution.
Other amines which may be reacted with an alkylene oxide to produce the products useful in the present invention may include normal monoamines of the aliphatic series such as hexylamine, heptylamine, octylamine, nonylamine,
To an unfila 8 decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine,
hexadecylamine, heptadecylamine, octadecylamine; or, diamines or the aliphatic series including 1,6 hexanediamine, 1,7 heptane diamine, 1,8 octyl diamine, 1,9 nonyl diamine, 1,10 dodecylamine, 1,11 undecyl diamine, 1,12 dodecyl diamine, l,13 tridecyl diamine, 1,14 tetradecyl diamine, 1,15 pentadecyl diamine, 1,16 hexadecyl diamine, 1,17 heptadecyl diamine, 1,18 octadecyle diamine, or normal monoamines derived from the olefinic series such as hexenyl amine, heptenyl amine, octenyl amine, nonenyl amine, decenyl amine, undecenyl amine, dodecenyl amine, tridecenyl amine, pentadecenyl amine, hexadecenyl amine, heptadecenyl amine, and octadecenyl amine, or diamines derived from the olefinic series such as 1,6 amino hexene, 1,7 amino heptene, 1,8 amino ,octene, 1,9 amino nonene, 1,10 aminodecene, 1,11 amino undecene, 1,12 amino dodecene, 1,13 amino tridecene, 1,14 amino tetradecene, 1,15 amino pentadecene, 1,16 amino hexadecene, 1,17 amino heptadecene, and 1,18 amino octadecene.
We claim:
1. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed by the reaction of at least about 12 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; at least about mole percent of said mixture of amines containing from 12 to 18 carbon atoms.
2. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms, at least about 80 mole percent of said mixture of amines containing from 6 to 18 carbon atoms, at least about 80 mole percent of said mixture of amines containing from 14 to 18 carbon atoms. 7
3. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; at least about 80 mole percent of said mixture of amines containing from 14 to 18 carbon atoms and at least about 20 mole percent containing from 16 to 18 carbon atoms.
,4. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 14 and 75 moles of an ethylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting' of alkyl and alkenyl amines containing from 6 to 18 carbon atoms, said mixture of amines having a mean molecular weight of at least about 200 and atleast about 70 mole percent of said mixture of amines containing from 16 to 18 carbon atoms.
5. A viscose spinning solution according to claim 11 in which ethylene oxide is used as the alkylene oxide reactant.
6.- A viscose spinning solution according to claim 1 in which ethylene oxide is used as the alkylene oxide reactant.
7. A viscose spinnin solution according to claim 1 in which propylene oxide is used asthe alkylene oxide reactant.
8. A viscose spinning solution having incorpo-;' rated therein between about 0.01 and 0.2%; by weight, of a product formed from the reactionof; between about 12 and 100 moles of ethylene ox" e" with one mole of normal primary octadecylamifie.
9. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of ethylene oxide with one mole of normal primary octa decenylamine. f
10. A viscose spinning solution having incorpoi rated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of ethylene oxide sisting of alkyl and alkenyl amines containing.
from 6 to 18 carbon atoms.
12. A viscose spinning solution having incorpo 30 rated therein between about 0.01 and 0.2%,.by-
weight, of a composition comprising a product formed by the reaction of between about 12' and 100 moles of an alkylene oxide with one mole of a 10 primary aliphatic amine selected from the group consisting of alkyl and alkenyl amines containing from 12 to 18 carbons atoms.
13. A viscose spinning solution having incorporated therein between about 0.01 and 0.2%, by weight, of a product formed from the reaction of between about 12 and 100 moles of an alkylene oxide with one mean mole of a mixture of primary aliphatic amines selected from the group consisting of alkyl and alkenyl amines containing from 6 to 18 carbon atoms; said mixture of amines having a mean molecular weight of at least about 185.
ROBERT D. MACLAURIN. WILLIAM O. ISRAEL.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS- Number Name Date 2,226,119 De Groote Dec. 24, 1940 2,310,207 Bley Feb. 9, 1943 2,362,217 Schlosser et a1 Nov. 7, 1944 2,440,094 Israel Apr. 20, 1948 2,442,331 Cresswell June 1, 1948 FOREIGN PATENTS Number Country Date 358,114 Great Britain Oct. 5, 1931 789,522 France Oct. 30, 1935 665,359 Germany Sept. 23, 1938

Claims (1)

1. A VISCOSE SPINNING SOLUTION HAVING INCORPORATED THEREIN BETWEEN ABOUT 0.01 AND 0.2%, BY WEIGHT, OF A PRODUCT FORMED BY THE REACTION OF AT LEAST ABOUT 12 MOLES OF AN ALKYLENE OXIDE WITH ONE MEAN MOLE OF A MIXTURE OF PRIMARY ALIPHATIC AMINES SELECTED FROM THE GROUP CONSISTING OF ALKYL AND ALKENYL AMINES CONTAINING FROM 6 TO 18 CARBON ATOMS; AT LEAST ABOUT 80 MOLE PERCENT OF SAID MIXTURE OF AMINES CONTAINING FROM 12 TO 18 CARBON ATOMS.
US39194A 1948-07-16 1948-07-16 Viscose spinning solution Expired - Lifetime US2593466A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US39194A US2593466A (en) 1948-07-16 1948-07-16 Viscose spinning solution

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US39194A US2593466A (en) 1948-07-16 1948-07-16 Viscose spinning solution

Publications (1)

Publication Number Publication Date
US2593466A true US2593466A (en) 1952-04-22

Family

ID=21904168

Family Applications (1)

Application Number Title Priority Date Filing Date
US39194A Expired - Lifetime US2593466A (en) 1948-07-16 1948-07-16 Viscose spinning solution

Country Status (1)

Country Link
US (1) US2593466A (en)

Cited By (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2840449A (en) * 1955-06-29 1958-06-24 American Viscose Corp Method of producing all skin rayon
US2840448A (en) * 1955-06-29 1958-06-24 American Viscose Corp Method of producing all skin rayon
US2841462A (en) * 1955-06-29 1958-07-01 American Viscose Corp Production of all skin rayon
US2841463A (en) * 1955-06-29 1958-07-01 American Viscose Corp Process of producing all skin rayon
DE1033371B (en) * 1955-08-18 1958-07-03 Courtaulds Inc Process for the production of hydrate cellulose threads or fibers
US2845327A (en) * 1954-11-03 1958-07-29 American Viscose Corp Method of producing viscose rayon
US2847272A (en) * 1953-06-25 1958-08-12 Courtaulds Ltd Production of artificial filaments, threads and the like
US2849274A (en) * 1954-11-03 1958-08-26 American Viscose Corp Producing all skin viscose rayon
US2852334A (en) * 1954-11-03 1958-09-16 American Viscose Corp Method of producing viscose rayon
US2852333A (en) * 1954-05-21 1958-09-16 Du Pont Viscose spinning process
US2853360A (en) * 1954-11-03 1958-09-23 American Viscose Corp Viscose spinning process
US2855321A (en) * 1955-03-30 1958-10-07 Du Pont Viscose process
US2875078A (en) * 1955-08-22 1959-02-24 Atlas Powder Co Spinning of viscose
US2876124A (en) * 1955-08-22 1959-03-03 Atlas Powder Co Spinning of viscose
US2888356A (en) * 1954-11-03 1959-05-26 American Viscose Corp All skin viscose rayon
US2890132A (en) * 1954-11-03 1959-06-09 John A Howsmon Producing all skin viscose rayon
US2890131A (en) * 1955-06-29 1959-06-09 American Viscose Corp Method of producing all skin rayon
US2893821A (en) * 1955-09-03 1959-07-07 American Enka Corp Production of yarns of regenerated cellulose having improved properties
US2895787A (en) * 1954-12-30 1959-07-21 American Viscose Corp Process of producing all skin rayon
US2895788A (en) * 1954-12-30 1959-07-21 American Viscose Corp Method of forming all skin viscose rayon
US2898222A (en) * 1956-01-30 1959-08-04 Int Paper Canada Manufacture of regenerated cellulose
US2898182A (en) * 1954-12-30 1959-08-04 American Viscose Corp Method of preparing viscose rayon
US2904446A (en) * 1954-11-03 1959-09-15 American Viscose Corp Process of producing viscose rayon
US2908581A (en) * 1954-11-03 1959-10-13 American Viscose Corp Producing all skin viscose rayon
US2912299A (en) * 1954-09-03 1959-11-10 Chimotex Sa Process of spinning viscose containing thiodiglycol
US2914375A (en) * 1954-05-12 1959-11-24 American Enka Corp Manufacture of viscose thread
US2919203A (en) * 1955-12-05 1959-12-29 American Viscose Corp Producing all skin rayon
US2920973A (en) * 1956-04-23 1960-01-12 American Viscose Corp Preparing viscose rayon
US2923637A (en) * 1954-11-03 1960-02-02 American Viscose Corp Viscose solution
US2926099A (en) * 1955-12-05 1960-02-23 American Viscose Corp Preparing all skin viscose rayon
US2929730A (en) * 1955-12-05 1960-03-22 American Viscose Corp Preparing viscose rayon
US2932578A (en) * 1955-12-05 1960-04-12 American Viscose Corp Method of producing all skin rayon
US2940818A (en) * 1954-11-25 1960-06-14 American Enka Corp Production of shaped objects from viscose
US2941892A (en) * 1955-01-31 1960-06-21 Atlas Powder Co Spinning of viscose
US2953425A (en) * 1954-11-25 1960-09-20 American Enka Corp Production of shaped objects from viscose
US2953426A (en) * 1954-11-25 1960-09-20 American Enka Corp Production of shaped objects from viscose
US2953463A (en) * 1951-06-30 1960-09-20 Monsanto Chemicals Fire-retardant cellulosic compositions and process for producing fire-retardant cellulosic structures therefrom
US2958569A (en) * 1954-10-20 1960-11-01 American Enka Corp Production of threads and other shaped objects from viscose
US2960385A (en) * 1957-10-16 1960-11-15 Du Pont Extruding a ferrocyanide containing viscose into a nickel salt containing bath
US2970883A (en) * 1956-01-16 1961-02-07 American Enka Corp Manufacture of viscose rayon
US2971816A (en) * 1954-11-03 1961-02-14 American Viscose Corp Process of producing viscose rayon
US2971817A (en) * 1955-06-29 1961-02-14 American Viscose Corp Producing all skin rayon
DE1100871B (en) * 1956-08-29 1961-03-02 Glanzstoff Ag Process for the production of high-strength threads by spinning viscose
US2974004A (en) * 1954-11-25 1961-03-07 American Enka Corp Production of shaped objects from viscose
US2975021A (en) * 1954-11-03 1961-03-14 American Viscose Corp Method of producing viscose rayon
US2975019A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2975020A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2976113A (en) * 1954-11-03 1961-03-21 American Viscose Corp Process of producing viscose rayon
US2978292A (en) * 1955-03-18 1961-04-04 American Enka Corp Manufacture of rayon
US2979376A (en) * 1955-06-29 1961-04-11 American Viscose Corp Production of rayon
US2984541A (en) * 1959-04-20 1961-05-16 American Viscose Corp Method of forming all skin viscose rayon
US2989410A (en) * 1955-06-29 1961-06-20 American Viscose Corp All skin viscose rayon and method of preparing same
US2989366A (en) * 1955-06-29 1961-06-20 American Viscose Corp Method of preparing all skin viscose
US2993798A (en) * 1955-09-13 1961-07-25 Spinnfaser Ag Viscose spinning solution containing xanthated lower alcohol
US3016305A (en) * 1956-05-10 1962-01-09 Kunstzijdespinnerij Nyma Nv Manufacture of thick-skinned or allskin shaped articles from viscose
US3026170A (en) * 1957-11-29 1962-03-20 American Enka Corp Manufacture of viscose rayon
US3031320A (en) * 1955-08-22 1962-04-24 Atlas Chem Ind Spinning of viscose
DE1132684B (en) * 1955-06-13 1962-07-05 Onderzoekings Inst Res Process for the production of structures such as threads, fibers or films by shaping viscose
US3049398A (en) * 1955-12-05 1962-08-14 American Viscose Corp Method of producing all skin rayon
US3077375A (en) * 1955-08-22 1963-02-12 Atlas Chem Ind Spinning of viscose
US3106444A (en) * 1955-12-05 1963-10-08 Fmc Corp Method of producing all skin rayon
US3116354A (en) * 1957-05-02 1963-12-31 Beaunit Corp Viscose spinning process
US3116352A (en) * 1957-05-02 1963-12-31 Beaunit Corp Viscose spinning
US3116353A (en) * 1957-05-02 1963-12-31 Beaunit Corp Spinning viscose
US3232779A (en) * 1955-01-20 1966-02-01 Mo Och Domsjoe Ab Methods of producing regenerated cellulose
US3298962A (en) * 1960-12-29 1967-01-17 Gen Aniline & Film Corp Spin bath additives
DE1238611B (en) * 1962-09-25 1967-04-13 Hoechst Ag Amines as viscose modifiers
US3355448A (en) * 1964-09-10 1967-11-28 Weyerhaeuser Co Method of improving viscose filtration by the addition of a surface active agent

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE665359C (en) *
GB358114A (en) * 1930-07-05 1931-10-05 Ig Farbenindustrie Ag Process for the manufacture of hydroxyalkylamines
FR789522A (en) * 1934-04-19 1935-10-30 Ig Farbenindustrie Ag Process for the production of wetting agents, detergents, dispersants, levelers, softeners and the like
US2226119A (en) * 1940-03-06 1940-12-24 Petrolite Corp Flooding process for recovering oil from subterranean oil-bearing strata
US2310207A (en) * 1938-10-07 1943-02-09 North American Rayon Corp Surface-active incrustation inhibitor
US2362217A (en) * 1943-01-13 1944-11-07 Rayonier Inc Production of cellulosic products
US2440094A (en) * 1943-07-12 1948-04-20 Ind Rayon Corp Spinning solution and a process of making it
US2442331A (en) * 1940-03-07 1948-06-01 North American Rayon Corp Process of producing rayon

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE665359C (en) *
GB358114A (en) * 1930-07-05 1931-10-05 Ig Farbenindustrie Ag Process for the manufacture of hydroxyalkylamines
FR789522A (en) * 1934-04-19 1935-10-30 Ig Farbenindustrie Ag Process for the production of wetting agents, detergents, dispersants, levelers, softeners and the like
US2310207A (en) * 1938-10-07 1943-02-09 North American Rayon Corp Surface-active incrustation inhibitor
US2226119A (en) * 1940-03-06 1940-12-24 Petrolite Corp Flooding process for recovering oil from subterranean oil-bearing strata
US2442331A (en) * 1940-03-07 1948-06-01 North American Rayon Corp Process of producing rayon
US2362217A (en) * 1943-01-13 1944-11-07 Rayonier Inc Production of cellulosic products
US2440094A (en) * 1943-07-12 1948-04-20 Ind Rayon Corp Spinning solution and a process of making it

Cited By (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2953463A (en) * 1951-06-30 1960-09-20 Monsanto Chemicals Fire-retardant cellulosic compositions and process for producing fire-retardant cellulosic structures therefrom
US2847272A (en) * 1953-06-25 1958-08-12 Courtaulds Ltd Production of artificial filaments, threads and the like
US2914375A (en) * 1954-05-12 1959-11-24 American Enka Corp Manufacture of viscose thread
US2852333A (en) * 1954-05-21 1958-09-16 Du Pont Viscose spinning process
US2912299A (en) * 1954-09-03 1959-11-10 Chimotex Sa Process of spinning viscose containing thiodiglycol
US2958569A (en) * 1954-10-20 1960-11-01 American Enka Corp Production of threads and other shaped objects from viscose
US2852334A (en) * 1954-11-03 1958-09-16 American Viscose Corp Method of producing viscose rayon
US2849274A (en) * 1954-11-03 1958-08-26 American Viscose Corp Producing all skin viscose rayon
US2908581A (en) * 1954-11-03 1959-10-13 American Viscose Corp Producing all skin viscose rayon
US2845327A (en) * 1954-11-03 1958-07-29 American Viscose Corp Method of producing viscose rayon
US2853360A (en) * 1954-11-03 1958-09-23 American Viscose Corp Viscose spinning process
US2904446A (en) * 1954-11-03 1959-09-15 American Viscose Corp Process of producing viscose rayon
US2975020A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2975019A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2888356A (en) * 1954-11-03 1959-05-26 American Viscose Corp All skin viscose rayon
US2890132A (en) * 1954-11-03 1959-06-09 John A Howsmon Producing all skin viscose rayon
US2975021A (en) * 1954-11-03 1961-03-14 American Viscose Corp Method of producing viscose rayon
US2923637A (en) * 1954-11-03 1960-02-02 American Viscose Corp Viscose solution
US2971816A (en) * 1954-11-03 1961-02-14 American Viscose Corp Process of producing viscose rayon
US2976113A (en) * 1954-11-03 1961-03-21 American Viscose Corp Process of producing viscose rayon
US2953426A (en) * 1954-11-25 1960-09-20 American Enka Corp Production of shaped objects from viscose
US2974004A (en) * 1954-11-25 1961-03-07 American Enka Corp Production of shaped objects from viscose
US2953425A (en) * 1954-11-25 1960-09-20 American Enka Corp Production of shaped objects from viscose
US2940818A (en) * 1954-11-25 1960-06-14 American Enka Corp Production of shaped objects from viscose
US2895788A (en) * 1954-12-30 1959-07-21 American Viscose Corp Method of forming all skin viscose rayon
US2898182A (en) * 1954-12-30 1959-08-04 American Viscose Corp Method of preparing viscose rayon
US2895787A (en) * 1954-12-30 1959-07-21 American Viscose Corp Process of producing all skin rayon
US3232779A (en) * 1955-01-20 1966-02-01 Mo Och Domsjoe Ab Methods of producing regenerated cellulose
US2941892A (en) * 1955-01-31 1960-06-21 Atlas Powder Co Spinning of viscose
US2978292A (en) * 1955-03-18 1961-04-04 American Enka Corp Manufacture of rayon
US2855321A (en) * 1955-03-30 1958-10-07 Du Pont Viscose process
DE1132684B (en) * 1955-06-13 1962-07-05 Onderzoekings Inst Res Process for the production of structures such as threads, fibers or films by shaping viscose
US2890131A (en) * 1955-06-29 1959-06-09 American Viscose Corp Method of producing all skin rayon
US2840449A (en) * 1955-06-29 1958-06-24 American Viscose Corp Method of producing all skin rayon
US2840448A (en) * 1955-06-29 1958-06-24 American Viscose Corp Method of producing all skin rayon
US2841462A (en) * 1955-06-29 1958-07-01 American Viscose Corp Production of all skin rayon
US2989366A (en) * 1955-06-29 1961-06-20 American Viscose Corp Method of preparing all skin viscose
US2989410A (en) * 1955-06-29 1961-06-20 American Viscose Corp All skin viscose rayon and method of preparing same
US2979376A (en) * 1955-06-29 1961-04-11 American Viscose Corp Production of rayon
US2841463A (en) * 1955-06-29 1958-07-01 American Viscose Corp Process of producing all skin rayon
US2971817A (en) * 1955-06-29 1961-02-14 American Viscose Corp Producing all skin rayon
DE1033371B (en) * 1955-08-18 1958-07-03 Courtaulds Inc Process for the production of hydrate cellulose threads or fibers
US3077375A (en) * 1955-08-22 1963-02-12 Atlas Chem Ind Spinning of viscose
US3031320A (en) * 1955-08-22 1962-04-24 Atlas Chem Ind Spinning of viscose
US2876124A (en) * 1955-08-22 1959-03-03 Atlas Powder Co Spinning of viscose
US2875078A (en) * 1955-08-22 1959-02-24 Atlas Powder Co Spinning of viscose
US2893821A (en) * 1955-09-03 1959-07-07 American Enka Corp Production of yarns of regenerated cellulose having improved properties
US2993798A (en) * 1955-09-13 1961-07-25 Spinnfaser Ag Viscose spinning solution containing xanthated lower alcohol
US3106444A (en) * 1955-12-05 1963-10-08 Fmc Corp Method of producing all skin rayon
US2932578A (en) * 1955-12-05 1960-04-12 American Viscose Corp Method of producing all skin rayon
US2919203A (en) * 1955-12-05 1959-12-29 American Viscose Corp Producing all skin rayon
US3049398A (en) * 1955-12-05 1962-08-14 American Viscose Corp Method of producing all skin rayon
US2929730A (en) * 1955-12-05 1960-03-22 American Viscose Corp Preparing viscose rayon
US2926099A (en) * 1955-12-05 1960-02-23 American Viscose Corp Preparing all skin viscose rayon
US2970883A (en) * 1956-01-16 1961-02-07 American Enka Corp Manufacture of viscose rayon
US2898222A (en) * 1956-01-30 1959-08-04 Int Paper Canada Manufacture of regenerated cellulose
US2920973A (en) * 1956-04-23 1960-01-12 American Viscose Corp Preparing viscose rayon
US3016305A (en) * 1956-05-10 1962-01-09 Kunstzijdespinnerij Nyma Nv Manufacture of thick-skinned or allskin shaped articles from viscose
US3002803A (en) * 1956-08-29 1961-10-03 American Enka Corp Method of spinning low elongation viscose rayon
DE1100871B (en) * 1956-08-29 1961-03-02 Glanzstoff Ag Process for the production of high-strength threads by spinning viscose
US3116354A (en) * 1957-05-02 1963-12-31 Beaunit Corp Viscose spinning process
US3116352A (en) * 1957-05-02 1963-12-31 Beaunit Corp Viscose spinning
US3116353A (en) * 1957-05-02 1963-12-31 Beaunit Corp Spinning viscose
US2960385A (en) * 1957-10-16 1960-11-15 Du Pont Extruding a ferrocyanide containing viscose into a nickel salt containing bath
US3026170A (en) * 1957-11-29 1962-03-20 American Enka Corp Manufacture of viscose rayon
US2984541A (en) * 1959-04-20 1961-05-16 American Viscose Corp Method of forming all skin viscose rayon
US3298962A (en) * 1960-12-29 1967-01-17 Gen Aniline & Film Corp Spin bath additives
DE1238611B (en) * 1962-09-25 1967-04-13 Hoechst Ag Amines as viscose modifiers
US3355448A (en) * 1964-09-10 1967-11-28 Weyerhaeuser Co Method of improving viscose filtration by the addition of a surface active agent

Similar Documents

Publication Publication Date Title
US2593466A (en) Viscose spinning solution
US2134825A (en) Chemical process
US2674619A (en) Polyoxyalkylene compounds
US2362217A (en) Production of cellulosic products
GB2131436A (en) Process for the alkali dissolution of cellulose carbamate
US2481693A (en) Raw cotton for conversion into rayon
US2572217A (en) Manufacture of viscose rayon
US2572039A (en) Manufacture of cellulose ethers
US2958665A (en) Non-ionic surface-active gel compositions and preparation thereof
US2349797A (en) Alkali-soluble carboxyethyl cellulose ether
US2680737A (en) Alkali cellulose preparation
US3066032A (en) Method of making fibers of regenerated cellulose of improved dyeing properties
US2331936A (en) Method of improving the processing of refined chemical pulp into viscose by adding cation active agents
US2432127A (en) Method of improving the processing of refined chemical pulp into viscose
US2841579A (en) Depolymerization of cellulose in alkaline medium
US2680738A (en) Preparation of alkali cellulose
US2231927A (en) Manufacture of artificial structrues and other useful articles from cellulose derivatives
US2767170A (en) Preparation of alkali cellulose
US2423469A (en) Chemically prepared wood pulp product and process for producing the same
US2341509A (en) Viscose solution
GB685843A (en) Improved cellulosic product
US1938360A (en) Manufacture of alkyl ethers of cellulose
US2236523A (en) Cellulose ethers
US2313866A (en) Manufacture of cellulose ethers
EP1040214B1 (en) Auxiliary agent for the production of cellulose fibers