US3146116A - Cyanoethylation and xanthation of alkali cellulose - Google Patents
Cyanoethylation and xanthation of alkali cellulose Download PDFInfo
- Publication number
- US3146116A US3146116A US59191A US5919160A US3146116A US 3146116 A US3146116 A US 3146116A US 59191 A US59191 A US 59191A US 5919160 A US5919160 A US 5919160A US 3146116 A US3146116 A US 3146116A
- Authority
- US
- United States
- Prior art keywords
- viscose
- cellulose
- acrylonitrile
- alkali
- carbon bisulfide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920002678 cellulose Polymers 0.000 title claims description 39
- 239000001913 cellulose Substances 0.000 title claims description 39
- 239000003513 alkali Substances 0.000 title claims description 19
- 238000007278 cyanoethylation reaction Methods 0.000 title description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 45
- 229920000297 Rayon Polymers 0.000 claims description 40
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 5
- 230000001172 regenerating effect Effects 0.000 claims description 5
- 239000000835 fiber Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002932 luster Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000012991 xanthate Substances 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B13/00—Preparation of cellulose ether-esters
- C08B13/02—Cellulose ether xanthates
-
- 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
Definitions
- This invention relates to a process for producing a modified viscose having improved properties. More particularly it relates to the simultaneous cyanoethylation and xanthantion of alkali cellulose.
- cyanoethylating cellulose involves treating an alkaline suspension of cellulose with acrylonitrile dissolved in the alkaline solution. This procedure uses comparatively large amounts of acrylonitrile and results in waste liquors which must be subjected to recovery treatments to reduce acrylonitrile and alkali losses. Viscose has been cyanoethylated by adding acrylonitrile directly to viscose. However, large amounts of acrylonitrile are consumed by the by-product sulfur compounds present in the viscose.
- a modified viscose which comprises reacting alkali cellulose with from 01% to 60%, based on the weight of the cellulose, of acrylonitrile and from 20 to 60% based on the weight of the cellulose, of carbon bisulfide, and dissolving the reacted cellulose in a dilute alkali solution. It is preferred, for a viscose used for spinning hydrophobic fibers, that less than 1% acrylonitrile be used with from 25 to 35% carbon bisulfide.
- the acrylonitrile reacts with the cellulose to form cyanoethylated cellulose; this swells the material and lets the carbon bisulfide in between the cellulose chains so that it reacts or xanthates faster.
- This invention also includes a method of forming shaped cellulosic articles by first preparing a modified viscose as described above, forming the viscose into a shaped article, and then regenerating the viscose to produce the finished article.
- the viscose should be prepared with less than 1% acrylonitrile based on the cellulose. This viscose can be spun into filaments which are stretched to from 25 to 75% of their original length. The stretched ice fibers are then hot water washed in a relaxed state and dried to produce excellent crimped fibers.
- Example I Alkali cellulose is charged as usual into a churn used for xan thation. Carbon bisulfide containing a predetermined amount of acrylonitrile is added to the churn to yield 30% carbon bisulfide and .25% acrylonitrile based on the weight of cellulose in the alkali crumbs. After simultaneously xanthating and cyanoethylating the alkali crumbs for a period of 1 /2 hours, the reacted cellulose is dissolving in dilute sodium hydroxide to form a viscose containing 8.6% cellulose and 6.4% sodium hydroxide.
- This viscose was used to spin 15 denier per filament fibers from a coagulating and regenerating bath containing 7.2% sulfuric acid; 1% Zinc sulfate and 20% sodium sulfate at 50 C. bath temperature, using a spinning speed of meters per minute and a bath immersion of 32 inches. After leaving the bath the filaments in the form of a fiber were stretched 40% of their original length, then relaxed in hot water, where the fibers developed an excellent crimp.
- the extensibility of the finished fiber produced by this method is considerably higher than that produced in a similar manner from viscose prepared from a non-cyanoethylated cellulose xanthate. Other properties such as cross section, water retention and dye affini-ty are also modified.
- Trial viscoses were prepared by reacting alkali cellulose with various mixtures of acrylonitrile and carbon bisul fide where the amounts of the acrylonitrile component varied from 60% down to 076%, based on the weight of the cellulose, and the amount of carbon bisulfide was maintained at 30%.
- Acrylonitrile, even at .076% accelerated the aging of the viscose greatly as determined by the sodium chcloride salt test.
- For higher concentrations of acrylonitrile the strength and extensibility of spun yarn produced therewith is lowered.
- viscose prepared with the smaller percentages of acrylonitrile is preferred.
- a method for preparing a modified viscose which comprises reacting alkali cellulose with a mixture containing from 0.01 to 60% of acrylonitrile and from 20 to 60% of carbon bisulfide, said percentage amounts being based on the weight of the cellulose, and dissolving the reacted cellulose in a dilute aqueous solution of alkali hydroxide.
- a method of forming shaped cellulosic articles which comprises reacting alkali cellulose with a mixture containing from 0.01 to 60% of acrylonitrile and from 20 to 60% of carbon bisulfide, said percentage amounts based on the weight of the cellulose, dissolving the reacted cellulose in dilute alkali to form viscose, forming the viscose into a shaped article, and regenerating the viscose article.
- a method of forming shaped cellulosic articles which comprises reacting alkali cellulose with a mixture containing from 0.01 to 1% of acrylonitrile and from 25 to 35% of carbon bisulfide, said percentage amounts based on the weight of the cellulose, dissolving the reacted cellulose in dilute alkali to form viscose, forming the viscose into a 15 shaped article, and regenerating the viscose article.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
United States Patent 3,146,116 CYANOETHYLATION AND XANTHATION OF ALKALI CELLULOSE Arthur I. Bates, Wilmington, Del., assignor, by mesne assignments, to FMC Corporation, San Jose, Calif., a
corporation of Delaware No Drawing. Filed Sept. 29, 1960, Ser. No. 59,191 7 Claims. (Cl. 106-165) This invention relates to a process for producing a modified viscose having improved properties. More particularly it relates to the simultaneous cyanoethylation and xanthantion of alkali cellulose.
The usual method for cyanoethylating cellulose involves treating an alkaline suspension of cellulose with acrylonitrile dissolved in the alkaline solution. This procedure uses comparatively large amounts of acrylonitrile and results in waste liquors which must be subjected to recovery treatments to reduce acrylonitrile and alkali losses. Viscose has been cyanoethylated by adding acrylonitrile directly to viscose. However, large amounts of acrylonitrile are consumed by the by-product sulfur compounds present in the viscose.
It is an object of this invention to provide a viscose material having an accelerated aging rate.
It is another object of this invention to provide cyanoethylated viscose produced with less acrylonitrile than that previously produced.
It is a further object of this invention to provide a method for cyanoethylating alkali cellulose which uses less acrylonitrile and eliminates the necessity for recovery treatments of Waste liquors.
It is still another object of this invention to provide a method for the production of cellulose articles having improved properties such as luster and clarity.
It is a still further object of this invention to provide a method for the production of cellulose fibers having improved extensibility and a smoother cross section, together with increased dye affinity.
It is a still further object of this invention to provide soluble regenerated viscose fibers with considerable reduction in the amount of carbon bisulfide used for xanthating.
These and other objects are accomplished in accordance with the present invention which broadly includes a method for preparing a modified viscose which comprises reacting alkali cellulose with from 01% to 60%, based on the weight of the cellulose, of acrylonitrile and from 20 to 60% based on the weight of the cellulose, of carbon bisulfide, and dissolving the reacted cellulose in a dilute alkali solution. It is preferred, for a viscose used for spinning hydrophobic fibers, that less than 1% acrylonitrile be used with from 25 to 35% carbon bisulfide. However, for a process wherein the amount of carbon bisulfide used for xanthating the alkali cellulose is advantageously reduced, large amounts of acrylonitrile, up to about 60%, can be used to replace much of the carbon bisulfide. Regenerated articles formed from viscose prepared with large amounts of acrylonitrile are highly water-soluble.
It is theorized that the acrylonitrile reacts with the cellulose to form cyanoethylated cellulose; this swells the material and lets the carbon bisulfide in between the cellulose chains so that it reacts or xanthates faster.
This invention also includes a method of forming shaped cellulosic articles by first preparing a modified viscose as described above, forming the viscose into a shaped article, and then regenerating the viscose to produce the finished article. In the formation of cellulosic fibers from the cyanoethylated viscose, the viscose should be prepared with less than 1% acrylonitrile based on the cellulose. This viscose can be spun into filaments which are stretched to from 25 to 75% of their original length. The stretched ice fibers are then hot water washed in a relaxed state and dried to produce excellent crimped fibers.
The following is an example demonstrating the method of preparing a modified viscose and the method of producing fibers from the viscose.
Example I Alkali cellulose is charged as usual into a churn used for xan thation. Carbon bisulfide containing a predetermined amount of acrylonitrile is added to the churn to yield 30% carbon bisulfide and .25% acrylonitrile based on the weight of cellulose in the alkali crumbs. After simultaneously xanthating and cyanoethylating the alkali crumbs for a period of 1 /2 hours, the reacted cellulose is dissolving in dilute sodium hydroxide to form a viscose containing 8.6% cellulose and 6.4% sodium hydroxide.
This viscose was used to spin 15 denier per filament fibers from a coagulating and regenerating bath containing 7.2% sulfuric acid; 1% Zinc sulfate and 20% sodium sulfate at 50 C. bath temperature, using a spinning speed of meters per minute and a bath immersion of 32 inches. After leaving the bath the filaments in the form of a fiber were stretched 40% of their original length, then relaxed in hot water, where the fibers developed an excellent crimp. The extensibility of the finished fiber produced by this method is considerably higher than that produced in a similar manner from viscose prepared from a non-cyanoethylated cellulose xanthate. Other properties such as cross section, water retention and dye affini-ty are also modified.
A modified viscose produced in the same manner as described above but aged for 48 hours produced a fiber having a still better crimp and improved luster. Generally fibers produced with the modified viscose had a firmer hand, better crimp, more luster and a less milky appearance than fiber spun with conventional viscose. The improved fiber also had greater soil resistance and its crush recovery was almost 10% greater than the conventional fiber.
Example II A viscose solution was prepared by reacting alkali cellulose prepared as described in Example I with 24%, based on the weight of the cellulose, of carbon bisulfide and 60%, based on the weight of cellulose, of acrylonitrile. A yarn was spun from this viscose which swelled greatly in water.
Trial viscoses were prepared by reacting alkali cellulose with various mixtures of acrylonitrile and carbon bisul fide where the amounts of the acrylonitrile component varied from 60% down to 076%, based on the weight of the cellulose, and the amount of carbon bisulfide was maintained at 30%. Acrylonitrile, even at .076% accelerated the aging of the viscose greatly as determined by the sodium chcloride salt test. For higher concentrations of acrylonitrile the strength and extensibility of spun yarn produced therewith is lowered. Thus, for carpet fibers and the like, viscose prepared with the smaller percentages of acrylonitrile is preferred.
Various changes and modifications may be made in practicing the invention without departing from the spirit and scope thereof and, therefore, the invention is not to be limited except as defined in the appended claims.
I claim:
1. A method for preparing a modified viscose which comprises reacting alkali cellulose with a mixture containing from 0.01 to 60% of acrylonitrile and from 20 to 60% of carbon bisulfide, said percentage amounts being based on the weight of the cellulose, and dissolving the reacted cellulose in a dilute aqueous solution of alkali hydroxide.
2. The method of claim 1 wherein less than 1% acrylonitrile is used.
3. The method of claim 1 wherein over 1% acrylonitrile is used.
4. A method of forming shaped cellulosic articles which comprises reacting alkali cellulose with a mixture containing from 0.01 to 60% of acrylonitrile and from 20 to 60% of carbon bisulfide, said percentage amounts based on the weight of the cellulose, dissolving the reacted cellulose in dilute alkali to form viscose, forming the viscose into a shaped article, and regenerating the viscose article.
5. A method of forming shaped cellulosic articles which comprises reacting alkali cellulose with a mixture containing from 0.01 to 1% of acrylonitrile and from 25 to 35% of carbon bisulfide, said percentage amounts based on the weight of the cellulose, dissolving the reacted cellulose in dilute alkali to form viscose, forming the viscose into a 15 shaped article, and regenerating the viscose article.
5 relaxed in hot water and dried.
References Cited in the file of this patent UNITED STATES PATENTS Lilienfeld Feb. 16, 1943 Houtz May 15, 1945 OTHER REFERENCES Somers: British Rayon and Silk Journal, volume 26, No. 312, May 1950, page 62.
MacGregor: J. Soc. Dyers and Colorists, vol. 67 (1951), page 68.
Disclaimer 3,146,116.-Art7m1- I Bel ates, Wilmington, Del. CYANOETHYLATION AND XANTHATION OF ALKALI CELLULOSE. Patent dated Aug. 25, 1964. Disclaimer filed May 22, 1969, by the assignee FM 0 001790- ratio n. Hereby enters this disclaimer to claims 1, 3 and l of said patent.
[Ofieial Gazette December 30, 1.969.]
Claims (1)
- 5. A METHOD OF FORMING SHAPED CELLULOSIC ARTICLES WHICH COMPRISES REACTING ALKALI CELLULOSE WITH A MIXTURE CONTAINING FROM 0.01 TO 1% OF ACRYLONITRILE AND FROM 25 TO 35% OF CARBON BISULFIDE, SAID PERCENTAGE AMOUNTS BASED ON THE WEIGHT OF THE CELLULOSE, DISSOLVING THE REACTED CELLULOSE IN DILUTE ALKALI TO FORM VISCOSE, FORMING THE VISCOSE INTO A SHAPED ARTICLE, AND REGENERATING THE VISCOSE ARTICLE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59191A US3146116A (en) | 1960-09-29 | 1960-09-29 | Cyanoethylation and xanthation of alkali cellulose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59191A US3146116A (en) | 1960-09-29 | 1960-09-29 | Cyanoethylation and xanthation of alkali cellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3146116A true US3146116A (en) | 1964-08-25 |
Family
ID=22021387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US59191A Expired - Lifetime US3146116A (en) | 1960-09-29 | 1960-09-29 | Cyanoethylation and xanthation of alkali cellulose |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3146116A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359155A (en) * | 1963-10-28 | 1967-12-19 | Kurashiki Rayon Co | Process for preparing a viscose spinning solution, fibers formed therefrom and paper containing said fibers |
| US3399069A (en) * | 1962-06-07 | 1968-08-27 | Tee Pak Inc | Spray dried polymeric alcohol xanthates |
| US3419345A (en) * | 1961-10-27 | 1968-12-31 | Du Pont | Neutralization of hydrophilic gel fibers of a cellulose derivative |
| US3919385A (en) * | 1972-11-24 | 1975-11-11 | Fmc Corp | Process for producing high fluid-holding fiber mass |
| US3951889A (en) * | 1972-11-24 | 1976-04-20 | Fmc Corporation | Fluid absorbent alloy fibers |
| US4342600A (en) * | 1980-01-05 | 1982-08-03 | Hoechst Aktiengesellschaft | Process for the manufacture of viscoses |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2310969A (en) * | 1939-05-23 | 1943-02-16 | Lilienfeld Patents Inc | Process for the manufacture of shaped structures from solutions of cellulose derivatives |
| US2375847A (en) * | 1942-12-17 | 1945-05-15 | Du Pont | Process for the preparation of cyanoethyl cellulose |
-
1960
- 1960-09-29 US US59191A patent/US3146116A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2310969A (en) * | 1939-05-23 | 1943-02-16 | Lilienfeld Patents Inc | Process for the manufacture of shaped structures from solutions of cellulose derivatives |
| US2375847A (en) * | 1942-12-17 | 1945-05-15 | Du Pont | Process for the preparation of cyanoethyl cellulose |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419345A (en) * | 1961-10-27 | 1968-12-31 | Du Pont | Neutralization of hydrophilic gel fibers of a cellulose derivative |
| US3399069A (en) * | 1962-06-07 | 1968-08-27 | Tee Pak Inc | Spray dried polymeric alcohol xanthates |
| US3359155A (en) * | 1963-10-28 | 1967-12-19 | Kurashiki Rayon Co | Process for preparing a viscose spinning solution, fibers formed therefrom and paper containing said fibers |
| US3919385A (en) * | 1972-11-24 | 1975-11-11 | Fmc Corp | Process for producing high fluid-holding fiber mass |
| US3951889A (en) * | 1972-11-24 | 1976-04-20 | Fmc Corporation | Fluid absorbent alloy fibers |
| US4342600A (en) * | 1980-01-05 | 1982-08-03 | Hoechst Aktiengesellschaft | Process for the manufacture of viscoses |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: NEW ENGLAND MUTUAL LIFE INSURANCE COMPANY 501 BOYL Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: PROVIDENT ALLIANCE LIFE INSURANCE COMPANY C/O THE Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: WESTERN AND SOUTHERN LIFE INSURANCE COMPANY THE C/ Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: WALTER E. HELLER & COMPANY, INC., A CORP. OF DEL. Free format text: AGREEMENT WHEREBY AETNA RELEASES AVTEX FROM ALL MORTAGES AND SECURITY INTERESTS IN SAID INVENTIONS AS OF JANUARY 11,1979, AND ASSIGNS TO ASSIGNEE THE ENTIRE INTEREST IN SAID MORTAGE AGREEMENT TO ASSIGNEE;ASSIGNORS:AETNA BUSINESS CREDIT, INC., A CORP. OF N.Y.;AVTEX FIBERS, INC, A CORP. OF NY;KELLOGG CREDIT CORP., A CORP. OF DEL.;REEL/FRAME:003959/0250 Effective date: 19800326 Owner name: JOHN HANCOCK MUTUAL LIFE INSURANCE COMPANY JOHN HA Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: BALBOA INSURANCE COMPANY C/O THE PAUL REVERE EQUIT Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: PAUL REVERE LIFE INSURANCE COMPANY THE C/O THE PAU Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: KELLOGG CREDIT CORPORATION A DE CORP. Free format text: AGREEMENT WHEREBY SAID HELLER AND RAYONIER RELEASES ALL MORTGAGES AND SECURITY INTERESTS HELD BY AVTEX ON APRIL 28, 1978, AND JAN. 11, 1979, RESPECTIVELY AND ASSIGNS ITS ENTIRE INTEREST IN SAID MORT-AGAGE AGREEMENT TO ASSIGNEE;ASSIGNORS:WALTER E. HELLER & COMPANY, INC. A NY CORP.;ITT RAYONIER INCORPORATED, A DE CORP.;AVTEX FIBERS INC., A NY CORP.;REEL/FRAME:003959/0350 Effective date: 19800326 |