US2143765A - Yarn conditioning process and composition therefor - Google Patents
Yarn conditioning process and composition therefor Download PDFInfo
- Publication number
- US2143765A US2143765A US204374A US20437438A US2143765A US 2143765 A US2143765 A US 2143765A US 204374 A US204374 A US 204374A US 20437438 A US20437438 A US 20437438A US 2143765 A US2143765 A US 2143765A
- Authority
- US
- United States
- Prior art keywords
- yarn
- cellulose
- yarns
- textile
- parts
- 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
- 230000003750 conditioning effect Effects 0.000 title description 32
- 238000000034 method Methods 0.000 title description 13
- 239000000203 mixture Substances 0.000 title description 12
- 239000004753 textile Substances 0.000 description 36
- 238000009940 knitting Methods 0.000 description 30
- -1 organic ester amides Chemical class 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 26
- 238000009987 spinning Methods 0.000 description 21
- 229920002678 cellulose Polymers 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 229920002301 cellulose acetate Polymers 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- 238000009941 weaving Methods 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000001913 cellulose Substances 0.000 description 18
- 230000001050 lubricating effect Effects 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000000314 lubricant Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000009877 rendering Methods 0.000 description 6
- URKPRLOWLUURBJ-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol propanoic acid Chemical compound C(CC)(=O)O.C(CC)(=O)O.C(CC)(=O)O.N(CCO)CCO URKPRLOWLUURBJ-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000010697 neat foot oil Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 3
- 229920006218 cellulose propionate Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SZXIMJCHKWYCHX-UHFFFAOYSA-N 2-aminoethyl propanoate Chemical compound CCC(=O)OCCN SZXIMJCHKWYCHX-UHFFFAOYSA-N 0.000 description 1
- CLKWZQXGKAFADO-UHFFFAOYSA-N C(CC)(=O)O.C(C)(=O)O.C(C)(=O)O.N(CCO)CCO Chemical compound C(CC)(=O)O.C(C)(=O)O.C(C)(=O)O.N(CCO)CCO CLKWZQXGKAFADO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000147568 Laurus nobilis Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- AJWDUWKCBCUZII-UHFFFAOYSA-N acetic acid 2-aminoethanol Chemical compound C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(O)CN AJWDUWKCBCUZII-UHFFFAOYSA-N 0.000 description 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012237 artificial material Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- Y10S516/06—Protein or carboxylic compound containing
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2904—Staple length fiber
- Y10T428/2907—Staple length fiber with coating or impregnation
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2965—Cellulosic
Definitions
- This invention relates to the conditioning of lubricating, softening and rendering such yarns textile yarns and more particularly to the conmore amenable to knitting and other textile ditioning of filaments and yarns composed of operations.
- a furtherand specific object is to organic derivatives of cellulose such as celluprovide a class of conditioning agents which auglose acetate, cellulose propionate, cellulose acement or assist the lubricating action of various 5 tate propionate, and cellulose acetate butyrate, lubricants when applied to such yarns.
- a still to render them more amenable to textile operafurther object is to provide yarn softening and tions such as knitting and the like. lubricating formulas which can be readily re-.
- a still further object is to provide an improved 10 lulose organic derivatives, it is necessary to treat method for the conditioning of yarns, particuthe yarn in order to reduce the tendency toward larly those composed of or containing organic breakage of the individual filaments or fibers derivatives of cellulose such as cellulose acetate,
- Another. object is to provide an necessary to treat yarn to adapt it for use as improved type of yarn which is especially amenwarp or filling or for the manufacture of various able to textile operations including circular knittypes of knitted fabrics. In knitting, it is parting, weaving, spinning and the like. Other obticllldrly important that the yarn be soft and jects will appear hereinafter.
- these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself.
- these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they-may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in I conjunction with agents which function wholly or partially as lubricants.
- This composition is applied to a cellulose acetate 'yarn intended for knitting in an amount representing 4 to 25% by weight of the untreated yarn.
- the filaments or fibers treated as described above are quite soft and. pliable and give excellent resuits in textile operations, especially in circular knitting.
- yarn conditioning compositions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with our invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:
- Example 3 Cilia-C 80 parts 02 Blown olive oil 20 parts
- Example 4 CzH4--O C 00H: GHQ-C ON 20 parts I C;Hr-O-C O-C:Hu 7 Light mineral oil 80 parts
- Example 5 H ⁇ I N-CalEh-O 0 0-013; 20 mm CzlHsC O Blown sperm oil 80 parts
- Example 6 CHg-O OHrC 0'N(C3Ht0COCH2-0 CH1); 40 parts Neats-ioot oil 60 parts 1
- Example 7 Clix-C I I 7 CH: OH-O O-N-(CzH4-O C 0'C Hi): 20 parts CHI-CH1sperm oil 60 parts Laurel 20 parts
- Example 8 C4Hn CHa- C O -N I CH;-CH-CHz-O C 0-0 H; parts (JO-CHa Tetrahydro'furiuryl glycerol acetate 20 parts Blown soy
- cellulose organic acid esters such as cellulose acetate, cellulose propionate, cellulose acetate propionate, cellulose acetate butyrate and the like
- ethanolamine acetate propionate, ethanolamine dibutyrate, ethanolamine propionate-butyrate, and diethanolamine tripropionate we are enabled to produce yarns or filaments having exceptional knitting properties. This is particularly true in the conditioning of yarns for use in circular knitting.
- any of the above compositions may beapplied to yarns intended for use in circular knitting by means of a bath, wick, spray, roller, pad or Example 11
- Example 12 Parts Blown neats-foot oil 20 Ethanolamine propionate butyrate 80
- Example 13 Parts Blown olive oil 10-25 Ethanolamine propionate butyrate -75
- Example 17 Parts Neats-ioot oil 5-50 Ethanolamine propionate butyrate 95-50
- Example 18 Parts Blown neats-foot oil 20 'Ethanolamine dibutyrate 80
- Example 19 I Parts Blown
- condition- 7 As willoe apparent from'the above examples -and: description the: conditioning agents :of our 'ing liquid applied may vary between -25% by" weightof the yarn. Usually, however, the amount of conditioning liquid applied is about -15% by I I weight of the yarn. Yarn composed of cellulose acetate conditioned as described abovegives ex 'celle'nt' results: when used in thecircular knitting process. I
- agent 1 as an ingredient of the spinning dope from whichv vulva the filamentsare formed, the amount ofthe' agent so employed depending upon a number of fac-:
- tors such as the particular cellulose derivative used in making the yarn, thesolvent or solvent I 1 combination used in making upthe spinning so-v lution, and the degree I of softness or pliability desired in the yarn, etc.
- conditioning agent is to be applied to the yarn afterspin'ning, this maybe done by bringing the'yarn in contact with a wick, roll,:'
- the liquid may be applied l ing onto cones, spools, bobbins, or the like or by the SO-Called bobbin to bobbin method.
- the liquid may be applied to the yarn prior to, or after cutting into staple lengths.
- a cellulose Organic acid ester yarn such as a yarn composed of cellulose acetate
- about 4 to 25% or more by weight, based on the weight .of the dry yarn may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.
- compositions containing specific percentages of the various ingredients may vary widely depending upon the particular purpose for which the composition is intended.
- the amount of formulas described herein are applicable to the conditioning of, many other types of cellulose de-; I rivative yarns such as those composed'of or'con- I I taining cellulose propionate, cellulose butyrate,
- ture of natural and artificial filamentsor a composite :threadformed by twisting together individual strands of natural or; artificial :materials, I I I as well as, cut staple fibers produced from nat-' 'ural and/or artificialfilaments 01' threads and,
- R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from thegroup consisting of substituted, and unsubstituted alkyl, aryl and. cycloalkyl; X is CO--; n is l, b is at least 1 and R'X may be hydrogen.
- R is a radical selected from'the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.
- R is a radical selected from the group consisting of alkyl, cycloalkyl'and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl,
- X is CO 11.
- b is at least l and RX may be hydrogen, and textile lubricant.
- a conditioning agent for rendering y'arns more amenable to textile operations includin knitting, weaving, spinning and the like which comprises an organic ester amide having the general formula:
- R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl;
- X is CO; n is 1, b is at least 1 and RX may be hydrogen.
- R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; 11 is 1, b is at least 1 and RX may be hydrogen and a textile lubricating oil.
- R is a radical selected from the group consisting ofallwl, cycloalkyl and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.
- Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:
- RX is a radical selected from the group -consisting of alkyl, cycloalkyl and aryl; Rf and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is l, b is at least 1 and RX may be hydrogen.
- Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:
- Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine acetate propionate.
- Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine propionate butyrate.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Patented Jan. 10, 1939 v 2,143,765
YARN CONDITIONING PROCESS AND COM- POSITION THEREFOR Joseph B. Dickey and James G. McNally, Roch'ester, N. Y., assignors to Eastman Kodak Comgany, Rochester, N. Y., a corporation of New ersey No Drawing. Application April 26, 1938, Serial No..204,374
. 18 Claims. (Cl. 28-1) This invention relates to the conditioning of lubricating, softening and rendering such yarns textile yarns and more particularly to the conmore amenable to knitting and other textile ditioning of filaments and yarns composed of operations. A furtherand specific object is to organic derivatives of cellulose such as celluprovide a class of conditioning agents which auglose acetate, cellulose propionate, cellulose acement or assist the lubricating action of various 5 tate propionate, and cellulose acetate butyrate, lubricants when applied to such yarns. A still to render them more amenable to textile operafurther object is to provide yarn softening and tions such as knitting and the like. lubricating formulas which can be readily re-.
As is well known in the manufacture of yarns, moved from the yarns by the usual scour baths.
particularly those composed of or containing cel- A still further object is to provide an improved 10 lulose organic derivatives, it is necessary to treat method for the conditioning of yarns, particuthe yarn in order to reduce the tendency toward larly those composed of or containing organic breakage of the individual filaments or fibers derivatives of cellulose such as cellulose acetate,
a when they are subjected to various mechanical whereby the yarn is rendered soft and pliable and strains and to lubricate the yarn in order to capable of employment in a variety of textile V facilitate handling in such operations as spinoperations where complicated designs or stitches ning, twisting, winding. and reeling. It is also are employed. Another. object is to provide an necessary to treat yarn to adapt it for use as improved type of yarn which is especially amenwarp or filling or for the manufacture of various able to textile operations including circular knittypes of knitted fabrics. In knitting, it is parting, weaving, spinning and the like. Other obticllldrly important that the yarn be soft and jects will appear hereinafter. pliable in order that it may conform readily to These objects are accomplished by the followthe contour of the needles and thus produce a ing invention which, in its broader aspects, comclosely knit fabric free from such defects as prises thedis'covery that organic ester amides stitch distortion, pin holes, laddering," and having the general formula: 25
the like. I (Rlx) N (R) OC RH I I Heretofore it has been proposed to employ g softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditionwhere R is al y cycloalkyl y d ing or lubricating formulas, generally in conare the same or diiferent substituted or unsub- 3o nection with mineral, animal or vegetable oils. Stitllted alkyl, y y a lf p- X 19 It has been found, however, that most of the O-; 12 is 1, bis 1 or more and RX may stand known softening agents and the various formulas for hydrogen, may be used as yarn conditioning containing them have certain drawbacks, one of c agents d pa u rly as softening, a t
the most serious of which is high vapor pressure, with or without the addition of animal, mineral, 35
and in some cases too drastic a solvent action on Vegetable O in t a e t of y ns the yarn. Many of such agents possess slight posed of or containing organic derivatives of or insuificient solvent power for the lubricants cellulose We hav f und that th s compounds with which they are used, and it is accordingly w mp oyed as de r d in t detailed fying agents in order to obtain operable yarn nd/or softening acti n on c llulose r n treating formulas. In addition, many ofth rivative yarns which renders such yarns soft and known softening and lubricating agents are inpliable without at the same time having too sufliciently soluble in water to permit satisfacd c an action thereon tory removal by aqueous scour baths. Typical examples of compounds which, inac- 45 This invention has as its principal object to cordance with our invention, we have found to provide an entirely new class of yarn conditionbe valuable yarn-treating agents are given in ing agents which are particularly adapted for the following table. These compounds which the treatment of yarns composed of or containing may, as indicated above, be considered ester organic derivatives of cellulose and capable OI amides, or more specifically as N,N-di(acyloxy- 50 necessary to employ blending agents or emul iamples set forth below have a slight solvent 40 E alkyl) amides, are derived by reaction on alkylol amines of appropriate acids or anhydrides.
turned to the reaction vessel. The distillation is stopped when 54 parts of water have been 001- Ester amides derivable from monoethanolamine Dimethoxy acetate Ester amides derivable from diethanolamine Compound Formula Boiling range Millimeters 'Iriacetate; CHaCO-N-(CgH OGOCH3); 212-2l4 /23 Diaocetete proplo- C:HCON(C:H OCOCH3)1 220-"225 [23 us a.
'lributyrate C H1CO-N-C2H4OCOCaH1): 220222 l2 2H4OCOCzH5 Acetate proplonate CHaCO-N 240260 I24 butyrate.
CH OCOCaH1J (331E140COCsHL Acetate butyrate CHaO0-N 232-240" caproate.
- CQH4OCOCISH11 Dlbugyrata propi- CzHaCO-N-(Czl-IQOCOCaHfl: 222-230" [23 one e.
Ditproxtlionete bu- C3H1CON-(CaH OCOOH )z 218-225 I22 4 yra e. Tricaproate; 235-245 /2 CzsHuC N- ZH4O 0005 11):
Examples of the preparation of typical compounds of this type are as follows:
Preparation of diethanolamine diacetate propionate cine-000cm CHaC ON C2H4'OCOC2H5' are obtained, boiling at 215-220/23 mm.
Preparation of ethanolamine triacetate Seven equivalents of acetyl chloride are added slowly to two equivalents of ethanolamine. The solution is then refluxed on the water bath until no more hydrogen chloride is given off. The product is then worked up in the usual way; A good yield of the triacetyl derivative is obtained, B. P. 165170/18 mmr Preparation of dietha'nolamine tricaproate One hundred and five parts of diethanolamine, 350 parts caproic acid, 5 parts concentrated sulfuric acid and 100 parts toluene are distilled in such a manner that the toluene is continuously separated from the water of reaction and re-' lected. The catalyst is then neutralized by washing with sodium carbonate solution and the product recovered by distillation. Three hundred and seventy-five parts of the tri-caproyl derivative are obtained, B. P. 235245/5 mm.
Preparation of ethanolamine propionate butyrate Sixty one grams of ethanolamine, 130 grams of propionic anhydride and 160 grams of butyric anhydride are heated under reflux until the reaction is completed. The propionic and butyric acids formed in the reaction are distilled off and the ester-amide is distilled under reducedpressure. The compound'is a colorless liquid and boils at 158-161/11 mm.
In accordance with 'the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. We have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they-may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in I conjunction with agents which function wholly or partially as lubricants.
In the following examples and description we have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof,
Ourinventlon will be more readily understood by reference to the following examples in which typical applications of the invention are set forth.
This composition is applied to a cellulose acetate 'yarn intended for knitting in an amount representing 4 to 25% by weight of the untreated yarn. The filaments or fibers treated as described above are quite soft and. pliable and give excellent resuits in textile operations, especially in circular knitting.
Other examples of yarn conditioning compositions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with our invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:
Example 3 Cilia-C 80 parts 02 Blown olive oil 20 parts Example 4 CzH4--O C 00H: GHQ-C ON 20 parts I C;Hr-O-C O-C:Hu 7 Light mineral oil 80 parts Example 5 H\ I N-CalEh-O 0 0-013; 20 mm CzlHsC O Blown sperm oil 80 parts Example 6 CHg-O OHrC 0'N(C3Ht0COCH2-0 CH1); 40 parts Neats-ioot oil 60 parts 1 Example 7 Clix-C I I 7 CH: OH-O O-N-(CzH4-O C 0'C Hi): 20 parts CHI-CH1 Sperm oil 60 parts Laurel 20 parts Example 8 C4Hn CHa- C O -N I CH;-CH-CHz-O C 0-0 H; parts (JO-CHa Tetrahydro'furiuryl glycerol acetate 20 parts Blown soya bean oil 80 parts Example 9 Water 80 parts O=CH0-N 10 parts 0 1140 C OC3Ha Water soluble cellulose ester, 5 parts Glymrol acetone 5 parts Example 10 solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate, of
is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wound or twisted and wound. 'Yarns thus produced are pliable-and suitable for knitting.
For the purpose of conditioning yarns composed of or containing various cellulose derivatives, par-- ticularly the cellulose organic acid esters such as cellulose acetate, cellulose propionate, cellulose acetate propionate, cellulose acetate butyrate and the like, we have found ethanolamine acetate propionate, ethanolamine dibutyrate, ethanolamine propionate-butyrate, and diethanolamine tripropionate to be outstandingly 'efiective. By the use of these compounds we are enabled to produce yarns or filaments having exceptional knitting properties. This is particularly true in the conditioning of yarns for use in circular knitting.
Conditioning liquids which we have found to.
be of particular value in preparing cellulose ester yarns for circular knitting are the following:
Any of the above compositions may beapplied to yarns intended for use in circular knitting by means of a bath, wick, spray, roller, pad or Example 11 I Parts Blown neats-foot oil 15 Ethanolamine propionate'butyrate Example 12 Parts Blown neats-foot oil 20 Ethanolamine propionate butyrate 80 Example 13 Parts Blown olive oil 10-25 Ethanolamine propionate butyrate -75 Example 14 Parts Blown sperm oil -50 Ethanolamine propionate butyrate 5-50 Example 15 t Parts Blown teaseed oil 53-50 Ethanolamine propionate butyrate 95-50 Example 16 Parts Ethanolamine propionate butyrate Example 17 Parts Neats-ioot oil 5-50 Ethanolamine propionate butyrate 95-50 ,Example 18 Parts Blown neats-foot oil 20 'Ethanolamine dibutyrate 80 Example 19 I Parts Blown neats-foot oil 80 Diethanolamine tripropionate 20 Example 20 I Parts Blown neats-foot oil 80 Ethanolamine acetate propionate 20 any suitable means. The amount of condition- 7 As willoe apparent from'the above examples -and: description the: conditioning agents :of our 'ing liquid applied may vary between -25% by" weightof the yarn. Usually, however, the amount of conditioning liquid applied is about -15% by I I weight of the yarn. Yarn composed of cellulose acetate conditioned as described abovegives ex 'celle'nt' results: when used in thecircular knitting process. I
invention may be applied by a wide variety of methods. For example, we may employ the agent 1 as an ingredient of the spinning dope from whichv vulva the filamentsare formed, the amount ofthe' agent so employed depending upon a number of fac-:
tors; such as the particular cellulose derivative used in making the yarn, thesolvent or solvent I 1 combination used in making upthe spinning so-v lution, and the degree I of softness or pliability desired in the yarn, etc.
If the conditioning agent is to be applied to the yarn afterspin'ning, this maybe done by bringing the'yarn in contact with a wick, roll,:'
or felt wet therewith, or the liquid may be applied l ing onto cones, spools, bobbins, or the like or by the SO-Called bobbin to bobbin method. In,
the case of staple fiber'manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.
to be put and other factors. For example, in a given case where a cellulose Organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight .of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.
Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.
'Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, thesepercentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent or softening action of the conditioning agent, the amount of formulas described herein are applicable to the conditioning of, many other types of cellulose de-; I rivative yarns such as those composed'of or'con- I I taining cellulose propionate, cellulose butyrate,
cellulose acetate :propionate, cellulose acetatev butyrate, ethyl cellulose, methyl cellulose, benzyl 1 cellulose and others; as wellas to the condition- I ing of silk, wool, cotton, viscose and other natural or artificial materials. 1
The term :yarn? as'used herein and in the claims is'to be understood as including a single the form of a thread, either of high or low twist,
ture of natural and artificial filamentsor a: composite :threadformed by twisting together individual strands of natural or; artificial :materials, I I I as well as, cut staple fibers produced from nat-' 'ural and/or artificialfilaments 01' threads and,
spun yarn'produced from such staple fibers. 1 1
i As indicated: above, thev yarn conditioning agents: of our invention are exceptionally good;
solvents for a wide variety of mineraL'blown and 'unblown, drying and semi-drying animal and. 1 vegetable oils: such as cottonseed, olive, castor, f
neats-foot, sperm and other oils, This enables filament, a plurality of filaments associated: into v "single 'or multiple threads associated or twisted together, composite threads composed of a mix-y up a; variety :of'yarntreating formulas of vary- 'ing'compo'sitionr m: w: I I I I v :tions of ourinvention possess many outstanding advantages"I'he' fundamental and outstanding:
characteristic of the agents employed in accordance with theinventionis their ability to soften yarns, especially those composed of orv containing:
yarn material. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due
,to their solubility'in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly-satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.
What we claim is: c
l. The process of conditioning yarn to render it more amenable to textile operations including knitting, Weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softeningcomponent an organic ester amide having the general formula:
V O a where R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from thegroup consisting of substituted, and unsubstituted alkyl, aryl and. cycloalkyl; X is CO--; n is l, b is at least 1 and R'X may be hydrogen.
2. The process of conditioning yarn-composed 3.!v I organic derivatives of cellulose such as cellulose acetate and render them soft and; pliable and y amenable; to various textile operations, especiallyl operations such as those involved in weaving and 1 I 1 v knitting where complicated: designs or stitches are 4o employed, without too drastic an action on the where R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; 11. is 1, b is at least 1 and RX may be hydrogen.
3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an organic ester amide having the general formula:
wherein R is a radical selected from'the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.
4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an organic ester amide having the general formula:
(RIX),, -N (R) 0 (3' R) v I 0 a where R is a radical selected from the group consisting of alkyl, cycloalkyl'and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl,
aryl and cycloalkyl; X is CO 11. is 1, b is at least l and RX may be hydrogen, and textile lubricant.
5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component diethanolamine tripropionate.
6. The process of conditioning yarn composedv of or containing cellulose acetate to render it more amenable to textile operationsincluding knitting, weaving, spinning, and the like, which.
8. A conditioning agent for rendering y'arns more amenable to textile operations includin knitting, weaving, spinning and the like which comprises an organic ester amide having the general formula:
wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl;, X is CO; n is 1, b is at least 1 and RX may be hydrogen.
9. A conditioning agent for rendering textile yarns composed of or containing organic derivatives of cellulose more amenable to textile operations including knitting, WeaVing spinning and the like which comprises an organic ester amide having the general formula:
wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; 11 is 1, b is at least 1 and RX may be hydrogen and a textile lubricating oil.
10. A conditioning agent for rendering yarns composed of or containing cellulose acetatemore amenable to textile operations including knitting, weaving, spinning, and the like containing diethanolamine tripropionate.
1-1. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ethanolamine acetate propionate.
12. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ethanolamine propionate butyrate.
l3. Textile yarn amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing an organic ester amide having the general formula:
, A I h wherein R is a radical selected from the group consisting ofallwl, cycloalkyl and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.
14. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:
(RX),.N -(R).(O,(|l-R") wherein R. is a radical selected from the group -consisting of alkyl, cycloalkyl and aryl; Rf and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is l, b is at least 1 and RX may be hydrogen.
15. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:
( )N(R),. 00-11") ll wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; Xis CO; n is 1, b is at least 1 and R'X may be hydrogen and a textile lubricant. 16. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting,. weaving, spinning and the like, impregnated with a lubricant comprising diethanolamine tripropionate.
17. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine acetate propionate.
18. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine propionate butyrate.
JOSEPH B. DICKEY. JAMES G. MCNALLY.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL27399D NL27399C (en) | 1938-04-26 | ||
NL49392D NL49392C (en) | 1938-04-26 | ||
US204374A US2143765A (en) | 1938-04-26 | 1938-04-26 | Yarn conditioning process and composition therefor |
GB12482/39A GB531316A (en) | 1938-04-26 | 1939-04-26 | Improvements in cellulose derivate compositions, films, yarns, or the like containing organic ester amides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US204374A US2143765A (en) | 1938-04-26 | 1938-04-26 | Yarn conditioning process and composition therefor |
Publications (1)
Publication Number | Publication Date |
---|---|
US2143765A true US2143765A (en) | 1939-01-10 |
Family
ID=22757645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US204374A Expired - Lifetime US2143765A (en) | 1938-04-26 | 1938-04-26 | Yarn conditioning process and composition therefor |
Country Status (3)
Country | Link |
---|---|
US (1) | US2143765A (en) |
GB (1) | GB531316A (en) |
NL (2) | NL27399C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2472900A (en) * | 1946-05-01 | 1949-06-14 | Carbide & Carbon Chem Corp | Vinyl chloride resins plasticized with diester-amides |
US2576898A (en) * | 1945-04-09 | 1951-11-27 | Ciba Ltd | Semiesters of unsaturated dicarboxylic acids |
US3318837A (en) * | 1963-01-22 | 1967-05-09 | Frank C Magne | Diesteramide plasticizers for vinyl chloride and nitrile rubber compositions |
US3340218A (en) * | 1963-01-22 | 1967-09-05 | Frank C Magne | Diesteramide plasticizers |
EP0373546A2 (en) * | 1988-12-14 | 1990-06-20 | Hoechst Aktiengesellschaft | Use of triacylated ethanolamines as liquid water miscible peroxyde activators |
-
0
- NL NL49392D patent/NL49392C/xx active
- NL NL27399D patent/NL27399C/xx active
-
1938
- 1938-04-26 US US204374A patent/US2143765A/en not_active Expired - Lifetime
-
1939
- 1939-04-26 GB GB12482/39A patent/GB531316A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2576898A (en) * | 1945-04-09 | 1951-11-27 | Ciba Ltd | Semiesters of unsaturated dicarboxylic acids |
US2472900A (en) * | 1946-05-01 | 1949-06-14 | Carbide & Carbon Chem Corp | Vinyl chloride resins plasticized with diester-amides |
US2472901A (en) * | 1946-05-01 | 1949-06-14 | Carbide & Carbon Chem Corp | 2,2' (2-ethylhexanamido) diethyl di (2-ethylhexanoate) |
US3318837A (en) * | 1963-01-22 | 1967-05-09 | Frank C Magne | Diesteramide plasticizers for vinyl chloride and nitrile rubber compositions |
US3340218A (en) * | 1963-01-22 | 1967-09-05 | Frank C Magne | Diesteramide plasticizers |
EP0373546A2 (en) * | 1988-12-14 | 1990-06-20 | Hoechst Aktiengesellschaft | Use of triacylated ethanolamines as liquid water miscible peroxyde activators |
EP0373546A3 (en) * | 1988-12-14 | 1991-04-03 | Hoechst Aktiengesellschaft | Use of triacylated ethanolamines as liquid water miscible peroxyde activators |
Also Published As
Publication number | Publication date |
---|---|
GB531316A (en) | 1941-01-02 |
NL27399C (en) | |
NL49392C (en) |
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