US2159012A - Process for acetylating cellulose acetate textile materials - Google Patents
Process for acetylating cellulose acetate textile materials Download PDFInfo
- Publication number
- US2159012A US2159012A US39290A US3929035A US2159012A US 2159012 A US2159012 A US 2159012A US 39290 A US39290 A US 39290A US 3929035 A US3929035 A US 3929035A US 2159012 A US2159012 A US 2159012A
- Authority
- US
- United States
- Prior art keywords
- yarn
- cellulose acetate
- materials
- yarns
- treatment
- 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
- 239000000463 material Substances 0.000 title description 26
- 229920002301 cellulose acetate Polymers 0.000 title description 15
- 238000000034 method Methods 0.000 title description 10
- 239000004753 textile Substances 0.000 title description 4
- 230000000397 acetylating effect Effects 0.000 title description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000004744 fabric Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 5
- 238000006640 acetylation reaction Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000010409 ironing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229920002955 Art silk Polymers 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 235000004879 dioscorea Nutrition 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical class CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- -1 aromatic hydrocarbons acetic anhydride Chemical class 0.000 description 1
- 239000012237 artificial material Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000004855 decalinyl group Chemical class C1(CCCC2CCCCC12)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 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
- 238000007654 immersion Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000002522 swelling effect Effects 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/28—Halides of elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
- D06M13/10—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 oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
Definitions
- This invention relates to improvements in the production of yarns, fabrics and other materials, and is more particularly concerned with processes for the production'of cellulose acetate yarns, fabrics and other materials, and with the new yarns, fabrics and other materials produced thereby.
- the resistance to heat of cellulose acetate yarns, fabrics and other materials may be increased by subjecting the yarns and other materials to acetylation by treatment with diluted acetic anhydride, in the presence of ferric chloride as catalyst.
- the safe ironing point of thematerials may be increased so that they may be ironed without damage at higher temperatures than are customary in ironing ordinary cellulose acetate artificial silk.
- the treatment reduces the moisture regain of the materials and they acquire a greater resistance to. water and have a substantially greater resistance to the delustring action of hot or boiling aqueous liquids or moist steam. At the same time the tenacity and extension of the materials are well maintained.
- the af-- flnity of the yarn for dyestuffs in general, and particularly for the dispersed insoluble dyestufls now commonly applied to cellulose acetate is materially reduced, so that by association of the yams or other materials so treated with yarns or other materials of cellulose acetate or of other organic derivatives of cellulose untreated by the process, diiferential dyeing effects are obtainable, whilst at the same time the dye has an amnity for the whole of the fabric or other material in which the two types of yarn are associated.
- light and dark blue shades can be produced by the immersion in a dyebath containing an SRA blue dyestufl of a fabric containing ordinary acetone-soluble cellulose acetate yarn together with the same yarn which has been subjected to the process ofithe invention.
- the new process has the eifect of changing the solubility characteristics of the yarns or simflar materials.
- a yarn may be produced which is insoluble or much less soluble in acetone. Similar changes in the solubility characteristics occur in the treatment of other materials used as starting materials in the treatment of the invention. It is thus possible, according to the invention, to produce yarns or other materials which it is difficult or even impossible to manufacture by a simple spinning process.
- nonsolvent liquid medium is to be understood .as meaning a medium which is a non-solvent for the materials being treated throughout the whole of Application September 5, 1935, Se- 39,2 90. In Great Britain September 11,
- the acetic anhydride is diluted with a diluent which is a non-solvent for the yarn under treatment and is preferably inert thereto, though it may have a swelling action.
- a diluent for example xylene or other homologues of benzene, tetraand deca-hydronaphthalenes, and kerosene or other higher boiling petroleum hydrocarbons and also ethers, e. g. normal and iso butyl and amyl ethers, carbon tetrachloride and other non-solvent chlorinated hydrocarbons.
- the degree of dilution may be adjusted so as to prevent swelling or so as to obtainsome swelling of the yarn. In any case, it should be such as to prevent any solution or incipient solution of the yarn or any fusing together of the filaments, and, further, it may be adjusted to prevent any substantial change in the lustre orquality of the material.
- a given amount of acetic anhydride may, for example, be dissolved in 'I or 8 or 10 up to 20 times or more of its weight of xylene or other hydrocarbon. The higher dilutions are particularly conducive to avoiding change in the lustre and in quality.
- the amount of acetic anhydride on the weight of the yarn may vary very considerably, but it is usually sufllcient to use an "amount of anhydride from half to twice the weight of the material, for example a proportion of l-1 times its weight.
- the proportion may be varied according to the degree of acetylation required and according to the amount of the change in the properties of the material which I it is desiredto bring about.
- the reaction may be carried-out under atmospheric pressure, sub-atmospheric pressure, or at pressures in excess of atmospheric, for example pressures of 20 pounds per square inch or more.
- the ferric chloride may be employed either alone or in the presence of hydrochloric acid.
- hydrochloric acid is introduced into the acetylating medium in the form of co hydrochloric acid, is preferably employed in quite low concentrations.
- the actual concentration of catalyst will depend upon the concentration of acetic anhydride and other factors.
- the catalyst should not be employed in a sufficiently high concentration to bring about reaction between the anhydride employed and any diluent if such reaction is possible. For instance, with certain aromatic hydrocarbons acetic anhydride will react in the presence of ferric chloride if. present in a sufficiently high concentration.
- the term yam has been used, but it will be understood that the yarn may be treated in any suitable form, for example in the formof hanks, or on perforated bobbins in the form of woven or warp-knitted or other knitted fabrics or similar materials.
- The-starting material may be a yarn produced by the ordinary spinning process, for
- the well-known commercial acetonesoluble cellulose acetate yarn may be a yarn treated by any suitable after-treatment process.
- any suitable after-treatment process for example stretching, shrinking, dyeing or other processes.
- the yarn subsequent to its manufacture may be-subiected to a stretching treatment designed to increase its tenacity, for example by means of a solution of dioxane or other suitable solvent or in the presence of steam or hot water, as described in U. 8. application S. Nos. 4510 and 4511 filed 1st February 1935.
- the stretching'treatment may, for example, be such as to extend'the yarn by 200400% or even 1000% or more of its original length.
- Such yarns have an extremely high tenacity whichis reflected in the final product, treated according to the present invention.
- Such stretched yarns, or even ordinary artificial silk materials may, if desired, be subjected to a shrinking'treatment to increase their extensibility, for example a shrinking treatment carried out with the aid of latent solvents (see U. 8. application 8. No. 611,240-filed May 13,
- the reaction between the cellulose acetate yarn and the acetic anhydride may be carried out in any suitable manner, for example as a batch process.
- banks may be immersed for the appropriate period in the acetylation mixture, or the mixturemay be pumped or sucked through a perforated bobbin or other 0 package of the yarn.
- Example 1 removed, washed first with benzene and then with water and dilute alkali to remove traces of acid and dried.
- Example 2 60 parts of acetone-soluble cellulose acetate yarn are treated for about 1 hour at 20-25, C. in a solution consisting of about 1400 partsoi' benzene, 100 parts of aceticanhydride and 2 partsof crystallised ferric chloride. The yarn is then removed, washed as in the preceding example and dried.
- Example 3 60 parts of cellulose acetate yarn are treated for about 18 hours at a temperature of 20-25 C.
- Example 1 Example 1
- Example 4 60 parts of yarn are treated at a temperature of I 20-25" C. for about 1 hour in a medium consisting of about 800 parts' of benzene, 100 parts of acetic purpose of the present invention. cellulose anhydride, 1 part of crystallised ferric chloride then removed, washed and dried as in Example 1.
- the yarn obtained according to each of the preceding examples is chloroform-soluble, has an increased acetyl value, and improved resistance to ironing and to treatment with hot aqueous media and a decreased affinity for the ordinary cellulose acetatedyestuifs.
- Process for the production of improved artificial materials which comprises subjecting filaments, yarns, threads and similar textile materials having a basis of acetone-soluble cellulose acetate and fabrics containing such materials to acetylation with a non-solvent liquid medium comprising acetic anhydride, an organic diluent and ferric chloride until products having a reduced solubility in acetone are obtained.
- ferric chloride and hydrogen chloride until products having a reduced solubility in acetone are obtained.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2159012X | 1934-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2159012A true US2159012A (en) | 1939-05-23 |
Family
ID=10900039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US39290A Expired - Lifetime US2159012A (en) | 1934-09-11 | 1935-09-05 | Process for acetylating cellulose acetate textile materials |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2159012A (fr) |
| FR (3) | FR794693A (fr) |
-
1935
- 1935-09-05 US US39290A patent/US2159012A/en not_active Expired - Lifetime
- 1935-09-10 FR FR794693D patent/FR794693A/fr not_active Expired
- 1935-09-10 FR FR794691D patent/FR794691A/fr not_active Expired
- 1935-09-10 FR FR794692D patent/FR794692A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR794693A (fr) | 1936-02-22 |
| FR794692A (fr) | 1936-02-22 |
| FR794691A (fr) | 1936-02-22 |
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