GB455622A - Improved process for saponifying materials made from cellulose esters - Google Patents
Improved process for saponifying materials made from cellulose estersInfo
- Publication number
- GB455622A GB455622A GB12186/35A GB1218635A GB455622A GB 455622 A GB455622 A GB 455622A GB 12186/35 A GB12186/35 A GB 12186/35A GB 1218635 A GB1218635 A GB 1218635A GB 455622 A GB455622 A GB 455622A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cellulose acetate
- bromide
- saponified
- product
- dyestuffs
- 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
Links
- 239000000463 material Substances 0.000 title abstract 3
- 229920002678 cellulose Polymers 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 7
- 239000004744 fabric Substances 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 abstract 3
- 238000007127 saponification reaction Methods 0.000 abstract 3
- 229920002955 Art silk Polymers 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- FADYGXGJTNYCHZ-UHFFFAOYSA-M benzyl-dodecyl-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 FADYGXGJTNYCHZ-UHFFFAOYSA-M 0.000 abstract 2
- 238000007639 printing Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- HTDIUWINAKAPER-UHFFFAOYSA-N trimethylarsine Chemical compound C[As](C)C HTDIUWINAKAPER-UHFFFAOYSA-N 0.000 abstract 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- PLALKSRAHVYFOH-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-phenylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CC1=CC=CC=C1 PLALKSRAHVYFOH-UHFFFAOYSA-N 0.000 abstract 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 1
- ZHKKNUKCXPWZOP-UHFFFAOYSA-N 1-chloroundecane Chemical compound CCCCCCCCCCCCl ZHKKNUKCXPWZOP-UHFFFAOYSA-N 0.000 abstract 1
- LFYSWCFSJAZQJJ-UHFFFAOYSA-L 1-dodecylpyridin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCC[N+]1=CC=CC=C1.CCCCCCCCCCCC[N+]1=CC=CC=C1 LFYSWCFSJAZQJJ-UHFFFAOYSA-L 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 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 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- ZKTFOYLBXYLNKZ-UHFFFAOYSA-N [4-(2-phenylacetyl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C(=O)CC1=CC=CC=C1 ZKTFOYLBXYLNKZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000084 colloidal system Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010018 discharge printing Methods 0.000 abstract 1
- FMKIALVWFRPLDZ-UHFFFAOYSA-M dodecyl(trimethyl)arsanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[As+](C)(C)C FMKIALVWFRPLDZ-UHFFFAOYSA-M 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- QBSNQUFFRJVUBO-UHFFFAOYSA-N ethyl-hexadecyl-methylsulfanium Chemical compound CCCCCCCCCCCCCCCC[S+](C)CC QBSNQUFFRJVUBO-UHFFFAOYSA-N 0.000 abstract 1
- TXPMUPUOSOZCCS-UHFFFAOYSA-N hexadecyl(trimethyl)phosphanium Chemical compound CCCCCCCCCCCCCCCC[P+](C)(C)C TXPMUPUOSOZCCS-UHFFFAOYSA-N 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- -1 naphthalene sulpho Chemical class 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 229910001923 silver oxide Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- ZZOQFIZKJGEGER-UHFFFAOYSA-M trimethyl(undecyl)stibanium chloride Chemical compound [Cl-].C[Sb+](CCCCCCCCCCC)(C)C ZZOQFIZKJGEGER-UHFFFAOYSA-M 0.000 abstract 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004804 winding Methods 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
-
- 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
- D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
- D01F2/28—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate
-
- 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
- D06M11/32—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic System
-
- 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
- D06M11/32—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic System
- D06M11/385—Saponification of cellulose-acetate
Abstract
Materials comprising cellulose esters are saponified by means of an alkaline agent in the presence of an organic base, or salt of such base, having pentavalent nitrogen, phosphorus, antimony, or arsenic, or tetravalent sulphur, and which contains a chain of at least four carbon atoms and is capable of being adsorbed by the materials. Examples of such bases or salts are dodecyltrimethylammonium bromide, octadecenyltrimethylammonium bromide, dodecylpyridinium sulphate, diethylbenzyl-dodecylammonium chloride, the addition product of dimethyl sulphate and naphthalene sulpho - N - b - oxyethyl - N<1> - dimethyl - 1, 3-propylenediamine (obtained by reacting naphthalene-b -sulphochloride with N-b -oxyethyl-1-amino - 3 - dimethylaminopropane) p-methoxyphenylacetophenone - o - trimethylammonium bromide (obtained by brominating p-acetoxyphenylacetophenone in acetic acid and allowing a solution of the product in dioxane to stand with two molecular proportions of trimethylamine until the product is soluble in water), methylethylcetylsulphonium methosulphate, cetyltrimethylphosphonium iodide, trimethyldodecylarsonium hydroxide (obtained by the action of dodecyl bromide on trimethylarsine and reacting the product with moist silver oxide) and trimethylundecyl stibonium chloride (obtained by reaction of undecyl chloride and trimethyl stibine. The process is applicable in the superficial saponification of films; in the saponification of mixed fabrics from cellulose acetate artificial silk and regenerated artificial silk for the purpose of dyeing them in common by means of direct cotton dyestuffs for subsequent discharge printing; for grounding cellulose acetate fabrics with alkali naphthol or printing cellulose acetate fabrics with vat dyestuffs or mixtures of diazo-compounds and azo-compounds, wherein the printing paste must cause local saponification. The threads may be treated with resists, e.g. sodium cresol sulphonate, advantageously in the presence of a protective colloid. In examples: (1) a cellulose acetate fabric is saponified in the presence of dodecyltrimethylammonium bromide, and dyed with direct dyestuffs; (2) cellulose acetate fabric is saponified in the presence of para-ethoxyacetanilide-o -trimethylammonium bromide; (3) cellulose acetate fabric is saponified in presence of diethylbenzyl - dodecylammonium chloride; and (4) cellulose acetate filaments are treated during winding with a solution of trimethyldodecylammonium bromide and methyl glycol, spun with similar yarn prepared with olive oil, worked into a fabric, and dyed with direct dyestuffs.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE455622X | 1934-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB455622A true GB455622A (en) | 1936-10-23 |
Family
ID=6539065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12186/35A Expired GB455622A (en) | 1934-04-21 | 1935-04-23 | Improved process for saponifying materials made from cellulose esters |
Country Status (3)
| Country | Link |
|---|---|
| US (2) | US2144202A (en) |
| FR (1) | FR788985A (en) |
| GB (1) | GB455622A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011392B (en) * | 1955-02-21 | 1957-07-04 | Hoechst Ag | Process for the partial saponification of shaped structures from high-melting polymers with ester groups in the chain |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2427126A (en) * | 1941-10-24 | 1947-09-09 | Bonard Claude | Production of textiles and other articles having a basis of a polyvinyl compound |
| US2423643A (en) * | 1943-04-22 | 1947-07-08 | American Cyanamid Co | Condensation products of guanylurea with alkylene oxides |
| US2426912A (en) * | 1944-04-26 | 1947-09-02 | Gen Electric | Process of hydrolyzing dimethyldihalogenosilanes |
| US2481388A (en) * | 1945-08-24 | 1949-09-06 | Du Pont | Hydrolysis of polyvinyl esters |
| US2622075A (en) * | 1946-12-03 | 1952-12-16 | Sandoz Ltd | Polyamine-cyanamide resins |
| US2581832A (en) * | 1947-09-05 | 1952-01-08 | Du Pont | Heterogeneous, basic hydrolysis of carboxylic acid esters of polyvinyl alcohol with quaternary ammonium bases |
| US3140231A (en) * | 1961-08-14 | 1964-07-07 | Rohm & Haas | T-octylguanidines as antihypertensive agents |
| US3414644A (en) * | 1965-01-04 | 1968-12-03 | Celanese Corp | Method for spinning bicomponent cellulose esters |
-
1935
- 1935-04-18 FR FR788985D patent/FR788985A/en not_active Expired
- 1935-04-19 US US17339A patent/US2144202A/en not_active Expired - Lifetime
- 1935-04-23 GB GB12186/35A patent/GB455622A/en not_active Expired
-
1937
- 1937-09-14 US US163741A patent/US2208857A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011392B (en) * | 1955-02-21 | 1957-07-04 | Hoechst Ag | Process for the partial saponification of shaped structures from high-melting polymers with ester groups in the chain |
Also Published As
| Publication number | Publication date |
|---|---|
| FR788985A (en) | 1935-10-21 |
| US2208857A (en) | 1940-07-23 |
| US2144202A (en) | 1939-01-17 |
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