US2208857A - Process of saponifying textile materials - Google Patents
Process of saponifying textile materials Download PDFInfo
- Publication number
- US2208857A US2208857A US163741A US16374137A US2208857A US 2208857 A US2208857 A US 2208857A US 163741 A US163741 A US 163741A US 16374137 A US16374137 A US 16374137A US 2208857 A US2208857 A US 2208857A
- Authority
- US
- United States
- Prior art keywords
- guanidine
- saponifying
- saponification
- textile materials
- alkali
- 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
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- 238000000034 method Methods 0.000 title description 12
- 239000000463 material Substances 0.000 title description 9
- 239000004753 textile Substances 0.000 title description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 23
- -1 isothiourea ethers Chemical class 0.000 description 17
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 15
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 15
- 238000007127 saponification reaction Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 239000003513 alkali Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002357 guanidines Chemical class 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- CGMKPKRNUNDACU-UHFFFAOYSA-N carbamimidoyl(dodecyl)azanium;chloride Chemical compound Cl.CCCCCCCCCCCCN=C(N)N CGMKPKRNUNDACU-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- YSAUPAXBNIHZDC-UHFFFAOYSA-N 1-(diaminomethylidene)-2-dodecylguanidine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCN=C(N)N=C(N)N YSAUPAXBNIHZDC-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- OFUCECQHSZYGNW-UHFFFAOYSA-N 2-(4-methylpentyl)guanidine Chemical compound CC(C)CCCN=C(N)N OFUCECQHSZYGNW-UHFFFAOYSA-N 0.000 description 1
- IZBZQUREHISXFJ-UHFFFAOYSA-N 2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetic acid Chemical compound CC1=C(Cl)C(C(F)(F)F)=NN1CC(O)=O IZBZQUREHISXFJ-UHFFFAOYSA-N 0.000 description 1
- USGCMNLQYSXCDU-UHFFFAOYSA-N 2-cyclohexyl-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1CCCCC1 USGCMNLQYSXCDU-UHFFFAOYSA-N 0.000 description 1
- AJGAPBXTFUSKNJ-UHFFFAOYSA-N 2-cyclohexylguanidine Chemical compound NC(=N)NC1CCCCC1 AJGAPBXTFUSKNJ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- LZSQFERICNZJTM-UHFFFAOYSA-N acetic acid 2-cyclohexylguanidine Chemical compound C(C)(=O)O.C1(CCCCC1)NC(=N)N LZSQFERICNZJTM-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-M naphthalen-1-olate Chemical compound C1=CC=C2C([O-])=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
"UNITED STATES raocnss or saromr'rma TEXTILE TERIALS Paul Sehlack, Berlln-Treptow, Germany, assignor to I. G. Farbenindu'strle Aktiengesellacha'lt, Frankfort-on-the-Main, Germany No Drawing.
--Serial 1934 The present invention relates to a process of saponifying hydrolyzable textile materials and films. More particularly the invention consists in adding to the liquid containing the hy- 5 drolyzing agent a guanidine or biguanidine with an aliphatic carbon chain of more than 6 carbon atoms and eflecting saponiflcation with this liquid.
- It is an object of the invention to provide means by which the saponifying process may be substantially accelerated and the saponiflcation rendered more uniform.
Further objects will appear from the detailed specification following hereafter.
-This application may be regarded as a continuation in part of my copending application Ser. No. 17,339 filed April 19, 1935, Pat. No. 2,144,202 which discloses the use of organic onium compounds of capillary active character as accelerators of the saponification of cellulose esters.
U. S. patent application Ser. No. 17,339 de-- scribes a process for markedly accelerating the alkaline saponiflcation of cellulose esters, for example cellulose acetate, in the form of artificial silk by adding to the saponifying agent, for example an aqueous dye bath or a printing paste, a base or the salt of a base containing pentavalent nitrogen, phosphorus, arsenic or antimony or tetravalent sulfur, of which the cation is capable of .being adsorbed by capillary attraction or has another specific affinity for the goods to be saponiiied. Especially suitable cations are those having aliphatic or aromatic residues of 35 high molecular weight, for example dodecyltrimethylammonium bromide and para-methoxyaceto-phenone-omega-trimethylammonium bromide.
7 40 This invention is based on the observation that there can advantageously be used for this purpose compounds which are derived from guanidine. or such compounds, only those are strongly effective which are capable of existing in alkaline solution as ammonium bases containing pentavalent nitrogen. The isothiourea ethers and iso-urea ethers, though similar to guanidine, are. not effective, since in alkaline solutions they exist in the form of anhydro-bases with trivalent nitrogen or, in the case of fully alkylated compounds, are hydrolyzed to the corresponding tetraalkylurea or'thiourea (cf. Lecher 8; Graf, Liebigs Annalen, vol. 438, pages 158 and 159).
Aryl guanidine and aryl biguanid ine, which are i or dodecyibiguanide.
Application September 14, 1937, N0. 163,741. In Germany April 21,
4 Claims. (01. 8-130)" evidently incapable of existing as bases having pentavalent nitrogen, are also not useful.
Common guanidine and blguanidine, which have a certain aflinity for acetate silk, is effective and can, for example, be used with advantage 5 in alkaline printing pastes and padding solutions if saponification of the acetate silk or other cel-' lulose ester is intended by printing with preparations containing for example a naphthol or naphtholate.- Even in dilute aqueous solution 10 the action of the guanidine is quite noticeable. The alkyl guanidines are more efiective, especially those having an aliphatic or hydrocyclic residue with 6 or more, preferably 8 to 14 carbon atoms. Examples of such compounds are cyclohexylguanidine, isohexylguanidine and dodecylguanidine. With longer chains the effect may decrease because the substance penetrates the goods less deeply and has a smaller solubility in the alkaline bath. The effect obtained with guanidines is also obtained with biguanides, for example cyclohexylbiguanide, isoheptylbiguanide The guanidine derivatives may also contain hydroxy-alkyl groups as substituents, whereby the range of solubility is extended.
The guanidine and biguanidine derivatives can be used in manner similar to that in which the bases of the aforesaid prior process are used,
namely in combination for example with the fol- 3o lowing saponifiying agents: alkali or alkaline earth hydroxides, alkali carbonates, borates or silicates, trialkali silicates, or organic bases such as triethanolamine or ethylene diamine.
For saponifying in aqueous baths, substances having 8 to 14 carbon atoms are the most suitable. In printing pastes substances of lower molecular weight and greater solubility are preferable, especially those with hydroxyalkyl groups. The action of the reagent is also dependent on the conditions of Operation. The ion content of the solution is of considerable importance. 'Indilute alkali lyes with only a small content of electrolyte, substances with a higher molecular weight may be used in a given saponification, than when a more highly concen- -.trated alkali carbonate solution is used. It is known that many polar substances'which are capable of capillary adsorption in concentrated operation of a compound included in the invention is easily determined by a preliminary test. For example a small sample of an acetate silk fabric is saponified at 60 C. with the quantity of N/20-N/40 lye necessary for a 10 per cent saponification (calculated as decrease in dry weight) until a'quarter of the alkali has been consumed; this is compared with an experiment in which the substance to be tested is added in the form of a neutral salt, preferably a hydrochloride, in ,1 of the quantity equivalent to the alkali hydroxide. The consumption of alkali is determined titrimetrically, and the material thoroughly freed from the catalyst by treating with l/40 N hydrochloric acid at 40 C. is dyed with 2 per cent Diamine Pure Blue.
Textile materials of hydrolyzable artificial organic polymerides, for example polyvinyl esters or polyacrylic acid esters, can be wholly or partially saponified in a manner similar to that used for cellulose acetate or other cellulose esters,
The textile materials may have the form af artificial silk, staple fiber, filaments, foils, films, ribbons, bristles, artificial horseand rabbit-hair, fabrics, and the like. The acceleration of the saponification does not only shorten the time of procedure, but it also ensures that the material is considerably less apt to be damaged, especially in those cases where mixtures with animal fibers are treated.
The invention is illustrated by the following examples:
(1) A fabric of acetate silk is handled for 30 minutes in a bath of liquor ratio 1:100 at 55-60 C., which contains per liter l gram of sodium hydroxide, 10 grams of sodium acetate and 1.1 gram of dodecylguanidine hydrochloride. The saponified fabric can be dyed a medium depth with Diamine Pure Blue FF (Schultz Farbstofftabellen,
7th ed., vol. I, page 209) whereas fabric treated in like manner, but without the addition of the guanidine derivative, is dyed only Weakly and unevenly. The dodecylg-uanidine is obtained by warmingdodecylamine with an alcoholic solution of S-methylisothiourea methosulfate.
Similar effects as the one described may also be obtained with substantially smaller quantities of dodecylguanidine.
(2) The dodecylguanidine hydrochloride of Example 1 is exchanged for dodecylbiguanide mono-hydrochloride or bromide. The saponification is approximately the same.
The dodecylbiguanide mono-hydrobromide is obtained by warming dodecylamine in an alcoholic solution with 3-ethyl-guanylisothiourea hydrobromide. The hydrochloride is obtained by heating dicyandiamide with dodecylamine hydrochloride.
(3) Acetate silk is saponified by sodium hydroxide inthe presence of mol of 'y-phenoxy- B-hydroxypropyl-guanidine reckoned on the alkali used.
The -phenoxy-fl-hydroxypropyl guanidine is obtained by splitting phenoxypropene oxide with an execss of ammonia and treating the primary hydroxyamine so formed with S-methylisothiourea.
(4) An acetate silk containing 10 per cent of nitrocellulose is de-nitrated with a solution containing 120 grams of sodium hydrosulfide and 2 grams of dodecyl-guanidine per liter for hour at 60 C. The silk so treated. no longer gives the diphenylamine reaction, and can be dyed with many direct dyestuffs, for example Sirius Blue BB.
(5) Acetate silk is saponified as in Example 1, except that the accelerating agent is ,a-dodecylethylene guanidine. 4
(6) An acetate silk fabric is saponified at 75 C. in a bath containing grams of sodium carbonate and 3 grams of cyclohexylbiguanidine hydrochloride. The saponifiation proceeds more quickly than without the additon of the biguanide.
(7) A cellulose acetate film is saponifled at 75 C. in n/10 caustic soda lye containing 10 grams of sodium chloride and 2 grams of dodecylguanidine per liter until it can be dyed uniformly with a medium tone by a direct dyestufl. This effect is obtained considerably more quickly with the addition of the accelerating agent than without it.
(8) A satin fabric of cellulose acetate silk is printed with a paste of the following. composition:
Grams Cyclohexylguanidine acetate 50 Water--- 370 Potassium carbonate 80 Tragacanth, 602100 500 ing the guanidine derivative.
In the claims following hereafter the term aliphatic comprises substituted alkyl radicals such as hydroxyalkyl and aralkyl.
What I claim is:
1. A process of saponifying artificial textile materials or films mainly consisting of cellulose esters, polymerized vinyl esters, polymerized acrylic acid esters, which process comprises performing the saponification with a solution of mineral alkali containing as a saponification catalyst a relatively small amount insufficient to cause saponification of a guanidine compound selected from the group consisting of guanidinium and biguairidinium bases and their salts, said guanidine compound containing in its molecule a radical selected from the group consisting of aliphatic and hydrocyclic radicals with at least six carbon atoms.
2. A process of saponifying textile materials or films consisting mainly of organic cellulose esters, which process comprises performing the saponification with a solution of mineral alkali containing as a saponification catalyst about one fifth of the amount equivalent to the mineral alkali.
employed of a guanidine compound selected from the group consisting of guanidinium and biguanidinium bases and their salts, said guanidine compound containing in its molecule a radical selected from the group consisting of aliphatic and hydrocyclic radicals with at'least six carbon atoms.
3. A process of saponifying textile materials or films consisting mainly of organic cellulose esters, which process comprises performing the saponification with a solution of mineral alkali containing as a saponification catalyst a relatively small amount insufficient to cause saponification of a guanidine compound selected from the group consisting of guanidinium and biguanidinium bases and their salts, said guanidinium compoundof the amount 'equivalent to the-mineral alkali employed of a guanidine compound selected from the group consisting of guanidinium and biguanidinium bases and their salts, said guanidinium compound containing in its molecule an aliphatic 5 radical of 8 to 14 carbon atoms.
PAUL SCHLACK.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE455622X | 1934-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2208857A true US2208857A (en) | 1940-07-23 |
Family
ID=6539065
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US17339A Expired - Lifetime US2144202A (en) | 1934-04-21 | 1935-04-19 | Saponifying cellulose esters |
| US163741A Expired - Lifetime US2208857A (en) | 1934-04-21 | 1937-09-14 | Process of saponifying textile materials |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US17339A Expired - Lifetime US2144202A (en) | 1934-04-21 | 1935-04-19 | Saponifying cellulose esters |
Country Status (3)
| Country | Link |
|---|---|
| US (2) | US2144202A (en) |
| FR (1) | FR788985A (en) |
| GB (1) | GB455622A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US2427126A (en) * | 1941-10-24 | 1947-09-09 | Bonard Claude | Production of textiles and other articles having a basis of a polyvinyl compound |
| US2481388A (en) * | 1945-08-24 | 1949-09-06 | Du Pont | Hydrolysis of polyvinyl esters |
| US2581832A (en) * | 1947-09-05 | 1952-01-08 | Du Pont | Heterogeneous, basic hydrolysis of carboxylic acid esters of polyvinyl alcohol with quaternary ammonium bases |
| US2622075A (en) * | 1946-12-03 | 1952-12-16 | Sandoz Ltd | Polyamine-cyanamide resins |
| US3140231A (en) * | 1961-08-14 | 1964-07-07 | Rohm & Haas | T-octylguanidines as antihypertensive agents |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL91282C (en) * | 1955-02-21 | |||
| 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 (7)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR788985A (en) | 1935-10-21 |
| US2144202A (en) | 1939-01-17 |
| GB455622A (en) | 1936-10-23 |
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