US1878783A - Dttstby in basle - Google Patents
Dttstby in basle Download PDFInfo
- Publication number
- US1878783A US1878783A US1878783DA US1878783A US 1878783 A US1878783 A US 1878783A US 1878783D A US1878783D A US 1878783DA US 1878783 A US1878783 A US 1878783A
- Authority
- US
- United States
- Prior art keywords
- acids
- absence
- cellulose
- anhydrides
- halides
- 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
- 238000000034 method Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 235000013311 vegetables Nutrition 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229920003043 Cellulose fiber Polymers 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002649 immunization Methods 0.000 description 5
- 230000003053 immunization Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- 101100489581 Caenorhabditis elegans par-5 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- -1 linen Polymers 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical class CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 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
- D06M13/10—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
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Definitions
- the present invention relates to new cellulosic materials. It comprises the new products, their process of manufacture, their application in the textile industry, and par- 5 ticularly the mixed fabrics made with the aid of the new products.
- phthalic anhydride maleic anhydride, succinic anhydride, benzoyl chlo-' 40 ride and benzoic anhydride, as well as their homologues or analogues'deriving from ben-' Zoic acids substituted in the aromatic nucleus, such as the halogenated and nitrated benzoic acids, or the methyl-benzoic acids, phthalic 4 chloride, etc.; among the tertiary bases pyribenzoyl-chloride and 100 parts of also employ mixtures of esterifying agents.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
v Patented Sept. 20, 1932 FATE FFME
ALBERT LANDOLEOF BASEL, SWITZERLAND, ASSIGNOR TO SOCIETY OF CHEMICAL IN- D'U'S'IRY IN BASLE, OF BASED, SWITZERLAND GELLULOSIG MATERIALS AND PROCESS OF MAKING SAME 2N0 Drawing. Application filed August 31, 1929, Serial No. 389,860, and in Switzerland September 8, 1928.
The present invention relates to new cellulosic materials. It comprises the new products, their process of manufacture, their application in the textile industry, and par- 5 ticularly the mixed fabrics made with the aid of the new products.
Hitherto textile fibers of vegetable origin have been immunized either by firstly transforming same into an alkaline derivative,
m and then treating same with esterlfymg agents, or by directly treating same with esterifying agents in presence of a catalyst having an acid reaction.
All these processes are either complicated or involve-the danger of more or less transforming the fiber into hydrocellulose.
The observation has now been made that textile fibers of vegetable origin, such as cotton, linen, or artificial silks from regen- 2o erated cellulose, can be transformed in one single operation, without danger for the fiber itself, into products which have no afiinity for substantive dyestuffs, if the fiber is esterified by subjecting it, in the presence of tertiary amines, to the action of a group of derivatives from organic carboxylic acids comprising the anhydrides and halides of such acids. This process has the advantage that it does not require a preliminary treatment,
of the fiber with alkalies or acids. Moreover,
it has the further advantage to yield products which are very stable to storing, because an accidental saponification of the fiber causes no deposition of an acid on the same which would .destroythe cellulose.
Among the anhydrides and halides of the carboxylic acids used for this-invention there may be cited phthalic anhydride, maleic anhydride, succinic anhydride, benzoyl chlo-' 40 ride and benzoic anhydride, as well as their homologues or analogues'deriving from ben-' Zoic acids substituted in the aromatic nucleus, such as the halogenated and nitrated benzoic acids, or the methyl-benzoic acids, phthalic 4 chloride, etc.; among the tertiary bases pyribenzoyl-chloride and 100 parts of also employ mixtures of esterifying agents.
dine, quinoline, triethylamine, 'etc., may be mentioned.
Example.
.15- parts of cotton are jtreated during 4' hours at C. in a mixture of 100 parts of pyridine and 10 parts of phthalic anhydride, or 10 parts of cotton are treated in a mixture previously heated to 40 C. of 10 parts of I pyridine. 4% The whole is carefully stirred while the temperature is raised to and kept at this temperature during 1 hour. The cotton is then hydro-extracted, carefully washed, and dried. The cotton has lost all affinity for substantive dyestuffs, and has also no aflinity for acid' dyestuffs, whereas, in the case where it had been treated with phthalic anhydride, the cotton has acquired a very strong alfinity for basic'dyestuils.
Similar effects are obtained with other halides and other anhydrides of carboxylic acids.
The mentioned proportions can of course be varied within large limits, and one can What I claim is 1. As a new process the immunization of vegetable textile fibers by esterification, consisting in heating such cellulose fibers, which have not been converted into alkali cellulose in the presence of 'a tertiary amine, and in the absence of solvents which dissolve the esters formed, and of catalysts, with a group of derivatives from organic carboxylic acids consisting of the anhydrides and halides of 80 such acids, the process being carried out in the absence of water. v
2. As a new process the immunization of vegetable textile fibers by esterification, consisting in heating such cellulose fibers, which have not been converted into alkali cellulose in the presence of a tertiary amine, and in the absence of solvents which dissolve the esters formed, and of catalysts, with a. group of derivatives from organic carboxyllc acids formed, andof catalysts,with a containing at least 3 carbon atoms consisting of the anhydrides-and halides of such acids,
the process being carried out in the absence of water.
3. As anew process the immunization of vegetable textile fibers by esterification, consisting in treating such cellulose fibers, which have not been converted into alkali cellulose in the presence of a tertiary amine, and
in the absence of solvents which dissolve the esters'formed, and of catalysts, with a grou of derivatives from aromatic carboxylic aci s consisting of the anhydrides and halides of such acids, the process being carried out in the absence of water.
4. As a new process the immunization of vegetable textile fibers by esterification, con-' sisting in treating such cellulose fibers, which have not been converted into alkali cellulose inthe presence of pyridine, and in the ab sence. of solvents which dissolve the esters group of derivatives from benzo1c acids consisting of the anhydrides and halides of such acids, the process, being carried out in the absence of water. Y a
5. As a new process the immunization of vegetable textile fibers by esterification, consisting' in treating such cellulose fibers, which have not been converted into alkali cellulose, in the presence of pyridine, and in the absence of solvents which dissolve the esters formed, and of catalysts, with benzoyl chloride, the process being carried out in the absence of water.
I In witness whereof I have hereunto signed of August 1929.
my name this 21st da BERT LANDOLT.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1878783A true US1878783A (en) | 1932-09-20 |
Family
ID=3424630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1878783D Expired - Lifetime US1878783A (en) | Dttstby in basle |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1878783A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486720A (en) * | 1945-12-22 | 1949-11-01 | Callaway Mills Co | Adhesion of rubber to fibrous materials |
| US3148021A (en) * | 1961-08-28 | 1964-09-08 | Dan River Mills Inc | Novel creaseproofing compositions, and methods and creaseproofed textiles |
| US4113431A (en) * | 1975-02-27 | 1978-09-12 | Shikibo Limited | Method for dyeing cellulose fibers by disperse dyes |
-
0
- US US1878783D patent/US1878783A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486720A (en) * | 1945-12-22 | 1949-11-01 | Callaway Mills Co | Adhesion of rubber to fibrous materials |
| US3148021A (en) * | 1961-08-28 | 1964-09-08 | Dan River Mills Inc | Novel creaseproofing compositions, and methods and creaseproofed textiles |
| US4113431A (en) * | 1975-02-27 | 1978-09-12 | Shikibo Limited | Method for dyeing cellulose fibers by disperse dyes |
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