US2111698A - Process or preparing hydrophobic cellulose fibers - Google Patents
Process or preparing hydrophobic cellulose fibers Download PDFInfo
- Publication number
- US2111698A US2111698A US102300A US10230036A US2111698A US 2111698 A US2111698 A US 2111698A US 102300 A US102300 A US 102300A US 10230036 A US10230036 A US 10230036A US 2111698 A US2111698 A US 2111698A
- Authority
- US
- United States
- Prior art keywords
- cellulose fibers
- grams
- treated
- hydrophobic cellulose
- preparing hydrophobic
- 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 title description 15
- 229920003043 Cellulose fiber Polymers 0.000 title description 9
- 230000002209 hydrophobic effect Effects 0.000 title description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- -1 aliphatic aldehyde Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229940012017 ethylenediamine Drugs 0.000 description 3
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960004011 methenamine Drugs 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical class CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical class CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- AHRBWLCVMUBFNL-UHFFFAOYSA-N 2-hydroxypropanoate;octadecylazanium Chemical compound CC(O)C([O-])=O.CCCCCCCCCCCCCCCCCC[NH3+] AHRBWLCVMUBFNL-UHFFFAOYSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MDOVKEMXFKRUEW-UHFFFAOYSA-N formic acid;hexadecan-1-amine Chemical compound OC=O.CCCCCCCCCCCCCCCCN MDOVKEMXFKRUEW-UHFFFAOYSA-N 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- SVYHKSYGLHIYEJ-UHFFFAOYSA-N n-chlorohexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCl SVYHKSYGLHIYEJ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
-
- 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
-
- 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
- D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
-
- 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
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
-
- 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
- D06M15/41—Phenol-aldehyde or phenol-ketone resins
-
- 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
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/17—Glyoxal and polyaldehyde treatment of textiles
-
- 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
Definitions
- the presentin'vention relates to a process of preparing hydrophobic cellulose fibers.
- hydrophobic properties may be imparted to cellulose fibers by incorporating with them a water-soluble salt of an amine of the constitution prescribed in the said patent application and simultaneously 0 or subsequently treating them with an aliphatic aldehyde in the absence of an appreciable quantity of free acid.
- the salts of amines the high molecular alkyl radicals of which are interrupted by heteroatoms or atom groups, for instance, acid amide groups; there may for instance be named the ethylenediamino-monostearic acid amide and the N-octodecyl-ethylene-diamine.
- the hydrophobe eiiect obtainable by the process may be considerably improved by adding to the treatment bath, in addition to the aforesaid compounds, compounds of lower molecular weight which contain in the molecule several aminoor iminogroups, or nitrogen atoms.
- the goods thus treated have a remarkable hydrophobe character, which is stable to treatment with boiling soap liquor (washing).
- the treating liquor keeps well and is still useful for impregnation purposes even after standing for several days.
- Acetate silk piece-goods are treated on the foulard with a liquor containing per liter 10 grams of stearylamine-acetate, 10 grams of melamine and 50 cc. of an aqueous formaldehyde solution of 30 per cent strength and are then wrung out. They are'then dried, preliminarily at 50-60 C., and finally for half an hour at about 100 C.
- the acetate silk thus treated has quite a surprising hydrophobe effect.
- the fabric is centrifuged, dried at 60 C. and'then heated for 30 minutes at 110 C.
- the fabric treated in this manner has a good hydrophobe effect, which property is not aflected by washing in the usual manner.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Description
Patented Mar. 22, 1938 PROCESS 0R PREPARING HYDROPHOBIC CELLULOSE FIBERS Fritz Slefert, Oppau, and Joseph Stadler, Ludwigshafen-on-the-Rhin e, Germany, assignors to 1., G. Farbenindustrie Aktiengesellschai't, Franktort-on-the-Main, Germany No Drawing.
Application September 24, 1936,
Serial 'No. 102,300. In Germany September 28,
4 Claims.
The presentin'vention relates to a process of preparing hydrophobic cellulose fibers.
In patent application Serial No. 81,122, filed May 21, 1936, (Franz Emil Hubert et al.-Process of imparting hydrophobic properties to cellulose fibers) is described a process for making cellulose fibers hydrophobe by applying to the fibers or incorporating in them a compound which contains at least one aliphatic or cycloaliphatic residue having at least 4 carbon atoms and capable of reacting with an aldehyde, for instance an amine of this constitution, and simultaneously or subsequently treating the fibers with an aliphatic aldehyde.
We have found that particularly good hydrophobic properties may be imparted to cellulose fibers by incorporating with them a water-soluble salt of an amine of the constitution prescribed in the said patent application and simultaneously 0 or subsequently treating them with an aliphatic aldehyde in the absence of an appreciable quantity of free acid.
In the process of the present invention there may suitably be used, for instance, the salts of stearylamine, octylamine, dodecylamine, cetylamine, oleylamine, ricinolamine, as well as the substitution products of these amines, for instance chlorocetylamine or the like. There are also suitable the salts of amines, the high molecular alkyl radicals of which are interrupted by heteroatoms or atom groups, for instance, acid amide groups; there may for instance be named the ethylenediamino-monostearic acid amide and the N-octodecyl-ethylene-diamine.
The use of salts in preference to the free amines in this process has the advantage that on account of their solubility in-water they are essentially more easily and economically to be applied. By the present invention it is possible to avoid the use of an organic solvent or even operation in aqueous .dispersion. When water-sol- 'uble salts of amines are used the treatment baths are very permanent and, in contrast with the emulsions of free amines, show no tendency to throw up cream or form precipitates.
The hydrophobe eiiect obtainable by the process may be considerably improved by adding to the treatment bath, in addition to the aforesaid compounds, compounds of lower molecular weight which contain in the molecule several aminoor iminogroups, or nitrogen atoms. As such further compounds may be named: 1.3.5-triazine and its derivatives, for example melamine, ammeline, ammelide and hexamethylene-tetramine; ethylene-diamine; urea, thiourea; guanidine, bigua- 'nide, guanyl-urea; cyanuric acid; biuret or the technical product obtainable by prolonged heating, for instance for 12-48 hours, of urea or thiourea at a temperature of about 160 (3.; dicyandiamide, dicyandiamidine, thiodicyandiamidine, sodium cyanamide; ortho-, paraor meta-phenylene-diamine; diaminopyridine or its derivatives and substitution products, for instance its methylol-compounds. These additions may also be made with great advantage in the process of the aforesaid patent application.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto.
.(1) In an aqueous liquor containing per liter 2 grams of melamine, 5 grams of stearylamine-acetate and 50 cc. of aqueous formaldehyde solution of 30 per cent strength, cotton piece goods are treated on a reel for 15 minutes; they are then centrifuged and dried for about 1 hour at 100 C.
The goods thus treated have a remarkable hydrophobe character, which is stable to treatment with boiling soap liquor (washing). The treating liquor keeps well and is still useful for impregnation purposes even after standing for several days.
(2) In a liquor containing per liter 5 grams of stearylamine-acetate, 5 grams of meta-phenylene-diamine and 100 cc. of an aqueous solution of formaldehyde of 30 per cent strength, artificial silk knitted goods are treated for 5 minutes at room temperature. They are then centrifuged and dried for half an hour at 100 C. This treatment imparts a hydrophobe efiect which is remarkably stable to washing.
(3) Acetate silk piece-goods are treated on the foulard with a liquor containing per liter 10 grams of stearylamine-acetate, 10 grams of melamine and 50 cc. of an aqueous formaldehyde solution of 30 per cent strength and are then wrung out. They are'then dried, preliminarily at 50-60 C., and finally for half an hour at about 100 C. The acetate silk thus treated has quite a surprising hydrophobe effect.
(4) In a bath containing per liter of water 5 grams of hexamethylene-tetramine, 5 grams of stearyl-amine-lactate and 50 cc. of formaldehyde of 30 per cent strength, a mixed tissue made from 70 per cent of wool and 30 per cent of staple fiber is treated at room temperature for 10 minutes, in a proportion of the goods to the liquor 1: 40; the tissue is then centrifuged and dried for 1 hour at 100 C. The tissue thus treated has a very good hydrophobe effect.
(5) In a bath containing per liter of water 2 rams of melamine, 5 grams of the formate of the condensation product of ethylene-diamino-monstaple fiber is treated at about 30 C. Thereupon,
the fabric is centrifuged, dried at 60 C. and'then heated for 30 minutes at 110 C. The fabric treated in this manner has a good hydrophobe effect, which property is not aflected by washing in the usual manner.
(6) In a bath containing per liter of water 5 grams of guanidine hydrochloride, 5 grams of cetyl-amine-formate and cc. of formaldehyde of 30 per cent strength, loose staple fiber is treated for 30 minutes at room temperature. After this treatment, the material is centrifuged and after drying at -60" C. it is heated for 1 hour at C. The material thus treated has a good hydrophobe effect.
(7) In a bath containing per liter of water 5 grams of dicyandiamlde, 3 grams of the acetate of N-octodecyl-ethylene-diamine and 25 cc. of formaldehyde of 30 per cent strength, a fabric made from 60 per cent of cotton and 40 per cent of staple fiber is treated on the vat winch for half an hour at room temperature. The fabric is then centrifuged and dried for 1 hour at C. The fabric treated in this manner has a high hydrophobe effect which is retained even on washing with soap and sodium carbonate.
What we claim is:
1. A process of preparing hydrophobic cellulose fibers by impregnating them with a bath which contains water-soluble salts of amines containing at least one aliphatic or cycloaliphatic radical with at least 4 carbon atoms and being capable of reacting with aldehydes, a low molecular compound containing several amino groups and an aliphatic ald :-i-.yde, and heating after the impregnating process.
2. A process of preparing hydrophobic cellulose fibers by impregnating them with a bath which contains water-soluble salts of amines containing at least one aliphatic or cycloaliphatic radical with at least 4 carbon atoms and being capable of reacting with aldehydes, a low molecular compound containing several imino groups and an aliphatic aldehyde, and heating after the impregnating process.
3. A process of preparing hydrophobic cellulose fibers by impregnating them with a bath which contains water-soluble salts of amines containing at least one aliphatic or cycloaliphatic radical with at least 4 carbon atoms and being capable of reacting with aldehydes, a low molecular compound containing several nitrogen atoms ln the molecule and an aliphatic aldehyde, and heating after the impregnating process.
4. Hydrophobic cellulose fibers containing condensation products of low molecular aliphatic compounds containing several amino groups, allphatic aldehydes and water-soluble salts of amines containing at least one aliphatic or cycloaliphatic radical with at least 4 carbon atoms and being capable of reacting with aldehydes.
FRITZ SIEFERT. JOSEPH STADLER.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI52329D DE762964C (en) | 1935-05-12 | 1935-05-12 | Process for making cellulose fibers water repellent |
| DE2111698X | 1935-09-28 | ||
| DE485593X | 1935-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2111698A true US2111698A (en) | 1938-03-22 |
Family
ID=32045547
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US81122A Expired - Lifetime US2165265A (en) | 1935-05-12 | 1936-05-21 | Process of imparting hydrophobic properties to cellulose fibers |
| US102300A Expired - Lifetime US2111698A (en) | 1935-05-12 | 1936-09-24 | Process or preparing hydrophobic cellulose fibers |
| US166224A Expired - Lifetime US2211976A (en) | 1935-05-12 | 1937-09-28 | Process of imparting hydrophobic properties to cellulose fibers |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US81122A Expired - Lifetime US2165265A (en) | 1935-05-12 | 1936-05-21 | Process of imparting hydrophobic properties to cellulose fibers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US166224A Expired - Lifetime US2211976A (en) | 1935-05-12 | 1937-09-28 | Process of imparting hydrophobic properties to cellulose fibers |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US2165265A (en) |
| BE (3) | BE415480A (en) |
| DE (1) | DE762964C (en) |
| FR (3) | FR806170A (en) |
| GB (4) | GB463300A (en) |
| NL (3) | NL45055C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2418696A (en) * | 1942-03-09 | 1947-04-08 | Courtaulds Ltd | Modifying the dyeing properties of cellulose or cellulose derivative textile materials |
| US2423185A (en) * | 1939-07-08 | 1947-07-01 | Hydronapthene Corp | Process for the manufacture of coated and impregnated materials |
| US2451426A (en) * | 1943-11-25 | 1948-10-12 | Du Pont | Bright zinc plating |
| US2594384A (en) * | 1946-11-12 | 1952-04-29 | Monsanto Chemicals | Fungi and bacteria resistant papermakers' felts and process for preparing same |
| US2600698A (en) * | 1948-11-13 | 1952-06-17 | Monsanto Chemicals | Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound |
| DE766083C (en) * | 1940-01-26 | 1954-02-01 | Ig Farbenindustrie Ag | Preparations for refining fiber materials |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE907163C (en) * | 1938-06-07 | 1954-03-22 | Hoechst Ag | Process for making natural fibers of animal or vegetable origin or artificial fibers water-repellent |
| US2446864A (en) * | 1944-06-26 | 1948-08-10 | Quaker Chemical Products Corp | Composition and process for imparting durable water repellent finish to textiles |
| NL60268C (en) * | 1944-08-14 | 1947-11-15 | ||
| US2510522A (en) * | 1944-12-09 | 1950-06-06 | Montclair Res Corp | Textile treating products and process of making |
| US2431202A (en) * | 1945-03-01 | 1947-11-18 | Gen Aniline & Film Corp | Self-dispersing methylolstear-amides |
| US2507700A (en) * | 1946-11-27 | 1950-05-16 | Monsanto Chemicals | N, n', n''-triacylmelamines |
| US2540726A (en) * | 1946-12-03 | 1951-02-06 | Du Pont | Treatment of a heat set, oriented nylon fabric with formaldehyde |
| US2565194A (en) * | 1947-03-27 | 1951-08-21 | American Cyanamid Co | Chlorotriazine resins and process of making the same |
| BE480227A (en) * | 1947-08-14 | |||
| US2562161A (en) * | 1948-02-06 | 1951-07-31 | Cluett Peabody & Co Inc | Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product |
| US2574114A (en) * | 1948-04-26 | 1951-11-06 | Bozel Maletra Prod Chimiques | Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith |
| US2608494A (en) * | 1948-08-28 | 1952-08-26 | Walkden Makin & Co Ltd | Treatment of textile fabrics for imparting antishrink properties thereto |
| US2641558A (en) * | 1948-12-24 | 1953-06-09 | Nat Lead Co | Water repellence fixative treatment |
| US2805196A (en) * | 1952-02-11 | 1957-09-03 | Tno | Permselective electrodialysis |
| DE1794282A1 (en) * | 1957-06-11 | 1971-11-25 | Minnesota Mining & Mfg | Use of higher molecular weight condensation products as surface treatment agents |
| NL114029C (en) * | 1958-02-20 | |||
| US3232697A (en) * | 1959-07-01 | 1966-02-01 | Nalco Chemical Co | Textile treatment |
| NL272600A (en) * | 1960-12-17 | |||
| US3112155A (en) * | 1962-02-02 | 1963-11-26 | Sidney L Vail | Glyoxal-amide reaction products |
| US4103051A (en) * | 1975-11-03 | 1978-07-25 | Milliken Research Corporation | Pilling reduction in textiles |
| DE2757582A1 (en) * | 1977-12-23 | 1979-06-28 | Cassella Ag | METHOD FOR THE PRODUCTION OF STORAGE-STABLE AQUEOUS EMULSIONS OF N.ALKYL-N'-ALKYLOL UREAS AND THEIR APPLICATION FOR SOFTENING LEATHER AND TEXTILE MATERIAL |
| US4295930A (en) * | 1980-03-17 | 1981-10-20 | Nalco Chemical Company | Alkoxylated dioxolanes as paper sizing agents |
| US4563288A (en) * | 1982-08-03 | 1986-01-07 | Colgate-Palmolive Company | N-Alkyl isostearamide antistatic agents, detergent compositions containing such agents, and processes for washing laundry in the presence of such agents, and with such compositions |
| US4497715A (en) * | 1982-08-03 | 1985-02-05 | Colgate-Palmolive Company | N-Alkylisostearamides as antistatic agents |
| US7713215B2 (en) * | 2008-01-31 | 2010-05-11 | Shriver Edgar L | Steering, piercing, anchoring, distending extravascular guidewire |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE219848C (en) * | 1906-04-24 | |||
| AT118595B (en) * | 1926-12-01 | 1930-07-25 | Tootal Broadhurst Lee Co Ltd | Process for impregnating textile yarns, fabrics and fabrics with synthetic resins. |
| DE542186C (en) * | 1929-06-14 | 1932-01-21 | Alexander Nathansohn Dr | Process for waterproofing raw, chemically uncleaned textile fibers |
| FR751641A (en) * | 1932-02-29 | 1933-09-07 | Ig Farbenindustrie Ag | Process for the preparation of auxiliary condensation products |
| AT136377B (en) * | 1933-01-13 | 1934-01-25 | Heberlein & Co Ag | Finishing process for vegetable textiles. |
-
0
- BE BE418549D patent/BE418549A/xx unknown
- BE BE417657D patent/BE417657A/xx unknown
-
1935
- 1935-05-12 DE DEI52329D patent/DE762964C/en not_active Expired
- 1935-06-21 GB GB17898/35A patent/GB463300A/en not_active Expired
- 1935-06-21 GB GB4212/37A patent/GB463472A/en not_active Expired
- 1935-11-08 GB GB30934/35A patent/GB467166A/en not_active Expired
-
1936
- 1936-05-06 NL NL77672A patent/NL45055C/xx active
- 1936-05-11 BE BE415480D patent/BE415480A/xx unknown
- 1936-05-11 FR FR806170D patent/FR806170A/en not_active Expired
- 1936-05-21 US US81122A patent/US2165265A/en not_active Expired - Lifetime
- 1936-09-22 NL NL79327A patent/NL44056C/xx active
- 1936-09-24 US US102300A patent/US2111698A/en not_active Expired - Lifetime
- 1936-09-28 FR FR47692D patent/FR47692E/en not_active Expired
- 1936-11-23 FR FR813868D patent/FR813868A/en not_active Expired
- 1936-11-23 GB GB32028/36A patent/GB485593A/en not_active Expired
-
1937
- 1937-09-28 US US166224A patent/US2211976A/en not_active Expired - Lifetime
-
1938
- 1938-03-31 NL NL87184A patent/NL50083C/xx active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423185A (en) * | 1939-07-08 | 1947-07-01 | Hydronapthene Corp | Process for the manufacture of coated and impregnated materials |
| DE766083C (en) * | 1940-01-26 | 1954-02-01 | Ig Farbenindustrie Ag | Preparations for refining fiber materials |
| US2418696A (en) * | 1942-03-09 | 1947-04-08 | Courtaulds Ltd | Modifying the dyeing properties of cellulose or cellulose derivative textile materials |
| US2451426A (en) * | 1943-11-25 | 1948-10-12 | Du Pont | Bright zinc plating |
| US2594384A (en) * | 1946-11-12 | 1952-04-29 | Monsanto Chemicals | Fungi and bacteria resistant papermakers' felts and process for preparing same |
| US2600698A (en) * | 1948-11-13 | 1952-06-17 | Monsanto Chemicals | Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound |
Also Published As
| Publication number | Publication date |
|---|---|
| GB463300A (en) | 1937-03-22 |
| BE418549A (en) | |
| DE762964C (en) | 1953-11-30 |
| US2211976A (en) | 1940-08-20 |
| GB467166A (en) | 1937-06-08 |
| NL50083C (en) | 1941-04-15 |
| BE417657A (en) | |
| NL44056C (en) | 1938-09-15 |
| FR47692E (en) | 1937-06-16 |
| NL45055C (en) | 1939-02-15 |
| FR806170A (en) | 1936-12-09 |
| BE415480A (en) | 1936-06-30 |
| GB463472A (en) | 1937-03-22 |
| GB485593A (en) | 1938-05-23 |
| US2165265A (en) | 1939-07-11 |
| FR813868A (en) | 1937-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2111698A (en) | Process or preparing hydrophobic cellulose fibers | |
| US2418696A (en) | Modifying the dyeing properties of cellulose or cellulose derivative textile materials | |
| US3038820A (en) | Process for imparting a soft feel to textile fibers | |
| GB882743A (en) | A process for improving textile fabrics | |
| US3590100A (en) | Methods of producing and applying textile finishes and finishes produced by such methods | |
| US2220508A (en) | Improving the wash-fastness of sizes with aminomethylamide derivatives | |
| US2301509A (en) | Fixation of sizes | |
| US3304312A (en) | Imidazolidinones | |
| US2833674A (en) | Compositions for the treatment of textiles, the textiles obtained and processes for the treatment thereof | |
| US2887409A (en) | Substituted guanamine-formaldehyde reaction products and the process for treating textiles therewith | |
| US3676053A (en) | Method of modifying fibrous materials | |
| GB683410A (en) | Production of impregnating agent for treating fibres or fibrecontaining substances and objects | |
| US3168415A (en) | Textile finishing composition, application process, and resulting product | |
| US2990298A (en) | Textile treatment process | |
| US3309363A (en) | Das triazine brightener | |
| US3002859A (en) | Compositions, textiles treated therewith and processes for the treatment thereof | |
| US3766083A (en) | Fluorescent whitening compositions | |
| AT156252B (en) | Process for the production of hydrophobic cellulose fibers. | |
| US3510452A (en) | Antistatic materials | |
| US2371892A (en) | Permanent finish for textiles | |
| US2838425A (en) | Method of protecting cellulose fibers against microorganisms and fungi and the resulting product | |
| US2822312A (en) | Microbicidal composition material impregnated therewith and method of impregnation | |
| US2375124A (en) | Process for modifying the dyeing and other properties of cellulosic textile materials | |
| US3487088A (en) | Process for preparing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone | |
| US3043718A (en) | Compositions, textiles treated therewith, and processes for the treatment thereof |