US3650671A - Process for finishing cellulosic textile materials with n-methylol compounds - Google Patents
Process for finishing cellulosic textile materials with n-methylol compounds Download PDFInfo
- Publication number
- US3650671A US3650671A US807402A US3650671DA US3650671A US 3650671 A US3650671 A US 3650671A US 807402 A US807402 A US 807402A US 3650671D A US3650671D A US 3650671DA US 3650671 A US3650671 A US 3650671A
- Authority
- US
- United States
- Prior art keywords
- cross
- acid
- linking
- acetic acid
- textile material
- 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
- 239000004753 textile Substances 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims description 53
- 238000004132 cross linking Methods 0.000 claims abstract description 60
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229960004319 trichloroacetic acid Drugs 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 26
- -1 nitrogen-containing methylol compound Chemical class 0.000 claims abstract description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920000742 Cotton Polymers 0.000 claims abstract description 5
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229950005308 oxymethurea Drugs 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000004744 fabric Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 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 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- 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 invention relates to the finishing of textiles in the process of wet, damp or dry cross-linking with nitrogen-containing methylol compounds.
- the acid catalysis has the effect of causing the reaction of the methylol group with the hydroxyl group of the cellulose, which has the effect of cross-linking the cellulose.
- crosslinking catalysts there are used inorganic acids, such as hydrochloric acid alone or in combination with suitable organic acids.
- the dry cross-linking method it is conventional to carry out the process in the presence of salts which are acid-reacting under the effect of heat. After the cross-linking step has been carried out, it is necessary in the wet or damp cross-linking process to neutralize the acids and to remove them from the textile goods in order to avoid damaging the fibers, which could result from an extended effect of the acids thereon. In contrast to the dry cross-linking method, it is necessary in the damp or wet cross-linking process to follow with an additional past-processing step as well as with a second drying step, which both are required as a result of the required abovediscussed neutralization. Accordingly, this procedure requires additional chemicals and drying energy.
- the object of the invention is to overcome the drawbacks of the known method.
- a method is provided whereby two steps in the above-described conventional process are omitted, namely, the neutralization step and the following required drying step.
- thermally unstable acids such as organic acids like trichloracetic acid, mesoxalic acid, propiolic acid, tetrolic acid, acetoacetic acid, ethanetricarbonic acid or malonic acid. These acids may be used in amounts of to 50 g./l.
- organic acids like trichloracetic acid, mesoxalic acid, propiolic acid, tetrolic acid, acetoacetic acid, ethanetricarbonic acid or malonic acid.
- these acids may be used in amounts of to 50 g./l.
- Preferred amongst the various organic, heat-sensitive acids is trichloracetic acid because it decomposes into chloroform and carbon dioxide at a temperature in the range of about 80 to 100 C., in a time dependent reaction.
- the salts of this acid form carbonate.
- trichloracetic acid in combination with one of its salts, the acid residue is neutralized concurrently with the decomposition of the acid-forming carbonate of the acid. In this manner, it is possible to shorten the duration of the necessary time for the heat treatment when causing a neutral textile reaction.
- Any salt of trichloracetic acid which is heat decomposable can be used including the metal salts thereof like alkaline-, alkaline-earth-, ammonium-, aluminum-, amine-, heavy metal-, sodium or potassium salts.
- hydrochloric acid phosphoric acid, tartaric acid, and an alkane sulfonic acid or aryl sulfonic acid like ethane or toluene sulfonic acids.
- the decomposition of the acid is accomplished by subjecting the mixture to a short heat treatment at a temperature of about 130 to 140 C.
- the decomposition of the thermally unstable acid, after it has effectuated its function as a cross-linker, can also be effectuated by holding the temperature at elevated temperatures for a longer period of time.
- the textile which is impregnated with the cross-linking catalyst for the synthetic resin and with the conventional additives be cured by subjecting it to a holding period after it has been reduced to a residual water content. Then the textile is subjected to a short additional thermal post-treatment.
- the thermal post-treatment can also follow directly the drying to the desired residual humidity and, thus the holding or curing period can be omitted.
- the drying and the heat treatment of the impregnated textile goods can be carried out in one process step.
- composition of the acid-salt mixture is so selected that after the thermal treatment in accordance with the invention, an alkaline reaction of the fiber is established.
- chloroform vapors which are generated upon the decomposition of trichloracetic acid are removed in accordance with conventional procedures used in finishing textiles, such as by suction from the dry goods so that the process can be carried out under all the requisite safety requirements.
- the invention involves the use of a heat-decomposable acid or its salts in a known process in substitution for the known acidic catalysts.
- a heat-decomposable acid or its salts are particularly well suited.
- those acids or their salts which decarboxylate into gases, such as CO upon heating to about C. or higher and which therefore are the equivalent of trichloracetic acid or malonic acid and their respective salts.
- oxalic acid and its salts can be used.
- EXAMPLE 1 A mercerized and bleached cotton fabric is treated with 200 g./l. of a 50% dimethyloldihydroxyethylene urea 35 g./l. of trichloracetic acid, and
- the impregnated fabric is heated to C. for 20 seconds, dried to a residual water content of 8% and, after a 20-hour curing period, the fabric is subjected for one minute to a temperature of C.
- EXAMPLE 3 Another similar cotton textile material is treated as above, the catalyst mixture is trichloracetic acid in an amount of 20 g./l.
- the products exhibit upon a neutral reaction the characteristic values for a wet cross-linking.
- the acid content of the textile pieces showed a loss of only 10% under the stated conditions.
- the major amount of the tri-chloracetic acid was removed upon the thermal post-treatment which followed.
- the amount of acid used can vary over wide ranges such as to 80 g./l., preferably to 50 g./l. of the liquid mixture for treating the textile.
- the potassium salt thereof can be used.
- EXAMPLE 6 The same fabric as in Example 1 is treated with a catalyst mixture of I50 g./l. ofa 50% methylolacryl amide 20 g./l. of trichloracetic acid, and
- the fabric is foulardised, dried at 80 C., subjected to a thermal treatment at 150 C. for 5 minutes and steamed at 43 p.s.i. for 2 minutes.
- Example l is repeated using 36.5 g./l. of sodium salt of trichloracetic acid and 10 g./l. ofoxalic acid, or
- a textile finishing process by cross-linking a textile material comprising a cellulosic textile by the reaction with a resin-forming, cross-linking nitrogen-containing methylol compound in the presence of an acid cross-linking catalyst
- the improvement which comprises carrying out said crosslinking reaction in the presence of an acid cross-linking catalyst selected from the following: trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa cross-linking acid and a salt of trichloro acetic acid, and heating the cross-linked textile material to decompose the crosslinking catalyst, thereby eliminating subsequent neutralization of the cross-linked textile material.
- a process for the finishing of a textile material comprising a cellulosic textile, the steps which comprise impregnating the textile material with an aqueous solution comprising a cross-linking, resin'forming, nitrogen-containing methylol compound and an acid cross-linking catalyst selected from the group consisting of trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa thermally unstable cross-linking acid and a salt of trichloro acetic acid and heating and drying the impregnated textile material to cause cross-linking of the textile material with the nitrogencontaining methylol compound and to decompose the crosslinking catalyst.
- an acid cross-linking catalyst selected from the group consisting of trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa thermally unstable cross-linking acid and a salt of trichloro acetic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1719546A DE1719546C3 (de) | 1968-03-16 | 1968-03-16 | Verfahren zur Hochveredlung von Textilien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3650671A true US3650671A (en) | 1972-03-21 |
Family
ID=5689709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US807402A Expired - Lifetime US3650671A (en) | 1968-03-16 | 1969-03-14 | Process for finishing cellulosic textile materials with n-methylol compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3650671A (es) |
| AT (1) | AT301484B (es) |
| BE (1) | BE729664A (es) |
| CH (1) | CH235169D (es) |
| DE (1) | DE1719546C3 (es) |
| FR (1) | FR2004050A1 (es) |
| GB (1) | GB1221751A (es) |
| NL (1) | NL6904030A (es) |
| SE (1) | SE366784B (es) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849066A (en) * | 1972-09-13 | 1974-11-19 | Us Agriculture | Method of increasing covering power of knitted cotton fabric |
| US3910760A (en) * | 1973-05-14 | 1975-10-07 | Us Agriculture | Azeotropic solvents for permanent press treatments of cotton and cotton blend fabrics |
| US3933426A (en) * | 1972-10-07 | 1976-01-20 | Ciba-Geigy Corporation | Process for making textiles containing cellulose crease-resistant |
| WO2007136384A1 (en) * | 2006-05-19 | 2007-11-29 | The Procter & Gamble Company | Textile benefit compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2616983C2 (de) * | 1976-04-17 | 1978-12-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zum gemeinsamen Fixieren und Kondensieren von Pigmentdrucken bzw. Klotzfärbungen und Hochveredlungsprodukten |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837512A (en) * | 1954-11-03 | 1958-06-03 | Du Pont | Activated cellulose ethers and process of preparing same |
| US3120507A (en) * | 1959-10-23 | 1964-02-04 | Ici Ltd | Dyestuffs having a pyrimidine ring substituted by two halogen atoms and by a cyano group in the 5-position |
| US3518042A (en) * | 1966-04-28 | 1970-06-30 | Stevens & Co Inc J P | Storable polymeric compositions and processes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR887537A (fr) * | 1941-11-20 | 1943-11-16 | Spinnfaser Ag | Procédé d'amélioration de filés en cellulose hydratée par un traitement à la formaldéhyde en solution |
| NL107002C (es) * | 1952-06-04 | 1900-01-01 | ||
| NL243632A (es) * | 1958-09-24 | |||
| US3138802A (en) * | 1962-05-25 | 1964-06-30 | Cotton Producers Inst Of The N | Process for imparting durable creases, wrinkle resistance and shape retention to cellulosic textile articles |
| FR1491628A (fr) * | 1965-08-10 | 1967-08-11 | Basf Ag | Procédé perfectionné pour l'apprêtage irrétrécissable et sans repassage des tissus |
-
0
- CH CH235169D patent/CH235169D/xx unknown
-
1968
- 1968-03-16 DE DE1719546A patent/DE1719546C3/de not_active Expired
-
1969
- 1969-02-24 AT AT182669A patent/AT301484B/de not_active IP Right Cessation
- 1969-03-10 BE BE729664D patent/BE729664A/xx unknown
- 1969-03-12 GB GB03085/69A patent/GB1221751A/en not_active Expired
- 1969-03-12 FR FR6907010A patent/FR2004050A1/fr active Granted
- 1969-03-14 NL NL6904030A patent/NL6904030A/xx unknown
- 1969-03-14 US US807402A patent/US3650671A/en not_active Expired - Lifetime
- 1969-03-14 SE SE03610/69A patent/SE366784B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837512A (en) * | 1954-11-03 | 1958-06-03 | Du Pont | Activated cellulose ethers and process of preparing same |
| US3120507A (en) * | 1959-10-23 | 1964-02-04 | Ici Ltd | Dyestuffs having a pyrimidine ring substituted by two halogen atoms and by a cyano group in the 5-position |
| US3518042A (en) * | 1966-04-28 | 1970-06-30 | Stevens & Co Inc J P | Storable polymeric compositions and processes |
Non-Patent Citations (1)
| Title |
|---|
| J. T. Marsh, Crease Resisting Fabrics, 1962, Reinhold Publishing Corp., New York, pp. 112 119. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849066A (en) * | 1972-09-13 | 1974-11-19 | Us Agriculture | Method of increasing covering power of knitted cotton fabric |
| US3933426A (en) * | 1972-10-07 | 1976-01-20 | Ciba-Geigy Corporation | Process for making textiles containing cellulose crease-resistant |
| US3910760A (en) * | 1973-05-14 | 1975-10-07 | Us Agriculture | Azeotropic solvents for permanent press treatments of cotton and cotton blend fabrics |
| WO2007136384A1 (en) * | 2006-05-19 | 2007-11-29 | The Procter & Gamble Company | Textile benefit compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE729664A (es) | 1969-08-18 |
| DE1719546A1 (de) | 1969-11-27 |
| DE1719546C3 (de) | 1975-08-28 |
| CH235169D (es) | |
| FR2004050B1 (es) | 1975-01-10 |
| SE366784B (es) | 1974-05-06 |
| DE1719546B2 (de) | 1975-01-16 |
| FR2004050A1 (fr) | 1969-11-21 |
| NL6904030A (es) | 1969-09-18 |
| AT301484B (de) | 1972-09-11 |
| GB1221751A (en) | 1971-02-10 |
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