GB596153A - Chemical substances for textile processing - Google Patents
Chemical substances for textile processingInfo
- Publication number
- GB596153A GB596153A GB1880345A GB1880345A GB596153A GB 596153 A GB596153 A GB 596153A GB 1880345 A GB1880345 A GB 1880345A GB 1880345 A GB1880345 A GB 1880345A GB 596153 A GB596153 A GB 596153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridine
- condensation
- urea
- water
- condensation products
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004753 textile Substances 0.000 title abstract 3
- 239000000126 substance Substances 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 15
- 239000007859 condensation product Substances 0.000 abstract 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000005215 alkyl ethers Chemical class 0.000 abstract 5
- JHOKTNSTUVKGJC-UHFFFAOYSA-N N-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- XKALZGSIEJZJCZ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)urea Chemical compound COCNC(=O)NCOC XKALZGSIEJZJCZ-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- -1 amino-substituted heterocyclic nitrogen compounds Chemical class 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 3
- 230000005494 condensation Effects 0.000 abstract 3
- 239000004744 fabric Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 229920002866 paraformaldehyde Polymers 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-M pyridine;chloride Chemical compound [Cl-].C1=CC=NC=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-M 0.000 abstract 2
- 239000005871 repellent Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- ORGWCTHQVYSUNL-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)thiourea Chemical compound OCNC(=S)NCO ORGWCTHQVYSUNL-UHFFFAOYSA-N 0.000 abstract 1
- MKKIRWHZUWKMEX-UHFFFAOYSA-N 1,3-diethyl-1,3-bis(hydroxymethyl)urea Chemical compound CCN(CO)C(=O)N(CC)CO MKKIRWHZUWKMEX-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- PSUUXBOOGOCZTN-UHFFFAOYSA-N 1-(hydroxymethyl)-1-octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCN(CO)C(N)=O PSUUXBOOGOCZTN-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 Acetic Acid Drugs 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- 240000007170 Cocos nucifera Species 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N Dipropyl ether Chemical group CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 abstract 1
- 235000019753 Finisher Diet Nutrition 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- ADWLBWZYTZPFOW-UHFFFAOYSA-N NC(=O)N.NC(=O)N.C(O)C=CCO Chemical compound NC(=O)N.NC(=O)N.C(O)C=CCO ADWLBWZYTZPFOW-UHFFFAOYSA-N 0.000 abstract 1
- 229940037312 STEARAMIDE Drugs 0.000 abstract 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M Sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 abstract 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L Sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 abstract 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M Sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 abstract 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 abstract 1
- 238000005108 dry cleaning Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002191 fatty alcohols Chemical class 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000005217 methyl ethers Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical class NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 150000003918 triazines Chemical class 0.000 abstract 1
- ZJHHPAUQMCHPRB-UHFFFAOYSA-N urea urea Chemical compound NC(N)=O.NC(N)=O ZJHHPAUQMCHPRB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 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
- D06M13/322—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
-
- 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
- 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
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
-
- 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
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
-
- 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
- D06M13/35—Heterocyclic compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
New quaternary compounds, useful in textile processing, are prepared from condensation products of primary fatty acid amides, the corresponding mono-acyl ureas and analogous esters of carbamic and allophanic acids with fatty alcohols, or of the methylol derivatives thereof, with lower alkyl ethers of methylol derivatives of compounds containing primary or secondary amino groups and which are capable of resin-forming condensation with formaldehyde as hereinafter defined, by a process comprising heating said condensation products with a salt of a tertiary amine and preferably also simultaneously with formaldehyde until a water-soluble product is obtained. The compounds containing primary or secondary amino groups and capable of resin-forming condensation with formaldehyde are amino-substituted heterocyclic nitrogen compounds other than melamine, amides of polybasic carboxylic acids, urea and thiourea and substituted ureas and thioureas; the term "lower alkyl ether" is defined as being a methyl, ethyl, propyl or butyl ether. The process may be effected at a temperature between 40 DEG and 80 DEG C. and in the presence of an organic solvent such as benzene, pyridine, triethylamine and dioxane; the tertiary amine whose salt is used in the process may serve as the solvent. The water-soluble products decompose on heating. They may be applied to textile fabrics, especially those containing cellulosic fibres, by impregnating the fabrics with a solution or suspension of one or more of the substances in water or a volatile organic liquid and subsequently submitting the impregnated fabric to a short heat treatment at an elevated temperature whereby the quaternary compound is decomposed. Water-repellent and crease-resistant finishers are thereby obtained which are resistant to alkaline soap washing and dry cleaning. The presence of an acid-binding agent such as sodium acetate, cyanate or thiocyanate in the impregnating liquid prevents tendering. The quaternary compounds may also be used in conjunction with other crease resistant agents such as dimethylol-urea- or thiourea and their lower alkyl ethers or with the condensation products of formaldehyde with amino diazines or triazines or their lower alkyl ethers; or with solutions of polyvalent metal salts, such as aluminium acetate, or with other water-repellent agents (see Group VIII). In examples: (1) the condensation product of methylol stearamide and N : N1-bis-methoxy methyl uron is heated with paraformaldehyde, pyridine and pyridine hydrochloride and the product isolated by precipitation with acetone; it gives a foaming solution with water; (2) the condensation products of methylol stearamide or stearamide itself and dimethylolurea dimethyl ether are similarly heated with paraformaldehyde, pyridine and pyridine hydrochloride and the products used in the crease resistance and water-repellence treatment of cotton gaberdine in the manner described above; (3) the condensation product of methylol stearyl urea and dimethylol di-ethyl urea is employed as in (1); (4) the condensation products of methylol stearamide and dimethylol urea dimethyl ether and of the amide of coconut fatty acid and N : N1-bis-methoxymethyl uron, respectively, are heated in like manner with paraformaldehyde and the reaction product of pyridine and sodium pyrosulphate; (5) the condensation product of methylol stearamide and dimethylol urea dimethyl ether is similarly heated with formaldehyde, and pyridine and its hydrochloride or pyridine, glacial acetic acid and ethyl acetate. Other condensation products which may be used are those derived from the methyl and ethyl ethers of dimethylol thiourea and dimethylol ethylene di-urea; additional amine salts mentioned are those of trimethylamine, triethylamine, triethanolamine and a - and g -picolines. The condensation products used as starting materials are prepared as described in Specification 593,717. The Provisional Specifications include the use of condensation products derived from the lower alkyl ethers of any compounds containing primary or secondary amino groups and which are capable of undergoing resin-forming condensation with formaldehyde.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR930675D FR930675A (en) | 1945-07-23 | ||
| NL72892D NL72892C (en) | 1945-07-23 | ||
| BE466803D BE466803A (en) | 1945-07-23 | ||
| NL72071D NL72071C (en) | 1945-07-23 | ||
| BE466802D BE466802A (en) | 1945-07-23 | ||
| GB1880445A GB596154A (en) | 1945-07-23 | 1945-07-23 | Chemical substances for textile processing |
| FR930722D FR930722A (en) | 1945-07-23 | 1946-07-17 | Chemicals for the treatment of textiles |
| CH259410D CH259410A (en) | 1945-07-23 | 1946-07-22 | Process for the production of a new substance used as a textile treatment agent. |
| CH259409D CH259409A (en) | 1945-07-23 | 1946-07-22 | Process for the production of a new substance suitable as a textile treatment agent. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB596153A true GB596153A (en) | 1947-12-30 |
Family
ID=1734204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1880345A Expired GB596153A (en) | 1945-07-23 | 1945-07-23 | Chemical substances for textile processing |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB596153A (en) |
-
1945
- 1945-07-23 GB GB1880345A patent/GB596153A/en not_active Expired
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