GB1033700A - Production of modified phenol-formaldehyde condensation products - Google Patents
Production of modified phenol-formaldehyde condensation productsInfo
- Publication number
- GB1033700A GB1033700A GB2133765A GB2133765A GB1033700A GB 1033700 A GB1033700 A GB 1033700A GB 2133765 A GB2133765 A GB 2133765A GB 2133765 A GB2133765 A GB 2133765A GB 1033700 A GB1033700 A GB 1033700A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- condensation products
- formaldehyde
- reactions
- carbon atoms
- 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
- 239000007859 condensation product Substances 0.000 title abstract 4
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkoxy radical Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 239000002609 medium Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 abstract 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 abstract 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000981 basic dye Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000001022 rhodamine dye Substances 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkali-soluble condensation products are produced by a process wherein (a) at least one phenol and/or naphthol is reacted with (b) formaldehyde or a formaldehyde donor in an alkaline, acid or neutral aqueous medium and the reaction product obtained is reacted in any sequence in an acid, alkaline or neutral aqueous medium with (c) at least one compound which contained at least once the grouping <FORM:1033700/C3/1> in which R1 denotes a hydrogen atom, a hydroxy-methyl group or an alkoxymethyl group having up to 5 carbon atoms in the alkoxy radical and R2 denotes a hydrogen atom, a hydroxymethyl group, an alkoxymethyl group having up to 5 carbon atoms in the alkoxy radical, or an alkyl group having up to 5 carbon atoms, and if desired, with further formaldehyde, and (d) at least one mononuclear aromatic carboxylic or sulphonic acid which may contain hydroxyl or amino groups, aryloxy fatty acids or aliphatic polycarboxylic acids which may contain hydroxyl groups. The reactions are preferably carried out at temperatures between 50 DEG and 100 DEG C. Reactions in an alkaline medium are suitably carried out in sodium or potassium hydroxide, ammonia, ethylamine, diethylamine, triethylamine, diethanolamine or triethanolamine and reactions in an acid medium are suitably carried out in hydrochloric or sulphuric acids. Examples describe the reaction of p-tertiary butyl phenol with formaldehyde or paraformaldehyde, the reaction product of which is further reacted with salicyclic acid and (1) trimethylolmelamine, (2) hexamethylolmelamine, (3) melamine, (4) triaminomelamine, (5) methylmelamine, (6) dicyanodiamide, (9) N-oxymethyl-N1-cyanoguanidine, (10) amoneline, (11) guanine or amonelide. The condensation products above are suitable for use as laking agents for basis dyes. Examples describe compositions prepared from the condensation products above, a copolymer of styrene and a maleic ester and a basic dye which may be an auramine or rhodamine dye in a solvent which is a mixture of ethanol and ethylene glycolmonoethyl ether.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB76861A DE1235942B (en) | 1964-05-21 | 1964-05-21 | Process for the production of alkali-soluble condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1033700A true GB1033700A (en) | 1966-06-22 |
Family
ID=6979239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2133765A Expired GB1033700A (en) | 1964-05-21 | 1965-05-20 | Production of modified phenol-formaldehyde condensation products |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT250981B (en) |
| BE (1) | BE664182A (en) |
| DE (1) | DE1235942B (en) |
| GB (1) | GB1033700A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114044883A (en) * | 2021-12-08 | 2022-02-15 | 浙江万盛股份有限公司 | Cardanol aldehyde amine epoxy resin curing agent containing purine structure and preparation method thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1259348B (en) | 1964-10-08 | 1968-01-25 | Basf Ag | Process for the production of alkali-soluble condensation products |
| DE2843233C2 (en) * | 1978-10-04 | 1985-07-18 | Basf Ag, 6700 Ludwigshafen | Tanning agent and its uses |
| DE2915315A1 (en) * | 1979-04-14 | 1980-10-30 | Cassella Ag | METHOD FOR THE PRODUCTION OF ETHERED METHYLOLAMINOTRIAZINES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE693923C (en) * | 1935-12-06 | 1940-07-22 | I G Farbenindustrie Akt Ges | Process for the preparation of water-soluble condensation products of phenols |
| DE696869C (en) * | 1938-03-30 | 1940-10-01 | I G Farbenindustrie Akt Ges | Process for the production of synthetic tanning agents |
-
1964
- 1964-05-21 DE DEB76861A patent/DE1235942B/en active Pending
-
1965
- 1965-05-19 BE BE664182D patent/BE664182A/xx unknown
- 1965-05-20 GB GB2133765A patent/GB1033700A/en not_active Expired
- 1965-05-21 AT AT464465A patent/AT250981B/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114044883A (en) * | 2021-12-08 | 2022-02-15 | 浙江万盛股份有限公司 | Cardanol aldehyde amine epoxy resin curing agent containing purine structure and preparation method thereof |
| CN114044883B (en) * | 2021-12-08 | 2023-10-03 | 浙江万盛股份有限公司 | Cashew phenol aldehyde amine epoxy resin curing agent containing purine structure and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT250981B (en) | 1966-12-12 |
| BE664182A (en) | 1965-11-19 |
| DE1235942B (en) | 1967-03-09 |
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