GB905609A - Polymeric compounds containing s-triazine nuclei - Google Patents
Polymeric compounds containing s-triazine nucleiInfo
- Publication number
- GB905609A GB905609A GB820558A GB820558A GB905609A GB 905609 A GB905609 A GB 905609A GB 820558 A GB820558 A GB 820558A GB 820558 A GB820558 A GB 820558A GB 905609 A GB905609 A GB 905609A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triazine
- formula
- chloro
- phenyl
- dichloro
- 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
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Polcondensates having either the formula <FORM:0905609/IV(a)/1> or the formula <FORM:0905609/IV(a)/2> in which formulae, R is an alkyl or alkoxy group having 1 to 4 carbon atoms, a phenyl group, an amino group having one or more of these groups as substituents, or a halogen atom; R1 is alkyl of 1 to 4 carbon atoms, phenyl or hydrogen; R2 is phenylene or ethylene or is not present; and n is at least 2, may be prepared by self-condensation by heating of an amino-halo-s-triazine of formula <FORM:0905609/IV(a)/3> or by reacting, either in solution in presence of triethylamine or by direct anhydrous fusion, at least one halo-s-triazine of formula <FORM:0905609/IV(a)/4> with at least one compound R1NH-R2-NHR1. The invention also includes the preparation of cross-linked polycondensates by reacting a polycondensate of formula <FORM:0905609/IV(a)/5> with at least one triazine having at least two replaceable halogen atoms when R is alkylamino or alkoxyamino of 1 to 4 carbon atoms; or with at least one polyfunctional compound containing amino, secondary amino or hydroxyl group when R is a halogen atom; or by reacting together at least one compound of formula <FORM:0905609/IV(a)/6> and at least one compound of formula <FORM:0905609/IV(a)/7> (8) Cyanuric chloride heated with p-phenylene diamine gives a cross-linked resin. (9) Methyl dichloro-s-triazine was reacted with p-phenylene (Z is R or R4NH; and R4 is alkyl of 1 to 4 carbons, phenyl or hydrogen); or by reacting a cyanuric halide with R1NH-R2-NHR1. In the examples, (1) 2-phenyl-4-anilino-6-chloro-s-triazine is self-condensed at 300 DEG C. with elimination of HCl; (2) 2,4-dianilino-6-chloro-s-triazine is similarly condensed. The product is cross-linked with 2-anilino- 4,6-dichloro-s-triazine. similar product may be obtained by direct heating of the mixed monomeric materials. (3) 2-methylamino-4-dimethylamino-6-chloro-s-triazine was auto-condensed. (4) The starting material was 2-methyl-4-anilino-6-chloro-s-triazine. Similarly polycondensates may be prepared by heating 2-methyl-4-methylamino-6-chloro-s-triazine; 2-diphenylamino-4-anilino-6-chloro-s-triazine; 2-phenyl-4-methylamino-6-chloro-s-triazine, or 2-chloro-4,6-bis-ethyl-amino-s-triazine. (5) 2-anilino-4,6-dichloro-s-triazine was self-condensed and the product cross-linked with 2,4-dianilino-6-phenyl-s-triazine (6) 2-phenyl-4-amino-6-chloro-s-triazine heated in nitrogen at 220 DEG -300 DEG C. gave a polymer of formula <FORM:0905609/IV(a)/8> (7) 2-methoxy-4,6-dichloro-s-triazine is condensed with p-phenylenediamine in dioxane containing trialkylamine. The product has the formula <FORM:0905609/IV(a)/9> diamine in acetone solution and in presence of triethylamine to yield a product of formula <FORM:0905609/IV(a)/100> (10) In a similar manner a product of formula <FORM:0905609/IV(a)/111> was produced. (11) Refluxing 2-phenyl-4,6-dichloro-s-triazine with phenylhydrazine in acetone containing triethylamine gave a product of formula <FORM:0905609/IV(a)/122> Similar condensations were effected between phenyl dichloro-s-triazine and m- or p-phenylene diamine or N,N1-dimethyl-p-phenylene diamine; cyanuric chloride and ethylene diamine or phenyl hydrazine.ALSO:The invention comprises polycondensates having either the formula <FORM:0905609/IV (b)/1> or the formula <FORM:0905609/IV (b)/2> in which formulae, R is an alkyl or alkoxy group having 1 to 4 carbon atoms, a phenyl group, an amino group having one or more of these groups as substituents, or a halogen atom; R1 is alkyl of 1 to 4 carbon atoms, phenyl or hydrogen; R2 is phenylene or ethylene or is not present; and n is at least 2. The above polycondensates may be prepared by self-condensation by heating of an amino-halo-s-triazine of formula <FORM:0905609/IV (b)/3> in which X represents a halogen atom, or by reacting, either in solution in presence of triethylamine or by direct anhydrous fusion at least one halo-s-triazine of formula <FORM:0905609/IV (b)/4> in which X represents a halogen atom, with at least one compound R1NH-R2-NHR1. In the examples, (1) 2-phenyl-4-anilino-6-chloro-s-triazine is self-condensed at 300 DEG C. with elimination of HCl. (2) 2,4-dianilino-6-chloro-s-triazine is similarly condensed. (3) 2-methylamino - 4-dimethylamine-6-chloro-s-triazine was auto-condensed. (4) The starting material was 2-methyl-4-anilino-6-chloro-s-triazine. Similarly polycondensates may be prepared by heating 2-methyl-4-methylamino-6-chloro-s-triazine; 2 - diphenylamino-4-anilino-6-chloro-s-triazine; 2-phenyl-4-methylamino-6-chloro-s-triazine, or 2-chloro-4,6-bisethylamino-s-triazine. (5) 2-anilino-4,6-dichloro-s-triazine was self-condensed. (6) 2-phenyl-4-amino-6-chloro-s-triazine heated in nitrogen at 220-300 DEG C. gave a polymer of formula <FORM:0905609/IV (b)/5> (7) 2-methoxy-4,6-dichloro-s-triazine is condensed with p-phenylenediamine in dioxane containing triethylamine. The product has the formula <FORM:0905609/IV (b)/6> (9) Methyl dichloro-s-triazine was reacted with p-phenylene diamine in acetone solution and in presence of triethylamine to yield a product of formula <FORM:0905609/IV (b)/7> (10) In a similar manner a product of formula <FORM:0905609/IV (b)/8> was produced. (11) Refluxing 2-phenyl-4,6-dichloro-s-triazine with phenylhydrazine in acetone containing triethylamine gave a product of formula <FORM:0905609/IV (b)/9> Similar condensations were effected between phenyl dichloro-s-triazine and m of p-phenylene diamine or N,N1-dimethyl-p-phenylene diamine; cyanuric chloride and ethylene diamine or phenyl hydrazine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB820558A GB905609A (en) | 1958-03-14 | 1958-03-14 | Polymeric compounds containing s-triazine nuclei |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB820558A GB905609A (en) | 1958-03-14 | 1958-03-14 | Polymeric compounds containing s-triazine nuclei |
Publications (1)
Publication Number | Publication Date |
---|---|
GB905609A true GB905609A (en) | 1962-09-12 |
Family
ID=9847892
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB820558A Expired GB905609A (en) | 1958-03-14 | 1958-03-14 | Polymeric compounds containing s-triazine nuclei |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB905609A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4562246A (en) * | 1982-04-08 | 1985-12-31 | American Cyanamid Company | Essentially linear, thermoplastic poly (amino-s-triazines)s and process for the production thereof |
EP0337133A1 (en) * | 1988-03-14 | 1989-10-18 | HIMONT ITALIA S.r.l. | Liquid-crystalline, thermotropic polymers of di-s-triazines |
CN117683197A (en) * | 2023-11-20 | 2024-03-12 | 宁波锐克轮业科技有限公司 | High-temperature-resistant flame-retardant polyurethane material for roller outer ring and preparation method thereof |
-
1958
- 1958-03-14 GB GB820558A patent/GB905609A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4562246A (en) * | 1982-04-08 | 1985-12-31 | American Cyanamid Company | Essentially linear, thermoplastic poly (amino-s-triazines)s and process for the production thereof |
EP0337133A1 (en) * | 1988-03-14 | 1989-10-18 | HIMONT ITALIA S.r.l. | Liquid-crystalline, thermotropic polymers of di-s-triazines |
CN117683197A (en) * | 2023-11-20 | 2024-03-12 | 宁波锐克轮业科技有限公司 | High-temperature-resistant flame-retardant polyurethane material for roller outer ring and preparation method thereof |
CN117683197B (en) * | 2023-11-20 | 2024-06-11 | 宁波锐克轮业科技有限公司 | High-temperature-resistant flame-retardant polyurethane material for roller outer ring and preparation method thereof |
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