US4049630A
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Process for preparation of s-triazine prepolymers
Assignee: Bayer AG
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Filing: 1975-11-13
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Granted: 1977-09-20
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Expires: 1995-11-13
Abstract
Abstract Process for the preparation of s-triazine prepolymers which comprises A. condensing a hydroxy compound which has 2 or more alcoholic hydroxyl groups; B. condensing the resulting condensation product with an aromatic hydroxy compound; and C. thereafter reacting the free hydroxyl groups of the condensation product obtained from (b) with cyanogen halide and in the presence of a base.
Inventors
- 👤 Rudolf Sundermann
- 👤 Rolf Putter
- 👤 Ernst Grigat
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:14
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34; C08G18/00; C08G18/06; C08G18/83; C08G18/833; C08G63/00; C08G63/91; C08G63/914; C08G63/916
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
391 words
Process for the preparation of s-triazine prepolymers which comprises a. condensing a hydroxy compound which has 2 or more alcoholic hydroxyl groups corresponding to the formula HO--A--(OH).sub.z (I) in which A denotes an aliphatic, cycloaliphatic or aromatic radical and z denotes an integer which is smaller by at least the number 1 than the number of carbon atoms of the radical A which are capable of substitution with more than 1/3 mol of cyanuric chloride per hydroxyl group at a temperature in the range of 0° to 250° C.; b. condensing the resulting condensation product with an aromatic hydroxy compound selected from the group consisting of compounds corresponding to the formulae ##STR8## in which R denotes hydrogen, halogen, alkyl or phenyl, and it is not necessary for several radicals R to be identical, or two radicals R which are substituents on adjacent carbon atoms can also form, conjointly with these, a carbocyclic or heterocyclic 5-membered or 6-membered ring, a represents one of the numbers 1, 2, or 3 and b represents 5-a and ##STR9## in which X represents oxygen, the sulfonyl group (SO 2 ), the carbonyl group (CO), a CH 2 chain with up to 6 carbon atoms which is optionally substituted by lower alkyl radicals, phenyl, a cycloaliphatic or aromatic 5-membered or 6-membered ring or a single bond and R 1 has the meaning indicated above for R or represents the grouping ##STR10## in which X and R have the abovementioned meaning, e represents one of the numbers 1, 2, or 3, f represents 5-e, c represents 5-d, d denotes one of the numbers 1, 2, or 3 in such a way that more than 1 hydroxyl group equivalent of the aromatic hydroxy compound is used per unconverted chlorine atom of the condensation product obtained from (a) at a temperature in the range of 0° to 250° C.; and c. thereafter reacting the free hydroxyl groups of the condensation product obtained from (b) with cyanogen halide and in the presence of a base selectd from the group consisting of alkali metal hydroxide, alkali metal carbonate, alcoholate and tertiary amine in amounts which correspond to a molar ratio of phenolic hydroxyl groups to cyanogen halide to base in the range of 1:1:1 to a slight excess of cyanogen halide at a temperature in the range of -40° to +65° C.
Claim 2
Dependent Claim
391 words
Process for the preparation of s-triazine prepolymers which comprises a. condensing a hydroxy compound which has 2 or more alcoholic hydroxyl groups corresponding to the formula HO--A--(OH).sub.z (I) in which A denotes an aliphatic, cycloaliphatic or aromatic radical and z denotes an integer which is smaller by at least the number 1 than the number of carbon atoms of the radical A which are capable of substitution with more than 1/3 mol of cyanuric chloride per hydroxyl group at a temperature in the range of 0° to 250° C.; b. condensing the resulting condensation product with an aromatic hydroxy compound selected from the group consisting of compounds corresponding to the formulae ##STR8## in which R denotes hydrogen, halogen, alkyl or phenyl, and it is not necessary for several radicals R to be identical, or two radicals R which are substituents on adjacent carbon atoms can also form, conjointly with these, a carbocyclic or heterocyclic 5-membered or 6-membered ring, a represents one of the numbers 1, 2, or 3 and b represents 5-a and ##STR9## in which X represents oxygen, the sulfonyl group (SO 2 ), the carbonyl group (CO), a CH 2 chain with up to 6 carbon atoms which is optionally substituted by lower alkyl radicals, phenyl, a cycloaliphatic or aromatic 5-membered or 6-membered ring or a single bond and R 1 has the meaning indicated above for R or represents the grouping ##STR10## in which X and R have the abovementioned meaning, e represents one of the numbers 1, 2, or 3, f represents 5-e, c represents 5-d, d denotes one of the numbers 1, 2, or 3 in such a way that more than 1 hydroxyl group equivalent of the aromatic hydroxy compound is used per unconverted chlorine atom of the condensation product obtained from (a) at a temperature in the range of 0° to 250° C.; and c. thereafter reacting the free hydroxyl groups of the condensation product obtained from (b) with cyanogen halide and in the presence of a base selectd from the group consisting of alkali metal hydroxide, alkali metal carbonate, alcoholate and tertiary amine in amounts which correspond to a molar ratio of phenolic hydroxyl groups to cyanogen halide to base in the range of 1:1:1 to a slight excess of cyanogen halide at a temperature in the range of -40° to +65° C.
Claim 3
Dependent Claim
89 words
Process of claim 1 wherein the hydroxy compound used in step (a) has the formula HO--A.sup.1 --(OH).sub.u (IV) wherein A 1 is a straight chain or branched chain aliphatic radical with 2 to 36 carbon atoms or a cycloaliphatic radical both of which are unsubstituted or substituted by substituents which do not themselves react under the conditions of the process and u is an integer which is smaller by at least the number 1 than the number of carbon atoms of the radical A 1 which can be substituted.
Claim 4
Dependent Claim
13 words
Process of claim 2 wherein u is an integer from 1 to 5.
Claim 5
Dependent Claim
27 words
Process of claim 2 wherein A 1 is an aliphatic radical of 2 to 20 carbon atoms or a cycloaliphatic radical of 5 to 18 carbon atoms.
Claim 6
Dependent Claim
66 words
Process of claim 1 wherein the hydroxy compound used in step (a) has the formula ##STR11## wherein R is independently from each other hydrogen, halogen, alkyl or phenyl or two radicals R which are substituents on adjacent carbon atoms can form, conjointly with these carbon atoms, a carbocyclic or heterocyclic 5-membered or 6-membered ring, a is 1, 2 or 3 and b is 5 - a.
Claim 7
Dependent Claim
176 words
Process of claim 1 wherein the hydroxy compound used in step (a) has the formula ##STR12## wherein X is oxygen, SO 2 , CO, a CH 2 chain with up to 6 carbon atoms, which is optionally substituted by C 1 -C 4 alkyl or by phenyl, a cycloaliphatic or aromatic 5-membered or 6-membered ring or a single bond, and R 1 is independently from each other hydrogen, halogen, alkyl or phenyl or two radicals R 1 which are substituents on adjacent carbon atoms can form, conjointly with these carbon atoms, a carbocyclic or heterocyclic 5-membered or 6-membered ring, or R 1 is a group having the formula ##STR13## wherein X is as defined above, R is independently from each other hydrogen, halogen, alkyl or phenyl or two radicals R, which are substituents on adjacent carbon atoms, can form, conjointly with these carbon atoms, a carbocyclic or heterocyclic 5-membered or 6-membered ring, e is 1, 2 or 3, f is 5 - e and c is 5 - d and d is 1, 2 or 3.
Claim 8
Dependent Claim
175 words
Process of claim 1 wherein the compound used in step (a) has the formula ##STR14## wherein C is oxygen, SO 2 , CO, a CH 2 chain with up to 6 carbon atoms, which is optionally substituted by C 1 -C 4 alkyl or by phenyl, a cycloaliphatic or aromatic 5-membered or 6-membered ring or a single bond, and R 2 is independently from each other hydrogen, halogen, alkyl or phenyl or two radicals R 2 , which are substituents on adjacent carbon atoms, can form, conjointly with these carbon atoms, a carbocyclic or heterocyclic 5-membered or 6-membered ring, or R 2 is a group having the formula ##STR15## wherein Y is as defined above, R is independently from each other hydrogen, halogen, alkyl or phenyl or two radicals R, which are substituents or adjacent carbon atoms, can form, conjointly with these carbon atoms, a carbocyclic or heterocyclic 5-membered or 6-membered ring, e is 1, 2 or 3, f is 5 - e c i 5 - d and d is 1, 2 or 3.
Claim 9
Dependent Claim
21 words
Process of claim 1 wherein the hydroxy compound is a polyester, polyether or polyurethane with at least two free hydroxyl groups.
Claim 10
Dependent Claim
17 words
Process of claim 8 wherein the polyester, polyether or polyurethane has two or three free hydroxy groups.
Claim 11
Dependent Claim
36 words
Process of claim 1 wherein the hydroxy compound is condensed in step (a) with cyanuric chloride in solution in the presence of about 1 mol of base per mol of hydrogen chloride to be split off.
Claim 12
Dependent Claim
39 words
Process of claim 1 wherein the condensation product obtained in step (a) is condensed with the aromatic hydroxy compound in solution in the presence of about 1 mol of base per mol of hydrogen chloride to be split off.
Claim 13
Dependent Claim
26 words
Process of claim 10 wherein the base used in step (a) and/or step (b) is an alkali metal hydroxide, alcoholate or carbonate, or a tertiary amine.
Claim 14
Dependent Claim
22 words
Process of claim 10 wherein the condensation reaction in step (a) and/of step (b) is effected at from 0° to 150° C.
Claim 15
Dependent Claim
27 words
Process of claim 1 wherein the condensation reactions in steps (a) and (b) are effected in the melt at a temperature of from 100° to 220° C.
Claim 16
Dependent Claim
19 words
Process of claim 14 wherein the condensation reactions are effected at a pressure of between 0.2 and 0.8 bar.
Claim 17
Dependent Claim
42 words
Process of claim 1 wherein the free hydroxyl groups of the condensation product obtained in step (b) are reacted with a cyanogen halide in step (c) in the presence of a solvent and at a temperature of between 0° and 65° C.
Claim 18
Dependent Claim
23 words
Process of claim 1 wherein the base used in step (c) is an alkali metal hydroxide, alcoholate or carbonate or a tertiary amine.
Claim 19
Dependent Claim
14 words
Process of claim 1 wherein the cyanogen halide is cyanogen bromide or cyanogen chloride.
Claim 20
Dependent Claim
24 words
Process of claim 1 wherein a molar ratio of phenolic hydroxyl groups to cyanogen halide to base of 1:1:1 is employed in step (c).
Claim 21
Dependent Claim
35 words
Process of claim 1 wherein the hydroxy compound is condensed in step (a) with cyanuric chloride in suspension in the presence of about 1 mol of base per mol of hydrogen to be split off.
Claim 22
Dependent Claim
39 words
Process of claim 1 wherein the condensation product obtained in step (a) is condensed with the aromatic hydroxy compound in suspension in the presence of about 1 mol of base per mol of hydrogen chloride to be split off.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-19 | 1981-03-21 | 1981-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-19 | 1985-03-21 | 1985-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-19 | 1989-03-21 | 1989-09-20 | $7700.00 | Window Closed / Lapsed |