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US4042567A Expired / Lapsed US ⏱️ 0.0 years remaining

S-Triazine prepolymers and a process for their production

Assignee: Bayer AG
•
Filing: 1975-11-28
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Granted: 1977-08-16
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Expires: 1995-11-28
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Abstract

Abstract S-Triazine prepolymers with aromatic cyanate groups are obtained by condensation of aromatic di- or polyhydroxy compounds with 0.01 to 0.5 mol of 4,6-dichloro-s-triazine per one hydroxy group. Subsequently the condensation products are reacted with cyanogen halide in the presence of a base. s-Triazine prepolymers may be polymerized to form hard plastics with resistance to high temperature.

Inventors

  • 👤 Rudolf Sundermann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 10:42
CPC Classifications
C; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/26; C07D251/30; C07D251/34; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 353 words
A process for producing an s-triazine prepolymer which comprises condensing an aromatic polyhydroxy compound with 0.01 to less than 1/2 mol of a 4,6-dichloro-s-triazine per hydroxy group of said polyhydroxy compound and subsequently reacting the product of said condensation with a halogen cyanide in the presence of a base, the molar ratio of hydroxy groups to cyanogen halide to base being about 1:1:1, said condensation being carried out in the melt at a temperature of 100° to 250° C. or in solution or suspension in the presence of about 1 mol of base per mol of hydrogen chloride to be eliminated at a temperature of from about 0° to 150° C., said reaction of said condensation product with cyanogen halide in the presence of a base being carried out at a temperature of from -40° to 65° C., each of said bases being selected from the group consisting of tertiary amines, alkali metal hydroxides, alkali metal carbonates and alkali metal alcoholates, said polyhydroxy compound being of the formula ##STR11## wherein a is 1, 2 or 3, b is 5 - a; c is 5 - d; d is 1, 2 or 3 with the proviso that a + d is from 2 to 4 if n is 0 and is 2 to 6 if n is 1; n is 0, 1, 2 or 3; R is hydrogen, halogen, alkyl or phenyl; A is --O--, --SO 2 --, --CO--, ##STR12## a CH 2 chain having up to 6 carbon atoms, a CH 2 chain having up to 6 carbon atoms substituted by lower alkyl, a CH 2 chain having up to 6 carbon atoms substituted by phenyl, a divalent cycloaliphatic or aromatic 5- or 6-membered ring or a single bond and R 1 is the same as R or ##STR13## wherein A and R are as defined above, e is 1, 2 or 3 and f is 5-e and said 4,6-dichloro-s-triazine is of the formula ##STR14## wherein n' is 0 or 1; Z is hydrogen, alkyl or aryl; X is --O--, --S--, --NH-- or --NZ'-- and Z and Z' are alkyl, cycloalkyl or aryl.
Claim 2
Dependent Claim 353 words
A process for producing an s-triazine prepolymer which comprises condensing an aromatic polyhydroxy compound with 0.01 to less than 1/2 mol of a 4,6-dichloro-s-triazine per hydroxy group of said polyhydroxy compound and subsequently reacting the product of said condensation with a halogen cyanide in the presence of a base, the molar ratio of hydroxy groups to cyanogen halide to base being about 1:1:1, said condensation being carried out in the melt at a temperature of 100° to 250° C. or in solution or suspension in the presence of about 1 mol of base per mol of hydrogen chloride to be eliminated at a temperature of from about 0° to 150° C., said reaction of said condensation product with cyanogen halide in the presence of a base being carried out at a temperature of from -40° to 65° C., each of said bases being selected from the group consisting of tertiary amines, alkali metal hydroxides, alkali metal carbonates and alkali metal alcoholates, said polyhydroxy compound being of the formula ##STR11## wherein a is 1, 2 or 3, b is 5 - a; c is 5 - d; d is 1, 2 or 3 with the proviso that a + d is from 2 to 4 if n is 0 and is 2 to 6 if n is 1; n is 0, 1, 2 or 3; R is hydrogen, halogen, alkyl or phenyl; A is --O--, --SO 2 --, --CO--, ##STR12## a CH 2 chain having up to 6 carbon atoms, a CH 2 chain having up to 6 carbon atoms substituted by lower alkyl, a CH 2 chain having up to 6 carbon atoms substituted by phenyl, a divalent cycloaliphatic or aromatic 5- or 6-membered ring or a single bond and R 1 is the same as R or ##STR13## wherein A and R are as defined above, e is 1, 2 or 3 and f is 5-e and said 4,6-dichloro-s-triazine is of the formula ##STR14## wherein n' is 0 or 1; Z is hydrogen, alkyl or aryl; X is --O--, --S--, --NH-- or --NZ'-- and Z and Z' are alkyl, cycloalkyl or aryl.
Claim 3
Dependent Claim 22 words
The process of claim 1 wherein said condensation is carried out in the melt at a temperature of 150° to 200° C.
Claim 4
Dependent Claim 25 words
The process of claim 1 wherein said condensation is carried out in solution or suspension at a temperature of from 0° to about 100° C.
Claim 5
Dependent Claim 26 words
The process of claim 1 wherein the product of said condensation is reacted with said cyanogen halide at a temperature of from 0° to 30° C.
Claim 6
Dependent Claim 10 words
An s-triazine prepolymer prepared by the process of claim 1.

References Cited (Backward Citations)

US2481156A Cited
US3108029A Cited
US3654192A Cited
US3960783A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-15 1981-02-14 1981-08-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-15 1985-02-14 1985-08-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-15 1989-02-14 1989-08-16 $7700.00 Window Closed / Lapsed

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