# US 8,569,423 B2 · Triazine derivatives and a method for their production

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- Number: US 8,569,423 B2
- Document ID: US8569423B2
- Status: Granted
- Kind: B2
- Application number: 12/599,243
- Filed: 2008-05-29
- Published: 2010-11-18
- Granted: 2013-10-29
- Earliest claimed: 2008-05-29
- Assignees: Borealis Agrolinz Melamine GmbH
- Applicants: Rene Dicke; Martin Burger; Christoph Hahn; Andreas Endersfelder; Clemens Schwarzinger; Klaus Bretterbauer; Harald Schmidt
- Inventors: Rene Dicke; Martin Burger; Christoph Hahn; Andreas Endersfelder; Clemens Schwarzinger; Klaus Bretterbauer; Harald Schmidt
- Web page: https://patentgrep.com/patent/US8569423B2

## CPC

- C07D 251/70: Other substituted melamines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to triazine derivatives of the general formula (I), their use and production.

## Claims

### Claim 1

Triazine derivatives according to the general formula (Ia)
wherein
R3 means Q1 or a moiety of the formula R5—N—R6 connected with the nitrogen atom to the triazine ring of the structure of formula (I), wherein
Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or of an imide of a cyclic saturated or unsaturated carboxylic acid, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
R4 means a moiety of the formula R7—N—R8 connected with the nitrogen atom to the triazine ring of the structure of the formula (Ia),
R1, R5, and R7 mean independently from each other H or Q2, wherein
Q2 means in each case a linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, that in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
A means —NR2—, —NR62— or —NR82—,
R6 means H, Q2-CO-A-R2, —CO-A-R61,
R8 means —CO-A-R2, —CO-A-R61 or —CO-A-R81
R2, R61, R62, R81 and R82 mean independent from each other Q2, a moiety of a substituted or non-substituted alcohol, a moiety of a substituted or unsubstituted polyvalent alcohol, a moiety of an amine, a moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II)
whereby R9 means Q2,
with the stipulation that in case R3 means R5—N—R6 and R4 means R7—N—R8,
at least one of the moieties R1, R5, and R7 means Q2 and is bound to a nitrogen atom that is covalently connected to the moiety —CO-A-R2, —CO-A-R61 or —CO-A-R81, or
at least the moieties R5 and R6 on the one hand and the moieties R7 and R8 on the other hand mean in each case Q2
or mixtures thereof.

### Claim 2 (depends on 1)

Triazine derivatives according to claim 1, wherein the moieties R2, R61, R62, R81 and R82 are identical.

### Claim 3 (depends on 1)

Triazine derivatives according to claim 1, wherein they have at least one of an adjustable viscosity or an adjustable melting behaviour or an adjustable compatibility to other compounds.

### Claim 4 (depends on 1)

Triazine derivatives according to claim 1, wherein at least one of the moieties R1, R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4.

### Claim 5 (depends on 1)

Triazine derivatives according to claim 1, wherein at least one of the moieties R1, R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4 and are bound to a nitrogen atom which is covalently linked to the moiety —CO-A-R2, —CO-A-R61 or —CO-A-R81.

### Claim 6 (depends on 1)

Triazine derivatives according to claim 1, wherein at least one of the moieties R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4.

### Claim 7 (depends on 1)

Triazine derivatives according to claim 1, wherein the cyclic substituent has a nitrogen atom as part of the cyclic structure via which it is bound to the triazine ring of the structure of the formula (Ia).

### Claim 8 (depends on 1)

Triazine derivatives according to claim 1, wherein each of the nitrogen atoms bound to the triazine ring of the structure of the formula (I) (Ia) is substituted in the same manner so that structural symmetrical triazine derivatives are provided.

### Claim 9 (depends on 1)

Triazine derivatives according to claim 1, wherein R2, R61, R62, R81 and R82 are independently from each other a moiety of methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, benzylalcohol, phenol, ethylenglycolmonomethylether, ethylhexylalcohol, dodecylalcohol and/or stearylalcohol.

### Claim 10 (depends on 1)

Triazine derivatives according to claim 1, wherein R2, R61, R62, R81 and R82 are independently from each other a moiety of the compound 2-hydroxyethylacrylate, 2-hydroxypropylacrylate, 4-hydroxybutylacrylate, 6-hydroxyhexyl-acrylate, diethylenglycolmonoacrylate, triethylenglycolmonoacrylate, dipropylenglycol-monoacrylate, tripropylenglycol-monoacrylate, trimethylolpropandiacrylate, pentaerythrit-diacrylate, pentaerythrittriacrylate, 2-hydroxyethylmethacrylate, 2-hydroxypropylmeth-acrylate, 4-hydroxybutylmethacrylate, 6-hydroxyhexylmethacrylate, diethylenglycol-monomethacrylate, triethylenglycol-monomethacrylate, dipropylenglycolmonometh-acrylate, tripropylenglycol-monomethacrylate, trimethylolpropandimethacrylate, penta-erythritdimethacrylate, penta-erythrittrimethacrylate and/or 4-hydroxybutylvinylether.

### Claim 11 (depends on 1)

Triazine derivatives according to claim 1, wherein R2, R61, R62, R81 and R82 are independently from each other a moiety of ethylenglycol, butandiol, neopentylglycol, hexandiol, octandiol, dodecandiol, octadecandiol, glycol, trimethylolpropane, pentaerythrit, of polyethylenglycoles with molar masses of 200 to 5000, of polypropylenglycoles with molar masses of 200 to 5000, of polytetrahydrofuranes with molar masses of 200 to 5000 and/or of polyesterdioles on the basis of saturated dicarboxylic acids like terephthalic acid, isophthalic acid, naphthalindicarboxylic acid, maleinic acid, fumaric acid and/or itakonic acid.

### Claim 12 (depends on 1)

Triazine derivatives according to claim 1, wherein R2, R61, R62, R81 and R82 are independently from each other a moiety of ethylamine, diethylamine, propylamine, dipropylamine, isopropylamine, diisopropylamine, butylamine, dibutylamine, hexylamine, hexamethylendiamine, propylendiamine, butylendiamine and/or ethylendiamine.

### Claim 13 (depends on 1)

Triazine derivatives according to claim 1, wherein R2, R61, R62, R81 and R82 are independently from each other a moiety of aminoethanol, aminopropanol, aminoethoxyethanol, diethanolamine, triethanolamine, triisopropanol-amine, diisopropanolamine and/or isopropanolamine.

### Claim 14 (depends on 1)

Triazine derivatives according to claim 1, wherein at least one en of the moieties R1, R5, R6, R7 and R8 have a C1-C18-alkyl group.

### Claim 15 (depends on 1)

Triazine derivatives according to claim 1, wherein the moiety R6 or the moiety R8 or both have only the meaning of Q2, but not the meaning of CO-A-R2, —CO-A-R61 or —CO-A-R81.

### Claim 16 (depends on 1)

Triazine derivatives according to claim 1, wherein the triazine derivatives are polymerizable by radiation.

### Claim 17 (depends on 16)

Triazine derivatives according to claim 16, wherein the radiation is electromagnetical radiation or particle radiation.

### Claim 18 (depends on 1)

Triazine derivatives according to claim 1, wherein the triazine derivatives are polymerizable chemically or thermally or both.

### Claim 19 (depends on 1)

Triazine derivatives according to claim 1, wherein the triazine derivatives are polymerizable by polycondensation or polyaddition.

### Claim 20 (depends on 1)

Triazine derivatives according to claim 1, wherein the triazine derivatives are present as oligomers or polymers or both.

### Claim 21 (depends on 20)

Triazine derivatives according to claim 20, wherein at least two triazine derivative monomers are connected to each other via polyvalent alcohols, amines or amino alcohols.

### Claim 22 (depends on 1)

A composition, comprising triazine derivatives according to claim 1 with at least one urea resin, urea-melamine resin, melamine resin, melamine-phenol-resin, phenol resin, polyester, polyacrylate, polyurethane, epoxide, polyether, or mixture thereof.

### Claim 23 (depends on 1)

Triazine derivatives according to claim 1, wherein the triazine derivatives are present as oligomers or polymers or both.

### Claim 24 (depends on 23)

Triazine derivatives according to claim 23, wherein at least two triazine derivative monomers are connected to each other via polyvalent alcohols, amines or amino alcohols.

### Claim 25

A method for the production of triazine derivatives of general formula (I),
wherein
R3′ means Q1 or a moiety of the formula R5′—N—R6′ connected with the nitrogen atom to the triazine ring of the structure of formula (I), wherein
Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or of an imide of a cyclic saturated or unsaturated carboxylic acid, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
R4′ means Q1 or a moiety of the formula R7′—N—R8′ connected with the nitrogen atom to the triazine ring of the structure of the formula (I),
R1′, R5′, and R7′ mean independently from each other H or Q2, wherein
Q2 means in each case a linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, that in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
A′ means —O—, —NH—, —NR2′—, —NR62′— or —NR82′—,
R6′ and R8′ mean independent from each other means H, Q2-CO-A-R2′, —CO-A-R61′, —CO-A-R81′,
R2′, R61′, R62′, R81′ and R82′ mean independent from each other Q2, a moiety of a substituted or non-substituted alcohol, a moiety of a substituted or unsubstituted polyvalent alcohol, a moiety of an amine, moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II),
whereby R9′ means Q2,
with the stipulation that in case R3′ means R5′—N—R6′ and R4′ means R7′—N—R8′,
at least one of the moieties R1′, R5′, and R7′ means Q2 and is bound to a nitrogen atom that is covalently connected to the moiety —CO-A-R2′, —CO-A-R61′ or —CO-A-R81′, or
at least the moieties R5′ and R6′ on the one hand and the moieties R7′ and R8′ on the other hand mean in each case Q2 or
at least one of the moieties R5′ or R6′ means Q2 and R7′ and R8′ mean both simultaneously H,
or mixtures thereof,
comprising the steps of:
A) converting a triazine derivative according to the general formula (IX)
whereby
R3′ means Q1 or a moiety of the formula R5′—N—R6′ bound with its central nitrogen atom to the triazine ring of the structure of the formula (IX), wherein
Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or an imide of cyclic saturated or unsaturated carboxylic acids, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
R4′ means Q1 or a moiety of the formula R7′—N—R8′ bound with the nitrogen atom to the triazine ring of the structure of the formula (IX),
R1′, R5′, and R7′ independently from each other mean H or Q2, wherein
Q2 means in each case linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, which can be interrupted in each case by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
R6′ and R8′ mean independently from each other H, Q2, —CO-A-R61′ or —CO-A-R81′,
A′ means —O—, —NH— —CO-A-R62′ or —CO-A-R82′,
R61′, R62′, R81′ and R82′ mean independently from each other Q2, a moiety of a substituted or unsubstituted alcohol, a moiety of the substituted or unsubstituted polyvalent alcohol, a moiety of an amine, a moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II),
Whereby R9′ means Q2,
with phosgen and
B) converting the carbamoylchloride of the triazine derivative formed in step A) with a substituted or unsubstituted alcohol of the general formula R2, —OH, a substituted or unsubstituted polyvalent alcohol of the general formula R2′-(OH)n with n≧2, an amine of the general formula R2′—NH2 or R2′—NH—R20′, an amino alcohol of the general formula OH—R2′—NH2 or R2′—NH—R20′—OH, a diamine of the general formula R2′, —(NH2)2 or a moiety of the general formula (II),
whereby R2′ and R20′ mean independently from each other Q2, a moiety of a substituted or unsubstituted alcohol, a moiety of a substituted or unsubstituted polyvalent alcohol, a moiety of an amine, a moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II).

### Claim 26

Triazine derivatives according to the general formula (Ib)
wherein
R3 means Q1 or a moiety of the formula R5—N—R6 connected with the nitrogen atom to the triazine ring of the structure of formula (Ib), wherein
Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or of an imide of a cyclic saturated or unsaturated carboxylic acid, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
R4 means Q1 or a moiety of the formula R7—N—R8 connected with the nitrogen atom to the triazine ring of the structure of the formula (Ib),
R1, R5, and R7 mean independently from each other H or Q2, wherein
Q2 means in each case a linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, that in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
A means —O—,
R6 and R8 mean independent from each other H, Q2-CO-A-R2, —CO-A-R61, —CO-A-R81,
R2, R61, R62, R81 and R82 mean independent from each other a moiety of a substituted or non-substituted alcohol selected from the compounds 2-hydroxyethylacrylate, 2-hydroxypropylacrylate, 4-hydroxybutylacrylate, 6-hydroxyhexyl-acrylate, diethylenglycolmonoacrylate, triethylenglycolmonoacrylate, dipropylenglycol-mono acrylate, tripropylenglycol-monoacrylate, trimethylolpropandiacrylate, pentaerythrit-diacrylate, pentaerythrittriacrylate, 2-hydroxyethylmethacrylate, 2-hydroxypropylmeth-acrylate, 4-hydroxybutylmethacrylate, 6-hydroxyhexylmethacrylate, diethylenglycol-monomethacrylate, triethylenglycol-monomethacrylate, dipropylenglycolmonometh-acrylate, tripropylenglycol-monomethacrylate, trimethylolpropandimethacrylate, penta-erythritdimethacrylate, penta-erythrittrimethacrylate and/or 4-hydroxybutylvinylether or a moiety of the general formula (II),
whereby R9 means Q2,
with the stipulation that in case R3 means R5—N—R6 and R4 means R7—N—R8,
at least one of the moieties R1, R5, and R7 means Q2 and is bound to a nitrogen atom that is covalently connected to the moiety —CO-A-R2, —CO-A-R61 or —CO-A-R81, or
at least the moieties R5 and R6 on the one hand and the moieties R7 and R8 on the other hand mean in each case Q2 or
at least one of the moieties R5 or R6 means Q2 and R7 and R8 mean both simultaneously H,
or mixtures thereof.

### Claim 27 (depends on 26)

Triazine derivatives according to claim 26, wherein they have at least one of an adjustable viscosity or an adjustable melting behaviour or an adjustable compatibility to other compounds.

### Claim 28 (depends on 26)

Triazine derivatives according to claim 26, wherein at least one of the moieties R1, R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4.

### Claim 29 (depends on 26)

Triazine derivatives according to claim 26, wherein at least one of the moieties R1, R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4 and are bound to a nitrogen atom which is covalently linked to the moiety —CO-A-R2, —CO-A-R61 or —CO-A-R81.

### Claim 30 (depends on 26)

Triazine derivatives according to claim 26, wherein at least one of the moieties R5, R6, R7 and R8 mean Q2 independently of the meaning of the moieties R3 and R4.

### Claim 31 (depends on 26)

Triazine derivatives according to claim 26, wherein the cyclic substituent has a nitrogen atom as part of the cyclic structure via which it is bound to the triazine ring of the structure of the formula (Ib).

### Claim 32 (depends on 26)

Triazine derivatives according to claim 26, wherein each of the nitrogen atoms bound to the triazine ring of the structure of the formula (Ib) is substituted in the same manner so that structural symmetrical triazine derivatives are provided.

### Claim 33 (depends on 26)

Triazine derivatives according to claim 26, wherein at least one of the moieties R1, R5, R6, R7 and R8 have a C1-C18-alkyl group.

### Claim 34 (depends on 26)

Triazine derivatives according to claim 26, wherein the moiety R6 or the moiety R8 or both have only the meaning of Q2, but not the meaning of CO-A-R2, —CO-A-R61 or —CO-A-R81.

### Claim 35 (depends on 26)

Triazine derivatives according to claim 26, wherein the triazine derivatives are polymerizable by radiation.

### Claim 36 (depends on 35)

Triazine derivatives according to claim 35, wherein the radiation is electromagnetical radiation or particle radiation.

### Claim 37 (depends on 26)

Triazine derivatives according to claim 26, wherein the triazine derivatives are polymerizable chemically or thermally or both.

### Claim 38 (depends on 26)

Triazine derivatives according to claim 26, wherein the triazine derivatives are polymerizable by polycondensation or polyaddition.