Compositions and methods to produce alkoxylated triazine-arlhydroxy-aldehyde condensates

Patent metadata

Field	Value
Publication number	US-10640475-B2
Application number	US-201816043707-A
Country	US
Kind code	B2
Filing date	Jul 24, 2018
Priority date	Sep 22, 2017
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

The embodiments described herein generally relate to methods and chemical compositions of triazine-arylhydroxy-aldehyde condensates. In one embodiment, a triazine-arylhydroxy-aldehyde condensate is reacted with at alkoxylation agent to form alkoxylated triazine-arylhydroxy-aldehyde condensates.

First claim

What is claimed is:

1. A condensation product of a reaction mixture comprising: a 1,3,5-triazine-arylhydroxy-aldehyde condensate and alkoxylation by an alkoxylation agent comprising: an alkylene oxide; and an optional alkylene carbonate; and an optional catalyst, wherein the alkylene oxide is an epoxy functional compound and wherein the 1,3,5-triazine moiety of the 1,3,5-triazine-arylhydroxy-aldehyde condensate comprises at least one optionally substituted amino group.

2. The condensation product of claim 1 , wherein the at least one alkylene oxide comprises a compound selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and combinations thereof.

3. The condensation product of claim 1 , wherein the optional alkylene carbonate comprises a compound selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, and combinations thereof.

4. The condensation product of claim 1 , wherein the optional catalyst comprises a compound selected from the group consisting of a metal hydroxide, a metal carbonate, a tertiary amine, a phosphine, a transition metal base, a metal phosphate, an organic acid, and combinations thereof.

5. The condensation product of claim 1 , wherein each reactive site of the 1,3,5-triazine-arylhydroxy-aldehyde condensate possesses from 1 mole to 20 moles of an alkoxylation agent.

6. The condensation product of claim 1 , wherein the condensation product comprises an alkoxylated triazine-arylhydroxy-aldehyde condensate having a structure of:

wherein R 6 is Formula II or Formula III, and wherein R 7 is a hydrogen atom, Formula II, or Formula IV;
wherein R 8 and R 9 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula II), —N(Formula II)(Formula IV), —N(Formula II) 2 , —NH(Formula III), —N(Formula III)(Formula IV), —N(Formula III) 2 , NH(Formula V), —N(Formula IV)(Formula V), —N(Formula V) 2 , or NH 2 ;

wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or an alkyl group with 1 to 4 carbon atoms containing a hydroxyl group;
wherein R 10 is a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 10 carbon atoms containing a hydroxyl group, a phenyl group, a vinyl group, a propenyl group, a hydroxyl containing phenyl group, a pyrrole group, or a (uranyl group;
wherein R 11 and R 12 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxybenzene group, or an alkyl group with 1 to 10 carbon atoms with at least one carbon substituted with i) a hydroxyl group, ii) a hydroxybenzene group, or iii) a phenyl group;
or wherein R 11 and R 12 jointly form a common aromatic ring with or without a hydroxyl group;
wherein R 13 and R 14 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula V), —N((Formula IV)(Formula V)), —N(Formula V) 2 , or NH 2 ;
wherein R 15 , R 16 , and R 17 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula V), —N(Formula IV)(Formula V), —N(Formula V) 2 , or —NH 2 ;
wherein each m is independently from 1 to 10, each n is independently from 0 to 10,
wherein each x is independently from 1 to 20, and each x′ is independently from 1 to 20 when an alkoxylation agent is an alkylene oxide or wherein each x is independently from 1 to 20, and each x is independently from 1 to 20 with the average of all x and x′ is greater than 2 when the alkoxylation agent is a combination of an alkylene oxide and an alkylene carbonate,
and wherein monomers depicted by m and n are arranged in any order, combination, or sub-combination.

7. The condensation product of claim 1 , wherein the condensation product comprises one or more compounds selected from the group consisting of:

and combinations thereof.

8. The condensation product of claim 1 , wherein the condensation product comprises a nitrogen content from about 1 wt. % to 41 wt. %.

9. The condensation product of claim 1 , wherein the condensation product comprises an aromatic content from about 1 up to 69 weight percent.

10. An alkoxylated triazine-arylhydroxy-aldehyde condensate compound having a structure of:

wherein R 6 is Formula II or Formula III, and wherein R 7 is a hydrogen atom, Formula II, or Formula IV;
wherein R 8 and R 9 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula II), —N(Formula II)(Formula IV), —N(Formula II) 2 , —NH(Formula III), —N(Formula III)(Formula IV), —N(Formula III) 2 , NH(Formula V), —N(Formula IV)(Formula V), —N(Formula V) 2 , or —NH 2 ;

wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or an alkyl group with 1 to 4 carbon atoms containing a hydroxyl group;
wherein R 10 is a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 10 carbon atoms containing a hydroxyl group, a phenyl group, a vinyl group, a propenyl group, a hydroxyl containing phenyl group, a pyrrole group, or a (uranyl group;
wherein R 11 and R 12 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxybenzene group, or an alkyl group with 1 to 10 carbon atoms with at least one carbon substituted with i) a hydroxyl group, ii) a hydroxybenzene group, or iii) a phenyl group;
or wherein R 11 and R 12 jointly form a common aromatic ring with or without a hydroxyl group;
wherein R 13 and R 14 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula V), —N((Formula IV)(Formula V)), —N(Formula V) 2 , or —NH 2 ;
wherein R 15 , R 16 , and R 17 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, —NH(Formula IV), —N(Formula IV) 2 , —NH(Formula V), —N(Formula IV)(Formula V), —N(Formula V) 2 , or —NH 2 ;
wherein each m is independently from 1 to 10, each n is independently from 0 to 10,
wherein each x is independently from 1 to 20, and each x′ is independently from 1 to 20 when an alkoxylation agent is an alkylene oxide or wherein each x is independently from 1 to 20, and each x′ is independently from 1 to 20 with the average of all x and x′ is greater than 2 wh

Assignees

• Hexion Inc

Inventors

• Viswanathan Ganapathy S
• Maiorana Anthony
• Schröter Stephan
• Kukkala Pravin

Classifications

• C08G18/7664

  containing alkylene polyphenyl groups · CPC title

• C07D251/48

  Two nitrogen atoms · CPC title

• C07D251/64 Primary

  Condensation products of melamine with aldehydes; Derivatives thereof (polycondensation products C08G) · CPC title

• C07D251/18

  with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines · CPC title

• C07D317/38

  Ethylene carbonate · CPC title