Compositions and methods to produce alkoxylated triazine-arlhydroxy-aldehyde condensates
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.
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 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.
11. The compound of claim 10 , wherein the alkoxylated triazine-arylhydroxy-aldehyde condensate composition comprises one or more compounds selected from the group consisting of having a structure of:
12. The compound of claim 10 , wherein the alkoxylated-triazine-arylhydroxy-aldehyde condensate composition further comprises a rheology modifier in polyurethane crosslinking applications.
13. A process comprising: alkoxylating a 1, 3, 5-triazine-arylhydroxy-aldehyde condensate by reacting with at least one alkylene oxide, alone or in combination with an alkylene carbonate, optionally in the presence of a catalyst; and forming an alkoxylated triazine-arylhydroxy-aldehyde condensate composition, 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.
14. The process of claim 13 , wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and mixtures thereof and in any order.
15. The process of claim 13 , wherein the alkylene oxide is a compound selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and mixtures thereof, and the alkylene carbonate is a compound selected from the group consisting of ethylene carbonate, propylene carbonate and mixtures thereof.
16. The process of claim 13 , wherein manufacturing 1,3,5-triazine-arylhydroxy-aldehyde condensate and forming the alkoxylated 1,3,5-triazine-arylhydroxy-aldehyde condensate composition are carried out in the same reactor.
17. The process of claim 13 , wherein manufacturing triazine-arylhydroxy-aldehyde condensate and forming the alkoxylated 1,3,5-triazine-arylhydroxy-aldehyde condensate composition are carried out in a continuous, semi-continuous, semi-continuous to batch, or batch type reactor.
18. 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, glycidol, styrene oxide, epichlorohydrin, butylene oxide, isobutyleneoxide, cyclohexane oxide, 2,3-epoxyhexane, allyl glycidyl ether, methyl glycidyl ether, butyl glycidyl sulfide, glycidyl methyl sulfone, glycidyl methacrylate, glycidyl allyl phthalate, and combinations thereof.
19. A condensation product of a reaction mixture comprising: a 1,2,3-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 1,2,3-triazine moiety of the 1,2,3-triazine-arylhydroxy-aldehyde condensate comprises at least one optionally substituted amino group.
20. A condensation product of a reaction mixture comprising: a 1,2,4-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 1,2,4-triazine moiety of the 1,2,4-triazine-arylhydroxy-aldehyde condensate comprises at least one optionally substituted amino group.