Aromatic alcohol-lignin-aldehyde resins and processes for making and using same
View Patent ↗Aromatic alcohol-lignin-aldehyde resins and process for making and using same. In some examples, a process for making a resin can include heating a first mixture that includes a lignin, an aromatic alcohol, and a base compound to produce a second mixture that can include an activated lignin, the aromatic alcohol, and the base compound. The second mixture can be heated with an aldehyde to produce a third mixture that can include an aromatic alcohol-lignin-aldehyde resin and unreacted free aldehyde. In some examples, an aromatic alcohol-lignin-aldehyde resin can be or include a co-polymer of an activated lignin, an aromatic alcohol, and an aldehyde. A weight ratio of the activated lignin to the aromatic alcohol can be about 20:80 to about 95:5.
1. A process for making a resin, comprising:
heating a first mixture comprising a lignin starting material, an aromatic alcohol, and a base compound to produce a second mixture comprising an activated lignin, the aromatic alcohol, and the base compound, wherein the lignin starting material is separated from a black liquor, and wherein a weight ratio of the lignin starting material to the base compound in the first mixture is from 60:40 to 77:23; and
heating the second mixture and an aldehyde to produce a third mixture comprising an aromatic alcohol-lignin-aldehyde resin and unreacted free aldehyde.
2. The process of claim 1 , further comprising reacting at least a portion of the unreacted free aldehyde in the third mixture and an aldehyde scavenger to produce a fourth mixture comprising the aromatic alcohol-lignin-aldehyde resin and the unreacted free aldehyde, wherein an amount of the unreacted free aldehyde in the fourth mixture is less than an amount of the unreacted free aldehyde in the third mixture.
3. The process of claim 2 , wherein the aldehyde scavenger comprises urea, an aminotriazine, a cycloaliphatic guanamine, 2-cyanoguanidine, ammonium hydroxide, sodium sulfite, sodium bisulfite, or a mixture thereof.
4. The process of claim 1 , wherein the aromatic alcohol comprises an aromatic alcohol having a chemical structure of R—(OH) n , wherein R is an aromatic group of 6 to 24 carbon atoms, and n is an integer of 1 to 15, wherein the base compound comprises an oxide of an alkali metal, an oxide of an alkaline earth metal, a hydroxide of an alkali metal, a hydroxide of an alkaline earth metal, a carbonate of an alkali metal, a carbonate of an alkaline earth metal, a tertiary amine, a tertiary amino alcohol, or a mixture thereof, and wherein the lignin starting material comprises a kraft lignin, a lignosulfonate, or a mixture thereof, and wherein the lignin starting material comprises sulfur.
5. The process of claim 1 , wherein the first mixture is heated at a temperature of about 40° C. to about 100° C. for about 10 minutes to about 6 hours to produce the second mixture, and wherein the second mixture and the aldehyde are heated at a temperature of about 50° C. to about 100° C. for about 20 minutes to about 8 hours to produce the third mixture.
6. The process of claim 1 , wherein a weight ratio of the lignin starting material to the base compound in the first mixture is from 65:35 to 75:25.
7. The process of claim 1 , wherein:
a total amount of the aldehyde heated with the second mixture to produce the third mixture is combined with the second mixture in a single aldehyde addition step over a period of time without the addition of any additional base compound to the second mixture prior to combining the total amount of the aldehyde or during the addition of the total amount of the aldehyde,
a weight ratio of the lignin starting material to the aromatic alcohol in the first mixture is from 20:80 to 40:60,
a weight ratio of the lignin starting material to the base compound in the first mixture is from 65:35 to 75:25,
the lignin starting material is a kraft lignin, a lignosulfonate, or a mixture thereof, and
the lignin starting material comprises 1 wt % to 10 wt % of sulfur based on the dry weight of the lignin.
8. The process of claim 1 , wherein the lignin starting material comprises 1 wt % to 10 wt % of sulfur based on the dry weight of the lignin.
9. The process of claim 1 , wherein the aromatic alcohol-lignin-aldehyde resin has a molar ratio of aldehyde to (aromatic alcohol+activated lignin) of at least 1.8:1, and wherein a calculation of the molar ratio is based on an average molecular weight of 180 grams per mole for the lignin monomer unit starting material prior to activation of the lignin.
10. The process of claim 9 , wherein the molar ratio of aldehyde to (aromatic alcohol+activated lignin) is at least 2:1.
11. The process of claim 1 , the aromatic alcohol-lignin-aldehyde resin has a solids content of about 40 wt % to about 60 wt % based on a weight of the aromatic alcohol-lignin-aldehyde resin, and a viscosity of at least 700 cP to about 1,500 cP at a temperature of about 25° C., as measured according to ASTM D1084-16.
12. The process of claim 1 , wherein:
the aromatic alcohol-lignin-aldehyde resin has a molar ratio of aldehyde to (aromatic alcohol+activated lignin) of at least 1.9:1 to about 2.6:1, wherein a calculation of the molar ratio is based on an average molecular weight of 180 grams per mole for the lignin monomer unit starting material prior to activation of the lignin,
the aromatic alcohol-lignin-aldehyde resin has a solids content of about 40 wt % to about 60 wt % based on a weight of the aromatic alcohol-lignin-aldehyde resin, and a viscosity of at least 600 cP to about 1,500 cP at a temperature of about 25° C., as measured according to ASTM D1084-16, and
a weight ratio of the lignin starting material to the base compound in the first mixture is from 65:35 to 75:25.
13. A process for making an aromatic alcohol-lignin-aldehyde resin comprising:
heating a first mixture comprising a lignin starting material, an aromatic alcohol, and a base compound to produce a second mixture comprising an activated lignin, the aromatic alcohol, and the base compound, wherein the lignin starting material is separated from a black liquor, wherein a weight ratio of the lignin starting material to the aromatic alcohol in the mixture is about 20:80 to about 95:5 and wherein a weight ratio of the lignin starting material to the base compound in the first mixture is from 60:40 to 77:23; and
heating the second mixture and an aldehyde to produce a third mixture comprising the aromatic alcohol-lignin-aldehyde resin and unreacted free aldehyde.
14. The process of claim 13 , wherein the lignin starting material comprises a kraft lignin, a lignosulfonate, or a mixture thereof, wherein the lignin starting material comprises 1 wt % to 10 wt % of sulfur based on the dry weight of the lignin, and wherein the weight ratio of the lignin starting material to the base compound in the mixture is from 60:40 to 75:25.
15. The process of claim 13 , wherein the aromatic alcohol-lignin-aldehyde resin has a solids content of about 40 wt % to about 60 wt % based on a weight of the aromatic alcohol-lignin-aldehyde resin, and a viscosity of at least 600 cP to about 1,500 cP at a temperature of about 25° C., as measured according to ASTM D1084-16.
16. The process of claim 13 , wherein the aromatic alcohol-lignin-aldehyde resin has a molar ratio of aldehyde to (aromatic alcohol+activated lignin) of at least 1.8:1 to about 2.6:1, wherein a calculation of the molar ratio is based on an average molecular weight of 180 grams per mole for the lignin monomer unit starting material prior to activation of the lignin, and wherein the weight ratio of the lignin starting material to the base compound in the mixture is from 60:40 to 75:25.
17. The process of claim 13 , wherein the aromatic alcohol-lignin-aldehyde resin has a solids content of about 40 wt % to about 60 wt %, based on a weight of the aromatic alcohol-lignin-aldehyde resin, a viscosity of at least 700 cP to about 1,500 cP at a temperature of about 25° C., as measured according to ASTM D1084-16, and a gel time of about 20 minutes to about 30 minutes at a temperature of about 100° C.
18. The process of claim 13 , wherein the lignin starting material is a kraft lignin, a lignosulfonate, or a mixture thereof, and wherein the lignin starting material comprises 1 wt % to 10 wt % of sulfur based on the dry weight of the lignin.
19. The process of claim 13 , wherein the weight ratio of the lignin starting material to the aromatic alcohol in the mixture is from 20:80 to 35:65.