Branched, amorphous, polyester-based macropolyols of narrow molecular weight distribution
View Patent ↗Branched, amorphous, polyester-based macropolyols having a narrow molecular weight distribution and a process for making the macropolyol.
1. A branched macropolyol comprising reacted units of
A) at least one dicarboxylic acid component comprising
1) at least 85 mol % of at least one of a cycloaliphatic 1,2-dicarboxylic acid, an anhydride thereof or an ester thereof, and
2) not more than 15 mol % of at least one of a further dicarboxylic acid, an anhydride thereof or an ester thereof; and
B) at least one alcohol component comprising
1) from 5 to 30 mol % of at least one at least trifunctional alcohol, and
2) from 70 to 95 mol % of at least one further diol,
wherein the branched macropolyol has
a functionality of from 3.5 to 10.0,
an M n of from 2,000 to 10,000 g/mol,
an M w of from 8,000 to 60,000 g/mol,
a polydispersity of from 2.5 to 30,
an OH number of from 0 to 150 mg KOH/g,
an acid number of from 0 to 4.9 mg KOH/g, and
a dynamic viscosity at 65% in a 3:1 mixture of aromatic hydrocarbons having a distillation range of 180 to 207° C. and butyl glycol of from 1,000 to 20,000 mPa·s.
2. The macropolyol as claimed in claim 1 , wherein
the functionality is from 3.5 to 8.0,
the M n is from 2000 to 7000 g/mol,
the M w is from 8000 to 40 000 g/mol,
the polydispersity is from 3 to 25,
the OH number is from 30 to 80 mg KOH/g,
the acid number is from 0 to 3.0 mg KOH/g, and
the dynamic viscosity is from 1,000 to 15,000 mPa·s.
3. The macropolyol as claimed in claim 2 , wherein
the functionality is from 4.0 to 6.0,
the M n is from 2,500 to 4,000 g/mol,
the M w is from 8,000 to 20,000 g/mol,
the polydispersity is from 3.0 to 15,
the OH number is from 40 to 60 mg KOH/g,
the acid number is from 0 to 1.5 mg KOH/g, and
the dynamic viscosity is from 1,000 to 10,000 mPa·s.
4. The macropolyol as claimed in claim 1 , wherein the acid number is from 0 to 3.0 mg KOH/g.
5. The macropolyol as claimed in claim 1 , wherein the OH number is from 30 to 80 mg KOH/g.
6. The macropolyol as claimed in claim 1 , wherein the M n is from 2,000 to 7,000 g/mol and the M w is from 8,000 to 40,000 g/mol.
7. The macropolyol as claimed in claim 1 , wherein the functionality is from 3.5 to 8.0.
8. The macropolyol as claimed in claim 1 , wherein the polydispersity is from 3 to 25.
9. The macropolyol as claimed in claim 1 , wherein the dicarboxylic acid component comprises one or more of 1,2-cyclohexanedicarboxylic acid, methyltetrahydrophthalic acid, tetrahydrophthalic acid, methylhexahydrophthalic acid, an anhydride thereof or a derivative thereof.
10. The macropolyol as claimed in claim 1 , wherein the dicarboxylic acid component comprises at least one of 1,2-cyclohexanedicarboxylic acid or a derivative thereof.
11. The macropolyol as claimed in claim 1 , wherein the further dicarboxylic acid is one or more of an aromatic acid, an aliphatic acid, a cycloaliphatic monocarboxylic acid, a dicarboxylic acid, a polycarboxylic acid or a derivative thereof.
12. The macropolyol as claimed in claim 1 , wherein the further dicarboxylic acid is at least one of phthalic acid, isophthalic acid, terephthalic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, succinic acid, sebacic acid, dodecanedioic acid, adipic acid, azelaic acid, pyromellitic acid, trimellitic acid, isononanoic acid, 2-ethylhexanoic acid or a derivative thereof.
13. The macropolyol as claimed in claim 1 , wherein the dicarboxylic acid component comprises one or more anhydrides or low molecular weight alkyl esters.
14. The macropolyol as claimed in claim 1 , wherein the alcohol component comprises at least one of trimethylolpropane, trimethylolethane, 1,2,6-trihydroxyhexaerythritol, glycerol, tris-hydroxyethyl isocyanurate, pentaerythritol, sorbitol, xylitol or mannitol.
15. The macropolyol as claimed in claim 1 , wherein the alcohol component comprises at least one of trimethylolpropane, trimethylolethane, or tris-hydroxyethyl isocyanurate.
16. The macropolyol as claimed in claim 1 , wherein the alcohol component comprises one or more of a further aliphatic, cycloaliphatic, or aromatic diol or polyol.
17. The macropolyol as claimed in claim 1 , wherein the alcohol component comprises one or more of ethylene glycol, 1,2-propanediol, 1,3-propanediol, diethylene, dipropylene, triethylene alcohol, tetraethylene glycol, 1,2-butanediol, 1,4-butanediol, 1,3-butylethylpropanediol, 1,3-methylpropanediol, 1,5-pentanediol, bisphenol A, bisphenol B, bisphenol C, bisphenol F, norbornylene glycol, 1,4-benzyldimethanol,1,4-benzyldidimethyl-2-ethylhexane-1,3-diol, cyclohexanedimethanol, Dicidol, hexanediol or neopentyl glycol.
18. The macropolyol as claimed in claim 1 , wherein the acid number is from 0 to 1.5 mgKOH/g.
19. The macropolyol as claimed in claim 1 , wherein the OH number is from 40 to 60 mgKOH/g.
20. The macropolyol as claimed in claim 1 , wherein the M n is from 2,500 to 4,000 g/mol, and an M w of from 8,000 to 20,000 g/mol.
21. The macropolyol as claimed in claim 1 , wherein the functionality is from 4.0 to 6.0.
22. The macropolyol as claimed in claim 1 , wherein the polydispersity is from 3 to 15.
23. The macropolyol as claimed in claim 1 , wherein the dicarboxylic acid component comprises one or more of a methylester or an ethylester of a dicarboxylic acid.
24. A process for preparing a branched, amorphous, macropolyol comprising: reacting
A) at least one dicarboxylic acid component comprising
1) at least 85 mol % of at least one of a cycloaliphatic 1,2-dicarboxylic acid, an anhydride or an ester thereof; and
2) not more than 15 mol % of at least one of a further dicarboxylic acid, an anhydride thereof or ester thereof; and
B) at least one alcohol component comprising
1) from 5 to 30 mol % of at least one at least trifunctional alcohol, and
2) from 70 to 95 mol % of at least one further diol, to form a macropolyol having
a functionality of from 3.5 to 10.0,
an M n of from 2,000 to 10,000 g/mol,
an M w of from 8,000 to 60,000 g/mol,
a polydispersity of from 2.5 to 30,
an OH number of from 0 to 150 mg KOH/g,
an acid number of from 0 to 4.9 mg KOH/g, and
a dynamic viscosity at 65% in a 3:1 mixture of aromatic hydrocarbons having a distillation range of 180 to 207° C. and butyl glycol of from 1,000 to 20,000 mPa·s.
25. A macropolyol obtained by the process as claimed in claim 24 .
26. A composition comprising the macropolyol as claimed in claim 1 .
27. The composition as claimed in claim 26 , further comprising at least one of an isocyanate, an isocyanate derivative, or an amine resin.
28. A cured composition comprising the macropolyol as claimed in claim 1 and reacted units of a crosslinker.
29. The cured composition as claimed in claim 28 , wherein the crosslinker is at least one of an isocyanate, an isocyanate derivative, or an amine resin.
30. The composition as claimed in claim 26 , selected from the group consisting of a coating composition, a printing ink, a pigment paste, a tinting paste, a masterbatch, a ballpoint paste, a graphics ink, a polish, an adhesive, a sealant, and an insulant.
31. The composition as claimed in claim 30 , further comprising at least one crosslinker selected from the group consisting of an isocyanate, an isocyanate derivative and an amine resin.