IP Library Granted Patent US 7,005,002
Granted Patent B2
US 7,005,002 · App. 10/838,238 · Granted Feb 28, 2006

Branched, amorphous, polyester-based macropolyols of narrow molecular weight distribution

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Quick Facts
Patent No.
US 7,005,002
App. No.
10/838,238
Granted
Feb 28, 2006
Kind
B2
Abstract

Branched, amorphous, polyester-based macropolyols having a narrow molecular weight distribution and a process for making the macropolyol.

Claims (72)

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.

Assignments (6)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
CHANGE OF NAME Recorded Feb 23, 2010
From: DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 024006/0127 →
CHANGE ADDRESS Recorded Feb 22, 2010
From: EVONIK DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 023985/0296 →
CHANGE OF ENTITY Recorded Feb 22, 2010
From: DEGUSSA AG
To: DEGUSSA GMBH
Reel/Frame 023998/0937 →
RECORD TO CORRECT ASSIGNOR #1'S NAME ON AN ASSIGNMENT PREVIOUSLY RECORDED ON REEL/FRAME 015296/0570. Recorded Nov 18, 2004
From: GLOECKNER, PATRICK; FRANZMANN, GISELHER; SCHMITTHENNER, MARTIN
To: DEGUSSA AG
Reel/Frame 015997/0562 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2004
From: GLOEKNER, PATRICK; FRANZMANN, GISELHER; SCHMITTHENNER, MARTIN
To: DEGUSSA AG
Reel/Frame 015296/0570 →