# US 2020/0148809 A1 · Process for the preparation of alicyclic polyisocyanate

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- Number: US 2020/0148809 A1
- Document ID: US20200148809A1
- Status: Published application
- Kind: A1
- Application number: 16/614,202
- Filed: 2018-05-07
- Published: 2020-05-14
- Earliest claimed: 2017-05-17
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Frederic LUCAS; Alexander PANCHENKO; Klaus BREUER; Frank HETTCHE; Chee Kean THAM
- Web page: https://patentgrep.com/patent/US20200148809A1

## CPC

- C07C 265/14: containing at least two isocyanate groups bound to the same carbon skeleton
- C07C 265/10: having isocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C08G 18/3206: {aliphatic}
- C08G 18/751: {containing only one cycloaliphatic ring}
- C08G 18/8016: {Masked aliphatic or cycloaliphatic polyisocyanates}
- C08G 18/8025: {Masked aliphatic or cycloaliphatic polyisocyanates}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to a polyisocyanate (P) of general formula (I), the method for preparing polysisocyanate (P) of general formula (I) and the use of polyisocyanate (P) of general formula (I) as crosslinking reagent in clearcoats. The method for preparing polyisocyanate (P) of general formula (I) comprises the reaction of a reaction mixture (RM), which comprises at least one cyclic isocyanate of general formula (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and/or (IIIf) and at least one alcohol having at least two hydroxyl groups, to obtain polyisocyanate (P) of general formula (I).

## Claims

### Claim at position 1

1: A polyisocyanate of formula (I):
where
k, m, n are each independently 0, 1, 2 or 3, wherein a sum total of k, m and n is at least 2 and at most 6; and
L is a linear or branched organic radical having at most 14 carbon atoms, which optionally comprises at least one nitrogen atom and/or at least one oxygen atom,
Ra, Rb, Rc are each independently selected from the group consisting of radicals of formulae (IIa), (IIb), (IIc), (IId), (IIe) and/or (IIf):
where
o is 0 to 10, and
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H, OR5 and unsubstituted or at least monosubstituted C1-C10-alkyl, C5-C12-cycloalkyl, C2-C10-alkenyl and C6-C14-aryl, where R5 is C1-C10-alkyl.

### Claim at position 2 (depends on 1)

2: The polyisocyanate according to claim 1, wherein
L is a linear or branched aliphatic, cycloaliphatic or aromatic radical having at most 14 carbon atoms, which optionally comprises at least one nitrogen atom and/or at least one oxygen atom, and
Ra, Rb, Rc are each independently selected from the group consisting of the radicals of formulae (IIa), (IIb), (IIc), (IId), (IIe) and/or (IIf),
where
o is 0, 2 or 3, and
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H and C1-C10-alkyl.

### Claim at position 3 (depends on 1)

3: The polyisocyanate according to claim 1, wherein
L is a linear or branched aliphatic or cycloaliphatic radical having at most 14 carbon atoms, which optionally comprises at least one nitrogen atom and/or at least one oxygen atom,
Ra, Rb, Rc are each independently selected from the group consisting of the radicals of formulae (IIa), (IIb) and/or (IIc),
where
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H, methyl, ethyl and propyl.

### Claim at position 4 (depends on 1)

4: The polyisocyanate according to claim 1, wherein
k is 2 or 3, and
m, n are 0, and
L is a linear or branched aliphatic radical having at most 10 carbon atoms, which optionally comprises at least one nitrogen atom and/or at least one oxygen atom,
Ra is selected from the group consisting of the radicals of formulae (IIa), (IIb) and/or (IIc):
where
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H, methyl and ethyl,
wherein at least one radical of R1, R1′, R2, R2′, R3, R3′, R4 or R4′ is methyl or ethyl.

### Claim at position 5 (depends on 1)

5: The polyisocyanate according to claim 1, wherein
k is 3, and
m, n are 0, and
L is a linear or branched aliphatic radical having at most 6 carbon atoms, which optionally comprises at least one oxygen atom,
Ra is a radical of the formula (IIb):
where
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H, methyl and ethyl,
wherein at least one radical and at most 3 radicals of R1, R1′, R2, R2′, R3, R3′, R4 or R4′ are methyl or ethyl.

### Claim at position 6

6: A polyisocyanate of formula (IV):
where
R1, R1′, R2, R2′ are each independently selected from the group consisting of H and methyl, wherein at least one radical and at most two radicals of R1, R1′, R2 or R2′ are methyl, and
R3, R3′, R4 and R4′ are H.

### Claim at position 7 (depends on 1)

7: A method for preparing the polyisocyanate according to claim 1, the method comprising reacting a reaction mixture comprising components (a) and (b):
(a) at least one cyclic isocyanate of formulae (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and/or (IIIf):
where
o is 0 to 10, and
R1, R1′, R2, R2′, R3, R3′, R4, R4′ are each independently selected from the group consisting of H, OR5 and unsubstituted or at least monosubstituted C1-C10-alkyl, C5-C12-cycloalkyl, C2-C10-alkenyl and C6-C14-aryl,
where R5 is C1-C10-alkyl, and
(b) at least one alcohol having at least two hydroxyl groups, to obtain a composition (C) comprising the polyisocyanate.

### Claim at position 8 (depends on 7)

8: The method according to claim 7, wherein the component (a) is selected from the group consisting of 1,3-diisocyanatocyclohexane, 1,3-diisocyanato-2-methylcyclohexane, 1,3-diisocyanato-4-methylcyclohexane, 1,3-diisocyanato-5-methylcyclohexane, 1,3-diisocyanato-2-isopropylcyclohexane, 1,3-diisocyanato-4-isopropylcylohexane, 3-diisocyanato-5-isopropylcyclohexane, 1,3-diisocyanato-2,4-dimethylcyclohexane, 1,3-diisocyanato-2,4-diethylcyclohexane, 1,3-diisocyanato-2,4-diethyl-6-methylcyclohexane, 1,3-diisocyanato-2-methyl-4,5-diethylcyclohexane, 1,3-diisocyanato-2,4,6-triisopropylcyclohexane, and 1,3-diisocyanato-2,4,6-tributylcyclohexane.

### Claim at position 9 (depends on 7)

9: The method according to claim 7, wherein the component (b) is selected from the group consisting of ethylene glycol, 1,1-dimethylethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-ethyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,4-butanediol, 2-ethyl-1,4-butanediol, 1,5-pentanediol, 2-methyl-1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 2-ethyl-1,3-hexanediol, 2,4-diethyloctane-1,3-diol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, tripropylene glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, glycerol, cyclohexane-1,2-diol, cyclohexane-1,3-diol, cyclohexane-1,4-diol, 1,1-bis(hydroxymethyl)cyclohexane, 1,2-bis(hydroxymethyl)cyclohexane, 1,3-bis(hydroxymethyl)cyclohexane, 1,4-bis(hydroxymethyl)cyclohexane, 2,2-bis(4-hydroxycyclohexyl)propane, erythritol, threitol, xylitol, adonitol (ribitol), arabitol (lyxitol), sorbitol, mannitol, dulcitol (galactitol), maltitol, isomalt, diglycerol, dimethylolpropane, dipentaerythritol, ribose, arabinose, glucose, mannose, galactose, fructose, pyrocatechol, catechol, hydroquinone, pyrogallol, hydroxyhydroquinone, phloroglucinol, neopentyl glycol hydroxypivalate, triethanolamine, tripropanolamine, 1,3,5-tris(2-hydroxyethyl)cyanuric acid, a polytetrahydrofuran having a molecular weight between 162 and 4500 g/mol, a poly-1,3-propanediol or a polypropylene glycol having a molecular weight between 134 and 2000 g/mol, and a polyethylene glycol having a molecular weight between 238 and 2000 g/mol.

### Claim at position 10 (depends on 7)

10: The method according to claim 7, wherein the component (b) comprises at least two alcohols, at least one alcohol comprises two hydroxyl groups, and at least one alcohol comprises three hydroxyl groups.

### Claim at position 11 (depends on 7)

11: The method according to claim 7, wherein the reaction mixture comprises 70 to 99% by weight of the component (a) and 1 to 30% by weight of the component (b), based on a total weight of components (a) and (b) in the reaction mixture.

### Claim at position 12 (depends on 7)

12: The method according to claim 7, wherein
i) the reaction mixture is reacted at a temperature in the range from 20° C. to 90° C., and/or
ii) the reaction mixture is reacted in the absence of a catalyst.

### Claim at position 13 (depends on 7)

13: The method according to claim 7, further comprising:
terminating the reaction of the reaction mixture by adding at least one component (c), after at least a portion of the components (a) and (b) has been reacted.

### Claim at position 14 (depends on 7)

14: The method according to claim 7, further comprising
terminating the reaction after at least one of the components (a) or (b) has been fully reacted, and/or
separating unreacted amounts of the component (a) and/or (b) from the composition (C).

### Claim at position 15 (depends on 1)

15: A method for crosslinking in a clearcoat, the method comprising:
Introducing the polyisocyanate according to claim 1 as a crosslinking reagent into the clearcoat.

### Claim at position 16 (depends on 13)

16: The method according to claim 13, wherein the at least one component (c) is selected from the group consisting of toluenesulfonic acid, toluolsulfonyl chloride, benzoyl chloride, benzyl chloride, dibutyl prosphite, cibutyl phosphate, and di-12-ethylhexyl phosphate.