Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film

Patent metadata

Field	Value
Publication number	US-11021562-B2
Application number	US-201716339763-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Oct 14, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

The present invention provides a polyisocyanate composition and the like that contain a polyisocyanate compound represented by general formula (I), (II), (III) or (IV) (wherein the pluralities of R 11 , R 21 , R 31 and R 41 each independently represent an organic group, at least one of the pluralities of R 11 , R 21 , R 31 and R 41 is a group represented by general formula (V) (wherein each of the plurality of Y 1 independently represents a single bond or the like, R 51 represents a hydrogen atom or the like, and the wavy line indicates a bonding site) or the like, and in general formula (III), R 32 represents a residue in which one hydroxyl group has been removed from a monohydric or polyhydric alcohol).

First claim

The invention claimed is:

1. A polyisocyanate composition comprising polyisocyanate compounds represented by general formula (I) and general formula (II):

wherein in general formulas (I) and (II), pluralities of R 11 and R 21 each independently represent an organic group, at least one of the pluralities of R 11 and R 21 is a group represented by general formula (V), and the pluralities of R 11 and R 21 may be identical or different;

wherein in general formula (V), each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms, and a wavy line indicates a bonding site.

2. The polyisocyanate composition according to claim 1 , comprising polyisocyanate compounds represented by the general formula (I) and the general formula (II), wherein
a molar ratio between iminooxadiazinedione structures and isocyanurate structures is at least 0.01 but not more than 1.5.

3. The polyisocyanate composition according to claim 1 , further comprising a triisocyanate represented by general formula (V)-1:

wherein in general formula (V)-1, each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, and R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms.

4. The polyisocyanate composition according to claim 1 , comprising a polyisocyanate compound represented by the general formula (II), wherein a theoretical reaction rate calculated from an NCO % of the polyisocyanate composition is not more than 47%.

5. The polyisocyanate composition according to claim 1 , comprising a polyisocyanate compound represented by the general formula (II), wherein a theoretical reaction rate calculated from an NCO % of the polyisocyanate composition is at least 95% but not more than 150%.

6. The polyisocyanate composition according to claim 3 , comprising a polyisocyanate compound (A) represented by the general formula (II), and a triisocyanate compound (B) represented by the general formula (V)-1, wherein
a surface area ratio ((A)/[(A)+(B)]) between a peak surface area (A) of a number average molecular weight of the polyisocyanate compound (A) and a peak surface area (B) of a number average molecular weight of the triisocyanate compound (B), obtained by a gel permeation chromatography (GPC) measurement, is at least 0.8 but less than 1.

7. The polyisocyanate composition according to claim 6 , wherein when a monomer trimer which is a triisocyanate represented by the general formula (II) in which all the R 21 groups are represented by the above general formula (V) is deemed to be a compound (C), a peak surface area ratio ((C)/[(A)+(B)] between a peak surface area (A) of a number average molecular weight of the polyisocyanate compound (A), a peak surface area (B) of a number average molecular weight of the triisocyanate compound (B), and a peak surface area (C) of a number average molecular weight of the compound (C), obtained by a gel permeation chromatography (GPC) measurement, is at least 0.3 but less than 1.

8. The polyisocyanate composition according to claim 6 , wherein an isocyanate group functional value is at least 4 but not more than 12.

9. A polyisocyanate composition comprising polyisocyanate compounds represented by general formula (II) and general formula (III), wherein a molar ratio between isocyanurate structures and allophanate structures is within a range from 100/0.1 to 100/15:

wherein in general formula (II) and general formula (III), pluralities of R 21 and R 31 each independently represent an organic group, at least one of the pluralities of R 21 and R 31 is a group represented by general formula (V), the pluralities of R 21 and R 31 may be identical or different, and R 32 represents a residue in which one hydroxyl group has been removed from a monohydric or polyhydric alcohol;

wherein in general formula (V), each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms, and a wavy line indicates a bonding site.

10. The polyisocyanate composition according to claim 9 , further comprising a triisocyanate represented by general formula (V)-1:

wherein in general formula (V)-1, each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, and R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms.

11. A polyisocyanate composition comprising polyisocyanate compounds represented by general formula (II) and general formula (IV), wherein a molar ratio between isocyanurate structures and uretdione structures is within a range from 100/0.1 to 100/100:

wherein in general formulas (II) and (IV), pluralities of R 21 and R 41 each independently represent an organic group, at least one of the pluralities of R 21 and R 41 is a group represented by general formula (V), and the pluralities of R 21 and R 41 may be identical or different;

wherein in general formula (V), each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms, and a wavy line indicates a bonding site.

12. The polyisocyanate composition according to claim 11 , further comprising a triisocyanate represented by general formula (V)-1:

wherein in general formula (V)-1, each of a plurality of Y 1 independently represents a single bond or a divalent hydrocarbon group of 1 to 20 carbon atoms that may contain an ester structure and/or an ether structure, the plurality of Y 1 may be identical or different, and R 51 represents a hydrogen atom or a monovalent hydrocarbon group of 1 to 12 carbon atoms.

13. A polyisocyanate composition comprising a polyisocyanate compound represented by general formula (II):

Assignees

• Asahi Chemical Ind

Inventors

• Azuma Koichiro
• Miwa Yuichi
• Fujimoto Katsuhiro
• Harada Yoshijiro

Classifications

• C08G18/807

  with nitrogen containing compounds · CPC title

• C08G18/285 Primary

  Nitrogen containing compounds · CPC title

• C08G18/8077

  Oximes · CPC title

• C08G18/8064

  with monohydroxy compounds · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title