Hydrophilicized blocked polyisocyanates

• US 7,220,814 B2
• Filed: 12/17/2003
• Issued: 05/22/2007
• Est. Priority Date: 12/20/2002
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer Materialscience AG (Covestro AG)
• Inventors: Feller, Thomas, Rische, Thorsten, Naujoks, Karin, Gurtler, Christoph
• Primary Examiner(s): Sergent; Rabon
• Application Number:
  US10/738,504
• Publication Number:
  US 20040138403A1
• Time in Patent Office: 1,252 Days
• Field of Search: 252/182.2, 252/182.21, 252/182.22, 524/591, 524/839, 524/840, 524/507, 528/45, 528/71, 560/24, 560/25, 560/26, 560/115, 560/157, 560/158, 564/123, 564/152, 564/159, 564/189, 564/191, 525/440, 525/454, 525/455, 525/457, 525/528, 525/124
• US Class Current: 528/45
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/0828 containing sulfonate groups or groups forming them
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/3821 Carboxylic acids; Esters thereof with monohydroxyl compounds
• CPC Class Codes: C08G 18/3831 containing urethane groups
• CPC Class Codes: C08G 18/706 the liquid medium being water
• CPC Class Codes: C08G 18/8093 Compounds containing active methylene groups
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

The present invention relates to new hydrophilicized blocked polyisocyanates, a process for preparing them and their use.

Claims

1. Polyisocyanates comprising at least one of I) or ii)

i) nonionically hydrophilicizing groups based on polyalkylene oxide polyethers containing at least 30% by weight ethylene oxide units,

ii) ionically or potentially ionically hydrophilicizing groups which on interaction with water enter into a pH-dependent dissociation equilibrium and are therefore neutral or positively or negatively charged depending on pH,

and

iii) at least one structural unit of the formula (1)

2. The polyisocyanates according to claim 1, wherein the electron-withdrawing group X is an ester, sulphoxide, sulphone, nitro, phosphonate, nitrile, isonitrile or carbonyl group.

3. A process for preparing the polyisocyanates according to claim 1, comprising reacting

A) one or more organic polyisocyanates together with

B) one or more organic compounds having at least one isocyanate-reactive group which have

b1) nonionically hydrophilicizing groups based on polyalkylene oxide polyethers containing at least 30% by weight ethylene oxide units,

and/or

b2) ionically or potentially ionically hydrophilicizing groups which on interaction with water enter into a pH-dependent dissociation equilibrium and are therefore neutral or positively or negatively charged depending on pH,

C) one or more blocking agents comprising at least one OH-acidic cyclic ketone of the general formula (2),

4. A method for producing coating materials, coatings, sizes, adhesives and mouldings comprising adding the polyisocyanate of claim 1 to a composition comprising a film-forming resin.

5. Aqueous solutions or dispersions of polyisocyanates according to claim 1 or 2.

6. Coating compositions comprising

a) one or more polyisocyanates according to claim 1,

b) one or more film-forming resins,

c) optionally, catalysts,

d) optionally, solvents and

e) optionally, auxiliaries and additives.

7. Coatings obtained from coating compositions according to claim 6.

8. Substrates coated with coatings according to claim 7.

9. The process of claim 3, wherein the polyisocyanates in A) are selected from the group consisting of 1,4-diisocyanatobutane, 1,5-diisocyanatopentane, 1,6-diisocyanatohexane, 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4-trimethyl-1,6-diisocyanatohexane, 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3-diisocyanatocyclohexane, 1,4-diisocyanatocyclohexane, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 4,4′

-diisocyanato-dicyclohexylmethane, triisocyanatononane, ω

,ω

′

-diisocyanato-1,3-dimethyl-cyclohexane, 1-isocyanato-1-methyl-3-isocyanatomethyl-cyclohexane, 1-isocyanato-1-methyl-4-isocyanatomethyl-cyclohexane, bis-(isocyanato-methyl)norbornane, 1,5-naphthalene diisocyanate, 1,3-bis-(2-isocyanatoprop-2-yl)benzene, 1,4-bis-(2-isocyanatoprop-2-yl)benzene, 2,4-diisocyanatotoluene, 2,6-diiso-cyanatotoluene, 2,4′

-diisocyanatodiphenylmethane, 4,4′

-diisocyanato-diphenylmethane, 1,5-diisocyanatonaphthalene, 1,3-bis(isocyanatomethyl)benzene and mixtures thereof.

10. The process of claim 3, wherein the CH-acidic cyclic ketone of the general formula (2) is selected from the group consisting of cyclopentanone-2-carboxy-methyl ester, cyclopentanone-2-carboxyethyl ester, cyclopentanone-2-carbon itrile, cyclohexanone-2-carboxymethyl ester, cyclohexanone-2-carboxyethyl ester, and cyclopentanone-2-carbonylmethane.

11. The process of claim 3, wherein the catalysts are selected from the group consisting of sodium carbonate, trisodium phosphate, 1,4-diazabicyclo [2.2.2]octane, potassium carbonate, zinc 2-ethylhexanonate, and mixtures thereof.

12. The coating composition according to claim 6, wherein the film-forming resins b) are selected from the group consisting of epoxy functional polyester polymers, polyurethanes, acrylic polymers, vinyl polymers, polyurethane dispersions, polyacrylate dispersions, polyurethane-polyacrylate hybrid dispersions, polyvinyl ether dispersions, polyvinyl ester dispersions, polystyrene dispersions, polyacrylonitrile dispersions, and mixtures thereof.