Unsaturated compounds containing carbamate terminal groups or urea terminal groups

• US 6,916,854 B2
• Filed: 03/20/2002
• Issued: 07/12/2005
• Est. Priority Date: 03/23/2001
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Schwalm, Reinhold, Meisenburg, Uwe
• Primary Examiner(s): GORR, RACHEL F
• Application Number:
  US10/471,598
• Publication Number:
  US 20040097642A1
• Time in Patent Office: 1,210 Days
• Field of Search: 522/94, 526/300, 525/157
• US Class Current: 522/94
• CPC Class Codes: C08G 18/0819 containing anionic or anionogenic groups
• CPC Class Codes: C08G 18/3831 containing urethane groups
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/7837 containing allophanate groups
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds

Abstract

The invention relates to a compound containing at least one unsaturated, radically or cationically polymerizable group and at least one carbamate terminal group or urea terminal group.

Claims

1. A polyurethane (A), comprising as constituent components:

a) at least one organic aliphatic or cycloaliphatic allophanate group containing polyisocyanate,

b) at least one compound having at least one isocyanate-reactive group and at least one free-radically polymerizable unsaturated group andlor a cationically polymerizable group,

c) at least one compound having at least one isocyanate-reactive group and a carbamate or urea end group,

d) optionally, at least one compound containing at least one isocyanate-reactive group and at least one dispersing group,

e) optionally, at least one compound containing at least two isocyanate-reactive groups, and

f) optionally, compounds other than a) to d) containing at least one isocyanate-reactive group.

2. The polyurethane as claimed in claim 1, further comprising:

(B) at least one compound containing at least one group that can crosslink with the carbamate groups.

3. A polyurethane dispersion, comprising;

(A) a polyurethane as claimed in claim 1, wherein component d) is present,

(B) at least one compound containing at least one group that can crosslink with the carbamate groups,

(C) optionally;

one or more initiators which can be activated photochemically and/or thermally, and

(D) optionally, further typical coatings additives.

4. A coating material comprising a polyurethane dispersion as claimed in claim 3.

5. A polyurethane as claimed in claim 2, wherein component (B) comprises at least one amino resin.

6. A method of coating substrates, which comprises:

radiation-curing a substrate coated with a material comprising the polyurethane as claimed in claim 1 and heat-treating the coated substrate at temperatures up to 160°

C.

7. The method as claimed in claim 6, wherein the heat treatment takes place at a temperature ranging from 60 to 160°

C.

8. The method as claimed in claim 6, wherein the radiation curing is carried out under inert gas.

9. A binder comprising the polyurethane as claimed in claim 1.

10. A material for coating metals or plastics comprising the polyurethane as claimed in claim 1.

11. An automotive paint or automotive topcoat comprising the polyurethane as claimed in claim 1.

12. A coating material comprising:

a polyurethane (A) as claimed in claim 1,

(B) at least one compound having at least one group that can crosslink with the carbamate groups,

(C) optionally, one or more initiators which can be activated photochemically and/or thermally, and

(D) optionally, further typical coatings additives.

13. The polyurethane as claimed in claim 1, wherein said at least one

organic aliphatic or cycloaliphatic allophanate group containing polyisocyanate is prepared by reacting excess amounts of hexamethylene diisocyanate or of isophorone diisocyanate with a polyhydric alcohol selected from the group consisting of trimethylolpropane, neopentyl glycol, pentaerythritol, 1,4-butanediol, 1,6-hexanediol, 1,3-propanediol, ethylene glycol, diethylene glycol, glycerol, 1,2-dihydroxypropane and mixtures thereof such that the allophonate has an NCO content ranging from 12 to 20% by weight and an average NCO functionality of 2.5 to 3.

14. The polyurethane as claimed in claim 1, wherein, per 100 g of compound (b), the compound contains at least 0.01 mol of unsaturated free-radically or cationically polymerizable groups, and, per 100 g of compound (c), the compound contains at least 0.01 mol of carbamate or urea end groups.

15. The polyurethane as claimed in claim 1, wherein compound (d) has the formula:

RG-R³-DG,

wherein RG is at least one isocyanate-reactive group selected from the group consisting of —

OH, —

SH, —

NH₂ and —

NHR⁴, wherein R⁴ is hydrogen or an alkyl group containing 1 to 4 carbon atoms;

DG is at least one dispersing group selected from the group consisting of —

COOH, —

SO₃H, —

PO³H and the anionic forms of these groups; and

R³ is an aliphatic, cycloaliphatic or aromatic radical containing from 1 to 20 carbon atoms.

16. The polyurethane as claimed in claim 1, wherein compound (b) is a carbamate compound of the formula:

R—

O—

(CO)—

NH—

R¹ or a urea compound of the formula;

R—

(NR¹)—

(CO)—

NN—

R², wherein

R is an aliphatic, cycloaliphatic or aromatic radical of 2 to 20 carbon atoms containing at least one isocyanate-reactive group selected from the group consisting of —

OH, —

SH, —

NH₂ and —

NHR⁴, wherein R⁴ is hydrogen or an alkyl group containing 1 to 4 carbon atoms; and

R¹, R² and R⁴ independently of each other are hydrogen or an alkyl group containing 1 to 4 carbon atoms.

17. The polyurethane as claimed in claim 1, wherein components a):

b);

c) are present in a molar ratio amount, per three mole amount of reactive isocyanate group in (a) is;

b) 0.1 to 2.9, and c) 2.9to 0.1.

18. The polyurethane as claimed in claim 17, wherein components a):

b);

c) are present in a molar ratio amount, per three mole amount of reactive isocyanate group in (a) is;

b) 0.5 to 2.8, and c) 0.2 to 2.5.