SE516275C2 - New oligomer compound and use thereof - Google Patents

Abstract

A new oligomer compound of formula (I) where a) R is (II) or b) R is CH2 = CH - O - and where n is 2-6 and the use of the oligomer in UV curable lacquers and powder coatings.

Description

516 275 (curing) in charged transfer induces polymerization in which hydrogen release is highly involved. It is well known that hydrogen next to heteroatoms such as oxygen, nitrogen, etc. are easily released. Accordingly, it is likely that this will occur if, for example, cellulose is included in the surface to be coated by this polymerization process.

* Coatings that do not turn yellow can be obtained.

* The polymerization can be carried out at any temperature, which is an advantage when applied to sensitive materials and surfaces (furniture, etc.). _ * The polymerization can be carried out locally by deworming (cf. photo proliferation).

* The total polymerization time for this type of system is relatively short and within parts of seconds up to minutes for full conversion of reactive groups.

* Investment costs are considered to be quite low.

* The space occupied by UV equipment is relatively minimized.

The units which make up the bulk of the molecular weight and which determine the properties contribute most to the mechanical properties of the cured coating. Improvements regarding abrasion, scratch and water resistance as well as improved gloss and general appearance can be obtained by coating modification with UV technology. The final properties of a surface are obtained by the character of the functional groups in the molecule and their distribution, molecular weight, excitability, etc. In

A novel bismaleimide oligomer according to an embodiment of the invention can be manufactured as schematically shown in fi g. 1 below.

Fig. 1 O [CHÄCHÛ | oCO 2] 25 fl {(CH 3) 3 CH 2] 2 ocN-OCHZONCO + 2 I N- (Cfmno fl -> OO HO o (li i! Lu: v N- (cngno-cN -QCHZAO-Nc- o to form a new bismaleimide hereinafter referred to as BIS-MI-DW.

HEMI can in itself be manufactured according to a pending Swedish patent application.

A novel vinyl ether oligomer according to another embodiment of the invention can be manufactured as schematically shown. 2 below.

Fig2 [CHs (CH2) 10CO2] 25 fl l (CHs) sCH2] 2 ocN-O-cuzßmo + z CHFCH-o- (c flfl nou _ »o H || | _» CHFCH-o- (crigno-c-NQ-CHZ- ONco (cH2> no-cH = cH, wherein n is 2-6, preferably 2-4.

In a specific embodiment, wherein n in the above formula is 2, the vinyl ether oligomer was obtained by mixing Desmodur® W and 2-hydroxyethyl vinyl ether in an organic solvent and under catalytic conditions to form a vinyl ether oligomer hereinafter referred to as BIS-VE-DW.

The invention is further illustrated by working examples 1-3 below, of which Example 1 relates to the reaction between Desmodur® W and HEMI. Example 2 shows the reaction between Desmodur® W and 2-hydroxyethyl vinyl ether. Example 3 shows the use of the novel oligomers of Examples 1 and 2 as reactive components in the manufacture of a UV-curing photoinitiator-free lacquer.

Example 1 HEMI (5 g, 35.4 mmol) was dissolved in acetone. The catalyst shown in fi g. 1, dicyclohexylmethane diisocyanate (Desmodur® W) (4.45 g, 17 mmol) was added dropwise with stirring at room temperature. The reaction mixture was stirred overnight. Acetone was evaporated and the remaining crude product was recrystallized from ethanol / acetone. The product was filtered and washed with ethanol and finally dried under vacuum. 1 H NMR (CDCl 3) confirmed (Table 1 below) the pure bismaleimide (BIS-MI-DW) according to fi g. l where n is 2. The yield was 4.6 g (50% based on Desmodur® W). 516 2.75 4 Table 1 Molecular weight Melting point ° CC% H% N% O% Measured value 544.6 35-75 59.9 6.9 10.3 23.7 Theoretical value 59.6 6.7 10.3 23 Example 2 2-Hydroxyethyl vinyl ether (3.2 g, 35.4 mmol) was dissolved in acetone. The reaction mixture was treated under dry conditions for 2 hours. The catalyst shown in Fig. 2 was added, after which dicyclohexylmethane diisocyanate (Desmodur® W) (4.45 g, 17 mmol) was added dropwise with stirring at room temperature. The reaction mixture was stirred overnight. Acetone was evaporated and the remaining crude product was recrystallized from ethanol / acetone. The product was filtered and washed with ethanol and finally dried under vacuum. 1 H NMR (CDCl 3) confirmed (Table 2 below) the pure vinyl ether oligomer (BIS-VE-DW) according to fi g. 2 where n is 2. The yield was 3.2 g (43% based on Desmodur® W).

Table 2 Molecular weight Melting point ° CC% H% N% O% Measured value 438.2 30-55 63.3 8.9 6.5 21.9 Theoretical value 63.0 8.7 6.4 21.9 Example 3 En mixture at a 50/50 molar ratio was prepared from BIS-MI-DW and BIS-VE-DW. 5 mg of the mixture was added to an aluminum DSC test plate. The sample temperature was raised from 0 ° C to 130 ° C at a rate of 100 ° C / min. The polymerization temperature was 130 ° C and this temperature was maintained for 15 s, 30 s and 45 s and then the lamp source was lit for 60 s.

The polymerization proceeded efficiently without the addition of a photoinitiator system.

The product obtained was transparent and not discolored. 51.6 __ 275 The invention is not limited to shown embodiments as these can be modified in various ways within the invention framework. A new oligomer according to the invention can, for example, be combined with other complementary compounds as it is used for UV-curing photoinitiator-free paints and / or powder coatings.

Claims (4)

516 275 PATENT REQUIREMENTS A new oligomer compound having a formula of t? * f * f 9 R- (cHmo-c-NQCHZON-c-oenzb-R wherein A) R is o N_ o or B) R is CH 2 = CH-O- and wherein n is 2-6. A compound according to claim 1 alternative A) wherein n is 2. A compound according to claim 1 alternative b) wherein n is 2-4. Use of the compound according to any one of claims 1-3, as a reactive component in UV-curing photoinitiator in paints and powder coatings.