Lactame or amino acid-based fatty amide, and use as an organogelator

Abstract

The invention relates to a fatty amide, which is based on: a) a diamine selected from aromatic or cycloaliphatic or linear C.sub.2 to C.sub.10 aliphatic diamines, b) a C.sub.3 to C.sub.12 lactam or amino acid, c) optionally, a second primary diamine different from said diamine a), d) a hydroxylated fatty monoacid, e) optionally, a nonhydroxylated monoacid chosen from linear C.sub.6 to C.sub.12 aliphatic acids,
with a mole ratio b/(a+c) of 0.25 to 3/1. The invention also covers a process for the preparation of said amide and its use as organogelator or rheology additive in an organic solvent medium, in particular in coating, glue or adhesive, mastic, sealant or stripping agent compositions or molding or cosmetic compositions.

Claims

1. A fatty amide derived from the reaction of: a) a primary diamine selected from the group consisting of aromatic, cycloaliphatic and linear C2 to C10 aliphatic diamines, b) a C3 to C12 lactam or amino acid, c) optionally, a second primary diamine different from said diamine a) chosen from the group consisting of linear C2 to C10 aliphatic diamines, d) a hydroxylated fatty C18 or C20, monoacid, e) optionally, a nonhydroxylated monoacid chosen from the group consisting of linear C6 to C12 aliphatic acids, the mole ratio e/d of said monoacid e) with respect to said monoacid d) not exceeding 0.5, and in that the mole ratio b/(a+c) is from 0.25 to 3/1.

2. The fatty amide of claim 1 wherein said monoacid d) is 12 hydroxystearic acid.

3. The fatty amide of claim 1 wherein the mole ratio b/(a+c) is from 0.25 to 2/1.

4. The fatty amide of claim 1 wherein said diamine a) is selected from the group consisting of aromatic diamines.

5. The fatty amide of claim 4 wherein said amine a) is an aromatic diamine selected from the group consisting of: xylylenediamines phenylenediamines, and toluylenediamines.

6. The fatty amide of claim 5 wherein said diamine is xylylenediamine.

7. The fatty amide of claim 4 wherein said monoacid d) is 12 hydroxystearic acid in the absence of said monoacid e).

8. The fatty amide of claim 4 wherein said monoacid d) is 12 hydroxystearic acid in the presence of said monoacid e).

9. A process for the preparation of the fatty amide of claim 1 comprising the successive steps of: i) reacting said diamine a) with said lactam or amino acid b), with formation of a diamine a) modified b), ii) reacting product from stage i) with said monoacid d) in the presence or absence of said monoacid e) and in the presence or absence of said diamine c).

10. The process according to claim 9, wherein said component b) is a lactam and wherein said reaction with said amine a) is an anionic oligomerization of said lactam b) using said diamine as anionic initiator.

11. A process for the preparation of the fatty amide of claim 1 comprising the successive steps of: i′) reacting said monoacid d) or optionally of the said monoacid e) if present, with said lactam or amino acid b), to produce corresponding monoacid modified by b), ii′) reacting said modified monoacid from step i′) with said diamine a), in the presence or absence of said diamine c) and if said monoacid from said step i′) is said monoacid d), then in the presence or absence of said monoacid e), otherwise, if said monoacid from said step i′) is the monoacid e), then in the presence of said monoacid d).

12. The process according to claim 11, wherein said monoacid e) is present with said process comprising successive reaction steps: i′) reacting said monoacid e) with said lactam or amino acid b), with formation of a monoacid e) modified b), ii′) reacting said modified monoacid formed at stage i′) with said diamine a) and said monoacid d) and in the presence or in the absence of said diamine c).

13. An organogelator comprising or consisting of at least one fatty amide according to claim 1.

14. The organogelator of claim 13 in preactivated form in an organic solvent.

15. An organic binder composition comprising at least one amide according to claim 1.

16. The fatty amide of claim 1, wherein said hydroxylated fatty C18 or C20 monoacid is chosen from the group consisting of 12 hydroxystearic acid and 14 hydroxyeicosanoic acid.

Description

EXAMPLE 1: DIAMIDE BASED ON AN M-XYLYLENEDIAMINE/CAPROLACTAM PRECONDENSATE AND ON HEXAMETHYLENEDIAMINE

(1) 64.4 g of m-xylylenediamine/caprolactam precondensate (i.e., 0.25 mol or 0.5 equivalent of amine, the 0.25 mol of precondensate corresponding at the start to 0.25 mol of m-XDA which has reacted with 0.25 mol of caprolactam), 63.8 g of hexamethylenediamine (i.e., 0.25 mol, 0.5 equivalent of amine), and 315.2 g of 12-hydroxystearic acid (1.00 mol, 1.00 equivalent carboxy) are introduced, under a nitrogen atmosphere, into a 1 liter round-bottomed flask equipped with a thermometer, a Dean and Stark apparatus, a condenser and a stirrer.

(2) The mixture is heated to 200° C., still under a stream of nitrogen. The water removed begins to accumulate in the Dean and Stark apparatus from 150° C. The reaction is monitored by the acid and amine numbers. When the acid and amine values are less than 10 mg KOH/g, the reaction mixture is cooled to 150° C. and then discharged into a silicone mould. Once cooled to ambient temperature, the product is micronized mechanically by grinding and sieving in order to obtain a fine and controlled size grading with a mean size obtained of 7μ.

(3) IV—Evaluation of the Rheological Performance in a Paint Formulation

(4) Paint Formulations Used for the Evaluation

(5) 1—Preparation

(6) A millbase formulation is prepared with the proportions of Table 3 in the following way:

(7) In a disperser bowl (Dispermill® 2075 yellowline, supplier: Erichsen) heated by a jacket system: 1. Introduction of the epoxy binders and also the dispersant and the defoamer. The homogenization takes place after 2 minutes at 800 revolutions/minute (rpm). 2. Introduction of the fillers and pigments and then grinding at 3000 revolutions/minutes for 30 minutes using a 7 cm blade. By virtue of the jacketed bowl, this stage is cooled with a bath of cold water (20° C.). 3. Introduction of the solvents.
2—Activation

(8) 24 hours after the preparation of the millbase, the formulation is again dispersed at 3000 revolutions/minute (rpm) using a 4 cm blade. Each diamide is introduced into the millbase at a given activation temperature (varying from 40° C. to 70° C.) over 20 minutes at 3000 revolutions/minute.

(9) After the addition of the diluted hardener (Table 4) to the millbase, the paints are adjusted with a xylene/butanol (1/1) mixture to 0.4 Pa.Math.s (measured on the cone 4 at 25° C. at 2500 s.sup.−1 using the Brookfield® CAP 1000). The proportions between the hardener and the mixture of solvents are defined in Table 4.

(10) After the adjustment, the paint is mixed at 1500 revolutions/minute for 2 minutes and then left standing for 30 minutes.

(11) TABLE-US-00002 TABLE 2 Millbase formulation Composition of the millbase Function % by weight Araldite ® GZ 7071X75 binder 17.3 Araldite ® GY 783 BD binder 12.9 Byk ® A530 defoamer 0.5 Disperbyk ® 110 dispersant 0.5 Tiona ® 595 (titanium dioxide) pigment 1.9 Bayferrox ® 915 595 (iron oxide) pigment 4.1 ZP 10 (zinc phosphate) pigment 7.5 Finntalc ® MO5 filler 9.4 Silica HPF6 filler 19.0 n-Butanol solvent 5.4 Diamide Example 1 rheology additive 0.8 TOTAL 79.3

(12) TABLE-US-00003 TABLE 3 Hardener Composition of the hardener % by weight Crayamid ® 140 8.8 Xylene 11.9 TOTAL 20.7
3—Evaluation of the Rheology of the Formulations and Results

(13) A paint formulation was produced following the proportions of Tables 2 and 3 with an activation temperature of 60° C. according to the protocol set out above.

(14) The resistance to running results (Table 4) and the rheology results (Table 5) show that the diamide of Example 1 according to the invention has a thixotropic effect on the formulation once it is activated at 60° C. and a good resistance to running.

(15) TABLE-US-00004 TABLE 4 Resistance to running results Activation Resistance to running temperature Diamides (μ) 60° C. 1 375

(16) TABLE-US-00005 TABLE 5 Rheological results Brookfield viscosity at 25° C. (mPa .Math. s) Activation 1 5 10 50 100 temperature Diamides RPM RPM RPM RPM RPM 60° C. 1 7800 2760 1880 924 736