Use of alkoxylated amines to improve water-repellent properties

FIELD: chemistry.

SUBSTANCE: invention relates to use of alkoxylated amines to treat wood in order to improve water-repellent properties of wood or reduce the amount of water absorbed by wood. Treatment is carried out with alkoxylated amines of formula where R1 denotes C8-20-alkyl; R2 denotes -[CH2CH(X)O]bH (a-1) or n is an integer from 1 to 4; each of a, b and c independently denotes an integer ranging from 1 to 20; each X is independently selected from a group comprising hydrogen, methyl, ethyl and phenyl. Alkoxylated amines of formula (I), particularly N,N',N' -tris(2-hydroxyethyl)-N-cocoalkyl-1,3-diaminopropane or N,N',N'-tris(2-hydroxyethyl)-N-tall alkyl-1,3-diaminopropane can be used in the composition for treating wood in amount of 0.1-90 wt %.

EFFECT: use of alkoxylated amines of formula (I) to treat wood improves water-repellent properties of wood and reduces the amount of water absorbed by wood.

10 cl, 2 tbl

 

The present invention relates to the use of alkoxysilane amines for wood and other cellulosic materials to enhance their water-repellent properties and reduce the absorption of water by contact of treated wood or other cellulosic materials with water.

Immediately after the cutting of the trees, the wood starts to rot as a result of defeat mushrooms. One of the most successful ways to protect the wood from rotting is the impregnation of wood by processing under pressure with the use of antiseptics for wood, water-based. Such processing can be carried out more effectively by introducing in the process of processing additives that will improve the stability of the treated wood to deformation by giving a high degree of water-repellent ability.

Purpose of processing wood water repellent is to reduce the wettability of the surface of the wood, so that liquid water is not formed adhesive layer and to reduce absorption of liquid water. This prevent absorption of liquid water provides a certain degree of resistance to deformation and prevents the rapid swelling and shrinkage of wood during wetting and drying, and also effectively reduces the degree of mechanical destruction, the formation of t is Emin on the surface and cracking treated wood during the initial drying or during operation. The natural affinity of wood to reduce water by treating the water-repellent, thus minimizing the splitting of the wood, cracking ends and the rise of the fibers, which increases the service life of wood and the quality of its final processing.

You can get water repellent wood by treatment with solutions of resins, coating compounds, latex, or paraffin or hydrocarbon emulsions emulsions containing surfactants.

Alkoxysilane amines of General formula (I), also known as atomine and ethoduomeen are cationogenic surfactants used for many applications such as the production of viscose, food additives the use of additives in agriculture, cleaning, flotation reagents in the mining industry, emulsifiers and amplifiers adhesion to bitumen and agents against caking of fertilizers. In WO-96/10332, WO-03/065807 and EP-1273233 described such alkoxysilane amines to enhance the antifungal activity of copper cations, triazoles and oxadiazine, respectively.

Presently discovered that alkoxysilane amines of the formula (I) can be used as water-repellent means for impregnation of wood and improve its water-repellent abilities which reduce the absorption of water by contact of treated wood with water.

Alkoxysilane amines of the formula (I) have the following General formula

where R1means C8-20-alkyl;

R2means

- (CH2CH(X)O]bH(a-1)

or

n is an integer from 1 to 4;

each of a, b, and c independently denotes an integer that can range from 1 to 20;

each X is independently selected from the group consisting of hydrogen, methyl, ethyl and phenyl.

To the group of interest are compounds of formula (I) include compounds of formula (I), in which each of a, b and c independently denotes an integer that can range from 1 to 6.

The first specific group alkoxysilane amines of the formula (I) are the compounds of formula (I)in which R2means a radical (a-1).

The second specific group alkoxysilane amines of the formula (I) are the compounds of formula (I)in which R2means a radical (a-2).

More specific alkoxycarbonyl amines of the formula (I) are alkoxysilane amines of the formula (I), which applies one or more of the following constraints:

a) n is an integer 2 or 3, preferably n is 3;

b) X is hydrogen;

c) R is C10-20-Ala is l, preferably coconut alkyl or tall alkyl.

Commercially available alkoxysilane amines of the formula (I)in which R2means a radical (a-1), shown in the following table:

Ethoxylated(5)tall alkylamine
Product nameChemical name
Atomin C/12Bis(2-hydroxyethyl)cocoalkylamine
Atomin C/15Ethoxylated(5)cocoalkylamine
Atomin C/25Ethoxylated(15)cocoalkylamine
Atomin O/12Bis(2-hydroxyethyl)oleylamine
Atomin O/17Ethoxylated(7)oleylamine
Atomin O/20Ethoxylated(10)oleylamine
Atomin S/15Ethoxylated(5)soy alkylamine
Atomin S/25Ethoxylated(15)soy alkylamine
Atomin T/12Bis(2-hydroxyethyl)tall alkylamine
Atomin T/15
Atomin T/25Ethoxylated(15)tall alkylamine
Atomin HT/12Bis(2-hydroxyethyl)hydrogenated tall alkylamine
Atomin HT/14ethoxylated(4) hydrogenated tall alkylamine
Atomin HT/17ethoxylated(7) hydrogenated tall alkylamine
Atomin HT/20ethoxylated(10) hydrogenated tall alkylamine
Atomin HT/25ethoxylated(15) hydrogenated tall alkylamine
Atomin HT/30ethoxylated(20) hydrogenated tall alkylamine
Atomin 12/12Bis(2-hydroxyethyl)dodecylamine
Atomin 18/12Bis(2-hydroxyethyl)octadecylamine

Commercially available alkoxysilane amines of the formula (I)in which R2means a radical (a-2), shown in the following table:

Product nameChemical name
Propodosomal C13N,N',N'-Tris(2-hydroxypropyl)-N-cocoalkyl-1,3-diaminopropan
Ethoduomeen T11mono(2-hydroxyethyl)-N-tallow alkyl-1,3-diaminopropan
Ethoduomeen T13N,N',N'-Tris(2-hydroxyethyl)-N-tallow alkyl-1,3-diaminopropan
Ethoduomeen T25N,N',N'-polyoxyethylene(15)-N-tallow alkyl-1,3-diaminopropan
Ethoduomeen C13N,N',N'-Tris(2-hydroxyethyl)-N-cocoalkyl-1,3-diaminopropan

The most preferred alkoxycarbonyl amines of the formula (I) are N,N',N'-Tris(2-hydroxyethyl)-N-cocoalkyl-1,3-diaminopropan (= ethoduomeen T13) and N,N',N'-Tris(2-hydroxyethyl)-N-cocoalkyl-1,3-diaminopropan (= ethoduomeen C13).

Used in this sense, the terms "wood", "wood materials" and "wood products" means all forms of wood such as solid wood (such as lumber or timber in the form of logs, bars, strips, sheets and boards, composite wood materials (such as wood-fiber plate, drives the particle Board and plywood) and all products made of wood and composite wood materials (such as log frames, decking boards, siding, exterior wall cladding, roofing tiles, poles and railway sleepers).

The following aspect of the invention alkoxysilane amines of the formula (I) can be used to improve water-repellent properties of various cellulosic materials such as paper and cardboard.

Alkoxysilane amines of the formula (I) used in the form of a liquid solution for treatment of wood to improve water repellency of wood or decrease the absorption of water by contact of treated wood with water. However alkoxysilane amines of the formula (I) can also be applied to wood undiluted.

Alkoxysilane amines of the formula (I) can be used in the form of a liquid composition, which may be a composition ready to use or concentrated formula that can be diluted immediately before use. Such liquid formulations contain alkoxysilane amines of the formula (I) in an amount of from 0.1 to 90 wt.%.

Suitable carriers for liquid formulations containing water-repellent alkoxysilane amines of the formula (I)represent any fluid that does not adversely impact on alkoxysilane amines of the formula (I), e.g. the p water alcohols (e.g. methyl alcohol, ethyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, glycerin, etc.), ketones (e.g. acetone, methyl ethyl ketone, and so on), ethers (e.g. dioxane, tetrahydrofuran, cellosolve, dimethyl ether of diethylene glycol, etc.), aliphatic hydrocarbons (e.g. hexane, kerosene and so on), aromatic hydrocarbons (e.g. benzene, toluene, xylene, naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (e.g. chloroform, carbon tetrachloride and so on), acid amides (for example, dimethylformamide, etc.), esters (e.g. methyl acetate, ethyl acetate, butyl acetate, esters of glycerol and fatty acids etc) and NITRILES (e.g. acetonitrile etc). These solvents can be used either individually or in combination of two or more kinds.

A carrier for liquid formulations can also be supercritical CO2.

Alkoxysilane amines of the formula (I) can also be used as water-repellent additives in compositions for treatment of wood that is used primarily for production of wood more resistant to infection with bacteria, fungi, mold or insects.

Liquid compositions containing alkoxysilane amines of the formula (I), can be applied to the wood in any way, e.g. the methods of treatment by immersion, spraying, electrostatic spraying, curtain coating, coating with a brush, coating, immersing, coating, spraying, coating with a roller and treatment in vacuum/pressure using a differential pressure for penetration of liquid.

Experimental part

Materials and methods

Wood

Alkoxysilane amines: ethoduomeen C/13 (Akzo Nobel), CAS 90367-21-8, ethoduomeen T/13 (Akzo Nobel), CAS 90367-27-4.

The tested concentration: 500, 2500 and 12500 mg/liter (ppm) in demineralised water, but ethoduomeen T/13 at a concentration of 12500 ppm was dissolved in 0.2% to 0.1 N HCl (= 2,10-4M or 7.3 ppm).

Solvent: sterile demineralized water.

The type of wood: Scots pine (Pinus sylvestris); 556,58 kg/m3.

The dimensions of wood: 15 × 25 × 50 mm (volume of 18.75 cm3average laboratory dry weight (n = 110) of 10.50 g with a standard deviation 0,72).

Processing: impregnation under pressure: 400 mbar for 10 minutes; coating the surface: immersion for 30 seconds.

Control: treatment of demineralized water or treatment of demineralized water with addition of 0.2% to 0.1 N HCl (= 2,10-4M or 7.3 ppm) (only in case of ethoduomeen T/13 the test solution 12500 ppm).

Replays: 5

Fixation: 14 days

Drying: 14 days + 3 days

Testing water-repellent properties

Method of evaluation: the weight increase % after immersion in demineralized water for 30 minutes at room temperature;

% swelling in the tangential direction, which is measured along the sides of the blocks with a length of 25 mm after immersion in demineralized water for 30 minutes at room temperature (by awpa standard E4-78).

Statistics:Treatments were compared with controls using ANOVA with the amendment of the Dunnet multiple comparisons. In General, p = 0.05, the critical t-value = 2,72 (g = 6, df = 32), resulting in α = 0,0105.

Result and discussion

Table 1:
The weight increase % after a 30-minute immersion of the wood processed by ethoduomeen C/13 and T/13.
ControlsEthoduomeen T/13 (h/m)Ethoduomeen/13 (h/m)
WaterHCl5002500125005002500 12500
The vacuum44,15of 44.6743,2822,4021,6133,1723,2327,97
46,4243,6042,0620,48of 17.3531,8038,6924,79
49,8546,9939,2025,5617,5231,2923,1321,22
46,2737,9341,5932,7424,1335,7732,8137,78
47,5746,6938,5625,9718,93 44,7927,6722,00
Average*46,8543,9840,9425,43*of 19.91*35,37*29,10*26,75*

ControlsEthoduomeen T/13 (h/m)Ethoduomeen/13 (h/m)
WaterHCl500250012500500250012500
Dive31,0737,2335,5332,1817,8633,1125,6117,71
33,8325,3228,76 23,4122,8628,6822,04
28,9039,1537,7534,4424,4532,6931,76to 22.83
43,1820,6837,1626,0524,4632,2127,0326,99
31,4227,5930,0539,8322,1235,1617,75results were 23.08
Average*33,6829.99 is33,8532,8122,46*31,2126,1722,53*
The average listed *, significantly different(P = 0.05) from the control.

After vacuum impregnation, the average increase in weight in % due to water absorption of the treated units is significantly lower than in controls (5%) in case of all tested concentrations ethoduomeen C/13, and for 2500 and 12500 ppm ethoduomeen T/13.

After immersion, the average increase in weight in % due to water absorption of the treated units is significantly lower than in controls (5%) in the case 12500 ppm ethoduomeen C/13 and T/13.

Table 2:
Swelling in the tangential direction in % after a 30-minute immersion of the wood processed by ethoduomeen C/13 and T/13.
ControlsEthoduomeen T/13 (h/m)Ethoduomeen/13 (h/m)
WaterHCl500250012500500250012500
The vacuum3,763,163,290,841,80 2,500,922,92
4,083,553,052,001,212,723,721,43
3,632,833,812,531,521,391,932,22
4,763,483,68of 2.511,401,982,563,12
4,803,442,901,361,563,301,280,48
Average*4,213,293,35*1,85* 1,50*2,38*2,08*2,03*
ControlsEthoduomeen T/13 (h/m)Ethoduomeen/13 (h/m)
WaterHCl500250012500500250012500
Dive2,641,972,082,020,801,451,201,58
of 2.211,402,401,521,170,561,411,21
1,811,811,932,380,97 2,101,521,20
3,660,891,930,680,791,401,681,46
1,801,451,412,460,881,961,080,84
Average*2,421,501,951,810,92*1,491,381,26*
The average listed *, significantly different (P = 0.05) from the control.

After vacuum impregnation, the average swelling in the tangential direction in % as a result of water absorption of the treated units is significantly lower than in controls (5%) in case of all tested concentrations ethoduomeen C/13 and T/13.

After immersing the average swelling in the tangential direction in % in achiev is Tate water absorption of the treated blocks significantly lower than in controls (5%) in the case 12500 ppm ethoduomeen C/13 and T/13.

Conclusion

Vacuum impregnation of pine alkoxycarbonyl amines by ethoduomeen C/13 and T/13 significantly reduces the water absorption of treated wood even at relatively low concentrations of amines.

Short immersion of the wood in the solution ethoduomeen gives a significant reduction in water absorption only when using high concentrations ethoduomeen C/13 or T/13.

1. Application alkoxysilane amines of the formula

where R1means C8-20-alkyl;
R2means

or

n is an integer from 1 to 4; each of a, b and C independently denotes an integer that can range from 1 to 20; each X is independently selected from the group consisting of hydrogen, methyl, ethyl and phenyl; to improve water-repellent properties of wood or decrease the amount absorbed by the wood is water.

2. The use according to claim 1, in which R2means a radical of the formula (a-1).

3. The use according to claim 1, in which R2means a radical of the formula (a-2).

4. The use according to claim 1, in which alkoxycarbonyl an amine of the formula (I) is N,N',N'-Tris(2-hydroxyethyl)-N-cocoalkyl-1,3-diaminopropan.

5. The use according to claim 1, in which alkoxycarbonyl and the other of formula (I) is N,N',N'-Tris(2-hydroxyethyl)-N-tallow alkyl-1,3-diaminopropane.

6. The use according to any one of claims 1 to 5, in which the wood is treated with a composition containing alkoxysilane amines of the formula (I) according to claim 1.

7. The use according to claim 6, in which processing is a vacuum or processing of wood under the pressure of a liquid composition containing alkoxysilane amines of the formula (I) according to claim 1.

8. The use according to claim 7, in which the wood treatment includes immersion, spraying, electrostatic spraying, curtain coating, coating with a brush, coating by dipping, coating, spraying or coating with a roller, using a liquid composition containing alkoxysilane amines of the formula (I) according to claim 1.

9. The use according to claim 7, in which alkoxysilane amines of the formula (I) are present in the liquid composition in an amount from 0.1 to 90 wt.%.

10. The use of claim 8, in which alkoxysilane amines of the formula (I) are present in the liquid composition in an amount from 0.1 to 90 wt.%.



 

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