The method of producing a component for a wax-like, film-forming and adhesive compositions based monoamino dibasic carboxylic acids

 

(57) Abstract:

Use: in organic synthesis, as a component of a wax-like, film-forming and adhesive compositions based monoamino dibasic carboxylic acids other Reagent 1: dibasic acid or anhydride. Reagent 2: hydroxyl-containing compound is a mixture of aliphatic and terpene alcohols unsaponifiable substances extracted after removal of the solvent from the filtrate of the product of the extraction of sulfate soap. 5 table.

The invention relates to organic synthesis, more precisely, to obtain a new mixture of monoamino dibasic carboxylic acids, which can be used as a substitute for rosin in a wax-like, film-forming and adhesive.

Now for the sizing of paper using a variety of rosin: gum, extraction, tall oil, tall oil pitch, modified rosin and synthetic sizing materials are petroleum based [1] On chemical structure rosin is a mixture of unsaturated resin acids (the main component is abietic acid), which has a high susceptibility to oxidation (as a compound with double bonds) and low tempat emitting CO2.

These shortcomings rosin eliminates its chemical modification: the hydrogenation of the double bonds of the resin acids, disproportionation, by the condensation of unsaturated compounds. However, modified rosin products much more expensive.

Synthetic substitutes rosin: stromal (a copolymer of styrene with maleic anhydride), petroleum resin (NTC) type "Pyroplast-2", gluteal (NPS modified with maleic anhydride), despite good sizing the ability to not give a stable aqueous dispersions and require supplements rosin soap (50%) when gluing paper [2]

The purpose of the invention, the receiving component of a sizing composition which is devoid of these shortcomings.

This goal is achieved using known esterification reaction dibasic carboxylic acids or their anhydrides, [3] a mixture of aliphatic and terpene alcohols, which are an integral part of unsaponifiable substances sulfate soap allocated after the distillation of gasoline and alcohol from the filtrate product extraction gasoline sulfate soap, dissolved in alcohol. (Method of refining sulfate soap with the release of phytosterol, a phytosterol) known as the "neutral" (TOOP 13281078-54-89).

Natrol obtained as follows.

Sulphate soap (a by-product of cellulose production by sulfate method of cooking) to obtain a phytosterol dissolved in 30 Mr. aqueous solution of ethanol at a ratio of 1 wt.h. sulfate soap: 0.3 wt.h. 30 ethanol. In the resulting homogeneous mass of sulfate soap add gasoline and spend extraction extraction of unsaponifiable substances (N. C.) from sulfate soap.

The mode of extraction: the ratio of sulphate soap gasoline is 1 of 5 (by mass), temperature 40 45oC, time 1 6 hours After the end of the extraction process to separate the raffinate from the extract. The raffinate contains refined soap PPF product processing phytosterol. Refined soap does not contain virtually N. C. Alcohol and gasoline is distilled from PPF and used in subsequent process cycles. From the extract evaporated gas to the mixture and N. C. and phytosterol add the alcohol from which the crystallization produce phytosterol, and from the filtrate after removal of the alcohol get neutral.

Physico-chemical characteristics of natrol are given in table.1.

The chemical composition of neutral is a multicomponent mixture containing: alcohols (higher fat, diterpene, triterpene, and other oxidized compounds.

The esterification of dibasic carboxylic acids with alcohols of natrol takes place at a temperature of 150 180oC for 1 to 1.5 hours To complete the required subsequent heating of the reaction mixture at 200 210oC for 1 to 2 hours to Heat the mixture of dibasic carboxylic acids and neutral immediately on 200oC is not recommended because of the strong foaming of the reaction mixture in the violent reaction.

Using neutral allows you to expand the resource base, increase product yield, simplify and reduce the cost of the technology (the process takes place without a catalyst and solvent.

It was established that in the proposed method, the ratio of carboxylic acids and mixtures of aliphatic and terpene alcohols unsaponifiable substances sulfate soap, preferably in the range of 2.4 to 1 1 4.

The essence of the invention is illustrated by the following examples.

In the examples used neutral, which previously drove volatile impurities by heating to 140 150owithin 1 h

Example 1. 150 g of neutral and 30 g of maleic acid, the ratio of maleic acid and neutral 1 to 5 were mixed in a three-neck flask with a thermometer, stirrer and descending the refrigerator for 1 hour Then the temperature of the reaction mixture was raised to 200oC and was heated at 200 210oC for 2 h In the receiver collected the emitted water (2.5 ml). Received 171 g of a resinous product. Acid number (K. H.) 112 mg KOH/g, saponification number (including acting) 284 mg KOH/g

IR-spectrum (drop), cm-1: 3200 (-OH); 1735 and 1720 (C O); 3010, 1635, 1440 (-CH=CH-).

Example 2. According to the method described in example 1 of 36 g of maleic acid and 162 g of neutral (1 4,5) obtained a resinous product (190.5 g).

Example 3. According to the method described in example 1, from 46.2 g of maleic acid and 185 g of neutral (1 4) received 220 g of a solid resinous product So pl. 62 102oC, K. H. 120 mg KOH/g, H. O. 290 mg KOH/g

Example 4. According to the method described in example 1, by 44.3 g of maleic acid and 155 g of neutral (1 to 3.5) obtained 189,3 g solid resinous product. So pl. 64 105oC, K. H. 126 mg KOH/g, H. O. 296 mg KOH/g

Example 5. According to the method described in example 1, of 61.6 g of maleic acid and 185 g of neutral received 231,5 g solid resinous product. So pl. 65 105oC, K. H. KOH/g, H. O. 298 mg KOH/g

Example 6. To 243 g natrol heated to 150oC in a flask with a stirrer, thermometer and reflux with vigorous stirring in the course of which the temperature of the reaction mixture was raised to 170oC and heated at 170 180oC 1 h, and then increased the temperature to 200oC and was heated at 200 210oC for 2 hours. Got 279,5 g of a resinous fluid product. K. H. 109 mg KOH/g, H. O. 282 mg KOH/g

Example 7. According to the method described in example 6, 38 g of maleic anhydride and 171 g of neutral (1 4,5) received 201,3 g of a resinous fluid product K. H. 111 mg KOH/g, H. O. 284 mg KOH/g

Example 8. According to the method described in example 6, 184 g of maleic anhydride and 737 g natrol (1 4) obtained 886 g of solid glassy product. So pl. 66 104oC, K. H. 120 mg KOH/g, H. O. 292 mg KOH/g IR-spectrum (in the film), cm-1: 1800, 1750, 1725 (C O), 3005, 1630, 1430 (-CH=CH-), 3220 (-OH).

Example 9. According to the method described in example 6, 50 g of maleic anhydride and 150 g of neutral (1 3) obtained 191,2 g solid glassy product. So pl. 68 105oC, K. H. 128 mg KOH/g, H. O. 298 mg KOH/g

Example 10. According to the method described in example 6, from 64 g of maleic anhydride and 160 g of neutral received 212,8 g of solid product. So pl. 69 - 106oC.

Example 11. 35 g of phthalic acid and 164,5 g natrol (1 4,7) was stirred in a flask with a thermometer, a stirrer and a downward fridge for 0.5 hours at room temperature. The mixture was heated to ri 210 220oC for 2 h In the receiver was going segregated water (2.8 ml). Got 190 g of a resinous fluid product. K. H. 40 mg KOH/g, H. O. 76 mg KOH/g

Example 12. According to the above method of 68 g of phthalic acid and 270,8 g natrol (1 3,1) received 326,7 g solid resinous product. So pl. 68 110oC, K. H. 58 mg KOH/g, H. O. 77,2 mg KOH/g

Example 13. According to the method described in example 11 of 46 g of phthalic acid and of 128.8 g of neutral (1 2,8) received to 166.2 g of solid resinous product. So pl. 68 of 111oC, K. H. 72 mg KOH/g, H. O. 79 mg KOH/g

Example 14. According to the method described in example 11 of 30 g of phthalic acid and 69 g of neutral (1 2,3) received 93,6 g of solid product. So pl. 69 - 113oC, K. H. 76 mg KOH/g, H. O. 78,6 mg KOH/g

Example 15. 72 g of phthalic anhydride gradually under stirring were added to 252 g natrol (1 to 3.5) is heated to 150oC. the Reaction mixture was stirred at 150 160oC for 1 h, then the temperature is gradually raised to 210oWith and was heated at 210 220oC for 2 hours Got a resinous fluid product, 311, K. H. 52 mg KOH/g, H. O. 72 mg KOH/g

Example 16. According to the method described in example 15 from 65K g of phthalic anhydride and 195 g of neutral (1 3) received of 249.6 g of solid product is 1430 (C=C), 3310 (-OH).

Example 17. According to the method described in example 15, 45 g of phthalic anhydride and 122,9 g natrol (1 2,7) received 160,8 g of the solid product, so pl. 69 110oWith, K. H. 70 mg KOH/g, H. O. 74,5 mg KOH/g

Example 18. According to the method described in example 15 of 34 g of phthalic anhydride and 68 g of neutral (1 2) received a 96.9 g of solid product. So pl. 69 112oWith, K. H. 89 mg KOH/g, H. O. 76 mg KOH/g

Example 19. 50 g Monoaluminate obtained by the method described in examples 8 to 10 was heated at 160 170oC with 3.5 g of calcium oxide for 1.5 hours Received 52 g of a solid glassy product. So pl. 55 112oWith, K. H. 80 mg KOH/g

All the examples and characteristics of the products obtained are summarized in tabl.

Thus, the proposed method provides the possibility of obtaining monoamino dibasic carboxylic acids are more technological way, from the available raw materials.

The most interesting are glassy, conforatable products derived from maleic anhydride and neutral according to the method described in examples 8 and 9.

On chemical structure of the products are monetary maleic acid and alcohols (aliphatic and terpene) unsaponifiable vesectomy and connections do not react with carbonyl compounds, and others). The structure of the obtained monoamino confirmed by the data of IR spectroscopy (see examples), the determination of the acid number and saponification number.

Comparative characteristics of rosin and of the product obtained in example 8 are shown in table.3.

The product obtained by the method described in example 8, was tested as a substitute for rosin in the sizing of paper, as a softener in rubber mixtures based on isoprene rubber (SKI) and as a component film-forming composition.

For new esters of dibasic carboxylic acids of the proposed method can be used standard equipment for rosin glue (reactor with stirrer). The process is performed without releasing volatile products, without waste, without the use of conventional esterification catalysts, without the use of solvents, that is environmentally friendly.

The creation of the film-forming process of a new product on the basis of neutral substances sulfate soap will allow companies PPI receiving pulp by the sulphate method to carry out a more deep processing of wood, to expand the product range PR is the procedure, described in example 8, was prepared white rosin size, with a concentration of 20 g/L. According to standard methods made casting sack paper weight 1 m270 g of the sulfate neabelevoi pulp with a beating degree of 22 28 W-R. Glue was injected mass flow rate of 0.5 to 5% of absolutely dry matter (and.with.in.). Properties of the paper obtained by applying white glue from the sample N 8, are given in table. 4.

The tests showed that the new product obtained by the method described in example 8, forms a stable adhesive emulsion which can be used for paper sizing instead of glue on the base of gum rosin. Mechanical strength test samples of paper higher than the paper obtained according to GOST (using gum rosin).

Based on the sample N 8 prepared lacquer composition is presented in table. 5, by a standard method, containing, including

Oil on linen 14

The foaming agent 36

Desiccant 1,2

Xylene 48,8

Lacquer-based sample N 8 gives more light film hardness is not inferior to the standard.

The method of producing a component for a wax-like, film-forming and adhesive compositions based monoamino dibasic carboxylic acids total is containing compound, characterized in that, as the hydroxyl-containing compounds used natrol containing a mixture of aliphatic and terpene alcohols unsaponifiable substances, selected after the distillation of gasoline and alcohol from the filtrate product extraction gasoline sulfate soap, dissolved in alcohol.

 

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