ES2407529B1 - PROCEDURE FOR THE MANUFACTURE OF A YELLOW-ORANGE VARNISH AND PRODUCT OBTAINED. - Google Patents

PROCEDURE FOR THE MANUFACTURE OF A YELLOW-ORANGE VARNISH AND PRODUCT OBTAINED. Download PDF

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Publication number
ES2407529B1
ES2407529B1 ES201101249A ES201101249A ES2407529B1 ES 2407529 B1 ES2407529 B1 ES 2407529B1 ES 201101249 A ES201101249 A ES 201101249A ES 201101249 A ES201101249 A ES 201101249A ES 2407529 B1 ES2407529 B1 ES 2407529B1
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obtaining
yellow
varnish
orange
phase
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ES2407529A1 (en
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Francisco Javier TOLEDO MARANTE
Pere FERRIOL BUÑOLA
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Universidad de las Palmas de Gran Canaria
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Universidad de las Palmas de Gran Canaria
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/10—Polymerisation of cyclic oligomers of formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/02—Condensation polymers of aldehydes or ketones only

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)

Abstract

Procedimiento para la fabricación de un barniz amarillo-naranja y producto obtenido.#La presente invención se refiere a un procedimiento para la fabricación de un barniz amarillo-naranja caracterizado porque comprende las siguientes fases:#(i) Se procede a la agitación de una mezcla consistente en acetaldehído y una solución acuosa de sulfito sódico durante al menos 75 minutos, a 10°C, obteniendo el aldol,#(ii) Se procede a la agitación del aldol obtenido en la fase (i) durante al menos 12 horas, a temperatura ambiente obteniendo el polialdol#(iii) El polialdol obtenido en la fase (ii) se disuelve en éter y se lava, en embudo de decantación, con agua. El extracto orgánico resultante se deseca al menos 30 minutos sobre sulfato sódico anhidro y, posteriormente, se filtra y concentra en rotavapor, obteniéndose un aceite coloreado,#(iv) El aceite coloreado obtenido en la fase (iii) se disuelve en acetona y diluye también con acetona, obteniéndose un barniz amarillo naranja.#El procedimiento propuesto permite obtener un barniz con coloración amarillo-naranja sin necesidad de emplear colorantes.Process for the manufacture of a yellow-orange varnish and product obtained. # The present invention relates to a process for the manufacture of a yellow-orange varnish characterized in that it comprises the following phases: # (i) A stirring is carried out. mixture consisting of acetaldehyde and an aqueous solution of sodium sulphite for at least 75 minutes, at 10 ° C, obtaining the aldol, # (ii) The aldol obtained in phase (i) is stirred for at least 12 hours, at room temperature obtaining the polyaldol # (iii) The polyaldol obtained in phase (ii) is dissolved in ether and washed, in a separatory funnel, with water. The resulting organic extract is dried at least 30 minutes over anhydrous sodium sulfate and subsequently filtered and concentrated on a rotary evaporator, obtaining a colored oil, # (iv) The colored oil obtained in phase (iii) is dissolved in acetone and diluted also with acetone, obtaining an orange-yellow varnish. # The proposed procedure allows to obtain a varnish with yellow-orange coloration without using dyes.

Description

Procedimiento para la fabricación de UD barniz amarlllo-naranja y producto obtenido Objeto de la invención La presente invención se ,refiere a un procedimiento para obtener un barniz con coloración Procedure for the manufacture of UD yellow-orange varnish and product obtained Object of the invention The present invention relates to a process for obtaining a varnish with coloration

amarillo-naranja sin necesidad de emplear colorantes. Antecedentes de la invención yellow-orange without using dyes. Background of the invention

Actualmente los barnices presentes en e1 mercado son derivados de subproductos del petróleo, y los barnices de colores requieren del uso de colorantes. El documento de patente GB 390649 A hace referencia a un procedimiento para fabricar Currently the varnishes present in the market are derived from petroleum by-products, and the colored varnishes require the use of dyes. Patent document GB 390649 A refers to a process for manufacturing

barnices de coJor amarillo empleando materias colorantes. Yellowcoat varnishes using coloring materials.

El procedimiento propuesto pennite obtener un barniz con coloración amarillo-naranja sin necesidad de emplear colorantes. Sumario de la invención La presente invención se refiere a un procedimiento para la fabricación de un barniz The proposed procedure pennite obtain a varnish with yellow-orange coloration without using dyes. Summary of the Invention The present invention relates to a process for the manufacture of a varnish

amarillo-naranja caracterizado porque comprende las siguientes fases: yellow-orange characterized in that it comprises the following phases:

(i) (i)
Se procede a la agitación de una mezcla consistente en acetaldehído y una solución acuosa de sulfito sódico durante al menos 75 minutos, a lOOC, obteniendo el aldol, A mixture consisting of acetaldehyde and an aqueous solution of sodium sulphite is stirred for at least 75 minutes, at 10OC, obtaining the aldol,

(ii) (ii)
Se procede a la agitación del aldol obtenido en la fase (i) durante al menos 12 horas, a temperatura ambiente, obteniendo el polialdol The aldol obtained in phase (i) is stirred for at least 12 hours, at room temperature, obtaining the polyaldol

(iii) El polialdol obtenido en la fase (ii) se disuelve en éter y se lava, en embudo de decantación, con agua, El extracto orgánico resultante se deseca al menos 30 minutos sobre sulfato sódico anhidro y, posterionnente, se filtra y concentra en rotavapor, obteniéndose un aceite coloreado, (iii) The polyaldol obtained in phase (ii) is dissolved in ether and washed, in a separatory funnel, with water. The resulting organic extract is dried for at least 30 minutes on anhydrous sodium sulfate and, subsequently, filtered and concentrated. in rotary evaporator, obtaining a colored oil,

(iv) El aceite coloreado obtenido en la fase (iii) se disuelve en acetona y diluye también con acetona, obteniéndose un barniz amarillo naranja, Siendo las proporciones las siguientes: Acetaldehído entre un 19% y un 20% (iv) The colored oil obtained in phase (iii) is dissolved in acetone and also diluted with acetone, obtaining an orange-yellow varnish, the proportions being the following: Acetaldehyde between 19% and 20%

Sulfito sódico en disolución acuosa entre un 0,8% y un 1,0% Éter dietílico entre un 50% y un 60% Sodium sulphite in aqueous solution between 0.8% and 1.0% Diethyl ether between 50% and 60%

Sulfato sódico anhidro entre un 15% y un 20010 Acetona entre un 9010 y un 10% Es también característico de la invención el componente principal obtenido de acuerdo con eJ procedimiento antes mencionado, el polialdol, cuya fónnula molecular es: Anhydrous sodium sulfate between 15% and 20010 Acetone between 9010 and 10% It is also characteristic of the invention the main component obtained according to the aforementioned procedure, polyaldol, whose molecular formula is:

OH OH

CH,-CH CH, -CH

CH=CH CH = CH

CHOH CHOH

CHOH CHOH

CH3 CH3

CH3 CH3

n n

OH OH

,O,OR

CH-C'CH-C '

C-CH C-CH

1 'H1 HOUR

CH CH

CHOH CHOH

CH3 CH3

CH3 CH3

m m

Así mismo, es caracteristico de la invención el que el producto obtenido está fonnado por Likewise, it is characteristic of the invention that the product obtained is funded by

los siguientes componentes: The following components:

Polialdol entre un 20% y un 40% Polyaldol between 20% and 40%

Acetona entre un 60% y un 80% Acetone between 60% and 80%

10 Descripción de las figuras 10 Description of the figures

La figura 1 muestra el espectro de IH_NMR del polialdol. Figure 1 shows the IH_NMR spectrum of polyaldol.

Descripción detallada de una realización preferida de la invención Detailed description of a preferred embodiment of the invention

Aunque la invención se describe en términos de una realización específica preferida, será fácilmente evidente para los expertos en esta técnica que se pueden hacer diversas 15 modificaciones, redisposiciones y reemplazos. El alcance de la invención está definido por las reivindicaciones adjuntas a la misma. Although the invention is described in terms of a specific preferred embodiment, it will be readily apparent to those skilled in this art that various modifications, redispositions and replacements can be made. The scope of the invention is defined by the claims appended thereto.

El procedimiento de obtención de barniz comprende la etapa previa de transformación de bio-etanol en polialdol, cuya disolución acetónica actúa como barniz. Para ello se fabrica bio-etanol, mediante cualquier procedimiento ya conocido (p.ej. el recogido en Shanna N. The process for obtaining varnish comprises the previous stage of transformation of bio-ethanol into polyaldol, whose acetonic solution acts as a varnish. For this, bio-ethanol is manufactured, by any known procedure (eg the one collected in Shanna N.

20 et al, 2007), éste se transforma en acetaldehído por oxidación con Cr (VI), mediante cualquier procedimiento ya conocido (p.ej. el recogido en Rinehart K.L., Jr., 1973) y éste se transforma en barniz mediante el procedimiento reivindicado. 20 et al, 2007), this is transformed into acetaldehyde by oxidation with Cr (VI), by any known procedure (eg, the one collected in Rinehart KL, Jr., 1973) and this is transformed into varnish by the procedure claimed.

El procedimiento de obtención de barniz amarillo-naranja a partir de aceta1dehído es el siguiente: The procedure for obtaining yellow-orange varnish from acetadehyde is as follows:

Se enfría, hasta los SOC, 143,46 mi de acetaldehído y posterionnente se añaden 33,3 mi de una disolución acuosa de sulfito sódico al 15% w/w, con buena agitación y durante 75 minutos, manteniendo la temperatura por debajo de 10 OC. Cool down, to SOC, 143.46 ml of acetaldehyde and subsequently add 33.3 ml of a 15% aqueous solution of sodium sulphite w / w, with good stirring and for 75 minutes, keeping the temperature below 10 OC.

El aldol resultante se mantiene 12 h aproximadamente a temperatura ambiente con 5 agitación magnética, condiciones en que se polimeriza. The resulting aldol is maintained for approximately 12 h at room temperature with magnetic stirring, conditions under which it is polymerized.

El polímero amarillo-naranja resultante (polialdol) se disuelve en éter dietílico (450 mi) y se lava con agua en un embudo de decantación de un litro. El extracto orgánico se deseca 30 minutos sobre sulfato sódico anhidro, y, posterionnente, se filtra y concentra en rotavapor. The resulting yellow-orange polymer (polyaldol) is dissolved in diethyl ether (450 ml) and washed with water in a one-liter funnel. The organic extract is dried 30 minutes on anhydrous sodium sulfate, and then filtered and concentrated on a rotary evaporator.

10 El aceite coloreado resultante (31,62 g) se disuelve en acetona y diluye hasta 100 mi para obtener un barnÍz a131,62 % w/v, cuya fórmula molecular es: The resulting colored oil (31.62 g) is dissolved in acetone and diluted up to 100 ml to obtain a varnish a131.62% w / v, whose molecular formula is:

OH I ?H2-CH OH I? H2-CH

CH= CH l CH = CH l

CHOH CHOH

CHOH I CHOH I

I I

CH, CH, CH, CH,

OH I OH I

C-CH C-CH

11 CH I 11 CH I

CH, CH,

n n

/.0 /.0

CH-C' CH-C '

l 'H l 'H

CHOH CHOH

I I

CH, m CH, m

Claims (2)

REIVINDICACIONES 1.-Procedimiento para la fabricación de un barniz amariUo-naranja caracterizado porque comprende las siguientes fases: 1.-Procedure for the manufacture of a yellow-orange varnish characterized in that it comprises the following phases: 5 (i) Se procede a la agitación de una mezcla consistente en acetaldehído y una solución acuosa de sulfito sódico durante al menos 75 minutos, a 1O"C, obteniendo el aldol, 5 (i) A mixture consisting of acetaldehyde and an aqueous solution of sodium sulphite is stirred for at least 75 minutes, at 1 ° C, obtaining the aldol, (ii) Se procede a la agitación del aldol obtenido en la fase (i) durante al menos 12 horas, a temperatura ambiente, obteniendo el polialdol (ii) The aldol obtained in phase (i) is stirred for at least 12 hours, at room temperature, obtaining the polyaldol (iii) El polialdol obtenido en la fase (ii) se disuelve en éter y se lava, en embudo de (iii) The polyaldol obtained in phase (ii) is dissolved in ether and washed, in a funnel of 10 decantación, con agua. El extracto orgánico resultante se deseca al menos 30 minutos sobre sulfato sódico anhidro y, posterionnente, se filtra y concentra en rotavapor, obteniéndose un aceite coloreado, 10 decantation, with water. The resulting organic extract is dried at least 30 minutes on anhydrous sodium sulfate and then filtered and concentrated on a rotary evaporator, obtaining a colored oil, (iv) El aceite coloreado obtenido en la fase (jii) se disuelve en acetoDa y diluye también con acetona, obteniéndose un barniz amarillo naranja, 15 Siendo las proporciones las siguientes: Aceta1dehído entre un 19% y un 20% Sulfito sódico en disolución acuosa entre un 0,8% y un 1,0% Éter dietílico entre un 50% y un 60% Sulfato sódico anhidro entre un 15% y un 20% (iv) The colored oil obtained in phase (jii) is dissolved in acetoDa and also diluted with acetone, obtaining an orange-yellow varnish, the proportions being the following: Aceta1dehyde between 19% and 20% Sodium sulphite in aqueous solution between 0.8% and 1.0% Diethyl ether between 50% and 60% Anhydrous sodium sulfate between 15% and 20% 20 Acetona entre un 9% y un 10% 2.-Producto obtenido de acuerdo con el procedimiento antes mencionado caracterizado porque el componente principal es el poliadol de fórmula molecular: 20 Acetone between 9% and 10% 2.-Product obtained according to the aforementioned procedure characterized in that the main component is the polyadol of molecular formula: OH OH I CH,-CH I CH, -CH CH=CH I CH = CH I I I CHOH CHOH CHOH I CHOH I I CH3 I CH3 eH3 eH3 n n OH OH /.0/.0 I I CH-C'CH-C ' C-CH C-CH I 'HI 'H CH CH CHOH CHOH I I I I CH3 CH3 CH3 CH3 m m 3.-Producto obtenido según reivindicación 2, que está fonnado por los siguientes componentes: 3. Product obtained according to claim 2, which is linked by the following components: Polialdol entre un 20% y un 40% Polyaldol between 20% and 40% Acetona entre un 60% y un 80% Acetone between 60% and 80%
ES201101249A 2011-11-16 2011-11-16 PROCEDURE FOR THE MANUFACTURE OF A YELLOW-ORANGE VARNISH AND PRODUCT OBTAINED. Active ES2407529B1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE498706A (en) * 1949-10-14
JPS4942677B2 (en) * 1972-05-19 1974-11-16
GB1524775A (en) * 1977-05-05 1978-09-13 Kagna S S And others method of preparing a higher branched saturated carboxylic acid
DE4322112A1 (en) * 1993-07-02 1995-01-12 Sueddeutsche Kalkstickstoff Graft polymers of ketone-aldehyde condensation or co-condensation products

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