PL152460B2 - An agent for colouring polyester products into brown colour - Google Patents

Description

PATENT DESCRIPTION

PATENT OFFICE OF THE RP

Additional patent to patent no. ----- Pending: ⁸ 7 12 30 (P. 269927)

Priority ---- Application announced: ^{08 10 13}

Patent description published: 1991 08 30

Int. Cl. ⁵ C09B 67/38

Creators of the invention: Jerzy Jabłoński, Mirosław Muszyński, Halinaścibisz

Authorized by the patent: Research and Development Center

ORGANIKA Dye Industry,

Zgierz (Poland)

BROWN COLORING POLYESTER PRODUCTS

The subject of the invention is a dyeing agent intended for brown dyeing of polyester fiber products in the quick dyeing method.

Dyeing of polyester fiber products using the pressure method is carried out at a temperature of 120-130 ° C under a pressure of 1.5-2.5 MPa for 1-1.5 hours, the bath heating rate being a maximum of 2 ° C per minute as a dyes are disperse dyes. This method has a number of technological disadvantages, especially: long dyeing time and high energy consumption. Currently, the traditional pressure method is being replaced by the quick dyeing method, which consists in dyeing polyester fiber products at a temperature of 130-140 ° C under a pressure of 3-4 MPa, for 5-20 minutes, while the bath reheating time is 2-10 ° C for a minute.

Disperse dyes used to dye polyester fibers in the traditional pressure method are not used in the quick dyeing method, because under the temperature conditions and the short duration of the dyeing process, they agglomerate, aggregate or melt, which significantly reduces the durability of their aqueous dispersion, dye particles are deposited on the surface fibers causing uneven dyeing, poor exhaustion from the bath, low color efficiency and low color fastness in use.

As a result of the research, it was unexpectedly found that a coloring agent containing properly selected quantitatively and qualitatively in terms of chemical structure and stable crystallographic form compounds of formula 1, where X represents a hydrogen or chlorine atom or a methyl or ethyl, methoxy or ethoxy, phenylazic, carboxyester COOR5, where R5 is alkyl with 1-4 carbon atoms, Y is hydrogen or chlorine, or nitro or cyano, Z is alkyl with 1-4 carbon atoms or the group (CH1hCOORj,

152 460

152 460 wherein R ₂ represents alkyl of 1-4 carbon atoms, n = 1-5 or a group _{(CH2) n} 0Ri, wherein R is methyl or ethyl, n = 1-4, of formula 2, wherein R is methyl or ethyl, R ₂ represents a hydrogen atom or a methyl group, of formula 3, wherein X represents a hydrogen or chlorine atom or a group: hydroxy or cyano, Y is hydrogen or nitro, R is hydrogen or C methyl, R stands for hydrogen atom, stands for: ethyl, β-cyanoethyl, benzyl, β-acetoxyethyl, β-hydroxyethyl or allyl groups, V ₂ stands for: β-cyanoethyl, benzyl, β-acetoxyethyl, -hydroxyethyl or allyl groups, stands for hydrogen atom or acylamino NHCORj, wherein R is alkyl of 1-2 carbon atoms, or of formula 3 wherein X is chlorine or bromine, Y is nitro, R is hydrogen, R ₂ is methoxy or ethoxy, o.znacza acylamino group NHCORj, where Rj is alkyl with 1-2 carbon atoms, is β-cyanoethyl, β-acetoxyethyl, benzyl or allyl group, V ₂ is β-acetoxyethyl, benzyl or allyl group, and where X is the group amino or hydroxy, Y represents a hydrogen atom or groups: phenylhydroxy or phenylmethoxy, Z represents an amino or aminophenyl group, V represents a hydrogen atom or a hydroxyl group, R represents a hydrogen atom or an amino group, and the formula 5, wherein X, Y, Z, V oz They contain hydroxyl and amine groups, when used to dye polyester fiber products in the quick dyeing process, it allows to obtain a brown color with high color efficiency, and the dyes are characterized by even coloring and high durability in use.

The essence of the invention consists in preparing a coloring agent with the following composition: 0-65 parts by weight of compounds with a stable crystallographic form of formula 1, in which X represents a hydrogen or chlorine atom, or groups: methyl or ethyl, methoxy or ethoxy, phenylazic, carboxyester COORp in which R ^ is an alkyl having 1-4 carbon atoms, Y is hydrogen or chlorine or nitro or cyano group, Z is alkyl having 1-4 carbon atoms or a (CH _{2) n} C00R _2, wherein R ₂ is alkyl of 1 4 carbon atoms, n = 1-5 or the group (CH 2 JPOR 2, in which R 2 is a methyl or ethyl radical, n = 1-4, 0-70 parts by weight of stable crystallographic compounds of formula 2, in which R R 2 represents a methyl or ethyl group, R ₂ represents a hydrogen atom or a methyl group, 10-30 parts by weight of stable crystallographic compounds of the formula 3 in which X represents a hydrogen atom or a chlorine atom, or a hydroxyl or cyano group, Y represents a hydrogen atom or nitro, R5 is hydrogen or a methyl group, R ₂ represents a hydrogen atom, V ₁ represents the group: ethyl, β -cyjanoetylową, benzyl, -acetoksyetylową β, β-hydroxyethyl or allyl, V? means: β-cyanoethyl, benzyl, β -acetoxyethyl, -hydroxyethyl or allyl groups, means hydrogen atom or acylamino group NHCORj, in which Rj is alkyl with 1-2 carbon atoms, 0-40 parts by weight of compounds with stable crystallographic form of formula 3, where X is chlorine or bromine, Y is nitro, Rj is hydrogen, R ₂ is methoxy or ethoxy, Vj is acylamino NHCOR-j group in which Rj is alkyl

1-2 carbon atoms, is a β-cyanoethyl, β-acetoxyethyl, benzyl or allyl group, V ₂ is a β-acetoxyethyl, benzyl or allyl group, 0-20 parts by weight of stable crystallographic compounds of formula 4, in which X is an amino or hydroxyl group, Y is a hydrogen atom or groups: phenylhydroxy or phenylmethoxy, Z is an amino or aminophenyl group, V is a hydrogen atom or a hydroxyl group, R is a hydrogen atom or an amino group, 0-20 parts by weight of compounds with stable crystallographic form Formula 5, wherein X, Y, Z, V are hydroxyl and amino groups. The composition comprises at least two compounds of the formulas 1, 2, 3, 4, 5 shown above, one of which is a compound of formula I or 2. In addition, the agent contains known dispersing, wetting and anti-dusting compounds.

The dyeing agent prepared according to the invention, used for dyeing polyester fiber products in the quick dyeing method, dyes brown in a uniform manner with high color efficiency, the obtained dyes do not require reducing and cleaning treatment and have high utility values of resistance to: friction 5 “, 5 ', heat treatment 4-5', 3-4 °, dry cleaning 5 ', 5 °, wet 4-5', 4 ', light 6-7'. The unexpected effect of obtaining very good dyeing with the agent according to the invention is not due to the properties of the components of the coloring agent, because these components being compounds of the formulas 1, 2, 3, 4, 5, the substituents of which have been discussed above, are suspension dyes, which are used individually for dyeing articles or polyester fibers in quick dyeing methods at the temperature of 130-140 ° C agglomerate, partially melt, which significantly reduces the durability of their aqueous dispersion, dye particles settle on the surface of the fibers, causing uneven dyeing, poor depletion from the bath, low color efficiency and low utility resistance colorings.

In the following illustrative examples of the invention, parts and percentages are parts and percentages by weight and degrees of temperatures are given in degrees Celsius.

Example I. 1000 parts of a standardized micropowder containing 25¾ stable crystallographic form of the compound of formula 1, in which X is a nitro group, Y is a chlorine atom, Z is a group (CH ^ j ^ COOCHj, 400 parts of a standardized micropowder containing 55¾ stable crystallographic form compound of formula 3, in which X is cyano, Y, Rj, R ', Vj is hydrogen, Vj is ethyl, V' is -cyanoethyl, 300 parts of standardized 22 mik micropowder containing stable crystallographic form of compound of formula 4 where X is an amino group, Y, V, R are hydrogen, Z is an aminophenyl group, 300 parts of a standardized 24¾ micropowder containing stable crystallographic form of a compound of formula 5, in which X, V are hydroxyl, Z, Y are the amino group is homogenized by stirring in a Naut apparatus for 3-4 hours.

The obtained dyeing agent permanently dyes polyester products and fibers at the temperature of 130-140 ° C for 5-15 minutes in circulating bath apparatuses, at the bath flow rate of 80-150 dm / min / kg, to an intense brown color with a blue shade. The obtained dyes after rinsing in water and light washing without reducing-cleansing treatment are characterized by high uniformity and vivacity, very good resistance to: light 6 ', friction 5', 5 ', wet factors 5', 4-5 °, dry cleaning 5 ', 5' and for heat treatment 4-5 ', 4'.

Example II. 1500 parts of a standardized micropowder containing 25¾ stable crystallographic form of the compound of formula 1, where X, Y are hydrogen, Z is the group (CH ^ j ^ COOC ^ H ^, 600 parts of standardized micropowder containing 55 stable crystallographic form of the compound of formula 3, where X is cyano, Y, Rj, R ', Vj is hydrogen, is β-cyanoethyl, Vj is ethyl, 450 parts of standardized micropowder containing 40¾ stable crystallographic form of compound of formula 3, in which X represents a chlorine atom, Y represents a nitro group, Rj represents a hydrogen atom, R 2 represents a methoxy group, represents a β-cyanoethyl group, V 'represents an allyl group and 230 parts of a standardized micropowder containing 54¾ stable crystallographic form of the compound of formula 3, in which X stands for chlorine atom, Y stands for nitro group, R4 stands for hydrogen atom, R 'stands for ethoxy group, Vp stands for β-acetoxyethyl group, stands for ace tyloamine is homogenized in the Naut apparatus for 4-6 hours.

The obtained dyeing agent permanently dyes polyester products at the temperature of 130-140 ° C in the rapid dyeing machines with the circulation of the bath for 5-15 minutes to an intense brown color with a blue-red shade. Dyeing after rinsing in water and light washing without reducing-cleansing treatment are characterized by high uniformity and high durability in use: light 6 ', friction 5 °, 5', wet agents 5 *, 4-5 ', dry cleaning 5 °, 5 ° , heat treatment 4-5 ', 4'.

152 460

Example III. 1000 parts of a pre-standardized containing fluid

25¾ permanent as the crystal of the compound of formula 2 wherein R is methyl, R is hydrogen, 400 parts of pre-standardized containing liquid 27¾ permanent as crystal compound of formula 3 wherein X is cyano, Y, Rp _R2 hydrogen atom, represents an ethyl group, V ₂ represents a β-cyanoethyl group, 300 parts of a pre-standardized fluid containing 20¾ stable crystallographic form of a compound of formula 3, in which X is bromine, Y is a nitro group, R4 is a hydrogen atom, R ^ is an ethoxy group, is a β-cyanoethyl group, V ₂ is an allyl group, Vj is an acetylamino group, 150 parts of a pre-standardized liquid containing 27¾ stable crystallographic form of the compound of formula 3, in which X is a chlorine atom, Y is a nitro group, Rj is a hydrogen atom, R ₂ is an ethoxy group, Vp V ₂ are benzyl groups, Vj is an acetylamino group, homogenized in and stirring for 2-3 hours, followed by a Netsch mill or other grinder with 230 parts Reax 32 (sodium salt of lignosulfonic acids) and 11.5 parts SBO humidifier for 4-6 hours.

After dilution with 3000 parts of water, 10 parts of Olan SA (anti-dusting agent) are added to the blended suspension and dried in an Anhydro spray dryer with an inlet air temperature of the dryer 165-175 ° and an air outlet 80-85 °. The obtained dyeing agent micropowder permanently dyes polyester products and fibers at the temperature of 130-140 'in rapid dyeing machines with circulation bath for 5-15 minutes to an intense brown color with a red-blue shade. Dyeing after rinsing in water and light washing without reducing-cleansing treatment are characterized by high uniformity and high usability resistance: light 6 °, friction 4-5 °, 4-5 °, wet factors 4-5 °, 5 °, dry cleaning 5 , 5 °, heat treatment 4-5 °, 3-4 °.

Example IV. 2000 parts 25¾ crude paste compound of a stable crystal form of formula 2, wherein _R1 and _R? is a methyl group, 800 parts of 27¾ crude paste compound of a stable crystal form of the formula 3 wherein X is cyano, Y and R ₂ is hydrogen, R ₁ is methyl, Vj and V ₂ are a β -acetoksyetylową 600 part 20¾ crude paste compound of a stable crystal form of the formula 3 wherein X is chloro, Y represents nitro, R is hydrogen, R ₂ is methoxy, β is a -cyjanoetylową, V ₂ is allyl,

Vj is acetylamino, 300 parts of 27¾ crude paste compound of a stable crystal form of the formula 3 wherein X is chloro, Y represents nitro, R is hydrogen, R ₂ is methoxy, and V ₂ represents a β- acetoxyethyl, denotes an acetylamino group, and homogenized in a mixer for 1-2 hours. It is then ground with 460 parts Reax 32 and 22 parts SBO humidifier in a grinding mill for 3-5 hours. After grinding most of the particles 1-2, the reaction mass is diluted with 5000 parts of water, 20 parts of Olan SA are added and dried in a spray dryer at an inlet air temperature of 110-125 ° C and an outlet air temperature of 75-80 °.

The obtained coloring agent is characterized by a very fine disintegration and a very stable dispersion under the conditions of rapid dyeing. It evenly and permanently colors polyester products in devices with a bath circuit at a temperature of 130-140 ° for 10-20 minutes to an intense brown color with a red tinge. Dyes without reduction and cleansing treatment are characterized by high resistance to: light 6 °, friction 4-5 °, 4-5 °, wet factors 4-5 °, 4-5 °, 5 °, dry cleaning 5 °, 5 °, 5 °, heat treatment 4-5 °, 3-4 °.

Claims (1)

Patent claim A brown-colored coloring agent for polyester products, containing dyes with the addition of dispersing, wetting and anti-dusting auxiliaries, 152,460, comprising: 0-65 parts by weight of compounds of formula I in which X is hydrogen or chlorine, or methyl or ethyl, methoxy or ethoxy, phenylazo, carboxy ester COOR5 in which X is alkyl with 1- 4 carbon atoms, Y is hydrogen or chlorine or nitro or cyano, Z is alkyl of 1-4 carbon atoms or group (CHPflCOOR "where R 'is alkyl of 1-4 carbon atoms, n = 1-5 or the group (CH 1 HOR 2, in which R j is a methyl or ethyl radical, n = 1-4, 0-70 parts by weight of compounds of formula 2, in which R 2 is a methyl or ethyl group, R "is a hydrogen atom or a methyl group 10-30 parts by weight of compounds of formula III in which X is hydrogen or chlorine or hydroxy or cyano, Y is hydrogen or nitro, R5 is hydrogen or methyl, R5 is hydrogen , means the following groups: β-cyanoethyl, benzyl, β-acetoxyethyl, β-hydroxyethyl, allyl, means the groups: fi -cyanoethyl, benzyl, β-acetoxyethyl, β-hydroxyethyl or allyl, Vj is hydrogen or acylamino group NHCOR-j, in which Rj is alkyl □ 1-2 carbon atoms, 0-40 parts by weight of compounds of formula 3 in which X is chlorine or bromine atom, Y is nitro group, R5 is hydrogen atom, Rj is methoxy or ethoxy group, is NHCOR-j acylamino group, where Rj is alkyl with 1-2 carbon atoms, Vj is β-cyanoethyl group , di-acetoxyethyl, benzyl or allyl means a β-acetoxyethyl, benzyl or allyl group, 0-20 parts by weight of compounds of formula 4 in which X is amino or hydroxy, Y is hydrogen or phenol hydroxy or phenylmethoxy, Z is an amino or aminophenyl group, V is a hydrogen atom or a hydroxyl group, R is a hydrogen atom or an amino group, 0-20 parts by weight of compounds of formula 5, in which X, Y, Z, V are hydroxyl or amino groups, the center being k contains at least two compounds represented by the formulas 1, 2, 3, 4, 5, one of them is a compound of the formula 1 or 2, and the compounds used have a stable crystallographic form. pattern Ί ORi 1 ^ 2. pattern 2 pattern 4 V 0 X ± 6r // - 2 / 2. 0 y pattern 5 152 460 Department of Publishing of the UP RP. Circulation 100 copies. Price PLN 3,000