EP0061173B1 - Verfahren zum Färben von Papier - Google Patents

Verfahren zum Färben von Papier Download PDF

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Publication number
EP0061173B1
EP0061173B1 EP82102280A EP82102280A EP0061173B1 EP 0061173 B1 EP0061173 B1 EP 0061173B1 EP 82102280 A EP82102280 A EP 82102280A EP 82102280 A EP82102280 A EP 82102280A EP 0061173 B1 EP0061173 B1 EP 0061173B1
Authority
EP
European Patent Office
Prior art keywords
paper
cationic
dye
water
added
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP82102280A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0061173A1 (de
Inventor
Hans-Juergen Dr. Degen
Wolf Dr. Guender
Guenter Dr. Frey
Werner Dr. Streit
Rolf Dr. Fikentscher
Klaus Dr. Wulz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to AT82102280T priority Critical patent/ATE8675T1/de
Publication of EP0061173A1 publication Critical patent/EP0061173A1/de
Application granted granted Critical
Publication of EP0061173B1 publication Critical patent/EP0061173B1/de
Expired legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
    • D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/919—Paper

Definitions

  • DE-A-24 58 443 discloses a process for producing a colored paper, in which reactive dyes are used as the dye and polyalkyleneimines, which can optionally be quaternized, are used as the auxiliary.
  • the coloring can be carried out both in the mass and after the leaf formation.
  • DE-A-20 12 217 From DE-A-20 12 217, it is known from DE-A-20 12 217 to carry out the dyeing in the presence of cationic polymeric compounds and to remove the cationic dyes only after the addition of the cationic polymers Add compound to the fabric.
  • the known auxiliaries for processes for dyeing paper have an insufficient activity when using acid dyes or direct dyes.
  • the object of the invention is to provide an effective aid for a process for dyeing paper with acid dyes and / or direct dyes in an aqueous medium, which allows papers to be dyed with high color strength while largely avoiding the two-sided cylinder of the dyeing.
  • water-soluble reaction products are used as cationic auxiliaries, which are obtainable by reaction of alkylating agents which have an aromatic substituent with cationic polyelectrolytes.
  • Particularly effective auxiliaries for the process according to the invention are obtained if the water-soluble reaction products of alkylating agents which have an aromatic substituent and the cationic polyelectrolyte are modified in a second stage by reaction with cyanamide and / or dicyandiamide.
  • Suitable dyes for the process according to the invention are acidic dyes or direct dyes and also mixtures of the two classes of dyes mentioned.
  • the dyes of the classes mentioned can be found in the Color Index. Acid dyes are given, for example, in the Color Index, Volume 1, 3rd edition, The Society of Dyers and Colorists and American Association of Textile Chemists and Colorists, pages 1003-1560. Some typical acid dyes that are particularly suitable for dyeing paper are, for example, the acid yellow dyes Ci 13 065 and 47 035, the orange dyes Cl 13 090, Cl 15 575 and Cl 15 510 and the red acid dyes Cl 45 380 and Cl 15 620. Direct dyes are given in the Color Index, Volume 2, on pages 2007 to 2477.
  • Typical direct dyes that are usually used for dyeing paper are the yellow direct dyes CI 29 000, CI 24 895, Ci 13 950, CI 29 025, Cl 40 000, Cl 40 001 and CI 24 890, the orange direct dyes Cl 40 215 , Cl 40 265 and 29 156, the red direct dyes CI 29 175, Cl 28 160, Cl 22120 and Cl 25 410, the blue direct dyes Cl 23 155 and Cl 24 340 and the violet direct dye Cl 25 410.
  • the aromatic substituents of the alkylating agent can carry other substituents in addition to the groups mentioned, for. B. C i - to C 12 alkyl groups, chlorine, bromine, phenyl, p-chloromethylphenyl, hydroxymethyl and chloromethyl.
  • Benzyl chloride is preferably used as the alkylating agent.
  • cationic polyelectrolytes can be used as the second component for the production of the cationic auxiliaries.
  • the cationic polyelectrolytes preferably contain aminoalkyl groupings.
  • examples of cationic polyelectrolytes are polyethyleneimines which have at least 5 aminoalkyl groups, polyvinylamines and crosslinking products of ammonia or amines, in particular diamines or oligoamines with 1,2-dichloroethane, epichlorohydrin, dichlorohydrin ether or chlorohydrin ether of at least dihydric alcohols.
  • Dichlorohydrin ether is obtained, for example, by reacting 2 moles of epichlorohydrin with one mole of water.
  • Chlorohydrin ethers of at least dihydric alcohols are derived from glycols or polyols, the molecular weight of which is at most 300 and which are obtained by reacting 1 to 1.5 moles of epichlorohydrin per mole of OH groups in polyhydric alcohol or polyglycol with acid catalysis (e.g. H 2 S0 4 or BF 3 ) can be obtained.
  • acid catalysis e.g. H 2 S0 4 or BF 3
  • Suitable diamines or oligoamines are, for example, ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, bis-aminopropylethylenediamine, tetraethylenepentamine, piperazine, aminoethylpiperazine, aminopropylpiperazine, diaminoethylpiperazine and diaminopropylpiperazine.
  • the viscosity of the crosslinking products of ammonia and the diamines or oligoamines in a 40% aqueous solution is at most 40,000 mPas.
  • Polyvinylamines are produced by free-radically polymerizing vinylformamide and saponifying the polymer in an acidic environment.
  • Further cationic polyelectrolytes are condensation products containing carbonamide groups, are grafted onto the alkyleneimine units.
  • This class of substances is primarily polyamidoamines which are obtained by reacting dicarboxylic acids having 4 to 10 carbon atoms with polyalkylene polyamines which have 3 to 19 basic nitrogen atoms in the molecule.
  • Suitable dicarboxylic acids are, for example, succinic acid, maleic acid, adipic acid, glutaric acid, suberic acid, sebacic acid or terephthalic acid.
  • mixtures of dicarboxylic acids e.g. B.
  • adipic acid and glutaric acid or maleic acid and adipic acid.
  • Adipic acid is preferably used.
  • carboxylic acids are condensed with polyalkylene polyamines or mixtures thereof which contain 3 to 10 basic nitrogen atoms in the molecule, e.g. B. diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenetriamine, tripropylenetetramine or dihexamethylenetriamine.
  • the amines can optionally contain up to 10% by weight of a diamine, such as ethylenediamine or hexamethylenediamine.
  • Condensation products containing carbonamide groups are also obtained by reacting (meth) acrylic ester with diamines, such as ethylenediamine and hexamethylenediamine, or oligoamines.
  • diamines such as ethylenediamine and hexamethylenediamine, or oligoamines.
  • a further possibility for the preparation of such compounds is to condense urea with bis-aminoethylmethylamine.
  • the water-soluble condensation products containing carbonamide groups mentioned are modified cationically by introducing alkyleneimine units.
  • the easiest way to do this is e.g. B. in such a way that the condensation products in the presence of Lewis acids, for. B. boron trifluoride etherate or sulfuric acid, alkyleneimines, especially ethyleneimine, grafted.
  • Lewis acids for. B. boron trifluoride etherate or sulfuric acid, alkyleneimines, especially ethyleneimine, grafted.
  • alkyleneimines especially ethyleneimine
  • grafting reaction based on 100 parts by weight of a condensate containing carbonamide groups, 20 to 400, preferably 50 to 300 parts by weight of ethyleneimine are used. Products of this type are known for example from DE-B-24 34 816.
  • Alkyleneimine groups can also be produced by reacting aminoalkylsulfuric acid half-esters with the condensates containing carbonamide groups in the alkaline pH range.
  • An aminoethylation of the condensates containing carbonamide groups is possible, for example, by reacting these products with ß-aminoethylsulfonic acid half-ester.
  • the cationic polyelectrolytes are completely or only partially reacted with the alkylating agents which have an aromatic substituent. At least 10% of the aminoalkyl groups of the cationic polyelectrolyte should be reacted with the alkylating agents containing an aromatic substituent. Especially in the case of the reaction products from piperazines and epichlorohydrin, after a partial quaternization of the cationic polyelectrolytes, the proportion of quaternary nitrogen atoms in the polyelectrolyte is preferably 30 to 60%.
  • auxiliaries are obtained if the reaction products of alkylating agents which have an aromatic substituent and the cationic polyelectrolyte are modified in a second stage with cyanamide or dicyandiamide or mixtures of cyanamide and dicyandiamide.
  • cyanamide or dicyandiamide or mixtures of cyanamide and dicyandiamide 1 to 100, preferably 5 to 20 parts by weight of cyanamide and / or dicyanamide are used per 100 parts by weight of a partially alkylated cationic polyelectrolyte.
  • the reaction is carried out in aqueous solution at temperatures in the range from 70 to 100.degree.
  • paper is colored in the presence of the cationic auxiliaries described above.
  • the dyeing is preferably carried out in bulk, i.e. H. during the manufacture of the paper.
  • acidic dye, direct dyes or a mixture of dyes of the two classes mentioned and the cationic auxiliary are added to the paper stock and the paper stock is dewatered in the customary manner on a paper machine.
  • the colored paper is then obtained directly.
  • the order in which dyes or cationic auxiliaries are added to the paper stock is not decisive for the failure of the dyeings.
  • the dyes in question and the cationic auxiliary can be added to the paper stock, and dyes first and then the cationic auxiliary added to the material, or the auxiliary and then the dyes added first.
  • the cationic auxiliary is used in an amount of 10 to 300% by weight, preferably 30 to 150% by weight, based on the dye.
  • the dyeing process can be carried out in a wide temperature range, e.g. B. from room temperature to about 60 ° C, preferably from 20 to 50 ° C.
  • the paper can also be dyed according to the invention after sheet formation by successively applying the cationic auxiliary and one or more dyes in question to the surface of the paper, e.g. B. by spraying the auxiliary and then applying the dye in the size press. It is also possible to start with the paper in bulk one of the cationic auxiliaries and then apply a solution of the dyes in water in the size press. The dye can also be added to the mass and the cationic auxiliary agent can be applied in the size press. It is only important that the dyeing is carried out in combination with the cationic auxiliary. When drying paper dyed with acid dyes, the problem of color two-sidedness (cylinder two-sidedness) often occurs in practice.
  • the process according to the invention gives dyeings with high color strength and practically uniform dyeings on the top and bottom of the paper formed.
  • Another advantage over known processes is the fact that the process according to the invention, in particular in the case of acidic dyes, achieves substantially better retention of the dye than is the case with the known processes.
  • the paper machine wastewater contains about half or less of unused dyes compared to paper machine wastewater from dyeing processes in which known aids are used.
  • papers dyed in accordance with the invention have a high fastness to bleeding in contact with other materials, such as, for. B. papers, food, textiles in the presence of a wetting liquid such.
  • the rating “none for a loss of color strength of 0 to 5% corresponds to the fact that color strength differences of this magnitude are difficult to perceive by the human eye and therefore play no role in practice.
  • the ethylenimine modified polyamidoamine was benzylated by adding 192 parts of the 50.8% aqueous resin solution with 311 parts of water, heating to 80 ° C and within half an hour with 76 parts of benzyl chloride at a temperature in the range of 80 to 90 ° C brought together. After the addition of the benzyl chloride had ended, the reaction solution was heated to 90 ° C. for a further hour and then cooled. A 30.1% strength aqueous solution of a benzylated polyamidoamine grafted with ethyleneimine was obtained.
  • a solution of 21 g of cyanamide in 21 g of distilled water was then added all at once to the reaction solution and the mixture was stirred at 90 ° C. for 5 hours.
  • the aqueous solution was then diluted with 89 g of distilled water and 366 g of a 50% strength aqueous solution of a polyethyleneimine modified with benzyl chloride and cyanamide were obtained.
  • the wet paper was dried between two absorbent papers on a 90 ° C cylinder with felt covering within 10 minutes without turning. Before drying, a 5 cm diameter plastic disc was placed on the side of the damp paper facing the felt. The coloration of the paper sheets provided a smooth color image and showed no two-sided cylinder.
  • Example 1 is repeated with the exception that the absence of the cationic auxiliary is carried out. 95% of the dye used is then found in the draining water. The color of the paper is very weak, shows an unsteady color image and is very strong on both sides of the cylinder.
  • Example 2 was repeated with the exception. that work was carried out in the absence of tool 1. 53% of the dye used was in the draining water. The color picture was calm. but showed a pronounced two-sided cylinder.
  • Example 3 is repeated. however, work is carried out in the absence of tool 1. 18% of the dye used was in the draining water. The determination of the bleeding fastness according to DIN 53 991, sheet 1 resulted in the following values:
  • Example 1 was repeated several times. however, instead of 0.33 g of auxiliary 1, the amounts of auxiliary given in table 1 and the other auxiliary also given in table 1 were used in the given amounts. Table 1 also shows the dye content in the waste water. based on the dyes used.
  • Example 1 If Example 1 is repeated, except that the process is carried out in the absence of auxiliary 1, but as an auxiliary polyethyleneimine having a molecular weight of 1,500 or 860, the dye content in the wastewater roughly doubles compared to the auxiliaries used in Table 1. In contrast to the cationic auxiliaries to be used according to the invention, no further decisive improvement in dye retention occurs with the polyethyleneimines, even if these products are used in a larger amount.
  • Example 1 is repeated with the exception that the auxiliaries indicated in Table 3 were used in the amounts indicated there.
  • This example shows that when using the aids to be used according to the invention, a certain color strength of the paper sheet is achieved faster than when using known aids.
  • the color strength of the colored paper was determined from its reflectance curve.
  • the color strength obtained with the auxiliaries according to the invention at a certain concentration, based on the fiber used, is set to 100 in each case and compared with the color strength which is achieved when the corresponding precursor of the auxiliaries according to the invention which is not reacted with benzyl chloride is used.
  • Example 1 If Example 1 is repeated, with the exception that auxiliaries 9 to 11 are used instead of the auxiliary 1 according to the invention, and alkylating agents which do not carry any aromatic groups have been used for their production, the wastewater of the laboratory sheet former contains significantly higher levels of dye than in Use of aids according to the invention. This becomes clear when the results from Table 1 are compared with Table 4.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)
  • Color Printing (AREA)
  • Coloring (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Dental Preparations (AREA)
  • Orthopedics, Nursing, And Contraception (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
EP82102280A 1981-03-25 1982-03-19 Verfahren zum Färben von Papier Expired EP0061173B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82102280T ATE8675T1 (de) 1981-03-25 1982-03-19 Verfahren zum faerben von papier.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3111712 1981-03-25
DE19813111712 DE3111712A1 (de) 1981-03-25 1981-03-25 Verfahren zum faerben von papier

Publications (2)

Publication Number Publication Date
EP0061173A1 EP0061173A1 (de) 1982-09-29
EP0061173B1 true EP0061173B1 (de) 1984-07-25

Family

ID=6128235

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82102280A Expired EP0061173B1 (de) 1981-03-25 1982-03-19 Verfahren zum Färben von Papier

Country Status (13)

Country Link
US (1) US4383834A (fi)
EP (1) EP0061173B1 (fi)
JP (1) JPS57171797A (fi)
AT (1) ATE8675T1 (fi)
AU (1) AU8186082A (fi)
CA (1) CA1172004A (fi)
DE (2) DE3111712A1 (fi)
DK (1) DK132682A (fi)
ES (1) ES510756A0 (fi)
FI (1) FI70740C (fi)
NO (1) NO820961L (fi)
NZ (1) NZ200113A (fi)
ZA (1) ZA821981B (fi)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3732981A1 (de) * 1987-09-30 1989-04-13 Basf Ag Verfahren zum faerben von papier
DE4233040A1 (de) * 1992-10-01 1994-04-07 Basf Ag Verfahren zum Färben von Papier
US6423183B1 (en) * 1997-12-24 2002-07-23 Kimberly-Clark Worldwide, Inc. Paper products and a method for applying a dye to cellulosic fibers
US6270625B1 (en) * 1999-06-29 2001-08-07 The Mead Corporation Method for manufacturing colored stripped paper
US6379498B1 (en) * 2000-02-28 2002-04-30 Kimberly-Clark Worldwide, Inc. Method for adding an adsorbable chemical additive to pulp during the pulp processing and products made by said method
US6749721B2 (en) 2000-12-22 2004-06-15 Kimberly-Clark Worldwide, Inc. Process for incorporating poorly substantive paper modifying agents into a paper sheet via wet end addition
US7749356B2 (en) * 2001-03-07 2010-07-06 Kimberly-Clark Worldwide, Inc. Method for using water insoluble chemical additives with pulp and products made by said method
US6582560B2 (en) 2001-03-07 2003-06-24 Kimberly-Clark Worldwide, Inc. Method for using water insoluble chemical additives with pulp and products made by said method
US20030221806A1 (en) * 2002-05-30 2003-12-04 Naumann Larry J. Dyed or tinted paper and method of making same
US6916402B2 (en) * 2002-12-23 2005-07-12 Kimberly-Clark Worldwide, Inc. Process for bonding chemical additives on to substrates containing cellulosic materials and products thereof
US20040244929A1 (en) * 2003-06-03 2004-12-09 Henke Jason D. Process for producing a fade-resistant paper
CN100595378C (zh) * 2003-12-02 2010-03-24 大王制纸株式会社 着色卫生薄纸及其制造方法
US7670459B2 (en) * 2004-12-29 2010-03-02 Kimberly-Clark Worldwide, Inc. Soft and durable tissue products containing a softening agent
US20070154398A1 (en) * 2005-12-30 2007-07-05 Industrial Technology Research Institute Block copolymers and nano micelles comprising the same
BR112012002344B1 (pt) 2009-08-05 2019-12-03 Int Paper Co processo para preparar uma folha de polpa fofa, folha de polpa fofa e produto absorvente
EP2462276B1 (en) * 2009-08-05 2014-11-05 International Paper Company Dry fluff pulp sheet additive
MY162376A (en) 2009-08-05 2017-06-15 Shell Int Research Method for monitoring a well
ES2952420T3 (es) 2010-07-20 2023-10-31 Int Paper Co Composición que contiene un metal catiónico multivalente y un agente antiestático que contiene amina y métodos de fabricación y uso
CN103003488B (zh) * 2010-07-22 2015-04-15 国际纸业公司 使用阳离子型染料和解胶剂型表面活性剂制造绒毛浆片材的方法和由该方法制得的绒毛浆片材

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2884057A (en) * 1954-02-25 1959-04-28 American Cyanamid Co Paper of improved dry strength and method of making same
US3049468A (en) * 1957-12-23 1962-08-14 Ici Ltd Manufacture of coloured paper
US3926553A (en) * 1970-02-02 1975-12-16 Uniroyal Inc Method of rendering polyolefins dyeable with anionic dyes
DE2343261A1 (de) * 1973-08-28 1975-04-10 Consortium Elektrochem Ind Zusatzmittel fuer die papierherstellung
GB1438903A (en) * 1974-01-10 1976-06-09 Ici Ltd Paper colouration process
DK552779A (da) * 1978-12-29 1980-06-30 Ciba Geigy Ag Fremgangsmaade til farvning og betrykning af fibermaterialer under anvendelse af kvaternaere polymeriserede ammoniumsalte som hjaelpemiddel

Also Published As

Publication number Publication date
FI70740B (fi) 1986-06-26
ES8303581A1 (es) 1983-02-01
DE3111712A1 (de) 1982-10-07
FI70740C (fi) 1986-10-06
DE3260434D1 (en) 1984-08-30
NZ200113A (en) 1984-09-28
US4383834A (en) 1983-05-17
JPS57171797A (en) 1982-10-22
ES510756A0 (es) 1983-02-01
ATE8675T1 (de) 1984-08-15
AU8186082A (en) 1982-09-30
CA1172004A (en) 1984-08-07
EP0061173A1 (de) 1982-09-29
FI820653L (fi) 1982-09-26
ZA821981B (en) 1983-02-23
DK132682A (da) 1982-09-26
NO820961L (no) 1982-09-27

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