WO2016142955A4 - Storage stable solutions of optical brightening agents - Google Patents

Storage stable solutions of optical brightening agents Download PDF

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Publication number
WO2016142955A4
WO2016142955A4 PCT/IN2016/050082 IN2016050082W WO2016142955A4 WO 2016142955 A4 WO2016142955 A4 WO 2016142955A4 IN 2016050082 W IN2016050082 W IN 2016050082W WO 2016142955 A4 WO2016142955 A4 WO 2016142955A4
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WO
WIPO (PCT)
Prior art keywords
straight chain
coo
formula
brightening agent
optical brightening
Prior art date
Application number
PCT/IN2016/050082
Other languages
French (fr)
Other versions
WO2016142955A1 (en
Inventor
Abhay Bhalchandra DESHPANDE
Milind Narayan KOLHE
Original Assignee
Deepak Nitrite Limited
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 Deepak Nitrite Limited filed Critical Deepak Nitrite Limited
Publication of WO2016142955A1 publication Critical patent/WO2016142955A1/en
Publication of WO2016142955A4 publication Critical patent/WO2016142955A4/en

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Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H21/00Non-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
    • D21H21/14Non-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
    • D21H21/30Luminescent or fluorescent substances, e.g. for optical bleaching
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40Nitrogen atoms
    • C07D251/54Three nitrogen atoms
    • C07D251/68Triazinylamino stilbenes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14Styryl dyes
    • C09B23/148Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072Preparations with anionic dyes or reactive dyes
    • C09B67/0073Preparations of acid or reactive dyes in liquid form
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H17/00Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03Non-macromolecular organic compounds
    • D21H17/05Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07Nitrogen-containing compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to optical brighteners of Formula I and a process for preparing the same. The present invention also discloses aqueous solutions of optical brighteners of Formula I.

Claims

AMENDED CLAIMS
received by the International Bureau on 30 September 2016 (30.09.16)
WE CLAIM:
1.
Figure imgf000002_0001
{[N^J^R^HCH^CONH , . p}>,q
Formula I
wherein,
R and R' independent of each other are hydrogen, C1-C4 straight chain or branched alkyl;
Ri and Ri ' independent of each other are hydrogen, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched hydroxyalkyl, -CH2CH2CONH2, -CH2CH2CN, -CH2CH2COO", -CH2COO";
R2 and R2' independent of each other are hydrogen, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched hydroxyalkyl, -CH2COO\ CH(COO" )CH2COO", CH(COO~)CH2CH2COO~, CH2CH2S03 ";
R3 and R4 independent of each other are hydrogen, C 1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched hydroxyalkyl, -CH2CH2CONH2; M+ represents Li+, Na+, K+ or a quaternary ammonium ion derived from mono-, di- or trialkanolamine, or a mixture thereof, with 'p' less than or equal to 0.8 and 'q' is the number of functional groups in the optical brightener molecule, that are capable of forming a quaternary ammonium salt; and n is 0, 1 or 2
2. The optical brightening agent as claimed in claim 1, wherein and R' each are H;
Ri , Ra, R' I and R each are -CH2CH2OH;
M is Na ;
R3 and R4 each are -CH3;
p is 0.25;
q is 2; and
n is 0
3. The optical brightening agent as claimed in claim 1, R and R' each are H;
Ri, R2, R 1 and R 2 each are -CH2CH2OH;
M is Na;
R and R4 each are -CH2CH3;
p is 0.25;
q is 2; and
n is 0
4. The optical brightening agent as claimed in claim 1, wherein
R and R' each are H;
Ri, R2, R'I and R 2 each are -CH2CH2OH;
M is Na;
R3 and R4 each are -CH2CH3;
p is 0.8;
q is 4; and
n is 1
5. The optical brightening agent as claimed in claim 1 , wherein R and R each are H;
Ri , R2, R Ί and R 2 each are -CH2CH2OH;
M is Na;
R3and R4 each are -CH2CH3;
p is 0.4;
q is 6; and
n is 2
6. The optical brightening agent as claimed in claim 1, wherein
R and R each are H;
Ri, R2, R i and R 2each are -CH2CH3;
M is Na;
R3 and R4 each are -CH2CH ;
p is 0.66;
q is 6; and
n is 2
7. A process for preparing an optical brightening agent of Formula I, the process comprising mixing compound of Formula II and compound of Formula III to obtain com ound of Formula I.
Figure imgf000005_0001
Formula III
wherein,
R and R' independent of each other are hydrogen, C 1-C4 straight chain or branched alkyl;
Ri and Ri ' independent of each other are hydrogen, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched hydroxyalkyl, -CH2CH2CONH2, -CH2CH2CN,
Figure imgf000005_0002
R2 and R2' independent of each other are hydrogen, C1-C4 straight chain or branched alkyl, Ci-C4 straight chain or branched hydroxyalkyl, -CH2COO\ CH(COO) CH2COO", CH(COO")CH2CH2COO\ CH2CH2S03 ~; R-3 and R4 independent of each other are hydrogen, C1-C4 straight chain or branched alkyl, C1-C4 straight chain or branched hydroxyalkyl, -CH2CH2CONH2; represents Lf, Na+, K+ or a quaternary ammonium ion derived from mono-, di- or trialkanolamine, or a mixture thereof, with 'p' less than or equal to 0.8 and 'q' being the number of functional groups in the optical brightener molecule, that are capable of forming a quaternary ammonium salt; and n is 0, 1 or 2
8. The process as claimed in claim 7, comprising adjusting pH of the mixture with a base.
9. The process as claimed in claim 8, wherein the base is selected from NaOH, KOH, LiOH, mono- di- or tri-alkyl amine or mono-, di- or tri-alkanolamine.
10. The process as claimed in claim 7, comprising mixing compound of Formula II and compound of Formula III in the presence of water.
11. A stable aqueous solution comprising the optical brightening agent claimed in claim 1.
12. The stable aqueous solution as claimed in claim 11, wherein the optical brightening agent of Formula I is present at a concentration ranging from 10% to 60%.
13. The stable aqueous solution as claimed in claim 11 optionally comprising additives such as carriers, antifreeze, defoamers, solubilizing agents, preservatives, complexing agents, inorganic or organic salts.
14. Use of the optical brightening agent of Formula I as claimed in claim 1 , for brightening woven and non-woven fabrics, paper, paperboards.
15. A method for optically brightening woven and non-woven fabrics, paper and paperboards by adding the optical brightening agent of Formula I as claimed in claim 1.
16. The method as claimed in claim 16 comprising adding an aqueous solution of the optical brightening agent of Formula I to woven and non-woven fabrics, paper and paperboards.
PCT/IN2016/050082 2015-03-10 2016-03-09 Storage stable solutions of optical brightening agents WO2016142955A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3955MU2014 2015-03-10
IN3955/MUM/2014 2015-03-10

Publications (2)

Publication Number Publication Date
WO2016142955A1 WO2016142955A1 (en) 2016-09-15
WO2016142955A4 true WO2016142955A4 (en) 2016-11-24

Family

ID=56072391

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2016/050082 WO2016142955A1 (en) 2015-03-10 2016-03-09 Storage stable solutions of optical brightening agents

Country Status (1)

Country Link
WO (1) WO2016142955A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3710632T3 (en) * 2017-12-22 2022-02-21 Archroma Ip Gmbh Optical brightener for whitening paper
EP3623392B1 (en) 2018-09-14 2023-07-19 Archroma IP GmbH Optically brightened latexes

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3012971A (en) 1959-04-07 1961-12-12 Du Pont Whitening composition for paper
DE3502038A1 (en) 1985-01-23 1986-07-24 Sandoz-Patent-GmbH, 7850 Lörrach AQUEOUS BRIGHTENING DEVICES AND THEIR USE IN THE PAPER LINE
GB0100610D0 (en) 2001-01-10 2001-02-21 Clariant Int Ltd Improvements in or relating to organic compounds
RU2368655C2 (en) 2003-09-19 2009-09-27 Циба Спешиалти Кэмикэлз Холдинг Инк. Aqueous solutions of fluorescent optical bleaching agents
EP1752453A1 (en) * 2005-08-04 2007-02-14 Clariant International Ltd. Storage stable solutions of optical brighteners
BRPI0821657B1 (en) 2007-12-12 2018-06-05 Archroma Ip Gmbh STABLE SOLUTIONS FOR STORAGE OF OPTICAL CLARIFICANTS, THEIR PREPARATION PROCESS AND THEIR USES AS WELL AS PAPER BLANKING PROCESSES
ITMI20111449A1 (en) 2011-07-29 2013-01-30 3V Sigma Spa AQUEOUS SOLUTIONS OF FLUORESCENT BLEACHING AGENTS
ITMI20121220A1 (en) 2012-07-12 2014-01-13 3V Sigma Spa STYLBENIC COMPOUNDS

Also Published As

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WO2016142955A1 (en) 2016-09-15

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