WO2021165083A1 - Utilisation de dérivés de polyalkylèneimine dans des compositions de nettoyage - Google Patents

Utilisation de dérivés de polyalkylèneimine dans des compositions de nettoyage Download PDF

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Publication number
WO2021165083A1
WO2021165083A1 PCT/EP2021/052950 EP2021052950W WO2021165083A1 WO 2021165083 A1 WO2021165083 A1 WO 2021165083A1 EP 2021052950 W EP2021052950 W EP 2021052950W WO 2021165083 A1 WO2021165083 A1 WO 2021165083A1
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WO
WIPO (PCT)
Prior art keywords
backbone
naphthylene
polyalkyleneimine
cleaning composition
alkyl
Prior art date
Application number
PCT/EP2021/052950
Other languages
English (en)
Inventor
Catharina WOHLMUTH
Huiguang Kou
Roland Ettl
Eva-Maria REIS-WALTHER
Susanne Carina ENGERT
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
Publication of WO2021165083A1 publication Critical patent/WO2021165083A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines

Definitions

  • the present invention relates to the use of polyalkyleneimine derivatives in cleaning composi tions and to cleaning compositions comprising polyalkyleneimine derivatives.
  • a bleaching system commonly applied in powder laundry detergents is for example hydrogen peroxide, which is difficult to be formulated in liquid detergent systems because hydrogen peroxide is not stable in liquid system for prolonged periods of time as is required to ensure a shelf life of at least several months for the liquid detergent. Therefore, the performance of liquid detergents for removal of bleachable stains is until now limited and improved performance regarding removal of bleachable stains by laundry detergents is highly desirable.
  • Alkoxylated polyalkyleneimines are known as additives for stain removal in detergent formula tions and are applied in liquid laundry detergents, but they only show limited performance with regard to removal of bleachable stains.
  • Alkoxylated polyalkyleneimine derivatives are so far only known as dispersants for pigments.
  • WO2017/140538 discloses polyalkyleneimine based polyesters having polyester groups used as dispersant for pigments.
  • the term “obtainable by” means that corresponding products do not necessarily have to be produced (i.e. obtained) by the corresponding method or process de scribed in the respective specific context, but also products are comprised which exhibit all fea tures of a product produced (obtained) by said corresponding method or process, wherein said products were actually not produced (obtained) by such method or process.
  • the term “obtainable by” also comprises the more limiting term “obtained by”, i.e. products which were actually produced (obtained) by a method or process described in the respective specific con text.
  • the present invention relates to the use of a polymer having a) a polyalkyleneimine backbone; b) at least one aromatic moiety P1 wherein
  • n is an integer from 0 to 100
  • Ai is independently selected from linear or branched alkylenes having 2 to 18 carbon atoms
  • n A2 for each individual repetition unit n A2 is independently selected from linear or branched alkylenes having 2 to 18 carbon atoms, in a cleaning composition.
  • the present invention relates to a cleaning composition
  • a cleaning composition comprising
  • n is an integer from 0 to 20
  • Ai is independently selected from linear or branched alkylenes having 2 to 18 carbon atoms
  • n A2 for each individual repetition unit n A2 is independently selected from linear or branched alkylenes having 2 to 18 carbon atoms.
  • the polymers of the present invention for use in cleaning compositions and for cleaning compo sitions have a polyalkylenimine backbone, to which the at least one aromatic moiety P1 and the at least one moiety P2 are attached.
  • the polyalkyleneimine backbone may be linear or branched.
  • the polyalkyleneimine backbone is in particular a linear or branched poly(C2-C4-alkyleneimine), more particular a linear or branched polypropyleneimine, a linear or branched poly(ethyleneimine-co-propyleneimine) or a linear or branched polyethyleneimine or a mixture thereof.
  • the polyalkyleneimine backbone is a linear or branched polyethyleneimine.
  • the polyalkylenimine backbone has a weight average molecular weight (M w ) of from 100 to 10000 g/mol. In one embodiment of the present invention the weight average molecular weight is in the range of from 250 to 5000 g/mol. In another em- 190172
  • the weight average molecular weight of the polyalkylenimine is in the range of from 600 to 2500 g/mol.
  • Both moieties P1 and P2 are attached to nitrogen atoms of the polyalkyleneimine backbone. It is apparent to a skilled person that polymers of the invention may have nitrogen atoms, which do not carry moieties P1 and P2. These nitrogen atoms are basic and susceptible to protonation or quaternization. Polymers of the invention, which have nitrogen atoms, which do not carry moieties P1 and P2, will usually have an amine number > 0 mg KOH/g, e.g. in the range from 2 to 150 mg KOH/g, in particular from 5 to 50 mg KOH/g. In one embodiment of the present in vention the polyalkylene imine backbone in addition to the moieties P1 and P2 has protonated or quaternized amino groups. In this embodiment, the amount of protonated or quaternized amino groups is generally from 0.01 to 0.5 mol/kg.
  • the polyalkylene imine backbone in addition to the moieties P1 and P2 does not have quaternized amino groups.
  • the amount of quaternized amino groups is less than 0.01 mol/kg.
  • the polyalkyleneimines of the present invention have a molar ratio of from 0.01 to 0.5 aromatic moieties P1 per nitrogen atom in the polyalkyleneimine backbone. In another embodiment the molar ratio of aromatic moieties P1 to nitrogen atoms in the polyalkyleneimine backbone is in the range of from 0.02 to 0.4. In a further embodiment the molar ratio of aromatic moieties P1 to nitrogen atoms in the polyalkyleneimine backbone is in the range of from 0.1 to 0.3.
  • the aromatic moiety P1 is selected from the group consisting of 1,2-phenylene, 1,2- naphthylene, 2,3-naphthylene, and 1,8-naphthylene.
  • the aromatic moiety P1 is bound to a ni trogen atom of the polyalkyleneimine backbone via two carbonyl groups, thereby forming a car- boximide group.
  • the point of attachment to the nitrogen atom of the polyalkyleneimine back bone is indicated by the symbol # in P1.
  • the aryl or arylene moieties of P1 are unsubstituted or substituted, e.g.
  • the aromatic P1 moieties may be identical or different. Frequently, they are identical.
  • the Ar in the aromatic moiety P1 is 1,8-naphthylene.
  • Ar in the aromatic moiety P1 is 1,8-naphthylene and the molar ratio of 1,8-naphthylene per nitrogen atom in the polyalkyleneimine backbone is in the range of from 0.01 to 0.3. 190172
  • Each moiety P2 is attached to nitrogen atoms of the polyalkyleneimine backbone. The point of attachment to the nitrogen atom of the polyalkyleneimine backbone is indicated by the symbol # in P2.
  • Each moiety P2 individually and independently from each other moiety P2 comprises a unit A1 which is independently selected from linear or branched alkylenes having 2 to 18 carbon atoms.
  • Each moiety P2 individually and independently from each other moiety P2 comprises may comprise one or more units A2 which are independently selected from linear or branched alkylenes having 2 to 18 carbon atoms.
  • A1 and A2 are independently for each repetition unit selected from the group consisting of ethylene, 1,2- propylene, 1,2-butylene, 2,3-butylene, i-butylene, pentenyl, hexyl, decenyl, dodecyl, tetrade- cenyl and hexadecenyl.
  • A1 and A2 are independently for each repetition unit selected from the group consisting of ethylene, 1,2-propylene, and 1,2-butylene.
  • A1 and A2 are all ethylene.
  • the moiety P2 comprises at least two blocks of different alkylene groups, for example a first block formed by A1 and A2 may first be selected from ethylene, followed by a second block formed by A2 which may be selected from 1,2-propylene. In another embodiment the distribution of alkylene groups for individual units A1 and A2 is random.
  • n is in the range of from 0 to 100. In another embodiment, n is in the range of from 1 to 50. In a further embodiment, n is in the range of from 10 to 35.
  • polyalkyleneimines of the present disclosure may be asymmetrically alkoxylated, meaning that n for one individual moiety P2 is different from the n of another moiety P2.
  • the number n is therefore the average number of substituents of all individual moieties P2.
  • the molar ratio of from 0.1 to 0.99 moieties P2 per nitrogen atom in the pol yalkyleneimine backbone is in the range of from 0.5 to 0.98. In a further embodi ment the molar ratio of moieties P2 to nitrogen atoms in the polyalkyleneimine backbone is in the range of from 0.7 to 0.9.
  • Ar in the aromatic moiety P1 is 1,8-naphthylene
  • the molar ratio of 1,8- naphthylene per nitrogen atom in the polyalkyleneimine backbone is in the range of from 0.02 to 0.3
  • A1 and A2 in P2 are ethylene
  • n is in the range of from 10 to 35
  • the molar ratio of P2 per nitrogen atom in the polyalkyleneimine backbone is in the range of from 0.7 to 0.98.
  • the modified polyalkyleneimines can for example be obtained by the following process: i. A polyalkyleneimine is reacted with at least one of the following dicarboxylic acids select ed from the group consisting of substituted or unsubstituted 1,2-benzenedicarboxylic acid, sub- 190172
  • step (ii) is reacted with at least one alkylene oxide using catalysts and re action conditions well known in the art.
  • cleaning composition includes compositions and formulations de-signed for cleaning soiled material.
  • cleaning compositions include but are not limited to laundry cleaning com positions and detergents, fabric softening compositions, fabric enhancing compositions, fabric freshening compositions, laundry prewash, laundry pretreat, laundry additives, spray products, dry cleaning agent or composition, laundry rinse additive, wash additive, post-rinse fabric treat ment, ironing aid, dish washing compositions, hard surface cleaning compositions, unit dose formulation, delayed delivery formulation, detergent contained on or in a porous substrate or nonwoven sheet, and other suitable forms that may be apparent to one skilled in the art in view of the teachings herein.
  • compositions may be used as a pre-laundering treatment, a post laundering treatment, or may be added during the rinse or wash cycle of the laundering opera tion.
  • the cleaning compositions may have a form selected from liquid, powder, single-phase or multi-phase unit dose, pouch, tablet, gel, paste, bar, or flake.
  • the cleaning composition is a hard surface cleaning composition.
  • the cleaning composition is a laundry detergent.
  • the cleaning composition is a liquid laundry detergent.
  • the cleaning composition comprises in the range of from 0.01 to 5.0 wt-% based on the total weight of the cleaning composition of at least one pol- yalkyleneimine derivate according to the present invention.
  • the clean ing composition comprises in the range of from 0.1 to 1.0 wt-% based on the total weight of the cleaning composition of at least one polyalkyleneimine derivate according to the present inven tion.
  • the amount of the polyalkyleneimine derivate according to the pre sent invention in the cleaning composition is more than 0.01 wt.-% and less than 0.5 wt.-% based on the weight of the total cleaning composition.
  • the cleaning compositions comprise a surfactant system in an amount sufficient to provide de sired cleaning properties.
  • the cleaning composition comprises, by weight of the composition, from about 1 % to about 70% of a surfactant system.
  • the liquid cleaning composition comprises, by weight of the composition, from about 2% to 190172
  • the cleaning composition comprising es, by weight of the composition, from about 5% to about 30% of the surfactant system.
  • the surfactant system may comprise a detersive surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, am- pholytic surfactants, and mixtures thereof.
  • a detersive surfactant encompasses any surfactant or mixture of surfactants that provide clean ing, stain removing, or laundering benefit to soiled material.
  • the cleaning compositions may also contain adjunct cleaning additives.
  • Suitable adjunct clean ing additives include builders, structurants or thickeners, clay soil removal/anti-redeposition agents, polymeric soil release agents, polymeric dispersing agents, polymeric grease cleaning agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaching agents, bleach activators, bleach catalysts, brighteners, dyes, hueing agents, dye transfer inhibiting agents, chelating agents, suds suppressors, softeners, and perfumes.
  • Hydroxyl values are measured according to DIN 53240-1.
  • Weight average molecular weight was measured by GPC Amine number was determined according to DIN 53176:2002-11.
  • the acid number was determined according to DIN 53402:1990-09.
  • PEI 800 consisting of 14 repeating units, contains statistically 4.6 primary, 4.6 sec ondary, and 4.6 tertiary amine functionalities

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne l'utilisation, dans une composition de nettoyage, d'un polymère comportant : a) un squelette polyalkylèneimine ; b) au moins une fraction aromatique P1 (P1), # indiquant le point de fixation à un atome d'azote du squelette polyalkylèneimine, Ar représentant indépendamment pour chaque fraction aromatique P1 un 1,2-phénylène, un 1,2-naphtylène, un 2,3-naphtylène ou un 1,8-naphtylène, le phénylène ou le naphtylène étant non substitué ou comportant 1, 2, 3, 4, ou 5 radicaux choisis dans le groupe constitué par un halogène, OH, C1-C4-alkyle, C1-C4-alcoxy, COOH, CONH2, NO2, NH2, NH-CHO, NH- C1-C4-alkyle, et NH-(C=O)-C1-C4-alkyle ; c) au moins une fraction P2 (P2), # indiquant le point de fixation à un atome d'azote du squelette polyalkylèneimine, n représentant un nombre entier compris entre 0 et 100, A1 étant choisi indépendamment parmi des alkylènes linéaires ou ramifiés dotés de 2 à 18 atomes de carbone, A2 pour chaque motif de répétition individuel n A2 étant choisi indépendamment parmi des alkylènes linéaires ou ramifiés dotés de 2 à 18 atomes de carbone.
PCT/EP2021/052950 2020-02-18 2021-02-08 Utilisation de dérivés de polyalkylèneimine dans des compositions de nettoyage WO2021165083A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20157881.2A EP3868853A1 (fr) 2020-02-18 2020-02-18 Utilisation de dérivés de polyalkylèneimine dans des compositions de nettoyage
EP20157881.2 2020-02-18

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WO2021165083A1 true WO2021165083A1 (fr) 2021-08-26

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CN116790178B (zh) * 2023-08-24 2023-11-03 广州恒峰新材料科技有限公司 一种防腐水性环氧树脂涂料及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130303424A1 (en) * 2012-05-11 2013-11-14 The Procter & Gamble Company Detergent composition
WO2017140538A1 (fr) 2016-02-16 2017-08-24 Basf Se Polymères à base de poly(iminoalkylène) ayant des groupes polyester
US20190177665A1 (en) * 2016-08-08 2019-06-13 Basf Se Liquid laundry formulation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130303424A1 (en) * 2012-05-11 2013-11-14 The Procter & Gamble Company Detergent composition
WO2017140538A1 (fr) 2016-02-16 2017-08-24 Basf Se Polymères à base de poly(iminoalkylène) ayant des groupes polyester
US20190092903A1 (en) * 2016-02-16 2019-03-28 Basf Se Polyalkylene imine based polymers having polyester groups
US20190177665A1 (en) * 2016-08-08 2019-06-13 Basf Se Liquid laundry formulation

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