EP1149081A1 - Colorants derives d'aryloxy-poly(oxyalkylene) naphtalimides - Google Patents

Colorants derives d'aryloxy-poly(oxyalkylene) naphtalimides

Info

Publication number
EP1149081A1
EP1149081A1 EP99973669A EP99973669A EP1149081A1 EP 1149081 A1 EP1149081 A1 EP 1149081A1 EP 99973669 A EP99973669 A EP 99973669A EP 99973669 A EP99973669 A EP 99973669A EP 1149081 A1 EP1149081 A1 EP 1149081A1
Authority
EP
European Patent Office
Prior art keywords
poly
colorant
oxyalkylene
colorants
aryloxy
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.)
Withdrawn
Application number
EP99973669A
Other languages
German (de)
English (en)
Other versions
EP1149081A4 (fr
Inventor
Robert L. Mahaffey, Jr.
James M. Spry
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.)
Milliken and Co
Original Assignee
Milliken and Co
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
Priority claimed from US09/243,056 external-priority patent/US5935272A/en
Priority claimed from US09/241,580 external-priority patent/US5998621A/en
Application filed by Milliken and Co filed Critical Milliken and Co
Publication of EP1149081A1 publication Critical patent/EP1149081A1/fr
Publication of EP1149081A4 publication Critical patent/EP1149081A4/fr
Withdrawn legal-status Critical Current

Links

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
    • C11D3/40—Dyes ; Pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes

Definitions

  • This invention relates to colorants comprising naphthalimide base groups with
  • naphthalimides are useful as fluorescent colorants, particularly within other liquid
  • aqueous media such as liquid detergents, and the like.
  • naphthalimide-based colorants including U.S. Patents Re. 35,370, to Henry, Re.
  • Lewis et al. 5,308,773, to Lewis et al., 5,357,782, to Henry, 5,420,136, to Lewis et
  • patentee's colorants all exist as solids at room temperature and thus
  • naphthalimide colorant compounds which comprise aryloxy-poly(oxyalkylene)
  • Liquid household compositions such as detergents, fabric softeners,
  • compositions have been commercialized in the past as well, the modern consumer
  • Such a colorant provides for very bright fluorescing colorations
  • colorants are solid in nature they must first be dispersed within liquid media through
  • non-water-soluble naphthalimide colorants exist as waxes or
  • compositions There is no teaching nor fair suggestion within the pertinent art which even alludes to a naphthalimide colorant which can be adapted for use in different
  • object of this invention to provide an aryloxy-poly(oxyalkylene)-derivative
  • the invention is to provide an aryloxy-poly(oxyalkylene) naphthalimide precursor to
  • Yet another object of this invention is to provide a relatively
  • compositions such as, for
  • a household composition i.e., liquid detergent, fabric softener, etc.
  • liquid detergent i.e., liquid detergent, fabric softener, etc.
  • aryloxypolyoxyalkylene naphthalimide derivative colorant to protect uranine
  • the present invention encompasses water-soluble naphthalimide derivative
  • ambient it is meant within a range of from about 20-25°C
  • subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the subject colorant may also be present but only in minimal amounts. Furthermore, the
  • inventive liquid compounds are readily soluble within myriad compositions, including
  • inventive compounds provide excellent fluorescing and coloring
  • colorant compounds can be utilized in applications where standard naphthalimide
  • inventive colorants can be utilized over a wide pH range and
  • fragrances and preservatives are compatible with fragrances and preservatives, as merely examples, without
  • the present invention also encompasses certain compositions comprising
  • compositions are water-based, the colorants of the inventive compositions will not
  • fluorescent colorants such as uranine, are not compatible within such low pH
  • compositions encompassed within this invention include, but are not limited
  • liquid household detergents and cleaners for laundry, dishwashing, light duty
  • compositions include both gel and liquid compositions. Such compositions require at least one
  • compositions comprise tensoactives and water. These compounds are present in order to improve the ability of the composition to clean or remove, soil, stains, and the like, and may
  • anionic surfactants cationic surfactants, amphoteric surfactants, zwitterionic
  • Possible cationic surfactants include quaternary ammonium salts, amines,
  • Suitable amphoterics include mixed C 8 amphocarboxylates,
  • betaine derivatives of quaternary ammonium, phosphonium, and sulfonium
  • duty liquids, tensoactives are present from about 0.01 to about 25% by weight of the
  • liquid detergents from about 0.1 to about 30% by weight; for
  • heavy duty detergents from about 2 to about 75% by weight, and so on.
  • perfumes such as smectite clays,
  • the primary constituent of the aforementioned cleaning compositions is water
  • propylene glycol monomethyl ether dipropylene glycol monomethyl ether, propylene
  • compositions of this invention may only comprise solvents other than
  • liquid cleaning compositions can be found in various United States
  • compositions all comprise well known fabric softening formulations and
  • composition of the present invention would include from about 3 to about 50%> by
  • cationic fabric softening compound preferably a quaternary ammonium compound.
  • the counterion may be a halide, such as fluoride, chloride, bromide, or iodide.
  • counterions may be employed such as methylsulfate, ethylsulfate, hydroxide, acetate,
  • the counterion is chloride or
  • compositions of the present invention Generally, concentrated liquid fabric softener
  • compositions of the present invention can contain 17%) to 50%> solids.
  • fabric softening compositions of the present invention can be prepared according to
  • cationic quaternary ammonium salts include, but are not limited
  • Acyclic quaternary ammonium salts having at least two C 8 - 30 ,
  • C I2 - 22 alkyl chains such as: ditallowdimethyl ammonium chloride
  • Diamido quaternary ammonium salts such as: methyl-
  • Biodegradable quaternary ammonium salts such as N,N-di(tallowoyl-
  • ammonium salts the pH of the composition is adjusted to between about 2 and 7,
  • Biodegradable cationic diester compounds may be employed of the type which have the
  • each R is a short chain C,. 6 , preferably C,. 3 , alkyl or hydroxyalkyl group, e.g.,
  • each R 2 is a long chain C 10 . 22 hydrocarbyl, or substituted hydrocarbyl
  • X " can be any softener-compatible anion, for example, chloride, bromide,
  • the fabric softening compositions of the present invention comprise a water
  • organic solvents such as lower alcohols, which can improve handling, fluidity, and viscosity. From 3 to about 50%>
  • the total composition comprises the active softening compounds
  • the fabric softeners are acyclic quaternary ammonium
  • compositions may be other non-cationic fabric conditioning
  • aminoethylethanolamine carboxylic acids having from 8 to 30 carbon atoms and one
  • esters of polyhydric alcohols such as sorbitan esters or glyceryl stearate, fatty alcohols, ethoxylated fatty alcohols, alkylphenols,
  • ethoxylated diglycerides ethoxylated diglycerides, ethoxylated fatty amines, mineral oils, and polyols, such as
  • inventive fabric softening composition to below about 7.0, preferably in the range
  • the inventive colorant is added in an amount from about 0.001 to about 3.0%
  • additives may be present in amounts from about 0.1 to about
  • These additives include silicones, predominantly polydimethylsiloxanes; soil
  • release polymers such as block copolymers of polyethylene oxide and terephthalate
  • surfactants and nonionic surfactants.
  • Such surfactants and soaps mirror those
  • polymer additives may be any suitable additives discussed above in the cleaning compositions. Additionally, polymer additives may be any suitable additives.
  • Electrolytes may be present, such as guar gum, polyethylene oxide, and cyclodextrin. Electrolytes may be present, such as guar gum, polyethylene oxide, and cyclodextrin. Electrolytes may be present, such as guar gum, polyethylene oxide, and cyclodextrin. Electrolytes may be present, such as guar gum, polyethylene oxide, and cyclodextrin. Electrolytes may
  • Such electrolytes include calcium chloride, magnesium chloride,
  • Preservatives such as glutaraldehyde and formaldehyde may also be added, as
  • Liquid fabric softening compositions encompassed within this invention can be any liquid fabric softening compositions encompassed within this invention.
  • a softening active premix is
  • the colorant can be any colorant, to which is added, with stirring, hot water.
  • the colorant can be any colorant.
  • the colorant is added to the hot water prior to addition to the premix.
  • colorants of invention are highly water soluble
  • inventive colorants may also be present in composition with a solvent.
  • propylene glycol monomethyl ether dipropylene glycol monomethyl ether, propylene
  • glycol o-benzyl-4-chlorophenol
  • deodorized kerosene odorless mineral spirits
  • pine oil n-methyl-pyrrolidone
  • wax n-methyl-pyrrolidone
  • wax n-methyl-pyrrolidone
  • d-limonene methylglycol
  • terpenes terpenes, and white spirits.
  • compositions of this invention may comprise non-aqueous solvents (with no
  • compositions include paint
  • solvent/colorant compositions may be merely utilized as colorant concentrates or
  • compositions such as fabric softener and/or cleaning compositions.
  • inventive colorant would be any colorant.
  • composition preferably from about 0.005 to about 1.0%>; more preferably from about
  • dispersant or dispersants
  • stabilizers including stabilizers, anti-corrosion agents, other surfactants, other dyes
  • naphthalic acid anhydride available from Aceto Corporation. The mixture was
  • a light duty liquid detergent was produced having the following typical
  • Such a composition included an amount of colorant sufficient to give a color depth
  • dimethylammonium chloride softener compound in an amount of about 0.017%) by
  • the resultant composition exhibited a bright yellow
  • Such a composition included an amount of colorant sufficient to give a color depth equal to a commercial sample containing uranine alone as the
  • composition was first analyzed for the initial maximum absorbance at the particularly
  • Test Method 16E Water-Cooled Xenon- Arc Lamp, Continuous Light.
  • COMPOSITION was placed in a sealed transparent plastic bottle and exposed to
  • compositions of EXAMPLE 4 was then also tested for their lightfastness
  • This commercial composition contains both uranine and D&C Yellow
  • compositions were subjected to the same accelerated
  • composition comprising uranine alone as well as the commercially available
  • inventive compositions are novel compositions.
  • the effective shelf-life of the inventive colored compositions are the inventive compositions.

Landscapes

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

Abstract

L'invention concerne des colorants contenant des groupes de base naphthalimides auxquels sont fixées des fractions pendantes spécifiques hydrosolubilisantes. Ces fractions pendantes sont basées sur des groupes aryloxy-poly(oxyalkylène) lesquels procurent la solubilité voulue au composé colorant naphtalimides, le terme aryloxy-poly(oxyalkylène) étant destiné à représenter la liaison directe du groupe aryle à l'azote de naphtalimides. De plus, les groupes aryloxy-poly(oxyalkylène) facilitent l'addition supplémentaire d'autres groupes pendants au composé de base lesquels augmentent ou diminuent également la solubilité du colorant dérivé de naphtalimides résultant. Ces naphtalimides modifiés sont utiles en tant que colorants fluorescents, en particulier dans d'autres milieux liquides (à la fois aqueux et non aqueux) sans l'addition nécessaire de tensioactifs, de solvants, de diluants et analogues. L'invention concerne également des procédés de production de ces colorants ainsi que les intermédiaires aryloxy-poly(oxyalkylène).
EP99973669A 1999-02-02 1999-11-17 Colorants derives d'aryloxy-poly(oxyalkylene) naphtalimides Withdrawn EP1149081A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US243056 1988-09-09
US09/243,056 US5935272A (en) 1999-02-02 1999-02-02 Compositions comprising aryloxypolyoxyalkylene naphthalimide derivative colorants
US09/241,580 US5998621A (en) 1999-02-02 1999-02-02 Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants
US241580 1999-02-02
PCT/US1999/026228 WO2000046205A1 (fr) 1999-02-02 1999-11-17 Colorants derives d'aryloxy-poly(oxyalkylene) naphtalimides

Publications (2)

Publication Number Publication Date
EP1149081A1 true EP1149081A1 (fr) 2001-10-31
EP1149081A4 EP1149081A4 (fr) 2002-05-29

Family

ID=26934415

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99973669A Withdrawn EP1149081A4 (fr) 1999-02-02 1999-11-17 Colorants derives d'aryloxy-poly(oxyalkylene) naphtalimides

Country Status (5)

Country Link
EP (1) EP1149081A4 (fr)
JP (1) JP3993747B2 (fr)
KR (1) KR100582321B1 (fr)
AU (1) AU1470300A (fr)
WO (1) WO2000046205A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE20216573U1 (de) * 2002-10-27 2004-03-04 Dalli-Werke Wäsche- und Körperpflege GmbH & Co. KG Portion eines gefärbten, nicht festen Waschmittels
CN104411740B (zh) * 2012-05-02 2017-07-11 路博润高级材料公司 芳族分散剂组合物
CN104411739B (zh) * 2012-05-02 2017-03-08 路博润高级材料公司 芳族分散剂组合物
US10113031B2 (en) * 2013-11-01 2018-10-30 Lubrizol Advanced Materials, Inc. Aromatic dispersant composition
CN106471112A (zh) * 2014-05-06 2017-03-01 美利肯公司 衣物洗涤护理组合物
CN106187892B (zh) * 2016-07-13 2019-03-15 电子科技大学 一种有机掺杂型双功能器件及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4992204A (en) * 1989-08-22 1991-02-12 Miliken Research Corporation Irradiation detection and identification method and compositions useful therein
EP0527649A2 (fr) * 1991-08-13 1993-02-17 Milliken Research Corporation Colorant de type xanthène substitué par un groupement polyoxyalkylène et procédé pour sa préparation
US5565551A (en) * 1992-03-19 1996-10-15 Microbiomed Corporation Non-azo naphthalimide dyes and uses for same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4832177B1 (fr) * 1970-04-06 1973-10-04
CS193650B1 (en) * 1978-06-30 1979-11-30 Josef Dolezal Brilliant yellow dispersive dyes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4992204A (en) * 1989-08-22 1991-02-12 Miliken Research Corporation Irradiation detection and identification method and compositions useful therein
EP0527649A2 (fr) * 1991-08-13 1993-02-17 Milliken Research Corporation Colorant de type xanthène substitué par un groupement polyoxyalkylène et procédé pour sa préparation
US5565551A (en) * 1992-03-19 1996-10-15 Microbiomed Corporation Non-azo naphthalimide dyes and uses for same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0046205A1 *

Also Published As

Publication number Publication date
JP2002536464A (ja) 2002-10-29
JP3993747B2 (ja) 2007-10-17
AU1470300A (en) 2000-08-25
EP1149081A4 (fr) 2002-05-29
WO2000046205A1 (fr) 2000-08-10
KR100582321B1 (ko) 2006-05-22
KR20010101949A (ko) 2001-11-15

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