WO2000046205A1 - Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants - Google Patents
Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants Download PDFInfo
- Publication number
- WO2000046205A1 WO2000046205A1 PCT/US1999/026228 US9926228W WO0046205A1 WO 2000046205 A1 WO2000046205 A1 WO 2000046205A1 US 9926228 W US9926228 W US 9926228W WO 0046205 A1 WO0046205 A1 WO 0046205A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- poly
- colorant
- oxyalkylene
- colorants
- aryloxy
- Prior art date
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
- aryloxy-poly(oxyalkylene) groups facilitate the further addition of
- naphthalimides are useful as fluorescent colorants, particularly within other liquid
- aryloxy-poly(oxyalkylene) intermediates are also contemplated within this invention.
- standard naphthalimide colorants exist as waxes or oily solids, which are
- 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
- inventive compounds provide excellent fluorescing and coloring characteristics within such media, and are particularly effective when combined with other colorants, dyes,
- naphthalimide colorant compounds can be utilized in applications where standard
- naphthalimide dyes were inoperable in the past.
- inventive colorants can be
- colorants are also compatible with most cationic, anionic, non-ionic, and quaternary
- fluorescent colorants such as uranine, are not compatible within such low pH
- uranine in certain compositions has provided an effective manner of prolonging the
- plastic containers For instance, if a composition is colored fluorescent green,
- this mixture will fade and degrade into a blue colored
- poly(oxyalkylene) naphthalimide derivative colorants exhibit excellent lightfastness
- Uranine itself exhibits excellent and desirable
- the uranine appears to be protected from degradation of its fluorescent characteristics.
- inventive naphthalimide colorants exhibit absorbencies over a range of wavelengths
- naphthalimide seemingly protects the uranine from over exposure to light in those
- this invention includes a colorant compound as defined by the
- R is aryloxy-poly(oxyalkylene); R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen, lower alkyl, lower hydroxyalkyl, and polyoxyalkylene; and X is hydrogen, SO " 3 , and NO 2 .
- this invention encompasses an intermediate of this compound which includes a compound defined by the F
- R is aryloxy-poly(oxyalkylene), wherein the aryl group is directly bonded to the nitrogen;
- R 1 is selected from the group consisting of chloro and bromo groups;
- X is selected from the group consisting of hydrogen, SO " 3 , and NO 2 .
- the particular oxyalkylene groups are selected from ethyleneoxy (EO), propyleneoxy (PO), and butyleneoxy (BO) groups.
- these moieties are all EO groups, although combinations of EO and any of the others may be utilized as well.
- polyoxyalkylene is intended
- compositions comprising such a colorant are also encompassed within this invention.
- moieties such as oxyalkylamines, alkylamines, cyclic groups, such as morpholine,
- hydrochloric acid scavenger such as sodium carbonate or excess amine
- the colorant compound (I) is liquid in nature at
- colorant additives such as resins, preservatives, surfactants, solvents, antistatic agents
- compositions or methods are provided.
- compositions encompassed within this invention include, but are not limited
- liquid household detergents and cleaners for laundry, dishwashing, light duty
- compositions for floor cleaners, and the like), fabric softeners, paint strippers, wax
- compositions include both gel and liquid compositions. Such compositions require at least one
- Liquid detergents Liquid detergents, light duty cleaning liquids, heavy duty cleaning liquids,
- 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
- Suitable tensoactives include nonionic surfactants,
- anionic surfactants cationic surfactants, amphoteric surfactants, zwitterionic
- nonionic surfactants are included
- alkyl phenols such as diethanolamides, amine oxides, phosphine
- Anionic surfactants include linear or branched
- fatty ether sulfates ammonium ethoxysulfate, sodium ethoxysulfate, phosphate esters,
- Possible cationic surfactants include quaternary ammonium salts, amines,
- Suitable amphoterics include mixed C 8 amphocarboxylates,
- Suitable zwitterionics include betaines, such as cocamidopropyl
- betaine derivatives of quaternary ammonium, phosphonium, and sulfonium
- Soaps include any saponified fatty acids made from oils and fats (such as
- Tensoactives will generally be present in proportions depending primarily on
- 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.
- optical brighteners abrasives, suds boosters, suds depressors, soil suspending/release
- perfumes such as smectite clays,
- colorants such as reactive, acid, solvent, and the like dyes.
- the primary constituent of the aforementioned cleaning compositions is water
- non-aqueous solvents may also be used, including lower alcohols
- propylene glycol monomethyl ether dipropylene glycol monomethyl ether, propylene
- compositions of this invention may only comprise solvents other than
- compositions comprise anywhere from 1 to 99% by weight of
- the total composition water preferably from about 20 to about 80%> water, and most
- Solvents may comprise from 0 to about 40%> by weight of the total composition
- composition preferably from about 0.1 to about 20%>.
- inventive colorant is added
- 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-
- ammonium methylsulfate (Varisoft 238® from Sherex), and the like;
- 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
- substituent preferably C 15 . I9 alkyl and/or alkylene, most preferably C, 5 . 17 straight chain
- 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.
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- 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
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU14703/00A AU1470300A (en) | 1999-02-02 | 1999-11-17 | Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants |
JP2000597275A JP3993747B2 (en) | 1999-02-02 | 1999-11-17 | Aryloxy-poly (oxyalkylene) naphthalimide derivative colorant |
EP99973669A EP1149081A4 (en) | 1999-02-02 | 1999-11-17 | Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/243,056 US5935272A (en) | 1999-02-02 | 1999-02-02 | Compositions comprising aryloxypolyoxyalkylene naphthalimide derivative colorants |
US09/243,056 | 1999-02-02 | ||
US09/241,580 | 1999-02-02 | ||
US09/241,580 US5998621A (en) | 1999-02-02 | 1999-02-02 | Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000046205A1 true WO2000046205A1 (en) | 2000-08-10 |
Family
ID=26934415
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/026228 WO2000046205A1 (en) | 1999-02-02 | 1999-11-17 | Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1149081A4 (en) |
JP (1) | JP3993747B2 (en) |
KR (1) | KR100582321B1 (en) |
AU (1) | AU1470300A (en) |
WO (1) | WO2000046205A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2394476A (en) * | 2002-10-27 | 2004-04-28 | Dalli Werke Waesche & Koerperp | Portion of a coloured, non-solid detergent |
CN106187892A (en) * | 2016-07-13 | 2016-12-07 | 电子科技大学 | A kind of organic blended type double-function device and preparation method thereof |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104411740B (en) * | 2012-05-02 | 2017-07-11 | 路博润高级材料公司 | Aromatics dispersant composition |
CN104411739B (en) * | 2012-05-02 | 2017-03-08 | 路博润高级材料公司 | Aromatics dispersant composition |
US10113031B2 (en) * | 2013-11-01 | 2018-10-30 | Lubrizol Advanced Materials, Inc. | Aromatic dispersant composition |
CN106471112A (en) * | 2014-05-06 | 2017-03-01 | 美利肯公司 | Laundry care composition |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4832177B1 (en) * | 1970-04-06 | 1973-10-04 | ||
CS193650B1 (en) * | 1978-06-30 | 1979-11-30 | Josef Dolezal | Brilliant yellow dispersive dyes |
US5565551A (en) * | 1992-03-19 | 1996-10-15 | Microbiomed Corporation | Non-azo naphthalimide dyes and uses for same |
Family Cites Families (2)
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 |
US5331097A (en) * | 1991-08-13 | 1994-07-19 | Milliken Research Corporation | Poly(oxyalkylene) substituted xanthene colorant and method for making the same |
-
1999
- 1999-11-17 EP EP99973669A patent/EP1149081A4/en not_active Withdrawn
- 1999-11-17 KR KR1020017009770A patent/KR100582321B1/en active IP Right Grant
- 1999-11-17 JP JP2000597275A patent/JP3993747B2/en not_active Expired - Lifetime
- 1999-11-17 WO PCT/US1999/026228 patent/WO2000046205A1/en active IP Right Grant
- 1999-11-17 AU AU14703/00A patent/AU1470300A/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4832177B1 (en) * | 1970-04-06 | 1973-10-04 | ||
CS193650B1 (en) * | 1978-06-30 | 1979-11-30 | Josef Dolezal | Brilliant yellow dispersive dyes |
US5565551A (en) * | 1992-03-19 | 1996-10-15 | Microbiomed Corporation | Non-azo naphthalimide dyes and uses for same |
Non-Patent Citations (1)
Title |
---|
See also references of EP1149081A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2394476A (en) * | 2002-10-27 | 2004-04-28 | Dalli Werke Waesche & Koerperp | Portion of a coloured, non-solid detergent |
CN106187892A (en) * | 2016-07-13 | 2016-12-07 | 电子科技大学 | A kind of organic blended type double-function device and preparation method thereof |
CN106187892B (en) * | 2016-07-13 | 2019-03-15 | 电子科技大学 | A kind of organic blended type double-function device and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
EP1149081A1 (en) | 2001-10-31 |
JP2002536464A (en) | 2002-10-29 |
JP3993747B2 (en) | 2007-10-17 |
AU1470300A (en) | 2000-08-25 |
EP1149081A4 (en) | 2002-05-29 |
KR100582321B1 (en) | 2006-05-22 |
KR20010101949A (en) | 2001-11-15 |
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