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Patent US4518435 - Dispersing agent for solids in polar organic liquids - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Advanced Patent Search | Sign inAdvanced Patent SearchPatentsA dispersing agent comprising the salt of a tertiary amine containing at least one poly(lower alkyleneoxy) chain and an aromatic acid having at least two benzene rings and a dispersion of an organic pigment, an organic dyestuff or carbon black in a polar organic solvent containing said dispersing agent...http://www.google.com/patents/US4518435?utm_source=gb-gplus-sharePatent US4518435 - Dispersing agent for solids in polar organic liquidsPublication numberUS4518435 APublication typeGrantApplication numberUS 06/459,036Publication dateMay 21, 1985Filing dateJan 18, 1983Priority dateFeb 21, 1977Fee statusPaidAlso published asCA1107878A1, DE2807362A1, DE2807362C2, US4398955Publication number06459036, 459036, US 4518435 A, US 4518435A, US-A-4518435, US4518435 A, US4518435AInventorsJames F. Stansfield, James Toole, Arthur TophamOriginal AssigneeImperial Chemical Industries LimitedExport CitationBiBTeX, EndNote, RefManPatent Citations (13), Non-Patent Citations (1), Referenced by (13), Classifications (27), Legal Events (6) External Links: USPTO, USPTO Assignment, EspacenetDispersing agent for solids in polar organic liquidsUS 4518435 AAbstract A dispersing agent comprising the salt of a tertiary amine containing at least one poly(lower alkyleneoxy) chain and an aromatic acid having at least two benzene rings and a dispersion of an organic pigment, an organic dyestuff or carbon black in a polar organic solvent containing said dispersing agent is disclosed.
We claim: 1. A dispersion of from 10% to 80% by weight, based on the total weight of the dispersion, of a particulate solid selected from organic pigments, organic disperse dyestuffs and carbon black in a polar organic liquid selected from ethers, esters, ketones, glycols, alcohols and amides, said dispersion containing from 2% to 50% by weight, based on the weight of the particulate solid, of a salt of an amine of the formula: ##STR7## wherein each of A, B and D independently represents alkyl, -YH or ##STR8## wherein each X independently represents an oxygen or a nitrogen atom provided that,where X is oxygen, m+n=1 and p=1, andwhere X is nitrogen, m+n=2 and p is from 1 to 30; each Q independently represents alkyl or --YH; and each Y independently represents a poly(lower alkylene oxy) chain containing from 3 to 50 lower alkylene oxy groups, provided that(i) at least one of A, B and D contains a poly(lower alkylene oxy) chain, (ii) at least 50% of the lower alkylene groups in each poly(lower alkylene oxy) chain are propylene, and (iii) not more than one of the alkylene or alkyl groups contains more than 8 carbon atoms,with an aromatic acid having at least two benzene rings selected from an organic pigment containing one or more acid groups and an organic dyestuff containing one or more acid groups. 2. A dispersion according to claim 1 in which the aromatic acid contains from 2 to 12 benzene rings.
10. A salt of an amine of the formula: ##STR10## wherein each of A, B and D independently represents alkyl, -YH or ##STR11## wherein each X independently represents an oxygen or a nitrogen atom provided that,where X is oxygen, m+n=1 and p=1, andwhere X is nitrogen, m+n=2 and p is from 1 to 30; each Q independently represents alkyl or --YH; and each Y independently represents a poly(lower alkylene oxy) chain containing from 3 to 50 lower alkylene oxy groups provided that,(i) at least one of A, B and D contains a poly(lower alkylene oxy) chain, (ii) at least 50% of the lower alkylene groups in each poly(lower alkylene oxy) chain are propylene, and (iii) not more than one of the alkylene or alkyl groups contains more than 8 carbon atoms,with an aromatic acid having at least two benzene rings selected from an organic pigment containing one or more acid groups and an organic dyestuff containing one or more acid groups. Description
EXAMPLE 1 A mixture of 0.53 parts of Agent B, 0.37 part of a copper phthalocyanine sulphonic acid of average degree of sulphonation 1.3 (CPC(SO.sub.3).sub.n wherein n=1.3) and 6.1 parts of ethanol is ball milled for 2 hours to form the salt, then 3 parts of β-form copper phthalocyanine is added and milling continued for a further 16 hours, to give a fluid dispersion of the pigment which is suitable for use in a printing ink, e.g. for gravure or flexographic printing.
__________________________________________________________________________   Pigment and       Agent and Polycyclic Aromatic                              OrganicEx.   amount thereof       amount thereof                 acid and amount thereof                              liquid__________________________________________________________________________2  3 parts of       0.38 part of                 0.52 part of CPC                              ethanol   &#946;-form CPC       Agent A   (SO.sub.3 H).sub.1.33  3 parts of       0.51 part of                 0.31 part of "   &#946;-form CPC       Agent B   CPC monosulphonic acid4  3 parts of       0.54 part of                 0.36 part of "   &#946;-form CPC       Agent C   CPC (SO.sub.3 H).sub.1.35  3 parts of       0.71 part of                 0.19 part of "   &#946;-form CPC       Agent D   CPC (SO.sub.3 H).sub.1.36  3 parts of       0.59 part of                 0.31 part of "   &#946;-form CPC       Agent E   CPC (SO.sub.3 H).sub.1.37  3 parts of       0.42 part of                 0.18 part of "   &#946;-form CPC       Agent B   CPC (SO.sub.3 H).sub.1.38  3 part of       0.53 part of                 0.37 part of "   polychloro       Agent B   CPC (SO.sub.3 H).sub.1.3   CPC9  3 parts of       0.53 part of                 0.37 part of "   carbon black       Agent B   CPC (SO.sub.3 H).sub.1.310 3 parts of       0.53 part of                 0.37 part of "   indanthrone       Agent B   CPC (SO.sub.3 H).sub.1.311 3 parts of       0.53 part of                 0.37 part of "   &#945;-form       Agent B   CPC (SO.sub.3 H).sub.1.3   partially   chlorinated CPC12 3 parts  0.53 part of                 0.37 part of isopropanol   &#946;-form CPC       Agent B   CPC (SO.sub.3 H.sub.1.313 3 parts  0.6 part of                 0.3 part of  "   &#946;-form CPC       Propomeen HT/25                 CPC (SO.sub.3 H).sub.1.314 3 parts  0.58 part of                 0.32 part of methylethyl-   &#946;-form CPC       Agent F   CPC (SO.sub.3 H).sub.1.3                              ketone15 3 parts  0.7 part of                 0.2 part of  methylethyl-   &#946;-form CPC       Agent G   CPC (SO.sub.3 H).sub.1.3                              ketone16 3 parts  0.7 part of                 0.2 part of  ethyl acetate   &#946;-form CPC       Agent G   CPC (SO.sub.3 H(.sub.1.317 3 parts  0.53 part of                 0.37 part of butanol   &#946;-from CPC       Agent B   CPC SO.sub.3 H).sub.1.318 3 parts of       0.9 part of                 Nil          ethanol   Prussian Blue       Agent A19 3 parts of       0.1 part of                 "            "   Prussian Blue       Agent B20 3 parts of       0.5 part of                 "            "   Prussian Blue       Propomeen HT/2521 7 parts of       0.35 part of                 "            "   lead sulpho-       Agent B   chromate22 5 parts of       0.5 part of                 "            "   chromium Agent B   oxide23 5 parts of       0.5 part of                 "            "   titanium Agent B   dioxide24 7 parts of       0.7 part of                 "            "   iron oxide       Agent B25 5 parts of       0.5 part of                 "            isopropanol   Prussian Blue       Propomeen HT/2526 5 parts of       0.5 part of the                 "            ethanol   Prussian Blue       hydrochloride of       Agent B27 5 parts of       0.5 part of the                 "            "   Prussian Blue       sulphate of       Agent B28 5 parts of       0.5 part of the                 "            "   Prussian Blue       acetate of       Agent B29 5 parts of       0.5 part of the                 "            "   Prussian Blue       benzoate of       Agent B30 5 parts of       0.5 part of the                 "            "   Prussian Blue       p-toluene sulphonate       of Agent B31 3 parts of       0.61 part of                 0.29 part of "   &#946;-form CPC       Agent H   CPC (SO.sub.3 H).sub.1.332 3 parts of       0.53 part of                 0.37 part of "   &#946;-form CPC       Agent I   CPC (SO.sub.3 H).sub.1.333 3 parts of       0.7 parts of                 0.2 part of  "   Carbon Black       Agent J   Acid A34 3 parts of       0.65 part of                 0.26 part of "   Carbon Black       Agent J   Acid B35 3 parts of       0.78 part of                 0.12 part of "   Carbon Black       Agent J   Acid C36 3 parts of       0.71 part of                 0.19 part of "   Carbon Black       Agent J   Acid D37 3 parts of       0.78 part of                 0.19 part of "   polychlorinated       Agent J   Acid E   CPC__________________________________________________________________________
EXAMPLE 38 20 parts of β-copper phthalocyanine is mixed with 80 parts of a varnish medium consisting of 15 parts of nitrocellulose, 17 parts of isopropyl acetate, 58 parts of ethanol 74 OP, 4.8 parts of Agent B and 3.2 parts of CPC(SO.sub.3 H).sub.1.3. The mixture is milled for 18 hours in a Ball Mill before dilution with 100 parts of a varnish medium comprising 15 parts nitrocellulose, 17 parts isopropyl acetate and 68 parts of ethanol 740OP. This mill base is suitable for mixing with further solvent, varnish or other conventional additives for use in printing inks or other surface coating compositions.
Preferred amines of the general formula: ##STR4## are: alkyl-N--(YH).sub.2,
alkyl N--(alkylene-O-YH).sub.2,
N--(alkylene-O--YH).sub.3,
and especially (alkyl).sub.2 --N--alkylene--O--YH,
(CH.sub.3 CH.sub.2).sub.2 NCH.sub.2 CH.sub.2 O(CH.sub.2.CH(CH.sub.3)O).sub.4 H,
(CH.sub.3 CH.sub.2).sub.2 NCH.sub.2 CH.sub.2 O(CH.sub.2 --CH(CH.sub.3)O).sub.12 H,
(CH.sub.3).sub.2 NCH.sub.2 CH.sub.2 O[CH.sub.2 -CH(CH.sub.3)O].sub.17 H,
N[CH.sub.2 CH.sub.2 O(CH.sub.2 -CH(CH.sub.3)O).sub.12 H].sub.3, ##STR5## wherein a+b=15 N-[CH.sub.2 CH.sub.2 O(CH.sub.2 CH(CH.sub.3)O).sub.4 H].sub.3, and
(CH.sub.3 CH.sub.2).sub.2 N-CH.sub.2 CH.sub.2 O(CH.sub.2 CH.sub.2 O).sub.10 (CH.sub.2 CH(CH.sub.3)O).sub.20 H.
Agent A 8 Parts of potassium are dissolved in 450 parts of 2-diethylaminoethanol and propylene oxide is added at 105 until the equivalent by titration with acid reaches 420.
Agent F A mixture of 71.3 parts of E-caprolactone, 8.1 parts of 3-dimethylaminopropylamine and 0.1 part of tetrabutyl titanate is stirred for 11/2 hours at 160 forms a hard wax of equivalent 1016.
Agent I 30 Parts of polyethyleneimine of molecular weight 1200 (sold as PEI-12 by Dow Corp.) is stirred at 40 propylene oxide is gradually added during 11 hours. After removing unchanged propylene oxide at 100 parts. A solution of 1.55 parts of potassium hydroxide in 2.65 parts of water is added and the water removed at 100 is stirred at 100 oxide is added during 30 hours. After removing unchanged propylene oxide at 100/18 mm the yield is 275 parts of pale amber coloured viscous liquid.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS2490703 *May 1, 1946Dec 6, 1949Gen Aniline & Film CorpSalts of organic dyestuffsUS2490704 *May 1, 1946Dec 6, 1949Gen Aniline & Film CorpReaction product of sulfonated copper phthalocyanine with an alkanolamineUS3841888 *Nov 3, 1972Oct 15, 1974Basf AgAqueous pigment dispersionsUS3917639 *Jan 14, 1974Nov 4, 1975Ici LtdDispersing agentsUS3928276 *Jan 29, 1973Dec 23, 1975Henkel & Cie GmbhSalts of amine-alkylene oxide adducts for preventing sedimentation of pigment suspensionsUS4101690 *Nov 26, 1974Jul 18, 1978Fuji Photo Film Co., Ltd.Desensitizing compositionUS4198203 *Apr 28, 1978Apr 15, 1980Bayer AktiengesellschaftDyestuff solutions of copper phthalocyanine derivatives for paper dyeingUS4239549 *Jul 15, 1977Dec 16, 1980Basf AktiengesellschaftEasily water-dispersed formulations of finely divided phthalocyaninesUS4282000 *Jan 25, 1980Aug 4, 1981Bayer AktiengesellschaftDyestuff solutions, their preparation and their use for dyeing paperUS4398955 *Jun 23, 1981Aug 16, 1983Imperial Chemical Industries PlcDispersionsDE2807362A1 *Feb 21, 1978Aug 24, 1978Ici LtdDispersion eines teilchenfoermigen feststoffs in einem polaren organischen mediumGB1164265A * Title not availableGB1596281A * Title not available* Cited by examinerNon-Patent CitationsReference1 *Morrison, R. T. et al., Organic Chemistry, pub. 1966, by Allyn and Bacon, Boston, Mass., p. 1101, (Amino Acids as Dipolar Ions . . . Thyroxine).* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS4645611 *Feb 1, 1985Feb 24, 1987Imperial Chemical Industries PlcDispersionUS4698099 *Jan 23, 1986Oct 6, 1987Dainichiseika Color & Chemicals Mfg. Co., Ltd.Pigment compositionUS4861380 *Oct 27, 1988Aug 29, 1989Imperial Chemical Industries PlcCompositionUS5395743 *Dec 22, 1993Mar 7, 1995Eastman Kodak CompanyPhotographic element having a transparent magnetic layer and a process of preparing the sameUS5885338 *Oct 18, 1996Mar 23, 1999Sri InternationalWater-based, water-fast ink compositions containing two-component binder matrix from nitrogen polymerUS5968244 *Feb 17, 1998Oct 19, 1999Minolta Co., Ltd.Ink for ink-jet recordingUS6471764Nov 16, 2000Oct 29, 2002Sun Chemical CorporationTreatment of high performance pigments with etheramine dispersing saltsUS6540825Jun 21, 1995Apr 1, 2003The Lubrizol CorporationCompositions utilizing dispersantsUS6926768Apr 14, 2003Aug 9, 2005Sun Chemical CorporationTreatment of high performance pigmentsUS20130212934 *Dec 24, 2010Aug 22, 2013Alex John CantlayLiquid fuel compositionsEP0398620A2 *May 15, 1990Nov 22, 1990Milliken Research CorporationPoly(oxyalkylene) modified phthalocyanine colorantsWO2011076948A1Dec 24, 2010Jun 30, 2011Shell Internationale Research Maatschappij B.V.Liquid fuel compositionsWO2011076949A1Dec 24, 2010Jun 30, 2011Shell Internationale Research Maatschappij B.V.Liquid fuel compositions* Cited by examinerClassifications U.S. Classification106/413, 106/31.46, 534/880, 106/493, 534/783, 106/31.75, 106/31.43, 534/827, 106/499, 534/654, 106/503, 540/132International ClassificationB01F17/00, B01F17/04, C09B67/00, C09D7/12, B01F17/16, B01F17/42, B01F17/46, C09D17/00, C09D7/00Cooperative ClassificationC09D17/004, B01F17/005, B01F17/0057European ClassificationB01F17/00K2, B01F17/00M, C09D17/00JLegal EventsDateCodeEventDescriptionSep 24, 1996FPAYFee paymentYear of fee payment: 12Apr 29, 1994ASAssignmentOwner name: ZENECA LIMITED, ENGLANDFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:IMPERIAL CHEMICAL INDUSTRIES PLC;REEL/FRAME:006965/0039Effective date: 19931102Oct 14, 1992FPAYFee paymentYear of fee payment: 8Oct 17, 1988FPAYFee paymentYear of fee payment: 4Jan 18, 1983AS02Assignment of assignor's interestOwner name: IMPERIAL CHEMICAL INDUSTRIES LIMITEDEffective date: 19830105Owner name: MILLBANK, LONDON, S.W.1, ENGLAND A CORP OOwner name: STANSFIELD, JAMES F.Owner name: TOOLE, JAMESEffective date: 19830106Owner name: TOPHAM, ARTHURJan 18, 1983ASAssignmentOwner name: IMPERIAL CHEMICAL INDUSTRIES LIMITED; MILLBANK, LOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:STANSFIELD, JAMES F.;TOOLE, JAMES;TOPHAM, ARTHUR;REEL/FRAME:004086/0809;SIGNING DATES FROM 19830105 TO 19830106RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services©2012 Google