Milliken Research Corporation

Research, Incorporated

Edward W. Kluger

John W. Rekers

David J. Moody

Max a. Weaver

John W Rekers

Edward W Kluger

David J Moody

John W Miley

R Marshall Wilson

Max Allen Weaver

Todd D Danielson

Gerald Scott

William C Kimbrell, Jr

Judy A Wagner

The present invention provides primary hydroxyl enhanced colorants having markedly improved reactivities in e.g., polyurethane foams for imparting permanent coloring thereto, the colorants having the formula

Intermediates and colorants having primary hydroxyl enriched poly

A colorant for natural or synthetic resinous or polymeric materials, having the formula A--[SO.sub.2 --N(R.sub.2)--Y].sub.1-4 ; wherein: R.sub.2 is selected for example from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl. alkoxy, alkylthio, or aryloxy; Y is a poly(oxyalkylene) moiety containing at least three monomeric units or mixtures thereof of the formula (--RO--) wherein each R is straight or branched alkylene of 1-4 carbons or mixtures thereof, up to about 20 mole percent of said monomeric units may be connected by one or more linking groups such as alkyleneoxy, --NH--, or --NHCONH--, and wherein Y can be terminated by hydrogen, or by at branch substituents, containing 1--3 groups or moieties selected from alkyl, cycloalkyl, acyl, or aryl; wherein any of the above recited hydrocarbon groups, moieties or substitutents may themselves be substituted with up to four substitutents selected, for example, from alkyl, halogen, mercapto, alkoxycarbonyl, hydroxy, alkoxy, or the like; and wherein each aliphatic hydrocarbon portion or moiety of the groups, moieties or substituents recited above contains from 1-20 carbons.

Poly(oxyalkylene) modified phthalocyanine colorants

An opacified, semi-crystalline thermoplastic resin composition is provided having a poly(alkyleneoxy) substituted organic chromophore distributed throughout in an amount sufficient to color the resin. The resin composition is particularly useful for molding parts with strict dimensional tolerances as shrinkage of the molded part is minimal.

Colorants for use in opacified thermoplastic resins

A colorant for natural or synthetic resinous or polymeric materials, having the formula A--[SO.sub.2 --N(R.sub.2)--Y].sub.1-4 ; wherein: R.sub.2 is selected for example from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl, alkoxy, alkylthio, or aryloxy; Y is a poly(oxyalkylene) moiety containing at least three monomeric units or mixtures thereof of the formula (--RO--) wherein each R is straight or branched alkylene of 2-4 carbons or mixtures thereof, up to about 20 mole percent of said monomeric units may be connected by one or more linking groups such as alkyleneoxy, --NH--, or --NHCONH--, and wherein Y can be terminated by hydrogen, or by at branch subsituents, containing 1-3 groups or moieties selected from alkyl, cycloalkyl, acyl, or aryl; wherein any of the above recited hydrocarbon groups, moieties or substituents may themselves be substituted with up to four substituents selected, for example, from alkyl, halogen, mercapto, alkoxycarbonyl, hydroxy, alkoxy, or the like; and wherein each aliphatic hydrocarbon portion or moiety of the groups, moieties or substituents recited above contains from 1-20 carbons.

Bis(3,4-dialkylbenzylidene) sorbitol acetals are provided for the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently selected from lower alkyl groups containing 1-4 carbon atoms.

Bis(3,4-dialkylbenzylidene) sorbitol acetals and compositions containing

Colorants and compositions containing the same, including polymeric substrates, especially polyurethane foams which are tinted or deeper colored with the colorants which have the general formula: ##STR1## wherein R.sub.2 is selected from hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted or unsubstituted; Z is an arylene moiety; each D or D' is selected from a covalent bond or a linking group consisting of or containing at least one of --O--, --S--, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloaliphatic or aryl, and R.sub.3 is R.sub.4 or hydrogen; D in combination with Z can also be a covalent bond; Y is a poly(oxyalkylene) moiety containing at least about 50 mole percent of monomeric units or mixture thereof of the formula (--RO--) wherein each R is substituted or unsubstituted straight or branched alkylene of 1-4 carbons or mixtures thereof; wherein ring P can be unsubstituted or substituted in addition to the --(D'--Y) moieties; and wherein each aliphatic hydrocarbon portion or moiety of the groups, moieties or substituents recited above contain from 1-20 carbons and wherein n is 1- 16, except when --D--Z-- is a covalent bond then n is equal to 1-4.

Bis(3,4-dialkylbenzylidene) sorbitol acetals are provided for the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently selected from lower alkyl groups containing 1-4 carbon atoms, or together form a carbocyclic ring containing up to 5 carbon atoms.

A substituted colorant which may be copolymerized with a condensation polymer to provide a covalently bound, nonextractable coloring, having the formula ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or lower alkyl; R.sub.4 is selected from hydrogen or lower alkyl; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N and M is from 3 to about 100. The hydroxyl groups are protected by formation of a ring structure during alkoxylation and amination of the substituent.

Polyoxylalkylene amino diol substituted colorants

A washable ink composition is provided which is an aqueous mixture containing water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR1## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R.sub.1 is H or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR2## wherein: R.sub.3 is H or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R.sub.2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80; and Z is a divalent vinylic carbon atom which is covalently bonded to a group or moiety including any of cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.

Methine colorants and washable ink compositions containing methine

A thermoplastic resin composition is provided which contains a thermoplastic resin and a colorant in the form of a polyalkyleneoxy-trifluoromethyl aniline colorant provided in said thermoplastic resin in a minor amount sufficient to provide coloration to said resin, said colorant having the formula: ##STR1## wherein R.sub.1 is selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 OH, phenyl or ##STR2## wherein R.sub.4 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is H, CF.sub.3, a lower alkyl group containing from 1 to about 9 carbon atoms, Cl or Br; R.sub.3 is an aromatic or heteroaromatic containing group, and n is an integer from 2 to about 75.

Thermoplastic resin composition containing polyalkyleneoxy-substituted

Primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane compounds are provided of the formula: ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or a lower alkyl group; R.sub.2 and R.sub.3 are independently selected from hydrogen, phenyl or lower alkyl groups; R.sub.4 is selected from hydrogen or a lower alkyl group; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N an M is from 2 to about 100; also disclosed are polyoxyalkylene amino alcohol compounds which may be derived from the compounds of Formula I above having the formula: ##STR2## wherein R, R.sub.1, R.sub.4, x, N and M all have the values given above. Also provided is a process for preparing a primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane.

Polyoxyalkylene amino alcohols and polyoxyalkylene amino 1,3-dioxanes

A process for coloring polyurethane resins made by a polyaddition reaction of a polyol and an isocyanate is provided, which comprises adding to the reaction mixture before or during the polyaddition reaction a reactive coloring agent suitable for incorporation in the resin with the formation of covalent bonds, said coloring agent having the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently selected from an alkyl group having from 1 to about 12 carbon atoms, X is --CH.sub.2 --, a and a' are integers from 1 to about 6, and Y and Y' are independently selected from polymeric units of hydroxy alkylenes or alkylene oxide monomers selected from ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide, or glycidol, b and b' are independently either 0 or 1, and Z and Z' are reactive groups independently selected from --OH, --NH.sub.2, or --SH.

Process for preparing polyurethane resins colored with anthraquinone

A process is provided for the coloration of a preformed polyester resin shaped article having improved dye migration properties, which comprises:

Process for coloring polyester shaped articles

A method is provided for preparing a polymer bound stabilizer which comprises reacting a stabilizer precursor molecule containing a reactive double bound which is not readily homopolymerizable with a pre-formed polymer in the presence of a free radical.

Method for preparing polymer bound stabilizers made from

An N-t-alkyl-N-sec-alkyl secondary amine compound of the formula: ##STR1## wherein X, Y and Z are each independently selected from --H, --OH, or an alkyl group having from 1 to about 15 carbon atoms; and n is an integer of from 3 to about 6.

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Spartanburg, SC, United States of America

John W Rekers