DIHYDROXYALKYL SUBSTITUTED POLYGALACTOMANNAN, AND METHODS FOR PRODUCING AND USING THE SAME

• US 20150098921A1
• Filed: 10/02/2014
• Published: 04/09/2015
• Est. Priority Date: 10/07/2013
• Status: Active Grant

• Current Assignee: Hercules, LLC (Ashland Global Holdings, Inc.)
• Original Assignee: Hercules Incorporated (Ashland Global Holdings, Inc.)
• Inventors: FRANZKE, Michael Albert Hermann, ZHANG, Xiaochun, KROON, Gijsbert
• Granted Patent: US 9,782,609 B2
• Time in Patent Office: Days
• US Class Current: 424/70.13
• CPC Class Codes: A61K 2800/54 Polymers characterized by specific structures/properties
• CPC Class Codes: A61K 2800/5426 cationic
• CPC Class Codes: A61K 8/60 Sugars; Derivatives thereof
• CPC Class Codes: A61K 8/737 Galactomannans, e.g. guar; Derivatives thereof
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring
• CPC Class Codes: C08B 37/0087 Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
• CPC Class Codes: C08B 37/009 Konjac gum or konjac mannan, i.e. beta-D-glucose and beta-D-mannose units linked by 1,4 bonds, e.g. from Amorphophallus species; Derivatives thereof
• CPC Class Codes: C08B 37/0093 Locust bean gum, i.e. carob bean gum, with (beta-1,4)-D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from the seeds of carob tree or Ceratonia siliqua; Derivatives thereof
• CPC Class Codes: C08B 37/0096 Guar, guar gum, guar flour, guaran, i.e. (beta-1,4) linked D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from Cyamopsis Tetragonolobus; Derivatives thereof

Abstract

Disclosed are compositions including dihydroxyalkyl substituted polygalactomannan, and the optional further substitution of such with cationic and/or hydrophobic moieties. Method of making such compositions is also disclosed as well as the use of such compositions in industrial applications, fabric laundering, and personal and household care.

Claims

1-84. -84. (canceled)

85. A composition comprising a polygalactomannan substituted with at least one dihydroxyalkyl moiety, wherein the composition comprises unsubstituted mannose, substituted mannose, unsubstituted galactose and substituted galactose, and wherein the molar ratio of the combined unsubstituted mannose and substituted mannose to the combined unsubstituted galactose and substituted galactose is at least about 2.0:

1.

86. The composition of claim 85, wherein the molar ratio of the unsubstituted mannose to the unsubstituted galactose is from about 2.0:

1 to about 7.0;

1.

87. The composition of claim 85, wherein the at least one dihydroxyalkyl moiety is substituted on the polygalactomannan in the form of an ether.

88. The composition of claim 85, wherein the average degree of molar substitution of the polygalactomannan by the at least one dihydroxyalkyl moiety is in a range of from about 0.05 to about 5.0.

89. The composition of claim 85 having a number average molecular weight (M_n) in a range of from about 50,000 to about 1,000,000, and a weight average molecular weight (M_w) in a range of from about 70,000 to about 1,200,000.

90. The composition of claim 85, wherein the dihydroxyalkyl moiety is dihydroxypropyl moiety.

91. The composition of claim 85, wherein the polygalactomannan is further substituted with at least one cationic moiety.

92. The composition of claim 91, wherein the polygalactomannan is further substituted with at least one hydrophobic moiety.

93. The composition of claim 92, wherein the at least one hydrophobic moiety is substituted on the at least one cationic moiety.

94. The composition of claim 92, wherein the at least one hydrophobic moiety is selected from a C₄-C₂₂ alkyl radical.

95. The composition of claim 85, wherein the polygalactomannan is further substituted with at least one hydrophobic moiety.

96. The composition of claim 95, wherein the at least one hydrophobic moiety is selected from a C₄-C₂₂ alkyl radical.

97. The composition of claim 85 further comprising at least one component selected from the group consisting of surfactants, fatty acid soap, hair and skin conditioning agents, suspending aids, emollients, emulsifiers, rheology modifiers, thickening agents, vitamins, hair growth promoters, self-tanning agents, sunscreens, skin lighteners, anti-aging compounds, anti-wrinkle compounds, anti-cellulite compounds, anti-acne compounds, anti-dandruff agents, anti-inflammatory compounds, analgesics, antiperspirant agents, deodorant agents, hair fixatives, particulates, abrasives, moisturizers, antioxidants, keratolytic agents, anti-static agents, foam boosters, hydrotropes, solublizing agents, chelating agents, antimicrobial agents, antifungal agents, pH adjusting agents, chelating agents, buffering agents, botanicals, hair colorants, hair dye, oxidizing agents, reducing agents, hair and skin bleaching agents, pigments, anticaries, anti-tartar agents, anti-plaque agents, solvents, a rheology modifier, and combinations thereof.

98. A hair fixative composition comprising:

a) the composition of claim 85; and

b) a component selected from a rheology modifier, a surfactant, an auxiliary fixative, a solvent, water, a conditioner, a propellant, neutralizing agent, fragrance, fragrance solubilizer, thickener, preservative, emulsifier, emollient, humectant, colorant, wax, and mixtures thereof.

99. The hair fixative composition of claim 98, wherein the conditioner is selected from the group consisting of silicones, organic conditioning oils, natural and synthetic waxes, cationic polymers, and combinations thereof.

100. The hair fixative composition of claim 98, wherein the propellant is selected from the group consisting of propane, butane, isobutane, dimethyl ether, 1,1-difluoroethane, HFO-1234ze (tetrafluoropropylene), carbon dioxide, and mixtures thereof.

101. The composition of claim 85, wherein the polygalactomannan is isolated from the endosperm of the seeds of Cassia tora, Cassia obtusifolia, or combinations thereof.

102. A method for making a dihydroxypropyl-substituted-polygalactomannan comprising:

a) combining an aqueous caustic solution with polygalactomannan comprising mannose and galactose at a molar ratio of mannose to galactose of at least about 2.0;

1 to form a first mixture wherein at least a portion of the polygalactomannan is alkalized;

b) adding a compound selected from the group consisting of 3-chloro-1,2-propanediol, 3-bromo-1,2-dihydroxypropanediol, 3-iodo-1,2-dihydroxypropanediol, 3-tosyl-1,2-dihydroxypropanediol, 3-chloro-2-hydroxypropyl phenyl/alkyl ether, 2,3-epoxy propyl phenyl ether, glycidol, and combinations thereof, to the first mixture to form a second mixture;

c) heating the second mixture to a temperature of from about 40°

C. to about 140°

C. for a period of about 1 to about 4 hours to substitute at least one dihydroxypropyl moiety onto the polygalactomannan to form the dihydroxypropyl-substituted-polygalactomannan;

d) cooling the second mixture to a temperature of from about 10 to about 60°

C. and adjusting the pH of the second mixture to about 6.0 to 8.5; and

e) recovering the dihydroxypropyl-substituted-polygalactomannan from the second mixture.

103. The method of claim 102 further comprising:

f) combining the dihydroxypropyl-substituted-polygalactomannan with a second aqueous caustic solution wherein at least a portion of the dihydroxypropyl-substituted-polygalactomannan is alkalized to form a third mixture;

g) adding a cationic compound to the third mixture to form a fourth mixture;

h) heating the fourth mixture to a temperature of from about 30°

C. to about 100°

C. for a period of about 1 to about 4 hours to substitute at least one cationic moiety onto the dihydroxypropyl-substituted-polygalactomannan to form a cation-and-dihydroxypropyl-substituted-polygalactomannan;

i) cooling the fourth mixture to a temperature of from about 10 to about 50 and adjusting the pH of the fourth mixture to about 6.0 to 8.5; and

j) recovering the cation-and-dihydroxypropyl-substituted-polygalactomannan from the fourth mixture.

104. The method of claim 103 further comprising:

k) combining the cation-and-dihydroxypropyl-substituted-polygalactomannan with a third aqueous caustic solution wherein at least a portion of the cation-and-dihydroxypropyl-substituted-polygalactomannan is alkalized thereby forming a fifth mixture;

l) adding a hydrophobic compound to the fifth mixture to form a sixth mixture;

m) heating the sixth mixture to a temperature of from about 30°

C. to about 140°

C. for a period of about 1 to about 4 hours to substitute at least one hydrophobic moiety onto the cation-and-dihydroxypropyl-substituted-polygalactomannan to form a hydrophobic-and-cation-and-dihydroxypropyl-substituted-polygalactomannan;

n) cooling the sixth mixture to a temperature of from about 10 to about 50°

C. and adjusting the pH of the sixth mixture to about 6.0 to 8.5; and

o) recovering the hydrophobic-and-cation-and-dihydroxypropyl-substituted-polygalactomannan from the sixth mixture.