CA2518271A1 - Polyamide-polyether block copolymer - Google Patents

Polyamide-polyether block copolymer Download PDF

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CA2518271A1
CA2518271A1 CA002518271A CA2518271A CA2518271A1 CA 2518271 A1 CA2518271 A1 CA 2518271A1 CA 002518271 A CA002518271 A CA 002518271A CA 2518271 A CA2518271 A CA 2518271A CA 2518271 A1 CA2518271 A1 CA 2518271A1
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copolymer
compound
reaction mixture
diamine
diacid
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CA2518271C (en
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Mark S. Palvin
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Kraton Chemical LLC
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/40—Polyamides containing oxygen in the form of ether groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/028—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyamide sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/126—Copolymers block
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers

Abstract

Copolymers having linked internal polyether blocks and internal polyamide blocks have advantageous physical properties and solvent-gelling abilities.
The copolymer may be prepared from a reaction mixture that contains 1,4-cyclohexane dicarboxylic acid (CHDA) and poly(alkyleneoxy) diamine (PAODA).
Optionally, the reaction mixture contains no monofunctional compound reactive with either amine or carboxylic acid groups, however some of this monofunctional compound may be present. Dimer diamine and/or dimer acid may be present in the reaction mixture. A copolymer may also be prepared from a reaction mixture containing dimer acid and at least two diamine compound(s) including PAODA and short-chain aliphatic diamine having 2-6 carbons (SDA), wherein: a) the reaction mixture comprises x grams of PAODA and y grams of SDA, and x/(x+y) is 0.8-0.98; b) the reaction mixture weighs z grams, and x/z is at least 0.25; and c) the reaction mixture contains either no co-diacid, or comprises a small amount of co-diacid, wherein, if the reaction mixture comprises a small amount of co-diacid, then acid equivalents from co-diacid contribute less than 25% of the total acid equivalents present in the reaction mixture.

Claims (37)

1. A polyamide-polyether block copolymer having a softening point between 60°C and 180°C formed from a reaction mixture comprising one or more diacid compound(s) comprising 1,4-cyclohexane dicarboxylic acid (CHDA), and one or more diamine compound(s) comprising poly(alkyleneoxy) diamine (PAODA), the reaction mixture containing no monofunctional compound reactive with either amine or carboxylic acid groups, wherein the diamine compound(s) further comprise dimer diamine.
2. A polyamide-polyether block copolymer having a softening point between 60°C and 180°C formed from a reaction mixture comprising one or more diacid compound(s) comprising 1,4-cyclohexane dicarboxylic acid (CHDA), one or more diamine compound(s) comprising poly(alkyleneoxy) diamine (PAODA), and one or more monofunctional compound(s) reactive with carboxylic acid groups, wherein the diamine compound(s) further comprise dimer diamine.
3. A polyamide-polyether block copolymer having a softening point between 60°C and 180°C formed from a reaction mixture comprising one or more diacid compound(s) comprising 1,4-cyclohexane dicarboxylic acid (CHDA), one or more diamine compound(s) comprising poly(alkyleneoxy) diamine (PAODA), and one or more monofunctional compound(s) reactive with amine groups, wherein the diamine compound(s) further comprise dimer diamine.
4. The copolymer of any of claims 1-3 wherein the softening point is between 100°C and 140°C.
5. The copolymer of claim any of claims 1-3 wherein CHDA is the only diacid compound present in the reaction mixture.
6. The copolymer of any of claims 1-3 wherein CHDA provides at least 45% of the acid equivalents attributed to the diacid compound(s).
7. The copolymer of any of claims 1-3 wherein the diacid compound(s) further comprise polymerized fatty acid.
8. The copolymer of any of claims 1-3 wherein polymerized fatty acid provides less than 25% of the equivalents of the acid groups attributed to the diacid compound(s).
9. The copolymer of claim 1 wherein the reaction mixture comprises a mono-hydric compound.
10. The copolymer of claim 9 wherein the mono-hydric compound is poly(alkyleneoxy) monoalcohol.
11.The copolymer of claim 1 wherein the reaction mixture comprises a monoamine compound.
12. The copolymer of claim 11 wherein the monoamine compound is poly(alkyleneoxy) monoamine.
13. The copolymer of any of claims 1-3 wherein the reaction mixture further comprises a dihydric compound.
14. The copolymer of claim 13 wherein the dihydric compound is poly(alkyleneoxy) dialcohol.
15. The copolymer of claim 13 wherein the poly(alkyleneoxy) dialcohol compound is present in the reaction mixture in an amount of less than 40 eq. %
of the total equivalents of amine and hydroxyl present in the reaction mixture.
16. The copolymer of any of claims 1-3 herein the reaction mixture further comprises a co-diacid.
17. The copolymer of claim 16 wherein the co-diacid is selected from the group consisting of adipic acid, sebacic acid, azelaic acid, isophthalic acid, dodecanedioic acid, and 1,3-cyclohexane dicarboxylic acid.
18. The copolymer of any of claims 1-3 wherein the PAODA provides at least 20% of the amine equivalents attributed to the diamine compound(s) present in the reaction mixture.
19. The copolymer of any of claims 1-3 wherein the PAODA includes PAODA compounds having molecular weights between 400 and 5,000.
20. The copolymer of any of claims 1-3 wherein the diamine compound(s) exclude diamines of the formula H2N-R2-NH2 wherein R2 is C2-C6 hydrocarbyl.
21. The copolymer of any of claims 1-3 wherein the diamine compound(s) include diamines of the formula H2N-R2-NH2 wherein R2 is C2-C6 hydrocarbyl, however diamines of the formula H2N-R2-NH2 wherein R2 is C2-C6 hydrocarbyl provide less than 10% of the amine equivalents attributed to diamine compound(s).
22. The copolymer of any of claims 1-3 having a weight average molecular weight of between 10,000 and 40,000, as measured using gel permeation chromatography with polystyrene as reference standards.
23. The copolymer of claim 2 that includes a compound of formula (3):
wherein, in at least one occurrence, R1 is a C6 carbocyclic group; R2 is a polyalkyleneoxide moiety; R4 is selected from a hydrocarbon group having at least 4 carbons and a polyalkyleneoxide moiety having a formula weight of at least 100; and n is an integer of at least 11.
24. The copolymer of claim 2 that includes a compound of formula (4):
wherein, in at least one occurrence, R1 is a C6 carbocyclic group; R2 is a polyalkyleneoxide moiety; R5 is selected from a hydrocarbon group having at least 4 carbons and a polyalkyleneoxide moiety having a formula weight of at least 100; and n is an integer of at least 11.
25. The copolymer of claim 3 that includes a compound of formula (5):
wherein, in at least one occurrence, R1 is a C6 carbocyclic group; R2 is a polyalkyleneoxide moiety; R3 is a hydrocarbon group having at least 2 carbons;
and n is an integer of at least 11.
26. The copolymer of any of claims 1-3 having an amine number of less than 10 and an acid number of less than 15.
27. The copolymer of any of claims 1 to 3, wherein:
a) the copolymer has a softening point between 100°C and 140°C;
b) CHDA provides at least 45% of the acid equivalents attributed to diacid compound(s);
c) polymerized fatty acid is present in the reaction mixture, however polymerized fatty acid provides less than 25% of the equivalents of acid groups attributed to the diacid compound(s); and d) PAODA provides at least 20% of the amine equivalents attributed to the diamine compound(s).
28. A polyamide-polyether block copolymer having a softening point between 60°C and 180°C formed from a reaction mixture comprising one or more diacid compound(s) including polymerized fatty acid, and at least two diamine compound(s) including poly(alkyleneoxy) diamine (PAODA) and short-chain aliphatic diamine having 2-6 carbons (SDA), wherein:
a) the reaction mixture comprises x grams of PAODA and y grams of SDA, and x/(x+y) is 0.8-0.98;
b) the reaction mixture weighs z grams, and x/z is at least 0.25; and c) the reaction mixture contains either no co-diacid, or comprises a minor amount of co-diacid, wherein, if the reaction mixture comprises a minor amount of co-diacid, then acid equivalents from co-diacid contribute less than 25% of the total acid equivalents present in the reaction mixture.
29. The copolymer of claim 28 wherein the softening point is between 100°C and 140°C.
30. The copolymer of claim 28 wherein polymerized fatty acid is the only diacid compound present in the reaction mixture.
31. The copolymer of claim 28 wherein co-diacid is present in the reaction mixture, however, co-diacid contributes less than 10% of the total acid equivalents present in the reaction mixture.
32. The copolymer of claim 28 wherein PAODA and SDA together constitute at least 95 wt% of the diamine compounds present in the reaction mixture.
33. The copolymer of claim 28 wherein the diamine compound(s) include poly(alkyleneoxy) diamine having a molecular weight of at least 400 g/mol.
34. The copolymer of claim 28 wherein x/z is at least 0.3.
35. The copolymer of claim 32 were x/z is at least 0.4.
36. A composition comprising a) a copolymer of any of claims 1-3 and claim 28 and b) a compound, where the compound is a liquid at room temperature in neat form.
37. The composition of claim 36 in the form of a gel.

42. The composition of claim 40 wherein the compound comprises at least one chemical group selected from ester, ether, halogen, carbonate and sulfoxide.

43. An article of manufacture comprising a copolymer of any of claims 1-6 and 30.

44. An article of manufacture of claim 43 formulated as a fragrance stick, an air freshener or a fragrance gel.

45. An article of manufacture of claim 43 formulated as a personal care product comprising at least one physiologically acceptable oil.

46. The article of claim 43 further comprising a surfactant having an HLB value between 4 and 20.

47. The article of claim 43 further comprising at least one of a colorant and a fragrance.
CA2518271A 2003-03-20 2004-02-20 Polyamide-polyether block copolymer Expired - Lifetime CA2518271C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/395,050 US6956099B2 (en) 2003-03-20 2003-03-20 Polyamide-polyether block copolymer
US10/395,050 2003-03-20
PCT/IB2004/000501 WO2004083280A1 (en) 2003-03-20 2004-02-20 Polyamide-polyether block copolymer

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CA2518271A1 true CA2518271A1 (en) 2004-09-30
CA2518271C CA2518271C (en) 2012-04-17

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US (7) US6956099B2 (en)
EP (1) EP1606334B1 (en)
JP (2) JP4553896B2 (en)
KR (1) KR101084837B1 (en)
CN (1) CN100586986C (en)
CA (1) CA2518271C (en)
ES (1) ES2729823T3 (en)
MX (1) MXPA05010043A (en)
WO (1) WO2004083280A1 (en)

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