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US 12,679,943 B2Granted
Additive for reducing polyurethane foam degradation
AssigneeHuntsman International LLC
InventorsPietro Buono, Dion Deriks, Wouter Geers, Heiko Heinrich Humbert, Geert Lodewijk Dries, Petra Emma Vanderstraeten
Life of this patent
Estimating the term…
Abstract
The present disclosure relates to sulfonic acid esters for use as additives in a polyurethane formulation. The polyurethane formulation further includes a compound containing an isocyanate functional group, an active hydrogen-containing compound and a reactive amine catalyst.
Claims15
A polyurethane formulation comprising:
- (a) a sulfonic acid ester selected from (i) a compound having a formula (1)
- where R1 is a C1-C18 alkyl group with one or more hydroxyl groups or a C1-C18 alkoxy group with one or more hydroxyl groups and R2 is a methyl group, a C1-C18 alkyl group with one or more hydroxyl groups or a C1-C18 alkoxy group with one or more hydroxyl groups;
- (ii) a compound having a formula (2)
- where X is hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl group which may be substituted with one or more hydroxyl groups or a C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups and R2 is a methyl group, a C1-C18 alkyl group with one or more hydroxyl groups or C1-C18 alkoxy group with one or more hydroxyl groups;
- (iii) a compound having the formula (3)
- where each X is independently hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl group which may be substituted with one or more hydroxyl groups or C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups, n is an integer from 1 to 8 and R3 is H, a C1-C4 alkyl group which may be substituted with one or more hydroxyl groups or a or C1-C4 alkoxy group which may be substituted with one or more hydroxyl groups;
- (iv) a compound having a formula (4)
- where n is an integer from 1 to 5;
- (v) a compound having the formula (5)
- where n is an integer from 1 to 3 and X is hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl group which may be substituted with one or more hydroxyl groups or C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups;
- and (vi) a mixture thereof;
- (b) a compound containing an isocyanate functional group;
- (c) an active hydrogen-containing compound;
- and (d) an isocyanate-reactive amine catalyst comprising at least one tertiary amine group and corresponding to formula (6)
- wherein
- R4 and R5 are independently a C1-C4 alkyl group or R4 and R5 together form a cyclic 5-membered or 6-membered ring containing an O or a N heteroatom or a 7-membered bicyclic structure,
- m is an integer 1 or 2, and
- Y is selected from —OH, —NH2, —N(CH3) CH2CH2OH, —NHCH2CH2CH2N(CH3)2, —N(CH3) CH2CH2CH2NH2, —N(CH2CH(CH3)OH)2, —N(CH2CH(CH3) OH) CH2CH2CH2N(CH3)2, —OCH2CH2OH, —OCH2CH2NH2, —OCH2CH2CH2NH2, —OCH2CH2N(CH3) CH2CH2OH, and —OCH2CH2N(CH3) CH2CH2CH2NH2, and
- characterized in that the molar ratio of the total number of moles of the at least one tertiary amine group present in isocyanate-reactive amine catalyst (d) to the number of moles of sulfonic acid ester compound (a) in the polyurethane formulation is higher or equal than 2.
16 more elements
The polyurethane formulation according to any of foregoing claims, further comprising a blowing agent.
A method for producing a polyurethane material comprising preparing a formulation by combining and/or reacting a compound containing an isocyanate functional group, an active hydrogen-containing compound and optional auxiliary components, in the presence of an isocyanate-reactive amine catalyst comprising at least one tertiary amine group according to formula (6)
- wherein
- R4 and R5 are independently a C1-C4 alkyl group or R4 and R5 together form a cyclic 5-membered or 6-membered ring containing an O or a N heteroatom or a 7-membered bicyclic structure,
- m is an integer 1 or 2, and
- Y is selected from —OH, —NH2, —N(CH3) CH2CH2OH, —NHCH2CH2CH2N(CH3)2, —N(CH3) CH2CH2CH2NH2, —N(CH2CH(CH3)OH)2, —N(CH2CH(CH3) OH) CH2CH2CH2N(CH3)2, —OCH2CH2OH, —OCH2CH2NH2, —OCH2CH2CH2NH2, —OCH2CH2N(CH3) CH2CH2OH, and —OCH2CH2N(CH3) CH2CH2CH2NH2,
- and
- in the presence of a sulfonic acid ester selected from (i) a compound having a formula (1)
- where R1 is a C1-C18 alkyl group with one or more hydroxyl groups or a C1-C18 alkoxy group with one or more hydroxyl groups and R2 is a methyl group, a C1-C18 alkyl group with one or more hydroxyl groups or a C1-C18 alkoxy group with one or more hydroxyl groups;
- (ii) a compound having a formula (2)
- where X is hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl group which may be substituted with one or more hydroxyl groups or a C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups and R2 is a methyl group, a C1-C18 alkyl group with one or more hydroxyl groups or a C1-C18 alkoxy group with one or more hydroxyl groups;
- (iii) a compound having the formula (3)
- where each X is independently hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl group which may be substituted with one or more hydroxyl groups or a C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups, n is an integer from 1 to 8 and R3 is H or a C1-C4 alkyl group or C1-C4 alkoxy group which may be substituted with one or more hydroxyl groups;
- (iv) a compound having a formula (4)
- where n is an integer from 1 to 5;
- (v) a compound having the formula (5)
- where n is an integer from 1 to 3 and X is hydrogen or an ortho, meta or para substituent selected from a C1-C18 alkyl which may be substituted with one or more hydroxyl groups or a C1-C18 alkoxy group which may be substituted with one or more hydroxyl groups;
- and (vi) a mixture thereof characterized in that the molar ratio of the number of moles of the at least one tertiary amine group present in isocyanate-reactive amine catalyst (d) to the number of moles of sulfonic acid ester compound (a) in the formulation is higher or equal than 2.
13 more elements
Dependencies are inferred from the claim text.