Method for preparing a polyurethane foam
AssigneesUniversite De Bordeaux, Institut Polytechnique De Bordeaux, Centre National De La Recherche Scientifique
InventorsYannick LANDAIS, Henri CRAMAIL, Ikechukwu Martin OGBU, Thomas VIDIL, Frédéric ROBERT, Etienne GRAU, Quentin JAUSSAUD
Life of this patent
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Abstract
The invention relates to a method for preparing a polyurethane foam (I) comprising a) reacting, at a temperature ranging from 60 to 150° C., at least one poly oxamic acid (III) with at least one polyol (II) in the presence of a hypervalent iodine oxidant; b) foaming the polyurethane (I) obtained in step a) in the presence of carbon dioxide. The invention also relates to a polyurethane foam (I) obtained according to the method of the invention.
Claims21
A method for preparing a polyurethane foam (I) characterized in that it comprises:
- a) reacting, in the presence of an oxidant and at a temperature ranging from 60 to 150° C., at least one poly oxamic acid of formula (II):
- with at least one polyol of formula (III):
- to generate in situ carbon dioxide and at least one polyisocyanate,
- in which:
- the oxidant is a hypervalent iodine compound,
- L1 represents a saturated, linear or branched, cyclic or acyclic hydrocarbon group in which one or more CH2 have optionally been replaced by O and/or S;
- or an unsaturated, linear or branched hydrocarbon group including at least one double bond and/or at least one aromatic ring optionally substituted by one or more alkyl and/or alkoxy groups;
- or a saturated, linear or branched, cyclic or acyclic hydrocarbon group comprising one or more COOH or polyethylene glycol substituents;
- or a triester of fatty acids of which one or more CH2 have optionally been replaced by O and/or S,
- L2 represents a saturated, linear or branched, cyclic or acyclic hydrocarbon group in which one or more CH2 have optionally been replaced by O;
- or an unsaturated, linear or branched hydrocarbon group in which one or more CH2 have optionally been replaced by O and including at least one aromatic ring optionally substituted by one or more alkyl and/or alkoxy groups or at least one aromatic heterocycle;
- or a triester of fatty acids;
- or a di, tri or tetra polyester of polyalkylene glycol,
- x represents an integer greater than or equal to 2, and
- y represents an integer greater than or equal to 2,
- it being understood that at least one of x or y is greater than or equal to 3, and
- b) foaming the polyurethane (I) obtained in step a) in the presence of carbon dioxide.
The preparation method according to any one of the preceding claims wherein steps a) and b) are carried out concomitantly.
The preparation method according to any one of the preceding claims according to which L1 is selected from the following groups:
- with:
- R1, R1′, R1″, R2, R2′, R3, R3′, R3″, R4, R4′, R5, R5′, R6 and R6′ identical or different and independently representing H, (CH2)i, CH3, CH3—(CH2)i, CH3O, CH3—(CH2)iO, CH3S, CH3—(CH2)iS, (CH2)iS, (CH2)iCH(CH3)S or CH3—(CH2)iCH(CH3)S,
- R2 and R3 which can together represent a CH(R7a)-CH(R7b)-CH(R7c)-CH(R7d) group with R7a, R7b, R7c and R7d identical or different and independently representing H, (CH2)i, CH3, CH3—(CH2)i, CH3O or CH3—(CH2)iO,
- it being understood that at least two groups among R1, R1″, R2, R3, R3″, R4, R5 and R6 and at least two groups among R1′, R2′, R3′, R4′, R5′ and R6′ represent (CH2)i,
- R8, R9, R10, R11 and R12 identical or different and independently representing H, (CH2)i, CH3, CH3—(CH2)i, O(CH2)i, CH3O or CH3—(CH2)iO,
- R11 and R12 which together can represent a O—CH(R7a)-CH(R7b)-CH(R7c)-(CH(R7d))j group, it being understood that at least two groups among R7a, R7b, R7c, R7d, R8, R9, R10, R11 and R12 represent (CH2)i or O(CH2)i,
- R13, R14, R15, R16, R13′, R14′, R15′ and R16′ identical or different and independently representing H, CH3(CH2)k or CH3(CH2)kO,
- R17 representing H or CH3(CH2)k,
- R18 and R18′ independently representing H, CH3(CH2)k, CH2[OCH2 CH2]mOH, or CH2[OCH2CHCH3]mNHCOCOOH,
- A representing a hydrocarbon, linear or branched chain including from 12 to 30 carbon atoms, and of which one or more CH2 have been replaced by S,
- i representing an integer ranging from 0 to 20,
- j representing 0 or 1,
- k representing an integer ranging from 0 to 6,
- m, m′ and m″ being identical or different and independently representing an integer ranging from 1 to 500, and
- p representing an integer ranging from 1 to 6.
The preparation method according to any one of the preceding claims, according to which x is equal to 2 or 3.
The method according to any one of the preceding claims according to which L1 is selected from:
The method according to any one of the preceding claims, according to which L1 is selected from:
- (CH2)m (L1-1) and
The preparation method according to any one of the preceding claims, according to which L2 is selected from the following groups:
- with:
- 20, R21, R22, R23, R24 and R25 being identical or different and independently representing H, (CH2)s, CH3 or CH3—(CH2)s,
- R21 and R22 which can together represent a group CH(R22a)-CH(R22b)-CH(R22c)-CH(R22d) with R22a, R22b, R22c and R22d identical or different and independently representing H, (CH2)s, CH3 or CH3—(CH2)s,
- it being understood that at least two groups among R20, R21, R22, R22a, R22b, R22c and R22d, R23, R24 and R25 represent (CH2)s,
- R26, R27, R28, R29, R30 and R31 being identical or different and independently representing H, (CH2)s, CH3, CH3—(CH2)s, O(CH2)s, CH3O or CH3—(CH2)sO, it being understood that at least two groups among R26, R27, R28, R29, R30 and R31 represent (CH2)s or O(CH2)s,
- R32, R33, R34, R36, R36′, R45, R47, R48 and R49 independently representing H, CH3 or CH3(CH2)r,
- R35 representing CH3, CH3(CH2)r or HO(CH2)r,
- R37, R38, R39, R40, R41, R42, R43 and R44 being identical or different and independently representing H, (CH2)s, CH3, CH3—(CH2)s, O(CH2)s, CH3O or CH3—(CH2)sO,
- R46 representing (CH2)r, benzylene or cyclohexylene,
- B representing a hydrocarbon, linear or branched chain including from 12 to 30 carbon atoms, and including at least one double bond,
- s representing an integer ranging from 1 to 18,
- r representing an integer ranging from 1 to 6,
- t representing an integer ranging from 1 to 500,
- u representing 0, 1, 2 or 3,
- w representing 0 or 1,
- z representing an integer ranging from 0 to 4.
The preparation method according to any one of the preceding claims, according to which y is equal to 3 or 4.
The method according to any one of the preceding claims according to which L2 is selected from:
The method according to any one of the preceding claims according to which L2 represents:
The preparation method according to any one of the preceding claims, according to which the oxidant is selected from bis(trifluoroacetoxy)iodobenzene, bis(acetoxy)iodobenzene, poly[4-(diacetoxyiodo)styrene], hydroxybenziodoxole, and acetoxybenziodoxole.
The method according to any one of the preceding claims, comprising a step c), subsequent to step b), of purifying the polyurethane foam (I), preferably by heating and/or under reduced pressure.
The method according to any one of the preceding claims, according to which the reaction between the at least one poly oxamic acid and the at least one polyol is carried out in the presence of a non-ionic surfactant (IV).
The method according to the preceding claim according to which the surfactant (IV) is selected from:
- with:
- R50 representing OH, CH3—(CH2)hO or O(CO)(CH2)hCH3 with h representing an integer ranging from 0 to 3,
- a, b, c, d, e, f and g being identical or different and independently representing an integer ranging from 0 to 500.
The preparation method according to any one of the preceding claims carried out in a closed reactor and under reduced pressure.
The preparation method according to any one of the preceding claims, wherein the polyurethane foam (I) is purified by a heating step and/or under reduced pressure.
A polyurethane foam obtained according to the preparation method according to any one of the preceding claims.
The polyurethane foam according to the preceding claim, the density of which ranges from 10 to 1000 kg·m−3, preferably from 100 to 300 kg·m−3, the density being the ratio of the mass of the foam measured with a balance, and the apparent volume of the foam determined by measuring the dimensions of the foam with a caliper.
Dependencies are inferred from the claim text.